#------------------------------------------------------------------------------
#$Date: 2021-07-05 19:06:19 +0200 (lun 05 de jul de 2021) $
#$Revision: 267105 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/27/7242773.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_7242773
loop_
_publ_author_name
'Karnoukhova, Valentina A.'
'Baranov, Vladimir V.'
'Vologzhanina, Anna V.'
'Kravchenko, Angelina N.'
'Fedyanin, Ivan V.'
_publ_section_title
;
 Self-organization of 1,6-dialkyl-3a,6a-diphenylglycolurils in the
 crystalline state
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4312
_journal_page_last               4319
_journal_paper_doi               10.1039/D1CE00434D
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C18 H18 N4 O2, C H2 O2'
_chemical_formula_sum            'C19 H20 N4 O4'
_chemical_formula_weight         368.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                68.975(2)
_cell_angle_beta                 70.514(2)
_cell_angle_gamma                82.886(2)
_cell_formula_units_Z            2
_cell_length_a                   9.2955(10)
_cell_length_b                   9.6189(10)
_cell_length_c                   11.1769(12)
_cell_measurement_reflns_used    382
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     879.38(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11709
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.055
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       prism
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0410
_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/[σ²(Fo²)+(0.0548P)²+0.2519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4354
_reflns_number_total             5116
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            d1ce00434d4.cif
_cod_data_source_block           1a-HCOOH
_cod_depositor_comments
'Adding full bibliography for 7242772--7242787.cif.'
_cod_database_code               7242773
_shelx_shelxl_version_number     2016/6
_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   0.962
_shelx_estimated_absorpt_t_max   0.972
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 1.12896(9) 0.09543(9) 0.69930(8) 0.02070(18) Uani 1 1 d . . . . .
O2 O 0.56460(9) 0.03898(8) 1.11744(8) 0.01642(16) Uani 1 1 d . . . . .
N1 N 0.89765(10) 0.21175(10) 0.68899(9) 0.01506(18) Uani 1 1 d . . . . .
H1N H 0.8844(19) 0.1666(18) 0.6381(17) 0.029(4) Uiso 1 1 d . . . . .
N2 N 0.98743(10) 0.21142(10) 0.84952(9) 0.01497(18) Uani 1 1 d . . . . .
N3 N 0.73970(10) 0.22997(10) 1.00795(9) 0.01386(17) Uani 1 1 d . . . . .
N4 N 0.67724(10) 0.12260(10) 0.88675(9) 0.01407(17) Uani 1 1 d . . . . .
H4N H 0.6148(19) 0.0789(18) 0.8719(17) 0.029(4) Uiso 1 1 d . . . . .
C1 C 0.76690(11) 0.25167(11) 0.78430(10) 0.01267(19) Uani 1 1 d . . . . .
C2 C 1.01590(12) 0.16449(11) 0.74222(11) 0.0152(2) Uani 1 1 d . . . . .
C3 C 0.84453(11) 0.29455(11) 0.87332(10) 0.01257(18) Uani 1 1 d . . . . .
C4 C 0.65261(11) 0.12338(11) 1.01286(10) 0.01354(19) Uani 1 1 d . . . . .
C5 C 0.66988(12) 0.37239(11) 0.71699(10) 0.01333(19) Uani 1 1 d . . . . .
C6 C 0.73920(12) 0.48734(12) 0.59850(11) 0.0167(2) Uani 1 1 d . . . . .
H6A H 0.846610 0.486230 0.557529 0.020 Uiso 1 1 calc R U . . .
C7 C 0.65256(14) 0.60306(12) 0.54018(12) 0.0196(2) Uani 1 1 d . . . . .
H7A H 0.700881 0.681555 0.460221 0.024 Uiso 1 1 calc R U . . .
C8 C 0.49536(14) 0.60451(13) 0.59833(12) 0.0208(2) Uani 1 1 d . . . . .
H8A H 0.435754 0.683396 0.558057 0.025 Uiso 1 1 calc R U . . .
C9 C 0.42606(13) 0.49046(13) 0.71520(12) 0.0202(2) Uani 1 1 d . . . . .
H9A H 0.318424 0.491021 0.754996 0.024 Uiso 1 1 calc R U . . .
C10 C 0.51247(12) 0.37507(12) 0.77493(11) 0.0167(2) Uani 1 1 d . . . . .
H10A H 0.463813 0.297666 0.855690 0.020 Uiso 1 1 calc R U . . .
C11 C 0.86883(12) 0.45972(11) 0.83483(10) 0.01348(19) Uani 1 1 d . . . . .
C12 C 1.00308(12) 0.52585(12) 0.73823(11) 0.0166(2) Uani 1 1 d . . . . .
H12A H 1.082267 0.465853 0.702005 0.020 Uiso 1 1 calc R U . . .
C13 C 1.02243(14) 0.67924(13) 0.69416(12) 0.0211(2) Uani 1 1 d . . . . .
H13A H 1.114490 0.723521 0.628024 0.025 Uiso 1 1 calc R U . . .
C14 C 0.90778(15) 0.76716(13) 0.74657(13) 0.0240(2) Uani 1 1 d . . . . .
H14A H 0.921216 0.871786 0.716955 0.029 Uiso 1 1 calc R U . . .
C15 C 0.77311(15) 0.70240(13) 0.84245(13) 0.0228(2) Uani 1 1 d . . . . .
H15A H 0.693970 0.762974 0.877887 0.027 Uiso 1 1 calc R U . . .
C16 C 0.75341(13) 0.54910(12) 0.88696(11) 0.0176(2) Uani 1 1 d . . . . .
H16A H 0.661127 0.505235 0.953003 0.021 Uiso 1 1 calc R U . . .
C17 C 1.09564(13) 0.19278(13) 0.92193(12) 0.0194(2) Uani 1 1 d . . . . .
H17A H 1.194215 0.160463 0.872007 0.029 Uiso 1 1 calc R U . . .
H17B H 1.057834 0.117511 1.011662 0.029 Uiso 1 1 calc R U . . .
H17C H 1.108158 0.287732 0.931162 0.029 Uiso 1 1 calc R U . . .
C18 C 0.75874(13) 0.23978(12) 1.12881(11) 0.0178(2) Uani 1 1 d . . . . .
H18A H 0.660835 0.265742 1.185042 0.027 Uiso 1 1 calc R U . . .
H18B H 0.834053 0.316638 1.103020 0.027 Uiso 1 1 calc R U . . .
H18C H 0.794156 0.143549 1.179715 0.027 Uiso 1 1 calc R U . . .
O1S O 0.27821(10) -0.07977(10) 0.40638(9) 0.02588(19) Uani 1 1 d . . . . .
O2S O 0.47000(11) 0.06754(11) 0.36077(9) 0.0279(2) Uani 1 1 d . . . . .
H2S H 0.503(2) 0.047(2) 0.285(2) 0.045(5) Uiso 1 1 d . . . . .
C1S C 0.33844(13) 0.00181(13) 0.43520(12) 0.0206(2) Uani 1 1 d . . . . .
H1S H 0.287423 0.019947 0.517354 0.025 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'
H H 0.0000 0.0000 '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'
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
C2 N1 C1 110.68(9) . . ?
C2 N1 H1N 117.8(11) . . ?
C1 N1 H1N 119.6(11) . . ?
C2 N2 C17 122.86(9) . . ?
C2 N2 C3 112.57(8) . . ?
C17 N2 C3 124.30(9) . . ?
C4 N3 C3 110.97(8) . . ?
C4 N3 C18 122.22(9) . . ?
C3 N3 C18 123.87(8) . . ?
C4 N4 C1 111.48(8) . . ?
C4 N4 H4N 119.6(11) . . ?
C1 N4 H4N 122.9(11) . . ?
N1 C1 N4 113.05(8) . . ?
N1 C1 C5 112.87(8) . . ?
N4 C1 C5 112.69(8) . . ?
N1 C1 C3 101.62(8) . . ?
N4 C1 C3 99.95(8) . . ?
C5 C1 C3 115.59(8) . . ?
O1 C2 N2 125.72(10) . . ?
O1 C2 N1 126.16(10) . . ?
N2 C2 N1 108.09(9) . . ?
N3 C3 N2 112.90(8) . . ?
N3 C3 C11 112.97(8) . . ?
N2 C3 C11 112.79(8) . . ?
N3 C3 C1 101.82(8) . . ?
N2 C3 C1 100.24(8) . . ?
C11 C3 C1 115.02(8) . . ?
O2 C4 N4 125.27(9) . . ?
O2 C4 N3 125.02(10) . . ?
N4 C4 N3 109.71(9) . . ?
C10 C5 C6 118.99(10) . . ?
C10 C5 C1 121.00(9) . . ?
C6 C5 C1 119.93(9) . . ?
C7 C6 C5 120.51(10) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C8 120.13(11) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C9 C8 C7 119.58(10) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 120.55(10) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C9 C10 C5 120.24(10) . . ?
C9 C10 H10A 119.9 . . ?
C5 C10 H10A 119.9 . . ?
C12 C11 C16 119.14(10) . . ?
C12 C11 C3 119.80(9) . . ?
C16 C11 C3 120.87(9) . . ?
C11 C12 C13 120.55(10) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 120.03(11) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 119.89(10) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 120.27(11) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 120.13(11) . . ?
C15 C16 H16A 119.9 . . ?
C11 C16 H16A 119.9 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1S O2S H2S 109.2(13) . . ?
O1S C1S O2S 124.39(11) . . ?
O1S C1S H1S 117.8 . . ?
O2S C1S H1S 117.8 . . ?
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 C2 1.2229(13) . ?
O2 C4 1.2411(12) . ?
N1 C2 1.3737(14) . ?
N1 C1 1.4400(13) . ?
N1 H1N 0.874(17) . ?
N2 C2 1.3635(14) . ?
N2 C17 1.4468(14) . ?
N2 C3 1.4588(13) . ?
N3 C4 1.3583(13) . ?
N3 C3 1.4494(13) . ?
N3 C18 1.4561(14) . ?
N4 C4 1.3531(14) . ?
N4 C1 1.4651(13) . ?
N4 H4N 0.846(17) . ?
C1 C5 1.5146(14) . ?
C1 C3 1.5900(14) . ?
C3 C11 1.5145(14) . ?
C5 C10 1.3897(15) . ?
C5 C6 1.3957(14) . ?
C6 C7 1.3857(15) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3877(17) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3821(17) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3886(15) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3902(14) . ?
C11 C16 1.3942(15) . ?
C12 C13 1.3917(15) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3819(18) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3866(18) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3911(15) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1S C1S 1.2013(14) . ?
O2S C1S 1.3126(14) . ?
O2S H2S 0.88(2) . ?
C1S H1S 0.9500 . ?
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
N1 H1N O1S 0.874(17) 2.084(17) 2.8404(13) 144.3(15) 2_656
N4 H4N O2 0.846(17) 2.079(17) 2.9085(12) 166.8(16) 2_657
O2S H2S O2 0.88(2) 1.80(2) 2.6695(12) 169.8(19) 1_554
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N4 -80.42(11) . . . . ?
C2 N1 C1 C5 150.21(9) . . . . ?
C2 N1 C1 C3 25.79(10) . . . . ?
C4 N4 C1 N1 128.36(9) . . . . ?
C4 N4 C1 C5 -102.17(10) . . . . ?
C4 N4 C1 C3 21.10(10) . . . . ?
C17 N2 C2 O1 4.25(16) . . . . ?
C3 N2 C2 O1 178.44(10) . . . . ?
C17 N2 C2 N1 -174.17(9) . . . . ?
C3 N2 C2 N1 0.02(11) . . . . ?
C1 N1 C2 O1 164.02(10) . . . . ?
C1 N1 C2 N2 -17.57(11) . . . . ?
C4 N3 C3 N2 -86.78(10) . . . . ?
C18 N3 C3 N2 74.09(12) . . . . ?
C4 N3 C3 C11 143.74(9) . . . . ?
C18 N3 C3 C11 -55.38(13) . . . . ?
C4 N3 C3 C1 19.81(10) . . . . ?
C18 N3 C3 C1 -179.31(9) . . . . ?
C2 N2 C3 N3 122.63(9) . . . . ?
C17 N2 C3 N3 -63.27(12) . . . . ?
C2 N2 C3 C11 -107.80(10) . . . . ?
C17 N2 C3 C11 66.30(12) . . . . ?
C2 N2 C3 C1 15.03(10) . . . . ?
C17 N2 C3 C1 -170.87(9) . . . . ?
N1 C1 C3 N3 -139.58(8) . . . . ?
N4 C1 C3 N3 -23.36(9) . . . . ?
C5 C1 C3 N3 97.85(9) . . . . ?
N1 C1 C3 N2 -23.36(9) . . . . ?
N4 C1 C3 N2 92.87(8) . . . . ?
C5 C1 C3 N2 -145.93(8) . . . . ?
N1 C1 C3 C11 97.89(9) . . . . ?
N4 C1 C3 C11 -145.89(8) . . . . ?
C5 C1 C3 C11 -24.68(12) . . . . ?
C1 N4 C4 O2 170.29(10) . . . . ?
C1 N4 C4 N3 -10.14(12) . . . . ?
C3 N3 C4 O2 172.12(10) . . . . ?
C18 N3 C4 O2 10.87(16) . . . . ?
C3 N3 C4 N4 -7.45(12) . . . . ?
C18 N3 C4 N4 -168.70(9) . . . . ?
N1 C1 C5 C10 146.68(10) . . . . ?
N4 C1 C5 C10 17.12(13) . . . . ?
C3 C1 C5 C10 -96.95(11) . . . . ?
N1 C1 C5 C6 -36.58(13) . . . . ?
N4 C1 C5 C6 -166.14(9) . . . . ?
C3 C1 C5 C6 79.80(12) . . . . ?
C10 C5 C6 C7 0.57(16) . . . . ?
C1 C5 C6 C7 -176.25(10) . . . . ?
C5 C6 C7 C8 -0.88(17) . . . . ?
C6 C7 C8 C9 0.48(17) . . . . ?
C7 C8 C9 C10 0.24(17) . . . . ?
C8 C9 C10 C5 -0.55(17) . . . . ?
C6 C5 C10 C9 0.15(16) . . . . ?
C1 C5 C10 C9 176.93(10) . . . . ?
N3 C3 C11 C12 154.79(9) . . . . ?
N2 C3 C11 C12 25.25(13) . . . . ?
C1 C3 C11 C12 -88.89(11) . . . . ?
N3 C3 C11 C16 -30.37(13) . . . . ?
N2 C3 C11 C16 -159.90(9) . . . . ?
C1 C3 C11 C16 85.95(12) . . . . ?
C16 C11 C12 C13 0.13(16) . . . . ?
C3 C11 C12 C13 175.06(10) . . . . ?
C11 C12 C13 C14 0.09(17) . . . . ?
C12 C13 C14 C15 -0.42(18) . . . . ?
C13 C14 C15 C16 0.54(18) . . . . ?
C14 C15 C16 C11 -0.32(17) . . . . ?
C12 C11 C16 C15 -0.01(16) . . . . ?
C3 C11 C16 C15 -174.89(10) . . . . ?
