#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:28:00 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179632 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/96/4509637.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4509637
loop_
_publ_author_name
'Soegiarto, Airon C.'
'Ward, Michael D.'
_publ_section_title
;
 Directed Organization of Dye Aggregates in Hydrogen-Bonded Host
 Frameworks
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3803
_journal_paper_doi               10.1021/cg900578u
_journal_volume                  9
_journal_year                    2009
_chemical_formula_sum            'C14 H20 N8 O6 S2'
_chemical_formula_weight         460.50
_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                98.721(2)
_cell_angle_beta                 96.478(2)
_cell_angle_gamma                93.288(3)
_cell_formula_units_Z            1
_cell_length_a                   6.1980(9)
_cell_length_b                   7.2218(10)
_cell_length_c                   16.044(2)
_cell_measurement_reflns_used    1685
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.43
_cell_measurement_theta_min      2.59
_cell_volume                     703.28(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12135
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0546
_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)+(0.0962P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1522
_reflns_number_gt                1877
_reflns_number_total             2856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg900578usup10.cif
_cod_data_source_block           Ward_Soegiarto_compound_1a
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        703.26(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4509637
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
O1 O 0.3978(3) 0.4240(3) 0.39481(13) 0.0405(5) Uani 1 1 d . . .
O2 O 0.4255(3) 0.1059(3) 0.42114(13) 0.0414(5) Uani 1 1 d . . .
O3 O 0.0741(3) 0.2143(3) 0.37957(12) 0.0342(5) Uani 1 1 d . . .
S1 S 0.30730(10) 0.23056(10) 0.37398(4) 0.0295(2) Uani 1 1 d . A .
C1 C 0.9430(4) 0.7294(4) 0.41325(18) 0.0354(7) Uani 1 1 d . . .
C2 C 0.3382(4) 0.1589(4) 0.26639(18) 0.0379(7) Uani 1 1 d . . .
C5 C 0.3933(5) 0.0577(6) 0.0978(2) 0.0645(11) Uani 1 1 d . . .
C3 C 0.1623(14) 0.1522(12) 0.2047(5) 0.0474(17) Uani 0.586(8) 1 d PU A -1
H3 H 0.0229 0.1803 0.2201 0.057 Uiso 0.586(8) 1 calc PR A -1
C4 C 0.1918(13) 0.1034(13) 0.1191(5) 0.0529(17) Uani 0.586(8) 1 d PU A -1
H4 H 0.0732 0.1018 0.0759 0.063 Uiso 0.586(8) 1 calc PR A -1
C6 C 0.5720(14) 0.1353(12) 0.1569(5) 0.0515(17) Uani 0.586(8) 1 d PU A -1
H6 H 0.7113 0.1543 0.1388 0.062 Uiso 0.586(8) 1 calc PR A -1
C7 C 0.5445(16) 0.1835(12) 0.2409(6) 0.0504(18) Uani 0.586(8) 1 d PU A -1
H7 H 0.6653 0.2335 0.2814 0.060 Uiso 0.586(8) 1 calc PR A -1
C3' C 0.168(2) 0.0681(17) 0.2096(8) 0.0474(17) Uani 0.414(8) 1 d P A -2
H3' H 0.0305 0.0444 0.2287 0.057 Uiso 0.414(8) 1 calc PR A -2
C4' C 0.193(2) 0.0126(18) 0.1273(8) 0.0529(17) Uani 0.414(8) 1 d P A -2
H4' H 0.0767 -0.0563 0.0895 0.063 Uiso 0.414(8) 1 calc PR A -2
C6' C 0.563(2) 0.0433(17) 0.1603(8) 0.0515(17) Uani 0.414(8) 1 d P A -2
H6' H 0.6958 -0.0049 0.1457 0.062 Uiso 0.414(8) 1 calc PR A -2
C7' C 0.534(2) 0.1008(17) 0.2437(9) 0.0504(18) Uani 0.414(8) 1 d P A -2
H7' H 0.6524 0.1005 0.2868 0.060 Uiso 0.414(8) 1 calc PR A -2
N4 N 0.4054(4) 0.0024(6) 0.00948(18) 0.0788(12) Uani 1 1 d . . .
N1 N 0.8485(4) 0.5618(3) 0.41308(16) 0.0416(6) Uani 1 1 d . . .
H1A H 0.9273 0.4643 0.4134 0.050 Uiso 1 1 calc R . .
H1B H 0.7064 0.5471 0.4127 0.050 Uiso 1 1 calc R . .
N2 N 1.1550(4) 0.7492(4) 0.4139(2) 0.0549(8) Uani 1 1 d . . .
H2A H 1.2323 0.6507 0.4142 0.066 Uiso 1 1 calc R . .
H2B H 1.2199 0.8608 0.4140 0.066 Uiso 1 1 calc R . .
N3 N 0.8290(4) 0.8790(3) 0.41289(17) 0.0428(7) Uani 1 1 d . . .
H3A H 0.8956 0.9900 0.4131 0.051 Uiso 1 1 calc R . .
H3B H 0.6868 0.8673 0.4125 0.051 Uiso 1 1 calc R . .
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
O2 S1 O1 112.90(13) .
O2 S1 O3 112.79(11) .
O1 S1 O3 111.94(11) .
O2 S1 C2 106.43(13) .
O1 S1 C2 105.85(13) .
O3 S1 C2 106.29(12) .
N2 C1 N1 119.3(3) .
N2 C1 N3 119.2(3) .
N1 C1 N3 121.5(3) .
C7' C2 C3' 110.7(8) .
C7' C2 C3 119.7(7) .
C3' C2 C3 26.2(5) .
C7' C2 C7 25.3(6) .
C3' C2 C7 120.3(7) .
C3 C2 C7 116.7(6) .
C7' C2 S1 120.4(6) .
C3' C2 S1 121.2(6) .
C3 C2 S1 119.9(4) .
C7 C2 S1 118.4(4) .
C4 C5 C6' 120.8(7) .
C4 C5 C6 115.8(5) .
C6' C5 C6 27.9(5) .
C4 C5 C4' 28.5(5) .
C6' C5 C4' 109.2(8) .
C6 C5 C4' 119.2(7) .
C4 C5 N4 115.7(4) .
C6' C5 N4 123.0(6) .
C6 C5 N4 123.9(4) .
C4' C5 N4 116.7(6) .
C2 C3 C4 119.2(7) .
C2 C3 H3 120.4 .
C4 C3 H3 120.4 .
C5 C4 C3 119.7(7) .
C5 C4 H4 120.1 .
C3 C4 H4 120.1 .
C7 C6 C5 119.6(7) .
C7 C6 H6 120.2 .
C5 C6 H6 120.2 .
C6 C7 C2 119.7(8) .
C6 C7 H7 120.2 .
C2 C7 H7 120.2 .
C4' C3' C2 120.9(11) .
C4' C3' H3' 119.6 .
C2 C3' H3' 119.6 .
C3' C4' C5 119.6(11) .
C3' C4' H4' 120.2 .
C5 C4' H4' 120.2 .
C7' C6' C5 118.2(11) .
C7' C6' H6' 120.9 .
C5 C6' H6' 120.9 .
C6' C7' C2 121.7(12) .
C6' C7' H7' 119.1 .
C2 C7' H7' 119.1 .
N4 N4 C5 114.1(3) 2_655
C1 N1 H1A 120.0 .
C1 N1 H1B 120.0 .
H1A N1 H1B 120.0 .
C1 N2 H2A 120.0 .
C1 N2 H2B 120.0 .
H2A N2 H2B 120.0 .
C1 N3 H3A 120.0 .
C1 N3 H3B 120.0 .
H3A N3 H3B 120.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 S1 1.450(2) .
O2 S1 1.441(2) .
O3 S1 1.4576(19) .
S1 C2 1.761(3) .
C1 N2 1.313(3) .
C1 N1 1.313(4) .
C1 N3 1.324(3) .
C2 C7' 1.376(15) .
C2 C3' 1.378(13) .
C2 C3 1.381(9) .
C2 C7 1.396(10) .
C5 C4 1.377(9) .
C5 C6' 1.389(13) .
C5 C6 1.404(9) .
C5 C4' 1.418(13) .
C5 N4 1.424(4) .
C3 C4 1.400(11) .
C3 H3 0.9500 .
C4 H4 0.9500 .
C6 C7 1.371(12) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C3' C4' 1.349(17) .
C3' H3' 0.9500 .
C4' H4' 0.9500 .
C6' C7' 1.375(19) .
C6' H6' 0.9500 .
C7' H7' 0.9500 .
N4 N4 1.246(5) 2_655
N1 H1A 0.8800 .
N1 H1B 0.8800 .
N2 H2A 0.8800 .
N2 H2B 0.8800 .
N3 H3A 0.8800 .
N3 H3B 0.8800 .
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
N1 H1A O3 0.88 2.09 2.951(3) 164.2 1_655
N1 H1B O1 0.88 2.03 2.879(3) 160.7 .
N2 H2A O1 0.88 1.99 2.857(3) 170.9 1_655
N2 H2B O2 0.88 2.10 2.972(3) 169.8 1_665
N3 H3A O3 0.88 2.08 2.934(3) 163.3 1_665
N3 H3B O2 0.88 2.43 3.072(3) 130.1 1_565
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_4
O2 S1 C2 C7' -38.7(7) .
O1 S1 C2 C7' 81.6(7) .
O3 S1 C2 C7' -159.2(6) .
O2 S1 C2 C3' 107.6(6) .
O1 S1 C2 C3' -132.0(6) .
O3 S1 C2 C3' -12.8(6) .
O2 S1 C2 C3 138.1(5) .
O1 S1 C2 C3 -101.5(5) .
O3 S1 C2 C3 17.7(5) .
O2 S1 C2 C7 -67.7(5) .
O1 S1 C2 C7 52.7(5) .
O3 S1 C2 C7 171.8(4) .
C7' C2 C3 C4 -6.1(11) .
C3' C2 C3 C4 -82.4(19) .
C7 C2 C3 C4 22.5(9) .
S1 C2 C3 C4 177.0(4) .
C6' C5 C4 C3 5.7(12) .
C6 C5 C4 C3 -25.7(10) .
C4' C5 C4 C3 78.4(16) .
N4 C5 C4 C3 177.5(5) .
C2 C3 C4 C5 1.9(9) .
C4 C5 C6 C7 25.5(10) .
C6' C5 C6 C7 -82.1(17) .
C4' C5 C6 C7 -6.5(11) .
N4 C5 C6 C7 -179.7(5) .
C5 C6 C7 C2 -1.4(10) .
C7' C2 C7 C6 81(2) .
C3' C2 C7 C6 6.9(11) .
C3 C2 C7 C6 -22.7(9) .
S1 C2 C7 C6 -177.7(5) .
C7' C2 C3' C4' -30.3(13) .
C3 C2 C3' C4' 85(2) .
C7 C2 C3' C4' -4.3(13) .
S1 C2 C3' C4' -179.6(7) .
C2 C3' C4' C5 -3.7(14) .
C4 C5 C4' C3' -81.9(17) .
C6' C5 C4' C3' 37.8(13) .
C6 C5 C4' C3' 9.1(13) .
N4 C5 C4' C3' -177.2(8) .
C4 C5 C6' C7' -8.8(14) .
C6 C5 C6' C7' 78.8(16) .
C4' C5 C6' C7' -37.6(13) .
N4 C5 C6' C7' 180.0(7) .
C5 C6' C7' C2 4.5(15) .
C3' C2 C7' C6' 30.2(13) .
C3 C2 C7' C6' 2.8(14) .
C7 C2 C7' C6' -87(2) .
S1 C2 C7' C6' 179.7(7) .
C4 C5 N4 N4 166.7(6) 2_655
C6' C5 N4 N4 -21.6(10) 2_655
C6 C5 N4 N4 11.9(9) 2_655
C4' C5 N4 N4 -161.5(7) 2_655
