Synthesis of 4-Hydroxycarbazole Derivatives by Benzannulation of 3-Nitroindoles with Alkylidene Azlactones
Cao, Dongdong; Chen, Gang; Chen, Dingben; Xia, Zhijun; Li, Zongyang; Wang, Yi; Xu, Dongqing; Yang, Jianguo; ACS Omega  (2021) –; doi:10.1021/acsomega.1c01992

data_4518832
_publ_section_title
;
 Synthesis of 4-Hydroxycarbazole Derivatives by Benzannulation of
 3-Nitroindoles with Alkylidene Azlactones
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.1c01992
_journal_year                    2021
_chemical_formula_moiety         'C32 H24 N2 O4 S'
_chemical_formula_sum            'C32 H24 N2 O4 S'
_chemical_formula_weight         532.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.2810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9312(9)
_cell_length_b                   7.1744(3)
_cell_length_c                   20.7067(9)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    293.34
_cell_measurement_theta_max      27.263
_cell_measurement_theta_min      2.471
_cell_volume                     2583.4(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.34
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5037
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.471
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1496 before and 0.0649 after correction.
The Ratio of minimum to maximum transmission is 0.9109.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0629
_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^)+(0.0630P)^2^+1.8025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4160
_reflns_number_total             5037
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao1c01992_si_002.cif
_cod_data_source_block           mo_d8v20822_0m_tw
_cod_database_code               4518832
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.828(3)
 0.172(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C27(H27), C28(H28), C30(H30), C31(H31)
3.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              61461
_shelx_hkl_checksum              71075
_olex2_submission_special_instructions 'No special instructions were received'