Crystal structure of 6,6′-((1E, 1′E)-(((1R, 2R)-1,2-diphenylethane-1,2-diyl) bis(azanylylidene))bis(methanylylidene))bis(2-ethylphenol), C32H32N2O2
Xu, Zeng-Bing; He, Jing-Yuan; Shi, Da-Bin; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 731–733; doi:10.1515/ncrs-2021-0060

data_8104695
_publ_section_title
;
 Crystal structure of 6,6&#x2032;-((1E, 1&#x2032;E)-(((1R,
 2R)-1,2-diphenylethane-1,2-diyl)
 bis(azanylylidene))bis(methanylylidene))bis(2-ethylphenol), C32H32N2O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              731
_journal_page_last               733
_journal_paper_doi               10.1515/ncrs-2021-0060
_journal_volume                  236
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H32 N2 O2'
_chemical_formula_sum            'C32 H32 N2 O2'
_chemical_formula_weight         476.59
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.78920(12)
_cell_length_b                   12.71913(14)
_cell_length_c                   20.9423(3)
_cell_measurement_reflns_used    10429
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6200
_cell_measurement_theta_min      2.1160
_cell_volume                     2607.53(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -65.00  34.00   1.00    1.00    --  -40.73  37.00-140.00   99
  2  \w    -65.00  34.00   1.00    1.00    --  -40.73  37.00 120.00   99
  3  \w     23.00  97.00   1.00    1.00    --   40.73-125.00  90.00   74
  4  \w     23.00  97.00   1.00    1.00    --   40.73-125.00-120.00   74
  5  \w     94.00 178.00   1.00    1.00    --  107.58 125.00  90.00   84
  6  \w     25.00 109.00   1.00    1.00    --  107.58 -94.00  30.00   84
  7  \w     34.00 122.00   1.00    1.00    --  107.58-125.00-120.00   88
  8  \w     98.00 178.00   1.00    1.00    --  107.58  86.00   3.00   80
  9  \w     35.00 160.00   1.00    1.00    --  107.58 -15.00  30.00  125
 10  \w   -116.00 -73.00   1.00    1.00    --  -40.98-156.00-160.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0574461000
_diffrn_orient_matrix_UB_12      -0.0949346000
_diffrn_orient_matrix_UB_13      0.0369623000
_diffrn_orient_matrix_UB_21      -0.0454629000
_diffrn_orient_matrix_UB_22      -0.0737016000
_diffrn_orient_matrix_UB_23      -0.0543770000
_diffrn_orient_matrix_UB_31      0.1393027000
_diffrn_orient_matrix_UB_32      0.0150662000
_diffrn_orient_matrix_UB_33      -0.0329647000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12561
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.751
_diffrn_reflns_theta_min         4.066
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 2090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5133
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0779P)^2^+0.9741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                5044
_reflns_number_total             5133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0060_suppl.cif
_cod_data_source_block           sdb-84
_cod_original_cell_volume        2607.53(5)
_cod_database_code               8104695
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.927
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2. Rigid bond restraints
 C18, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C18 \\sim C22: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
4.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C31(H31A,H31B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C24(H24), C26(H26),
  C27(H27), C28(H28)
4.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C32(H32A,H32B,H32C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;