Synthesis of benzo[a]carbazoles and indolo[2,3-a]carbazoles via photoinduced carbene-mediated C‒H insertion reaction
Yang, Jidong; Zhang, Qingzhao; Zhang, Wei; Yu, Wei; RSC Adv. 4 (2014) 13704–; doi:10.1039/C4RA00442F

data_7235480
_publ_section_title
;
 Synthesis of benzo[a]carbazoles and indolo[2,3-a]carbazoles via
 photoinduced carbene-mediated C--H insertion reaction
;
_journal_issue                   26
_journal_name_full               'RSC Adv.'
_journal_page_first              13704
_journal_paper_doi               10.1039/C4RA00442F
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C20 H16 Br N O3'
_chemical_formula_sum            'C20 H17.25 Br N O3'
_chemical_formula_weight         399.51
_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     iterative
_audit_creation_date             2013-06-19
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.334(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3664(6)
_cell_length_b                   14.1501(6)
_cell_length_c                   17.8928(8)
_cell_measurement_reflns_used    3045
_cell_measurement_temperature    293.1(7)
_cell_measurement_theta_max      23.7460
_cell_measurement_theta_min      3.6400
_cell_volume                     3364.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293.1(7)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.8954
_diffrn_measurement_details
;
  1 omega -102.00  -76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2137  178.0000  150.0000 26

  2 omega  -11.00   95.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   77.0000  150.0000 106

  3 omega  -43.00   -2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -77.0000  -30.0000 41

  4 omega    8.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -77.0000  -30.0000 26

  5 omega  -47.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000   30.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0491070000
_diffrn_orient_matrix_UB_12      0.0180950000
_diffrn_orient_matrix_UB_13      0.0090880000
_diffrn_orient_matrix_UB_21      0.0172717000
_diffrn_orient_matrix_UB_22      -0.0460637000
_diffrn_orient_matrix_UB_23      -0.0036388000
_diffrn_orient_matrix_UB_31      -0.0116190000
_diffrn_orient_matrix_UB_32      0.0079258000
_diffrn_orient_matrix_UB_33      -0.0417557000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.118
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.463
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       block
_exptl_crystal_F_000             1626
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.00184(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         6620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0223P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             6620
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra00442f2.cif
_cod_data_source_block           yangjd0618
_cod_database_code               7235480
_reflns_odcompleteness_completeness 99.76
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C39(H39A,H39B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C22(H22),
 C23(H23), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C37(H37A,H37B,H37C), C40(H40A,H40B,
 H40C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_hkl_checksum              42646
_shelx_res_checksum              50485
_shelxl_version_number           2013-2