Three-Component Cascade Synthesis of Carbazoles through [1s,6s] Sigmatropic Shift under Metal-Free Conditions.
Chen, Shanping; Jiang, Pingyu; Wang, Pu; Pei, Yong; Huang, Huawen; Xiao, Fuhong; Deng, Guo-Jun; The Journal of organic chemistry 84 (2019) 3121–3131; doi:10.1021/acs.joc.8b02994

data_4033929
_publ_section_title
;
 Three-Component Cascade Synthesis of Carbazoles through [1s,6s]
 Sigmatropic Shift under Metal-Free Conditions.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3121
_journal_page_last               3131
_journal_paper_doi               10.1021/acs.joc.8b02994
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C29 H25 N O2'
_chemical_formula_sum            'C29 H25 N O2'
_chemical_formula_weight         419.50
_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     dual
_audit_creation_date             2016-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.269(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.950(4)
_cell_length_b                   11.207(3)
_cell_length_c                   15.265(5)
_cell_measurement_reflns_used    5446
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4772
_cell_measurement_theta_min      1.4415
_cell_volume                     2208.5(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9392
	          2theta: -20.4555
scan:
	Number of images: 300
	           Slice: -107.0000 - 43.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9392
	          2theta: -20.4555
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0074
_diffrn_orient_matrix_UB_12      -0.0140
_diffrn_orient_matrix_UB_13      -0.0758
_diffrn_orient_matrix_UB_21      -0.0854
_diffrn_orient_matrix_UB_22      -0.0255
_diffrn_orient_matrix_UB_23      -0.0036
_diffrn_orient_matrix_UB_31      -0.0153
_diffrn_orient_matrix_UB_32      0.0568
_diffrn_orient_matrix_UB_33      -0.0394
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13391
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.193
_diffrn_reflns_theta_max         25.193
_diffrn_reflns_theta_min         1.577
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.231
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0886
_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^)+(0.0290P)^2^+1.8291P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3017
_reflns_number_total             3968
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02994_si_001.cif
_cod_data_source_block           mx5262
_cod_database_code               4033929
_diffrn_number_total             5286
_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
2.a Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C14(H14), C15(H15), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              73717
_shelx_hkl_checksum              10762
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'