A one-pot telescopic synthesis of benzo[<i>b</i>]carbazoles and exploration of their liquid crystalline properties.
Malik, Nirmal; De, Ritobrata; Pal, Santanu Kumar; Ramasastry, S. S. V.; Chemical communications (Cambridge, England) 60 (2024) 4797–4800; doi:10.1039/d4cc00721b

data_7132927
_publ_section_title
;
 A one-pot telescopic synthesis of benzo[<i>b</i>]carbazoles and
 exploration of their liquid crystalline properties.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4797
_journal_page_last               4800
_journal_paper_doi               10.1039/d4cc00721b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C35 H25 N O2 S'
_chemical_formula_sum            'C35 H25 N O2 S'
_chemical_formula_weight         523.660
_chemical_name_systematic        NM-01-177
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-28
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-27 deposited with the CCDC.	2024-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                81.330(2)
_cell_angle_beta                 88.876(2)
_cell_angle_gamma                74.316(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8511(3)
_cell_length_b                   10.7751(3)
_cell_length_c                   14.2389(4)
_cell_measurement_reflns_used    9434
_cell_measurement_temperature    298
_cell_measurement_theta_max      32.2790
_cell_measurement_theta_min      3.1290
_cell_volume                     1292.16(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9364
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -69.00 119.00   0.50   10.00    --   29.89  54.00   0.00  376
  2  \w    -69.00 119.00   0.50   10.00    --   29.89  54.00-150.00  376
  3  \w    -69.00 119.00   0.50   10.00    --   29.89  54.00-150.00  376
  4  \w    -69.00 119.00   0.50   10.00    --   29.89  54.00 120.00  376
  5  \w    -69.00  58.00   0.50   10.00    --   29.89  54.00 -60.00  254
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0348864000
_diffrn_orient_matrix_UB_12      0.0333517000
_diffrn_orient_matrix_UB_13      0.0288787000
_diffrn_orient_matrix_UB_21      -0.0402989000
_diffrn_orient_matrix_UB_22      0.0604305000
_diffrn_orient_matrix_UB_23      -0.0269705000
_diffrn_orient_matrix_UB_31      -0.0639578000
_diffrn_orient_matrix_UB_32      0.0044732000
_diffrn_orient_matrix_UB_33      0.0312891000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9364
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28604
_diffrn_reflns_point_group_measured_fraction_full 0.9989
_diffrn_reflns_point_group_measured_fraction_max 0.9364
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         32.64
_diffrn_reflns_theta_min         2.63
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             548.550
_exptl_crystal_preparation       ACN
_exptl_crystal_recrystallization_method ACN
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.3057
_refine_diff_density_min         -0.5214
_refine_diff_density_rms         0.0742
_refine_ls_d_res_high            0.6589
_refine_ls_d_res_low             7.7492
_refine_ls_goodness_of_fit_ref   1.0481
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     353
_refine_ls_number_reflns         8863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0481
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0970P)^2^+0.2658P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1768
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              16
_reflns_limit_k_min              -14
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                6834
_reflns_number_total             8863
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc00721b2.cif
_cod_data_source_block           NIRMALCARBAZOLE
_cod_depositor_comments          'Adding full bibliography for 7132927.cif.'
_cod_database_code               7132927
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J), C00L(H00L),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012)
2.b Idealised Me refined as rotating group:
 C013(H01a,H01b,H01c)
;
_olex2_submission_original_sample_id NM-01-177
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.497
_oxdiff_exptl_absorpt_empirical_full_min 0.588