#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/78/7117802.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_7117802
loop_
_publ_author_name
'Masood Ayoub Kaloo'
'Jeyaraman Sankar'
_publ_section_title
;
 Reusable and specific proton transfer signalling by inorganic cyanide in
 solution and solid phase
;
_journal_name_full               Chem.Commun.
_journal_page_first              14528
_journal_paper_doi               10.1039/C5cc05106A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C21 H12 N4, C2 H6 O S'
_chemical_formula_sum            'C23 H18 N4 O S'
_chemical_formula_weight         398.48
_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
_audit_update_record
;
2013-08-27 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.434(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.387(6)
_cell_length_b                   32.39(3)
_cell_length_c                   8.251(7)
_cell_measurement_reflns_used    3082
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.59
_cell_measurement_theta_min      6.09
_cell_volume                     1972(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8156
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         6.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0745
_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)+(0.1321P)²+0.9376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2232
_refine_ls_wR_factor_ref         0.2380
_reflns_number_gt                2374
_reflns_number_total             3473
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05106a2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7117802
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2494(4) -0.13668(10) 1.1055(4) 0.0568(9) Uani 1 1 d . . .
H1A H 0.3055 -0.1153 1.0716 0.068 Uiso 1 1 calc R . .
H1B H 0.3079 -0.1554 1.1599 0.068 Uiso 1 1 calc R . .
N2 N -0.0747(5) -0.20648(11) 1.1795(5) 0.0653(10) Uani 1 1 d . . .
N3 N -0.3678(5) -0.12275(12) 0.9185(5) 0.0670(11) Uani 1 1 d . . .
N4 N 0.0553(4) -0.07721(8) 0.9392(3) 0.0390(7) Uani 1 1 d . . .
C1 C -0.0122(5) -0.17702(12) 1.1335(5) 0.0446(9) Uani 1 1 d . . .
C2 C 0.0719(5) -0.14077(11) 1.0739(4) 0.0402(8) Uani 1 1 d . . .
C3 C -0.0297(4) -0.11237(10) 0.9886(4) 0.0376(8) Uani 1 1 d . . .
C4 C -0.2183(5) -0.11970(11) 0.9525(4) 0.0433(9) Uani 1 1 d . . .
C5 C -0.0303(4) -0.05017(10) 0.8528(4) 0.0369(8) Uani 1 1 d . . .
H5 H -0.1512 -0.0548 0.8221 0.044 Uiso 1 1 calc R . .
C6 C 0.0554(4) -0.01290(10) 0.8022(4) 0.0343(8) Uani 1 1 d . . .
C7 C 0.2335(5) -0.00475(12) 0.8545(4) 0.0428(9) Uani 1 1 d . . .
H7 H 0.2948 -0.0238 0.9208 0.051 Uiso 1 1 calc R . .
C8 C 0.3204(5) 0.03033(11) 0.8112(5) 0.0435(9) Uani 1 1 d . . .
H8 H 0.4389 0.0349 0.8495 0.052 Uiso 1 1 calc R . .
C9 C 0.2345(4) 0.05945(11) 0.7105(4) 0.0396(8) Uani 1 1 d . . .
C10 C 0.3210(5) 0.09615(12) 0.6619(5) 0.0502(10) Uani 1 1 d . . .
H10 H 0.4397 0.1012 0.6987 0.060 Uiso 1 1 calc R . .
C11 C 0.2366(6) 0.12398(12) 0.5639(5) 0.0538(10) Uani 1 1 d . . .
H11 H 0.2980 0.1476 0.5335 0.065 Uiso 1 1 calc R . .
C12 C 0.0556(5) 0.11767(11) 0.5068(5) 0.0449(9) Uani 1 1 d . . .
C13 C -0.0371(6) 0.14645(12) 0.4057(5) 0.0572(11) Uani 1 1 d . . .
H13 H 0.0211 0.1705 0.3753 0.069 Uiso 1 1 calc R . .
C14 C -0.2116(6) 0.13925(13) 0.3522(5) 0.0586(11) Uani 1 1 d . . .
H14 H -0.2709 0.1585 0.2851 0.070 Uiso 1 1 calc R . .
C15 C -0.3003(5) 0.10426(12) 0.3957(5) 0.0504(10) Uani 1 1 d . . .
H15 H -0.4187 0.0998 0.3568 0.060 Uiso 1 1 calc R . .
C16 C -0.2164(5) 0.07529(10) 0.4971(4) 0.0381(8) Uani 1 1 d . . .
C17 C -0.3034(4) 0.03904(11) 0.5455(4) 0.0418(9) Uani 1 1 d . . .
H17 H -0.4223 0.0343 0.5087 0.050 Uiso 1 1 calc R . .
C18 C -0.2208(4) 0.01080(10) 0.6432(4) 0.0393(8) Uani 1 1 d . . .
H18 H -0.2842 -0.0126 0.6728 0.047 Uiso 1 1 calc R . .
C19 C -0.0378(4) 0.01618(10) 0.7021(4) 0.0328(7) Uani 1 1 d . . .
C20 C 0.0533(4) 0.05216(10) 0.6563(4) 0.0343(8) Uani 1 1 d . . .
C21 C -0.0360(4) 0.08183(10) 0.5533(4) 0.0361(8) Uani 1 1 d . . .
C22 C 0.7451(7) 0.25117(17) 0.5767(8) 0.0844(17) Uani 1 1 d . . .
H22A H 0.7647 0.2686 0.6698 0.127 Uiso 1 1 calc R . .
H22B H 0.7366 0.2678 0.4804 0.127 Uiso 1 1 calc R . .
H22C H 0.8445 0.2322 0.5698 0.127 Uiso 1 1 calc R . .
C23 C 0.4002(7) 0.26624(16) 0.6205(7) 0.0784(15) Uani 1 1 d . . .
H23A H 0.2803 0.2566 0.6401 0.118 Uiso 1 1 calc R . .
H23B H 0.3972 0.2829 0.5243 0.118 Uiso 1 1 calc R . .
H23C H 0.4445 0.2824 0.7113 0.118 Uiso 1 1 calc R . .
O1 O 0.5605(4) 0.20199(8) 0.7544(4) 0.0670(9) Uani 1 1 d . . .
S1 S 0.54477(16) 0.22366(3) 0.59476(13) 0.0589(4) 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 H1A 120.0 . .
C2 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C5 N4 C3 120.9(3) . .
N2 C1 C2 178.0(4) . .
N1 C2 C3 123.3(3) . .
N1 C2 C1 117.0(3) . .
C3 C2 C1 119.7(3) . .
C2 C3 N4 117.7(3) . .
C2 C3 C4 120.3(3) . .
N4 C3 C4 122.0(3) . .
N3 C4 C3 175.0(4) . .
N4 C5 C6 121.7(3) . .
N4 C5 H5 119.2 . .
C6 C5 H5 119.2 . .
C7 C6 C19 119.1(3) . .
C7 C6 C5 119.5(3) . .
C19 C6 C5 121.4(3) . .
C8 C7 C6 121.8(3) . .
C8 C7 H7 119.1 . .
C6 C7 H7 119.1 . .
C7 C8 C9 121.0(3) . .
C7 C8 H8 119.5 . .
C9 C8 H8 119.5 . .
C8 C9 C20 118.5(3) . .
C8 C9 C10 122.6(3) . .
C20 C9 C10 118.9(3) . .
C11 C10 C9 122.0(4) . .
C11 C10 H10 119.0 . .
C9 C10 H10 119.0 . .
C10 C11 C12 120.7(4) . .
C10 C11 H11 119.6 . .
C12 C11 H11 119.6 . .
C21 C12 C13 118.7(4) . .
C21 C12 C11 119.2(3) . .
C13 C12 C11 122.1(4) . .
C14 C13 C12 120.5(4) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C13 C14 C15 120.9(4) . .
C13 C14 H14 119.5 . .
C15 C14 H14 119.5 . .
C14 C15 C16 120.9(4) . .
C14 C15 H15 119.5 . .
C16 C15 H15 119.5 . .
C15 C16 C17 122.6(3) . .
C15 C16 C21 119.3(3) . .
C17 C16 C21 118.1(3) . .
C18 C17 C16 122.4(3) . .
C18 C17 H17 118.8 . .
C16 C17 H17 118.8 . .
C17 C18 C19 121.2(3) . .
C17 C18 H18 119.4 . .
C19 C18 H18 119.4 . .
C20 C19 C6 118.9(3) . .
C20 C19 C18 117.8(3) . .
C6 C19 C18 123.3(3) . .
C19 C20 C9 120.8(3) . .
C19 C20 C21 120.3(3) . .
C9 C20 C21 118.9(3) . .
C12 C21 C16 119.6(3) . .
C12 C21 C20 120.3(3) . .
C16 C21 C20 120.1(3) . .
S1 C22 H22A 109.5 . .
S1 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
S1 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
S1 C23 H23A 109.5 . .
S1 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
S1 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
O1 S1 C22 106.4(2) . .
O1 S1 C23 106.6(2) . .
C22 S1 C23 97.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.333(5) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
N2 C1 1.133(5) .
N3 C4 1.132(5) .
N4 C5 1.279(4) .
N4 C3 1.371(4) .
C1 C2 1.425(5) .
C2 C3 1.364(5) .
C3 C4 1.432(5) .
C5 C6 1.433(5) .
C5 H5 0.9300 .
C6 C7 1.392(5) .
C6 C19 1.413(5) .
C7 C8 1.360(5) .
C7 H7 0.9300 .
C8 C9 1.392(5) .
C8 H8 0.9300 .
C9 C20 1.413(5) .
C9 C10 1.416(5) .
C10 C11 1.346(6) .
C10 H10 0.9300 .
C11 C12 1.413(6) .
C11 H11 0.9300 .
C12 C21 1.405(5) .
C12 C13 1.409(6) .
C13 C14 1.365(6) .
C13 H13 0.9300 .
C14 C15 1.365(6) .
C14 H14 0.9300 .
C15 C16 1.386(5) .
C15 H15 0.9300 .
C16 C17 1.404(5) .
C16 C21 1.408(5) .
C17 C18 1.348(5) .
C17 H17 0.9300 .
C18 C19 1.427(5) .
C18 H18 0.9300 .
C19 C20 1.405(5) .
C20 C21 1.426(5) .
C22 S1 1.739(6) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 S1 1.762(5) .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
O1 S1 1.493(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N2 C1 C2 N1 -41(12) . . . .
N2 C1 C2 C3 139(12) . . . .
N1 C2 C3 N4 -2.7(5) . . . .
C1 C2 C3 N4 177.5(3) . . . .
N1 C2 C3 C4 177.0(4) . . . .
C1 C2 C3 C4 -2.8(5) . . . .
C5 N4 C3 C2 177.0(3) . . . .
C5 N4 C3 C4 -2.7(5) . . . .
C2 C3 C4 N3 179(100) . . . .
N4 C3 C4 N3 -1(5) . . . .
C3 N4 C5 C6 179.0(3) . . . .
N4 C5 C6 C7 -3.3(5) . . . .
N4 C5 C6 C19 177.7(3) . . . .
C19 C6 C7 C8 -0.3(5) . . . .
C5 C6 C7 C8 -179.4(3) . . . .
C6 C7 C8 C9 -0.8(6) . . . .
C7 C8 C9 C20 1.2(5) . . . .
C7 C8 C9 C10 -179.5(3) . . . .
C8 C9 C10 C11 179.8(4) . . . .
C20 C9 C10 C11 -0.9(6) . . . .
C9 C10 C11 C12 0.7(6) . . . .
C10 C11 C12 C21 0.0(6) . . . .
C10 C11 C12 C13 179.2(4) . . . .
C21 C12 C13 C14 -1.0(6) . . . .
C11 C12 C13 C14 179.7(4) . . . .
C12 C13 C14 C15 0.3(6) . . . .
C13 C14 C15 C16 0.8(6) . . . .
C14 C15 C16 C17 179.6(4) . . . .
C14 C15 C16 C21 -1.2(6) . . . .
C15 C16 C17 C18 179.5(4) . . . .
C21 C16 C17 C18 0.3(5) . . . .
C16 C17 C18 C19 -0.6(6) . . . .
C7 C6 C19 C20 1.0(5) . . . .
C5 C6 C19 C20 -180.0(3) . . . .
C7 C6 C19 C18 -179.5(3) . . . .
C5 C6 C19 C18 -0.5(5) . . . .
C17 C18 C19 C20 0.7(5) . . . .
C17 C18 C19 C6 -178.8(3) . . . .
C6 C19 C20 C9 -0.6(5) . . . .
C18 C19 C20 C9 179.9(3) . . . .
C6 C19 C20 C21 179.0(3) . . . .
C18 C19 C20 C21 -0.5(5) . . . .
C8 C9 C20 C19 -0.5(5) . . . .
C10 C9 C20 C19 -179.8(3) . . . .
C8 C9 C20 C21 179.9(3) . . . .
C10 C9 C20 C21 0.5(5) . . . .
C13 C12 C21 C16 0.6(5) . . . .
C11 C12 C21 C16 179.9(3) . . . .
C13 C12 C21 C20 -179.6(3) . . . .
C11 C12 C21 C20 -0.3(5) . . . .
C15 C16 C21 C12 0.4(5) . . . .
C17 C16 C21 C12 179.7(3) . . . .
C15 C16 C21 C20 -179.3(3) . . . .
C17 C16 C21 C20 -0.1(5) . . . .
C19 C20 C21 C12 -179.6(3) . . . .
C9 C20 C21 C12 0.1(5) . . . .
C19 C20 C21 C16 0.2(5) . . . .
C9 C20 C21 C16 179.8(3) . . . .
