Crystal structure of dimethyl 4,4′-(((1R, 2R)-cyclohexane-1,2-diyl)bis(azanediyl))dibenzoate, C22H26N2O4
Pan, Ting; Shi, Da-Bin; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 265–267; doi:10.1515/ncrs-2023-0008

data_8107413
_publ_section_title
;
 Crystal structure of dimethyl 4,4&#x2032;-(((1R,
 2R)-cyclohexane-1,2-diyl)bis(azanediyl))dibenzoate, C22H26N2O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              265
_journal_page_last               267
_journal_paper_doi               10.1515/ncrs-2023-0008
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H26 N2 O4'
_chemical_formula_sum            'C22 H26 N2 O4'
_chemical_formula_weight         382.45
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_Hall           'P 32'
_space_group_name_H-M_alt        'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   8.0196(2)
_cell_length_b                   8.0196(2)
_cell_length_c                   26.2366(5)
_cell_measurement_reflns_used    4940
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.8640
_cell_measurement_theta_min      3.3300
_cell_volume                     1461.31(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    'SHELXS  (Sheldrick, 2008)'
_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 0.985
_diffrn_measured_fraction_theta_max 0.968
_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   -129.00  47.00   1.00    1.00    --  -40.73   0.00 120.00  176
  2  \w     23.00  97.00   1.00    1.00    --   40.73-125.00 120.00   74
  3  \w     16.00  88.00   1.00    1.00    --   40.73  38.00-180.00   72
  4  \w    114.00 149.00   1.00    1.00    --  108.20 125.00-150.00   35
  5  \w     89.00 115.00   1.00    1.00    --  108.20-125.00 -60.00   26
  6  \w    100.00 173.00   1.00    1.00    --  108.20  87.00-110.00   73
  7  \w     83.00 156.00   1.00    1.00    --  108.20  77.00  90.00   73
  8  \w     79.00 108.00   1.00    1.00    --  108.20  61.00 120.00   29
  9  \w    150.00 176.00   1.00    1.00    --  108.20  61.00 120.00   26
 10  \w    122.00 162.00   1.00    1.00    --  108.20 125.00-180.00   40
 11  \w     97.00 173.00   1.00    1.00    --  108.20 125.00  30.00   76
 12  \w     93.00 143.00   1.00    1.00    --  108.20  45.00 150.00   50
;
_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      0.1697217000
_diffrn_orient_matrix_UB_12      0.1730364000
_diffrn_orient_matrix_UB_13      0.0265192000
_diffrn_orient_matrix_UB_21      0.1421782000
_diffrn_orient_matrix_UB_22      -0.0221793000
_diffrn_orient_matrix_UB_23      -0.0348807000
_diffrn_orient_matrix_UB_31      -0.0115191000
_diffrn_orient_matrix_UB_32      0.1374098000
_diffrn_orient_matrix_UB_33      -0.0390650000
_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  0.0187
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6388
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.926
_diffrn_reflns_theta_min         5.057
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84319
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_coef       0.0057(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0520P)^2^+0.1101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.870
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                3451
_reflns_number_total             3533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0008_suppl.cif
_cod_data_source_block           s-109_2
_cod_original_cell_volume        1461.31(8)
_cod_database_code               8107413
_reflns_odcompleteness_completeness 98.48
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C5(H5), C6(H6), C14(H14), C15(H15), C17(H17),
  C18(H18)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              51091
_shelx_hkl_checksum              76553
_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 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.616