NHC as the Guiding Factor in a Copper-Catalyzed Intramolecular C Arylation of Pyrrolylimidazolium Salts: Synthesis of Luminescent Heterotetracyclic Frameworks.
Tomashenko, Olesya A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; The Journal of organic chemistry 82 (2017) 616–623; doi:10.1021/acs.joc.6b02627

data_4032241
_publ_section_title
;
 NHC as the Guiding Factor in a Copper-Catalyzed Intramolecular C
 Arylation of Pyrrolylimidazolium Salts: Synthesis of Luminescent
 Heterotetracyclic Frameworks.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              616
_journal_page_last               623
_journal_paper_doi               10.1021/acs.joc.6b02627
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         '0.5(H2 O), C32 H23 N3'
_chemical_formula_sum            'C32 H24 N3 O0.5'
_chemical_formula_weight         458.54
_chemical_name_systematic
7-benzyl-2,3-diphenyl-7H-imidazo[2,1-a]pyrrolo[3,2-c]isoquinoline
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.831(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6688(4)
_cell_length_b                   21.5451(7)
_cell_length_c                   16.0285(3)
_cell_measurement_reflns_used    11138
_cell_measurement_temperature    100
_cell_measurement_theta_max      75.8560
_cell_measurement_theta_min      3.4130
_cell_volume                     4719.8(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31247
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.429
_diffrn_reflns_theta_min         3.437
_exptl_absorpt_coefficient_mu    0.604
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       prism
_exptl_crystal_F_000             1928
_exptl_crystal_preparation       'see experimental part'
_exptl_crystal_recrystallization_method
'was obtained by slow evaporation from the mixture of DCM and hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     643
_refine_ls_number_reflns         9811
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+2.1711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8418
_reflns_number_total             9811
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02627_si_002.cif
_cod_data_source_block           2_ole089_sq
_cod_depositor_comments
;

2020-04-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'H2 O, 2(C32 H23 N3)'
_cod_original_formula_sum        'C64 H48 N6 O'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     917.08
_cod_database_code               4032241
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1c,H1d)
2.b Secondary CH2 refined with riding coordinates:
 C18A(H18c,H18d), C18B(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C30B(H30B), C5A(H5A), C10A(H10A), C27B(H27B), C10B(H10B), C16A(H16A),
 C17A(H17A), C14B(H14B), C28B(H28B), C29B(H29B), C11B(H11B), C30A(H30A),
 C16B(H16B), C20B(H20B), C27A(H27A), C4A(H4A), C11A(H11A), C1A(H1A), C13B(H13B),
  C24A(H24A), C14A(H14A), C29A(H29A), C13A(H13A), C1B(H1B), C12B(H12B),
 C3A(H3A), C2A(H2A), C21B(H21B), C12A(H12A), C17B(H17B), C22B(H22B), C28A(H28A),
  C20A(H20A), C22A(H22A), C23A(H23A), C5B(H5B), C21A(H21A), C2B(H2B),
 C24B(H24B), C3B(H3B), C4B(H4B), C23B(H23B)
;
_shelx_res_checksum              29538
_shelx_hkl_checksum              56807
_shelx_fab_checksum              42699
_olex2_submission_special_instructions 'No special instructions were received'