#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:13:32 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178462 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/83/4028398.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_4028398
loop_
_publ_author_name
'Leticia A. Montoya'
'Taylor F. Pearce'
'Ryan J. Hansen'
'Lev N. Zakharov'
'Michael D. Pluth'
_publ_section_title
;
 Development of Selective Colorimetric Probes for Hydrogen Sulfide Based
 on Nucleophilic Aromatic Substitution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6550
_journal_page_last               6557
_journal_paper_doi               10.1021/jo4008095
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C12 H4 N6 O6 S'
_chemical_formula_weight         360.27
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 107.601(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1415(13)
_cell_length_b                   11.4080(11)
_cell_length_c                   9.3240(9)
_cell_measurement_reflns_used    5625
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.41
_cell_volume                     1332.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex 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  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14609
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  0.9710
_exptl_absorpt_correction_T_min  0.8934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_description       Prizm
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0319
_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)+(0.0488P)²+0.4180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                2634
_reflns_number_total             2897
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4008095_si_002.cif
_cod_data_source_block           mp1a
_cod_database_code               4028398
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 0.85853(3) 0.96239(3) 0.99293(4) 0.02533(11) Uani 1 1 d
O1 O 1.00955(9) 0.64875(10) 1.24572(12) 0.0318(3) Uani 1 1 d
O2 O 0.85369(11) 0.37231(10) 0.97405(14) 0.0415(3) Uani 1 1 d
O3 O 0.75198(10) 0.40716(10) 0.74670(15) 0.0411(3) Uani 1 1 d
O4 O 0.49585(8) 0.93005(10) 0.85753(12) 0.0289(2) Uani 1 1 d
O5 O 0.40131(10) 1.14857(11) 0.49244(13) 0.0400(3) Uani 1 1 d
O6 O 0.51518(11) 1.24700(11) 0.41386(13) 0.0423(3) Uani 1 1 d
N1 N 0.97545(9) 0.75643(11) 1.18475(13) 0.0270(3) Uani 1 1 d
N2 N 0.95954(10) 0.55660(11) 1.15437(15) 0.0313(3) Uani 1 1 d
N3 N 0.80742(10) 0.43930(11) 0.87131(16) 0.0305(3) Uani 1 1 d
N4 N 0.60456(9) 0.92605(11) 0.92180(14) 0.0256(3) Uani 1 1 d
N5 N 0.46480(10) 1.00503(11) 0.73655(14) 0.0264(3) Uani 1 1 d
N6 N 0.49244(11) 1.18010(11) 0.50218(14) 0.0303(3) Uani 1 1 d
C1 C 0.84020(10) 0.81340(12) 0.94708(15) 0.0213(3) Uani 1 1 d
C2 C 0.90349(10) 0.73249(12) 1.05538(15) 0.0221(3) Uani 1 1 d
C3 C 0.89400(11) 0.60804(12) 1.03574(16) 0.0240(3) Uani 1 1 d
C4 C 0.82054(11) 0.56435(13) 0.90015(17) 0.0250(3) Uani 1 1 d
C5 C 0.76261(11) 0.64173(13) 0.79749(17) 0.0247(3) Uani 1 1 d
C6 C 0.77206(11) 0.76517(13) 0.82021(16) 0.0234(3) Uani 1 1 d
C7 C 0.75090(11) 1.02623(12) 0.85307(16) 0.0224(3) Uani 1 1 d
C8 C 0.64211(11) 0.99884(12) 0.84097(15) 0.0210(3) Uani 1 1 d
C9 C 0.55504(11) 1.04863(11) 0.72608(15) 0.0215(3) Uani 1 1 d
C10 C 0.57866(12) 1.13158(12) 0.62543(15) 0.0241(3) Uani 1 1 d
C11 C 0.68145(13) 1.16037(13) 0.64273(17) 0.0278(3) Uani 1 1 d
C12 C 0.76802(12) 1.10731(13) 0.75604(17) 0.0271(3) Uani 1 1 d
H5 H 0.7135(14) 0.6133(16) 0.709(2) 0.031(4) Uiso 1 1 d
H6 H 0.7286(13) 0.8108(16) 0.7419(19) 0.028(4) Uiso 1 1 d
H11 H 0.6981(13) 1.2136(16) 0.5738(19) 0.031(4) Uiso 1 1 d
H12 H 0.8385(14) 1.1274(15) 0.7580(19) 0.027(4) 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'
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
C1 S1 C7 101.52(6)
N1 O1 N2 112.94(10)
N5 O4 N4 112.96(10)
C2 N1 O1 104.37(12)
C3 N2 O1 104.25(12)
O3 N3 O2 124.28(14)
O3 N3 C4 118.20(13)
O2 N3 C4 117.52(13)
C8 N4 O4 104.50(11)
C9 N5 O4 104.20(11)
O6 N6 O5 124.34(14)
O6 N6 C10 118.52(14)
O5 N6 C10 117.12(12)
C6 C1 C2 116.08(13)
C6 C1 S1 127.48(11)
C2 C1 S1 116.44(10)
N1 C2 C3 109.47(12)
N1 C2 C1 127.92(13)
C3 C2 C1 122.59(13)
N2 C3 C4 133.10(14)
N2 C3 C2 108.96(13)
C4 C3 C2 117.94(13)
C5 C4 C3 118.89(13)
C5 C4 N3 119.96(14)
C3 C4 N3 121.15(13)
C4 C5 C6 122.30(14)
C4 C5 H5 119.1(11)
C6 C5 H5 118.6(11)
C1 C6 C5 122.17(13)
C1 C6 H6 122.5(11)
C5 C6 H6 115.4(11)
C12 C7 C8 117.23(13)
C12 C7 S1 121.04(11)
C8 C7 S1 121.68(11)
N4 C8 C9 109.09(12)
N4 C8 C7 129.12(13)
C9 C8 C7 121.74(12)
N5 C9 C8 109.25(12)
N5 C9 C10 132.62(13)
C8 C9 C10 118.13(13)
C11 C10 C9 119.30(13)
C11 C10 N6 120.84(13)
C9 C10 N6 119.81(13)
C10 C11 C12 121.85(13)
C10 C11 H11 119.8(10)
C12 C11 H11 118.2(11)
C7 C12 C11 121.62(14)
C7 C12 H12 120.6(10)
C11 C12 H12 117.7(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7513(14)
S1 C7 1.7652(14)
O1 N1 1.3707(16)
O1 N2 1.3871(17)
O2 N3 1.2326(18)
O3 N3 1.2261(18)
O4 N5 1.3756(16)
O4 N4 1.3728(15)
O5 N6 1.2272(18)
O6 N6 1.2243(17)
N1 C2 1.3169(18)
N2 C3 1.3166(19)
N3 C4 1.4522(19)
N4 C8 1.3139(18)
N5 C9 1.3166(19)
N6 C10 1.4572(19)
C1 C6 1.3651(19)
C1 C2 1.4337(19)
C2 C3 1.432(2)
C3 C4 1.429(2)
C4 C5 1.354(2)
C5 C6 1.424(2)
C5 H5 0.937(18)
C6 H6 0.937(18)
C7 C12 1.359(2)
C7 C8 1.4342(19)
C8 C9 1.4276(19)
C9 C10 1.431(2)
C10 C11 1.352(2)
C11 C12 1.432(2)
C11 H11 0.957(18)
C12 H12 0.949(18)
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
N2 O1 N1 C2 0.36(15)
N1 O1 N2 C3 0.07(15)
N5 O4 N4 C8 0.01(15)
N4 O4 N5 C9 -0.38(15)
C7 S1 C1 C6 10.51(14)
C7 S1 C1 C2 -169.12(10)
O1 N1 C2 C3 -0.62(14)
O1 N1 C2 C1 178.28(13)
C6 C1 C2 N1 179.08(13)
S1 C1 C2 N1 -1.25(19)
C6 C1 C2 C3 -2.15(19)
S1 C1 C2 C3 177.52(10)
O1 N2 C3 C4 179.30(14)
O1 N2 C3 C2 -0.45(15)
N1 C2 C3 N2 0.71(16)
C1 C2 C3 N2 -178.26(12)
N1 C2 C3 C4 -179.08(12)
C1 C2 C3 C4 1.95(19)
N2 C3 C4 C5 179.57(15)
C2 C3 C4 C5 -0.70(19)
N2 C3 C4 N3 -0.5(2)
C2 C3 C4 N3 179.25(12)
O3 N3 C4 C5 7.6(2)
O2 N3 C4 C5 -172.89(13)
O3 N3 C4 C3 -172.33(13)
O2 N3 C4 C3 7.2(2)
C3 C4 C5 C6 -0.2(2)
N3 C4 C5 C6 179.81(13)
C2 C1 C6 C5 1.2(2)
S1 C1 C6 C5 -178.47(11)
C4 C5 C6 C1 0.0(2)
C1 S1 C7 C12 -121.06(12)
C1 S1 C7 C8 61.66(12)
O4 N4 C8 C9 0.34(14)
O4 N4 C8 C7 -177.27(13)
C12 C7 C8 N4 -178.78(14)
S1 C7 C8 N4 -1.4(2)
C12 C7 C8 C9 3.88(19)
S1 C7 C8 C9 -178.74(10)
O4 N5 C9 C8 0.57(14)
O4 N5 C9 C10 -179.61(14)
N4 C8 C9 N5 -0.60(16)
C7 C8 C9 N5 177.21(12)
N4 C8 C9 C10 179.55(12)
C7 C8 C9 C10 -2.64(19)
N5 C9 C10 C11 179.80(14)
C8 C9 C10 C11 -0.40(19)
N5 C9 C10 N6 -2.8(2)
C8 C9 C10 N6 177.03(11)
O6 N6 C10 C11 0.5(2)
O5 N6 C10 C11 178.96(13)
O6 N6 C10 C9 -176.90(12)
O5 N6 C10 C9 1.57(19)
C9 C10 C11 C12 2.1(2)
N6 C10 C11 C12 -175.29(13)
C8 C7 C12 C11 -2.2(2)
S1 C7 C12 C11 -179.57(11)
C10 C11 C12 C7 -0.8(2)
