#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:31:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180398 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/67/7206730.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_7206730
loop_
_publ_author_name
'Nauha, Elisa'
'Kolehmainen, Erkki'
'Nissinen, Maija'
_publ_section_title
;
 Packing incentives and a reliable N--H⋯N--pyridine synthon in
 co-crystallization of bipyridines with two agrochemical actives
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              6531
_journal_paper_doi               10.1039/c1ce05730h
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety
'2(C12 H14 N4 O4 S2), 1.5(C10 H8 N2), C2 H3 N'
_chemical_formula_sum            'C41 H43 N12 O8 S4'
_chemical_formula_weight         960.11
_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                108.694(4)
_cell_angle_beta                 95.323(3)
_cell_angle_gamma                109.312(4)
_cell_formula_units_Z            2
_cell_length_a                   10.6193(3)
_cell_length_b                   15.0562(4)
_cell_length_c                   16.2601(4)
_cell_measurement_temperature    173(2)
_cell_volume                     2265.87(15)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10805
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         66.97
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    2.480
_exptl_absorpt_correction_T_max  0.7895
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo (Otwinowski, Borek, Majewski & Minor,2003)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1002
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         7733
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0517
_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)+(0.0609P)²+2.0584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                5900
_reflns_number_total             7733
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05730h.txt
_cod_data_source_block           TM-22bp
_cod_original_cell_volume        2265.87(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7206730
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
S1 S 0.52467(10) 0.79919(6) 0.36781(5) 0.0537(3) Uani 1 1 d .
S2 S 0.78623(7) 0.92107(6) 0.10033(5) 0.0393(2) Uani 1 1 d .
S3 S 0.48577(13) 0.64022(7) 0.50102(5) 0.0651(3) Uani 1 1 d .
S4 S 0.90597(8) 0.78347(6) 0.83007(6) 0.0444(2) Uani 1 1 d .
O1 O 0.6729(2) 1.10580(16) 0.33620(13) 0.0463(6) Uani 1 1 d .
O2 O 0.7640(2) 1.15755(17) 0.48222(13) 0.0482(6) Uani 1 1 d .
O3 O 0.58950(19) 1.15657(15) 0.17227(13) 0.0337(4) Uani 1 1 d .
O4 O 0.8118(2) 1.26190(15) 0.20624(15) 0.0424(5) Uani 1 1 d .
O5 O 0.6971(2) 0.95216(16) 0.72444(13) 0.0464(6) Uani 1 1 d .
O6 O 0.6977(2) 1.00098(15) 0.60756(13) 0.0412(5) Uani 1 1 d .
O7 O 0.71268(19) 1.01966(15) 0.92307(12) 0.0345(4) Uani 1 1 d .
O8 O 0.9272(2) 1.12299(15) 0.92932(14) 0.0414(5) Uani 1 1 d .
N1 N 0.6355(3) 0.9955(2) 0.40995(16) 0.0403(6) Uani 1 1 d D
H1N H 0.663(3) 0.993(3) 0.4627(15) 0.048 Uiso 1 1 d D
N2 N 0.5313(3) 0.90622(19) 0.26198(15) 0.0368(6) Uani 1 1 d D
H2N H 0.570(3) 0.9661(17) 0.259(2) 0.044 Uiso 1 1 d D
N3 N 0.5625(2) 0.96020(18) 0.11891(15) 0.0291(5) Uani 1 1 d D
H3N H 0.518(3) 1.002(2) 0.124(2) 0.035 Uiso 1 1 d D
N4 N 0.7630(2) 1.09835(18) 0.14544(15) 0.0311(5) Uani 1 1 d D
H4N H 0.8533(19) 1.124(2) 0.152(2) 0.037 Uiso 1 1 d D
N5 N 0.5927(3) 0.83702(19) 0.58182(16) 0.0388(6) Uani 1 1 d D
H5N H 0.575(3) 0.830(3) 0.5245(14) 0.047 Uiso 1 1 d D
N6 N 0.5759(3) 0.75134(19) 0.67708(15) 0.0350(6) Uani 1 1 d D
H6N H 0.618(3) 0.8146(16) 0.7155(18) 0.042 Uiso 1 1 d D
N7 N 0.6831(2) 0.82179(17) 0.85312(14) 0.0282(5) Uani 1 1 d D
H7N H 0.641(3) 0.864(2) 0.8728(18) 0.034 Uiso 1 1 d D
N8 N 0.8864(2) 0.96158(18) 0.89616(15) 0.0320(5) Uani 1 1 d D
H8N H 0.9780(19) 0.988(2) 0.897(2) 0.038 Uiso 1 1 d D
C1 C 0.8272(4) 1.2603(3) 0.4852(2) 0.0563(9) Uani 1 1 d .
H1A H 0.8787 1.2603 0.4383 0.084 Uiso 1 1 calc R
H1B H 0.8894 1.3036 0.5434 0.084 Uiso 1 1 calc R
H1C H 0.7560 1.2864 0.4760 0.084 Uiso 1 1 calc R
C2 C 0.6901(3) 1.0886(2) 0.4031(2) 0.0387(7) Uani 1 1 d .
C3 C 0.5627(3) 0.9013(2) 0.34205(19) 0.0384(7) Uani 1 1 d .
C4 C 0.4669(3) 0.8282(2) 0.17751(17) 0.0313(6) Uani 1 1 d .
C5 C 0.3848(3) 0.7286(2) 0.16299(19) 0.0368(7) Uani 1 1 d .
H5 H 0.3667 0.7090 0.2121 0.044 Uiso 1 1 calc R
C6 C 0.3293(3) 0.6580(2) 0.07654(19) 0.0360(7) Uani 1 1 d .
H6 H 0.2734 0.5900 0.0669 0.043 Uiso 1 1 calc R
C7 C 0.3541(3) 0.6851(2) 0.00481(18) 0.0339(6) Uani 1 1 d .
H7 H 0.3181 0.6355 -0.0540 0.041 Uiso 1 1 calc R
C8 C 0.4316(3) 0.7849(2) 0.01831(18) 0.0313(6) Uani 1 1 d .
H8 H 0.4470 0.8042 -0.0312 0.038 Uiso 1 1 calc R
C9 C 0.4864(3) 0.8562(2) 0.10381(17) 0.0281(6) Uani 1 1 d .
C10 C 0.6970(3) 0.9955(2) 0.12198(17) 0.0286(6) Uani 1 1 d .
C11 C 0.7094(3) 1.1715(2) 0.17518(18) 0.0308(6) Uani 1 1 d .
C12 C 0.7762(3) 1.3487(2) 0.2470(2) 0.0488(8) Uani 1 1 d .
H12A H 0.7034 1.3482 0.2050 0.073 Uiso 1 1 calc R
H12B H 0.8570 1.4113 0.2627 0.073 Uiso 1 1 calc R
H12C H 0.7443 1.3450 0.3009 0.073 Uiso 1 1 calc R
C13 C 0.7838(4) 1.1040(2) 0.6676(2) 0.0482(8) Uani 1 1 d .
H13A H 0.8711 1.1051 0.6945 0.072 Uiso 1 1 calc R
H13B H 0.7374 1.1273 0.7145 0.072 Uiso 1 1 calc R
H13C H 0.8009 1.1490 0.6341 0.072 Uiso 1 1 calc R
C14 C 0.6658(3) 0.9320(2) 0.64538(19) 0.0373(7) Uani 1 1 d .
C15 C 0.5527(3) 0.7444(2) 0.59259(19) 0.0391(7) Uani 1 1 d .
C16 C 0.5495(3) 0.6780(2) 0.71616(18) 0.0308(6) Uani 1 1 d .
C17 C 0.4749(3) 0.5743(2) 0.6726(2) 0.0387(7) Uani 1 1 d .
H17 H 0.4408 0.5466 0.6100 0.046 Uiso 1 1 calc R
C18 C 0.4503(3) 0.5113(2) 0.7205(2) 0.0425(7) Uani 1 1 d .
H18 H 0.3992 0.4406 0.6903 0.051 Uiso 1 1 calc R
C19 C 0.4989(3) 0.5499(2) 0.8113(2) 0.0400(7) Uani 1 1 d .
H19 H 0.4796 0.5064 0.8437 0.048 Uiso 1 1 calc R
C20 C 0.5762(3) 0.6527(2) 0.8553(2) 0.0351(6) Uani 1 1 d .
H20 H 0.6117 0.6795 0.9178 0.042 Uiso 1 1 calc R
C21 C 0.6015(3) 0.7156(2) 0.80833(18) 0.0291(6) Uani 1 1 d .
C22 C 0.8184(3) 0.8580(2) 0.86138(18) 0.0304(6) Uani 1 1 d .
C23 C 0.8302(3) 1.0342(2) 0.91709(18) 0.0311(6) Uani 1 1 d .
C24 C 0.8879(3) 1.2091(2) 0.9539(2) 0.0468(8) Uani 1 1 d .
H24A H 0.8675 1.2221 1.0132 0.070 Uiso 1 1 calc R
H24B H 0.8065 1.1950 0.9105 0.070 Uiso 1 1 calc R
H24C H 0.9631 1.2688 0.9548 0.070 Uiso 1 1 calc R
N101 N 1.0876(3) 0.6251(2) 0.26998(18) 0.0514(7) Uani 1 1 d .
N102 N 0.8292(3) 0.5747(2) 0.08377(17) 0.0453(6) Uani 1 1 d .
C101 C 1.1819(4) 0.5894(3) 0.2889(2) 0.0618(10) Uani 1 1 d .
H101 H 1.2422 0.6241 0.3460 0.074 Uiso 1 1 calc R
C102 C 1.1976(4) 0.5064(3) 0.2318(2) 0.0564(9) Uani 1 1 d .
H102 H 1.2655 0.4839 0.2494 0.068 Uiso 1 1 calc R
C103 C 1.1133(3) 0.4568(3) 0.1489(2) 0.0478(8) Uani 1 1 d .
H103 H 1.1215 0.3990 0.1077 0.057 Uiso 1 1 calc R
C104 C 1.0158(3) 0.4921(2) 0.1260(2) 0.0393(7) Uani 1 1 d .
H104 H 0.9574 0.4598 0.0683 0.047 Uiso 1 1 calc R
C105 C 1.0046(3) 0.5757(2) 0.1886(2) 0.0375(7) Uani 1 1 d .
C106 C 0.8987(3) 0.6142(2) 0.1685(2) 0.0374(7) Uani 1 1 d .
C107 C 0.8721(4) 0.6870(3) 0.2335(2) 0.0571(9) Uani 1 1 d .
H107 H 0.9216 0.7136 0.2935 0.068 Uiso 1 1 calc R
C108 C 0.7728(4) 0.7205(3) 0.2102(3) 0.0677(11) Uani 1 1 d .
H108 H 0.7540 0.7709 0.2540 0.081 Uiso 1 1 calc R
C109 C 0.7020(4) 0.6806(3) 0.1238(3) 0.0539(9) Uani 1 1 d .
H109 H 0.6334 0.7024 0.1061 0.065 Uiso 1 1 calc R
C110 C 0.7330(4) 0.6083(3) 0.0637(2) 0.0517(9) Uani 1 1 d .
H110 H 0.6831 0.5801 0.0037 0.062 Uiso 1 1 calc R
N200 N 0.9571(5) 0.9939(6) 0.3872(3) 0.137(3) Uani 1 1 d .
C201 C 0.9931(10) 1.0637(11) 0.3440(5) 0.167(6) Uani 1 1 d .
H201 H 0.9560 1.0408 0.2821 0.200 Uiso 1 1 calc R
C202 C 1.0767(11) 1.1596(11) 0.3867(9) 0.166(5) Uani 1 1 d .
H202 H 1.0983 1.2035 0.3547 0.199 Uiso 1 1 calc R
C203 C 1.1332(8) 1.1973(9) 0.4770(8) 0.163(4) Uani 1 1 d .
H203 H 1.1929 1.2663 0.5072 0.196 Uiso 1 1 calc R
C204 C 1.1013(6) 1.1339(7) 0.5203(4) 0.110(2) Uani 1 1 d .
H204 H 1.1381 1.1581 0.5825 0.132 Uiso 1 1 calc R
C205 C 1.0161(5) 1.0345(6) 0.4761(3) 0.100(2) Uani 1 1 d .
N300 N 0.8853(10) 0.5410(7) 0.4366(6) 0.287(7) Uani 1 1 d .
C301 C 0.8704(9) 0.5508(6) 0.5090(5) 0.173(4) Uani 1 1 d .
C302 C 0.8389(9) 0.5740(6) 0.5904(5) 0.159(4) Uani 1 1 d .
H30A H 0.7423 0.5652 0.5835 0.239 Uiso 1 1 calc R
H30B H 0.8964 0.6447 0.6278 0.239 Uiso 1 1 calc R
H30C H 0.8551 0.5290 0.6185 0.239 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_3
C2 O2 C1 115.4(2) .
C11 O4 C12 116.2(2) .
C14 O6 C13 115.4(2) .
C23 O8 C24 116.1(2) .
C2 N1 C3 128.3(3) .
C2 N1 H1N 116(2) .
C3 N1 H1N 115(2) .
C3 N2 C4 130.5(3) .
C3 N2 H2N 115(2) .
C4 N2 H2N 113(2) .
C10 N3 C9 122.0(2) .
C10 N3 H3N 119(2) .
C9 N3 H3N 119(2) .
C10 N4 C11 127.1(2) .
C10 N4 H4N 119(2) .
C11 N4 H4N 113(2) .
C14 N5 C15 128.0(2) .
C14 N5 H5N 119(2) .
C15 N5 H5N 113(2) .
C15 N6 C16 132.7(3) .
C15 N6 H6N 113(2) .
C16 N6 H6N 114(2) .
C22 N7 C21 121.3(2) .
C22 N7 H7N 120(2) .
C21 N7 H7N 119(2) .
C22 N8 C23 127.6(2) .
C22 N8 H8N 119(2) .
C23 N8 H8N 113(2) .
O2 C1 H1A 109.5 .
O2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
O2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
O1 C2 O2 125.0(3) .
O1 C2 N1 125.7(3) .
O2 C2 N1 109.3(3) .
N2 C3 N1 114.0(3) .
N2 C3 S1 128.0(2) .
N1 C3 S1 118.0(2) .
C5 C4 C9 118.9(2) .
C5 C4 N2 125.1(2) .
C9 C4 N2 116.0(2) .
C6 C5 C4 119.8(3) .
C6 C5 H5 120.1 .
C4 C5 H5 120.1 .
C7 C6 C5 120.9(3) .
C7 C6 H6 119.6 .
C5 C6 H6 119.6 .
C6 C7 C8 119.9(3) .
C6 C7 H7 120.1 .
C8 C7 H7 120.1 .
C9 C8 C7 119.9(3) .
C9 C8 H8 120.1 .
C7 C8 H8 120.1 .
C8 C9 C4 120.6(3) .
C8 C9 N3 120.6(2) .
C4 C9 N3 118.8(2) .
N3 C10 N4 117.3(2) .
N3 C10 S2 123.1(2) .
N4 C10 S2 119.5(2) .
O3 C11 O4 125.7(3) .
O3 C11 N4 126.1(3) .
O4 C11 N4 108.3(2) .
O4 C12 H12A 109.5 .
O4 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
O4 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
O6 C13 H13A 109.5 .
O6 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
O6 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
O5 C14 O6 123.9(3) .
O5 C14 N5 125.8(3) .
O6 C14 N5 110.3(2) .
N6 C15 N5 114.7(3) .
N6 C15 S3 128.1(2) .
N5 C15 S3 117.2(2) .
C17 C16 C21 118.3(3) .
C17 C16 N6 126.3(3) .
C21 C16 N6 115.5(2) .
C18 C17 C16 120.1(3) .
C18 C17 H17 119.9 .
C16 C17 H17 119.9 .
C19 C18 C17 120.8(3) .
C19 C18 H18 119.6 .
C17 C18 H18 119.6 .
C18 C19 C20 119.7(3) .
C18 C19 H19 120.1 .
C20 C19 H19 120.1 .
C21 C20 C19 119.8(3) .
C21 C20 H20 120.1 .
C19 C20 H20 120.1 .
C20 C21 C16 121.2(3) .
C20 C21 N7 120.2(2) .
C16 C21 N7 118.6(2) .
N7 C22 N8 117.4(2) .
N7 C22 S4 123.0(2) .
N8 C22 S4 119.6(2) .
O7 C23 O8 125.9(3) .
O7 C23 N8 126.0(3) .
O8 C23 N8 108.1(2) .
O8 C24 H24A 109.5 .
O8 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
O8 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
C101 N101 C105 116.7(3) .
C106 N102 C110 117.8(3) .
N101 C101 C102 124.6(3) .
N101 C101 H101 117.7 .
C102 C101 H101 117.7 .
C103 C102 C101 118.4(3) .
C103 C102 H102 120.8 .
C101 C102 H102 120.8 .
C102 C103 C104 118.9(3) .
C102 C103 H103 120.5 .
C104 C103 H103 120.5 .
C103 C104 C105 119.1(3) .
C103 C104 H104 120.5 .
C105 C104 H104 120.5 .
N101 C105 C104 122.2(3) .
N101 C105 C106 116.6(3) .
C104 C105 C106 121.2(3) .
N102 C106 C107 121.4(3) .
N102 C106 C105 116.5(3) .
C107 C106 C105 122.0(3) .
C108 C107 C106 119.2(3) .
C108 C107 H107 120.4 .
C106 C107 H107 120.4 .
C109 C108 C107 119.5(4) .
C109 C108 H108 120.3 .
C107 C108 H108 120.3 .
C110 C109 C108 117.9(3) .
C110 C109 H109 121.1 .
C108 C109 H109 121.1 .
N102 C110 C109 124.2(3) .
N102 C110 H110 117.9 .
C109 C110 H110 117.9 .
C205 N200 C201 114.1(7) .
C202 C201 N200 122.4(9) .
C202 C201 H201 118.8 .
N200 C201 H201 118.8 .
C201 C202 C203 121.4(13) .
C201 C202 H202 119.3 .
C203 C202 H202 119.3 .
C204 C203 C202 118.1(11) .
C204 C203 H203 121.0 .
C202 C203 H203 121.0 .
C203 C204 C205 120.6(7) .
C203 C204 H204 119.7 .
C205 C204 H204 119.7 .
N200 C205 C204 123.5(7) .
N200 C205 C205 116.4(8) 2_776
C204 C205 C205 120.0(6) 2_776
N300 C301 C302 168.2(15) .
C301 C302 H30A 109.5 .
C301 C302 H30B 109.5 .
H30A C302 H30B 109.5 .
C301 C302 H30C 109.5 .
H30A C302 H30C 109.5 .
H30B C302 H30C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C3 1.655(3) .
S2 C10 1.670(3) .
S3 C15 1.659(3) .
S4 C22 1.672(3) .
O1 C2 1.208(4) .
O2 C2 1.329(4) .
O2 C1 1.451(4) .
O3 C11 1.211(3) .
O4 C11 1.329(3) .
O4 C12 1.451(4) .
O5 C14 1.208(3) .
O6 C14 1.336(4) .
O6 C13 1.456(4) .
O7 C23 1.213(3) .
O8 C23 1.330(3) .
O8 C24 1.439(4) .
N1 C2 1.374(4) .
N1 C3 1.393(4) .
N1 H1N 0.897(18) .
N2 C3 1.345(4) .
N2 C4 1.412(4) .
N2 H2N 0.877(18) .
N3 C10 1.339(3) .
N3 C9 1.430(4) .
N3 H3N 0.890(18) .
N4 C10 1.374(4) .
N4 C11 1.377(4) .
N4 H4N 0.888(18) .
N5 C14 1.373(4) .
N5 C15 1.391(4) .
N5 H5N 0.897(18) .
N6 C15 1.337(4) .
N6 C16 1.406(4) .
N6 H6N 0.884(18) .
N7 C22 1.334(4) .
N7 C21 1.434(4) .
N7 H7N 0.890(18) .
N8 C22 1.374(4) .
N8 C23 1.377(4) .
N8 H8N 0.917(18) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C4 C5 1.390(4) .
C4 C9 1.403(4) .
C5 C6 1.389(4) .
C5 H5 0.9500 .
C6 C7 1.374(4) .
C6 H6 0.9500 .
C7 C8 1.386(4) .
C7 H7 0.9500 .
C8 C9 1.380(4) .
C8 H8 0.9500 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C16 C17 1.391(4) .
C16 C21 1.403(4) .
C17 C18 1.387(4) .
C17 H17 0.9500 .
C18 C19 1.376(4) .
C18 H18 0.9500 .
C19 C20 1.386(4) .
C19 H19 0.9500 .
C20 C21 1.373(4) .
C20 H20 0.9500 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
N101 C101 1.338(5) .
N101 C105 1.341(4) .
N102 C106 1.338(4) .
N102 C110 1.339(4) .
C101 C102 1.369(5) .
C101 H101 0.9500 .
C102 C103 1.365(5) .
C102 H102 0.9500 .
C103 C104 1.383(4) .
C103 H103 0.9500 .
C104 C105 1.391(4) .
C104 H104 0.9500 .
C105 C106 1.481(4) .
C106 C107 1.385(5) .
C107 C108 1.381(5) .
C107 H107 0.9500 .
C108 C109 1.366(5) .
C108 H108 0.9500 .
C109 C110 1.364(5) .
C109 H109 0.9500 .
C110 H110 0.9500 .
N200 C205 1.366(6) .
N200 C201 1.415(13) .
C201 C202 1.323(15) .
C201 H201 0.9500 .
C202 C203 1.383(13) .
C202 H202 0.9500 .
C203 C204 1.336(12) .
C203 H203 0.9500 .
C204 C205 1.367(10) .
C204 H204 0.9500 .
C205 C205 1.462(13) 2_776
N300 C301 1.171(11) .
C301 C302 1.360(10) .
C302 H30A 0.9800 .
C302 H30B 0.9800 .
C302 H30C 0.9800 .
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 H1N O6 0.897(18) 2.31(2) 3.189(3) 167(3) .
N2 H2N O1 0.877(18) 1.93(3) 2.664(3) 141(3) .
N2 H2N N3 0.877(18) 2.25(3) 2.713(3) 113(2) .
N3 H3N O3 0.890(18) 2.04(3) 2.707(3) 130(3) .
N3 H3N O7 0.890(18) 2.38(3) 3.074(3) 135(3) 2_676
N4 H4N S4 0.888(18) 2.410(19) 3.291(2) 171(3) 2_776
N5 H5N S1 0.897(18) 2.413(19) 3.309(2) 176(3) .
N6 H6N O5 0.884(18) 1.91(2) 2.672(3) 143(3) .
N6 H6N N7 0.884(18) 2.24(3) 2.695(3) 112(2) .
N7 H7N O7 0.890(18) 2.05(3) 2.722(3) 131(3) .
N7 H7N O3 0.890(18) 2.38(3) 3.024(3) 130(2) 2_676
N8 H8N S2 0.917(18) 2.412(19) 3.323(2) 172(3) 2_776
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
C1 O2 C2 O1 -0.2(5) .
C1 O2 C2 N1 -179.4(3) .
C3 N1 C2 O1 7.3(5) .
C3 N1 C2 O2 -173.5(3) .
C4 N2 C3 N1 175.6(3) .
C4 N2 C3 S1 -4.7(5) .
C2 N1 C3 N2 -7.6(5) .
C2 N1 C3 S1 172.7(3) .
C3 N2 C4 C5 20.9(5) .
C3 N2 C4 C9 -160.9(3) .
C9 C4 C5 C6 3.1(4) .
N2 C4 C5 C6 -178.7(3) .
C4 C5 C6 C7 -0.2(5) .
C5 C6 C7 C8 -2.2(4) .
C6 C7 C8 C9 1.6(4) .
C7 C8 C9 C4 1.4(4) .
C7 C8 C9 N3 -177.8(2) .
C5 C4 C9 C8 -3.7(4) .
N2 C4 C9 C8 177.9(2) .
C5 C4 C9 N3 175.4(3) .
N2 C4 C9 N3 -2.9(4) .
C10 N3 C9 C8 -86.7(3) .
C10 N3 C9 C4 94.1(3) .
C9 N3 C10 N4 -173.8(2) .
C9 N3 C10 S2 5.3(4) .
C11 N4 C10 N3 7.2(4) .
C11 N4 C10 S2 -172.0(2) .
C12 O4 C11 O3 5.7(4) .
C12 O4 C11 N4 -175.4(2) .
C10 N4 C11 O3 -12.7(4) .
C10 N4 C11 O4 168.5(2) .
C13 O6 C14 O5 4.6(4) .
C13 O6 C14 N5 -175.9(3) .
C15 N5 C14 O5 -7.6(5) .
C15 N5 C14 O6 172.9(3) .
C16 N6 C15 N5 178.9(3) .
C16 N6 C15 S3 -2.3(5) .
C14 N5 C15 N6 8.2(5) .
C14 N5 C15 S3 -170.8(3) .
C15 N6 C16 C17 -7.7(5) .
C15 N6 C16 C21 174.1(3) .
C21 C16 C17 C18 1.8(4) .
N6 C16 C17 C18 -176.3(3) .
C16 C17 C18 C19 -0.1(5) .
C17 C18 C19 C20 -1.5(5) .
C18 C19 C20 C21 1.3(4) .
C19 C20 C21 C16 0.5(4) .
C19 C20 C21 N7 -179.1(3) .
C17 C16 C21 C20 -2.0(4) .
N6 C16 C21 C20 176.3(3) .
C17 C16 C21 N7 177.5(3) .
N6 C16 C21 N7 -4.1(4) .
C22 N7 C21 C20 90.5(3) .
C22 N7 C21 C16 -89.0(3) .
C21 N7 C22 N8 172.8(2) .
C21 N7 C22 S4 -6.2(4) .
C23 N8 C22 N7 -6.0(4) .
C23 N8 C22 S4 173.1(2) .
C24 O8 C23 O7 1.6(4) .
C24 O8 C23 N8 -178.6(2) .
C22 N8 C23 O7 13.8(5) .
C22 N8 C23 O8 -166.0(2) .
C105 N101 C101 C102 -0.8(6) .
N101 C101 C102 C103 1.2(6) .
C101 C102 C103 C104 0.0(5) .
C102 C103 C104 C105 -1.4(5) .
C101 N101 C105 C104 -0.8(5) .
C101 N101 C105 C106 178.9(3) .
C103 C104 C105 N101 1.8(5) .
C103 C104 C105 C106 -177.8(3) .
C110 N102 C106 C107 0.3(5) .
C110 N102 C106 C105 -179.9(3) .
N101 C105 C106 N102 170.6(3) .
C104 C105 C106 N102 -9.7(4) .
N101 C105 C106 C107 -9.6(5) .
C104 C105 C106 C107 170.1(3) .
N102 C106 C107 C108 -0.8(5) .
C105 C106 C107 C108 179.4(3) .
C106 C107 C108 C109 0.6(6) .
C107 C108 C109 C110 0.1(6) .
C106 N102 C110 C109 0.4(5) .
C108 C109 C110 N102 -0.6(6) .
C205 N200 C201 C202 0.0(11) .
N200 C201 C202 C203 -0.4(14) .
C201 C202 C203 C204 0.1(13) .
C202 C203 C204 C205 0.6(10) .
C201 N200 C205 C204 0.7(7) .
C201 N200 C205 C205 -179.2(5) 2_776
C203 C204 C205 N200 -1.0(9) .
C203 C204 C205 C205 178.9(6) 2_776
