#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:06:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180490 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/59/7215938.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_7215938
loop_
_publ_author_name
'Thakuria, Ranjit'
'Nath, Naba K.'
'Roy, Saikat'
'Nangia, Ashwini'
_publ_section_title
;
 Polymorphism and isostructurality in sulfonylhydrazones
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              4681
_journal_paper_doi               10.1039/c3ce42301h
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C20 H16 I2 N2 O2 S'
_chemical_formula_sum            'C20 H16 I2 N2 O2 S'
_chemical_formula_weight         602.21
_chemical_melting_point          522(2)
_chemical_name_common            'methyldiiodo sulfonylhydrazone'
_chemical_name_systematic
; 
 methyldiiodo sulfonylhydrazone 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 96.670(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6335(16)
_cell_length_b                   11.6089(16)
_cell_length_c                   15.843(2)
_cell_measurement_reflns_used    6494
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.49
_cell_volume                     2125.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21633
_diffrn_reflns_theta_full        26.16
_diffrn_reflns_theta_max         26.16
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    3.075
_exptl_absorpt_correction_T_max  0.7485
_exptl_absorpt_correction_T_min  0.3086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.798
_refine_diff_density_min         -1.257
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0498P)²+3.1330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                3678
_reflns_number_total             4235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce42301h.txt
_cod_data_source_block           MISH
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P21/c  '
_cod_database_code               7215938
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.6204(4) 0.3751(4) 0.2961(3) 0.0589(11) Uani 1 1 d .
C2 C 0.6071(4) 0.4916(5) 0.2839(3) 0.0704(13) Uani 1 1 d .
H2 H 0.5408 0.5193 0.2518 0.084 Uiso 1 1 calc R
C3 C 0.6903(4) 0.5687(4) 0.3184(3) 0.0614(11) Uani 1 1 d .
H3 H 0.6803 0.6474 0.3093 0.074 Uiso 1 1 calc R
C4 C 0.7876(3) 0.5281(3) 0.3661(2) 0.0443(8) Uani 1 1 d .
C5 C 0.8029(4) 0.4118(4) 0.3796(3) 0.0651(12) Uani 1 1 d .
H5 H 0.8691 0.3843 0.4119 0.078 Uiso 1 1 calc R
C6 C 0.7190(4) 0.3368(4) 0.3447(3) 0.0695(12) Uani 1 1 d .
H6 H 0.7290 0.2582 0.3542 0.083 Uiso 1 1 calc R
C7 C 1.1109(3) 0.5378(3) 0.2654(2) 0.0424(8) Uani 1 1 d .
C8 C 1.1934(3) 0.4642(3) 0.3210(2) 0.0436(8) Uani 1 1 d .
C9 C 1.2756(4) 0.5164(4) 0.3797(3) 0.0588(10) Uani 1 1 d .
H9 H 1.2784 0.5962 0.3842 0.071 Uiso 1 1 calc R
C10 C 1.3530(4) 0.4496(4) 0.4315(3) 0.0662(12) Uani 1 1 d .
H10 H 1.4082 0.4844 0.4705 0.079 Uiso 1 1 calc R
C11 C 1.3480(3) 0.3315(4) 0.4250(3) 0.0543(10) Uani 1 1 d .
C12 C 1.2647(4) 0.2787(4) 0.3687(3) 0.0547(10) Uani 1 1 d .
H12 H 1.2603 0.1988 0.3660 0.066 Uiso 1 1 calc R
C13 C 1.1880(4) 0.3455(3) 0.3164(2) 0.0493(9) Uani 1 1 d .
H13 H 1.1325 0.3103 0.2779 0.059 Uiso 1 1 calc R
C14 C 1.1282(3) 0.5517(3) 0.1748(2) 0.0441(8) Uani 1 1 d .
C15 C 1.0492(4) 0.6124(3) 0.1184(3) 0.0511(9) Uani 1 1 d .
H15 H 0.9829 0.6430 0.1373 0.061 Uiso 1 1 calc R
C16 C 1.0687(4) 0.6277(4) 0.0347(3) 0.0556(10) Uani 1 1 d .
H16 H 1.0152 0.6674 -0.0027 0.067 Uiso 1 1 calc R
C17 C 1.1674(4) 0.5839(4) 0.0069(2) 0.0533(9) Uani 1 1 d .
C18 C 1.2459(4) 0.5228(4) 0.0606(3) 0.0638(11) Uani 1 1 d .
H18 H 1.3119 0.4924 0.0410 0.077 Uiso 1 1 calc R
C19 C 1.2260(4) 0.5068(4) 0.1445(3) 0.0580(10) Uani 1 1 d .
H19 H 1.2791 0.4652 0.1810 0.070 Uiso 1 1 calc R
C20 C 0.5324(5) 0.2911(6) 0.2558(4) 0.0859(17) Uani 1 1 d .
H20A H 0.5626 0.2531 0.2092 0.129 Uiso 1 1 calc R
H20B H 0.4628 0.3315 0.2354 0.129 Uiso 1 1 calc R
H20C H 0.5158 0.2349 0.2972 0.129 Uiso 1 1 calc R
H1A H 1.040(4) 0.538(4) 0.400(3) 0.039(12) Uiso 1 1 d .
I1 I 1.47179(3) 0.23244(4) 0.49995(2) 0.08088(15) Uani 1 1 d .
I2 I 1.20019(4) 0.60982(3) -0.11925(2) 0.08052(15) Uani 1 1 d .
N1 N 1.0169(3) 0.5838(3) 0.3782(2) 0.0476(8) Uani 1 1 d .
N2 N 1.0268(3) 0.5930(3) 0.29255(19) 0.0450(7) Uani 1 1 d .
O1 O 0.8667(3) 0.7365(2) 0.37800(19) 0.0574(7) Uani 1 1 d .
O2 O 0.9141(3) 0.6065(2) 0.50049(16) 0.0517(6) Uani 1 1 d .
S1 S 0.89469(8) 0.62430(8) 0.41040(5) 0.0431(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'
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'
I I -0.4742 1.8119 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 118.0(4)
C2 C1 C20 121.3(5)
C6 C1 C20 120.6(5)
C1 C2 C3 121.3(4)
C1 C2 H2 119.4
C3 C2 H2 119.4
C4 C3 C2 119.4(4)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C5 120.5(4)
C3 C4 S1 120.3(3)
C5 C4 S1 119.2(3)
C6 C5 C4 119.0(4)
C6 C5 H5 120.5
C4 C5 H5 120.5
C5 C6 C1 121.8(4)
C5 C6 H6 119.1
C1 C6 H6 119.1
N2 C7 C14 117.7(3)
N2 C7 C8 123.4(3)
C14 C7 C8 118.9(3)
C13 C8 C9 119.5(4)
C13 C8 C7 121.2(3)
C9 C8 C7 119.3(4)
C10 C9 C8 120.1(4)
C10 C9 H9 119.9
C8 C9 H9 119.9
C11 C10 C9 119.7(4)
C11 C10 H10 120.2
C9 C10 H10 120.2
C10 C11 C12 120.7(4)
C10 C11 I1 118.9(3)
C12 C11 I1 120.4(3)
C11 C12 C13 119.6(4)
C11 C12 H12 120.2
C13 C12 H12 120.2
C8 C13 C12 120.4(4)
C8 C13 H13 119.8
C12 C13 H13 119.8
C19 C14 C15 118.3(4)
C19 C14 C7 120.2(3)
C15 C14 C7 121.5(3)
C16 C15 C14 120.6(4)
C16 C15 H15 119.7
C14 C15 H15 119.7
C17 C16 C15 119.8(4)
C17 C16 H16 120.1
C15 C16 H16 120.1
C18 C17 C16 120.9(4)
C18 C17 I2 118.9(3)
C16 C17 I2 120.3(3)
C17 C18 C19 119.4(4)
C17 C18 H18 120.3
C19 C18 H18 120.3
C14 C19 C18 121.0(4)
C14 C19 H19 119.5
C18 C19 H19 119.5
C1 C20 H20A 109.5
C1 C20 H20B 109.5
H20A C20 H20B 109.5
C1 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
N2 N1 S1 117.4(3)
N2 N1 H1A 119(4)
S1 N1 H1A 113(4)
C7 N2 N1 116.4(3)
O1 S1 O2 119.56(17)
O1 S1 N1 108.8(2)
O2 S1 N1 103.15(17)
O1 S1 C4 108.38(19)
O2 S1 C4 109.18(17)
N1 S1 C4 107.13(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.373(7)
C1 C6 1.378(7)
C1 C20 1.501(7)
C2 C3 1.384(7)
C2 H2 0.9300
C3 C4 1.370(6)
C3 H3 0.9300
C4 C5 1.375(6)
C4 S1 1.757(4)
C5 C6 1.375(7)
C5 H5 0.9300
C6 H6 0.9300
C7 N2 1.284(5)
C7 C14 1.482(5)
C7 C8 1.493(5)
C8 C13 1.381(6)
C8 C9 1.393(6)
C9 C10 1.383(6)
C9 H9 0.9300
C10 C11 1.376(7)
C10 H10 0.9300
C11 C12 1.381(6)
C11 I1 2.100(4)
C12 C13 1.383(6)
C12 H12 0.9300
C13 H13 0.9300
C14 C19 1.387(6)
C14 C15 1.396(5)
C15 C16 1.382(6)
C15 H15 0.9300
C16 C17 1.374(6)
C16 H16 0.9300
C17 C18 1.372(7)
C17 I2 2.099(4)
C18 C19 1.388(6)
C18 H18 0.9300
C19 H19 0.9300
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
N1 N2 1.379(4)
N1 S1 1.635(4)
N1 H1A 0.67(4)
O1 S1 1.424(3)
O2 S1 1.434(3)
