#------------------------------------------------------------------------------
#$Date: 2022-05-20 01:33:24 +0300 (Fri, 20 May 2022) $
#$Revision: 275561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/49/7244960.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_7244960
loop_
_publ_author_name
'Lazić, Anita'
'Radovanović, Lidija'
'Gak Simić, Kristina'
'Rogan, Jelena'
'Janjić, Goran'
'Trišović, Nemanja'
'Đorđević, Ivana'
_publ_section_title
;
 Unravelling conformational and crystal packing preferences of
 cyclohexane-5-spirohydantoin derivatives incorporating a halogenated
 benzoyl group
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00376G
_journal_year                    2022
_chemical_formula_moiety         'C15 H15 Cl N2 O3'
_chemical_formula_sum            'C15 H15 Cl N2 O3'
_chemical_formula_weight         306.74
_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
;
2022-03-04 deposited with the CCDC.	2022-04-21 downloaded from the CCDC.
;
_cell_angle_alpha                108.19(3)
_cell_angle_beta                 99.76(3)
_cell_angle_gamma                104.73(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2836(13)
_cell_length_b                   10.928(2)
_cell_length_c                   12.159(2)
_cell_measurement_reflns_used    2201
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2780
_cell_measurement_theta_min      3.2340
_cell_volume                     738.4(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      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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9756
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.242
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.27
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.98944
_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    1.38
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
_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         2707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0548
_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)+(0.0457P)²+0.3053P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                1954
_reflns_number_total             2707
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00376g2.cif
_cod_data_source_block           1
_cod_database_code               7244960
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 1.0040(4) 0.8153(2) 1.4115(2) 0.0533(6) Uani 1 1 d . . .
C4 C 1.1903(5) 0.6735(2) 1.4534(2) 0.0636(7) Uani 1 1 d . . .
C5 C 1.2505(4) 0.7978(2) 1.5678(2) 0.0516(6) Uani 1 1 d . . .
C6 C 1.5068(5) 0.8737(3) 1.6065(3) 0.0743(8) Uani 1 1 d . . .
H6A H 1.588628 0.812542 1.61835 0.089 Uiso 1 1 calc R U .
H6B H 1.549701 0.902277 1.543226 0.089 Uiso 1 1 calc R U .
C7 C 1.5757(5) 0.9977(3) 1.7219(3) 0.0866(10) Uani 1 1 d . . .
H7A H 1.740178 1.041067 1.745594 0.104 Uiso 1 1 calc R U .
H7B H 1.505052 1.06278 1.708178 0.104 Uiso 1 1 calc R U .
C8 C 1.5042(7) 0.9589(3) 1.8211(3) 0.0986(11) Uani 1 1 d . . .
H8A H 1.542986 1.040279 1.892518 0.118 Uiso 1 1 calc R U .
H8B H 1.586109 0.900747 1.840253 0.118 Uiso 1 1 calc R U .
C9 C 1.2502(7) 0.8846(4) 1.7844(3) 0.0995(11) Uani 1 1 d . . .
H9A H 1.16879 0.946256 1.773457 0.119 Uiso 1 1 calc R U .
H9B H 1.209064 0.856368 1.848209 0.119 Uiso 1 1 calc R U .
C10 C 1.1773(6) 0.7599(3) 1.6685(3) 0.0819(9) Uani 1 1 d . . .
H10A H 1.244959 0.693578 1.681919 0.098 Uiso 1 1 calc R U .
H10B H 1.012385 0.718348 1.645255 0.098 Uiso 1 1 calc R U .
C11 C 0.9878(5) 0.6100(2) 1.2386(2) 0.0607(7) Uani 1 1 d . . .
C12 C 0.7587(4) 0.5097(2) 1.1808(2) 0.0510(6) Uani 1 1 d . . .
C13 C 0.7114(5) 0.4265(2) 1.0609(2) 0.0622(7) Uani 1 1 d . . .
H13 H 0.823787 0.436729 1.020447 0.075 Uiso 1 1 calc R U .
C14 C 0.5011(5) 0.3294(3) 1.0015(2) 0.0681(7) Uani 1 1 d . . .
H14 H 0.469546 0.274118 0.921134 0.082 Uiso 1 1 calc R U .
C15 C 0.3387(5) 0.3155(3) 1.0625(3) 0.0670(7) Uani 1 1 d . . .
C16 C 0.3802(5) 0.3971(3) 1.1808(3) 0.0680(7) Uani 1 1 d . . .
H16 H 0.266685 0.386452 1.22051 0.082 Uiso 1 1 calc R U .
C17 C 0.5905(4) 0.4945(2) 1.2400(2) 0.0581(7) Uani 1 1 d . . .
H17 H 0.619853 0.55037 1.320038 0.07 Uiso 1 1 calc R U .
N1 N 1.1209(3) 0.87515(18) 1.52673(17) 0.0555(5) Uani 1 1 d . . .
H1 H 1.119888 0.952713 1.572776 0.067 Uiso 1 1 calc R U .
N3 N 1.0411(3) 0.69006(18) 1.36658(17) 0.0555(5) Uani 1 1 d . . .
O1 O 0.8845(3) 0.85490(17) 1.35087(16) 0.0744(6) Uani 1 1 d . . .
O2 O 1.2592(4) 0.5780(2) 1.43895(19) 0.1010(8) Uani 1 1 d . . .
O3 O 1.1386(4) 0.6285(2) 1.19096(19) 0.0973(7) Uani 1 1 d . . .
Cl1 Cl 0.07436(14) 0.19150(10) 0.98779(8) 0.1080(4) 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 129.5(2) . . ?
O1 C2 N3 123.3(2) . . ?
N1 C2 N3 107.2(2) . . ?
O2 C4 N3 125.5(2) . . ?
O2 C4 C5 127.4(3) . . ?
N3 C4 C5 107.04(19) . . ?
N1 C5 C10 112.2(2) . . ?
N1 C5 C4 100.88(19) . . ?
C10 C5 C4 111.9(2) . . ?
N1 C5 C6 111.6(2) . . ?
C10 C5 C6 110.1(2) . . ?
C4 C5 C6 109.8(2) . . ?
C7 C6 C5 111.7(2) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 111.1(3) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108 . . ?
C7 C8 C9 110.7(3) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 111.8(3) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C5 C10 C9 111.2(2) . . ?
C5 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C5 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108 . . ?
O3 C11 N3 117.0(3) . . ?
O3 C11 C12 125.7(2) . . ?
N3 C11 C12 117.3(2) . . ?
C17 C12 C13 119.3(2) . . ?
C17 C12 C11 123.1(2) . . ?
C13 C12 C11 117.7(2) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 Cl1 118.7(2) . . ?
C16 C15 Cl1 119.6(2) . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 H17 120 . . ?
C12 C17 H17 120 . . ?
C2 N1 C5 113.84(18) . . ?
C2 N1 H1 123.1 . . ?
C5 N1 H1 123.1 . . ?
C4 N3 C2 111.0(2) . . ?
C4 N3 C11 123.13(19) . . ?
C2 N3 C11 123.3(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 1.213(3) . ?
C2 N1 1.328(3) . ?
C2 N3 1.401(3) . ?
C4 O2 1.203(3) . ?
C4 N3 1.377(3) . ?
C4 C5 1.517(3) . ?
C5 N1 1.450(3) . ?
C5 C10 1.514(4) . ?
C5 C6 1.524(4) . ?
C6 C7 1.517(4) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.497(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.509(5) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.523(4) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O3 1.199(3) . ?
C11 N3 1.457(3) . ?
C11 C12 1.463(4) . ?
C12 C17 1.381(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.371(4) . ?
C13 H13 0.93 . ?
C14 C15 1.365(4) . ?
C14 H14 0.93 . ?
C15 C16 1.373(4) . ?
C15 Cl1 1.731(3) . ?
C16 C17 1.371(4) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?
