#------------------------------------------------------------------------------
#$Date: 2023-10-25 00:56:48 +0300 (Wed, 25 Oct 2023) $
#$Revision: 287091 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/22/7132250.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_7132250
loop_
_publ_author_name
'Zhan, Huilin'
'Chen, Bin'
'Zhu, Biao'
'Li, Xiang'
'Han, Zhengyu'
'Sun, Jianwei'
'Huang, Hai'
_publ_section_title
;
 Construction of 5-Methyleneoxazolidine-2,4-diones Bearing Modifiable
 Halogen Groups through a Halopalladation Strategy
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04475K
_journal_year                    2023
_chemical_formula_moiety         'C17 H12 Cl N O3'
_chemical_formula_sum            'C17 H12 Cl N O3'
_chemical_formula_weight         313.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-06-12
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-18 deposited with the CCDC.	2023-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.4445(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.33774(13)
_cell_length_b                   12.11111(16)
_cell_length_c                   12.88123(17)
_cell_measurement_reflns_used    6190
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.2080
_cell_measurement_theta_min      4.9170
_cell_volume                     1397.15(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00 115.00   1.00    2.00    --   39.95  37.00 150.00   99
  2  ω    -20.00  74.00   1.00    2.00    --   39.95 -77.00-120.00   94
  3  ω    -30.00  62.00   1.00    2.00    --   39.95 -37.00 -30.00   92
  4  ω     80.00 178.00   1.00    3.50    --  107.44  30.00  60.00   98
  5  ω     37.00 137.00   1.00    3.50    --  107.44 -61.00 -30.00  100
  6  ω     77.00 176.00   1.00    3.50    --  107.44  30.00 150.00   99
  7  ω     24.00  66.00   1.00    3.50    --  107.44 -94.00 -60.00   42
  8  ω     63.00 146.00   1.00    3.50    --  107.44 178.00 -60.00   83
  9  ω     79.00 109.00   1.00    3.50    --  107.44-111.00  60.00   30
 10  ω     79.00 104.00   1.00    3.50    --  107.44 -94.00 -60.00   25
 11  ω     29.00 109.00   1.00    3.50    --  107.44-111.00 -90.00   80
 12  ω     61.00 138.00   1.00    3.50    --  107.44 -61.00  60.00   77
 13  ω    110.00 165.00   1.00    3.50    --  107.44 111.00  90.00   55
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0702944000
_diffrn_orient_matrix_UB_12      0.0254561000
_diffrn_orient_matrix_UB_13      -0.0920519000
_diffrn_orient_matrix_UB_21      -0.0813597000
_diffrn_orient_matrix_UB_22      0.1119933000
_diffrn_orient_matrix_UB_23      -0.0190784000
_diffrn_orient_matrix_UB_31      0.1342149000
_diffrn_orient_matrix_UB_32      0.0547267000
_diffrn_orient_matrix_UB_33      0.0819836000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8023
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.102
_diffrn_reflns_theta_min         4.938
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.537
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0273
_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)+(0.0397P)²+0.5699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2632
_reflns_number_total             2780
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04475k2.cif
_cod_data_source_block           sliu11cult_auto
_cod_database_code               7132250
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C30 H28 Cl O N'
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.524
_oxdiff_exptl_absorpt_empirical_full_min 0.604
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl1 Cl 0.10736(3) 0.52221(2) 0.28482(2) 0.02170(10) Uani 1 1 d . . . . .
O1 O 0.50261(10) 0.33694(7) 0.03483(7) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.32056(10) 0.33731(8) 0.32779(7) 0.0230(2) Uani 1 1 d . . . . .
O3 O 0.33384(9) 0.44793(7) 0.07912(7) 0.01542(18) Uani 1 1 d . . . . .
N1 N 0.43491(11) 0.31218(8) 0.19293(8) 0.0162(2) Uani 1 1 d . . . . .
C1 C 0.43336(13) 0.36083(10) 0.09649(10) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.33962(13) 0.36406(10) 0.24262(10) 0.0164(2) Uani 1 1 d . . . . .
C3 C 0.27230(13) 0.45436(10) 0.16514(9) 0.0150(2) Uani 1 1 d . . . . .
C4 C 0.16776(13) 0.52918(9) 0.16953(9) 0.0153(2) Uani 1 1 d . . . . .
C5 C 0.09782(12) 0.61486(9) 0.08949(9) 0.0146(2) Uani 1 1 d . . . . .
C6 C 0.15602(13) 0.64211(10) 0.00359(10) 0.0177(2) Uani 1 1 d . . . . .
H6 H 0.2433 0.6061 -0.0032 0.021 Uiso 1 1 calc R U . . .
C7 C 0.08619(14) 0.72165(10) -0.07152(10) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.1257 0.7391 -0.1299 0.024 Uiso 1 1 calc R U . . .
C8 C -0.04101(14) 0.77614(10) -0.06235(10) 0.0193(3) Uani 1 1 d . . . . .
H8 H -0.0885 0.8300 -0.1143 0.023 Uiso 1 1 calc R U . . .
C9 C -0.09765(13) 0.75102(10) 0.02323(10) 0.0195(2) Uani 1 1 d . . . . .
H9 H -0.1835 0.7887 0.0306 0.023 Uiso 1 1 calc R U . . .
C10 C -0.02953(13) 0.67093(10) 0.09842(10) 0.0178(2) Uani 1 1 d . . . . .
H10 H -0.0698 0.6540 0.1565 0.021 Uiso 1 1 calc R U . . .
C11 C 0.52200(13) 0.21291(10) 0.23602(10) 0.0187(2) Uani 1 1 d . . . . .
H11A H 0.5597 0.2184 0.3158 0.022 Uiso 1 1 calc R U . . .
H11B H 0.6091 0.2079 0.2068 0.022 Uiso 1 1 calc R U . . .
C12 C 0.42768(12) 0.11012(10) 0.20578(9) 0.0156(2) Uani 1 1 d . . . . .
C13 C 0.35785(13) 0.06575(10) 0.27862(10) 0.0177(2) Uani 1 1 d . . . . .
H13 H 0.3735 0.0980 0.3482 0.021 Uiso 1 1 calc R U . . .
C14 C 0.26512(14) -0.02587(10) 0.24949(11) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.2173 -0.0559 0.2991 0.025 Uiso 1 1 calc R U . . .
C15 C 0.24238(14) -0.07340(10) 0.14803(11) 0.0231(3) Uani 1 1 d . . . . .
H15 H 0.1786 -0.1356 0.1281 0.028 Uiso 1 1 calc R U . . .
C16 C 0.31283(15) -0.03002(11) 0.07597(10) 0.0232(3) Uani 1 1 d . . . . .
H16 H 0.2981 -0.0631 0.0069 0.028 Uiso 1 1 calc R U . . .
C17 C 0.40503(14) 0.06175(10) 0.10416(10) 0.0197(3) Uani 1 1 d . . . . .
H17 H 0.4526 0.0915 0.0542 0.024 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O3 C3 108.98(9) . . ?
C1 N1 C2 112.35(10) . . ?
C1 N1 C11 123.81(10) . . ?
C2 N1 C11 123.77(10) . . ?
O1 C1 O3 122.94(11) . . ?
O1 C1 N1 129.06(11) . . ?
N1 C1 O3 108.00(10) . . ?
O2 C2 N1 125.36(11) . . ?
O2 C2 C3 131.50(11) . . ?
N1 C2 C3 103.14(10) . . ?
O3 C3 C2 107.54(10) . . ?
C4 C3 O3 122.76(10) . . ?
C4 C3 C2 129.67(11) . . ?
C3 C4 Cl1 114.79(9) . . ?
C3 C4 C5 128.78(11) . . ?
C5 C4 Cl1 116.43(9) . . ?
C6 C5 C4 121.45(10) . . ?
C10 C5 C4 120.02(11) . . ?
C10 C5 C6 118.53(11) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.12(11) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.84(12) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.37(11) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.34(11) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.79(11) . . ?
C9 C10 H10 119.6 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 C12 110.91(9) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C13 C12 C11 119.61(11) . . ?
C13 C12 C17 119.64(11) . . ?
C17 C12 C11 120.70(11) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.00(11) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.13(12) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.92(12) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.35(12) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 119.95(12) . . ?
C16 C17 H17 120.0 . . ?
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
Cl1 C4 1.7334(12) . ?
O1 C1 1.1931(15) . ?
O2 C2 1.2045(15) . ?
O3 C1 1.3816(14) . ?
O3 C3 1.3873(14) . ?
N1 C1 1.3713(15) . ?
N1 C2 1.3851(16) . ?
N1 C11 1.4694(15) . ?
C2 C3 1.4939(16) . ?
C3 C4 1.3448(17) . ?
C4 C5 1.4783(16) . ?
C5 C6 1.4032(17) . ?
C5 C10 1.4021(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3900(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3927(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3849(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3909(17) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5109(16) . ?
C12 C13 1.3932(17) . ?
C12 C17 1.3945(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3920(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3883(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3898(18) . ?
C17 H17 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C4 C5 C6 168.04(9) . . . . ?
Cl1 C4 C5 C10 -11.95(14) . . . . ?
O2 C2 C3 O3 -179.84(12) . . . . ?
O2 C2 C3 C4 -1.9(2) . . . . ?
O3 C3 C4 Cl1 -179.82(8) . . . . ?
O3 C3 C4 C5 0.70(19) . . . . ?
N1 C2 C3 O3 -0.45(12) . . . . ?
N1 C2 C3 C4 177.54(12) . . . . ?
N1 C11 C12 C13 -95.59(13) . . . . ?
N1 C11 C12 C17 81.87(14) . . . . ?
C1 O3 C3 C2 0.26(12) . . . . ?
C1 O3 C3 C4 -177.90(11) . . . . ?
C1 N1 C2 O2 179.93(11) . . . . ?
C1 N1 C2 C3 0.49(13) . . . . ?
C1 N1 C11 C12 -94.88(13) . . . . ?
C2 N1 C1 O1 179.42(12) . . . . ?
C2 N1 C1 O3 -0.36(13) . . . . ?
C2 N1 C11 C12 81.91(14) . . . . ?
C2 C3 C4 Cl1 2.46(17) . . . . ?
C2 C3 C4 C5 -177.02(11) . . . . ?
C3 O3 C1 O1 -179.76(11) . . . . ?
C3 O3 C1 N1 0.05(12) . . . . ?
C3 C4 C5 C6 -12.49(19) . . . . ?
C3 C4 C5 C10 167.52(12) . . . . ?
C4 C5 C6 C7 178.84(11) . . . . ?
C4 C5 C10 C9 -179.37(11) . . . . ?
C5 C6 C7 C8 0.64(19) . . . . ?
C6 C5 C10 C9 0.64(17) . . . . ?
C6 C7 C8 C9 0.44(18) . . . . ?
C7 C8 C9 C10 -0.97(18) . . . . ?
C8 C9 C10 C5 0.43(18) . . . . ?
C10 C5 C6 C7 -1.17(17) . . . . ?
C11 N1 C1 O1 -3.46(19) . . . . ?
C11 N1 C1 O3 176.75(9) . . . . ?
C11 N1 C2 O2 2.82(19) . . . . ?
C11 N1 C2 C3 -176.62(10) . . . . ?
C11 C12 C13 C14 176.99(10) . . . . ?
C11 C12 C17 C16 -177.27(11) . . . . ?
C12 C13 C14 C15 0.20(18) . . . . ?
C13 C12 C17 C16 0.19(17) . . . . ?
C13 C14 C15 C16 0.41(19) . . . . ?
C14 C15 C16 C17 -0.72(19) . . . . ?
C15 C16 C17 C12 0.42(19) . . . . ?
C17 C12 C13 C14 -0.49(17) . . . . ?
