#------------------------------------------------------------------------------
#$Date: 2022-05-03 04:06:35 +0300 (Tue, 03 May 2022) $
#$Revision: 274825 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158660.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_7158660
loop_
_publ_author_name
'Wan, Huiyang'
'Xia, Shuangshuang'
'Liu, Xinghua'
'Jian, Yongchan'
'An, Yuanyuan'
'Wang, Yubin'
_publ_section_title
;
 Synthesis of spirocyclic oxazole derivatives from 2-arylidene
 cycloalkanones and α-halohydroxamates
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00701K
_journal_year                    2022
_chemical_formula_moiety         'C22 H23 N O3'
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-30 deposited with the CCDC.	2022-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.802(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.572(4)
_cell_length_b                   5.7581(6)
_cell_length_c                   18.4236(19)
_cell_measurement_reflns_used    3555
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.31
_cell_volume                     3714.1(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16826
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.455
_diffrn_reflns_theta_min         2.266
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5514
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1309 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.7395.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0510P)²+2.0418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3301
_reflns_number_total             4225
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00701k2.cif
_cod_data_source_block           11_a
_cod_database_code               7158660
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C9(H9A,H9B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C5(H5), C4(H4), C1(H1), C2(H2), C22(H22), C18(H18), C20(H20),
 C19(H19), C21(H21)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O3 O 0.60363(3) 0.77461(17) 0.34953(6) 0.0286(2) Uani 1 1 d . . . . .
O1 O 0.65138(3) 0.34687(17) 0.27231(6) 0.0288(2) Uani 1 1 d . . . . .
O2 O 0.55950(3) 0.59848(18) 0.20830(7) 0.0368(3) Uani 1 1 d . . . . .
N1 N 0.61289(3) 0.5833(2) 0.31205(7) 0.0260(3) Uani 1 1 d . . . . .
C11 C 0.65306(4) 0.5248(2) 0.32670(8) 0.0238(3) Uani 1 1 d . . . . .
C15 C 0.59156(4) 0.5315(2) 0.24040(8) 0.0255(3) Uani 1 1 d . . . . .
C6 C 0.69218(4) 0.2392(2) 0.52980(8) 0.0255(3) Uani 1 1 d . . . . .
C8 C 0.67505(4) 0.4628(2) 0.40750(8) 0.0243(3) Uani 1 1 d . . . . .
C14 C 0.61652(4) 0.3697(2) 0.20974(8) 0.0264(3) Uani 1 1 d . . . . .
C7 C 0.66958(4) 0.2925(2) 0.45183(8) 0.0269(3) Uani 1 1 d . . . . .
H7 H 0.648918 0.195159 0.430941 0.032 Uiso 1 1 calc R . . . .
C10 C 0.68099(4) 0.7296(2) 0.32918(9) 0.0288(3) Uani 1 1 d . . . . .
H10A H 0.668879 0.881055 0.323640 0.035 Uiso 1 1 calc R . . . .
H10B H 0.696363 0.712050 0.294536 0.035 Uiso 1 1 calc R . . . .
C17 C 0.55846(4) 0.9082(3) 0.41041(9) 0.0305(3) Uani 1 1 d . . . . .
C9 C 0.70240(4) 0.6651(2) 0.41253(9) 0.0280(3) Uani 1 1 d . . . . .
H9A H 0.728706 0.618156 0.420022 0.034 Uiso 1 1 calc R . . . .
H9B H 0.700635 0.782815 0.449043 0.034 Uiso 1 1 calc R . . . .
C3 C 0.73499(4) 0.1265(3) 0.67824(9) 0.0327(3) Uani 1 1 d . . . . .
H3 H 0.749072 0.089714 0.727544 0.039 Uiso 1 1 calc R . . . .
C5 C 0.72552(4) 0.3617(3) 0.56694(9) 0.0308(3) Uani 1 1 d . . . . .
H5 H 0.733554 0.483409 0.542060 0.037 Uiso 1 1 calc R . . . .
C4 C 0.74662(4) 0.3044(3) 0.63990(9) 0.0331(3) Uani 1 1 d . . . . .
H4 H 0.768809 0.386406 0.663296 0.040 Uiso 1 1 calc R . . . .
C1 C 0.68124(4) 0.0584(3) 0.56939(9) 0.0328(3) Uani 1 1 d . . . . .
H1 H 0.659417 -0.026901 0.546064 0.039 Uiso 1 1 calc R . . . .
C2 C 0.70227(4) 0.0035(3) 0.64282(9) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.694309 -0.116703 0.668380 0.044 Uiso 1 1 calc R . . . .
C13 C 0.62523(5) 0.4813(3) 0.14188(9) 0.0363(4) Uani 1 1 d . . . . .
H13A H 0.638122 0.626454 0.156906 0.055 Uiso 1 1 calc GR . . . .
H13B H 0.601804 0.508282 0.102700 0.055 Uiso 1 1 calc GR . . . .
H13C H 0.641269 0.379841 0.123161 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.59862(5) 0.1310(2) 0.19254(10) 0.0360(4) Uani 1 1 d . . . . .
H12A H 0.615111 0.032335 0.174036 0.054 Uiso 1 1 calc GR . . . .
H12B H 0.574341 0.144133 0.154743 0.054 Uiso 1 1 calc GR . . . .
H12C H 0.595078 0.065441 0.237934 0.054 Uiso 1 1 calc GR . . . .
C22 C 0.53335(4) 1.0163(3) 0.34884(10) 0.0409(4) Uani 1 1 d . . . . .
H22 H 0.530975 0.962963 0.300051 0.049 Uiso 1 1 calc R . . . .
C18 C 0.56175(5) 0.9917(3) 0.48243(10) 0.0413(4) Uani 1 1 d . . . . .
H18 H 0.579013 0.922968 0.524129 0.050 Uiso 1 1 calc R . . . .
C16 C 0.58078(5) 0.7012(3) 0.39813(11) 0.0423(4) Uani 1 1 d . . . . .
H16A H 0.597158 0.645123 0.446216 0.051 Uiso 1 1 calc R . . . .
H16B H 0.563609 0.576896 0.374179 0.051 Uiso 1 1 calc R . . . .
C20 C 0.51479(5) 1.2817(3) 0.43124(11) 0.0441(4) Uani 1 1 d . . . . .
H20 H 0.500002 1.406584 0.438107 0.053 Uiso 1 1 calc R . . . .
C19 C 0.53965(5) 1.1760(3) 0.49308(11) 0.0456(4) Uani 1 1 d . . . . .
H19 H 0.541564 1.228414 0.541790 0.055 Uiso 1 1 calc R . . . .
C21 C 0.51184(5) 1.2029(3) 0.35954(11) 0.0483(5) Uani 1 1 d . . . . .
H21 H 0.495231 1.275731 0.317859 0.058 Uiso 1 1 calc R . . . .
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
N1 O3 C16 109.92(11) . . ?
C11 O1 C14 110.00(10) . . ?
O3 N1 C11 117.93(10) . . ?
C15 N1 O3 120.10(11) . . ?
C15 N1 C11 113.28(12) . . ?
O1 C11 N1 101.57(10) . . ?
O1 C11 C8 115.14(11) . . ?
O1 C11 C10 117.51(12) . . ?
N1 C11 C8 117.23(12) . . ?
N1 C11 C10 116.78(11) . . ?
C8 C11 C10 89.56(10) . . ?
O2 C15 N1 127.35(14) . . ?
O2 C15 C14 127.74(13) . . ?
N1 C15 C14 104.91(11) . . ?
C5 C6 C7 122.43(13) . . ?
C1 C6 C7 120.15(12) . . ?
C1 C6 C5 117.42(14) . . ?
C11 C8 C9 91.85(11) . . ?
C7 C8 C11 130.27(12) . . ?
C7 C8 C9 137.88(13) . . ?
O1 C14 C15 104.07(11) . . ?
O1 C14 C13 110.22(12) . . ?
O1 C14 C12 108.05(11) . . ?
C13 C14 C15 109.70(11) . . ?
C12 C14 C15 111.32(12) . . ?
C12 C14 C13 113.09(13) . . ?
C6 C7 H7 116.1 . . ?
C8 C7 C6 127.86(13) . . ?
C8 C7 H7 116.1 . . ?
C11 C10 H10A 113.8 . . ?
C11 C10 H10B 113.8 . . ?
C11 C10 C9 89.24(10) . . ?
H10A C10 H10B 111.0 . . ?
C9 C10 H10A 113.8 . . ?
C9 C10 H10B 113.8 . . ?
C22 C17 C16 119.71(15) . . ?
C18 C17 C22 118.86(15) . . ?
C18 C17 C16 121.41(15) . . ?
C8 C9 C10 89.32(10) . . ?
C8 C9 H9A 113.8 . . ?
C8 C9 H9B 113.8 . . ?
C10 C9 H9A 113.8 . . ?
C10 C9 H9B 113.8 . . ?
H9A C9 H9B 111.0 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.48(15) . . ?
C2 C3 H3 120.3 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.06(14) . . ?
C4 C5 H5 119.5 . . ?
C3 C4 C5 120.47(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C1 H1 119.4 . . ?
C2 C1 C6 121.26(14) . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 120.30(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C12 H12A 109.5 . . ?
C14 C12 H12B 109.5 . . ?
C14 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.28(16) . . ?
C21 C22 H22 119.9 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.72(16) . . ?
C19 C18 H18 119.6 . . ?
O3 C16 C17 107.27(12) . . ?
O3 C16 H16A 110.3 . . ?
O3 C16 H16B 110.3 . . ?
C17 C16 H16A 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C21 C20 C19 119.99(16) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.69(16) . . ?
C20 C19 H19 120.2 . . ?
C22 C21 H21 119.8 . . ?
C20 C21 C22 120.42(17) . . ?
C20 C21 H21 119.8 . . ?
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
O3 N1 1.3931(15) . ?
O3 C16 1.4531(19) . ?
O1 C11 1.4221(17) . ?
O1 C14 1.4568(16) . ?
O2 C15 1.2135(17) . ?
N1 C11 1.4541(17) . ?
N1 C15 1.3582(18) . ?
C11 C8 1.5160(19) . ?
C11 C10 1.5524(19) . ?
C15 C14 1.523(2) . ?
C6 C7 1.468(2) . ?
C6 C5 1.4036(19) . ?
C6 C1 1.394(2) . ?
C8 C7 1.328(2) . ?
C8 C9 1.5209(18) . ?
C14 C13 1.519(2) . ?
C14 C12 1.5159(19) . ?
C7 H7 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.554(2) . ?
C17 C22 1.384(2) . ?
C17 C18 1.383(2) . ?
C17 C16 1.498(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.379(2) . ?
C3 C2 1.381(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(2) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.386(2) . ?
C2 H2 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C22 H22 0.9300 . ?
C22 C21 1.379(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C20 H20 0.9300 . ?
C20 C19 1.377(3) . ?
C20 C21 1.371(3) . ?
C19 H19 0.9300 . ?
C21 H21 0.9300 . ?
