#------------------------------------------------------------------------------
#$Date: 2015-08-20 02:18:11 +0300 (Thu, 20 Aug 2015) $
#$Revision: 153526 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/42/4124281.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_4124281
loop_
_publ_author_name
'Zhu, Dianhu'
'Gu, Yang'
'Lu, Long'
'Shen, Qilong'
_publ_section_title
;
 N-Difluoromethylthiophthalimide: A Shelf-Stable, Electrophilic Reagent
 for Difluoromethylthiolation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              150818092125007
_journal_paper_doi               10.1021/jacs.5b03170
_journal_year                    2015
_chemical_formula_sum            'C9 H5 F2 N O2 S'
_chemical_formula_weight         229.20
_chemical_name_systematic
; 
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.445(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8060(13)
_cell_length_b                   7.9706(12)
_cell_length_c                   13.1908(18)
_cell_measurement_reflns_used    1665
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.532
_cell_measurement_theta_min      5.973
_cell_volume                     925.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5333
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_min         2.314
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0407
_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)+(0.0573P)²+0.1630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1096
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1474
_reflns_number_total             1814
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b03170_si_002.cif
_cod_data_source_block           cd214330
_cod_database_code               4124281
_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. 
;
_shelxl_version_number           2013-4
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
S1 S -0.29779(6) -0.00132(7) 0.69406(4) 0.0491(2) Uani 1 1 d . .
F1 F -0.3884(2) 0.2972(2) 0.74366(14) 0.0903(6) Uani 1 1 d . .
F2 F -0.45132(18) 0.0957(3) 0.84107(12) 0.0940(6) Uani 1 1 d . .
N1 N -0.14003(18) 0.0840(2) 0.64679(11) 0.0406(4) Uani 1 1 d . .
O1 O 0.03872(19) -0.0495(2) 0.74971(12) 0.0643(5) Uani 1 1 d . .
O2 O -0.25003(18) 0.2442(2) 0.51795(12) 0.0588(4) Uani 1 1 d . .
C1 C 0.0088(2) 0.0422(3) 0.68016(15) 0.0433(5) Uani 1 1 d . .
C2 C -0.1390(2) 0.1921(3) 0.56142(14) 0.0408(5) Uani 1 1 d . .
C3 C 0.0230(2) 0.2212(2) 0.54187(14) 0.0400(4) Uani 1 1 d . .
C4 C 0.1108(2) 0.1329(2) 0.61185(14) 0.0405(5) Uani 1 1 d . .
C5 C 0.2668(2) 0.1389(3) 0.61127(17) 0.0543(6) Uani 1 1 d . .
H5 H 0.3258 0.0793 0.6583 0.065 Uiso 1 1 calc R U
C6 C 0.3323(3) 0.2369(3) 0.5381(2) 0.0621(7) Uani 1 1 d . .
H6 H 0.4376 0.2430 0.5356 0.075 Uiso 1 1 calc R U
C7 C 0.2450(3) 0.3259(3) 0.46867(18) 0.0597(6) Uani 1 1 d . .
H7 H 0.2925 0.3917 0.4207 0.072 Uiso 1 1 calc R U
C8 C 0.0883(3) 0.3191(3) 0.46902(16) 0.0502(5) Uani 1 1 d . .
H8 H 0.0292 0.3784 0.4218 0.060 Uiso 1 1 calc R U
C9 C -0.3374(2) 0.1559(3) 0.78751(16) 0.0559(6) Uani 1 1 d . .
H9 H -0.2479 0.1778 0.8311 0.067 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'
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'
F F 0.0171 0.0103 '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
N1 S1 C9 98.57(10)
C1 N1 C2 111.49(16)
C1 N1 S1 123.94(14)
C2 N1 S1 124.23(14)
O1 C1 N1 124.61(19)
O1 C1 C4 129.82(19)
N1 C1 C4 105.58(17)
O2 C2 N1 124.75(19)
O2 C2 C3 130.17(19)
N1 C2 C3 105.08(16)
C8 C3 C4 121.26(19)
C8 C3 C2 129.41(19)
C4 C3 C2 109.33(17)
C5 C4 C3 121.41(19)
C5 C4 C1 130.1(2)
C3 C4 C1 108.52(17)
C4 C5 C6 117.3(2)
C4 C5 H5 121.3
C6 C5 H5 121.3
C7 C6 C5 121.4(2)
C7 C6 H6 119.3
C5 C6 H6 119.3
C6 C7 C8 121.2(2)
C6 C7 H7 119.4
C8 C7 H7 119.4
C3 C8 C7 117.4(2)
C3 C8 H8 121.3
C7 C8 H8 121.3
F2 C9 F1 106.5(2)
F2 C9 S1 105.95(17)
F1 C9 S1 111.04(16)
F2 C9 H9 111.1
F1 C9 H9 111.1
S1 C9 H9 111.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N1 1.6806(16)
S1 C9 1.798(2)
F1 C9 1.339(3)
F2 C9 1.331(3)
N1 C1 1.411(3)
N1 C2 1.418(2)
O1 C1 1.197(3)
O2 C2 1.195(2)
C1 C4 1.478(3)
C2 C3 1.474(3)
C3 C8 1.375(3)
C3 C4 1.382(3)
C4 C5 1.375(3)
C5 C6 1.379(3)
C5 H5 0.9300
C6 C7 1.378(4)
C6 H6 0.9300
C7 C8 1.382(3)
C7 H7 0.9300
C8 H8 0.9300
C9 H9 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O2 0.98 2.54 3.217(3) 125.9 4_566
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
C9 S1 N1 C1 94.35(17)
C9 S1 N1 C2 -92.96(17)
C2 N1 C1 O1 -178.7(2)
S1 N1 C1 O1 -5.1(3)
C2 N1 C1 C4 1.0(2)
S1 N1 C1 C4 174.49(13)
C1 N1 C2 O2 179.02(19)
S1 N1 C2 O2 5.5(3)
C1 N1 C2 C3 -1.0(2)
S1 N1 C2 C3 -174.44(13)
O2 C2 C3 C8 1.4(4)
N1 C2 C3 C8 -178.65(19)
O2 C2 C3 C4 -179.4(2)
N1 C2 C3 C4 0.6(2)
C8 C3 C4 C5 -0.2(3)
C2 C3 C4 C5 -179.51(18)
C8 C3 C4 C1 179.31(18)
C2 C3 C4 C1 0.0(2)
O1 C1 C4 C5 -1.5(4)
N1 C1 C4 C5 178.9(2)
O1 C1 C4 C3 179.0(2)
N1 C1 C4 C3 -0.6(2)
C3 C4 C5 C6 0.1(3)
C1 C4 C5 C6 -179.3(2)
C4 C5 C6 C7 0.3(3)
C5 C6 C7 C8 -0.6(4)
C4 C3 C8 C7 -0.1(3)
C2 C3 C8 C7 179.0(2)
C6 C7 C8 C3 0.5(3)
N1 S1 C9 F2 -172.63(16)
N1 S1 C9 F1 72.15(17)
