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_7126360
_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 H11 B2 F4 N3 O2'
_chemical_formula_sum            'C12 H11 B2 F4 N3 O2'
_chemical_formula_weight         326.86
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-18
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.9330(10)
_cell_length_b                   12.5943(6)
_cell_length_c                   4.7440(2)
_cell_measurement_reflns_used    3334
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0740
_cell_measurement_theta_min      3.0200
_cell_volume                     1429.93(11)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -25.00  92.00   1.00   60.00    --   18.87  19.00   0.00  117
  2  \w    -50.00  40.00   1.00   60.00    --   18.87 -57.00-180.00   90
  3  \w    -87.00 -46.00   1.00   60.00    --  -17.07 -77.00 150.00   41
  4  \w     34.00  95.00   1.00   60.00    --   18.87-178.00  60.00   61
;
_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      0.0276651000
_diffrn_orient_matrix_UB_12      0.0153259000
_diffrn_orient_matrix_UB_13      -0.0348029000
_diffrn_orient_matrix_UB_21      -0.0091392000
_diffrn_orient_matrix_UB_22      0.0530319000
_diffrn_orient_matrix_UB_23      -0.0202842000
_diffrn_orient_matrix_UB_31      0.0054126000
_diffrn_orient_matrix_UB_32      0.0111969000
_diffrn_orient_matrix_UB_33      0.1439826000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8443
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.023
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46642
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 754 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0429P)^2^+0.2150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                2241
_reflns_number_total             2817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01131b2.cif
_cod_data_source_block           wdh1098
_cod_depositor_comments
'Adding full bibliography for 7126359--7126362.cif.'
_cod_database_code               7126360
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C12 H11 B2 F4 N3 O2'
_chemical_oxdiff_usercomment     JK021
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.935
_diffrn_oxdiff_ac4_digest_frames
;
0141da7c765bba9ad1a2920f72bfe22929000276d90
;
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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 1.714
_oxdiff_exptl_absorpt_empirical_full_min 0.423