#------------------------------------------------------------------------------
#$Date: 2019-12-23 21:07:19 +0200 (Mon, 23 Dec 2019) $
#$Revision: 245520 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/72/4517261.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_4517261
loop_
_publ_author_name
'Adam Duong'
'Sanil Rajak'
'Alexandre A. Tremblay'
'Thierry Maris'
'James D. Wuest'
_publ_contact_author_email       thierry.maris@umontreal.ca
_publ_contact_author_id_orcid    0000-0001-9731-4046
_publ_contact_author_name        'Thierry Maris'
_publ_contact_author_phone       '514 340 4711 2579'
_publ_section_title
;
 Molecular Organization in Crystals of Bis(diaminotriazinyl)- Substituted
 Derivatives of Benzene, Pyridine, and Pyrazine
;
_journal_name_full               'Crystal growth and Design'
_journal_page_first              1299
_journal_paper_doi               10.1021/acs.cgd.8b01694
_journal_volume                  19
_journal_year                    2019
_chemical_formula_moiety         '2(C11 H11 N11), 5(C2 H6 O S), H2 O'
_chemical_formula_sum            'C32 H54 N22 O6 S5'
_chemical_formula_weight         1003.27
_chemical_name_common
;
6,6'-(pyridine-2,6-diyl)bis(1,3,5-triazine-2,4-diamine) 
dimethyl sulfoxide solvate hemihydrate
;
_chemical_name_systematic
;
6,6'-(pyridine-2,6-diyl)bis(1,3,5-triazine-2,4-diamine) 
dimethyl sulfoxide solvate hemihydrate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5811(3)
_cell_length_b                   9.7851(2)
_cell_length_c                   30.4229(5)
_cell_measurement_reflns_used    9720
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.293
_cell_measurement_theta_min      2.905
_cell_volume                     4638.36(15)
_computing_cell_refinement
;
SAINT (2009) Release V7.68A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
 APEX2 (2009) ; Bruker Molecular Analysis Research Tool.
 Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2009) Release V7.68A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD Area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circles diffractometer'
_diffrn_measurement_device_type  'Bruker Smart Platform'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            288993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.266
_diffrn_reflns_theta_min         2.905
_diffrn_source                   'Incoatec I\muS Microsource '
_diffrn_source_target            Cu
_diffrn_source_type              'Microfocus Source'
_exptl_absorpt_coefficient_mu    2.880
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.1074 before and 0.0640 after correction. 
The Ratio of minimum to maximum transmission is 0.7953. 
The λ/2 correction factor is 0.0015.'
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.259
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4497
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.258
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0481P)²+8.0113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1530
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4392
_reflns_number_total             4497
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            6_adam65.cif
_cod_data_source_block           adam65
_cod_database_code               4517261
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y+1/2, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y-1/2, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1248(2) 0.6656(3) 1.03217(9) 0.0305(6) Uani 1 1 d . . . . .
C2 C 0.1600(2) 0.5547(3) 1.05457(9) 0.0313(6) Uani 1 1 d . . . . .
H2 H 0.182680 0.565536 1.083355 0.038 Uiso 1 1 calc R . . . .
C3 C 0.1614(2) 0.4288(3) 1.03405(9) 0.0335(7) Uani 1 1 d . . . . .
H3 H 0.184019 0.350978 1.048670 0.040 Uiso 1 1 calc R . . . .
C4 C 0.1292(2) 0.4181(3) 0.99191(9) 0.0336(7) Uani 1 1 d . . . . .
H4 H 0.129744 0.332756 0.977038 0.040 Uiso 1 1 calc R . . . .
C5 C 0.0960(2) 0.5338(3) 0.97148(9) 0.0307(6) Uani 1 1 d . . . . .
C6 C 0.0607(2) 0.5230(3) 0.92558(9) 0.0316(7) Uani 1 1 d . . . . .
C7 C 0.0475(3) 0.4035(3) 0.86241(9) 0.0400(8) Uani 1 1 d . . . . .
C8 C -0.0184(2) 0.6080(3) 0.86970(9) 0.0354(7) Uani 1 1 d . . . . .
C9 C 0.1217(2) 0.8026(3) 1.05465(9) 0.0304(6) Uani 1 1 d . . . . .
C10 C 0.1611(2) 0.9353(3) 1.11175(10) 0.0345(7) Uani 1 1 d . . . . .
C11 C 0.0784(2) 1.0234(3) 1.05758(9) 0.0320(7) Uani 1 1 d . . . . .
N1 N 0.09293(17) 0.6568(2) 0.99119(7) 0.0304(5) Uani 1 1 d . . . . .
N2 N 0.07961(19) 0.4085(2) 0.90376(8) 0.0358(6) Uani 1 1 d . . . . .
N3 N -0.0010(2) 0.5008(3) 0.84335(8) 0.0399(7) Uani 1 1 d . . . . .
N4 N 0.01331(18) 0.6263(2) 0.91086(7) 0.0321(6) Uani 1 1 d . . . . .
N5 N 0.0657(2) 0.2927(3) 0.83825(8) 0.0495(8) Uani 1 1 d . . . . .
H5A H 0.046135 0.285919 0.811203 0.059 Uiso 1 1 calc R . . . .
H5B H 0.097229 0.226630 0.849434 0.059 Uiso 1 1 calc R . . . .
N6 N -0.07051(19) 0.7042(2) 0.85417(8) 0.0377(6) Uani 1 1 d . . . . .
H6A H -0.092214 0.696464 0.827588 0.045 Uiso 1 1 calc R . . . .
H6B H -0.083276 0.775679 0.870483 0.045 Uiso 1 1 calc R . . . .
N7 N 0.16391(18) 0.8103(2) 1.09262(8) 0.0333(6) Uani 1 1 d . . . . .
N8 N 0.11938(18) 1.0443(2) 1.09609(8) 0.0333(6) Uani 1 1 d . . . . .
N9 N 0.07838(18) 0.9028(2) 1.03524(8) 0.0323(6) Uani 1 1 d . . . . .
N10 N 0.2044(2) 0.9504(3) 1.14918(9) 0.0435(7) Uani 1 1 d . . . . .
H10A H 0.204742 1.029960 1.162649 0.052 Uiso 1 1 calc R . . . .
H10B H 0.232586 0.880792 1.160444 0.052 Uiso 1 1 calc R . . . .
N11 N 0.03644(18) 1.1273(2) 1.03974(8) 0.0351(6) Uani 1 1 d . . . . .
H11A H 0.035817 1.207274 1.052985 0.042 Uiso 1 1 calc R . . . .
H11B H 0.009197 1.116388 1.014649 0.042 Uiso 1 1 calc R . . . .
S1 S 0.13140(5) -0.03406(7) 0.89104(2) 0.0342(2) Uani 1 1 d . . . . .
O1 O 0.17484(16) 0.0441(2) 0.85439(7) 0.0388(5) Uani 1 1 d . . . . .
C12 C 0.1981(2) -0.1761(3) 0.90438(10) 0.0366(7) Uani 1 1 d . . . . .
H12A H 0.193745 -0.245203 0.881165 0.055 Uiso 1 1 calc GR . . . .
H12B H 0.179444 -0.215738 0.932386 0.055 Uiso 1 1 calc GR . . . .
H12C H 0.257793 -0.145572 0.906937 0.055 Uiso 1 1 calc GR . . . .
C13 C 0.1522(3) 0.0626(3) 0.93969(11) 0.0479(9) Uani 1 1 d . . . . .
H13A H 0.214062 0.078299 0.942499 0.072 Uiso 1 1 calc GR . . . .
H13B H 0.131489 0.011988 0.965384 0.072 Uiso 1 1 calc GR . . . .
H13C H 0.122394 0.150665 0.937891 0.072 Uiso 1 1 calc GR . . . .
O2 O -0.21172(17) 0.7787(2) 0.79961(7) 0.0441(6) Uani 1 1 d . . . A 1
S2 S -0.28263(10) 0.75806(11) 0.76383(4) 0.0381(4) Uani 0.634(3) 1 d D . . A 1
C14 C -0.3503(5) 0.9026(6) 0.7664(2) 0.064(2) Uani 0.634(3) 1 d D . . A 1
H14A H -0.315374 0.985871 0.765272 0.097 Uiso 0.634(3) 1 calc GR . . A 1
H14B H -0.382955 0.900783 0.793910 0.097 Uiso 0.634(3) 1 calc GR . . A 1
H14C H -0.390007 0.901426 0.741432 0.097 Uiso 0.634(3) 1 calc GR . . A 1
C15 C -0.2296(5) 0.7900(10) 0.71358(18) 0.057(2) Uani 0.634(3) 1 d D . . A 1
H15A H -0.205568 0.882543 0.713917 0.085 Uiso 0.634(3) 1 calc GR . . A 1
H15B H -0.270563 0.781676 0.689289 0.085 Uiso 0.634(3) 1 calc GR . . A 1
H15C H -0.183199 0.723472 0.709653 0.085 Uiso 0.634(3) 1 calc GR . . A 1
S2B S -0.20622(14) 0.85674(19) 0.75557(6) 0.0303(6) Uani 0.366(3) 1 d D . . A 2
C14B C -0.3087(4) 0.9325(8) 0.7512(3) 0.033(2) Uani 0.366(3) 1 d D . . A 2
H14D H -0.328822 1.008630 0.732977 0.050 Uiso 0.366(3) 1 d R . . A 2
H14E H -0.317112 0.954939 0.782297 0.050 Uiso 0.366(3) 1 d R . . A 2
H14F H -0.341322 0.849919 0.743927 0.050 Uiso 0.366(3) 1 d R . . A 2
C15B C -0.2116(12) 0.7310(14) 0.7145(4) 0.057(4) Uani 0.366(3) 1 d D . . A 2
H15D H -0.259578 0.669202 0.720666 0.085 Uiso 0.366(3) 1 calc GR . . A 2
H15E H -0.157849 0.678909 0.714120 0.085 Uiso 0.366(3) 1 calc GR . . A 2
H15F H -0.220231 0.774696 0.685886 0.085 Uiso 0.366(3) 1 calc GR . . A 2
O3 O 0.0252(3) 0.2074(4) 0.7490(2) 0.0358(15) Uani 0.5 1 d . . . . .
S3 S -0.05444(11) 0.05957(14) 0.74804(5) 0.0327(3) Uani 0.5 1 d . . . B -1
C17 C 0.0048(3) -0.0216(3) 0.70608(10) 0.0446(8) Uani 1 1 d . . . B -1
H17A H -0.014789 0.011286 0.677365 0.067 Uiso 1 1 calc GR . . B -1
H17B H -0.003709 -0.120709 0.707902 0.067 Uiso 1 1 calc GR . . B -1
H17C H 0.065933 -0.000622 0.709665 0.067 Uiso 1 1 calc GR . . B -1
O4 O 0.000000 0.6277(4) 0.750000 0.0618(12) Uani 1 2 d S T P . .
H4A H 0.001(3) 0.574(5) 0.7743(15) 0.084(16) 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 0.0181 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_1
_geom_angle_site_symmetry_3
C2 C1 C9 118.9(3) . .
N1 C1 C2 123.3(3) . .
N1 C1 C9 117.8(2) . .
C1 C2 H2 120.7 . .
C3 C2 C1 118.6(3) . .
C3 C2 H2 120.7 . .
C2 C3 H3 120.6 . .
C4 C3 C2 118.8(3) . .
C4 C3 H3 120.6 . .
C3 C4 H4 120.4 . .
C3 C4 C5 119.2(3) . .
C5 C4 H4 120.4 . .
C4 C5 C6 119.6(3) . .
N1 C5 C4 122.8(3) . .
N1 C5 C6 117.6(2) . .
N2 C6 C5 116.1(3) . .
N4 C6 C5 117.6(2) . .
N4 C6 N2 126.4(3) . .
N3 C7 N2 125.5(3) . .
N5 C7 N2 117.4(3) . .
N5 C7 N3 117.0(3) . .
N3 C8 N4 125.2(3) . .
N6 C8 N3 117.6(3) . .
N6 C8 N4 117.2(3) . .
N7 C9 C1 115.4(2) . .
N9 C9 C1 118.1(3) . .
N9 C9 N7 126.5(3) . .
N8 C10 N7 125.6(3) . .
N10 C10 N7 116.8(3) . .
N10 C10 N8 117.5(3) . .
N8 C11 N9 124.3(3) . .
N11 C11 N8 118.2(3) . .
N11 C11 N9 117.4(3) . .
C1 N1 C5 117.2(2) . .
C6 N2 C7 114.2(3) . .
C7 N3 C8 114.0(3) . .
C6 N4 C8 114.4(2) . .
C7 N5 H5A 120.0 . .
C7 N5 H5B 120.0 . .
H5A N5 H5B 120.0 . .
C8 N6 H6A 120.0 . .
C8 N6 H6B 120.0 . .
H6A N6 H6B 120.0 . .
C9 N7 C10 114.1(3) . .
C10 N8 C11 114.8(2) . .
C9 N9 C11 114.7(3) . .
C10 N10 H10A 120.0 . .
C10 N10 H10B 120.0 . .
H10A N10 H10B 120.0 . .
C11 N11 H11A 120.0 . .
C11 N11 H11B 120.0 . .
H11A N11 H11B 120.0 . .
O1 S1 C12 107.54(14) . .
O1 S1 C13 105.19(15) . .
C12 S1 C13 96.82(16) . .
S1 C12 H12A 109.5 . .
S1 C12 H12B 109.5 . .
S1 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
S1 C13 H13A 109.5 . .
S1 C13 H13B 109.5 . .
S1 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O2 S2 C14 106.7(3) . .
O2 S2 C15 104.4(3) . .
C14 S2 C15 100.1(4) . .
S2 C14 H14A 109.5 . .
S2 C14 H14B 109.5 . .
S2 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
S2 C15 H15A 109.5 . .
S2 C15 H15B 109.5 . .
S2 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C15B S2B C14B 101.4(6) . .
S2B C14B H14D 130.6 . .
S2B C14B H14E 98.2 . .
S2B C14B H14F 98.0 . .
H14D C14B H14E 109.5 . .
H14D C14B H14F 109.5 . .
H14E C14B H14F 109.5 . .
S2B C15B H15D 109.5 . .
S2B C15B H15E 109.5 . .
S2B C15B H15F 109.5 . .
H15D C15B H15E 109.5 . .
H15D C15B H15F 109.5 . .
H15E C15B H15F 109.5 . .
O3 O3 S3 49.60(15) 4_556 .
C17 S3 O3 90.7(2) . .
S3 C17 H17A 109.5 . .
S3 C17 H17B 109.5 . .
S3 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
H4A O4 H4A 110(6) . 4_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.394(4) .
C1 C9 1.505(4) .
C1 N1 1.345(4) .
C2 H2 0.9500 .
C2 C3 1.382(4) .
C3 H3 0.9500 .
C3 C4 1.380(4) .
C4 H4 0.9500 .
C4 C5 1.391(4) .
C5 C6 1.505(4) .
C5 N1 1.345(4) .
C6 N2 1.335(4) .
C6 N4 1.329(4) .
C7 N2 1.355(4) .
C7 N3 1.346(4) .
C7 N5 1.341(4) .
C8 N3 1.349(4) .
C8 N4 1.358(4) .
C8 N6 1.330(4) .
C9 N7 1.331(4) .
C9 N9 1.329(4) .
C10 N7 1.355(4) .
C10 N8 1.337(4) .
C10 N10 1.331(4) .
C11 N8 1.350(4) .
C11 N9 1.362(4) .
C11 N11 1.325(4) .
N5 H5A 0.8800 .
N5 H5B 0.8800 .
N6 H6A 0.8800 .
N6 H6B 0.8800 .
N10 H10A 0.8800 .
N10 H10B 0.8800 .
N11 H11A 0.8800 .
N11 H11B 0.8800 .
S1 O1 1.512(2) .
S1 C12 1.783(3) .
S1 C13 1.786(3) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
O2 S2 1.564(3) .
S2 C14 1.766(4) .
S2 C15 1.766(4) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
S2B C14B 1.765(4) .
S2B C15B 1.755(12) .
C14B H14D 0.9799 .
C14B H14E 0.9801 .
C14B H14F 0.9801 .
C15B H15D 0.9800 .
C15B H15E 0.9800 .
C15B H15F 0.9800 .
O3 O3 0.788(9) 4_556
O3 S3 1.906(4) .
S3 C17 1.765(4) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
O4 H4A 0.91(5) .
O4 H4A 0.91(5) 4_556
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
N5 H5A O3 0.88 2.07 2.909(7) 159.7 .
N5 H5A O3 0.88 2.28 3.123(7) 161.3 4_556
N5 H5B O1 0.88 2.16 3.008(3) 161.0 .
N6 H6A O2 0.88 2.20 2.851(4) 130.5 .
N6 H6B N8 0.88 2.11 2.987(3) 174.3 5_577
N10 H10A O2 0.88 2.20 3.077(3) 175.5 5_577
N10 H10B O2 0.88 2.16 3.027(3) 168.2 3_567
N11 H11A N4 0.88 2.11 2.945(3) 158.3 5_577
N11 H11B N9 0.88 2.05 2.914(4) 167.1 5_577
O4 H4A N3 0.91(5) 2.22(5) 3.100(3) 164(4) .
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
C1 C2 C3 C4 1.2(5) . . . .
C1 C9 N7 C10 179.1(3) . . . .
C1 C9 N9 C11 179.9(2) . . . .
C2 C1 C9 N7 8.5(4) . . . .
C2 C1 C9 N9 -171.6(3) . . . .
C2 C1 N1 C5 -0.1(4) . . . .
C2 C3 C4 C5 -0.4(5) . . . .
C3 C4 C5 C6 -179.9(3) . . . .
C3 C4 C5 N1 -0.7(5) . . . .
C4 C5 C6 N2 -13.5(4) . . . .
C4 C5 C6 N4 165.7(3) . . . .
C4 C5 N1 C1 0.9(5) . . . .
C5 C6 N2 C7 -179.2(3) . . . .
C5 C6 N4 C8 -178.3(3) . . . .
C6 C5 N1 C1 -179.9(3) . . . .
C9 C1 C2 C3 179.0(3) . . . .
C9 C1 N1 C5 180.0(3) . . . .
N1 C1 C2 C3 -1.0(5) . . . .
N1 C1 C9 N7 -171.6(3) . . . .
N1 C1 C9 N9 8.3(4) . . . .
N1 C5 C6 N2 167.3(3) . . . .
N1 C5 C6 N4 -13.4(4) . . . .
N2 C6 N4 C8 0.9(5) . . . .
N2 C7 N3 C8 -1.6(5) . . . .
N3 C7 N2 C6 -1.2(5) . . . .
N3 C8 N4 C6 -4.2(5) . . . .
N4 C6 N2 C7 1.6(5) . . . .
N4 C8 N3 C7 4.5(5) . . . .
N5 C7 N2 C6 178.5(3) . . . .
N5 C7 N3 C8 178.7(3) . . . .
N6 C8 N3 C7 -175.8(3) . . . .
N6 C8 N4 C6 176.1(3) . . . .
N7 C9 N9 C11 -0.3(4) . . . .
N7 C10 N8 C11 -0.9(5) . . . .
N8 C10 N7 C9 1.4(5) . . . .
N8 C11 N9 C9 0.9(4) . . . .
N9 C9 N7 C10 -0.8(4) . . . .
N9 C11 N8 C10 -0.4(4) . . . .
N10 C10 N7 C9 -178.0(3) . . . .
N10 C10 N8 C11 178.6(3) . . . .
N11 C11 N8 C10 -179.2(3) . . . .
N11 C11 N9 C9 179.8(3) . . . .

_cod_database_fobs_code 4517261
