#------------------------------------------------------------------------------
#$Date: 2019-12-23 20:59:25 +0200 (Mon, 23 Dec 2019) $
#$Revision: 245514 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/72/4517255.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_4517255
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         'C12 H12 N10, H2 O'
_chemical_formula_sum            'C12 H14 N10 O'
_chemical_formula_weight         314.33
_chemical_name_common
;
6,6'-(1,2-phenylene)bis(1,3,5-triazine-2,4-diamine) monohydrate
;
_chemical_name_systematic
;
6,6'-(1,2-phenylene)bis(1,3,5-triazine-2,4-diamine) monohydrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                109.144(1)
_cell_angle_beta                 95.857(1)
_cell_angle_gamma                106.722(1)
_cell_formula_units_Z            2
_cell_length_a                   8.3259(2)
_cell_length_b                   9.6536(2)
_cell_length_c                   10.0614(2)
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.776
_cell_measurement_theta_min      4.146
_cell_volume                     714.21(3)
_computing_cell_refinement
;
SAINT (2013) V8.38A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.'
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.38A; 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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16790
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.745
_diffrn_reflns_theta_min         4.145
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1193 before and 0.0571 after correction. 
The Ratio of minimum to maximum transmission is 0.8260. 
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    1.462
_exptl_crystal_description       Block
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method H2O/EtOH
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0387
_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)+(0.0512P)²+0.2984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2871
_reflns_number_total             3272
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1_ada147.cif
_cod_data_source_block           ada147
_cod_database_code               4517255
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_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 0.24600(14) 0.43127(13) 0.83670(12) 0.0136(2) Uani 1 1 d . . . . .
N1 N 0.42317(13) 0.27797(11) 0.74684(10) 0.0141(2) Uani 1 1 d . . . . .
H5 H 0.149(2) 0.7144(19) 1.0692(18) 0.024(4) Uiso 1 1 d . . . . .
H6 H 0.257(2) 0.5098(18) 1.0557(18) 0.021(4) Uiso 1 1 d . . . . .
C2 C 0.19804(14) 0.45592(13) 0.71035(12) 0.0140(2) Uani 1 1 d . . . . .
N2 N 0.28542(13) 0.24527(12) 0.93626(11) 0.0157(2) Uani 1 1 d . . . . .
C3 C 0.13175(16) 0.57592(14) 0.71952(13) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.097(2) 0.591(2) 0.6288(19) 0.026(4) Uiso 1 1 d . . . . .
N3 N 0.45082(14) 0.08456(12) 0.84027(11) 0.0179(2) Uani 1 1 d . . . . .
C4 C 0.11352(16) 0.67083(15) 0.85043(14) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.066(2) 0.7514(19) 0.8540(17) 0.020(4) Uiso 1 1 d . . . . .
N4 N 0.58909(15) 0.12948(14) 0.66358(12) 0.0204(2) Uani 1 1 d . . . . .
H4A H 0.623(2) 0.050(2) 0.657(2) 0.035(5) Uiso 1 1 d . . . . .
H4B H 0.600(2) 0.170(2) 0.5933(19) 0.025(4) Uiso 1 1 d . . . . .
C5 C 0.16095(16) 0.64646(15) 0.97469(14) 0.0191(3) Uani 1 1 d . . . . .
N5 N 0.31904(16) 0.06410(14) 1.02715(13) 0.0223(3) Uani 1 1 d . . . . .
H5A H 0.372(3) -0.001(2) 1.038(2) 0.035(5) Uiso 1 1 d . . . . .
H5B H 0.263(3) 0.099(2) 1.095(2) 0.035(5) Uiso 1 1 d . . . . .
N6 N 0.12125(13) 0.20530(12) 0.51320(11) 0.0154(2) Uani 1 1 d . . . . .
C6 C 0.22561(15) 0.52747(14) 0.96758(13) 0.0167(3) Uani 1 1 d . . . . .
C7 C 0.32281(14) 0.31004(13) 0.83907(12) 0.0131(2) Uani 1 1 d . . . . .
N7 N 0.28148(13) 0.43900(12) 0.48706(11) 0.0155(2) Uani 1 1 d . . . . .
N8 N 0.18237(13) 0.19804(12) 0.28394(11) 0.0158(2) Uani 1 1 d . . . . .
C8 C 0.48450(15) 0.16335(14) 0.75194(13) 0.0156(2) Uani 1 1 d . . . . .
C9 C 0.35393(15) 0.13261(14) 0.93240(13) 0.0164(3) Uani 1 1 d . . . . .
N9 N 0.04033(15) -0.02577(13) 0.31648(12) 0.0216(2) Uani 1 1 d . . . . .
H9A H -0.009(2) -0.078(2) 0.3695(19) 0.028(4) Uiso 1 1 d . . . . .
H9B H 0.019(2) -0.074(2) 0.223(2) 0.031(4) Uiso 1 1 d . . . . .
C10 C 0.20386(14) 0.35859(14) 0.56196(12) 0.0139(2) Uani 1 1 d . . . . .
N10 N 0.34192(15) 0.42460(13) 0.26566(12) 0.0197(2) Uani 1 1 d . . . . .
H10A H 0.408(2) 0.523(2) 0.3028(18) 0.023(4) Uiso 1 1 d . . . . .
H10B H 0.328(2) 0.371(2) 0.171(2) 0.032(5) Uiso 1 1 d . . . . .
C11 C 0.11642(15) 0.12953(14) 0.37185(12) 0.0148(2) Uani 1 1 d . . . . .
C12 C 0.26779(15) 0.35179(14) 0.34683(13) 0.0148(2) Uani 1 1 d . . . . .
O1 O 0.42259(14) 0.77273(12) 0.58027(12) 0.0279(2) Uani 1 1 d . . . . .
H1A H 0.384(3) 0.675(3) 0.569(2) 0.051(6) Uiso 1 1 d . . . . .
H1B H 0.400(3) 0.821(3) 0.661(3) 0.048(6) 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 0.0140 0.0070 '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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0250 '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 C7 123.15(10) . .
C6 C1 C2 118.85(11) . .
C6 C1 C7 117.97(10) . .
C7 N1 C8 114.34(10) . .
C1 C2 C10 125.23(10) . .
C3 C2 C1 119.04(11) . .
C3 C2 C10 115.66(10) . .
C7 N2 C9 114.43(10) . .
C2 C3 H3 117.9(10) . .
C4 C3 C2 121.30(11) . .
C4 C3 H3 120.8(10) . .
C9 N3 C8 114.55(10) . .
C3 C4 H4 119.9(10) . .
C5 C4 C3 119.57(11) . .
C5 C4 H4 120.5(10) . .
H4A N4 H4B 118.9(16) . .
C8 N4 H4A 119.3(12) . .
C8 N4 H4B 119.6(11) . .
C4 C5 H5 120.1(9) . .
C4 C5 C6 119.96(11) . .
C6 C5 H5 120.0(9) . .
H5A N5 H5B 117.8(17) . .
C9 N5 H5A 120.2(12) . .
C9 N5 H5B 120.3(12) . .
C10 N6 C11 114.00(10) . .
C1 C6 H6 119.4(9) . .
C5 C6 C1 121.28(11) . .
C5 C6 H6 119.4(9) . .
N1 C7 C1 117.51(10) . .
N1 C7 N2 126.26(10) . .
N2 C7 C1 116.23(10) . .
C10 N7 C12 114.55(10) . .
C12 N8 C11 115.22(10) . .
N3 C8 N1 125.24(11) . .
N4 C8 N1 116.52(11) . .
N4 C8 N3 118.22(11) . .
N3 C9 N2 125.07(11) . .
N5 C9 N2 116.45(11) . .
N5 C9 N3 118.48(11) . .
H9A N9 H9B 118.7(17) . .
C11 N9 H9A 121.5(12) . .
C11 N9 H9B 118.4(12) . .
N6 C10 C2 118.38(10) . .
N6 C10 N7 126.44(11) . .
N7 C10 C2 114.92(10) . .
H10A N10 H10B 118.7(16) . .
C12 N10 H10A 121.6(11) . .
C12 N10 H10B 119.6(12) . .
N8 C11 N6 125.11(11) . .
N9 C11 N6 117.36(10) . .
N9 C11 N8 117.53(11) . .
N8 C12 N7 124.52(10) . .
N10 C12 N7 117.75(11) . .
N10 C12 N8 117.72(11) . .
H1A O1 H1B 105(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.4077(16) .
C1 C6 1.3998(16) .
C1 C7 1.4917(15) .
N1 C7 1.3319(15) .
N1 C8 1.3583(15) .
C2 C3 1.4011(16) .
C2 C10 1.4950(16) .
N2 C7 1.3398(14) .
N2 C9 1.3579(15) .
C3 H3 0.997(17) .
C3 C4 1.3880(18) .
N3 C8 1.3485(15) .
N3 C9 1.3457(16) .
C4 H4 0.963(16) .
C4 C5 1.3857(18) .
N4 H4A 0.88(2) .
N4 H4B 0.912(18) .
N4 C8 1.3367(16) .
C5 H5 0.997(17) .
C5 C6 1.3872(17) .
N5 H5A 0.89(2) .
N5 H5B 0.89(2) .
N5 C9 1.3380(16) .
N6 C10 1.3315(15) .
N6 C11 1.3596(15) .
C6 H6 0.980(16) .
N7 C10 1.3351(15) .
N7 C12 1.3584(15) .
N8 C11 1.3398(15) .
N8 C12 1.3394(16) .
N9 H9A 0.900(19) .
N9 H9B 0.875(19) .
N9 C11 1.3390(16) .
N10 H10A 0.875(19) .
N10 H10B 0.90(2) .
N10 C12 1.3310(15) .
O1 H1A 0.87(2) .
O1 H1B 0.86(2) .
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
N4 H4A O1 0.88(2) 2.52(2) 3.0996(15) 124.2(16) 1_545 yes
N4 H4B O1 0.912(18) 2.006(18) 2.9057(15) 168.6(16) 2_666 yes
N5 H5A N3 0.89(2) 2.30(2) 3.1348(15) 155.5(17) 2_657 yes
N5 H5B N8 0.89(2) 2.10(2) 2.9829(16) 167.8(18) 1_556 yes
N9 H9A N6 0.900(19) 2.072(19) 2.9709(15) 177.7(16) 2_556 yes
N9 H9B N2 0.875(19) 2.597(19) 3.1723(15) 124.1(15) 2_556 yes
N10 H10A N1 0.875(19) 2.268(18) 3.0233(14) 144.5(14) 2_666 yes
N10 H10B N2 0.90(2) 2.21(2) 3.1069(15) 176.9(17) 1_554 yes
O1 H1A N7 0.87(2) 2.03(2) 2.8731(15) 165(2) . 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 0.33(18) . . . .
C1 C2 C10 N6 54.69(16) . . . .
C1 C2 C10 N7 -130.72(12) . . . .
C2 C1 C6 C5 -0.59(18) . . . .
C2 C1 C7 N1 33.04(16) . . . .
C2 C1 C7 N2 -147.89(11) . . . .
C2 C3 C4 C5 -0.28(19) . . . .
C3 C2 C10 N6 -122.35(12) . . . .
C3 C2 C10 N7 52.24(14) . . . .
C3 C4 C5 C6 -0.22(19) . . . .
C4 C5 C6 C1 0.66(19) . . . .
C6 C1 C2 C3 0.10(17) . . . .
C6 C1 C2 C10 -176.85(11) . . . .
C6 C1 C7 N1 -145.10(11) . . . .
C6 C1 C7 N2 33.97(15) . . . .
C7 C1 C2 C3 -178.03(10) . . . .
C7 C1 C2 C10 5.02(18) . . . .
C7 C1 C6 C5 177.64(11) . . . .
C7 N1 C8 N3 0.11(17) . . . .
C7 N1 C8 N4 -178.52(11) . . . .
C7 N2 C9 N3 -0.56(17) . . . .
C7 N2 C9 N5 -179.64(11) . . . .
C8 N1 C7 C1 -178.13(10) . . . .
C8 N1 C7 N2 2.90(17) . . . .
C8 N3 C9 N2 3.08(18) . . . .
C8 N3 C9 N5 -177.86(11) . . . .
C9 N2 C7 C1 178.32(10) . . . .
C9 N2 C7 N1 -2.70(17) . . . .
C9 N3 C8 N1 -2.85(18) . . . .
C9 N3 C8 N4 175.77(11) . . . .
C10 C2 C3 C4 177.57(11) . . . .
C10 N6 C11 N8 -1.89(17) . . . .
C10 N6 C11 N9 177.84(11) . . . .
C10 N7 C12 N8 1.04(17) . . . .
C10 N7 C12 N10 179.85(10) . . . .
C11 N6 C10 C2 172.47(10) . . . .
C11 N6 C10 N7 -1.42(17) . . . .
C11 N8 C12 N7 -3.86(17) . . . .
C11 N8 C12 N10 177.33(11) . . . .
C12 N7 C10 C2 -172.26(10) . . . .
C12 N7 C10 N6 1.81(17) . . . .
C12 N8 C11 N6 4.33(17) . . . .
C12 N8 C11 N9 -175.40(11) . . . .

_cod_database_fobs_code 4517255
