#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/54/7105461.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_7105461
loop_
_publ_author_name
'Bose, Purnandhu'
'Ghosh, Pradyut'
_publ_section_title
;
 Visible and near-infrared sensing of fluoride by indole conjugated
 urea/thiourea ligands.
;
_journal_issue                   17
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2962
_journal_page_last               2964
_journal_paper_doi               10.1039/b919128c
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C19 H16 N6 S'
_chemical_formula_weight         360.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   15.3835(16)
_cell_length_b                   11.4337(12)
_cell_length_c                   19.997(2)
_cell_measurement_reflns_used    8184
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.43
_cell_volume                     3517.3(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'MERCURY 2.2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       '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  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30864
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0361
_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)+(0.0517P)²+1.2735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                2647
_reflns_number_total             3099
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b919128c.txt
_cod_data_source_block           compound-1a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               7105461
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.54113(11) 0.57815(16) 0.26273(9) 0.0364(4) Uani 1 1 d . . .
H1 H 0.5519 0.6237 0.3004 0.044 Uiso 1 1 calc R . .
N2 N 0.58896(9) 0.58062(13) 0.20586(7) 0.0397(4) Uani 1 1 d . . .
H2 H 0.6335 0.6244 0.1989 0.048 Uiso 1 1 calc R . .
C3 C 0.55465(11) 0.50138(15) 0.16087(9) 0.0345(4) Uani 1 1 d . . .
C4 C 0.57993(12) 0.47695(17) 0.09549(10) 0.0444(5) Uani 1 1 d . . .
H4 H 0.6275 0.5139 0.0760 0.053 Uiso 1 1 calc R . .
C5 C 0.53174(14) 0.39628(19) 0.06108(11) 0.0529(5) Uani 1 1 d . . .
H5 H 0.5469 0.3783 0.0173 0.064 Uiso 1 1 calc R . .
C6 C 0.46003(14) 0.33998(19) 0.09018(10) 0.0508(5) Uani 1 1 d . . .
H6 H 0.4291 0.2851 0.0655 0.061 Uiso 1 1 calc R . .
C7 C 0.43474(12) 0.36468(16) 0.15486(9) 0.0383(4) Uani 1 1 d . . .
H7 H 0.3873 0.3269 0.1739 0.046 Uiso 1 1 calc R . .
C8 C 0.48183(10) 0.44754(14) 0.19118(8) 0.0314(4) Uani 1 1 d . . .
C9 C 0.47441(10) 0.49876(15) 0.25698(8) 0.0305(4) Uani 1 1 d . . .
C10 C 0.41866(10) 0.47135(14) 0.31242(8) 0.0300(4) Uani 1 1 d . . .
H10 H 0.4271 0.5123 0.3521 0.036 Uiso 1 1 calc R . .
N11 N 0.35763(8) 0.39378(12) 0.31108(6) 0.0297(3) Uani 1 1 d . . .
N12 N 0.31889(9) 0.38000(12) 0.37341(6) 0.0319(3) Uani 1 1 d . . .
H12 H 0.3319 0.4291 0.4044 0.038 Uiso 1 1 calc R . .
C13 C 0.26258(10) 0.29460(14) 0.38764(8) 0.0296(4) Uani 1 1 d . . .
S14 S 0.21887(3) 0.20023(4) 0.33242(2) 0.04079(17) Uani 1 1 d . . .
N15 N 0.24096(9) 0.28846(12) 0.45343(7) 0.0332(3) Uani 1 1 d . . .
H15 H 0.2068 0.2344 0.4677 0.040 Uiso 1 1 calc R . .
N16 N 0.27478(8) 0.37071(12) 0.49704(6) 0.0303(3) Uani 1 1 d . . .
C17 C 0.24399(10) 0.37159(15) 0.55677(8) 0.0298(4) Uani 1 1 d . . .
H17 H 0.2021 0.3171 0.5692 0.036 Uiso 1 1 calc R . .
C18 C 0.27404(10) 0.45663(15) 0.60468(7) 0.0287(4) Uani 1 1 d . . .
C19 C 0.23848(11) 0.47556(16) 0.66694(8) 0.0352(4) Uani 1 1 d . . .
H19 H 0.1938 0.4316 0.6856 0.042 Uiso 1 1 calc R . .
N20 N 0.27809(9) 0.56750(14) 0.69711(7) 0.0373(4) Uani 1 1 d . . .
H20 H 0.2654 0.5943 0.7361 0.045 Uiso 1 1 calc R . .
C21 C 0.34184(11) 0.61145(15) 0.65561(8) 0.0322(4) Uani 1 1 d . . .
C22 C 0.40060(12) 0.70196(16) 0.66603(9) 0.0412(5) Uani 1 1 d . . .
H22 H 0.4003 0.7454 0.7054 0.049 Uiso 1 1 calc R . .
C23 C 0.45953(12) 0.72473(16) 0.61540(10) 0.0444(5) Uani 1 1 d . . .
H23 H 0.4994 0.7852 0.6206 0.053 Uiso 1 1 calc R . .
C24 C 0.46042(12) 0.65871(16) 0.55662(9) 0.0399(4) Uani 1 1 d . . .
H24 H 0.5010 0.6760 0.5236 0.048 Uiso 1 1 calc R . .
C25 C 0.40244(10) 0.56849(15) 0.54641(8) 0.0318(4) Uani 1 1 d . . .
H25 H 0.4038 0.5251 0.5071 0.038 Uiso 1 1 calc R . .
C26 C 0.34133(10) 0.54343(14) 0.59647(7) 0.0272(3) 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'
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
_geom_angle_publ_flag
N2 C1 C9 110.42(16) . . ?
N2 C1 H1 124.8 . . ?
C9 C1 H1 124.8 . . ?
C1 N2 C3 109.00(14) . . ?
C1 N2 H2 125.5 . . ?
C3 N2 H2 125.5 . . ?
N2 C3 C4 129.51(17) . . ?
N2 C3 C8 108.00(15) . . ?
C4 C3 C8 122.42(17) . . ?
C5 C4 C3 117.12(18) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C4 C5 C6 121.76(19) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 118.69(17) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C7 C8 C3 118.90(16) . . ?
C7 C8 C9 135.05(16) . . ?
C3 C8 C9 106.04(15) . . ?
C1 C9 C10 121.68(15) . . ?
C1 C9 C8 106.55(14) . . ?
C10 C9 C8 131.43(15) . . ?
N11 C10 C9 124.59(15) . . ?
N11 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
C10 N11 N12 111.76(13) . . ?
C13 N12 N11 123.48(13) . . ?
C13 N12 H12 118.3 . . ?
N11 N12 H12 118.3 . . ?
N12 C13 N15 113.75(14) . . ?
N12 C13 S14 125.99(12) . . ?
N15 C13 S14 120.26(13) . . ?
C13 N15 N16 118.88(13) . . ?
C13 N15 H15 120.6 . . ?
N16 N15 H15 120.6 . . ?
C17 N16 N15 116.90(13) . . ?
N16 C17 C18 120.33(15) . . ?
N16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 125.43(15) . . ?
C19 C18 C26 106.24(14) . . ?
C17 C18 C26 128.20(14) . . ?
N20 C19 C18 110.21(15) . . ?
N20 C19 H19 124.9 . . ?
C18 C19 H19 124.9 . . ?
C19 N20 C21 109.51(13) . . ?
C19 N20 H20 125.2 . . ?
C21 N20 H20 125.2 . . ?
N20 C21 C22 130.05(16) . . ?
N20 C21 C26 107.37(15) . . ?
C22 C21 C26 122.54(16) . . ?
C23 C22 C21 117.17(16) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C22 C23 C24 121.35(17) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 121.50(17) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C24 C25 C26 118.73(16) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C25 C26 C21 118.70(15) . . ?
C25 C26 C18 134.61(14) . . ?
C21 C26 C18 106.66(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.355(2) . ?
C1 C9 1.375(2) . ?
C1 H1 0.9300 . ?
N2 C3 1.382(2) . ?
N2 H2 0.8600 . ?
C3 C4 1.392(2) . ?
C3 C8 1.415(2) . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.445(2) . ?
C9 C10 1.436(2) . ?
C10 N11 1.292(2) . ?
C10 H10 0.9300 . ?
N11 N12 1.3905(18) . ?
N12 C13 1.336(2) . ?
N12 H12 0.8600 . ?
C13 N15 1.359(2) . ?
C13 S14 1.6840(16) . ?
N15 N16 1.3841(18) . ?
N15 H15 0.8600 . ?
N16 C17 1.285(2) . ?
C17 C18 1.441(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(2) . ?
C18 C26 1.443(2) . ?
C19 N20 1.357(2) . ?
C19 H19 0.9300 . ?
N20 C21 1.380(2) . ?
N20 H20 0.8600 . ?
C21 C22 1.390(3) . ?
C21 C26 1.416(2) . ?
C22 C23 1.384(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.397(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.403(2) . ?
C25 H25 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 S14 0.86 2.51 3.3461(15) 164.2 3_655
N20 H20 N11 0.86 2.42 3.1223(19) 139.4 2_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653199
