Chemodivergent synthesis of multi-substituted/fused pyrroles via copper-catalyzed carbene cascade reaction of propargyl α-iminodiazoacetates.
Zhang, Cheng; Chang, Sailan; Qiu, Lihua; Xu, Xinfang; Chemical communications (Cambridge, England) 52 (2016) 12470–12473; doi:10.1039/c6cc06864b

data_7125105
_publ_section_title
;
 Chemodivergent synthesis of multi-substituted/fused pyrroles via
 copper-catalyzed carbene cascade reaction of propargyl
 \a-iminodiazoacetates.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12470
_journal_page_last               12473
_journal_paper_doi               10.1039/c6cc06864b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C20 H16 Br N O3'
_chemical_formula_sum            'C20 H16 Br N O3'
_chemical_formula_weight         398.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-15 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.213(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.2880(5)
_cell_length_b                   27.2739(16)
_cell_length_c                   14.6976(9)
_cell_measurement_reflns_used    1629
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      28.5230
_cell_measurement_theta_min      3.2880
_cell_volume                     1718.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.879
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_details
;
  1 omega   39.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514   37.0000  -90.0000 35

  2 omega    4.00   30.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       13.6514   37.0000  -90.0000 26

  3 omega  -86.00  -61.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327 -178.0000 -120.0000 25

  4 omega  -59.00   14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.4327  -57.0000  120.0000 73
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1285201000
_diffrn_orient_matrix_UB_12      -0.0017823000
_diffrn_orient_matrix_UB_13      -0.0300404000
_diffrn_orient_matrix_UB_21      -0.1002098000
_diffrn_orient_matrix_UB_22      -0.0093577000
_diffrn_orient_matrix_UB_23      -0.0343916000
_diffrn_orient_matrix_UB_31      -0.0292885000
_diffrn_orient_matrix_UB_32      0.0241861000
_diffrn_orient_matrix_UB_33      -0.0155342000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6334
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.77
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                2200
_reflns_number_total             3104
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc06864b2.cif
_cod_data_source_block           g160613c
_cod_database_code               7125105
_chemical_oxdiff_formula         'C H O N Br'
_reflns_odcompleteness_completeness 86.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'