#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:52:06 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180402 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/71/7207109.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_7207109
loop_
_publ_author_name
'Shivakumar, Kota'
'Vidyasagar, Adiyala'
'Naidu, Andra'
'Gonnade, Rajesh G.'
'Sureshan, Kana M.'
_publ_section_title
;
 Strength from weakness: The role of CH…N hydrogen bond in the
 formation of wave-like topology in crystals of aza-heterocycles
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              519
_journal_paper_doi               10.1039/c1ce05997a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C16 H10 N2 S'
_chemical_formula_sum            'C16 H10 N2 S'
_chemical_formula_weight         262.32
_chemical_name_systematic
;
?
;
_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                 96.449(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9434(11)
_cell_length_b                   21.648(6)
_cell_length_c                   14.748(4)
_cell_measurement_reflns_used    1776
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.34
_cell_volume                     1251.0(6)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Phi and Omega Scan'
_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  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8909
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.8859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0321P)²+1.7067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1233
_reflns_number_gt                1930
_reflns_number_total             2209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05997a.txt
_cod_data_source_block           kms6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7207109
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
S1 S 1.1162(2) 0.33779(4) 0.78932(5) 0.0181(2) Uani 1 1 d
N1 N 0.7712(6) 0.43190(11) 0.70159(17) 0.0157(6) Uani 1 1 d
N2 N 1.4450(7) 0.41799(12) 0.99322(19) 0.0256(7) Uani 1 1 d
C4 C 0.9922(8) 0.51813(15) 0.8387(2) 0.0185(7) Uani 1 1 d
C3 C 1.0800(8) 0.45677(14) 0.8471(2) 0.0168(7) Uani 1 1 d
C2 C 0.9678(8) 0.41487(14) 0.7744(2) 0.0161(7) Uani 1 1 d
C8 C 0.4658(8) 0.51100(15) 0.6136(2) 0.0176(7) Uani 1 1 d
C7 C 0.3828(8) 0.57181(15) 0.5992(2) 0.0184(7) Uani 1 1 d
C6 C 0.4974(8) 0.61693(15) 0.6643(2) 0.0199(7) Uani 1 1 d
C5 C 0.6919(8) 0.60046(14) 0.7430(2) 0.0179(7) Uani 1 1 d
C10 C 0.7881(8) 0.53816(14) 0.7591(2) 0.0161(7) Uani 1 1 d
C9 C 0.6771(8) 0.49280(14) 0.6925(2) 0.0148(7) Uani 1 1 d
C11 C 1.2835(8) 0.43488(14) 0.9283(2) 0.0189(7) Uani 1 1 d
C12 C 0.9987(8) 0.30247(14) 0.6816(2) 0.0156(7) Uani 1 1 d
C13 C 0.8250(8) 0.24658(15) 0.6807(2) 0.0201(7) Uani 1 1 d
C14 C 0.7607(9) 0.21342(16) 0.6002(2) 0.0231(8) Uani 1 1 d
C15 C 0.8634(9) 0.23645(15) 0.5203(2) 0.0230(8) Uani 1 1 d
C16 C 1.0355(8) 0.29279(15) 0.5208(2) 0.0215(7) Uani 1 1 d
C17 C 1.1085(8) 0.32547(15) 0.6012(2) 0.0182(7) Uani 1 1 d
H4 H 1.068(8) 0.5479(14) 0.886(2) 0.016(8) Uiso 1 1 d
H8 H 0.393(9) 0.4811(17) 0.573(2) 0.032(10) Uiso 1 1 d
H7 H 0.243(8) 0.5835(14) 0.547(2) 0.016(8) Uiso 1 1 d
H6 H 0.434(7) 0.6566(15) 0.652(2) 0.010(8) Uiso 1 1 d
H5 H 0.780(8) 0.6289(15) 0.787(2) 0.019(9) Uiso 1 1 d
H13 H 0.752(8) 0.2328(14) 0.738(2) 0.018(8) Uiso 1 1 d
H14 H 0.652(9) 0.1764(17) 0.599(2) 0.026(10) Uiso 1 1 d
H15 H 0.815(8) 0.2131(15) 0.465(2) 0.018(8) Uiso 1 1 d
H16 H 1.126(9) 0.3070(15) 0.467(2) 0.026(9) Uiso 1 1 d
H17 H 1.235(8) 0.3624(16) 0.605(2) 0.020(9) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 S1 C12 104.16(14)
C2 N1 C9 118.7(3)
C3 C4 C10 119.0(3)
C3 C4 H4 121.4(18)
C10 C4 H4 119.6(18)
C4 C3 C2 119.3(3)
C4 C3 C11 120.2(3)
C2 C3 C11 120.5(3)
N1 C2 C3 122.7(3)
N1 C2 S1 121.7(2)
C3 C2 S1 115.6(2)
C7 C8 C9 120.4(3)
C7 C8 H8 122(2)
C9 C8 H8 118(2)
C8 C7 C6 120.6(3)
C8 C7 H7 119.9(19)
C6 C7 H7 119.4(19)
C5 C6 C7 120.3(3)
C5 C6 H6 122.0(19)
C7 C6 H6 117.6(19)
C6 C5 C10 120.5(3)
C6 C5 H5 123(2)
C10 C5 H5 116(2)
C5 C10 C4 123.3(3)
C5 C10 C9 119.1(3)
C4 C10 C9 117.6(3)
N1 C9 C8 118.5(3)
N1 C9 C10 122.5(3)
C8 C9 C10 119.0(3)
N2 C11 C3 179.3(4)
C13 C12 C17 120.0(3)
C13 C12 S1 117.6(2)
C17 C12 S1 122.0(2)
C14 C13 C12 120.2(3)
C14 C13 H13 122.8(19)
C12 C13 H13 117.0(19)
C15 C14 C13 120.0(3)
C15 C14 H14 119(2)
C13 C14 H14 121(2)
C14 C15 C16 120.0(3)
C14 C15 H15 119.2(19)
C16 C15 H15 120.7(19)
C17 C16 C15 120.3(3)
C17 C16 H16 119(2)
C15 C16 H16 120(2)
C16 C17 C12 119.4(3)
C16 C17 H17 123(2)
C12 C17 H17 118(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.774(3)
S1 C12 1.777(3)
N1 C2 1.305(4)
N1 C9 1.372(4)
N2 C11 1.149(4)
C4 C3 1.375(4)
C4 C10 1.415(4)
C4 H4 0.97(3)
C3 C2 1.436(4)
C3 C11 1.444(4)
C8 C7 1.367(4)
C8 C9 1.410(4)
C8 H8 0.91(4)
C7 C6 1.408(5)
C7 H7 0.93(3)
C6 C5 1.364(5)
C6 H6 0.91(3)
C5 C10 1.414(4)
C5 H5 0.93(3)
C10 C9 1.423(4)
C12 C13 1.389(4)
C12 C17 1.399(4)
C13 C14 1.386(5)
C13 H13 0.96(3)
C14 C15 1.381(5)
C14 H14 0.91(4)
C15 C16 1.395(5)
C15 H15 0.97(3)
C16 C17 1.384(4)
C16 H16 0.96(3)
C17 H17 0.94(3)
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
C10 C4 C3 C2 1.1(4)
C10 C4 C3 C11 -179.0(3)
C9 N1 C2 C3 2.3(4)
C9 N1 C2 S1 -177.3(2)
C4 C3 C2 N1 -3.2(5)
C11 C3 C2 N1 176.9(3)
C4 C3 C2 S1 176.4(2)
C11 C3 C2 S1 -3.5(4)
C12 S1 C2 N1 9.6(3)
C12 S1 C2 C3 -170.0(2)
C9 C8 C7 C6 -2.1(5)
C8 C7 C6 C5 -0.3(5)
C7 C6 C5 C10 1.6(5)
C6 C5 C10 C4 179.3(3)
C6 C5 C10 C9 -0.4(5)
C3 C4 C10 C5 -178.2(3)
C3 C4 C10 C9 1.5(4)
C2 N1 C9 C8 179.8(3)
C2 N1 C9 C10 0.5(4)
C7 C8 C9 N1 -176.1(3)
C7 C8 C9 C10 3.2(4)
C5 C10 C9 N1 177.3(3)
C4 C10 C9 N1 -2.4(4)
C5 C10 C9 C8 -1.9(4)
C4 C10 C9 C8 178.3(3)
C2 S1 C12 C13 -129.7(2)
C2 S1 C12 C17 57.6(3)
C17 C12 C13 C14 0.1(5)
S1 C12 C13 C14 -172.7(3)
C12 C13 C14 C15 -1.2(5)
C13 C14 C15 C16 0.7(5)
C14 C15 C16 C17 0.9(5)
C15 C16 C17 C12 -2.0(5)
C13 C12 C17 C16 1.5(5)
S1 C12 C17 C16 174.0(2)
