#------------------------------------------------------------------------------
#$Date: 2020-03-04 08:02:24 +0200 (Wed, 04 Mar 2020) $
#$Revision: 248729 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243303.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243303
loop_
_publ_author_name
'Khotchasanthong, Kenika'
'Jittirattanakun, Siripak'
'Chainok, Kittipong'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 3,6-bis(pyrimidin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine dihydrate
;
_journal_coeditor_code           HB7895
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              473
_journal_page_last               476
_journal_paper_doi               10.1107/S2056989020002765
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C10 H8 N8, 2H2 O'
_chemical_formula_moiety         'C10 H8 N8, 2(H2 O)'
_chemical_formula_sum            'C10 H12 N8 O2'
_chemical_formula_weight         276.28
_chemical_name_systematic
;
3,6-Bis(pyrimidin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine dihydrate
;
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.687(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.4730(12)
_cell_length_b                   3.7262(2)
_cell_length_c                   13.9102(7)
_cell_measurement_reflns_used    4681
_cell_measurement_temperature    296.0
_cell_measurement_theta_max      28.073
_cell_measurement_theta_min      3.269
_cell_volume                     1210.67(11)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 200 area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11339
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.305
_diffrn_reflns_theta_min         2.943
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.386
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1487
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0533
_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)+(0.1061P)²+0.7279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.1739
_reflns_number_gt                1145
_reflns_number_total             1487
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7895sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243303
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.21290(11) 0.4286(11) 0.71824(16) 0.1166(10) Uani d 1 . .
H H1A 0.2318(9) 0.594(5) 0.7537(16) 0.060(8) Uiso d 1 . .
H H1B 0.1796(10) 0.400(13) 0.738(3) 0.19(2) Uiso d 1 . .
N N1 0.14093(6) 0.2128(5) 0.86243(11) 0.0426(4) Uani d 1 . .
N N2 0.07173(6) 0.2495(4) 0.97609(10) 0.0386(4) Uani d 1 . .
N N3 0.05508(6) 0.4046(4) 0.72282(9) 0.0372(4) Uani d 1 . .
N N4 -0.00726(6) 0.5326(4) 0.83844(9) 0.0381(4) Uani d 1 . .
H H4 -0.0111(9) 0.481(6) 0.8970(8) 0.052(6) Uiso d 1 . .
C C1 0.17826(8) 0.0798(6) 0.93187(14) 0.0488(5) Uani d 1 . .
H H1 0.215005 0.024291 0.916985 0.059 Uiso calc 1 . .
C C2 0.16473(8) 0.0213(5) 1.02458(14) 0.0468(5) Uani d 1 . .
H H2 0.190969 -0.077223 1.071768 0.056 Uiso calc 1 . .
C C3 0.11048(8) 0.1160(5) 1.04382(13) 0.0441(5) Uani d 1 . .
H H3 0.100261 0.086189 1.106236 0.053 Uiso calc 1 . .
C C4 0.08877(6) 0.2840(4) 0.88786(11) 0.0327(4) Uani d 1 . .
C C5 0.04524(7) 0.4139(4) 0.81150(11) 0.0323(4) Uani d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
H1A O1 H1B . . 109(2) ?
C1 N1 C4 . . 115.86(15) ?
C4 N2 C3 . . 116.00(15) ?
C5 N3 N4 . 2_556 111.21(13) ?
N3 N4 H4 2_556 . 110.2(15) ?
C5 N4 N3 . 2_556 113.47(13) ?
C5 N4 H4 . . 111.5(15) ?
N1 C1 H1 . . 118.6 ?
N1 C1 C2 . . 122.79(17) ?
C2 C1 H1 . . 118.6 ?
C1 C2 H2 . . 121.7 ?
C3 C2 C1 . . 116.54(16) ?
C3 C2 H2 . . 121.7 ?
N2 C3 C2 . . 122.46(16) ?
N2 C3 H3 . . 118.8 ?
C2 C3 H3 . . 118.8 ?
N1 C4 C5 . . 117.46(14) ?
N2 C4 N1 . . 126.25(15) ?
N2 C4 C5 . . 116.30(14) ?
N3 C5 N4 . . 121.13(14) ?
N3 C5 C4 . . 120.39(14) ?
N4 C5 C4 . . 118.44(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 H1A . 0.882(10) ?
O1 H1B . 0.860(10) ?
N1 C1 . 1.334(2) ?
N1 C4 . 1.334(2) ?
N2 C3 . 1.339(2) ?
N2 C4 . 1.334(2) ?
N3 N4 2_556 1.423(2) ?
N3 C5 . 1.278(2) ?
N4 H4 . 0.851(9) ?
N4 C5 . 1.395(2) ?
C1 H1 . 0.9300 ?
C1 C2 . 1.376(3) ?
C2 H2 . 0.9300 ?
C2 C3 . 1.373(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.480(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1A O1 4_556 0.880(10) 1.810(10) 2.642(4) 156(2) yes
O1 H1B N1 . 0.860(10) 2.15(4) 2.863(3) 140(5) yes
N4 H4 N2 5_567 0.850(10) 2.570(10) 3.2210(10) 133(2) yes
C2 H2 O1 6_556 0.93 2.43 3.278(3) 151 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . -1.6(3) ?
N1 C4 C5 N3 . . . . 10.4(3) ?
N1 C4 C5 N4 . . . . -172.09(16) ?
N2 C4 C5 N3 . . . . -169.62(15) ?
N2 C4 C5 N4 . . . . 7.9(2) ?
N3 N4 C5 N3 2_556 . . . 41.7(2) ?
N3 N4 C5 C4 2_556 . . . -135.76(15) ?
N4 N3 C5 N4 2_556 . . . 1.0(2) ?
N4 N3 C5 C4 2_556 . . . 178.46(14) ?
C1 N1 C4 N2 . . . . 3.1(3) ?
C1 N1 C4 C5 . . . . -176.87(15) ?
C1 C2 C3 N2 . . . . 1.8(3) ?
C3 N2 C4 N1 . . . . -3.0(3) ?
C3 N2 C4 C5 . . . . 176.97(15) ?
C4 N1 C1 C2 . . . . -0.6(3) ?
C4 N2 C3 C2 . . . . 0.4(3) ?

_cod_database_fobs_code 2243303
