#------------------------------------------------------------------------------
#$Date: 2022-01-01 07:13:54 +0200 (Sat, 01 Jan 2022) $
#$Revision: 271676 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/58/1565881.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_1565881
loop_
_publ_author_name
'Olejniczak, Anna'
'Katrusiak, Anna'
'Podsiadło, Marcin'
'Katrusiak, Andrzej'
_publ_section_title
;
 Stochastic hydration of a high-nitrogen-content molecular compound
 recrystallized under pressure
;
_journal_issue                   1
_journal_name_full               IUCrJ
_journal_page_first              49
_journal_page_last               54
_journal_paper_doi               10.1107/S2052252521010381
_journal_volume                  9
_journal_year                    2022
_chemical_formula_moiety         'C4 H2 Cl N5'
_chemical_formula_sum            'C4 H2 Cl N5'
_chemical_formula_weight         155.56
_chemical_name_systematic        6-chloro-1,2,3,4-tetrazolo[1,5-b]pyridazine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.005(2)
_cell_length_b                   8.7554(18)
_cell_length_c                   10.086(2)
_cell_measurement_reflns_used    859
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.4210
_cell_measurement_theta_min      3.5090
_cell_volume                     618.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      'diamond-anvil cell'
_diffrn_ambient_pressure         180000
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.717
_diffrn_measured_fraction_theta_max 0.640
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  φ    -35.00  19.75   0.75   20.00   0.00 -30.00   0.00    --    73
  2  φ    140.00 200.00   0.75   20.00   0.00 -30.00   0.00    --    80
  3  φ    160.00 217.00   0.75   20.00   0.00  30.00   0.00    --    76
  4  φ    -20.00  34.75   0.75   20.00   0.00  30.00   0.00    --    73
  5  ω    -24.00  24.00   0.75   20.00    --   30.00  39.46 -12.90   64
  6  ω    -24.00  24.00   0.75   20.00    --   30.00  39.46 167.10   64
  7  ω    -50.00  10.00   0.75   20.00    --  -30.00  39.46 167.10   80
  8  ω    -50.00  10.00   0.75   20.00    --  -30.00  39.46 -12.90   80
  9  ω    -64.00  -8.50   0.75   20.00    --  -30.00  81.40 -28.90   74
 10  ω    -64.00  -8.50   0.75   20.00    --  -30.00  81.40 151.10   74
 11  ω    -19.00   8.00   0.75   20.00    --   30.00  81.40 151.10   36
 12  ω    -19.00   8.00   0.75   20.00    --   30.00  81.40 -28.90   36
 13  ω    -43.00 -21.25   0.75   20.00    --   30.00 134.60 -56.90   29
 14  ω    -43.00 -21.25   0.75   20.00    --   30.00 134.60 123.10   29
 15  ω    -90.00 -36.00   0.75   20.00    --  -30.00 134.60 123.10   72
 16  ω    -90.00 -36.00   0.75   20.00    --  -30.00 134.60 -56.90   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'KM-4 CCD'
_diffrn_measurement_method
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0645556000
_diffrn_orient_matrix_UB_12      0.0522971000
_diffrn_orient_matrix_UB_13      -0.0296073000
_diffrn_orient_matrix_UB_21      0.0225911000
_diffrn_orient_matrix_UB_22      -0.0300225000
_diffrn_orient_matrix_UB_23      -0.0634375000
_diffrn_orient_matrix_UB_31      -0.0746344000
_diffrn_orient_matrix_UB_32      -0.0541494000
_diffrn_orient_matrix_UB_33      0.0066032000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3126
_diffrn_reflns_av_unetI/netI     0.1917
_diffrn_reflns_Laue_measured_fraction_full 0.717
_diffrn_reflns_Laue_measured_fraction_max 0.640
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3219
_diffrn_reflns_point_group_measured_fraction_full 0.723
_diffrn_reflns_point_group_measured_fraction_max 0.633
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.147
_diffrn_reflns_theta_min         3.081
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52021
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.2367
_refine_ls_R_factor_gt           0.1430
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3439
_refine_ls_wR_factor_ref         0.4295
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.734
_reflns_Friedel_fraction_max     0.624
_reflns_number_gt                410
_reflns_number_total             961
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lt5042.cif
_cod_data_source_block           C4H2N5Cl1@0_18GPa_phase_alpha_xH2O
_cod_original_cell_volume        618.6(3)
_cod_database_code               1565881
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C4H2N5Cl1
_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.
;
_reflns_odcompleteness_completeness 63.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.980
_oxdiff_exptl_absorpt_empirical_full_min 0.458
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Cl1 Cl 0.2916(10) 0.3335(6) 0.3239(6) 0.091(3) Uani 1 1 d . . . . .
N4 N 0.352(3) 0.749(2) 0.4127(13) 0.072(6) Uani 1 1 d . . . . .
N5 N 0.364(3) 0.5955(19) 0.4182(15) 0.082(6) Uani 1 1 d . . . . .
N3 N 0.421(3) 0.840(2) 0.5084(13) 0.089(6) Uani 1 1 d . . . . .
N2 N 0.380(3) 0.978(3) 0.4674(18) 0.086(6) Uani 1 1 d . . . . .
N1 N 0.295(3) 0.984(2) 0.3477(16) 0.076(5) Uani 1 1 d . . . . .
C9 C 0.274(3) 0.831(2) 0.3154(14) 0.057(5) Uani 1 1 d . . . . .
C7 C 0.207(4) 0.605(3) 0.2071(17) 0.074(6) Uani 1 1 d . . . . .
H7 H 0.164726 0.549814 0.134175 0.088 Uiso 1 1 calc R U . . .
C6 C 0.284(3) 0.5309(18) 0.3169(15) 0.053(4) Uani 1 1 d . . . . .
C8 C 0.195(4) 0.756(3) 0.2078(15) 0.072(6) Uani 1 1 d . . . . .
H8 H 0.136090 0.809662 0.139331 0.087 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
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
_geom_angle_publ_flag
N5 N4 N3 122.9(17) . . ?
C9 N4 N5 126.6(16) . . ?
C9 N4 N3 110.5(19) . . ?
C6 N5 N4 112.1(16) . . ?
N2 N3 N4 104.1(17) . . ?
N3 N2 N1 114.9(15) . . ?
N2 N1 C9 102.4(14) . . ?
N4 C9 N1 108.0(14) . . ?
N4 C9 C8 118.9(19) . . ?
C8 C9 N1 133.1(18) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C8 C7 C6 119.1(16) . . ?
N5 C6 Cl1 113.0(14) . . ?
N5 C6 C7 126.1(17) . . ?
C7 C6 Cl1 120.8(14) . . ?
C9 C8 H8 121.6 . . ?
C7 C8 C9 116.8(18) . . ?
C7 C8 H8 121.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C6 1.730(16) . ?
N4 N5 1.34(2) . ?
N4 N3 1.35(2) . ?
N4 C9 1.33(2) . ?
N5 C6 1.29(2) . ?
N3 N2 1.30(2) . ?
N2 N1 1.35(2) . ?
N1 C9 1.39(2) . ?
C9 C8 1.38(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.39(3) . ?
C7 C8 1.33(2) . ?
C8 H8 0.9300 . ?
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
_geom_torsion_publ_flag
N4 N5 C6 Cl1 -178.3(14) . . . . ?
N4 N5 C6 C7 5(3) . . . . ?
N4 N3 N2 N1 -3(3) . . . . ?
N4 C9 C8 C7 -2(4) . . . . ?
N5 N4 N3 N2 -179.5(17) . . . . ?
N5 N4 C9 N1 -178.8(19) . . . . ?
N5 N4 C9 C8 1(4) . . . . ?
N3 N4 N5 C6 179(2) . . . . ?
N3 N4 C9 N1 1(2) . . . . ?
N3 N4 C9 C8 -180(2) . . . . ?
N3 N2 N1 C9 3(2) . . . . ?
N2 N1 C9 N4 -2(2) . . . . ?
N2 N1 C9 C8 179(2) . . . . ?
N1 C9 C8 C7 177(2) . . . . ?
C9 N4 N5 C6 -2(3) . . . . ?
C9 N4 N3 N2 1(3) . . . . ?
C6 C7 C8 C9 5(4) . . . . ?
C8 C7 C6 Cl1 177(2) . . . . ?
C8 C7 C6 N5 -7(4) . . . . ?
