Noncovalent synergistic-directed crystallization (NSDC): a halogen engineering strategy for multifunctional energetic crystals
Li, Cong; Lu, Zu-jia; Zhang, Chao; Xu, Mei-qi; Zhao, Bin-shan; Yu, Qi-yao; Zhang, Jian-guo; CrystEngComm 27 (2025) 5346–5355; doi:10.1039/D5CE00606F

data_7250685
_publ_section_title
;
 Noncovalent synergistic-directed crystallization (NSDC): a halogen
 engineering strategy for multifunctional energetic crystals
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              5346
_journal_page_last               5355
_journal_paper_doi               10.1039/D5CE00606F
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C8 H6 F2 N4 O2'
_chemical_formula_sum            'C8 H6 F2 N4 O2'
_chemical_formula_weight         228.17
_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             2025-02-23
_audit_creation_method
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_audit_update_record
;
2025-06-11 deposited with the CCDC.	2025-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.490(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8400(3)
_cell_length_b                   18.3788(8)
_cell_length_c                   7.3602(4)
_cell_measurement_reflns_used    3219
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.3770
_cell_measurement_theta_min      4.7660
_cell_volume                     912.60(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.127a 64-bit (release 16-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.972
_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    -57.00 -17.00   0.50    0.05    --  -97.00  50.00  60.00   80
  2  \w    -45.00 -16.00   0.50    0.05    --  -97.00  38.00   0.00   58
  3  \w    -42.00 -16.00   0.50    0.05    --  -97.00  38.00 -30.00   52
  4  \w    -43.00 -18.00   0.50    0.05    --  -97.00  38.00 -60.00   50
  5  \w    -44.00 -14.00   0.50    0.05    --  -97.00  38.00-150.00   60
  6  \w    -46.00 -20.00   0.50    0.05    --  -97.00  38.00-180.00   52
  7  \w    -46.00 -21.00   0.50    0.05    --  -97.00  38.00-120.00   50
  8  \w    -15.00  22.00   0.50    0.05    --  -56.47  15.00-150.00   74
  9  \w    -26.00  25.00   0.50    0.05    --  -56.47  15.00 -30.00  102
 10  \w    -33.00  13.00   0.50    0.05    --  -56.47  30.00  90.00   92
 11  \w    -43.00 -18.00   0.50    0.05    --  -97.00  38.00 120.00   50
 12  \w    -45.00 -19.00   0.50    0.05    --  -97.00  38.00 150.00   52
 13  \w   -103.00 -50.00   0.50    0.05    --  -56.47 101.00 122.00  106
 14  \w   -121.00 -95.00   0.50    0.05    --  -56.47-101.00  18.00   52
 15  \w   -155.00-124.00   0.50    0.05    --  -56.47-101.00  18.00   62
 16  \w   -157.00-132.00   0.50    0.05    --  -97.00-101.00  18.00   50
 17  \w   -129.00-103.00   0.50    0.05    --  -97.00-104.00 150.00   52
 18  \w   -174.00-130.00   0.50    0.05    --  -97.00-104.00 150.00   88
 19  \w   -101.00 -51.00   0.50    0.05    --  -97.00 101.00 122.00  100
 20  \w    -45.00  20.00   0.50    0.05    --   56.47 -15.00  60.00  130
 21  \w     17.00  64.00   0.50    0.05    --  112.93 -64.00  60.00   94
 22  \w     45.00  70.00   0.50    0.05    --  112.93 -64.00  30.00   50
 23  \w     25.00  50.00   0.50    0.05    --  112.93 -50.00   0.00   50
 24  \w     16.00  72.00   0.50    0.05    --  112.93 -64.00 -30.00  112
 25  \w     29.00  70.00   0.50    0.05    --  112.93 -64.00-120.00   82
 26  \w     14.00  64.00   0.50    0.05    --  112.93 -64.00-150.00  100
 27  \w     15.00  40.00   0.50    0.05    --  112.93 -64.00-180.00   50
 28  \w     19.00  44.00   0.50    0.05    --  112.93 -50.00-180.00   50
 29  \w     20.00  46.00   0.50    0.05    --  112.93 -50.00-150.00   52
 30  \w     27.00  54.00   0.50    0.05    --  112.93 -50.00 -90.00   54
 31  \w     19.00  44.00   0.50    0.05    --  112.93 -50.00 -60.00   50
 32  \w     26.00  52.00   0.50    0.05    --  112.93 -50.00  60.00   52
 33  \w     21.00  47.00   0.50    0.05    --  112.93 -50.00  90.00   52
 34  \w     20.00  46.00   0.50    0.05    --  112.93 -92.00  60.00   52
 35  \w     17.00  42.00   0.50    0.05    --   56.47-101.00  18.00   50
 36  \w     52.00  89.00   0.50    0.05    --  112.93-101.00  18.00   74
 37  \w     53.00  99.00   0.50    0.05    --  112.93 -92.00  60.00   92
 38  \w     46.00  98.00   0.50    0.05    --  112.93-104.00 150.00  104
 39  \w      4.00  29.00   0.50    0.05    --    0.00-101.00  18.00   50
 40  \w     18.00  79.00   0.50    0.05    --    0.00  19.00   0.00  122
 41  \w     97.00 124.00   0.50    0.05    --   56.47 101.00 122.00   54
 42  \w     90.00 124.00   0.50    0.05    --  112.93 101.00 122.00   68
 43  \w     79.00 127.00   0.50    0.05    --   56.47 125.00  60.00   96
 44  \w    -29.00  -4.00   0.50    0.05    --    0.00  19.00   0.00   50
 45  \w    -55.00 -30.00   0.50    0.05    --    0.00 101.00 122.00   50
 46  \w   -105.00 -78.00   0.50    0.05    --    0.00 179.00  90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0594027000
_diffrn_orient_matrix_UB_12      0.0258513000
_diffrn_orient_matrix_UB_13      0.2007086000
_diffrn_orient_matrix_UB_21      -0.0891158000
_diffrn_orient_matrix_UB_22      0.0754344000
_diffrn_orient_matrix_UB_23      -0.0540357000
_diffrn_orient_matrix_UB_31      -0.2016563000
_diffrn_orient_matrix_UB_32      -0.0257199000
_diffrn_orient_matrix_UB_33      0.0433536000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4179
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.513
_diffrn_reflns_theta_min         4.812
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.323
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0551P)^2^+0.4172P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1541
_reflns_number_total             1696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00606f2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7250684--7250685.cif.'
_cod_database_code               7250685
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         chonf
_shelx_estimated_absorpt_t_max   0.868
_shelx_estimated_absorpt_t_min   0.778
_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.a Ternary CH refined with riding coordinates:
 C00F(H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              38208
_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 2.728
_oxdiff_exptl_absorpt_empirical_full_min 0.680