BOPAHY: a doubly chelated highly fluorescent pyrrole-acyl hydrazone -BF<sub>2</sub> chromophore.
Pookkandam Parambil, Shandev; de Jong, Flip; Veys, Koen; Huang, Jianjun; Veettil, Santhini Pulikkal; Verhaeghe, Davy; Van Meervelt, Luc; Escudero, Daniel; Van der Auweraer, Mark; Dehaen, Wim; Chemical communications (Cambridge, England) 56 (2020) 5791–5794; doi:10.1039/d0cc01131b

data_7126359
_publ_section_title
;
 BOPAHY: a doubly chelated highly fluorescent pyrrole-acyl hydrazone
 -BF<sub>2</sub> chromophore.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5791
_journal_page_last               5794
_journal_paper_doi               10.1039/d0cc01131b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C12 H12 B2 F4 N4 O'
_chemical_formula_sum            'C12 H12 B2 F4 N4 O'
_chemical_formula_weight         325.88
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-07 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.221(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2475(6)
_cell_length_b                   4.8212(2)
_cell_length_c                   15.1310(8)
_cell_measurement_reflns_used    4111
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8540
_cell_measurement_theta_min      2.8950
_cell_volume                     705.88(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     35.00  95.00   1.00   10.00    --   18.87 178.00  30.00   60
  2  \w     -7.00  91.00   1.00   10.00    --   18.87  38.00-180.00   98
  3  \w    -54.00  44.00   1.00   10.00    --   18.87 -38.00   0.00   98
  4  \w    -61.00  56.00   1.00   10.00    --  -17.07  19.00-150.00  117
  5  \w    -20.00  25.00   1.00   10.00    --  -17.07 -99.00   0.00   45
  6  \w    -50.00  40.00   1.00   10.00    --   18.87 -57.00-150.00   90
  7  \w     -3.00  68.00   1.00   10.00    --   18.87  57.00 -60.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0671986000
_diffrn_orient_matrix_UB_12      0.0558634000
_diffrn_orient_matrix_UB_13      -0.0208784000
_diffrn_orient_matrix_UB_21      0.0020121000
_diffrn_orient_matrix_UB_22      -0.0372572000
_diffrn_orient_matrix_UB_23      -0.0448803000
_diffrn_orient_matrix_UB_31      -0.0293316000
_diffrn_orient_matrix_UB_32      -0.1307724000
_diffrn_orient_matrix_UB_33      0.0038893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8064
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.851
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'greenish yellow'
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0291P)^2^+0.1824P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2551
_reflns_number_total             2850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01131b2.cif
_cod_data_source_block           wdh1094
_cod_depositor_comments
'Adding full bibliography for 7126359--7126362.cif.'
_cod_database_code               7126359
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C12 H12 N4 O1 B2 F4'
_chemical_oxdiff_usercomment     WDH-SD-38
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.936
_diffrn_oxdiff_ac4_digest_frames
;
01c6228ec08f6248d8e5f853fb35e765da000273461
;
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), N16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_submission_original_sample_id WDH-SD-38
_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 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.587