#------------------------------------------------------------------------------
#$Date: 2021-01-02 03:34:32 +0200 (Sat, 02 Jan 2021) $
#$Revision: 260350 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/98/1559897.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_1559897
loop_
_publ_author_name
'Khadivjam, Tinasadat'
'Che-Quang, Huy'
'Maris, Thierry'
'Ajoyan, Zvart'
'Howarth, Ashlee J.'
'Wuest, James D.'
_publ_section_title
;
 Modular Construction of Porous Hydrogen-Bonded Molecular Materials from
 Melams
;
_journal_issue                   31
_journal_name_full               'Chemistry-A European Journal'
_journal_page_first              7026
_journal_page_last               7040
_journal_paper_doi               10.1002/chem.202000186
_journal_volume                  26
_journal_year                    2020
_chemical_formula_moiety         'C12 H13 N11, 3(C2 H6 O S)'
_chemical_formula_sum            'C18 H31 N11 O3 S3'
_chemical_formula_weight         545.72
_chemical_name_systematic
;
N2-(4,6-diamino-1,3,5-triazin-2-yl)
-N2-phenyl-1,3,5-triazine-2,4,6-triamine dimethyl sulfoxide solvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.486(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9174(4)
_cell_length_b                   18.9758(8)
_cell_length_c                   13.2699(5)
_cell_measurement_reflns_used    9627
_cell_measurement_temperature    200
_cell_measurement_theta_max      72.058
_cell_measurement_theta_min      4.660
_cell_volume                     2743.99(18)
_computing_cell_refinement
;
SAINT (2006) V7.34A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.'
;
_computing_data_collection
;
APEX 2 (2006) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2006) V7.34A; 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)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD Area detector'
_diffrn_detector_area_resol_mean 5.5
_diffrn_detector_type            'Bruker Smart 6K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Montel Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17420
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.360
_diffrn_reflns_theta_min         4.660
_diffrn_source                   'Rotating Anode'
_diffrn_source_target            Cu
_diffrn_source_type              'FR591 Rotating Anode'
_exptl_absorpt_coefficient_mu    2.823
_exptl_absorpt_correction_T_max  0.7058
_exptl_absorpt_correction_T_min  0.5072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2007/4 (Bruker,2007/4) was used for absorption correction. 
wR2(int) was 0.1675 before and 0.0631 after correction. 
The Ratio of minimum to maximum transmission is 0.7186. 
The λ/2 correction factor is Not present.'
;
_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    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2709
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0965P)²+2.9785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2489
_reflns_number_total             2709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            melam_5-3_dmso_jw1392.cif
_cod_data_source_block           jw1392
_cod_database_code               1559897
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 '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_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 0.500000 -0.1715(2) 0.250000 0.120(3) Uani 1 2 d S T P . .
H1 H 0.499998 -0.221532 0.249999 0.144 Uiso 1 2 calc RS T P . .
C2 C 0.5071(3) -0.13547(19) 0.3396(4) 0.0976(15) Uani 1 1 d . . . . .
H2 H 0.512578 -0.160701 0.401562 0.117 Uiso 1 1 calc R . . . .
C3 C 0.5063(2) -0.06255(15) 0.3404(2) 0.0567(7) Uani 1 1 d . . . . .
H3 H 0.510072 -0.037708 0.402711 0.068 Uiso 1 1 calc R . . . .
C4 C 0.500000 -0.02601(15) 0.250000 0.0357(6) Uani 1 2 d S T P . .
C5 C 0.41578(18) 0.08664(10) 0.18576(15) 0.0341(4) Uani 1 1 d . . . . .
C6 C 0.37547(18) 0.18122(12) 0.08777(16) 0.0384(5) Uani 1 1 d . . . . .
C7 C 0.22593(18) 0.10188(11) 0.11570(16) 0.0373(5) Uani 1 1 d . . . . .
N1 N 0.500000 0.04882(13) 0.250000 0.0363(5) Uani 1 2 d S T P . .
N2 N 0.30290(15) 0.06088(9) 0.17432(13) 0.0367(4) Uani 1 1 d . . . . .
N3 N 0.25684(16) 0.16251(10) 0.07156(14) 0.0398(4) Uani 1 1 d . . . . .
N4 N 0.46077(15) 0.14408(10) 0.14365(14) 0.0379(4) Uani 1 1 d . . . . .
N5 N 0.10915(16) 0.08073(11) 0.10298(16) 0.0487(5) Uani 1 1 d . . . . .
H5A H 0.055609 0.106285 0.066708 0.058 Uiso 1 1 calc R . . . .
H5B H 0.085866 0.041249 0.130887 0.058 Uiso 1 1 calc R . . . .
N6 N 0.41180(17) 0.24084(11) 0.04523(16) 0.0509(5) Uani 1 1 d . . . . .
H6A H 0.358907 0.266315 0.008176 0.061 Uiso 1 1 calc R . . . .
H6B H 0.488631 0.254647 0.054243 0.061 Uiso 1 1 calc R . . . .
S1 S 0.72957(5) 0.34342(3) -0.03444(4) 0.0447(2) Uani 1 1 d . . . . .
O1 O 0.60131(16) 0.33609(10) 0.00025(15) 0.0575(5) Uani 1 1 d . . . . .
C8 C 0.7466(3) 0.43410(14) -0.0661(2) 0.0596(7) Uani 1 1 d . . . . .
H8A H 0.828961 0.442047 -0.089374 0.089 Uiso 1 1 calc R . . . .
H8B H 0.685129 0.446848 -0.119934 0.089 Uiso 1 1 calc R . . . .
H8C H 0.735027 0.463230 -0.006459 0.089 Uiso 1 1 calc R . . . .
C9 C 0.7274(2) 0.30728(14) -0.15797(19) 0.0535(6) Uani 1 1 d . . . . .
H9A H 0.809387 0.310927 -0.183726 0.080 Uiso 1 1 calc R . . . .
H9B H 0.703002 0.257623 -0.155855 0.080 Uiso 1 1 calc R . . . .
H9C H 0.668535 0.333344 -0.202505 0.080 Uiso 1 1 calc R . . . .
O2 O 0.0074(19) -0.01099(17) 0.257(2) 0.063(3) Uani 0.5 1 d D . . A -1
S2 S 0.02917(17) -0.08376(7) 0.30632(10) 0.0679(5) Uani 0.5 1 d D . . A -1
C10 C 0.1661(9) -0.1145(4) 0.2568(8) 0.098(3) Uani 0.5 1 d D . . A -1
H10A H 0.186565 -0.161030 0.285031 0.147 Uiso 0.5 1 calc R . . A -1
H10B H 0.154636 -0.117943 0.183132 0.147 Uiso 0.5 1 calc R . . A -1
H10C H 0.232976 -0.081504 0.274745 0.147 Uiso 0.5 1 calc R . . A -1
C11 C -0.0757(10) -0.1405(5) 0.2421(6) 0.094(3) Uani 0.5 1 d D . . A -1
H11A H -0.066671 -0.188130 0.270270 0.142 Uiso 0.5 1 calc R . . A -1
H11B H -0.159422 -0.123672 0.249931 0.142 Uiso 0.5 1 calc R . . A -1
H11C H -0.059536 -0.141524 0.170288 0.142 Uiso 0.5 1 calc R . . A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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 C2 120.2(4) . 2_655
C1 C2 C3 120.4(4) . .
C2 C3 C4 119.6(3) . .
C3 C4 C3 119.9(3) . 2_655
C3 C4 N1 120.06(17) 2_655 .
C3 C4 N1 120.06(17) . .
N2 C5 N1 116.65(17) . .
N2 C5 N4 128.13(18) . .
N4 C5 N1 115.22(17) . .
N3 C6 N4 124.96(19) . .
N6 C6 N3 117.59(19) . .
N6 C6 N4 117.45(18) . .
N3 C7 N2 125.34(18) . .
N5 C7 N2 116.94(19) . .
N5 C7 N3 117.70(19) . .
C5 N1 C4 120.57(11) . .
C5 N1 C4 120.56(11) 2_655 .
C5 N1 C5 118.9(2) 2_655 .
C5 N2 C7 113.18(17) . .
C7 N3 C6 114.88(17) . .
C5 N4 C6 113.40(17) . .
O1 S1 C8 105.85(12) . .
O1 S1 C9 106.60(12) . .
C9 S1 C8 98.67(13) . .
O2 S2 C10 104.3(9) . .
O2 S2 C11 105.2(10) . .
C11 S2 C10 99.1(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.370(5) .
C1 C2 1.370(5) 2_655
C2 C3 1.384(5) .
C3 C4 1.384(3) .
C4 N1 1.420(4) .
C5 N1 1.411(2) .
C5 N2 1.326(3) .
C5 N4 1.332(3) .
C6 N3 1.348(3) .
C6 N4 1.353(3) .
C6 N6 1.335(3) .
C7 N2 1.355(3) .
C7 N3 1.343(3) .
C7 N5 1.337(3) .
S1 O1 1.5068(17) .
S1 C8 1.784(3) .
S1 C9 1.776(3) .
O2 S2 1.543(16) .
S2 C10 1.768(9) .
S2 C11 1.755(7) .
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
_geom_hbond_publ_flag
N5 H5A O1 0.88 2.18 3.044(3) 168.7 7 yes
N5 H5B O2 0.88 2.16 2.95(2) 148.6 . yes
N5 H5B O2 0.88 2.11 2.90(2) 149.7 2 yes
N6 H6A N3 0.88 2.09 2.968(3) 173.1 7 yes
N6 H6B O1 0.88 2.13 2.838(3) 137.5 . yes
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 -0.9(4) . . . .
C2 C1 C2 C3 0.4(2) 2_655 . . .
C2 C3 C4 C3 0.4(2) . . . 2_655
C2 C3 C4 N1 -179.6(2) . . . .
C3 C4 N1 C5 45.76(15) . . . 2_655
C3 C4 N1 C5 -134.24(15) . . . .
C3 C4 N1 C5 -134.24(15) 2_655 . . 2_655
C3 C4 N1 C5 45.76(15) 2_655 . . .
N1 C5 N2 C7 176.90(17) . . . .
N1 C5 N4 C6 -176.08(17) . . . .
N2 C5 N1 C4 39.1(2) . . . .
N2 C5 N1 C5 -140.9(2) . . . 2_655
N2 C5 N4 C6 4.3(3) . . . .
N2 C7 N3 C6 1.1(3) . . . .
N3 C6 N4 C5 -2.2(3) . . . .
N3 C7 N2 C5 0.5(3) . . . .
N4 C5 N1 C4 -140.54(14) . . . .
N4 C5 N1 C5 39.46(14) . . . 2_655
N4 C5 N2 C7 -3.5(3) . . . .
N4 C6 N3 C7 -0.2(3) . . . .
N5 C7 N2 C5 -177.9(2) . . . .
N5 C7 N3 C6 179.5(2) . . . .
N6 C6 N3 C7 179.6(2) . . . .
N6 C6 N4 C5 178.0(2) . . . .
