#------------------------------------------------------------------------------
#$Date: 2024-09-27 04:26:45 +0300 (Fri, 27 Sep 2024) $
#$Revision: 294917 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249397.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7249397
loop_
_publ_author_name
'Thomas, Jarrod R.'
'Mifsud, Jonathan T.'
'Sulway, Scott A.'
_publ_section_title
;
 Optimised syntheses and purifications of 3-aryl/heterocyclic dihydrobis-
 and hydrotris-(pyrazolyl)borate ligands as their alkali salts
;
_journal_issue                   42
_journal_name_full               'RSC Advances'
_journal_page_first              30713
_journal_page_last               30718
_journal_paper_doi               10.1039/D4RA05723F
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C32 H28 B2 N12 Na2'
_chemical_formula_sum            'C32 H28 B2 N12 Na2'
_chemical_formula_weight         648.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-05-22 deposited with the CCDC.	2024-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.251(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7237(10)
_cell_length_b                   10.8738(7)
_cell_length_c                   20.0182(11)
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.291
_cell_measurement_theta_min      2.333
_cell_volume                     3189.9(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8Quest'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35586
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.352
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1189 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.8368.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0571
_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/[σ²(Fo²)+(0.0672P)²+6.5161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1616
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2945
_reflns_number_total             3661
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ra05723f2.cif
_cod_data_source_block           jrt247_230929_a
_cod_database_code               7249397
_shelx_shelxl_version_number     2019/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups
2.a Secondary CH2 refined with riding coordinates:
 B1(H1a,H1b)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C8(H8), C9(H9), C14(H14), C16(H16), C1(H1), C7(H7),
 C15(H15), C5(H5), C2(H2), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Na1 Na 0.48361(6) 0.51138(7) 0.32618(4) 0.0272(2) Uani 1 1 d . . . . .
N5 N 0.63541(11) 0.52737(15) 0.29043(9) 0.0247(4) Uani 1 1 d . . . . .
N4 N 0.68612(11) 0.62237(15) 0.32897(9) 0.0252(4) Uani 1 1 d . . . . .
N3 N 0.42463(11) 0.56014(16) 0.42370(9) 0.0273(4) Uani 1 1 d . . . . .
N1 N 0.60116(11) 0.78102(15) 0.37287(9) 0.0260(4) Uani 1 1 d . . . . .
N6 N 0.57937(12) 0.30543(15) 0.21817(9) 0.0262(4) Uani 1 1 d . . . . .
N2 N 0.54286(12) 0.69767(14) 0.38194(9) 0.0251(4) Uani 1 1 d . . . . .
C11 C 0.68874(13) 0.42674(17) 0.31028(10) 0.0241(4) Uani 1 1 d . . . . .
C13 C 0.70275(15) 0.19925(19) 0.30709(11) 0.0292(4) Uani 1 1 d . . . . .
H13 H 0.757042 0.203155 0.348394 0.035 Uiso 1 1 calc R U . . .
C12 C 0.65604(13) 0.30675(17) 0.27717(10) 0.0237(4) Uani 1 1 d . . . . .
C10 C 0.77351(14) 0.45653(19) 0.36292(11) 0.0292(4) Uani 1 1 d . . . . .
H10 H 0.823009 0.402933 0.386590 0.035 Uiso 1 1 calc R U . . .
C3 C 0.50930(13) 0.74609(18) 0.42902(10) 0.0252(4) Uani 1 1 d . . . . .
C4 C 0.44612(13) 0.67410(19) 0.45195(10) 0.0262(4) Uani 1 1 d . . . . .
C8 C 0.37016(14) 0.4911(2) 0.44658(12) 0.0328(5) Uani 1 1 d . . . . .
H8 H 0.354859 0.410959 0.426957 0.039 Uiso 1 1 calc R U . . .
C9 C 0.76825(14) 0.58148(19) 0.37228(11) 0.0290(4) Uani 1 1 d . . . . .
H9 H 0.815265 0.630892 0.404298 0.035 Uiso 1 1 calc R U . . .
C14 C 0.66961(16) 0.08741(19) 0.27635(12) 0.0325(5) Uani 1 1 d . . . . .
H14 H 0.701436 0.013536 0.295366 0.039 Uiso 1 1 calc R U . . .
C16 C 0.54748(15) 0.19515(19) 0.19010(11) 0.0300(4) Uani 1 1 d . . . . .
H16 H 0.492874 0.193008 0.149005 0.036 Uiso 1 1 calc R U . . .
C1 C 0.60438(15) 0.88158(19) 0.41321(12) 0.0317(5) Uani 1 1 d . . . . .
H1 H 0.640261 0.952906 0.415613 0.038 Uiso 1 1 calc R U . . .
C7 C 0.33464(15) 0.5297(2) 0.49739(13) 0.0388(5) Uani 1 1 d . . . . .
H7 H 0.297544 0.476647 0.512979 0.047 Uiso 1 1 calc R U . . .
C15 C 0.58897(16) 0.08447(19) 0.21713(12) 0.0321(5) Uani 1 1 d . . . . .
H15 H 0.563022 0.008647 0.195780 0.039 Uiso 1 1 calc R U . . .
C5 C 0.41075(16) 0.7211(2) 0.50149(11) 0.0338(5) Uani 1 1 d . . . . .
H5 H 0.424869 0.802627 0.519126 0.041 Uiso 1 1 calc R U . . .
C2 C 0.54686(15) 0.8633(2) 0.45027(12) 0.0333(5) Uani 1 1 d . . . . .
H2 H 0.535166 0.917885 0.482995 0.040 Uiso 1 1 calc R U . . .
C6 C 0.35482(16) 0.6475(2) 0.52459(12) 0.0397(5) Uani 1 1 d . . . . .
H6 H 0.330711 0.677556 0.558643 0.048 Uiso 1 1 calc R U . . .
B1 B 0.65144(17) 0.7565(2) 0.31961(13) 0.0288(5) Uani 1 1 d . . . . .
H1A H 0.609068 0.769929 0.269725 0.035 Uiso 1 1 calc R U . . .
H1B H 0.703469 0.813845 0.329536 0.035 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Na1 N5 100.76(6) 2_655 . ?
N5 Na1 N3 111.28(6) 2_655 . ?
N5 Na1 N6 69.47(6) 2_655 2_655 ?
N3 Na1 N5 142.75(6) . . ?
N6 Na1 N5 103.70(6) 2_655 . ?
N6 Na1 N3 104.94(6) 2_655 . ?
N2 Na1 N5 115.79(6) . 2_655 ?
N2 Na1 N5 80.52(6) . . ?
N2 Na1 N3 68.91(6) . . ?
N2 Na1 N6 172.82(7) . 2_655 ?
Na1 N5 Na1 78.70(5) 2_655 . ?
N4 N5 Na1 106.71(11) . . ?
N4 N5 Na1 133.88(12) . 2_655 ?
C11 N5 Na1 114.11(12) . 2_655 ?
C11 N5 Na1 112.34(12) . . ?
C11 N5 N4 105.96(16) . . ?
N5 N4 B1 122.64(16) . . ?
C9 N4 N5 110.07(16) . . ?
C9 N4 B1 127.25(18) . . ?
C4 N3 Na1 114.40(13) . . ?
C8 N3 Na1 127.73(15) . . ?
C8 N3 C4 117.68(19) . . ?
N2 N1 C1 110.14(17) . . ?
N2 N1 B1 120.93(16) . . ?
C1 N1 B1 128.89(18) . . ?
C12 N6 Na1 114.75(13) . 2_655 ?
C16 N6 Na1 128.10(14) . 2_655 ?
C16 N6 C12 117.15(17) . . ?
N1 N2 Na1 133.75(13) . . ?
C3 N2 Na1 119.00(13) . . ?
C3 N2 N1 106.88(16) . . ?
N5 C11 C12 120.61(17) . . ?
N5 C11 C10 110.71(17) . . ?
C10 C11 C12 128.67(18) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C14 C13 C12 119.54(19) . . ?
N6 C12 C11 117.41(17) . . ?
N6 C12 C13 122.14(18) . . ?
C13 C12 C11 120.45(18) . . ?
C11 C10 H10 128.0 . . ?
C9 C10 C11 104.00(18) . . ?
C9 C10 H10 128.0 . . ?
N2 C3 C4 119.64(17) . . ?
N2 C3 C2 109.84(18) . . ?
C2 C3 C4 130.48(19) . . ?
N3 C4 C3 116.99(17) . . ?
N3 C4 C5 121.9(2) . . ?
C5 C4 C3 121.12(19) . . ?
N3 C8 H8 118.1 . . ?
N3 C8 C7 123.8(2) . . ?
C7 C8 H8 118.1 . . ?
N4 C9 C10 109.24(18) . . ?
N4 C9 H9 125.4 . . ?
C10 C9 H9 125.4 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.87(19) . . ?
C15 C14 H14 120.6 . . ?
N6 C16 H16 117.9 . . ?
N6 C16 C15 124.2(2) . . ?
C15 C16 H16 117.9 . . ?
N1 C1 H1 125.8 . . ?
N1 C1 C2 108.43(19) . . ?
C2 C1 H1 125.8 . . ?
C8 C7 H7 120.9 . . ?
C6 C7 C8 118.2(2) . . ?
C6 C7 H7 120.9 . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 118.0(2) . . ?
C16 C15 H15 121.0 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C3 C2 H2 127.6 . . ?
C1 C2 C3 104.72(18) . . ?
C1 C2 H2 127.6 . . ?
C7 C6 C5 119.1(2) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N4 B1 N1 108.78(16) . . ?
N4 B1 H1A 109.9 . . ?
N4 B1 H1B 109.9 . . ?
N1 B1 H1A 109.9 . . ?
N1 B1 H1B 109.9 . . ?
H1A B1 H1B 108.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 N5 2.4114(18) 2_655 ?
Na1 N5 2.7345(19) . ?
Na1 N3 2.5028(19) . ?
Na1 N6 2.4793(18) 2_655 ?
Na1 N2 2.3374(17) . ?
N5 N4 1.361(2) . ?
N5 C11 1.348(2) . ?
N4 C9 1.344(3) . ?
N4 B1 1.544(3) . ?
N3 C4 1.353(3) . ?
N3 C8 1.339(3) . ?
N1 N2 1.347(2) . ?
N1 C1 1.349(3) . ?
N1 B1 1.563(3) . ?
N6 C12 1.348(3) . ?
N6 C16 1.342(3) . ?
N2 C3 1.343(3) . ?
C11 C12 1.469(3) . ?
C11 C10 1.405(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.395(3) . ?
C13 C14 1.377(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.378(3) . ?
C3 C4 1.463(3) . ?
C3 C2 1.404(3) . ?
C4 C5 1.398(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.391(3) . ?
C9 H9 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C15 1.382(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.376(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.383(4) . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C2 H2 0.9500 . ?
C6 H6 0.9500 . ?
B1 H1A 0.9900 . ?
B1 H1B 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 N5 N4 C9 -150.63(15) 2_655 . . . ?
Na1 N5 N4 C9 119.09(14) . . . . ?
Na1 N5 N4 B1 -62.96(19) . . . . ?
Na1 N5 N4 B1 27.3(3) 2_655 . . . ?
Na1 N5 C11 C12 65.67(19) . . . . ?
Na1 N5 C11 C12 -21.6(2) 2_655 . . . ?
Na1 N5 C11 C10 157.83(13) 2_655 . . . ?
Na1 N5 C11 C10 -114.93(15) . . . . ?
Na1 N3 C4 C3 -7.6(2) . . . . ?
Na1 N3 C4 C5 173.17(15) . . . . ?
Na1 N3 C8 C7 -174.62(16) . . . . ?
Na1 N6 C12 C11 4.1(2) 2_655 . . . ?
Na1 N6 C12 C13 -176.87(15) 2_655 . . . ?
Na1 N6 C16 C15 177.65(16) 2_655 . . . ?
Na1 N2 C3 C4 8.5(2) . . . . ?
Na1 N2 C3 C2 -173.72(13) . . . . ?
N5 N4 C9 C10 0.1(2) . . . . ?
N5 N4 B1 N1 90.4(2) . . . . ?
N5 C11 C12 N6 11.9(3) . . . . ?
N5 C11 C12 C13 -167.12(18) . . . . ?
N5 C11 C10 C9 -1.2(2) . . . . ?
N4 N5 C11 C12 -178.16(16) . . . . ?
N4 N5 C11 C10 1.2(2) . . . . ?
N3 C4 C5 C6 2.5(3) . . . . ?
N3 C8 C7 C6 1.7(3) . . . . ?
N1 N2 C3 C4 -177.60(16) . . . . ?
N1 N2 C3 C2 0.2(2) . . . . ?
N1 C1 C2 C3 -0.3(2) . . . . ?
N6 C16 C15 C14 -1.2(3) . . . . ?
N2 N1 C1 C2 0.4(2) . . . . ?
N2 N1 B1 N4 -43.5(2) . . . . ?
N2 C3 C4 N3 0.0(3) . . . . ?
N2 C3 C4 C5 179.25(18) . . . . ?
N2 C3 C2 C1 0.0(2) . . . . ?
C11 N5 N4 C9 -0.8(2) . . . . ?
C11 N5 N4 B1 177.13(17) . . . . ?
C11 C10 C9 N4 0.6(2) . . . . ?
C13 C14 C15 C16 2.4(3) . . . . ?
C12 N6 C16 C15 -1.1(3) . . . . ?
C12 C11 C10 C9 178.18(19) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C10 C11 C12 N6 -167.34(19) . . . . ?
C10 C11 C12 C13 13.6(3) . . . . ?
C3 C4 C5 C6 -176.68(19) . . . . ?
C4 N3 C8 C7 0.0(3) . . . . ?
C4 C3 C2 C1 177.5(2) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C8 N3 C4 C3 177.07(17) . . . . ?
C8 N3 C4 C5 -2.2(3) . . . . ?
C8 C7 C6 C5 -1.3(3) . . . . ?
C9 N4 B1 N1 -92.0(2) . . . . ?
C14 C13 C12 N6 -0.7(3) . . . . ?
C14 C13 C12 C11 178.27(18) . . . . ?
C16 N6 C12 C11 -176.99(17) . . . . ?
C16 N6 C12 C13 2.0(3) . . . . ?
C1 N1 N2 Na1 172.26(15) . . . . ?
C1 N1 N2 C3 -0.4(2) . . . . ?
C1 N1 B1 N4 138.9(2) . . . . ?
C2 C3 C4 N3 -177.3(2) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
B1 N4 C9 C10 -177.72(18) . . . . ?
B1 N1 N2 Na1 -5.8(3) . . . . ?
B1 N1 N2 C3 -178.42(17) . . . . ?
B1 N1 C1 C2 178.25(19) . . . . ?
