//
//  Copyright (C) 2020 Schrödinger, LLC
//
//   @@ All Rights Reserved @@
//  This file is part of the RDKit.
//  The contents are covered by the terms of the BSD license
//  which is included in the file license.txt, found at the root
//  of the RDKit source tree.
//

#include <bitset>
#include <list>
#include <string>
#include <vector>

#include "catch.hpp"

#include <GraphMol/MolOps.h>
#include <GraphMol/SmilesParse/SmilesParse.h>
#include <GraphMol/FileParsers/FileParsers.h>

#include "CIPLabeler.h"
#include "Digraph.h"
#include "rules/Pairlist.h"
#include "rules/Rule1a.h"
#include "rules/Rule2.h"

#include "CIPMol.h"

using namespace RDKit;
using namespace RDKit::CIPLabeler;

std::string toBinaryString(int value) {
  return std::bitset<32>(value).to_string();
}

TEST_CASE("Descriptor lists", "[accurateCIP]") {
  auto descriptors = PairList();

  SECTION("IgnoreConstructionNulls") {
    CHECK(!descriptors.add(Descriptor::NONE));
    CHECK(!descriptors.add(Descriptor::UNKNOWN));
    CHECK(!descriptors.add(Descriptor::ns));
  }
  SECTION("IgnoreConstructionPseudo") {
    CHECK(!descriptors.add(Descriptor::r));
    CHECK(!descriptors.add(Descriptor::s));

    CHECK(descriptors.add(Descriptor::R));
    CHECK(descriptors.add(Descriptor::S));
  }
  SECTION("Pairing") {
    REQUIRE(descriptors.getPairing() == 0);

    CHECK("00000000000000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));

    descriptors.add(Descriptor::R);
    CHECK("00000000000000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));

    // like
    descriptors.add(Descriptor::R);
    CHECK("01000000000000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));

    // like
    descriptors.add(Descriptor::R);
    CHECK("01100000000000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));

    // unlike
    descriptors.add(Descriptor::S);
    CHECK("01100000000000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));

    // like
    descriptors.add(Descriptor::R);
    CHECK("01101000000000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));

    // like
    descriptors.add(Descriptor::R);
    CHECK("01101100000000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));

    // like
    descriptors.add(Descriptor::R);
    CHECK("01101110000000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));

    // unlike
    descriptors.add(Descriptor::S);
    CHECK("01101110000000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));

    // like
    descriptors.add(Descriptor::R);
    CHECK("01101110100000000000000000000000" ==
          toBinaryString(descriptors.getPairing()));
  }

  SECTION("pairRM") {
    PairList list1 = PairList();
    PairList list2 = PairList();
    list1.add(Descriptor::R);
    list1.add(Descriptor::M);
    list1.add(Descriptor::R);
    list1.add(Descriptor::S);
    list2.add(Descriptor::R);
    list2.add(Descriptor::P);
    list2.add(Descriptor::S);
    list2.add(Descriptor::M);
    CHECK(list1.toString() == "R:llu");
    CHECK(list2.toString() == "R:uul");
  }
}

void check_incoming_edge_count(Node *root) {
  auto queue = std::list<Node *>({root});

  for (const auto &node : queue) {
    int incoming_edges = 0;
    for (const auto &e : node->getEdges()) {
      if (!e->isBeg(node)) {
        REQUIRE(e->isEnd(node));
        ++incoming_edges;
      } else if (!e->getEnd()->isTerminal()) {
        queue.push_back(e->getEnd());
      }
    }

    // Only the current root should have no incoming nodes.
    // All other nodes should have exactly one incoming edge.
    if (node == root) {
      CHECK(incoming_edges == 0);
    } else {
      CHECK(incoming_edges == 1);
    }
  }
}

void expandAll(Digraph &g) {
  auto queue = std::list<Node *>({g.getOriginalRoot()});

  for (const auto &node : queue) {
    for (const auto &e : node->getEdges()) {
      if (!e->isBeg(node)) {
        continue;
      }
      if (!e->getEnd()->isTerminal()) {
        queue.push_back(e->getEnd());
      }
    }
  }
}

TEST_CASE("Digraph", "[accurateCIP]") {
  auto mol =
      R"(CC1(OC2=C(C=3NC[C@@]4(C3C=C2)C([C@@H]5C[C@@]67C(N([C@]5(C4)CN6CC[C@@]7(C)O)C)=O)(C)C)OC=C1)C)"_smiles;  // VS040
  CIPLabeler::CIPMol cipmol(*mol);

  auto initial_root_idx = 1u;
  auto initial_root_atom = cipmol.getAtom(initial_root_idx);

  Digraph g(cipmol, initial_root_atom);
  expandAll(g);
  REQUIRE(g.getNumNodes() == 3819);

  auto current_root = g.getCurrentRoot();
  REQUIRE(current_root->getAtom()->getIdx() == initial_root_idx);

  check_incoming_edge_count(current_root);

  auto new_root_idx = 24u;
  auto new_root_atom = cipmol.getAtom(new_root_idx);
  auto new_root_nodes = g.getNodes(new_root_atom);
  CHECK(new_root_nodes.size() == 104);

  Node *new_root_node = *new_root_nodes.begin();
  for (const auto &node : new_root_nodes) {
    if (!node->isDuplicate() &&
        node->getDistance() > new_root_node->getDistance()) {
      new_root_node = node;
    }
  }
  REQUIRE(new_root_node->getDistance() == 25);

  g.changeRoot(new_root_node);
  REQUIRE(g.getNumNodes() == 3819);

  current_root = g.getCurrentRoot();
  REQUIRE(current_root->getAtom()->getIdx() == new_root_idx);

  check_incoming_edge_count(current_root);
}

TEST_CASE("Rule1a", "[accurateCIP]") {
  SECTION("Compare equal") {
    auto mol = "COC"_smiles;
    CIPLabeler::CIPMol cipmol(*mol);
    Digraph g(cipmol, cipmol.getAtom(1));
    auto origin = g.getOriginalRoot();

    auto frac = origin->getAtomicNumFraction();
    REQUIRE(frac.numerator() == 8);
    REQUIRE(frac.denominator() == 1);

    Rule1a rule;

    auto edges = origin->getEdges();
    REQUIRE(edges.size() == 2);
    REQUIRE(edges[0] != edges[1]);

    CHECK(0 == rule.compare(edges[0], edges[1]));

    CHECK(!rule.getSorter()->prioritize(origin, edges).isUnique());
  }

  SECTION("Compare different") {
    auto mol = "CON"_smiles;
    CIPLabeler::CIPMol cipmol(*mol);
    Digraph g(cipmol, cipmol.getAtom(1));
    auto origin = g.getOriginalRoot();

    auto frac = origin->getAtomicNumFraction();
    REQUIRE(frac.numerator() == 8);
    REQUIRE(frac.denominator() == 1);

    Rule1a rule;

    auto edges = origin->getEdges();
    REQUIRE(edges.size() == 2);
    REQUIRE(edges[0] != edges[1]);

    auto frac0 = edges[0]->getEnd()->getAtomicNumFraction();
    REQUIRE(frac0.numerator() == 6);
    REQUIRE(frac0.denominator() == 1);

    auto frac1 = edges[1]->getEnd()->getAtomicNumFraction();
    REQUIRE(frac1.numerator() == 7);
    REQUIRE(frac1.denominator() == 1);

    CHECK(rule.compare(edges[0], edges[1]) < 0);
    CHECK(rule.compare(edges[1], edges[0]) > 0);

    CHECK(rule.getSorter()->prioritize(origin, edges).isUnique());
  }
}

TEST_CASE("Rule2", "[accurateCIP]") {
  SECTION("Compare equal") {
    auto mol = "COC"_smiles;
    CIPLabeler::CIPMol cipmol(*mol);
    Digraph g(cipmol, cipmol.getAtom(1));
    auto origin = g.getOriginalRoot();

    auto frac = origin->getAtomicNumFraction();
    REQUIRE(frac.numerator() == 8);
    REQUIRE(frac.denominator() == 1);

    Rule2 rule;

    auto edges = origin->getEdges();
    REQUIRE(edges.size() == 2);
    REQUIRE(edges[0] != edges[1]);

    CHECK(0 == rule.compare(edges[0], edges[1]));

    CHECK(!rule.getSorter()->prioritize(origin, edges).isUnique());
  }

  SECTION("Compare different: Zero Mass Num") {
    auto mol = "CO[13C]"_smiles;
    CIPLabeler::CIPMol cipmol(*mol);
    Digraph g(cipmol, cipmol.getAtom(1));
    auto origin = g.getOriginalRoot();

    auto frac = origin->getAtomicNumFraction();
    REQUIRE(frac.numerator() == 8);
    REQUIRE(frac.denominator() == 1);

    Rule2 rule;

    auto edges = origin->getEdges();
    REQUIRE(edges.size() == 2);
    REQUIRE(edges[0] != edges[1]);

    REQUIRE(edges[0]->getEnd()->getMassNum() == 0);
    REQUIRE(edges[1]->getEnd()->getMassNum() == 13);

    CHECK(rule.compare(edges[0], edges[1]) < 0);
    CHECK(rule.compare(edges[1], edges[0]) > 0);

    CHECK(rule.getSorter()->prioritize(origin, edges).isUnique());
  }

  SECTION("Compare different: Non-Zero Mass Num") {
    auto mol = "[13C]O[14C]"_smiles;
    CIPLabeler::CIPMol cipmol(*mol);
    Digraph g(cipmol, cipmol.getAtom(1));
    auto origin = g.getOriginalRoot();

    auto frac = origin->getAtomicNumFraction();
    REQUIRE(frac.numerator() == 8);
    REQUIRE(frac.denominator() == 1);

    Rule2 rule;

    auto edges = origin->getEdges();
    REQUIRE(edges.size() == 2);
    REQUIRE(edges[0] != edges[1]);

    REQUIRE(edges[0]->getEnd()->getMassNum() == 13);
    REQUIRE(edges[1]->getEnd()->getMassNum() == 14);

    CHECK(rule.compare(edges[0], edges[1]) < 0);
    CHECK(rule.compare(edges[1], edges[0]) > 0);

    CHECK(rule.getSorter()->prioritize(origin, edges).isUnique());
  }
}

TEST_CASE("Tetrahedral assignment", "[accurateCIP]") {
  auto mol = "Br[C@H](Cl)F"_smiles;
  REQUIRE(mol->getNumAtoms() == 4);

  auto chiral_atom = mol->getAtomWithIdx(1);
  chiral_atom->clearProp(common_properties::_CIPCode);
  REQUIRE(chiral_atom->getChiralTag() == Atom::CHI_TETRAHEDRAL_CCW);

  CIPLabeler::assignCIPLabels(*mol);

  std::string chirality;
  CHECK(chiral_atom->getPropIfPresent(common_properties::_CIPCode, chirality));
  CHECK(chirality == "S");
}

TEST_CASE("Double bond stereo assignment", "[accurateCIP]") {
  auto mol = R"(CC\C(\C(\C)=N\O)=N\O)"_smiles;  // VS013
  REQUIRE(mol->getNumAtoms() == 9);

  auto bond_1 = mol->getBondWithIdx(4);
  auto bond_2 = mol->getBondWithIdx(6);
  REQUIRE(bond_1->getBondType() == Bond::DOUBLE);
  REQUIRE(bond_2->getBondType() == Bond::DOUBLE);
  REQUIRE(bond_1->getStereo() == Bond::STEREOE);
  REQUIRE(bond_2->getStereo() == Bond::STEREOZ);

  CIPLabeler::assignCIPLabels(*mol);

  std::string chirality;
  CHECK(bond_1->getPropIfPresent(common_properties::_CIPCode, chirality));
  CHECK(chirality == "E");

  CHECK(bond_2->getPropIfPresent(common_properties::_CIPCode, chirality));
  CHECK(chirality == "Z");
}

TEST_CASE("phosphine and arsine chirality", "[accurateCIP]") {
  const std::vector<std::pair<std::string, std::string>> mols{
      {"C[P@](C1CCCC1)C1=CC=CC=C1", "R"},
      {"C[As@@](C1CCCC1)C1=CC=CC=C1", "S"},
      {"C[P@H]C1CCCCC1", "R"},
      {"C[P@@H]C1CCCCC1", "S"}};

  for (const auto &ref : mols) {
    std::unique_ptr<RWMol> mol{SmilesToMol(ref.first)};
    REQUIRE(mol);
    CIPLabeler::assignCIPLabels(*mol);

    std::string chirality;
    CHECK(mol->getAtomWithIdx(1)->getPropIfPresent(common_properties::_CIPCode,
                                                   chirality));
    CHECK(chirality == ref.second);
  }
}

TEST_CASE("assign specific atoms and bonds", "[accurateCIP]") {
  SECTION("Assign atoms") {
    auto mol = "C[C@H](Cl)CC[C@H](Cl)C"_smiles;
    REQUIRE(mol);

    auto atom1 = mol->getAtomWithIdx(1);
    auto atom5 = mol->getAtomWithIdx(5);

    REQUIRE(atom1->hasProp(common_properties::_CIPCode));
    REQUIRE(atom5->hasProp(common_properties::_CIPCode));

    atom1->clearProp(common_properties::_CIPCode);
    atom5->clearProp(common_properties::_CIPCode);

    boost::dynamic_bitset<> atoms(mol->getNumAtoms());
    boost::dynamic_bitset<> bonds;
    atoms.set(1);
    CIPLabeler::assignCIPLabels(*mol, atoms, bonds);

    std::string chirality;
    CHECK(atom1->getPropIfPresent(common_properties::_CIPCode, chirality));
    CHECK(chirality == "S");
    CHECK(!atom5->hasProp(common_properties::_CIPCode));
  }
  SECTION("Assign bonds") {
    auto mol = R"(C\C=C\C=C/C)"_smiles;
    REQUIRE(mol);

    auto bond1 = mol->getBondWithIdx(1);
    auto bond3 = mol->getBondWithIdx(3);

    REQUIRE(bond1->getBondType() == Bond::DOUBLE);
    REQUIRE(bond3->getBondType() == Bond::DOUBLE);

    REQUIRE(!bond1->hasProp(common_properties::_CIPCode));
    REQUIRE(!bond3->hasProp(common_properties::_CIPCode));

    boost::dynamic_bitset<> atoms;
    boost::dynamic_bitset<> bonds(mol->getNumBonds());
    bonds.set(3);
    CIPLabeler::assignCIPLabels(*mol, atoms, bonds);

    std::string stereo;
    CHECK(!bond1->hasProp(common_properties::_CIPCode));
    CHECK(bond3->getPropIfPresent(common_properties::_CIPCode, stereo));
    CHECK(stereo == "Z");
  }
}

TEST_CASE("para-stereochemistry", "[accurateCIP]") {
  SECTION("example 1") {
    // slightly simplified complex example from Salome Rieder
    auto mol = "C\\C=C/[C@@H](\\C=C\\O)[C@H](C)[C@H](\\C=C/C)\\C=C\\O"_smiles;
    REQUIRE(mol);
    CIPLabeler::assignCIPLabels(*mol);

    std::string chirality;
    CHECK(mol->getAtomWithIdx(3)->getPropIfPresent(common_properties::_CIPCode,
                                                   chirality));
    CHECK(chirality == "R");
    CHECK(mol->getAtomWithIdx(7)->getPropIfPresent(common_properties::_CIPCode,
                                                   chirality));
    CHECK(chirality == "r");
    CHECK(mol->getAtomWithIdx(9)->getPropIfPresent(common_properties::_CIPCode,
                                                   chirality));
    CHECK(chirality == "S");
  }
  SECTION("example 2") {
    // lovely complex example from Salome Rieder
    auto mol = "C\\C=C/[C@@H](\\C=C\\C)[C@H](C)[C@H](\\C=C/C)\\C=C\\C"_smiles;
    REQUIRE(mol);
    CIPLabeler::assignCIPLabels(*mol);

    std::string chirality;
    CHECK(mol->getAtomWithIdx(3)->getPropIfPresent(common_properties::_CIPCode,
                                                   chirality));
    CHECK(chirality == "R");
    CHECK(mol->getAtomWithIdx(7)->getPropIfPresent(common_properties::_CIPCode,
                                                   chirality));
    CHECK(chirality == "r");
    CHECK(mol->getAtomWithIdx(9)->getPropIfPresent(common_properties::_CIPCode,
                                                   chirality));
    CHECK(chirality == "S");
  }
}

TEST_CASE(
    "Github #4996: Bad handling of dummy atoms in the CIP assignment code",
    "[accurateCIP]") {
  SECTION("case 1") {
    auto m = "*[C@](F)(Cl)Br"_smiles;
    REQUIRE(m);
    bool cleanit = true;
    bool force = true;
    // original assignment:
    MolOps::assignStereochemistry(*m, cleanit, force);
    std::string cip;
    CHECK(m->getAtomWithIdx(1)->getPropIfPresent(common_properties::_CIPCode,
                                                 cip));
    CHECK(cip == "S");

    m->getAtomWithIdx(1)->clearProp(common_properties::_CIPCode);
    CIPLabeler::assignCIPLabels(*m);
    CHECK(m->getAtomWithIdx(1)->getPropIfPresent(common_properties::_CIPCode,
                                                 cip));
    CHECK(cip == "S");
  }
  SECTION("dummies can match dummies") {
    auto m = "*[C@](*)(Cl)Br"_smiles;
    REQUIRE(m);
    bool cleanit = true;
    bool force = true;
    // original assignment:
    MolOps::assignStereochemistry(*m, cleanit, force);
    CHECK(!m->getAtomWithIdx(1)->hasProp(common_properties::_CIPCode));

    CIPLabeler::assignCIPLabels(*m);
    CHECK(!m->getAtomWithIdx(1)->hasProp(common_properties::_CIPCode));
  }
  SECTION("case 2") {
    auto m = "C1CC[C@](*)2CCCC[C@H]2C1"_smiles;
    REQUIRE(m);

    bool cleanit = true;
    bool force = true;
    // original assignment doesn't work for these:
    MolOps::assignStereochemistry(*m, cleanit, force);
    CHECK(!m->getAtomWithIdx(3)->hasProp(common_properties::_CIPCode));
    CHECK(!m->getAtomWithIdx(9)->hasProp(common_properties::_CIPCode));

    CIPLabeler::assignCIPLabels(*m);
    std::string cip;
    CHECK(m->getAtomWithIdx(3)->getPropIfPresent(common_properties::_CIPCode,
                                                 cip));
    CHECK(cip == "s");
    cip = "";
    CHECK(m->getAtomWithIdx(9)->getPropIfPresent(common_properties::_CIPCode,
                                                 cip));
    CHECK(cip == "s");
  }
}

TEST_CASE("CIP code errors on fragments which cannot be kekulized",
          "[accurateCIP]") {
  SECTION("fragment not affecting the stereochem") {
    auto m = "F[C@H](CNC)CCc(:c):c"_smarts;
    m->getAtomWithIdx(1)->clearProp(common_properties::_CIPCode);
    m->updatePropertyCache();
    CIPLabeler::assignCIPLabels(*m);
    std::string cip;
    CHECK(m->getAtomWithIdx(1)->getPropIfPresent(common_properties::_CIPCode,
                                                 cip));
    CHECK(cip == "S");
  }
  SECTION("fragment, unique bits") {
    auto m = "F[C@H](C(N)C)c(:c):c"_smarts;
    m->getAtomWithIdx(1)->clearProp(common_properties::_CIPCode);
    m->updatePropertyCache();
    CIPLabeler::assignCIPLabels(*m);
    std::string cip;
    CHECK(m->getAtomWithIdx(1)->getPropIfPresent(common_properties::_CIPCode,
                                                 cip));
  }
  SECTION("fragment, non-unique bits") {
    auto m = "F[C@H]([C]([NH])[CH2])c(:n):c"_smarts;
    m->getAtomWithIdx(1)->clearProp(common_properties::_CIPCode);
    m->updatePropertyCache();
    CIPLabeler::assignCIPLabels(*m);
    std::string cip;
    CHECK(!m->getAtomWithIdx(1)->getPropIfPresent(common_properties::_CIPCode,
                                                  cip));
  }
}

TEST_CASE("GitHub Issue #5142", "[bug][accurateCIP]") {
  auto mol = "*C1C[C@H](CCC)[C@@H](C)[C@H](C)C1"_smiles;
  REQUIRE(mol);
  CIPLabeler::assignCIPLabels(*mol);
}

TEST_CASE("CIP timeout test", "[accurateCIP]") {
  std::string molBlock = R"(
  Mrv2117 11112217353D          

 40 50  0  0  0  0            999 V2000
    7.5483   -7.7451   -3.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3984   -5.8792   -3.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3399   -6.5425   -1.9898 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6820   -3.9425   -1.6474 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8163   -7.1034   -1.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5722   -4.7343   -0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1701   -7.2380   -0.8890 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8300   -6.9765   -2.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6631   -7.1690   -1.5375 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.4077   -9.5239   -2.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9006  -10.0139    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6600   -8.8749    0.2914 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5136   -5.9115   -0.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5338   -7.8406    1.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6981   -8.8654    3.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4046  -10.6907    1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3185   -9.3106    0.9700 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4958  -10.8075   -0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5552   -7.8780    2.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8522   -9.1147    0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1601   -8.2997    0.2353 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5774   -7.5989    1.5700 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6577   -4.0099    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0808   -6.4894   -0.1982 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9123   -5.4699   -0.9424 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9155   -8.2329    2.0184 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0766   -7.5513    0.9147 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6780   -6.9857    3.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5861   -5.8939   -0.2667 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9973   -5.0597    1.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3193   -5.8429    1.5048 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4740   -4.7173    2.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9809   -7.1457    1.9811 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8270   -6.1245    1.2483 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0023   -5.4308    0.1366 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9125   -8.9385   -1.4737 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2374   -9.3522   -0.1173 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4116   -8.6461   -1.2148 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7726   -9.9758   -2.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2577   -7.6250   -1.9478 C   0  0  2  0  0  0  0  0  0  0  0  0
  1 40  1  0  0  0  0
  2  3  1  0  0  0  0
  3  9  1  0  0  0  0
  3 25  1  0  0  0  0
  3 40  1  0  0  0  0
  4 25  1  0  0  0  0
  5  7  1  0  0  0  0
  6 29  1  0  0  0  0
  7 21  1  0  0  0  0
  7 29  1  0  0  0  0
  7 40  1  0  0  0  0
  8  9  1  0  0  0  0
  9 24  1  0  0  0  0
  9 38  1  0  0  0  0
 10 38  1  0  0  0  0
 11 12  1  0  0  0  0
 12 17  1  0  0  0  0
 12 27  1  0  0  0  0
 12 38  1  0  0  0  0
 13 24  1  0  0  0  0
 14 27  1  0  0  0  0
 15 26  1  0  0  0  0
 16 17  1  0  0  0  0
 17 26  1  0  0  0  0
 17 37  1  0  0  0  0
 18 37  1  0  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 37  1  0  0  0  0
 22 26  1  0  0  0  0
 22 34  1  0  0  0  0
 23 35  1  0  0  0  0
 24 27  1  0  0  0  0
 24 35  1  0  0  0  0
 25 29  1  0  0  0  0
 25 35  1  0  0  0  0
 26 33  1  0  0  0  0
 27 33  1  0  0  0  0
 28 33  1  0  0  0  0
 29 34  1  0  0  0  0
 30 34  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 35  1  0  0  0  0
 31 34  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 36 40  1  0  0  0  0
M  END

  )";

  auto mol =
      std::unique_ptr<RDKit::RWMol>(MolBlockToMol(molBlock, true, false));
  REQUIRE(mol);
  CHECK_THROWS_AS(CIPLabeler::assignCIPLabels(*mol, 100000),
                  CIPLabeler::MaxIterationsExceeded);

  // try a second call to test that the timer is reset

  CHECK_THROWS_AS(CIPLabeler::assignCIPLabels(*mol, 100000),
                  CIPLabeler::MaxIterationsExceeded);
}
