Functionalized 1,3-dipyrrolyl-1,3-diketone difluoroboron complexes
Shenoy, Ankitha M.; Fernandes, Premie P.; Lakshmi, Vellanki; New Journal of Chemistry 49 (2025) 3987–3996; doi:10.1039/D4NJ04611K

data_7063627
_publ_section_title
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 Functionalized 1,3-dipyrrolyl-1,3-diketone difluoroboron complexes
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_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3987
_journal_page_last               3996
_journal_paper_doi               10.1039/D4NJ04611K
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         '2(C12 H9 B F2 N2 O3), 3(H2 O)'
_chemical_formula_sum            'C24 H24 B2 F4 N4 O9'
_chemical_formula_weight         610.09
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-01-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-24 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.7798(8)
_cell_length_b                   6.9614(3)
_cell_length_c                   20.1643(8)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      24.20
_cell_measurement_theta_min      2.29
_cell_volume                     2776.5(2)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            109250
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_min         2.020
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       plate
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       0.0076(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         6917
_refine_ls_number_restraints     217
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0571P)^2^+0.3853P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1391
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3756
_reflns_number_total             6917
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj04611k1.cif
_cod_data_source_block           ak_cho_180724_0m_ccdc2388456
_cod_depositor_comments
'Adding full bibliography for 7063627--7063628.cif.'
_cod_database_code               7063627
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.974
_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 O(H,H) groups
2. Restrained distances
 O2A-C5 \\sim O2-C5 \\sim O1A-C7 \\sim O1-C7 \\sim O5A-C19 \\sim O5-C19 \\sim
O4A-C17 \\sim O4-C17
 with sigma of 0.01
 O2A-B1A \\sim O2-B1 \\sim O1A-B1A \\sim O1-B1 \\sim O5A-B2A \\sim O5-B2 \\sim
O4A-B2A \\sim O4-B2
 with sigma of 0.01
 F2A-B1A \\sim F2-B1 \\sim F1-B1 \\sim F1A-B1A \\sim F3A-B2A \\sim F4-B2 \\sim
F3-B2 \\sim F4A-B2A
 with sigma of 0.01
3. Restrained planarity
 B1A, O2A, C5, C6, C7, O1A
 with sigma of 0.02
 B1, O2, C5, C7, C6, O1
 with sigma of 0.02
 O4, B2, O5, C19, C18, C17
 with sigma of 0.02
 O4A, B2A, O5A, C19, C18, C17
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F2) \\sim
Ueq, Uanis(B1) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(B1A) \\sim Ueq,
Uanis(O1A) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(O4)
\\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F3) \\sim Ueq,
Uanis(B2) \\sim Ueq, Uanis(B2A) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(O5A)
\\sim Ueq, Uanis(F4A) \\sim Ueq, Uanis(O4A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(O2A) = Uanis(O2)
Uanis(O1) = Uanis(O1A)
Uanis(B1) = Uanis(B1A)
Uanis(O4) = Uanis(O4A)
Uanis(O5) = Uanis(O5A)
Uanis(B2) = Uanis(B2A)
Uanis(O9A) = Uanis(O9)
5. Others
 Sof(O2A)=Sof(B1A)=Sof(O1A)=Sof(F1A)=Sof(F2A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(F1)=Sof(F2)=Sof(B1)=FVAR(1)
 Sof(B2A)=Sof(F3A)=Sof(O5A)=Sof(F4A)=Sof(O4A)=1-FVAR(2)
 Sof(O4)=Sof(O5)=Sof(F4)=Sof(F3)=Sof(B2)=FVAR(2)
 Sof(O9A)=Sof(H9AA)=Sof(H9AB)=1-FVAR(3)
 Sof(O9)=Sof(H9A)=Sof(H9B)=FVAR(3)
6.a Riding coordinates:
 O9A(H9AA,H9AB)
6.b Free rotating group:
 O8(H8A,H8B), O7(H7A,H7B), O9(H9A,H9B)
6.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N2(H2), N1(H1), N3(H3), C18(H18), C6(H6), C9(H9), C3(H3A), C15(H15),
 C2(H2A), C22(H22), C24(H24), C13(H13), C12(H12), C10(H10), C1(H1A), C21(H21),
 C14(H14)
;
_shelx_res_checksum              65552
_shelx_hkl_checksum              22527
_olex2_submission_special_instructions 'No special instructions were received'