General Synthesis of Unsymmetrical 3,3'-(Aza)diindolylmethane Derivatives.
Pillaiyar, Thanigaimalai; Gorska, Ewelina; Schnakenburg, Gregor; Müller, Christa E; The Journal of organic chemistry 83 (2018) 9902–9913; doi:10.1021/acs.joc.8b01349

data_4035106
_publ_section_title
;
 General Synthesis of Unsymmetrical 3,3'-(Aza)diindolylmethane
 Derivatives.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9902
_journal_page_last               9913
_journal_paper_doi               10.1021/acs.joc.8b01349
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H15 N3 O'
_chemical_formula_sum            'C17 H15 N3 O'
_chemical_formula_weight         277.32
_chemical_name_systematic        yazh-121D
_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     direct
_audit_creation_date             2017-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1864(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.8369(4)
_cell_length_b                   7.1622(2)
_cell_length_c                   23.2165(5)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.14
_cell_measurement_theta_min      4.01
_cell_volume                     2817.78(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'fine slicing \w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            41867
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.739
_diffrn_reflns_theta_min         2.607
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3299
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1462 before and 0.0824 after correction. The Ratio of minimum to maximum transmission is 0.4378. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0429P)^2^+1.5391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4596
_reflns_number_total             5088
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01349_si_002.cif
_cod_data_source_block           12c
_cod_database_code               4035106
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.878
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10'(H10C,H10D)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C6(H6), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), N1'(H1'), C2'(H2'), C5'(H5'), C6'(H6'), C9'(H9'),
 C13'(H13'), C14'(H14'), C15'(H15'), C16'(H16'), C17'(H17')
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C7'(H7'A,H7'B,H7'C)
;
_shelx_res_checksum              82924
_shelx_hkl_checksum              71491
_olex2_submission_special_instructions 'No special instructions were received'