#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/10/7021032.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_7021032
loop_
_publ_author_name
'Melen, Rebecca L.'
'Eisler, Dana J.'
'Hewitt, Rachel A.'
'Rawson, Jeremy M.'
_publ_section_title
;
 Synthesis and structural studies on thioimides, R(2)C[double bond, length
 as m-dash]NSR and sulfur diimides, R(2)C[double bond, length as
 m-dash]NSN[double bond, length as m-dash]CR(2).
;
_journal_issue                   11
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3888
_journal_page_last               3895
_journal_paper_doi               10.1039/c2dt32878j
_journal_volume                  42
_journal_year                    2013
_chemical_formula_moiety         'C26 H16 N2 S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C26.5 H17 Cl N2 S'
_chemical_formula_weight         430.93
_chemical_name_systematic
;
?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.921(5)
_cell_length_b                   7.7572(16)
_cell_length_c                   19.322(4)
_cell_measurement_reflns_used    36212
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     4035.0(14)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'thin slice ω and φ 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  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33865
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0484P)²+3.0822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2800
_reflns_number_total             3557
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt32878j.txt
_cod_data_source_block           compound_4
_cod_original_cell_volume        4035.1(14)
_cod_original_formula_sum        'C26.50 H17 Cl N2 S'
_cod_database_code               7021032
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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
S1 S 0.45531(2) 0.64815(8) 0.53874(3) 0.02971(17) Uani 1 1 d .
N1 N 0.41249(7) 0.5533(2) 0.58695(10) 0.0283(5) Uani 1 1 d .
N2 N 0.49604(7) 0.6830(2) 0.60147(10) 0.0299(5) Uani 1 1 d .
C1 C 0.37085(8) 0.5002(3) 0.55985(11) 0.0256(5) Uani 1 1 d .
C2 C 0.33398(8) 0.4089(3) 0.60256(11) 0.0249(5) Uani 1 1 d .
C3 C 0.33479(9) 0.3668(3) 0.67219(11) 0.0293(5) Uani 1 1 d .
H3A H 0.3620 0.3990 0.7007 0.035 Uiso 1 1 calc R
C4 C 0.29478(10) 0.2763(3) 0.69938(12) 0.0337(6) Uani 1 1 d .
H4A H 0.2946 0.2468 0.7471 0.040 Uiso 1 1 calc R
C5 C 0.25513(9) 0.2285(3) 0.65795(12) 0.0332(6) Uani 1 1 d .
H5A H 0.2282 0.1665 0.6776 0.040 Uiso 1 1 calc R
C6 C 0.25427(9) 0.2699(3) 0.58813(12) 0.0287(5) Uani 1 1 d .
H6A H 0.2270 0.2367 0.5599 0.034 Uiso 1 1 calc R
C7 C 0.29379(8) 0.3605(3) 0.56021(11) 0.0243(5) Uani 1 1 d .
C8 C 0.30401(8) 0.4204(3) 0.48949(11) 0.0255(5) Uani 1 1 d .
C9 C 0.27678(9) 0.4015(3) 0.42909(12) 0.0309(5) Uani 1 1 d .
H9A H 0.2460 0.3414 0.4291 0.037 Uiso 1 1 calc R
C10 C 0.29566(9) 0.4729(3) 0.36825(12) 0.0372(6) Uani 1 1 d .
H10A H 0.2774 0.4618 0.3264 0.045 Uiso 1 1 calc R
C11 C 0.34064(10) 0.5598(3) 0.36804(13) 0.0372(6) Uani 1 1 d .
H11A H 0.3525 0.6085 0.3261 0.045 Uiso 1 1 calc R
C12 C 0.36853(9) 0.5770(3) 0.42783(11) 0.0317(5) Uani 1 1 d .
H12A H 0.3995 0.6358 0.4272 0.038 Uiso 1 1 calc R
C13 C 0.35031(8) 0.5066(3) 0.48880(11) 0.0254(5) Uani 1 1 d .
C14 C 0.53724(8) 0.7648(3) 0.58906(12) 0.0265(5) Uani 1 1 d .
C15 C 0.55952(8) 0.8418(3) 0.52572(11) 0.0264(5) Uani 1 1 d .
C16 C 0.54327(9) 0.8485(3) 0.45756(12) 0.0312(5) Uani 1 1 d .
H16A H 0.5118 0.8026 0.4449 0.037 Uiso 1 1 calc R
C17 C 0.57388(10) 0.9236(3) 0.40831(12) 0.0343(6) Uani 1 1 d .
H17A H 0.5632 0.9296 0.3615 0.041 Uiso 1 1 calc R
C18 C 0.61994(9) 0.9902(3) 0.42639(13) 0.0348(6) Uani 1 1 d .
H18A H 0.6406 1.0391 0.3917 0.042 Uiso 1 1 calc R
C19 C 0.63630(9) 0.9864(3) 0.49461(12) 0.0296(5) Uani 1 1 d .
H19A H 0.6676 1.0333 0.5070 0.036 Uiso 1 1 calc R
C20 C 0.60576(8) 0.9124(3) 0.54399(11) 0.0256(5) Uani 1 1 d .
C21 C 0.61391(8) 0.8862(3) 0.61879(11) 0.0254(5) Uani 1 1 d .
C22 C 0.65278(9) 0.9321(3) 0.66148(12) 0.0327(6) Uani 1 1 d .
H22A H 0.6803 0.9950 0.6438 0.039 Uiso 1 1 calc R
C23 C 0.65105(9) 0.8846(3) 0.73111(12) 0.0356(6) Uani 1 1 d .
H23A H 0.6777 0.9149 0.7610 0.043 Uiso 1 1 calc R
C24 C 0.61100(9) 0.7939(3) 0.75706(12) 0.0355(6) Uani 1 1 d .
H24A H 0.6106 0.7614 0.8045 0.043 Uiso 1 1 calc R
C25 C 0.57148(9) 0.7499(3) 0.71475(12) 0.0318(6) Uani 1 1 d .
H25A H 0.5437 0.6892 0.7328 0.038 Uiso 1 1 calc R
C26 C 0.57322(8) 0.7959(3) 0.64554(12) 0.0260(5) Uani 1 1 d .
C27 C 0.5000 0.3478(5) 0.7500 0.0543(11) Uani 1 2 d S
H27A H 0.5167 0.4228 0.7843 0.065 Uiso 0.50 1 calc PR
H27B H 0.4833 0.4228 0.7157 0.065 Uiso 0.50 1 calc PR
Cl1 Cl 0.54467(3) 0.22027(11) 0.70780(4) 0.0605(2) Uani 1 1 d .
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'
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
N1 S1 N2 96.99(10) .
C1 N1 S1 120.88(17) .
C14 N2 S1 120.62(17) .
N1 C1 C2 120.4(2) .
N1 C1 C13 133.1(2) .
C2 C1 C13 106.49(18) .
C3 C2 C7 120.9(2) .
C3 C2 C1 130.3(2) .
C7 C2 C1 108.72(19) .
C2 C3 C4 118.3(2) .
C5 C4 C3 121.0(2) .
C4 C5 C6 120.9(2) .
C7 C6 C5 118.9(2) .
C6 C7 C2 120.0(2) .
C6 C7 C8 131.8(2) .
C2 C7 C8 108.19(19) .
C9 C8 C13 120.5(2) .
C9 C8 C7 130.6(2) .
C13 C8 C7 108.87(19) .
C8 C9 C10 118.3(2) .
C11 C10 C9 120.9(2) .
C12 C11 C10 121.2(2) .
C11 C12 C13 118.6(2) .
C12 C13 C8 120.4(2) .
C12 C13 C1 131.9(2) .
C8 C13 C1 107.73(19) .
N2 C14 C26 120.2(2) .
N2 C14 C15 133.7(2) .
C26 C14 C15 106.11(18) .
C16 C15 C20 120.2(2) .
C16 C15 C14 131.9(2) .
C20 C15 C14 107.87(18) .
C17 C16 C15 118.6(2) .
C16 C17 C18 121.0(2) .
C17 C18 C19 120.9(2) .
C20 C19 C18 118.3(2) .
C19 C20 C15 121.0(2) .
C19 C20 C21 130.1(2) .
C15 C20 C21 108.92(19) .
C22 C21 C26 120.1(2) .
C22 C21 C20 131.5(2) .
C26 C21 C20 108.31(19) .
C21 C22 C23 118.9(2) .
C24 C23 C22 120.7(2) .
C23 C24 C25 120.7(2) .
C24 C25 C26 118.7(2) .
C25 C26 C21 120.8(2) .
C25 C26 C14 130.4(2) .
C21 C26 C14 108.77(19) .
Cl1 C27 Cl1 111.5(2) 3_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 N1 1.655(2) .
S1 N2 1.657(2) .
N1 C1 1.304(3) .
N2 C14 1.300(3) .
C1 C2 1.472(3) .
C1 C13 1.481(3) .
C2 C3 1.385(3) .
C2 C7 1.408(3) .
C3 C4 1.389(3) .
C4 C5 1.385(3) .
C5 C6 1.387(3) .
C6 C7 1.384(3) .
C7 C8 1.469(3) .
C8 C9 1.386(3) .
C8 C13 1.415(3) .
C9 C10 1.395(3) .
C10 C11 1.386(4) .
C11 C12 1.384(3) .
C12 C13 1.388(3) .
C14 C26 1.479(3) .
C14 C15 1.488(3) .
C15 C16 1.389(3) .
C15 C20 1.405(3) .
C16 C17 1.387(3) .
C17 C18 1.388(3) .
C18 C19 1.390(3) .
C19 C20 1.384(3) .
C20 C21 1.476(3) .
C21 C22 1.379(3) .
C21 C26 1.399(3) .
C22 C23 1.396(3) .
C23 C24 1.381(3) .
C24 C25 1.385(3) .
C25 C26 1.385(3) .
C27 Cl1 1.758(2) 3_656
C27 Cl1 1.758(2) .
