#------------------------------------------------------------------------------
#$Date: 2023-06-29 12:55:08 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284579 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/68/7246881.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_7246881
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_formula_moiety         'C11 H12 N2 O2'
_chemical_formula_sum            'C11 H12 N2 O2'
_chemical_formula_weight         204.23
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   7.3489(15)
_cell_length_b                   14.605(3)
_cell_length_c                   19.983(4)
_cell_measurement_reflns_used    3601
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.2900
_cell_measurement_theta_min      3.2500
_cell_volume                     2144.8(8)
_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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.789
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   analytical
_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    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0416
_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)+(0.0471P)²+0.5968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.109
_reflns_number_gt                1473
_reflns_number_total             1959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00213f2.cif
_cod_data_source_block           2
_cod_original_cell_volume        2144.8(7)
_cod_database_code               7246881
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'
'-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 0.0063(2) 0.49319(11) 0.33795(8) 0.0362(4) Uani 1 1 d . . . . .
C4 C 0.1879(2) 0.47742(11) 0.42975(8) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.3111(2) 0.47539(11) 0.36805(7) 0.0335(4) Uani 1 1 d . . . . .
C6 C 0.4194(2) 0.38601(11) 0.36430(8) 0.0362(4) Uani 1 1 d . . . . .
C7 C 0.5532(2) 0.36848(12) 0.41164(9) 0.0435(4) Uani 1 1 d . . . . .
H7 H 0.573746 0.411147 0.445349 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6569(3) 0.28948(13) 0.41018(11) 0.0550(5) Uani 1 1 d . . . . .
C9 C 0.6265(3) 0.22756(14) 0.35939(13) 0.0689(6) Uani 1 1 d . . . . .
H9 H 0.696152 0.174506 0.356963 0.083 Uiso 1 1 calc R U . . .
C10 C 0.4945(3) 0.24345(14) 0.31248(12) 0.0738(7) Uani 1 1 d . . . . .
H10 H 0.475068 0.20067 0.278755 0.089 Uiso 1 1 calc R U . . .
C11 C 0.3891(3) 0.32242(13) 0.31437(10) 0.0552(5) Uani 1 1 d . . . . .
H11 H 0.299244 0.332313 0.282397 0.066 Uiso 1 1 calc R U . . .
C12 C 0.8002(3) 0.27157(17) 0.46296(15) 0.0867(8) Uani 1 1 d . . . . .
H12A H 0.784083 0.211139 0.480901 0.13 Uiso 1 1 calc R U . . .
H12B H 0.788532 0.315798 0.498241 0.13 Uiso 1 1 calc R U . . .
H12C H 0.91893 0.276414 0.44323 0.13 Uiso 1 1 calc R U . . .
C13 C 0.4345(2) 0.55989(12) 0.37025(10) 0.0468(5) Uani 1 1 d . . . . .
H13A H 0.508491 0.561675 0.330671 0.07 Uiso 1 1 calc R U . . .
H13B H 0.511359 0.556795 0.409032 0.07 Uiso 1 1 calc R U . . .
H13C H 0.361044 0.61416 0.372415 0.07 Uiso 1 1 calc R U . . .
N1 N 0.17590(18) 0.48344(10) 0.31540(7) 0.0412(4) Uani 1 1 d . . . . .
H1 H 0.202761 0.482046 0.273521 0.049 Uiso 1 1 calc R U . . .
N3 N 0.01572(17) 0.48769(10) 0.40755(6) 0.0391(4) Uani 1 1 d . . . . .
H3 H -0.077673 0.490518 0.433401 0.047 Uiso 1 1 calc R U . . .
O1 O -0.13345(16) 0.50553(9) 0.30664(6) 0.0513(4) Uani 1 1 d . . . . .
O2 O 0.23727(15) 0.47303(8) 0.48776(5) 0.0452(3) 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 129.15(15) . . ?
O1 C2 N3 124.33(14) . . ?
N1 C2 N3 106.52(13) . . ?
O2 C4 N3 126.79(14) . . ?
O2 C4 C5 126.19(14) . . ?
N3 C4 C5 106.99(13) . . ?
N1 C5 C4 100.22(11) . . ?
N1 C5 C6 112.91(13) . . ?
C4 C5 C6 111.31(13) . . ?
N1 C5 C13 111.14(13) . . ?
C4 C5 C13 108.16(13) . . ?
C6 C5 C13 112.38(13) . . ?
C11 C6 C7 118.83(16) . . ?
C11 C6 C5 121.68(15) . . ?
C7 C6 C5 119.48(14) . . ?
C8 C7 C6 122.00(17) . . ?
C8 C7 H7 119 . . ?
C6 C7 H7 119 . . ?
C9 C8 C7 118.26(19) . . ?
C9 C8 C12 120.87(19) . . ?
C7 C8 C12 120.87(19) . . ?
C10 C9 C8 120.56(19) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C6 C11 C10 119.19(19) . . ?
C6 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 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 113.80(13) . . ?
C2 N1 H1 123.1 . . ?
C5 N1 H1 123.1 . . ?
C4 N3 C2 112.40(13) . . ?
C4 N3 H3 123.8 . . ?
C2 N3 H3 123.8 . . ?
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
C2 O1 1.2158(19) . ?
C2 N1 1.333(2) . ?
C2 N3 1.395(2) . ?
C4 O2 1.2163(18) . ?
C4 N3 1.3492(19) . ?
C4 C5 1.530(2) . ?
C5 N1 1.4520(19) . ?
C5 C6 1.531(2) . ?
C5 C13 1.532(2) . ?
C6 C11 1.381(2) . ?
C6 C7 1.389(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.93 . ?
C8 C9 1.378(3) . ?
C8 C12 1.513(3) . ?
C9 C10 1.369(3) . ?
C9 H9 0.93 . ?
C10 C11 1.390(3) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
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 . ?
