Co-crystal formation vs. boron coordination: fluorination in azopyridines regulates supramolecular competition
Loya, Jesus Daniel; Agarwal, Sidhaesh A.; Lutz, Nicholas; Reinheimer, Eric W.; Campillo-Alvarado, Gonzalo; CrystEngComm 26 (2024) 4017–4021; doi:10.1039/D4CE00611A

data_7249000
_publ_section_title
;
 Co-crystal formation vs. boron coordination: fluorination in azopyridines
 regulates supramolecular competition
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              4017
_journal_page_last               4021
_journal_paper_doi               10.1039/D4CE00611A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C10 H4 F4 N4'
_chemical_formula_sum            'C10 H4 F4 N4'
_chemical_formula_weight         256.17
_chemical_name_systematic        3,5-difluoroazopyridine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-11
_audit_creation_method
;
Olex2 1.5-ac6-017
(compiled 2024.02.01 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_audit_update_record
;
2024-04-10 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.109(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0686(6)
_cell_length_b                   5.1891(7)
_cell_length_c                   18.590(2)
_cell_measurement_reflns_used    1215
_cell_measurement_temperature    99.9(7)
_cell_measurement_theta_max      29.4790
_cell_measurement_theta_min      2.1540
_cell_volume                     488.94(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.108a 64-bit (release 14-02-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-017 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     29.00  69.00   0.50    5.00    --   20.00  54.00   0.00   80
  2  \w    -73.00 -39.00   0.50    5.00    --   20.00  54.00 120.00   68
  3  \w    -26.00  88.00   0.50    5.00    --   20.00  54.00 120.00  228
  4  \w    -74.00 -38.00   0.50    5.00    --   20.00  54.00-180.00   72
  5  \w    -22.00  26.00   0.50    5.00    --   20.00  54.00-180.00   96
  6  \w     70.00  98.00   0.50    5.00    --   20.00  54.00-180.00   56
  7  \w    -74.00 -43.00   0.50    5.00    --   20.00  54.00 -30.00   62
  8  \w    -37.00 -11.00   0.50    5.00    --   20.00  54.00 -30.00   52
  9  \w     82.00 107.00   0.50    5.00    --   20.00  54.00 -30.00   50
 10  \w    -63.00 -36.00   0.50    5.00    --   20.00  54.00   0.00   54
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0048188000
_diffrn_orient_matrix_UB_12      0.1343295000
_diffrn_orient_matrix_UB_13      -0.0069335000
_diffrn_orient_matrix_UB_21      0.0613137000
_diffrn_orient_matrix_UB_22      0.0244320000
_diffrn_orient_matrix_UB_23      0.0336610000
_diffrn_orient_matrix_UB_31      0.1258038000
_diffrn_orient_matrix_UB_32      -0.0069612000
_diffrn_orient_matrix_UB_33      -0.0165000000
_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  0.0390
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            2309
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.191
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.112a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.019(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0772P)^2^+0.0289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.000
_reflns_number_gt                705
_reflns_number_total             848
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00611a2.cif
_cod_data_source_block           tetraFazop
_cod_depositor_comments
'Adding full bibliography for 7248998--7249003.cif.'
_cod_original_cell_volume        488.96(11)
_cod_database_code               7249000
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C5 H2 F2 N2'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1)
;
_shelx_res_checksum              94889
_shelx_hkl_checksum              91274
_olex2_submission_original_sample_id 3,5Fazop
_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 2.088
_oxdiff_exptl_absorpt_empirical_full_min 0.686