#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/22/79/7227962.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_7227962
loop_
_publ_author_name
'Campillo-Alvarado, Gonzalo'
'Staudt, Colton'
'Bak, Melissa'
'MacGillivray, Len R.'
_publ_section_title
;
 Generation of cocrystals of Tavaborole (AN2690): opportunities for
 boron-containing APIs
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00314E
_journal_year                    2017
_chemical_formula_moiety         '2(C7 H6 B F O2), C12 H12 N2'
_chemical_formula_sum            'C26 H24 B2 F2 N2 O4'
_chemical_formula_weight         488.09
_chemical_name_common            2(AN2690)(bpeta)
_chemical_name_systematic
'5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole, 1,2-bis(4-pyridyl)ethane'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-02-08 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.690(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.0294(15)
_cell_length_b                   5.9476(6)
_cell_length_c                   14.5384(15)
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      1.00
_cell_measurement_theta_min      25.35
_cell_volume                     1215.8(2)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6955
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.367
_diffrn_reflns_theta_max         25.367
_diffrn_reflns_theta_min         2.829
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       irregular
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method
'Slow evaporation of a methanol solution containing 1 equivalent of 4,4'-bpeta and 2 equivalents of AN2690'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0467
_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/[σ²(Fo²)+(0.0850P)²+0.2480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1760
_reflns_number_total             2208
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce00314e2.cif
_cod_data_source_block           mcg16173a
_cod_database_code               7227962
_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   0.986
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C5(H5), C9(H9), C8(H8), C11(H11), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.28717(9) 0.6157(2) 0.50189(8) 0.0632(4) Uani 1 1 d .
O2 O 0.21813(10) 0.9504(2) 0.53922(10) 0.0687(4) Uani 1 1 d .
H2 H 0.1974 0.9578 0.4790 0.103 Uiso 1 1 calc GR
F1 F 0.47226(10) 0.2846(2) 0.90998(9) 0.0948(5) Uani 1 1 d .
N1 N 0.14821(11) 1.0131(3) 0.33988(12) 0.0653(4) Uani 1 1 d .
C2 C 0.36587(11) 0.4736(3) 0.66075(12) 0.0505(4) Uani 1 1 d .
C1 C 0.32451(11) 0.6751(3) 0.67321(12) 0.0490(4) Uani 1 1 d .
C6 C 0.33496(12) 0.7441(3) 0.76794(13) 0.0573(5) Uani 1 1 d .
H6 H 0.3083 0.8791 0.7776 0.069 Uiso 1 1 calc R
C7 C 0.34664(14) 0.4331(3) 0.55350(13) 0.0625(5) Uani 1 1 d .
H7A H 0.4057 0.4310 0.5405 0.075 Uiso 1 1 calc R
H7B H 0.3145 0.2904 0.5331 0.075 Uiso 1 1 calc R
C3 C 0.41652(12) 0.3394(3) 0.73965(13) 0.0585(5) Uani 1 1 d .
H3 H 0.4442 0.2049 0.7310 0.070 Uiso 1 1 calc R
C5 C 0.38497(13) 0.6122(3) 0.84777(13) 0.0637(5) Uani 1 1 d .
H5 H 0.3921 0.6562 0.9114 0.076 Uiso 1 1 calc R
C4 C 0.42389(13) 0.4143(3) 0.83088(13) 0.0619(5) Uani 1 1 d .
C10 C 0.08617(12) 1.0031(4) 0.13451(15) 0.0674(6) Uani 1 1 d .
C9 C 0.13652(13) 1.1840(4) 0.18788(15) 0.0695(6) Uani 1 1 d .
H9 H 0.1508 1.3061 0.1556 0.083 Uiso 1 1 calc R
B1 B 0.27234(14) 0.7647(3) 0.56776(15) 0.0538(5) Uani 1 1 d .
C8 C 0.16519(14) 1.1821(3) 0.28839(15) 0.0690(5) Uani 1 1 d .
H8 H 0.1984 1.3061 0.3226 0.083 Uiso 1 1 calc R
C11 C 0.06883(14) 0.8267(4) 0.18793(16) 0.0734(6) Uani 1 1 d .
H11 H 0.0355 0.7008 0.1557 0.088 Uiso 1 1 calc R
C12 C 0.10103(14) 0.8381(4) 0.28876(15) 0.0693(5) Uani 1 1 d .
H12 H 0.0892 0.7168 0.3231 0.083 Uiso 1 1 calc R
C13 C 0.05168(14) 0.9952(6) 0.02429(16) 0.0927(8) Uani 1 1 d .
H13A H 0.0796 1.1201 0.0011 0.111 Uiso 1 1 calc R
H13B H 0.0746 0.8576 0.0045 0.111 Uiso 1 1 calc R
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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
B1 O1 C7 110.26(14) .
B1 O2 H2 109.5 .
C12 N1 C8 116.59(17) .
C1 C2 C7 110.04(15) .
C3 C2 C1 121.96(16) .
C3 C2 C7 128.00(16) .
C2 C1 C6 118.91(16) .
C2 C1 B1 105.13(14) .
C6 C1 B1 135.92(16) .
C1 C6 H6 120.0 .
C5 C6 C1 120.08(17) .
C5 C6 H6 120.0 .
O1 C7 C2 106.06(14) .
O1 C7 H7A 110.5 .
O1 C7 H7B 110.5 .
C2 C7 H7A 110.5 .
C2 C7 H7B 110.5 .
H7A C7 H7B 108.7 .
C2 C3 H3 121.7 .
C4 C3 C2 116.65(17) .
C4 C3 H3 121.7 .
C6 C5 H5 120.8 .
C4 C5 C6 118.39(17) .
C4 C5 H5 120.8 .
F1 C4 C3 118.09(18) .
F1 C4 C5 117.91(17) .
C3 C4 C5 124.00(17) .
C9 C10 C13 122.5(2) .
C11 C10 C9 116.66(19) .
C11 C10 C13 120.9(2) .
C10 C9 H9 120.2 .
C8 C9 C10 119.69(19) .
C8 C9 H9 120.2 .
O1 B1 C1 108.44(16) .
O2 B1 O1 122.76(17) .
O2 B1 C1 128.78(17) .
N1 C8 C9 123.7(2) .
N1 C8 H8 118.1 .
C9 C8 H8 118.1 .
C10 C11 H11 120.1 .
C12 C11 C10 119.7(2) .
C12 C11 H11 120.1 .
N1 C12 C11 123.57(19) .
N1 C12 H12 118.2 .
C11 C12 H12 118.2 .
C10 C13 H13A 108.5 .
C10 C13 H13B 108.5 .
C13 C13 C10 114.9(2) 3_575
C13 C13 H13A 108.5 3_575
C13 C13 H13B 108.5 3_575
H13A C13 H13B 107.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.438(2) .
O1 B1 1.380(2) .
O2 H2 0.8200 .
O2 B1 1.348(2) .
F1 C4 1.362(2) .
N1 C8 1.331(2) .
N1 C12 1.329(3) .
C2 C1 1.391(2) .
C2 C7 1.501(2) .
C2 C3 1.384(2) .
C1 C6 1.392(2) .
C1 B1 1.549(3) .
C6 H6 0.9300 .
C6 C5 1.382(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C3 H3 0.9300 .
C3 C4 1.366(3) .
C5 H5 0.9300 .
C5 C4 1.374(3) .
C10 C9 1.385(3) .
C10 C11 1.384(3) .
C10 C13 1.501(3) .
C9 H9 0.9300 .
C9 C8 1.370(3) .
C8 H8 0.9300 .
C11 H11 0.9300 .
C11 C12 1.373(3) .
C12 H12 0.9300 .
C13 C13 1.463(4) 3_575
C13 H13A 0.9700 .
C13 H13B 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 N1 0.82 1.92 2.737(2) 173.2 .
C7 H7B O2 0.97 2.51 3.425(2) 157.9 1_545
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_4
C2 C1 C6 C5 -0.6(3) .
C2 C1 B1 O1 -0.84(18) .
C2 C1 B1 O2 177.20(18) .
C2 C3 C4 F1 179.17(15) .
C2 C3 C4 C5 -0.4(3) .
C1 C2 C7 O1 -2.95(18) .
C1 C2 C3 C4 0.1(3) .
C1 C6 C5 C4 0.3(3) .
C6 C1 B1 O1 -178.59(17) .
C6 C1 B1 O2 -0.6(3) .
C6 C5 C4 F1 -179.39(17) .
C6 C5 C4 C3 0.2(3) .
C7 O1 B1 O2 -179.21(16) .
C7 O1 B1 C1 -1.03(19) .
C7 C2 C1 C6 -179.49(15) .
C7 C2 C1 B1 2.29(18) .
C7 C2 C3 C4 179.99(16) .
C3 C2 C1 C6 0.4(2) .
C3 C2 C1 B1 -177.81(15) .
C3 C2 C7 O1 177.16(16) .
C10 C9 C8 N1 0.6(3) .
C10 C11 C12 N1 0.7(3) .
C9 C10 C11 C12 0.2(3) .
C9 C10 C13 C13 -112.3(3) 3_575
B1 O1 C7 C2 2.37(19) .
B1 C1 C6 C5 176.89(18) .
C8 N1 C12 C11 -1.0(3) .
C11 C10 C9 C8 -0.8(3) .
C11 C10 C13 C13 67.8(4) 3_575
C12 N1 C8 C9 0.3(3) .
C13 C10 C9 C8 179.30(18) .
C13 C10 C11 C12 -179.90(19) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203389
