#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:45:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180354 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/23/7202395.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_7202395
loop_
_publ_author_name
'Hamblin, Jacqueline'
'Argent, Stephen P.'
'Blake, Alexander J.'
'Wilson, Claire'
'Champness, Neil R.'
_publ_section_title
;
 Hydrogen-bonding tectons for the construction of bimolecular framework
 materials
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1782
_journal_paper_doi               10.1039/b811462e
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C22 H10 N6 O8, 4(C2 H6 O S), C3 H6 N6'
_chemical_formula_sum            'C33 H40 N12 O12 S4'
_chemical_formula_weight         925.01
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 110.17(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.41(2)
_cell_length_b                   8.270(7)
_cell_length_c                   23.68(2)
_cell_measurement_reflns_used    3355
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.65
_cell_volume                     4119(6)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    ' ?'
_computing_publication_material
'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_sigmaI/netI    0.066
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12158
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.13
_diffrn_reflns_theta_min         2.69
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.62
_refine_diff_density_rms         0.08
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0606
_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)+(0.082P)²+2.239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.152
_refine_ls_wR_factor_ref         0.164
_reflns_number_gt                3535
_reflns_number_total             4730
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b811462e.txt
_cod_data_source_block           4
_cod_original_cell_volume        4120(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7202395
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.07013(11) 0.4484(3) -0.02121(10) 0.0201(5) Uani 1 1 d . . .
C2 C 0.04758(12) 0.4896(4) -0.08110(11) 0.0277(6) Uani 1 1 d . . .
H2 H 0.0740 0.4755 -0.1047 0.033 Uiso 1 1 calc R . .
C7 C 0.01397(12) 0.4476(3) 0.10789(11) 0.0259(6) Uani 1 1 d . . .
H7 H 0.0286 0.4182 0.1492 0.031 Uiso 1 1 calc R . .
C8 C 0.05298(12) 0.4287(3) 0.07499(10) 0.0204(5) Uani 1 1 d . . .
C9 C 0.03095(11) 0.4684(3) 0.01350(10) 0.0177(5) Uani 1 1 d . . .
C11 C 0.13539(12) 0.3855(3) 0.00614(10) 0.0242(6) Uani 1 1 d . . .
O12 O 0.17098(10) 0.3606(3) -0.02110(8) 0.0411(6) Uani 1 1 d . . .
N13 N 0.15547(10) 0.3525(3) 0.06751(8) 0.0192(4) Uani 1 1 d . . .
C14 C 0.11836(12) 0.3663(3) 0.10424(10) 0.0220(5) Uani 1 1 d . . .
O15 O 0.14022(9) 0.3260(3) 0.15649(8) 0.0328(5) Uani 1 1 d . . .
N21 N 0.22287(10) 0.1292(3) 0.09445(9) 0.0239(5) Uani 1 1 d . . .
H21 H 0.1882 0.0724 0.0769 0.029 Uiso 1 1 calc R . .
C22 C 0.27943(12) 0.0506(3) 0.12018(11) 0.0225(5) Uani 1 1 d . . .
O22 O 0.28431(9) -0.0958(2) 0.11792(9) 0.0337(5) Uani 1 1 d . . .
N23 N 0.32991(10) 0.1473(2) 0.14993(8) 0.0194(4) Uani 1 1 d . . .
H23 H 0.3656 0.0987 0.1711 0.023 Uiso 1 1 calc R . .
C24 C 0.33013(12) 0.3125(3) 0.14985(10) 0.0206(5) Uani 1 1 d . . .
O24 O 0.38063(9) 0.3854(2) 0.17535(8) 0.0291(5) Uani 1 1 d . . .
C25 C 0.26902(12) 0.3876(3) 0.12035(10) 0.0221(5) Uani 1 1 d . . .
H25 H 0.2647 0.5020 0.1188 0.026 Uiso 1 1 calc R . .
C26 C 0.21901(12) 0.2925(3) 0.09544(10) 0.0211(5) Uani 1 1 d . . .
N31 N 0.44531(9) 0.9798(2) 0.21810(8) 0.0190(4) Uani 1 1 d . . .
C32 C 0.5000 1.0549(4) 0.2500 0.0172(7) Uani 1 2 d S . .
N33 N 0.5000 1.2164(4) 0.2500 0.0245(7) Uani 1 2 d S . .
H33A H 0.4652 1.2696 0.2297 0.029 Uiso 0.50 1 calc PR . .
H33B H 0.5348 1.2696 0.2703 0.029 Uiso 0.50 1 calc PR . .
C34 C 0.44859(12) 0.8170(3) 0.21968(10) 0.0205(5) Uani 1 1 d . . .
N35 N 0.5000 0.7295(4) 0.2500 0.0227(6) Uani 1 2 d S . .
N36 N 0.39642(10) 0.7363(3) 0.18724(10) 0.0277(5) Uani 1 1 d . . .
H36A H 0.3968 0.6299 0.1864 0.033 Uiso 1 1 calc R . .
H36B H 0.3617 0.7894 0.1667 0.033 Uiso 1 1 calc R . .
S1A S 0.41368(4) 0.61951(9) 0.00722(3) 0.0329(2) Uani 1 1 d . . .
O2A O 0.39855(10) 0.4875(3) -0.03945(9) 0.0370(5) Uani 1 1 d . . .
C3A C 0.34128(16) 0.6581(4) 0.01990(14) 0.0441(8) Uani 1 1 d . . .
H3A1 H 0.3115 0.7131 -0.0152 0.066 Uiso 1 1 calc R . .
H3A2 H 0.3497 0.7269 0.0555 0.066 Uiso 1 1 calc R . .
H3A3 H 0.3227 0.5556 0.0264 0.066 Uiso 1 1 calc R . .
C4A C 0.45652(17) 0.5223(4) 0.07626(13) 0.0457(8) Uani 1 1 d . . .
H4A1 H 0.4989 0.4925 0.0764 0.069 Uiso 1 1 calc R . .
H4A2 H 0.4337 0.4248 0.0806 0.069 Uiso 1 1 calc R . .
H4A3 H 0.4606 0.5961 0.1098 0.069 Uiso 1 1 calc R . .
S1B S 0.17820(4) 0.79815(10) 0.16046(3) 0.0333(2) Uani 0.90 1 d PD A 1
O2B O 0.16332(11) 0.6830(3) 0.10957(9) 0.0390(5) Uani 0.90 1 d PD A 1
C3B C 0.23201(16) 0.6964(4) 0.22444(13) 0.0488(9) Uani 0.90 1 d PD A 1
H3B1 H 0.2738 0.6883 0.2201 0.073 Uiso 0.90 1 calc PR A 1
H3B2 H 0.2159 0.5877 0.2273 0.073 Uiso 0.90 1 calc PR A 1
H3B3 H 0.2358 0.7575 0.2610 0.073 Uiso 0.90 1 calc PR A 1
C4B C 0.10987(18) 0.7905(6) 0.18364(17) 0.0595(12) Uani 0.90 1 d PD A 1
H4B1 H 0.0737 0.8425 0.1531 0.089 Uiso 0.90 1 calc PR A 1
H4B2 H 0.1193 0.8472 0.2221 0.089 Uiso 0.90 1 calc PR A 1
H4B3 H 0.0993 0.6774 0.1884 0.089 Uiso 0.90 1 calc PR A 1
S1B' S 0.1495(4) 0.7229(14) 0.1786(3) 0.069(3) Uiso 0.10 1 d PD B 2
O2B' O 0.1390(13) 0.901(2) 0.1794(9) 0.102(12) Uiso 0.10 1 d PD B 2
C3B' C 0.23201(16) 0.6964(4) 0.22444(13) 0.0488(9) Uani 0.10 1 d PD B 2
H3B4 H 0.2371 0.7124 0.2669 0.073 Uiso 0.10 1 calc PR B 2
H3B5 H 0.2580 0.7756 0.2125 0.073 Uiso 0.10 1 calc PR B 2
H3B6 H 0.2457 0.5869 0.2188 0.073 Uiso 0.10 1 calc PR B 2
C4B' C 0.16332(11) 0.6830(3) 0.10957(9) 0.0390(5) Uani 0.10 1 d PD B 2
H4B4 H 0.1230 0.6899 0.0758 0.058 Uiso 0.10 1 calc PR B 2
H4B5 H 0.1813 0.5744 0.1111 0.058 Uiso 0.10 1 calc PR B 2
H4B6 H 0.1932 0.7630 0.1042 0.058 Uiso 0.10 1 calc PR B 2
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
_geom_angle_publ_flag
C2 C1 C9 119.6(2) . . ?
C2 C1 C11 119.8(2) . . ?
C9 C1 C11 120.7(2) . . ?
C1 C2 C7 120.8(2) . 5_565 ?
C8 C7 C2 120.5(2) . 5_565 ?
C7 C8 C9 119.9(2) . . ?
C7 C8 C14 119.8(2) . . ?
C9 C8 C14 120.2(2) . . ?
C1 C9 C8 120.8(2) . . ?
C1 C9 C9 119.6(3) . 5_565 ?
C8 C9 C9 119.6(3) . 5_565 ?
O12 C11 N13 119.4(2) . . ?
O12 C11 C1 124.4(2) . . ?
N13 C11 C1 116.3(2) . . ?
C11 N13 C14 125.8(2) . . ?
C11 N13 C26 117.4(2) . . ?
C14 N13 C26 116.69(19) . . ?
O15 C14 N13 119.7(2) . . ?
O15 C14 C8 124.1(2) . . ?
N13 C14 C8 116.2(2) . . ?
C26 N21 C22 121.4(2) . . ?
O22 C22 N23 122.2(2) . . ?
O22 C22 N21 122.4(2) . . ?
N23 C22 N21 115.3(2) . . ?
C22 N23 C24 126.0(2) . . ?
O24 C24 N23 119.3(2) . . ?
O24 C24 C25 125.5(2) . . ?
N23 C24 C25 115.3(2) . . ?
C26 C25 C24 118.3(2) . . ?
C25 C26 N21 123.3(2) . . ?
C25 C26 N13 123.4(2) . . ?
N21 C26 N13 113.3(2) . . ?
C34 N31 C32 114.4(2) . . ?
N33 C32 N31 117.40(16) . . ?
N33 C32 N31 117.40(16) . 2_655 ?
N31 C32 N31 125.2(3) . 2_655 ?
N36 C34 N35 117.3(2) . . ?
N36 C34 N31 117.1(2) . . ?
N35 C34 N31 125.6(2) . . ?
C34 N35 C34 114.6(3) 2_655 . ?
O2A S1A C4A 105.10(16) . . ?
O2A S1A C3A 105.44(14) . . ?
C4A S1A C3A 99.25(17) . . ?
O2B S1B C3B 106.49(16) . . ?
O2B S1B C4B 104.43(18) . . ?
C3B S1B C4B 97.0(2) . . ?
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 C2 1.374(3) . ?
C1 C9 1.404(3) . ?
C1 C11 1.475(4) . ?
C2 C7 1.404(4) 5_565 ?
C7 C8 1.366(4) . ?
C7 C2 1.404(4) 5_565 ?
C8 C9 1.406(3) . ?
C8 C14 1.481(4) . ?
C9 C9 1.412(5) 5_565 ?
C11 O12 1.204(3) . ?
C11 N13 1.392(3) . ?
N13 C14 1.400(3) . ?
N13 C26 1.436(3) . ?
C14 O15 1.210(3) . ?
N21 C26 1.354(3) . ?
N21 C22 1.367(3) . ?
C22 O22 1.218(3) . ?
C22 N23 1.366(3) . ?
N23 C24 1.367(3) . ?
C24 O24 1.240(3) . ?
C24 C25 1.445(3) . ?
C25 C26 1.329(4) . ?
N31 C34 1.348(3) . ?
N31 C32 1.349(3) . ?
C32 N33 1.336(5) . ?
C32 N31 1.349(3) 2_655 ?
C34 N36 1.336(3) . ?
C34 N35 1.340(3) . ?
N35 C34 1.340(3) 2_655 ?
S1A O2A 1.507(2) . ?
S1A C4A 1.777(3) . ?
S1A C3A 1.778(4) . ?
S1B O2B 1.481(2) . ?
S1B C3B 1.788(3) . ?
S1B C4B 1.797(4) . ?
S1B' O2B' 1.495(10) . ?
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
N21 H21 O2A 0.88 1.90 2.754(4) 162.3 7
N23 H23 N31 0.88 2.01 2.886(3) 177.8 1_545
N33 H33A O24 0.88 2.12 2.995(3) 175.6 1_565
N33 H33B O24 0.88 2.12 2.995(3) 175.6 2_665
N36 H36A O24 0.88 2.05 2.925(4) 169.7 .
N36 H36B O22 0.88 1.96 2.845(3) 177.8 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C7 0.4(4) . . . 5_565 ?
C11 C1 C2 C7 -178.9(3) . . . 5_565 ?
C2 C7 C8 C9 -1.6(4) 5_565 . . . ?
C2 C7 C8 C14 178.4(3) 5_565 . . . ?
C2 C1 C9 C8 -179.4(2) . . . . ?
C11 C1 C9 C8 -0.1(4) . . . . ?
C2 C1 C9 C9 -0.4(4) . . . 5_565 ?
C11 C1 C9 C9 178.8(3) . . . 5_565 ?
C7 C8 C9 C1 -179.4(2) . . . . ?
C14 C8 C9 C1 0.6(4) . . . . ?
C7 C8 C9 C9 1.6(4) . . . 5_565 ?
C14 C8 C9 C9 -178.4(3) . . . 5_565 ?
C2 C1 C11 O12 -3.1(4) . . . . ?
C9 C1 C11 O12 177.6(3) . . . . ?
C2 C1 C11 N13 177.6(2) . . . . ?
C9 C1 C11 N13 -1.7(4) . . . . ?
O12 C11 N13 C14 -176.1(3) . . . . ?
C1 C11 N13 C14 3.3(4) . . . . ?
O12 C11 N13 C26 1.2(4) . . . . ?
C1 C11 N13 C26 -179.4(2) . . . . ?
C11 N13 C14 O15 176.2(2) . . . . ?
C26 N13 C14 O15 -1.1(4) . . . . ?
C11 N13 C14 C8 -2.9(4) . . . . ?
C26 N13 C14 C8 179.8(2) . . . . ?
C7 C8 C14 O15 1.8(4) . . . . ?
C9 C8 C14 O15 -178.2(3) . . . . ?
C7 C8 C14 N13 -179.2(2) . . . . ?
C9 C8 C14 N13 0.8(4) . . . . ?
C26 N21 C22 O22 -177.3(3) . . . . ?
C26 N21 C22 N23 4.2(3) . . . . ?
O22 C22 N23 C24 173.3(3) . . . . ?
N21 C22 N23 C24 -8.3(4) . . . . ?
C22 N23 C24 O24 -174.8(2) . . . . ?
C22 N23 C24 C25 6.7(4) . . . . ?
O24 C24 C25 C26 -179.4(2) . . . . ?
N23 C24 C25 C26 -1.1(3) . . . . ?
C24 C25 C26 N21 -2.4(4) . . . . ?
C24 C25 C26 N13 176.8(2) . . . . ?
C22 N21 C26 C25 0.8(4) . . . . ?
C22 N21 C26 N13 -178.5(2) . . . . ?
C11 N13 C26 C25 91.0(3) . . . . ?
C14 N13 C26 C25 -91.5(3) . . . . ?
C11 N13 C26 N21 -89.6(3) . . . . ?
C14 N13 C26 N21 87.9(3) . . . . ?
C34 N31 C32 N33 179.64(15) . . . . ?
C34 N31 C32 N31 -0.36(15) . . . 2_655 ?
C32 N31 C34 N36 -177.82(19) . . . . ?
C32 N31 C34 N35 0.8(3) . . . . ?
N36 C34 N35 C34 178.2(3) . . . 2_655 ?
N31 C34 N35 C34 -0.43(17) . . . 2_655 ?
