#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:40:32 +0100 (Tue 04 de Mar de 2025) $
#$Revision: 298179 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/98/7249837.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249837
loop_
_publ_author_name
'Qi, Ying'
'Liu, Yang'
'Li, Xia'
'Xu, Juan'
'Zhang, Qi'
_publ_section_title
;
 Innovative aminoglutethimide co-crystals: synthesis, characterization,
 and insights into molecular interactions
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1146
_journal_page_last               1156
_journal_paper_doi               10.1039/D4CE01171F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_sum            'C21 H24 N2 O4'
_chemical_formula_weight         368.42
_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_method           SHELXL-2018/3
_audit_update_record
;
2024-06-19 deposited with the CCDC.	2024-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.367(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.904(5)
_cell_length_b                   6.4769(17)
_cell_length_c                   17.825(5)
_cell_measurement_temperature    296(2)
_cell_volume                     1913.3(9)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0954
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15100
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        23.629
_diffrn_reflns_theta_max         23.629
_diffrn_reflns_theta_min         1.853
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0835
_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/[σ²(Fo²)+(0.1099P)²+3.3133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2188
_refine_ls_wR_factor_ref         0.2499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1752
_reflns_number_total             2822
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce01171f2.cif
_cod_data_source_block           1_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7249835--7249837.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7249837
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.982
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4677(2) 0.5188(6) 0.6302(2) 0.0467(10) Uani 1 1 d . . . . .
H1 H 0.441523 0.446884 0.654300 0.070 Uiso 1 1 calc R U . . .
O2 O 0.4429(2) 0.8151(6) 0.5692(2) 0.0438(10) Uani 1 1 d . . . . .
O3 O 0.9124(3) 0.6035(6) 0.8786(2) 0.0553(11) Uani 1 1 d . . . . .
N2 N 0.5631(2) 0.7711(6) 0.4860(2) 0.0340(10) Uani 1 1 d . . . . .
H2A H 0.524053 0.684363 0.482368 0.041 Uiso 1 1 calc R U . . .
H2B H 0.554960 0.890546 0.464804 0.041 Uiso 1 1 calc R U . . .
N1 N 0.9283(3) 0.7271(7) 0.7630(3) 0.0553(14) Uani 1 1 d . . . . .
H1A H 0.947452 0.839709 0.784887 0.066 Uiso 1 1 calc R U . . .
C21 C 0.6426(3) 0.7163(7) 0.5279(3) 0.0314(12) Uani 1 1 d . . . . .
C6 C 0.4014(3) 0.7818(8) 0.6886(3) 0.0342(12) Uani 1 1 d . . . . .
O4 O 0.9582(3) 0.8548(8) 0.6564(3) 0.0815(15) Uani 1 1 d . . . . .
C16 C 0.7964(3) 0.5990(8) 0.6058(3) 0.0356(13) Uani 1 1 d . . . . .
C8 C 0.4396(3) 0.6990(8) 0.6247(3) 0.0326(12) Uani 1 1 d . . . . .
C18 C 0.7822(3) 0.7914(8) 0.5718(3) 0.0409(13) Uani 1 1 d . . . . .
H18A H 0.825019 0.883307 0.575362 0.049 Uiso 1 1 calc R U . . .
C19 C 0.7067(3) 0.8524(8) 0.5329(3) 0.0395(13) Uani 1 1 d . . . . .
H19A H 0.699198 0.982393 0.510437 0.047 Uiso 1 1 calc R U . . .
C10 C 0.9011(3) 0.5795(8) 0.8093(3) 0.0399(13) Uani 1 1 d . . . . .
C20 C 0.6541(3) 0.5246(8) 0.5612(3) 0.0408(13) Uani 1 1 d . . . . .
H20A H 0.611099 0.433142 0.557883 0.049 Uiso 1 1 calc R U . . .
C17 C 0.7309(3) 0.4691(8) 0.6002(3) 0.0420(14) Uani 1 1 d . . . . .
H17A H 0.738238 0.339758 0.623147 0.050 Uiso 1 1 calc R U . . .
C7 C 0.3973(3) 0.6563(9) 0.7510(3) 0.0425(14) Uani 1 1 d . . . . .
H7A H 0.416418 0.521533 0.752120 0.051 Uiso 1 1 calc R U . . .
C13 C 0.8836(3) 0.5321(8) 0.6411(3) 0.0394(13) Uani 1 1 d . . . . .
C9 C 0.9275(3) 0.7102(9) 0.6860(3) 0.0455(14) Uani 1 1 d . . . . .
C12 C 0.8853(4) 0.3467(8) 0.6957(3) 0.0470(15) Uani 1 1 d . . . . .
H12A H 0.849071 0.241065 0.670155 0.056 Uiso 1 1 calc R U . . .
H12B H 0.939339 0.289195 0.706241 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3738(3) 0.9846(8) 0.6877(3) 0.0472(15) Uani 1 1 d . . . . .
H5A H 0.377423 1.070844 0.646789 0.057 Uiso 1 1 calc R U . . .
C11 C 0.8615(4) 0.3995(8) 0.7705(3) 0.0509(16) Uani 1 1 d . . . . .
H11A H 0.803644 0.422033 0.761016 0.061 Uiso 1 1 calc R U . . .
H11B H 0.873167 0.281698 0.804420 0.061 Uiso 1 1 calc R U . . .
C2 C 0.3648(4) 0.7301(10) 0.8116(3) 0.0542(16) Uani 1 1 d . . . . .
C4 C 0.3412(4) 1.0568(10) 0.7478(4) 0.0598(17) Uani 1 1 d . . . . .
H4A H 0.321905 1.191463 0.746926 0.072 Uiso 1 1 calc R U . . .
C3 C 0.3370(4) 0.9304(11) 0.8090(4) 0.0616(18) Uani 1 1 d . . . . .
H3A H 0.315073 0.981168 0.849196 0.074 Uiso 1 1 calc R U . . .
C14 C 0.9297(4) 0.4871(10) 0.5749(4) 0.0599(18) Uani 1 1 d . . . . .
H14A H 0.928400 0.610317 0.543712 0.072 Uiso 1 1 calc R U . . .
H14B H 0.985712 0.458138 0.597044 0.072 Uiso 1 1 calc R U . . .
C1 C 0.3619(5) 0.5938(13) 0.8804(4) 0.084(2) Uani 1 1 d . . . . .
H1B H 0.383514 0.460203 0.872664 0.126 Uiso 1 1 calc R U . . .
H1C H 0.393374 0.655687 0.925550 0.126 Uiso 1 1 calc R U . . .
H1D H 0.307007 0.579531 0.886569 0.126 Uiso 1 1 calc R U . . .
C15 C 0.8965(5) 0.3113(12) 0.5244(4) 0.081(2) Uani 1 1 d . . . . .
H15A H 0.927752 0.293383 0.485423 0.121 Uiso 1 1 calc R U . . .
H15B H 0.898791 0.187506 0.554373 0.121 Uiso 1 1 calc R U . . .
H15C H 0.841399 0.339897 0.500966 0.121 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 H1 109.5 . . ?
C21 N2 H2A 120.0 . . ?
C21 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C9 N1 C10 126.5(5) . . ?
C9 N1 H1A 116.7 . . ?
C10 N1 H1A 116.7 . . ?
C20 C21 C19 120.4(5) . . ?
C20 C21 N2 118.8(4) . . ?
C19 C21 N2 120.8(4) . . ?
C7 C6 C5 119.4(5) . . ?
C7 C6 C8 119.4(5) . . ?
C5 C6 C8 121.1(5) . . ?
C17 C16 C18 116.7(5) . . ?
C17 C16 C13 123.1(5) . . ?
C18 C16 C13 120.0(5) . . ?
O2 C8 O1 123.0(5) . . ?
O2 C8 C6 118.3(4) . . ?
O1 C8 C6 118.7(4) . . ?
C19 C18 C16 122.7(5) . . ?
C19 C18 H18A 118.7 . . ?
C16 C18 H18A 118.7 . . ?
C18 C19 C21 118.8(5) . . ?
C18 C19 H19A 120.6 . . ?
C21 C19 H19A 120.6 . . ?
O3 C10 N1 120.3(5) . . ?
O3 C10 C11 123.4(5) . . ?
N1 C10 C11 116.3(5) . . ?
C21 C20 C17 119.1(5) . . ?
C21 C20 H20A 120.4 . . ?
C17 C20 H20A 120.4 . . ?
C16 C17 C20 122.4(5) . . ?
C16 C17 H17A 118.8 . . ?
C20 C17 H17A 118.8 . . ?
C2 C7 C6 120.7(5) . . ?
C2 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C9 C13 C12 108.2(4) . . ?
C9 C13 C16 109.3(4) . . ?
C12 C13 C16 111.9(4) . . ?
C9 C13 C14 106.0(5) . . ?
C12 C13 C14 112.4(5) . . ?
C16 C13 C14 108.8(4) . . ?
O4 C9 N1 116.3(5) . . ?
O4 C9 C13 123.7(5) . . ?
N1 C9 C13 119.8(5) . . ?
C11 C12 C13 114.0(4) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C10 C11 C12 115.2(5) . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C3 C2 C7 118.8(6) . . ?
C3 C2 C1 120.6(6) . . ?
C7 C2 C1 120.6(6) . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C3 C2 121.1(6) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C15 C14 C13 114.4(5) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.257(6) . ?
O1 H1 0.8200 . ?
O2 C8 1.252(6) . ?
O3 C10 1.222(6) . ?
N2 C21 1.447(6) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N1 C9 1.374(7) . ?
N1 C10 1.399(7) . ?
N1 H1A 0.8600 . ?
C21 C20 1.373(7) . ?
C21 C19 1.386(7) . ?
C6 C7 1.390(7) . ?
C6 C5 1.393(7) . ?
C6 C8 1.514(7) . ?
O4 C9 1.237(7) . ?
C16 C17 1.379(7) . ?
C16 C18 1.386(7) . ?
C16 C13 1.545(7) . ?
C18 C19 1.384(7) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C10 C11 1.450(7) . ?
C20 C17 1.394(7) . ?
C20 H20A 0.9300 . ?
C17 H17A 0.9300 . ?
C7 C2 1.390(8) . ?
C7 H7A 0.9300 . ?
C13 C9 1.513(8) . ?
C13 C12 1.543(7) . ?
C13 C14 1.564(8) . ?
C12 C11 1.506(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 C4 1.380(8) . ?
C5 H5A 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 C3 1.377(9) . ?
C2 C1 1.520(8) . ?
C4 C3 1.376(9) . ?
C4 H4A 0.9300 . ?
C3 H3A 0.9300 . ?
C14 C15 1.490(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C20 H20A O3 0.93 2.49 3.214(7) 135.3 2_646 yes
N1 H1A O1 0.86 2.20 2.994(6) 153.6 2_656 yes
N2 H2B O2 0.86 2.00 2.850(5) 168.0 3_676 yes
C20 H20A O3 0.93 2.49 3.214(7) 135.3 2_646 yes
N1 H1A O1 0.86 2.20 2.994(6) 153.6 2_656 yes
N2 H2B O2 0.86 2.00 2.850(5) 168.0 3_676 yes
C20 H20A O3 0.93 2.49 3.214(7) 135.3 2_646 yes
N1 H1A O1 0.86 2.20 2.994(6) 153.6 2_656 yes
N2 H2B O2 0.86 2.00 2.850(5) 168.0 3_676 yes
N2 H2B O2 0.86 2.00 2.850(5) 168.0 3_676 yes
N1 H1A O1 0.86 2.20 2.994(6) 153.6 2_656 yes
C20 H20A O3 0.93 2.49 3.214(7) 135.3 2_646 yes
N2 H2B O2 0.86 2.00 2.850(5) 168.0 3_676 yes
N1 H1A O1 0.86 2.20 2.994(6) 153.6 2_656 yes
C20 H20A O3 0.93 2.49 3.214(7) 135.3 2_646 yes
N2 H2B O2 0.86 2.00 2.850(5) 168.0 3_676 yes
N1 H1A O1 0.86 2.20 2.994(6) 153.6 2_656 yes
C20 H20A O3 0.93 2.49 3.214(7) 135.3 2_646 yes
