#------------------------------------------------------------------------------
#$Date: 2022-05-20 01:33:24 +0300 (Fri, 20 May 2022) $
#$Revision: 275561 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/49/7244961.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_7244961
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 Br N2 O3'
_chemical_formula_sum            'C15 H15 Br N2 O3'
_chemical_formula_weight         351.2
_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                106.54(3)
_cell_angle_beta                 100.99(3)
_cell_angle_gamma                91.53(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6479(13)
_cell_length_b                   10.089(2)
_cell_length_c                   12.122(2)
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1040
_cell_measurement_theta_min      3.1400
_cell_volume                     762.3(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      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  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11556
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_min         3.133
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15135
_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    1.53
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0563
_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)+(0.0494P)²+0.9158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                2112
_reflns_number_total             2789
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00376g2.cif
_cod_data_source_block           2
_cod_original_cell_volume        762.2(3)
_cod_database_code               7244961
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 0.9519(5) 1.3011(4) 0.9111(3) 0.0400(9) Uani 1 1 d . . .
C4 C 0.7837(6) 1.1108(4) 0.9356(4) 0.0471(10) Uani 1 1 d . . .
C5 C 0.7546(6) 1.2365(4) 1.0323(3) 0.0399(9) Uani 1 1 d . . .
C6 C 0.8329(7) 1.2186(5) 1.1526(4) 0.0531(11) Uani 1 1 d . . .
H6A H 0.979599 1.209083 1.163535 0.064 Uiso 1 1 calc R U .
H6B H 0.765808 1.134314 1.157153 0.064 Uiso 1 1 calc R U .
C7 C 0.7917(8) 1.3420(5) 1.2505(4) 0.0630(13) Uani 1 1 d . . .
H7A H 0.836457 1.325137 1.325908 0.076 Uiso 1 1 calc R U .
H7B H 0.86998 1.424846 1.2512 0.076 Uiso 1 1 calc R U .
C8 C 0.5641(8) 1.3646(5) 1.2324(4) 0.0657(13) Uani 1 1 d . . .
H8A H 0.486834 1.284446 1.237654 0.079 Uiso 1 1 calc R U .
H8B H 0.541668 1.444944 1.29393 0.079 Uiso 1 1 calc R U .
C9 C 0.4880(7) 1.3865(5) 1.1145(5) 0.0621(13) Uani 1 1 d . . .
H9A H 0.557518 1.470883 1.111681 0.074 Uiso 1 1 calc R U .
H9B H 0.341794 1.397692 1.103927 0.074 Uiso 1 1 calc R U .
C10 C 0.5266(6) 1.2647(4) 1.0151(4) 0.0504(11) Uani 1 1 d . . .
H10A H 0.484344 1.284488 0.940774 0.06 Uiso 1 1 calc R U .
H10B H 0.444347 1.182394 1.012214 0.06 Uiso 1 1 calc R U .
C11 C 0.9368(6) 1.0713(4) 0.7558(4) 0.0438(10) Uani 1 1 d . . .
C12 C 0.7665(6) 0.9734(4) 0.6734(3) 0.0422(9) Uani 1 1 d . . .
C13 C 0.8155(6) 0.8559(4) 0.5947(4) 0.0550(12) Uani 1 1 d . . .
H13 H 0.952634 0.838794 0.596445 0.066 Uiso 1 1 calc R U .
C14 C 0.6629(7) 0.7638(5) 0.5135(4) 0.0620(13) Uani 1 1 d . . .
H14 H 0.696333 0.68467 0.461138 0.074 Uiso 1 1 calc R U .
C15 C 0.4619(6) 0.7909(4) 0.5113(4) 0.0502(11) Uani 1 1 d . . .
C16 C 0.4095(6) 0.9087(4) 0.5872(4) 0.0479(10) Uani 1 1 d . . .
H16 H 0.2724 0.927055 0.582959 0.057 Uiso 1 1 calc R U .
C17 C 0.5616(6) 0.9985(4) 0.6689(4) 0.0445(10) Uani 1 1 d . . .
H17 H 0.526862 1.076873 0.721581 0.053 Uiso 1 1 calc R U .
N1 N 0.8794(5) 1.3434(3) 1.0095(3) 0.0446(8) Uani 1 1 d . . .
H1 H 0.904106 1.42688 1.055807 0.054 Uiso 1 1 calc R U .
N3 N 0.8868(5) 1.1571(3) 0.8614(3) 0.0417(8) Uani 1 1 d . . .
O1 O 1.0512(4) 1.3678(3) 0.8681(2) 0.0504(7) Uani 1 1 d . . .
O2 O 0.7323(5) 0.9910(3) 0.9223(3) 0.0644(9) Uani 1 1 d . . .
O3 O 1.1062(4) 1.0837(3) 0.7373(3) 0.0612(9) Uani 1 1 d . . .
Br1 Br 0.24938(8) 0.67013(6) 0.39801(5) 0.0832(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 128.9(4) . . ?
O1 C2 N3 124.7(3) . . ?
N1 C2 N3 106.4(3) . . ?
O2 C4 N3 124.5(4) . . ?
O2 C4 C5 128.0(4) . . ?
N3 C4 C5 107.4(3) . . ?
N1 C5 C4 100.6(3) . . ?
N1 C5 C6 112.4(3) . . ?
C4 C5 C6 111.3(3) . . ?
N1 C5 C10 111.4(3) . . ?
C4 C5 C10 109.5(3) . . ?
C6 C5 C10 111.2(3) . . ?
C5 C6 C7 111.5(4) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108 . . ?
C8 C7 C6 110.7(4) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 110.9(4) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108 . . ?
C8 C9 C10 111.3(4) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
C9 C10 C5 111.4(3) . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C5 C10 H10B 109.3 . . ?
H10A C10 H10B 108 . . ?
O3 C11 N3 120.0(4) . . ?
O3 C11 C12 124.3(4) . . ?
N3 C11 C12 115.7(3) . . ?
C13 C12 C17 119.0(4) . . ?
C13 C12 C11 118.5(3) . . ?
C17 C12 C11 122.5(3) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 121.3(4) . . ?
C14 C15 Br1 120.1(3) . . ?
C16 C15 Br1 118.5(3) . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 120.5(4) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C2 N1 C5 114.6(3) . . ?
C2 N1 H1 122.7 . . ?
C5 N1 H1 122.7 . . ?
C4 N3 C2 110.2(3) . . ?
C4 N3 C11 125.4(3) . . ?
C2 N3 C11 124.1(3) . . ?
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 1.212(5) . ?
C2 N1 1.333(5) . ?
C2 N3 1.424(5) . ?
C4 O2 1.204(5) . ?
C4 N3 1.399(5) . ?
C4 C5 1.508(5) . ?
C5 N1 1.462(5) . ?
C5 C6 1.515(6) . ?
C5 C10 1.535(5) . ?
C6 C7 1.528(6) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.520(7) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.502(7) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.523(6) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O3 1.200(4) . ?
C11 N3 1.429(5) . ?
C11 C12 1.484(5) . ?
C12 C13 1.384(5) . ?
C12 C17 1.386(5) . ?
C13 C14 1.382(6) . ?
C13 H13 0.93 . ?
C14 C15 1.367(6) . ?
C14 H14 0.93 . ?
C15 C16 1.379(6) . ?
C15 Br1 1.893(4) . ?
C16 C17 1.372(5) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?
