#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/47/4504721.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_4504721
loop_
_publ_author_name
'Burke, Nichola J.'
'Burrows, Andrew D.'
'Mahon, Mary F.'
'Warren, John E.'
_publ_section_title
;
 Incorporation of Dyes into Hydrogen-Bond Networks:  The Structures
 and Properties of Guanidinium Sulfonate Derivatives Containing Ethyl
 Orange and 4-Aminoazobenzene-4‘-sulfonate
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              546
_journal_paper_doi               10.1021/cg050499e
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C16 H20.5 N3 O3.75 S'
_chemical_formula_weight         346.91
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.601(2)
_cell_angle_beta                 109.008(2)
_cell_angle_gamma                97.340(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3730(2)
_cell_length_b                   9.0090(3)
_cell_length_c                   11.6500(3)
_cell_measurement_reflns_used    17621
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     791.81(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'Denzo & Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle, 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick,1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       KappaCCD
_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  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0686
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11474
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             367
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0556
_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)+(0.0513P)²+0.7140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1381
_reflns_number_gt                2547
_reflns_number_total             3536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050499esi20050926_121833.cif
_cod_data_source_block           c:\compound_5\k04njb1
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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      P-1
_cod_original_formula_sum        'C16 H20.50 N3 O3.75 S'
_cod_database_code               4504721
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S -0.42512(8) 0.00789(8) 0.27744(6) 0.02149(19) Uani 1 1 d . . .
O1 O -0.4583(2) -0.1548(2) 0.20952(17) 0.0267(4) Uani 1 1 d . . .
O2 O -0.4923(2) 0.1075(2) 0.19937(18) 0.0312(5) Uani 1 1 d . . .
O3 O -0.4748(2) 0.0297(2) 0.38836(17) 0.0297(5) Uani 1 1 d . . .
O4 O -0.6791(4) 0.2005(4) -0.0164(3) 0.0383(7) Uani 0.75 1 d PD A 1
N1 N 0.3387(3) 0.2352(3) 0.5111(2) 0.0238(5) Uani 1 1 d . . .
H1A H 0.4063 0.1686 0.5071 0.029 Uiso 1 1 calc R . .
N2 N 0.4045(3) 0.3802(3) 0.5737(2) 0.0226(5) Uani 1 1 d . . .
N3 N 1.0849(3) 0.6310(3) 0.8800(2) 0.0308(5) Uani 1 1 d . C .
C1 C -0.1971(3) 0.0758(3) 0.3394(2) 0.0205(5) Uani 1 1 d . . .
C2 C -0.0868(3) -0.0242(3) 0.3260(2) 0.0243(5) Uani 1 1 d . . .
H2 H -0.1333 -0.1304 0.2794 0.029 Uiso 1 1 calc R . .
C3 C 0.0909(3) 0.0310(3) 0.3806(2) 0.0245(6) Uani 1 1 d . . .
H3 H 0.1663 -0.0371 0.3709 0.029 Uiso 1 1 calc R . .
C4 C 0.1582(3) 0.1855(3) 0.4495(2) 0.0216(5) Uani 1 1 d . . .
C5 C 0.0489(3) 0.2879(3) 0.4609(2) 0.0243(6) Uani 1 1 d . . .
H5 H 0.0955 0.3945 0.5062 0.029 Uiso 1 1 calc R . .
C6 C -0.1287(3) 0.2317(3) 0.4051(2) 0.0242(6) Uani 1 1 d . . .
H6 H -0.2042 0.3005 0.4120 0.029 Uiso 1 1 calc R . .
C7 C 0.5742(3) 0.4292(3) 0.6410(2) 0.0213(5) Uani 1 1 d . . .
C8 C 0.7021(3) 0.3372(3) 0.6586(3) 0.0276(6) Uani 1 1 d . . .
H8 H 0.6706 0.2291 0.6163 0.033 Uiso 1 1 calc R . .
C9 C 0.8686(3) 0.4034(3) 0.7355(3) 0.0300(6) Uani 1 1 d . . .
H9 H 0.9518 0.3401 0.7468 0.036 Uiso 1 1 calc R . .
C10 C 0.9224(3) 0.5672(3) 0.8004(2) 0.0257(6) Uani 1 1 d . . .
C11 C 0.7944(3) 0.6589(3) 0.7784(2) 0.0236(5) Uani 1 1 d . . .
H11 H 0.8262 0.7681 0.8165 0.028 Uiso 1 1 calc R . .
C12 C 0.6278(3) 0.5913(3) 0.7037(2) 0.0234(5) Uani 1 1 d . . .
H12 H 0.5442 0.6542 0.6928 0.028 Uiso 1 1 calc R . .
C13 C 1.2144(4) 0.5351(4) 0.9226(3) 0.0368(7) Uani 1 1 d . . .
H13A H 1.1546 0.4344 0.9252 0.044 Uiso 1 1 calc R B 1
H13B H 1.2978 0.5904 1.0088 0.044 Uiso 1 1 calc R B 1
C14 C 1.3085(5) 0.5068(4) 0.8330(3) 0.0462(8) Uani 1 1 d . C 1
H14A H 1.2257 0.4495 0.7484 0.069 Uiso 1 1 calc R . .
H14B H 1.3946 0.4457 0.8618 0.069 Uiso 1 1 calc R . .
H14C H 1.3666 0.6068 0.8302 0.069 Uiso 1 1 calc R . .
C15 C 1.1471(3) 0.8002(3) 0.9354(3) 0.0281(6) Uani 1 1 d . . .
H15A H 1.0863 0.8543 0.8744 0.034 Uiso 1 1 calc R C .
H15B H 1.2723 0.8283 0.9519 0.034 Uiso 1 1 calc R . .
C16 C 1.1167(4) 0.8539(4) 1.0572(3) 0.0334(7) Uani 1 1 d . C .
H16A H 0.9923 0.8302 1.0404 0.050 Uiso 1 1 calc R . .
H16B H 1.1621 0.9665 1.0928 0.050 Uiso 1 1 calc R . .
H16C H 1.1760 0.7998 1.1174 0.050 Uiso 1 1 calc R . .
H4B H -0.628(7) 0.182(7) -0.073(4) 0.08(2) Uiso 0.75 1 d PD D 1
H4A H -0.631(6) 0.156(5) 0.044(3) 0.053(14) Uiso 0.75 1 d PD E 1
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 114.65(12)
O1 S1 O3 112.43(12)
O2 S1 O3 112.28(12)
O1 S1 C1 106.40(11)
O2 S1 C1 105.26(12)
O3 S1 C1 104.86(11)
N2 N1 C4 119.3(2)
N1 N2 C7 120.9(2)
C10 N3 C15 122.2(2)
C10 N3 C13 122.5(2)
C15 N3 C13 115.3(2)
C6 C1 C2 119.8(2)
C6 C1 S1 118.70(18)
C2 C1 S1 121.5(2)
C3 C2 C1 120.1(2)
C4 C3 C2 119.8(2)
C3 C4 C5 120.6(2)
C3 C4 N1 118.4(2)
C5 C4 N1 120.9(2)
C6 C5 C4 119.0(2)
C5 C6 C1 120.6(2)
N2 C7 C12 114.6(2)
N2 C7 C8 127.4(2)
C12 C7 C8 117.9(2)
C9 C8 C7 120.4(2)
C8 C9 C10 121.7(2)
N3 C10 C11 121.0(2)
N3 C10 C9 121.6(2)
C11 C10 C9 117.4(2)
C12 C11 C10 120.5(2)
C11 C12 C7 122.1(2)
N3 C13 C14 109.5(3)
N3 C15 C16 111.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4482(19)
S1 O2 1.4493(19)
S1 O3 1.4634(18)
S1 C1 1.775(3)
N1 N2 1.296(3)
N1 C4 1.407(3)
N2 C7 1.338(3)
N3 C10 1.337(3)
N3 C15 1.470(4)
N3 C13 1.498(4)
C1 C6 1.388(4)
C1 C2 1.390(3)
C2 C3 1.387(4)
C3 C4 1.384(4)
C4 C5 1.395(3)
C5 C6 1.387(4)
C7 C12 1.422(4)
C7 C8 1.426(4)
C8 C9 1.358(4)
C9 C10 1.440(4)
C10 C11 1.427(4)
C11 C12 1.354(4)
C13 C14 1.499(5)
C15 C16 1.510(4)
