#------------------------------------------------------------------------------
#$Date: 2018-08-07 13:44:48 +0300 (Tue, 07 Aug 2018) $
#$Revision: 209430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/93/7119377.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_7119377
loop_
_publ_author_name
'Zhu, Gongming'
'Yang, Junxian'
'Bao, Guangjun'
'Zhang, Ming'
'Li, Jing'
'Li, Yiping'
'Sun, Wangsheng'
'Hong, Liang'
'Wang, Rui'
_publ_section_title
;
 Catalyst-controlled switch of regioselectivity in the asymmetric allylic
 alkylation of oxazolones with MBHCs
;
_journal_issue                   50
_journal_name_full               'Chemical Communications'
_journal_page_first              7882
_journal_page_last               7885
_journal_paper_doi               10.1039/c6cc03246j
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H15 Cl N2 O2'
_chemical_formula_weight         350.79
_chemical_name_systematic        3ca'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1kpyry
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-02-01 deposited with the CCDC.
2016-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1740(7)
_cell_length_b                   14.3271(14)
_cell_length_c                   17.4194(17)
_cell_measurement_reflns_used    3659
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.74
_cell_volume                     1790.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9147
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3155
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0280
_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)+(0.0240P)²+0.3449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0661
_reflns_number_gt                2865
_reflns_number_total             3155
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc03246j2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value ' unk ' changed to 'unk'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 4624 2016-04-14 12:54:50Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7119377
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Cl1 Cl 0.34495(7) 0.30425(4) 0.13896(3) 0.05440(14) Uani 1 1 d . . .
O1 O 0.57443(17) 0.15110(8) 0.41157(6) 0.0407(3) Uani 1 1 d . . .
O2 O 0.09517(19) 0.18086(12) 0.39283(8) 0.0702(4) Uani 1 1 d . . .
N1 N 0.3079(2) 0.08313(12) 0.45329(9) 0.0497(4) Uani 1 1 d . . .
N2 N 0.7489(4) 0.01747(17) 0.26006(15) 0.1015(8) Uani 1 1 d . . .
C1 C 0.5600(2) 0.31097(12) 0.18511(9) 0.0401(4) Uani 1 1 d . . .
C2 C 0.6979(3) 0.36346(13) 0.15025(12) 0.0530(5) Uani 1 1 d . . .
H2 H 0.6740 0.3942 0.1043 0.064 Uiso 1 1 calc R . .
C3 C 0.8706(3) 0.36982(15) 0.18413(13) 0.0592(6) Uani 1 1 d . . .
H3 H 0.9639 0.4055 0.1614 0.071 Uiso 1 1 calc R . .
C4 C 0.9047(3) 0.32343(14) 0.25146(13) 0.0576(5) Uani 1 1 d . . .
H4 H 1.0215 0.3276 0.2743 0.069 Uiso 1 1 calc R . .
C5 C 0.7667(3) 0.27051(14) 0.28565(11) 0.0489(5) Uani 1 1 d . . .
H5 H 0.7930 0.2385 0.3308 0.059 Uiso 1 1 calc R . .
C6 C 0.5897(2) 0.26414(11) 0.25386(10) 0.0388(4) Uani 1 1 d . . .
C7 C 0.4360(2) 0.20640(12) 0.29003(9) 0.0387(4) Uani 1 1 d . . .
H7 H 0.3188 0.2343 0.2724 0.046 Uiso 1 1 calc R . .
C8 C 0.4376(3) 0.10726(14) 0.25814(11) 0.0497(5) Uani 1 1 d . . .
C9 C 0.6109(4) 0.05687(15) 0.25930(12) 0.0633(6) Uani 1 1 d . . .
C10 C 0.2889(4) 0.06712(18) 0.22790(14) 0.0798(8) Uani 1 1 d . . .
H10A H 0.2973 0.0071 0.2078 0.096 Uiso 1 1 calc R . .
H10B H 0.1758 0.0989 0.2267 0.096 Uiso 1 1 calc R . .
C11 C 0.4273(2) 0.20841(12) 0.37836(9) 0.0414(4) Uani 1 1 d . . .
C12 C 0.4368(3) 0.30596(14) 0.41224(12) 0.0597(5) Uani 1 1 d . . .
H12A H 0.4208 0.3026 0.4669 0.090 Uiso 1 1 calc R . .
H12B H 0.3397 0.3438 0.3905 0.090 Uiso 1 1 calc R . .
H12C H 0.5558 0.3332 0.4007 0.090 Uiso 1 1 calc R . .
C13 C 0.2535(3) 0.15807(15) 0.40744(11) 0.0493(5) Uani 1 1 d . . .
C14 C 0.4884(3) 0.08358(13) 0.45213(10) 0.0397(4) Uani 1 1 d . . .
C15 C 0.6084(3) 0.01565(12) 0.48970(9) 0.0406(4) Uani 1 1 d . . .
C16 C 0.7975(3) 0.01244(13) 0.47376(11) 0.0461(5) Uani 1 1 d . . .
H16 H 0.8502 0.0553 0.4400 0.055 Uiso 1 1 calc R . .
C17 C 0.9066(3) -0.05428(15) 0.50800(12) 0.0579(5) Uani 1 1 d . . .
H17 H 1.0338 -0.0562 0.4980 0.069 Uiso 1 1 calc R . .
C18 C 0.8283(4) -0.11817(17) 0.55704(13) 0.0718(7) Uani 1 1 d . . .
H18 H 0.9029 -0.1637 0.5795 0.086 Uiso 1 1 calc R . .
C19 C 0.6421(4) -0.11564(17) 0.57329(13) 0.0744(7) Uani 1 1 d . . .
H19 H 0.5909 -0.1590 0.6070 0.089 Uiso 1 1 calc R . .
C20 C 0.5300(3) -0.04897(15) 0.53991(11) 0.0577(6) Uani 1 1 d . . .
H20 H 0.4031 -0.0471 0.5508 0.069 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'
Cl Cl 0.1484 0.1585 '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
C14 O1 C11 106.30(13) . .
C14 N1 C13 105.49(16) . .
C2 C1 C6 122.10(17) . .
C2 C1 Cl1 117.44(14) . .
C6 C1 Cl1 120.47(14) . .
C3 C2 C1 119.47(18) . .
C3 C2 H2 120.3 . .
C1 C2 H2 120.3 . .
C4 C3 C2 119.72(19) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C3 C4 C5 120.5(2) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C4 C5 C6 121.27(18) . .
C4 C5 H5 119.4 . .
C6 C5 H5 119.4 . .
C5 C6 C1 116.91(16) . .
C5 C6 C7 122.38(16) . .
C1 C6 C7 120.68(16) . .
C6 C7 C8 110.57(15) . .
C6 C7 C11 115.76(15) . .
C8 C7 C11 112.43(14) . .
C6 C7 H7 105.7 . .
C8 C7 H7 105.7 . .
C11 C7 H7 105.7 . .
C10 C8 C9 119.0(2) . .
C10 C8 C7 123.0(2) . .
C9 C8 C7 117.99(19) . .
N2 C9 C8 179.5(3) . .
C8 C10 H10A 120.0 . .
C8 C10 H10B 120.0 . .
H10A C10 H10B 120.0 . .
O1 C11 C12 109.39(15) . .
O1 C11 C13 101.17(13) . .
C12 C11 C13 110.01(16) . .
O1 C11 C7 110.90(14) . .
C12 C11 C7 113.80(15) . .
C13 C11 C7 110.83(15) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O2 C13 N1 126.28(19) . .
O2 C13 C11 124.75(18) . .
N1 C13 C11 108.98(15) . .
N1 C14 O1 118.03(17) . .
N1 C14 C15 125.55(18) . .
O1 C14 C15 116.41(15) . .
C16 C15 C20 119.95(18) . .
C16 C15 C14 120.77(17) . .
C20 C15 C14 119.23(18) . .
C17 C16 C15 119.64(19) . .
C17 C16 H16 120.2 . .
C15 C16 H16 120.2 . .
C16 C17 C18 120.2(2) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C19 C18 C17 120.7(2) . .
C19 C18 H18 119.6 . .
C17 C18 H18 119.6 . .
C18 C19 C20 120.1(2) . .
C18 C19 H19 119.9 . .
C20 C19 H19 119.9 . .
C19 C20 C15 119.4(2) . .
C19 C20 H20 120.3 . .
C15 C20 H20 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.7423(18) .
O1 C14 1.348(2) .
O1 C11 1.457(2) .
O2 C13 1.209(2) .
N1 C14 1.295(2) .
N1 C13 1.394(2) .
N2 C9 1.140(3) .
C1 C2 1.383(3) .
C1 C6 1.389(2) .
C2 C3 1.376(3) .
C2 H2 0.9300 .
C3 C4 1.370(3) .
C3 H3 0.9300 .
C4 C5 1.382(3) .
C4 H4 0.9300 .
C5 C6 1.388(3) .
C5 H5 0.9300 .
C6 C7 1.516(2) .
C7 C8 1.525(3) .
C7 C11 1.540(2) .
C7 H7 0.9800 .
C8 C10 1.322(3) .
C8 C9 1.437(3) .
C10 H10A 0.9300 .
C10 H10B 0.9300 .
C11 C12 1.519(3) .
C11 C13 1.527(3) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C14 C15 1.455(3) .
C15 C16 1.386(3) .
C15 C20 1.392(3) .
C16 C17 1.372(3) .
C16 H16 0.9300 .
C17 C18 1.372(3) .
C17 H17 0.9300 .
C18 C19 1.366(3) .
C18 H18 0.9300 .
C19 C20 1.378(3) .
C19 H19 0.9300 .
C20 H20 0.9300 .
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
C6 C1 C2 C3 0.1(3) . . . .
Cl1 C1 C2 C3 -179.21(16) . . . .
C1 C2 C3 C4 0.7(3) . . . .
C2 C3 C4 C5 -0.1(3) . . . .
C3 C4 C5 C6 -1.2(3) . . . .
C4 C5 C6 C1 1.9(3) . . . .
C4 C5 C6 C7 179.83(18) . . . .
C2 C1 C6 C5 -1.4(3) . . . .
Cl1 C1 C6 C5 177.91(13) . . . .
C2 C1 C6 C7 -179.35(16) . . . .
Cl1 C1 C6 C7 0.0(2) . . . .
C5 C6 C7 C8 -90.8(2) . . . .
C1 C6 C7 C8 86.99(19) . . . .
C5 C6 C7 C11 38.5(2) . . . .
C1 C6 C7 C11 -143.70(16) . . . .
C6 C7 C8 C10 -126.6(2) . . . .
C11 C7 C8 C10 102.4(2) . . . .
C6 C7 C8 C9 51.6(2) . . . .
C11 C7 C8 C9 -79.5(2) . . . .
C10 C8 C9 N2 137(100) . . . .
C7 C8 C9 N2 -41(34) . . . .
C14 O1 C11 C12 115.11(16) . . . .
C14 O1 C11 C13 -0.95(16) . . . .
C14 O1 C11 C7 -118.57(15) . . . .
C6 C7 C11 O1 -75.58(18) . . . .
C8 C7 C11 O1 52.8(2) . . . .
C6 C7 C11 C12 48.3(2) . . . .
C8 C7 C11 C12 176.66(16) . . . .
C6 C7 C11 C13 172.87(14) . . . .
C8 C7 C11 C13 -58.7(2) . . . .
C14 N1 C13 O2 178.9(2) . . . .
C14 N1 C13 C11 -1.5(2) . . . .
O1 C11 C13 O2 -178.9(2) . . . .
C12 C11 C13 O2 65.5(3) . . . .
C7 C11 C13 O2 -61.2(3) . . . .
O1 C11 C13 N1 1.52(18) . . . .
C12 C11 C13 N1 -114.08(17) . . . .
C7 C11 C13 N1 119.19(17) . . . .
C13 N1 C14 O1 0.9(2) . . . .
C13 N1 C14 C15 -177.54(17) . . . .
C11 O1 C14 N1 0.1(2) . . . .
C11 O1 C14 C15 178.70(14) . . . .
N1 C14 C15 C16 168.30(19) . . . .
O1 C14 C15 C16 -10.2(2) . . . .
N1 C14 C15 C20 -9.2(3) . . . .
O1 C14 C15 C20 172.29(16) . . . .
C20 C15 C16 C17 -0.3(3) . . . .
C14 C15 C16 C17 -177.83(17) . . . .
C15 C16 C17 C18 0.8(3) . . . .
C16 C17 C18 C19 -0.9(4) . . . .
C17 C18 C19 C20 0.5(4) . . . .
C18 C19 C20 C15 -0.1(4) . . . .
C16 C15 C20 C19 0.0(3) . . . .
C14 C15 C20 C19 177.52(19) . . . .
