Crystal design by CH···N and N···N interactions: high-pressure structures of high-nitrogen-content azido-triazolopyridazines compounds
Olejniczak, Anna; Katrusiak, Anna; Podsiadło, Marcin; Katrusiak, Andrzej; Acta Crystallographica Section B 76 (2020) –; doi:10.1107/S2052520620014493

data_2108719
_publ_section_title
;
 Crystal design by CH&#x00B7;&#x00B7;&#x00B7;N and
 N&#x00B7;&#x00B7;&#x00B7;N interactions: high-pressure structures of
 high-nitrogen-content azido-triazolopyridazines compounds
;
_journal_coeditor_code           DK5103SUP1
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520620014493
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C6 H5 N7, 0.6(O)'
_chemical_formula_sum            'C6 H5 N7 O0.6'
_chemical_formula_weight         184.77
_chemical_name_systematic
3-methyl-6-azido-1,2,4-triazolo[4,3-b]pyridazine
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   28.180(6)
_cell_length_b                   28.180(6)
_cell_length_c                   4.0701(17)
_cell_measurement_pressure       230000
_cell_measurement_reflns_used    419
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.5410
_cell_measurement_theta_min      4.2960
_cell_volume                     3232.1(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      'diamond-anvil cell'
_diffrn_ambient_pressure         230000
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.390
_diffrn_measured_fraction_theta_max 0.346
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \f    -35.00  19.75   0.75   37.00   0.00 -30.00   0.00    --    73
  2  \f    140.00 200.00   0.75   37.00   0.00 -30.00   0.00    --    80
  3  \f    160.00 217.00   0.75   37.00   0.00  30.00   0.00    --    76
  4  \f    -20.00  34.75   0.75   37.00   0.00  30.00   0.00    --    73
  5  \w    -24.00  24.00   0.75   37.00    --   30.00  39.46 -12.90   64
  6  \w    -24.00  24.00   0.75   37.00    --   30.00  39.46 167.10   64
  7  \w    -50.00  10.00   0.75   37.00    --  -30.00  39.46 167.10   80
  8  \w    -50.00  10.00   0.75   37.00    --  -30.00  39.46 -12.90   80
  9  \w    -64.00  -8.50   0.75   37.00    --  -30.00  81.40 -28.90   74
 10  \w    -64.00  -8.50   0.75   37.00    --  -30.00  81.40 151.10   74
 11  \w    -19.00   8.00   0.75   37.00    --   30.00  81.40 151.10   36
 12  \w    -19.00   8.00   0.75   37.00    --   30.00  81.40 -28.90   36
 13  \w    -43.00 -21.25   0.75   37.00    --   30.00 134.60 -56.90   29
 14  \w    -43.00 -21.25   0.75   37.00    --   30.00 134.60 123.10   29
 15  \w    -90.00 -36.00   0.75   37.00    --  -30.00 134.60 123.10   72
 16  \w    -90.00 -36.00   0.75   37.00    --  -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      0.0011373000
_diffrn_orient_matrix_UB_12      -0.0252113000
_diffrn_orient_matrix_UB_13      0.0021640000
_diffrn_orient_matrix_UB_21      0.0208582000
_diffrn_orient_matrix_UB_22      0.0011544000
_diffrn_orient_matrix_UB_23      0.0969624000
_diffrn_orient_matrix_UB_31      -0.0140325000
_diffrn_orient_matrix_UB_32      -0.0005216000
_diffrn_orient_matrix_UB_33      0.1442317000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2356
_diffrn_reflns_av_unetI/netI     0.1120
_diffrn_reflns_Laue_measured_fraction_full 0.390
_diffrn_reflns_Laue_measured_fraction_max 0.346
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6161
_diffrn_reflns_point_group_measured_fraction_full 0.390
_diffrn_reflns_point_group_measured_fraction_max 0.346
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.010
_diffrn_reflns_theta_min         4.339
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58525
_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    1.519
_exptl_crystal_description       plate
_exptl_crystal_F_000             1517
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1858
_refine_ls_R_factor_gt           0.0827
_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/[\s^2^(Fo^2^)+(0.1072P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1868
_refine_ls_wR_factor_ref         0.2340
_reflns_Friedel_coverage         0.000
_reflns_number_gt                296
_reflns_number_total             614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dk5103sup1.cif
_cod_data_source_block           C6H5N7.H2Oat0_23GPa
_cod_original_cell_volume        3232.2(19)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_original_formula_sum        'C6 H5 N7 O0.60'
_cod_database_code               2108719
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C6H5N7O1
_reflns_odcompleteness_completeness 33.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O1(0.6)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_shelx_res_checksum              37314
_shelx_hkl_checksum              33197
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.603
_oxdiff_exptl_absorpt_empirical_full_min 0.321