#------------------------------------------------------------------------------
#$Date: 2021-01-07 09:05:54 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157751.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_7157751
loop_
_publ_author_name
'Wan, Shu-Hao'
'Li, Xuan-An'
'Liu, Yi-Hung'
'Liu, Shiuh-Tzung'
_publ_section_title
;
 N-Allylation versus C-allylation of intermediates from
 aza-Michael adducts of arylideneisoxazol-5-ones.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9516
_journal_page_last               9525
_journal_paper_doi               10.1039/d0ob01998d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C28 H25 Cl3 N2 O4 S'
_chemical_formula_weight         591.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-08-26 deposited with the CCDC.	2020-11-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.173(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9981(3)
_cell_length_b                   15.1043(3)
_cell_length_c                   18.6398(4)
_cell_measurement_reflns_used    6542
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.0270
_cell_measurement_theta_min      3.2260
_cell_volume                     2812.85(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.2496
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16245
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.910
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97929
_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_density_diffrn    1.398
_exptl_crystal_description       plate
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6303
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0712P)²+2.2772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4584
_reflns_number_total             6303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01998d2.cif
_cod_data_source_block           ic19240
_cod_depositor_comments
'Adding full bibliography for 7157751--7157753.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7157751
_shelx_shelxl_version_number     2017/1
_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. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.71186(6) 0.60604(4) 0.54127(3) 0.03706(17) Uani 1 1 d . . . . .
O1 O 0.85373(18) 0.61274(12) 0.55115(10) 0.0468(5) Uani 1 1 d . . . . .
O2 O 0.65394(19) 0.53177(11) 0.50406(9) 0.0446(4) Uani 1 1 d . . . . .
O3 O 0.5176(2) 0.89530(12) 0.41268(10) 0.0517(5) Uani 1 1 d . . . . .
O4 O 0.3011(2) 0.85786(13) 0.40991(11) 0.0566(5) Uani 1 1 d . . . . .
N1 N 0.66249(19) 0.69502(13) 0.49559(10) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.2174(2) 0.79604(17) 0.44679(14) 0.0559(6) Uani 1 1 d . . . . .
C1 C 0.6398(3) 0.61382(16) 0.62558(13) 0.0373(5) Uani 1 1 d . . . . .
C2 C 0.5172(3) 0.57467(17) 0.63577(14) 0.0426(6) Uani 1 1 d . . . . .
H2A H 0.474639 0.540552 0.598676 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4572(3) 0.5859(2) 0.70098(15) 0.0509(7) Uani 1 1 d . . . . .
H3A H 0.372681 0.559425 0.708305 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5186(3) 0.6354(2) 0.75586(14) 0.0518(7) Uani 1 1 d . . . . .
C5 C 0.6415(3) 0.6734(2) 0.74410(14) 0.0522(7) Uani 1 1 d . . . . .
H5A H 0.684439 0.707092 0.781339 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7035(3) 0.66372(19) 0.67955(14) 0.0453(6) Uani 1 1 d . . . . .
H6A H 0.787832 0.690555 0.672177 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4517(4) 0.6462(3) 0.82676(17) 0.0784(11) Uani 1 1 d . . . . .
H7A H 0.365902 0.614744 0.824965 0.118 Uiso 1 1 calc R U . . .
H7B H 0.509580 0.621639 0.865427 0.118 Uiso 1 1 calc R U . . .
H7C H 0.436258 0.709215 0.835817 0.118 Uiso 1 1 calc R U . . .
C8 C 0.7182(2) 0.77846(15) 0.51934(12) 0.0332(5) Uani 1 1 d . . . . .
C9 C 0.8500(2) 0.79935(18) 0.50651(13) 0.0403(6) Uani 1 1 d . . . . .
H9A H 0.904063 0.759565 0.480786 0.048 Uiso 1 1 calc R U . . .
C10 C 0.9020(3) 0.87881(19) 0.53159(16) 0.0488(7) Uani 1 1 d . . . . .
H10A H 0.992771 0.893381 0.523804 0.059 Uiso 1 1 calc R U . . .
C11 C 0.8226(3) 0.93695(18) 0.56784(16) 0.0495(7) Uani 1 1 d . . . . .
H11A H 0.859275 0.991255 0.585191 0.059 Uiso 1 1 calc R U . . .
C12 C 0.6894(3) 0.91688(17) 0.57927(14) 0.0425(6) Uani 1 1 d . . . . .
H12A H 0.635130 0.957680 0.603804 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6357(2) 0.83698(15) 0.55474(12) 0.0340(5) Uani 1 1 d . . . . .
C14 C 0.4909(2) 0.81109(15) 0.56263(12) 0.0345(5) Uani 1 1 d . . . . .
H14A H 0.487801 0.762397 0.598874 0.041 Uiso 1 1 calc R U . . .
C15 C 0.4379(2) 0.77359(15) 0.48873(12) 0.0346(5) Uani 1 1 d . . . . .
C16 C 0.5238(2) 0.69314(15) 0.46382(12) 0.0332(5) Uani 1 1 d . . . . .
H16A H 0.480371 0.638297 0.481921 0.040 Uiso 1 1 calc R U . . .
C17 C 0.4031(3) 0.88501(18) 0.58684(15) 0.0458(6) Uani 1 1 d . . . . .
H17A H 0.392959 0.935726 0.556983 0.055 Uiso 1 1 calc R U . . .
C18 C 0.3397(4) 0.8832(3) 0.6472(2) 0.0793(11) Uani 1 1 d . . . . .
H18A H 0.348205 0.833222 0.677987 0.095 Uiso 1 1 calc R U . . .
H18B H 0.285266 0.931767 0.660035 0.095 Uiso 1 1 calc R U . . .
C19 C 0.4317(3) 0.84826(17) 0.43377(13) 0.0421(6) Uani 1 1 d . . . . .
C20 C 0.2921(2) 0.74970(17) 0.48942(14) 0.0412(6) Uani 1 1 d . . . . .
C21 C 0.2307(3) 0.68140(19) 0.53530(18) 0.0551(7) Uani 1 1 d . . . . .
H21A H 0.300943 0.651956 0.564634 0.083 Uiso 1 1 calc R U . . .
H21B H 0.166902 0.709660 0.566703 0.083 Uiso 1 1 calc R U . . .
H21C H 0.183919 0.637562 0.504801 0.083 Uiso 1 1 calc R U . . .
C22 C 0.5230(3) 0.68605(16) 0.38271(13) 0.0390(6) Uani 1 1 d . . . . .
C23 C 0.4203(3) 0.64217(19) 0.34650(16) 0.0528(7) Uani 1 1 d . . . . .
H23A H 0.353154 0.613494 0.372770 0.063 Uiso 1 1 calc R U . . .
C24 C 0.4138(4) 0.6394(2) 0.27217(19) 0.0694(10) Uani 1 1 d . . . . .
H24A H 0.341713 0.609620 0.247847 0.083 Uiso 1 1 calc R U . . .
C25 C 0.5103(4) 0.6792(3) 0.23372(17) 0.0734(11) Uani 1 1 d . . . . .
H25A H 0.506541 0.676410 0.182766 0.088 Uiso 1 1 calc R U . . .
C26 C 0.6124(4) 0.7232(3) 0.26897(17) 0.0758(10) Uani 1 1 d . . . . .
H26A H 0.678971 0.751871 0.242285 0.091 Uiso 1 1 calc R U . . .
C27 C 0.6199(3) 0.7264(2) 0.34324(15) 0.0593(8) Uani 1 1 d . . . . .
H27A H 0.692063 0.756540 0.367178 0.071 Uiso 1 1 calc R U . . .
Cl1 Cl -0.1781(2) 0.56754(18) 0.34950(13) 0.0754(6) Uani 0.5 1 d . U P A 1
Cl2 Cl -0.0497(3) 0.4284(2) 0.2773(2) 0.1029(12) Uani 0.5 1 d . U P A 1
Cl3 Cl 0.1014(3) 0.5803(3) 0.3204(3) 0.1603(17) Uani 0.5 1 d . U P A 1
Cl1' Cl -0.1505(4) 0.5223(3) 0.3736(2) 0.1384(14) Uani 0.5 1 d . U P A 2
Cl2' Cl 0.0055(5) 0.4630(3) 0.2598(2) 0.1352(17) Uani 0.5 1 d . U P A 2
Cl3' Cl 0.0519(4) 0.6247(3) 0.3311(4) 0.195(2) Uani 0.5 1 d . U P A 2
C28 C -0.0137(4) 0.5134(2) 0.3397(2) 0.0749(10) Uani 1 1 d . U . . .
H28 H 0.012339 0.485001 0.386672 0.090 Uiso 1 1 calc R U . A 1
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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
O1 S1 O2 120.03(11) . . ?
O1 S1 N1 106.52(11) . . ?
O2 S1 N1 106.26(10) . . ?
O1 S1 C1 108.60(11) . . ?
O2 S1 C1 108.30(12) . . ?
N1 S1 C1 106.33(10) . . ?
C19 O4 N2 109.81(19) . . ?
C8 N1 C16 118.89(18) . . ?
C8 N1 S1 116.58(14) . . ?
C16 N1 S1 116.39(15) . . ?
C20 N2 O4 108.3(2) . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 S1 119.37(19) . . ?
C6 C1 S1 119.4(2) . . ?
C1 C2 C3 118.9(2) . . ?
C2 C3 C4 121.2(3) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 C7 121.3(3) . . ?
C3 C4 C7 120.2(3) . . ?
C4 C5 C6 121.7(3) . . ?
C5 C6 C1 118.6(3) . . ?
C9 C8 C13 121.5(2) . . ?
C9 C8 N1 120.4(2) . . ?
C13 C8 N1 118.1(2) . . ?
C10 C9 C8 119.2(2) . . ?
C11 C10 C9 120.2(3) . . ?
C10 C11 C12 120.6(2) . . ?
C11 C12 C13 119.9(2) . . ?
C12 C13 C8 118.6(2) . . ?
C12 C13 C14 123.5(2) . . ?
C8 C13 C14 118.0(2) . . ?
C17 C14 C13 114.2(2) . . ?
C17 C14 C15 110.6(2) . . ?
C13 C14 C15 107.56(19) . . ?
C20 C15 C19 99.7(2) . . ?
C20 C15 C14 112.09(19) . . ?
C19 C15 C14 109.16(19) . . ?
C20 C15 C16 111.03(19) . . ?
C19 C15 C16 112.55(19) . . ?
C14 C15 C16 111.75(18) . . ?
N1 C16 C22 111.64(19) . . ?
N1 C16 C15 112.33(18) . . ?
C22 C16 C15 111.57(18) . . ?
C18 C17 C14 123.3(3) . . ?
O3 C19 O4 121.3(2) . . ?
O3 C19 C15 130.6(2) . . ?
O4 C19 C15 108.1(2) . . ?
N2 C20 C21 119.6(3) . . ?
N2 C20 C15 114.0(2) . . ?
C21 C20 C15 126.4(2) . . ?
C23 C22 C27 118.5(3) . . ?
C23 C22 C16 119.9(2) . . ?
C27 C22 C16 121.5(2) . . ?
C22 C23 C24 120.7(3) . . ?
C25 C24 C23 120.4(3) . . ?
C24 C25 C26 119.5(3) . . ?
C25 C26 C27 120.6(4) . . ?
C22 C27 C26 120.3(3) . . ?
Cl1' C28 Cl2' 122.4(3) . . ?
Cl3 C28 Cl2 116.5(4) . . ?
Cl1' C28 Cl3' 106.6(3) . . ?
Cl2' C28 Cl3' 106.6(4) . . ?
Cl3 C28 Cl1 113.4(3) . . ?
Cl2 C28 Cl1 103.1(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
S1 O1 1.4270(19) . ?
S1 O2 1.4298(18) . ?
S1 N1 1.6561(19) . ?
S1 C1 1.757(3) . ?
O3 C19 1.193(3) . ?
O4 C19 1.371(3) . ?
O4 N2 1.445(3) . ?
N1 C8 1.441(3) . ?
N1 C16 1.487(3) . ?
N2 C20 1.278(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.392(3) . ?
C2 C3 1.386(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.381(4) . ?
C4 C7 1.512(4) . ?
C5 C6 1.382(4) . ?
C8 C9 1.384(3) . ?
C8 C13 1.392(3) . ?
C9 C10 1.382(4) . ?
C10 C11 1.378(4) . ?
C11 C12 1.390(4) . ?
C12 C13 1.391(3) . ?
C13 C14 1.512(3) . ?
C14 C17 1.500(3) . ?
C14 C15 1.563(3) . ?
C15 C20 1.503(3) . ?
C15 C19 1.523(3) . ?
C15 C16 1.569(3) . ?
C16 C22 1.515(3) . ?
C17 C18 1.312(4) . ?
C20 C21 1.487(4) . ?
C22 C23 1.377(4) . ?
C22 C27 1.381(4) . ?
C23 C24 1.385(4) . ?
C24 C25 1.364(6) . ?
C25 C26 1.365(5) . ?
C26 C27 1.385(4) . ?
Cl1 C28 1.852(4) . ?
Cl2 C28 1.761(5) . ?
Cl3 C28 1.583(5) . ?
Cl1' C28 1.534(5) . ?
Cl2' C28 1.690(6) . ?
Cl3' C28 1.813(5) . ?
