The Synthesis of Multisubstituted Pyrroles via a Copper-Catalyzed Tandem Three-Component Reaction.
Mou, Xue-Qing; Xu, Zheng-Liang; Xu, Li; Wang, Shao-Hua; Zhang, Bang-Hong; Zhang, Di; Wang, Jie; Liu, Wei-Ting; Bao, Wen; Organic letters 18 (2016) 4032–4035; doi:10.1021/acs.orglett.6b01883

data_1555662
_publ_section_title
;
 The Synthesis of Multisubstituted Pyrroles via a Copper-Catalyzed Tandem
 Three-Component Reaction.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4032
_journal_page_last               4035
_journal_paper_doi               10.1021/acs.orglett.6b01883
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C19 H13 Cl N2'
_chemical_formula_sum            'C19 H13 Cl N2'
_chemical_formula_weight         304.77
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                92.244(18)
_cell_angle_beta                 94.916(16)
_cell_angle_gamma                98.110(18)
_cell_formula_units_Z            2
_cell_length_a                   4.0802(8)
_cell_length_b                   11.717(3)
_cell_length_c                   15.719(3)
_cell_measurement_reflns_used    933
_cell_measurement_temperature    293.64(10)
_cell_measurement_theta_max      23.7680
_cell_measurement_theta_min      3.8060
_cell_volume                     740.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.64(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   32.00   76.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000  150.0000 22

  2 omega   -1.00   33.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000    0.0000 17

  3 omega  -42.00   34.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  -30.0000 38

  4 omega  -19.00   53.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000   90.0000 36

  5 omega   -8.00   24.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  120.0000 16

  6 omega  -47.00   35.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000 -150.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0355915000
_diffrn_orient_matrix_UB_12      0.0599203000
_diffrn_orient_matrix_UB_13      0.0114160000
_diffrn_orient_matrix_UB_21      -0.0094828000
_diffrn_orient_matrix_UB_22      0.0123280000
_diffrn_orient_matrix_UB_23      -0.0438884000
_diffrn_orient_matrix_UB_31      -0.1724550000
_diffrn_orient_matrix_UB_32      0.0026056000
_diffrn_orient_matrix_UB_33      0.0004934000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4531
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_min         3.518
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0350P)^2^+0.2026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1821
_reflns_number_total             2895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01883_si_002.cif
_cod_data_source_block           wangshh0603
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C12.67 H8.67 Cl0.67 N1.33'
_cod_original_formula_weight         203.18
_cod_original_formula_moiety         '0.67(C19 H13 Cl N2)'
_cod_original_formula_units_Z            3
_cod_database_code               1555662
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3), C10(H10), C2AA(H2AA), C14(H14), C16(H16),
 C15(H15)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-03
_olex2_submission_special_instructions 'No special instructions were received'