#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/49/2214976.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2214976
loop_
_publ_author_name
'Saikat Roy'
'Ashwini Nangia'
_publ_section_title
;
 p-Tosylhydrazine: a redetermination from single-crystal data at
 100 K
;
_journal_coeditor_code           BI2204
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3696
_journal_page_last               o3696
_journal_paper_doi               10.1107/S1600536807037518
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C7 H10 N2 O2 S'
_chemical_formula_moiety         'C7 H10 N2 O2 S'
_chemical_formula_sum            'C7 H10 N2 O2 S'
_chemical_formula_weight         186.23
_chemical_melting_point          382
_chemical_name_common            4-tosylsulphonylhydrazine
_chemical_name_systematic
;
4-Methylbenzenesulfonohydrazide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 100.2600(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4166(8)
_cell_length_b                   5.6056(5)
_cell_length_c                   17.9484(17)
_cell_measurement_reflns_used    5282
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.31
_cell_volume                     833.27(13)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL and X-SEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8195
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.297
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1641
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.299
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0604
_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)+(0.0212P)²+1.9226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1170
_reflns_number_gt                1584
_reflns_number_total             1641
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2204.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2214976
_cod_database_fobs_code          2214976
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.27606(8) 0.14178(13) 0.17916(4) 0.0144(2) Uani d . 1
O O1 0.4359(2) 0.0492(4) 0.20362(12) 0.0207(5) Uani d . 1
O O2 0.1440(2) -0.0239(4) 0.16470(12) 0.0184(5) Uani d . 1
N N1 0.2469(3) 0.3220(5) 0.24704(14) 0.0173(6) Uani d D 1
H H1 0.346(3) 0.402(5) 0.2665(17) 0.015(8) Uiso d D 1
N N2 0.1052(3) 0.4620(5) 0.22597(16) 0.0191(6) Uani d . 1
H H2A 0.130(4) 0.605(7) 0.215(2) 0.026(10) Uiso d . 1
H H2B 0.056(4) 0.467(7) 0.266(2) 0.027(10) Uiso d . 1
C C1 0.2708(3) 0.3161(5) 0.09705(16) 0.0149(6) Uani d . 1
C C2 0.3625(4) 0.5216(6) 0.10103(17) 0.0179(6) Uani d . 1
H H2 0.4279 0.5681 0.1475 0.021 Uiso calc R 1
C C3 0.3581(4) 0.6590(6) 0.03662(17) 0.0204(7) Uani d . 1
H H3 0.4215 0.8001 0.0392 0.024 Uiso calc R 1
C C4 0.2624(4) 0.5941(6) -0.03207(17) 0.0182(6) Uani d . 1
C C5 0.1721(4) 0.3860(6) -0.03418(18) 0.0252(7) Uani d . 1
H H5 0.1070 0.3383 -0.0806 0.030 Uiso calc R 1
C C6 0.1747(4) 0.2466(6) 0.02964(17) 0.0207(7) Uani d . 1
H H6 0.1116 0.1053 0.0273 0.025 Uiso calc R 1
C C7 0.2553(4) 0.7451(7) -0.10152(18) 0.0256(7) Uani d . 1
H H7A 0.2719 0.6444 -0.1441 0.038 Uiso calc R 1
H H7B 0.3400 0.8671 -0.0923 0.038 Uiso calc R 1
H H7C 0.1495 0.8225 -0.1136 0.038 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0148(4) 0.0132(4) 0.0152(4) 0.0006(3) 0.0022(3) 0.0006(3)
O1 0.0182(11) 0.0210(11) 0.0221(12) 0.0033(9) 0.0017(9) 0.0038(9)
O2 0.0199(11) 0.0146(11) 0.0210(11) 0.0003(9) 0.0045(9) 0.0008(9)
C5 0.0239(16) 0.0307(19) 0.0185(16) 0.0005(14) -0.0029(13) -0.0018(14)
C1 0.0130(13) 0.0165(15) 0.0148(14) 0.0025(11) 0.0017(11) 0.0025(12)
N1 0.0162(12) 0.0191(14) 0.0159(12) -0.0016(11) 0.0008(10) -0.0001(10)
N2 0.0186(13) 0.0181(14) 0.0216(14) 0.0017(11) 0.0058(11) -0.0009(12)
C2 0.0168(14) 0.0209(16) 0.0155(14) -0.0011(12) 0.0015(12) -0.0037(12)
C6 0.0198(15) 0.0197(16) 0.0213(16) -0.0022(13) -0.0002(12) -0.0004(13)
C3 0.0197(15) 0.0192(16) 0.0229(16) -0.0009(13) 0.0053(12) 0.0015(13)
C7 0.0247(17) 0.0330(19) 0.0193(16) 0.0039(15) 0.0042(13) 0.0066(14)
C4 0.0171(14) 0.0201(16) 0.0182(15) 0.0070(12) 0.0054(12) 0.0022(12)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 118.33(13)
O1 S1 N1 104.61(13)
O2 S1 N1 108.68(13)
O1 S1 C1 109.81(13)
O2 S1 C1 107.70(13)
N1 S1 C1 107.22(14)
C6 C5 C4 121.6(3)
C6 C5 H5 119.2
C4 C5 H5 119.2
C2 C1 C6 120.9(3)
C2 C1 S1 119.2(2)
C6 C1 S1 119.9(2)
N2 N1 S1 111.91(19)
N2 N1 H1 118(2)
S1 N1 H1 108.8(19)
N1 N2 H2A 110(2)
N1 N2 H2B 107(2)
H2A N2 H2B 109(3)
C1 C2 C3 119.3(3)
C1 C2 H2 120.3
C3 C2 H2 120.3
C5 C6 C1 119.0(3)
C5 C6 H6 120.5
C1 C6 H6 120.5
C2 C3 C4 121.2(3)
C2 C3 H3 119.4
C4 C3 H3 119.4
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 C4 C3 118.0(3)
C5 C4 C7 120.7(3)
C3 C4 C7 121.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.436(2)
S1 O2 1.436(2)
S1 N1 1.635(3)
S1 C1 1.762(3)
C5 C6 1.384(4)
C5 C4 1.389(5)
C5 H5 0.950
C1 C2 1.381(4)
C1 C6 1.386(4)
N1 N2 1.422(4)
N1 H1 0.96(2)
N2 H2A 0.86(4)
N2 H2B 0.89(4)
C2 C3 1.384(4)
C2 H2 0.950
C6 H6 0.950
C3 C4 1.395(4)
C3 H3 0.950
C7 C4 1.499(4)
C7 H7A 0.980
C7 H7B 0.980
C7 H7C 0.980
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O1 2_655 0.96(2) 2.00(2) 2.948(3) 173(3)
N2 H2A O2 1_565 0.86(4) 2.28(4) 3.122(4) 167(3)
N2 H2B O2 2 0.89(4) 2.27(4) 3.118(3) 160(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14566
