#------------------------------------------------------------------------------
#$Date: 2023-06-29 12:55:08 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284579 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/68/7246882.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_7246882
loop_
_publ_author_name
'Lazić, Anita'
'Radovanović, Lidija'
'Rogan, Jelena'
'Valentić, Nataša'
'Janjić, Goran'
'Đorđević, Ivana'
'Trišović, Nemanja'
_publ_section_title
;
 Exploring the supramolecular profile of 5-phenylhydantoins
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              3637
_journal_page_last               3654
_journal_paper_doi               10.1039/D3CE00213F
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C11 H12 N2 O3'
_chemical_formula_sum            'C11 H12 N2 O3'
_chemical_formula_weight         220.23
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2023-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2259(12)
_cell_length_b                   7.1884(14)
_cell_length_c                   23.607(5)
_cell_measurement_reflns_used    3359
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1300
_cell_measurement_theta_min      2.9570
_cell_volume                     1056.5(4)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3280
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7319
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.326
_diffrn_reflns_theta_min         2.962
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 660 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.133(1)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0380P)²+0.1469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                1773
_reflns_number_total             1940
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00213f2.cif
_cod_data_source_block           3
_cod_database_code               7246882
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C2 C 0.7344(4) 0.4492(3) 0.54148(9) 0.0294(5) Uani 1 1 d . . . . .
C4 C 0.4518(3) 0.6094(3) 0.57806(8) 0.0278(5) Uani 1 1 d . . . . .
C5 C 0.6572(3) 0.7107(3) 0.59647(9) 0.0259(5) Uani 1 1 d . . . . .
C6 C 0.6819(3) 0.7143(3) 0.66100(8) 0.0256(5) Uani 1 1 d . . . . .
C7 C 0.5229(4) 0.7935(3) 0.69454(10) 0.0386(6) Uani 1 1 d . . . . .
H7 H 0.399712 0.840485 0.677469 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5438(4) 0.8037(4) 0.75223(10) 0.0428(6) Uani 1 1 d . . . . .
H8 H 0.434943 0.857077 0.773772 0.051 Uiso 1 1 calc R U . . .
C9 C 0.7256(4) 0.7352(3) 0.77866(9) 0.0344(5) Uani 1 1 d . . . . .
C10 C 0.8864(4) 0.6568(3) 0.74644(10) 0.0361(5) Uani 1 1 d . . . . .
H10 H 1.009705 0.610817 0.763709 0.043 Uiso 1 1 calc R U . . .
C11 C 0.8631(3) 0.6470(3) 0.68791(9) 0.0312(5) Uani 1 1 d . . . . .
H11 H 0.972059 0.593813 0.666372 0.037 Uiso 1 1 calc R U . . .
C12 C 0.9051(5) 0.6698(4) 0.86579(11) 0.0545(7) Uani 1 1 d . . . . .
H12A H 1.035783 0.728926 0.853892 0.082 Uiso 1 1 calc R U . . .
H12B H 0.912338 0.539217 0.857496 0.082 Uiso 1 1 calc R U . . .
H12C H 0.886397 0.68713 0.905813 0.082 Uiso 1 1 calc R U . . .
C13 C 0.6552(4) 0.9066(3) 0.57136(10) 0.0390(6) Uani 1 1 d . . . . .
H13A H 0.6276 0.899511 0.531405 0.059 Uiso 1 1 calc R U . . .
H13B H 0.791982 0.964661 0.577632 0.059 Uiso 1 1 calc R U . . .
H13C H 0.544617 0.978837 0.589262 0.059 Uiso 1 1 calc R U . . .
N1 N 0.8179(3) 0.5939(3) 0.56898(7) 0.0322(5) Uani 1 1 d . . . . .
H1 H 0.953453 0.616333 0.570398 0.039 Uiso 1 1 calc R U . . .
N3 N 0.5123(3) 0.4599(3) 0.54747(7) 0.0327(5) Uani 1 1 d . . . . .
H3 H 0.424052 0.380501 0.533312 0.039 Uiso 1 1 calc R U . . .
O1 O 0.8284(3) 0.3290(2) 0.51517(7) 0.0455(5) Uani 1 1 d . . . . .
O2 O 0.2687(2) 0.6618(3) 0.58716(7) 0.0429(4) Uani 1 1 d . . . . .
O3 O 0.7288(3) 0.7498(3) 0.83649(7) 0.0522(5) Uani 1 1 d . . . . .
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
O1 C2 N1 128.1(2) . . ?
O1 C2 N3 124.7(2) . . ?
N1 C2 N3 107.15(18) . . ?
O2 C4 N3 127.0(2) . . ?
O2 C4 C5 125.6(2) . . ?
N3 C4 C5 107.29(16) . . ?
N1 C5 C13 111.31(18) . . ?
N1 C5 C6 112.55(17) . . ?
C13 C5 C6 111.77(17) . . ?
N1 C5 C4 99.95(15) . . ?
C13 C5 C4 108.69(18) . . ?
C6 C5 C4 111.96(17) . . ?
C11 C6 C7 117.57(19) . . ?
C11 C6 C5 122.24(18) . . ?
C7 C6 C5 120.15(18) . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
O3 C9 C10 124.8(2) . . ?
O3 C9 C8 115.7(2) . . ?
C10 C9 C8 119.4(2) . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C6 C11 C10 121.6(2) . . ?
C6 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 N1 C5 113.50(17) . . ?
C2 N1 H1 123.3 . . ?
C5 N1 H1 123.3 . . ?
C4 N3 C2 112.08(18) . . ?
C4 N3 H3 124 . . ?
C2 N3 H3 124 . . ?
C9 O3 C12 117.8(2) . . ?
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
C2 O1 1.215(3) . ?
C2 N1 1.332(3) . ?
C2 N3 1.392(3) . ?
C4 O2 1.220(2) . ?
C4 N3 1.349(3) . ?
C4 C5 1.534(3) . ?
C5 N1 1.458(3) . ?
C5 C13 1.529(3) . ?
C5 C6 1.531(3) . ?
C6 C11 1.382(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.370(3) . ?
C7 H7 0.93 . ?
C8 C9 1.383(3) . ?
C8 H8 0.93 . ?
C9 O3 1.369(3) . ?
C9 C10 1.378(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 O3 1.419(3) . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
N1 H1 0.86 . ?
N3 H3 0.86 . ?
