One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations.
Jash, Moumita; Das, Bimolendu; Chowdhury, Chinmay; The Journal of organic chemistry 81 (2016) 10987–10999; doi:10.1021/acs.joc.6b02022

data_4037334
_publ_section_title
;
 One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero-
 and Carboannulations.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10987
_journal_page_last               10999
_journal_paper_doi               10.1021/acs.joc.6b02022
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C24 H20 N2 O2 S'
_chemical_formula_sum            'C24 H20 N2 O2 S'
_chemical_formula_weight         400.48
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.551(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.462(2)
_cell_length_b                   16.120(5)
_cell_length_c                   14.655(4)
_cell_measurement_reflns_used    5491
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.273
_cell_measurement_theta_min      2.407
_cell_volume                     1999.0(10)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24404
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.238
_diffrn_reflns_theta_min         1.878
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0871 before and 0.0723 after correction.
The Ratio of minimum to maximum transmission is 0.8743.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear pinkish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0017(8)
_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   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0599P)^2^+0.2439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2858
_reflns_number_total             4384
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            5b.cif.cif
_cod_data_source_block           cc_mj3_10_0m
_cod_database_code               4037334
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.907
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N006(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R)
2.c Idealised Me refined as rotating group:
 C00S(H00D,H00E,H00F), C00T(H00O,H00S,H00T)
;
_shelx_res_checksum              88480
_shelx_hkl_checksum              10683
_olex2_submission_special_instructions 'No special instructions were received'