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_7249002
_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 F8 N4, 0.5(C24 H18 B2 O4)'
_chemical_formula_sum            'C22 H9 B F8 N4 O2'
_chemical_formula_weight         524.14
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-04-10 deposited with the CCDC.	2024-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                81.392(13)
_cell_angle_beta                 77.890(15)
_cell_angle_gamma                85.140(16)
_cell_formula_units_Z            1
_cell_length_a                   6.2144(12)
_cell_length_b                   7.2948(13)
_cell_length_c                   11.7785(17)
_cell_measurement_reflns_used    2135
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      28.8290
_cell_measurement_theta_min      2.8290
_cell_volume                     515.40(16)
_computing_cell_refinement       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.112a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_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 0.987
_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     78.00 104.00   0.50   10.00    --   20.00  54.00-150.00   52
  2  \w      3.00  31.00   0.50   10.00    --   20.00  54.00  90.00   56
  3  \w     57.00 106.00   0.50   10.00    --   20.00  54.00  90.00   98
  4  \w    -74.00  26.00   0.50   10.00    --   20.00  54.00 -30.00  200
  5  \w     48.00  97.00   0.50   10.00    --   20.00  54.00 -30.00   98
  6  \w    -71.00 -11.00   0.50   10.00    --   20.00  54.00  30.00  120
  7  \w     40.00  65.00   0.50   10.00    --   20.00  54.00  30.00   50
  8  \w    -73.00  19.00   0.50   10.00    --   20.00  54.00 120.00  184
  9  \w     48.00  74.00   0.50   10.00    --   20.00  54.00 120.00   52
 10  \w    -52.00   1.00   0.50   10.00    --   20.00  54.00-120.00  106
 11  \w    -49.00  83.00   0.50   10.00    --   20.00  54.00-180.00  264
 12  \w    -74.00  56.00   0.50   10.00    --   20.00  54.00 -90.00  260
 13  \w    -47.00 -22.00   0.50   10.00    --   20.00  54.00   0.00   50
 14  \w    -73.00  58.00   0.50   10.00    --   20.00  54.00-150.00  262
;
_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      -0.0648184000
_diffrn_orient_matrix_UB_12      0.0129942000
_diffrn_orient_matrix_UB_13      -0.0437734000
_diffrn_orient_matrix_UB_21      0.0632167000
_diffrn_orient_matrix_UB_22      -0.0728167000
_diffrn_orient_matrix_UB_23      -0.0273601000
_diffrn_orient_matrix_UB_31      -0.0739669000
_diffrn_orient_matrix_UB_32      -0.0650334000
_diffrn_orient_matrix_UB_33      0.0346338000
_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  0.0498
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6510
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75262
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_description       prism
_exptl_crystal_F_000             262
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2083
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0795P)^2^+0.1487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1411
_reflns_number_total             2083
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00611a2.cif
_cod_data_source_block           PhBE-perFazop
_cod_depositor_comments
'Adding full bibliography for 7248998--7249003.cif.'
_cod_original_cell_volume        515.41(16)
_cod_database_code               7249002
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C H B N O F '
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.917
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 B1, O1, C6, C7, H7, C8, H8, C9, H9, C10, H10, C11, H11, O2, C12, C13, H13,
 C14, H14, C15, H15, C16, H16, C17
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Fixed Sof: O1(0.5) C6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5) H9(0.5)
 C10(0.5) H10(0.5) C11(0.5) H11(0.5) O2(0.5) C12(0.5) C17(0.5) C16(0.5)
 H16(0.5) C15(0.5) H15(0.5) C14(0.5) H14(0.5) C13(0.5) H13(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C15(H15), C14(H14),
 C13(H13)
4.b Fitted hexagon refined as free rotating group:
 C6(C7,C8,C9,C10,C11), C12(C17,C16,C15,C14,C13)
;
_shelx_res_checksum              94144
_shelx_hkl_checksum              71992
_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 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.848