#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:12:24 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/23/7242314.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_7242314
loop_
_publ_author_name
'Gak Simić, Kristina'
'Đorđević, Ivana'
'Lazić, Anita'
'Radovanović, Lidija'
'Petković-Benazzouz, Marija'
'Rogan, Jelena'
'Trišović, Nemanja'
'Janjić, Goran'
_publ_section_title
;
 On the supramolecular outcomes of fluorination of
 cyclohexane-5-spirohydantoin derivatives
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              2606
_journal_page_last               2622
_journal_paper_doi               10.1039/D0CE01841D
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C15 H15 F N2 O3'
_chemical_formula_sum            'C15 H15 F N2 O3'
_chemical_formula_weight         290.29
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-11-23 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                108.98(3)
_cell_angle_beta                 101.57(3)
_cell_angle_gamma                105.27(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9981(12)
_cell_length_b                   11.148(2)
_cell_length_c                   12.073(2)
_cell_measurement_reflns_used    1265
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.4770
_cell_measurement_theta_min      3.7870
_cell_volume                     699.3(3)
_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    'SIR-2014 (Burla et al., 2014)'
_diffrn_ambient_temperature      298(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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4747
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.303
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98839
_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    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0482
_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)+(0.0549P)²+0.0354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1198
_reflns_number_gt                1812
_reflns_number_total             2559
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01841d2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7242313--7242314.cif.'
_cod_database_code               7242314
_publcif_datablock.id            {9b1b73a6-1653-4fba-bb7e-d76a9cdd82ad}
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.0035(3) 0.18460(17) 0.59301(15) 0.0409(4) Uani 1 1 d . . .
C4 C -0.1836(4) 0.32441(19) 0.54737(17) 0.0481(5) Uani 1 1 d . . .
C5 C -0.2543(3) 0.19916(17) 0.42938(15) 0.0391(4) Uani 1 1 d . . .
C6 C -0.1692(4) 0.2363(2) 0.33005(17) 0.0577(6) Uani 1 1 d . . .
H6A H 0.006833 0.278256 0.358781 0.069 Uiso 1 1 calc R U .
H6B H -0.236893 0.301479 0.314631 0.069 Uiso 1 1 calc R U .
C7 C -0.2484(4) 0.1107(2) 0.21047(18) 0.0673(6) Uani 1 1 d . . .
H7A H -0.201073 0.137799 0.147467 0.081 Uiso 1 1 calc R U .
H7B H -0.165415 0.050392 0.223862 0.081 Uiso 1 1 calc R U .
C8 C -0.5205(4) 0.0357(2) 0.16567(18) 0.0694(7) Uani 1 1 d . . .
H8A H -0.603633 0.092176 0.143153 0.083 Uiso 1 1 calc R U .
H8B H -0.562641 -0.046352 0.092765 0.083 Uiso 1 1 calc R U .
C9 C -0.6043(4) -0.0008(2) 0.26438(19) 0.0639(6) Uani 1 1 d . . .
H9A H -0.535868 -0.065693 0.279939 0.077 Uiso 1 1 calc R U .
H9B H -0.780227 -0.043284 0.235511 0.077 Uiso 1 1 calc R U .
C10 C -0.5272(4) 0.1236(2) 0.38341(18) 0.0576(6) Uani 1 1 d . . .
H10A H -0.610032 0.18395 0.369852 0.069 Uiso 1 1 calc R U .
H10B H -0.575649 0.096134 0.445974 0.069 Uiso 1 1 calc R U .
C11 C 0.0388(4) 0.39243(19) 0.76958(17) 0.0486(5) Uani 1 1 d . . .
C12 C 0.2756(3) 0.50085(17) 0.82594(15) 0.0395(4) Uani 1 1 d . . .
C13 C 0.4443(4) 0.51574(19) 0.76408(17) 0.0489(5) Uani 1 1 d . . .
H13 H 0.405533 0.456924 0.682324 0.059 Uiso 1 1 calc R U .
C14 C 0.6688(4) 0.6167(2) 0.82231(19) 0.0623(6) Uani 1 1 d . . .
H14 H 0.783736 0.626298 0.781258 0.075 Uiso 1 1 calc R U .
C15 C 0.7198(4) 0.7024(2) 0.9414(2) 0.0649(6) Uani 1 1 d . . .
C16 C 0.5592(4) 0.6917(2) 1.00653(18) 0.0605(6) Uani 1 1 d . . .
H16 H 0.600443 0.751662 1.088108 0.073 Uiso 1 1 calc R U .
C17 C 0.3360(4) 0.59052(19) 0.94855(16) 0.0515(5) Uani 1 1 d . . .
H17 H 0.223587 0.581284 0.991015 0.062 Uiso 1 1 calc R U .
N1 N -0.1216(3) 0.12334(14) 0.47342(12) 0.0437(4) Uani 1 1 d . . .
H1 H -0.123677 0.045926 0.426472 0.052 Uiso 1 1 calc R U .
N3 N -0.0290(3) 0.30886(14) 0.63828(12) 0.0430(4) Uani 1 1 d . . .
O1 O 0.1274(3) 0.14520(13) 0.65628(11) 0.0598(4) Uani 1 1 d . . .
O2 O -0.2514(3) 0.41930(15) 0.56093(13) 0.0797(5) Uani 1 1 d . . .
O3 O -0.1069(3) 0.36695(16) 0.82089(14) 0.0905(6) Uani 1 1 d . . .
F1 F 0.9400(3) 0.80232(16) 0.99879(13) 0.1084(6) 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'
F F 0.0171 0.0103 '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 128.91(15) . . ?
O1 C2 N3 123.76(15) . . ?
N1 C2 N3 107.33(15) . . ?
O2 C4 N3 125.66(18) . . ?
O2 C4 C5 127.20(19) . . ?
N3 C4 C5 107.13(14) . . ?
N1 C5 C10 111.80(15) . . ?
N1 C5 C4 100.61(14) . . ?
C10 C5 C4 110.49(15) . . ?
N1 C5 C6 111.68(14) . . ?
C10 C5 C6 110.69(16) . . ?
C4 C5 C6 111.20(15) . . ?
C5 C6 C7 110.91(16) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108 . . ?
C8 C7 C6 111.80(18) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 110.97(16) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
C8 C9 C10 111.35(18) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
C5 C10 C9 111.82(16) . . ?
C5 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 C12 125.79(17) . . ?
O3 C11 N3 117.04(19) . . ?
C12 C11 N3 117.16(16) . . ?
C13 C12 C17 119.11(19) . . ?
C13 C12 C11 122.46(16) . . ?
C17 C12 C11 118.40(17) . . ?
C14 C13 C12 120.47(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
F1 C15 C14 118.7(2) . . ?
F1 C15 C16 118.1(2) . . ?
C14 C15 C16 123.1(2) . . ?
C15 C16 C17 118.19(18) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C12 120.51(19) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C2 N1 C5 113.82(14) . . ?
C2 N1 H1 123.1 . . ?
C5 N1 H1 123.1 . . ?
C4 N3 C2 111.07(14) . . ?
C4 N3 C11 123.88(14) . . ?
C2 N3 C11 123.20(14) . . ?
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 1.2211(19) . ?
C2 N1 1.330(2) . ?
C2 N3 1.396(2) . ?
C4 O2 1.205(2) . ?
C4 N3 1.376(2) . ?
C4 C5 1.520(2) . ?
C5 N1 1.452(2) . ?
C5 C10 1.517(3) . ?
C5 C6 1.526(2) . ?
C6 C7 1.526(3) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.513(3) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.512(3) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.517(3) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O3 1.195(2) . ?
C11 C12 1.454(3) . ?
C11 N3 1.459(2) . ?
C12 C13 1.380(2) . ?
C12 C17 1.398(2) . ?
C13 C14 1.372(3) . ?
C13 H13 0.93 . ?
C14 C15 1.360(3) . ?
C14 H14 0.93 . ?
C15 F1 1.350(3) . ?
C15 C16 1.365(3) . ?
C16 C17 1.367(3) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?
