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#$Date: 2023-08-01 00:54:38 +0300 (Tue, 01 Aug 2023) $
#$Revision: 285394 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/19/7131946.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_7131946
loop_
_publ_author_name
'Panigrahi, Pritishree'
'Ghosh, Subhendu'
'Khandelia, Tamanna'
'Mandal, Raju'
'Patel, Bhisma K.'
_publ_section_title
;
 Isoxazole as nitrile synthon: En routes to ortho-alkenylated isoxazole
 and benzonitrile with allyl sulfone catalyzed by Ru(II)
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02996D
_journal_year                    2023
_chemical_formula_sum            'C16 H13 Cl N O2 S'
_chemical_formula_weight         318.78
_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-2018/3
_audit_update_record
;
2023-05-18 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.558(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.756(8)
_cell_length_b                   8.641(5)
_cell_length_c                   14.081(8)
_cell_measurement_reflns_used    8628
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.80
_cell_measurement_theta_min      2.67
_cell_volume                     1534.2(15)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0263
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33602
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.749
_exptl_absorpt_coefficient_mu    0.388
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       niddle
_exptl_crystal_F_000             660
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0590P)²+0.7860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2425
_reflns_number_total             2688
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02996d2.cif
_cod_data_source_block           PPALPH4Cl_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7131946
_shelx_shelxl_version_number     2018/3
_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
S001 S 0.67502(4) 0.64726(5) 0.64161(3) 0.03855(17) Uani 1 1 d . . . . .
Cl02 Cl 0.43712(5) 0.35631(14) 0.09752(6) 0.1131(4) Uani 1 1 d . . . . .
O003 O 0.57986(12) 0.56564(18) 0.63015(12) 0.0547(4) Uani 1 1 d . . . . .
O004 O 0.73863(13) 0.71432(19) 0.74058(11) 0.0584(4) Uani 1 1 d . . . . .
C005 C 0.70889(15) 0.4630(2) 0.50030(14) 0.0381(4) Uani 1 1 d . . . . .
H005 H 0.638405 0.431379 0.473249 0.046 Uiso 1 1 calc R U . . .
C006 C 0.71866(14) 0.4075(2) 0.33156(14) 0.0386(4) Uani 1 1 d . . . . .
C007 C 0.76188(14) 0.4582(2) 0.44006(14) 0.0397(4) Uani 1 1 d . . . . .
H007 H 0.832430 0.489518 0.468823 0.048 Uiso 1 1 calc R U . . .
C008 C 0.63897(14) 0.7932(2) 0.54610(14) 0.0382(4) Uani 1 1 d . . . . .
C009 C 0.75766(15) 0.5173(2) 0.61000(14) 0.0410(4) Uani 1 1 d . . . . .
H00A H 0.824400 0.568233 0.622012 0.049 Uiso 1 1 calc R U . . .
H00B H 0.772891 0.428320 0.655658 0.049 Uiso 1 1 calc R U . . .
C00A C 0.78641(15) 0.3625(2) 0.28360(15) 0.0420(4) Uani 1 1 d . . . . .
C00B C 0.54719(16) 0.7758(3) 0.45749(15) 0.0475(5) Uani 1 1 d . . . . .
H00C H 0.506489 0.686460 0.446986 0.057 Uiso 1 1 calc R U . . .
C00C C 0.70044(16) 0.9248(2) 0.56258(18) 0.0513(5) Uani 1 1 d . . . . .
H00D H 0.762018 0.935546 0.622367 0.062 Uiso 1 1 calc R U . . .
C00D C 0.61017(15) 0.4046(3) 0.27153(15) 0.0499(5) Uani 1 1 d . . . . .
H00E H 0.562880 0.434618 0.300284 0.060 Uiso 1 1 calc R U . . .
C00E C 0.74593(16) 0.3155(3) 0.18048(16) 0.0510(5) Uani 1 1 d . . . . .
H00F H 0.792095 0.285530 0.150383 0.061 Uiso 1 1 calc R U . . .
N00F N 0.98942(16) 0.3684(3) 0.38224(17) 0.0827(8) Uani 1 1 d . . . . .
C00G C 0.89966(17) 0.3653(3) 0.34004(16) 0.0536(6) Uani 1 1 d . . . . .
C00H C 0.63901(18) 0.3129(3) 0.12307(17) 0.0582(6) Uani 1 1 d . . . . .
H00H H 0.611760 0.281762 0.054110 0.070 Uiso 1 1 calc R U . . .
C00I C 0.6687(2) 1.0399(3) 0.4887(2) 0.0677(7) Uani 1 1 d . . . . .
H00I H 0.709451 1.129010 0.498314 0.081 Uiso 1 1 calc R U . . .
C00J C 0.57248(17) 0.3575(3) 0.16978(18) 0.0584(6) Uani 1 1 d . . . . .
C00K C 0.51696(19) 0.8932(3) 0.38488(18) 0.0614(6) Uani 1 1 d . . . . .
H00K H 0.455361 0.883448 0.324998 0.074 Uiso 1 1 calc R U . . .
C00L C 0.5776(2) 1.0237(3) 0.4010(2) 0.0690(7) Uani 1 1 d . . . . .
H00L H 0.556687 1.102556 0.351961 0.083 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
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
O003 S001 O004 118.70(10) . . ?
O003 S001 C008 107.40(9) . . ?
O004 S001 C008 109.12(10) . . ?
O003 S001 C009 107.87(10) . . ?
O004 S001 C009 107.16(10) . . ?
C008 S001 C009 105.89(9) . . ?
C007 C005 C009 122.63(18) . . ?
C00D C006 C00A 117.34(18) . . ?
C00D C006 C007 121.87(16) . . ?
C00A C006 C007 120.78(17) . . ?
C005 C007 C006 125.43(18) . . ?
C00C C008 C00B 121.20(19) . . ?
C00C C008 S001 119.60(15) . . ?
C00B C008 S001 119.15(15) . . ?
C005 C009 S001 112.95(13) . . ?
C00E C00A C006 121.06(18) . . ?
C00E C00A C00G 118.32(18) . . ?
C006 C00A C00G 120.61(18) . . ?
C008 C00B C00K 118.9(2) . . ?
C00I C00C C008 118.7(2) . . ?
C00J C00D C006 120.29(18) . . ?
C00H C00E C00A 120.61(19) . . ?
N00F C00G C00A 178.2(2) . . ?
C00E C00H C00J 118.4(2) . . ?
C00L C00I C00C 120.4(2) . . ?
C00D C00J C00H 122.3(2) . . ?
C00D C00J Cl02 118.93(17) . . ?
C00H C00J Cl02 118.80(18) . . ?
C00L C00K C00B 120.0(2) . . ?
C00K C00L C00I 120.8(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
S001 O003 1.4381(16) . ?
S001 O004 1.4383(16) . ?
S001 C008 1.764(2) . ?
S001 C009 1.776(2) . ?
Cl02 C00J 1.729(2) . ?
C005 C007 1.322(3) . ?
C005 C009 1.493(3) . ?
C006 C00D 1.391(3) . ?
C006 C00A 1.407(3) . ?
C006 C007 1.467(3) . ?
C008 C00C 1.380(3) . ?
C008 C00B 1.383(3) . ?
C00A C00E 1.392(3) . ?
C00A C00G 1.439(3) . ?
C00B C00K 1.381(3) . ?
C00C C00I 1.379(3) . ?
C00D C00J 1.376(3) . ?
C00E C00H 1.366(3) . ?
N00F C00G 1.137(3) . ?
C00H C00J 1.378(3) . ?
C00I C00L 1.370(4) . ?
C00K C00L 1.366(4) . ?
