#------------------------------------------------------------------------------
#$Date: 2025-08-21 02:19:08 +0200 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/4/50/19/4501917.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_4501917
loop_
_publ_author_name
'Chattopadhyay, Basab'
'Mukherjee, Alok K.'
'Narendra, N.'
'Hemantha, H. P.'
'Sureshbabu, Vommina V.'
'Helliwell, Madeliene'
'Mukherjee, Monika'
_publ_section_title
;
 Supramolecular Architectures in 5,5&#x2032;-Substituted Hydantoins:
 Crystal Structures and Hirshfeld Surface Analyses
;
_journal_issue                   10
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              4476
_journal_paper_doi               10.1021/cg100706n
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C11 H20 N2 O2'
_chemical_formula_sum            'C11 H20 N2 O2'
_chemical_formula_weight         212.29
_chemical_name_common            Dbg-Hydantoin
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2010-01-25 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.7350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3072(12)
_cell_length_b                   9.5775(12)
_cell_length_c                   7.5116(9)
_cell_measurement_reflns_used    3901
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      3.13
_cell_volume                     612.95(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_source         'Station 9.8, SRS, Daresbury'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.69450
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10758
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1371
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0990P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                1370
_reflns_number_total             1371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100706n_si_003.cif
_cod_data_source_block           twin
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               4501917
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O4 O 0.1430(3) 0.0080(2) 0.2737(3) 0.0283(4) Uani 1 1 d .
O2 O 0.2365(3) 0.3867(2) 0.6711(3) 0.0327(5) Uani 1 1 d .
C5 C 0.2118(4) 0.2483(2) 0.2242(3) 0.0196(4) Uani 1 1 d .
C4 C 0.1761(3) 0.1280(3) 0.3322(4) 0.0198(5) Uani 1 1 d .
N3 N 0.1886(3) 0.1772(2) 0.5079(3) 0.0226(6) Uani 1 1 d .
H3 H 0.1749 0.1269 0.5947 0.027 Uiso 1 1 calc R
C2 C 0.2265(3) 0.3196(3) 0.5303(4) 0.0207(6) Uani 1 1 d .
N1 N 0.2451(3) 0.3605(2) 0.3694(3) 0.0237(5) Uani 1 1 d .
H1 H 0.2735 0.4434 0.3532 0.028 Uiso 1 1 calc R
C6 C 0.3536(4) 0.2151(3) 0.1779(4) 0.0241(6) Uani 1 1 d .
H6A H 0.3240 0.1417 0.0807 0.029 Uiso 1 1 calc R
H6B H 0.3779 0.2973 0.1199 0.029 Uiso 1 1 calc R
C7 C 0.5026(4) 0.1695(3) 0.3484(5) 0.0317(6) Uani 1 1 d .
H7A H 0.5362 0.2437 0.4444 0.038 Uiso 1 1 calc R
H7B H 0.4796 0.0881 0.4091 0.038 Uiso 1 1 calc R
C8 C 0.6329(5) 0.1355(5) 0.2879(6) 0.0463(9) Uani 1 1 d .
H8A H 0.6562 0.2184 0.2300 0.056 Uiso 1 1 calc R
H8B H 0.5961 0.0645 0.1875 0.056 Uiso 1 1 calc R
C9 C 0.7825(4) 0.0851(5) 0.4453(7) 0.0525(10) Uani 1 1 d .
H9A H 0.7712 -0.0110 0.4736 0.079 Uiso 1 1 calc R
H9B H 0.8056 0.1403 0.5602 0.079 Uiso 1 1 calc R
H9C H 0.8666 0.0938 0.4029 0.079 Uiso 1 1 calc R
C10 C 0.0682(4) 0.2814(3) 0.0342(4) 0.0241(6) Uani 1 1 d .
H10A H 0.0971 0.3546 -0.0342 0.029 Uiso 1 1 calc R
H10B H 0.0431 0.1989 -0.0476 0.029 Uiso 1 1 calc R
C11 C -0.0785(4) 0.3269(3) 0.0602(5) 0.0322(7) Uani 1 1 d .
H11A H -0.1111 0.2527 0.1236 0.039 Uiso 1 1 calc R
H11B H -0.0541 0.4082 0.1443 0.039 Uiso 1 1 calc R
C12 C -0.2120(4) 0.3618(5) -0.1301(5) 0.0446(9) Uani 1 1 d .
H12A H -0.1760 0.4337 -0.1934 0.053 Uiso 1 1 calc R
H12B H -0.2346 0.2795 -0.2121 0.053 Uiso 1 1 calc R
C13 C -0.3618(5) 0.4103(5) -0.1237(7) 0.0525(9) Uani 1 1 d .
H13A H -0.3396 0.4762 -0.0197 0.079 Uiso 1 1 calc R
H13B H -0.4172 0.3319 -0.1025 0.079 Uiso 1 1 calc R
H13C H -0.4254 0.4542 -0.2450 0.079 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0338(8) 0.0234(6) 0.0287(10) -0.0044(8) 0.0136(10) -0.0027(7)
O2 0.0418(11) 0.0265(8) 0.0300(10) -0.0095(8) 0.0146(10) -0.0010(7)
C5 0.0243(8) 0.0153(7) 0.0182(11) 0.0022(10) 0.0075(13) -0.0007(6)
C4 0.0210(11) 0.0215(9) 0.0184(12) -0.0001(8) 0.0095(12) -0.0012(8)
N3 0.0338(13) 0.0161(8) 0.0201(12) -0.0015(8) 0.0131(11) -0.0021(8)
C2 0.0214(12) 0.0175(10) 0.0204(13) 0.0008(9) 0.0056(11) 0.0027(9)
N1 0.0305(12) 0.0203(8) 0.0210(13) -0.0004(8) 0.0110(12) -0.0026(9)
C6 0.0207(12) 0.0307(10) 0.0207(13) 0.0012(10) 0.0082(11) -0.0009(9)
C7 0.0276(14) 0.0423(13) 0.0253(17) 0.0064(12) 0.0107(14) 0.0073(11)
C8 0.0261(15) 0.078(2) 0.0321(18) -0.0005(18) 0.0085(16) 0.0075(17)
C9 0.037(2) 0.075(3) 0.048(3) 0.011(2) 0.020(2) 0.0226(18)
C10 0.0234(12) 0.0288(10) 0.0171(13) 0.0037(9) 0.0049(11) 0.0006(9)
C11 0.0237(14) 0.0429(14) 0.0257(15) 0.0034(12) 0.0054(14) 0.0053(11)
C12 0.0301(18) 0.071(2) 0.0250(18) 0.0088(16) 0.0037(15) 0.0122(16)
C13 0.0304(17) 0.079(2) 0.043(3) 0.009(2) 0.009(2) 0.0149(19)
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
N1 C5 C4 100.61(16)
N1 C5 C6 112.1(3)
C4 C5 C6 111.0(2)
N1 C5 C10 112.4(2)
C4 C5 C10 110.8(3)
C6 C5 C10 109.75(17)
O4 C4 N3 125.7(2)
O4 C4 C5 126.7(2)
N3 C4 C5 107.7(2)
C4 N3 C2 111.8(2)
O2 C2 N1 129.6(2)
O2 C2 N3 123.3(3)
N1 C2 N3 107.0(2)
C2 N1 C5 112.8(2)
C7 C6 C5 116.4(2)
C8 C7 C6 112.5(3)
C7 C8 C9 116.2(3)
C11 C10 C5 115.4(2)
C12 C11 C10 112.5(3)
C13 C12 C11 117.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C4 1.225(3)
O2 C2 1.209(3)
C5 N1 1.473(3)
C5 C4 1.520(3)
C5 C6 1.528(4)
C5 C10 1.545(4)
C4 N3 1.362(3)
N3 C2 1.402(2)
C2 N1 1.346(3)
C6 C7 1.524(4)
C7 C8 1.493(5)
C8 C9 1.498(5)
C10 C11 1.519(4)
C11 C12 1.506(4)
C12 C13 1.489(6)
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
N3 H3 O4 0.86 1.97 2.827(3) 173.0 2
N1 H1 O2 0.86 2.06 2.826(3) 147.4 2_564
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
N1 C5 C4 O4 -178.8(2)
C6 C5 C4 O4 -59.9(4)
C10 C5 C4 O4 62.2(4)
N1 C5 C4 N3 0.8(4)
C6 C5 C4 N3 119.6(3)
C10 C5 C4 N3 -118.2(2)
O4 C4 N3 C2 -179.4(3)
C5 C4 N3 C2 1.1(3)
C4 N3 C2 O2 176.5(3)
C4 N3 C2 N1 -2.7(2)
O2 C2 N1 C5 -175.9(3)
N3 C2 N1 C5 3.2(3)
C4 C5 N1 C2 -2.5(4)
C6 C5 N1 C2 -120.5(3)
C10 C5 N1 C2 115.4(3)
N1 C5 C6 C7 58.7(3)
C4 C5 C6 C7 -52.9(3)
C10 C5 C6 C7 -175.7(2)
C5 C6 C7 C8 178.4(2)
C6 C7 C8 C9 -178.0(4)
N1 C5 C10 C11 -50.2(3)
C4 C5 C10 C11 61.5(3)
C6 C5 C10 C11 -175.7(2)
C5 C10 C11 C12 178.1(2)
C10 C11 C12 C13 -179.0(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 207953
2 PubChem 238122
