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#$Date: 2025-10-17 03:53:23 +0300 (Fri, 17 Oct 2025) $
#$Revision: 302945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/40/7064073.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_7064073
loop_
_publ_author_name
'Prasannan, Dijo'
'Nemykin, Viktor N.'
_publ_section_title
;
 Unexpected Formation of α-Formylated BOPHY in the Reaction with Copper
 Salts
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ02748A
_journal_year                    2025
_chemical_formula_moiety         'C14 H15 B F2 N4 O'
_chemical_formula_sum            'C14 H15 B F2 N4 O'
_chemical_formula_weight         304.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-06-16 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4025(19)
_cell_length_b                   6.7909(8)
_cell_length_c                   12.6068(15)
_cell_measurement_reflns_used    3100
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.08
_cell_measurement_theta_min      2.48
_cell_volume                     1404.2(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0901
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15155
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.304
_diffrn_reflns_theta_min         2.483
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5476
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1526 before and 0.0749 after correction.
The Ratio of minimum to maximum transmission is 0.7343.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.675
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0676
_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)+(0.0323P)²+1.9472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1430
_reflns_number_total             1874
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj02748a2.cif
_cod_data_source_block           bophy_alkyne_a
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               7064073
_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   0.992
_shelx_estimated_absorpt_t_min   0.929
_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. Others
 Fixed Sof: H8A(0.5) H8B(0.5) H8C(0.5) H9A(0.5) H9B(0.5) H9C(0.5) H14A(0.5)
 H14B(0.5) H14C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C11(H11), C13(H13), N1(H1)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
C1 C 0.53890(18) 0.250000 0.3341(2) 0.0172(7) Uani 1 2 d S T P . .
C2 C 0.67491(19) 0.250000 0.3278(3) 0.0198(7) Uani 1 2 d S T P . .
C3 C 0.64537(19) 0.250000 0.2232(3) 0.0216(7) Uani 1 2 d S T P . .
H3 H 0.677942 0.250000 0.160849 0.026 Uiso 1 2 calc R U P . .
C4 C 0.56129(19) 0.250000 0.2258(2) 0.0196(7) Uani 1 2 d S T P . .
C5 C 0.45990(18) 0.250000 0.3737(2) 0.0168(7) Uani 1 2 d S T P . .
H5 H 0.418163 0.250000 0.321486 0.020 Uiso 1 2 calc R U P . .
C6 C 0.38466(18) 0.250000 0.6835(2) 0.0160(6) Uani 1 2 d S T P . .
C7 C 0.46841(18) 0.250000 0.6489(2) 0.0164(6) Uani 1 2 d S T P . .
H7 H 0.508836 0.250000 0.702850 0.020 Uiso 1 2 calc R U P . .
C8 C 0.76056(19) 0.250000 0.3669(3) 0.0260(8) Uani 1 2 d S T P . .
H8A H 0.779323 0.113943 0.375543 0.039 Uiso 0.5 1 calc R U P A -1
H8B H 0.763256 0.318248 0.435256 0.039 Uiso 0.5 1 calc R U P A -1
H8C H 0.795495 0.317809 0.315444 0.039 Uiso 0.5 1 calc R U P A -1
C9 C 0.5036(2) 0.250000 0.1331(2) 0.0266(8) Uani 1 2 d S T P . .
H9A H 0.466406 0.362483 0.138973 0.040 Uiso 0.5 1 calc R U P B -1
H9B H 0.472004 0.127468 0.133070 0.040 Uiso 0.5 1 calc R U P B -1
H9C H 0.534670 0.260049 0.066993 0.040 Uiso 0.5 1 calc R U P B -1
C10 C 0.25071(18) 0.250000 0.6642(2) 0.0165(6) Uani 1 2 d S T P . .
C11 C 0.26714(18) 0.250000 0.7728(2) 0.0171(7) Uani 1 2 d S T P . .
H11 H 0.227837 0.250000 0.828099 0.021 Uiso 1 2 calc R U P . .
C12 C 0.35148(19) 0.250000 0.7855(2) 0.0177(7) Uani 1 2 d S T P . .
C13 C 0.17288(19) 0.250000 0.6099(3) 0.0210(7) Uani 1 2 d S T P . .
H13 H 0.173648 0.250000 0.534536 0.025 Uiso 1 2 calc R U P . .
C14 C 0.3973(2) 0.250000 0.8888(2) 0.0264(8) Uani 1 2 d S T P . .
H14A H 0.454836 0.280208 0.875520 0.040 Uiso 0.5 1 calc R U P C -1
H14B H 0.392864 0.120007 0.922061 0.040 Uiso 0.5 1 calc R U P C -1
H14C H 0.374103 0.349784 0.936151 0.040 Uiso 0.5 1 calc R U P C -1
B1 B 0.3380(2) 0.250000 0.4904(3) 0.0170(8) Uani 1 2 d S T P . .
F1 F 0.30588(7) 0.4166(2) 0.44224(10) 0.0279(4) Uani 1 1 d . . . . .
N1 N 0.61089(15) 0.250000 0.3927(2) 0.0192(6) Uani 1 2 d S T P . .
H1 H 0.613634 0.250000 0.462442 0.023 Uiso 1 2 calc R U P . .
N2 N 0.43357(14) 0.250000 0.47374(19) 0.0152(6) Uani 1 2 d S T P . .
N3 N 0.32364(15) 0.250000 0.60975(19) 0.0151(6) Uani 1 2 d S T P . .
N4 N 0.49432(15) 0.250000 0.55137(19) 0.0172(6) Uani 1 2 d S T P . .
O1 O 0.10683(14) 0.250000 0.65314(19) 0.0319(7) Uani 1 2 d S T P . .
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C4 126.2(3) . . ?
C5 C1 N1 126.8(3) . . ?
N1 C1 C4 107.0(3) . . ?
C3 C2 C8 129.5(3) . . ?
N1 C2 C3 107.8(3) . . ?
N1 C2 C8 122.8(3) . . ?
C2 C3 H3 125.6 . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 H3 125.6 . . ?
C1 C4 C9 125.9(3) . . ?
C3 C4 C1 106.5(3) . . ?
C3 C4 C9 127.6(3) . . ?
C1 C5 H5 115.0 . . ?
N2 C5 C1 130.0(3) . . ?
N2 C5 H5 115.0 . . ?
C12 C6 C7 130.5(3) . . ?
N3 C6 C7 119.5(3) . . ?
N3 C6 C12 109.9(3) . . ?
C6 C7 H7 116.7 . . ?
N4 C7 C6 126.7(3) . . ?
N4 C7 H7 116.7 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C13 129.4(3) . . ?
N3 C10 C11 108.7(3) . . ?
N3 C10 C13 121.9(3) . . ?
C10 C11 H11 126.1 . . ?
C12 C11 C10 107.8(3) . . ?
C12 C11 H11 126.1 . . ?
C6 C12 C14 127.1(3) . . ?
C11 C12 C6 106.3(3) . . ?
C11 C12 C14 126.6(3) . . ?
C10 C13 H13 117.5 . . ?
O1 C13 C10 125.1(3) . . ?
O1 C13 H13 117.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F1 B1 F1 109.2(2) . 7_565 ?
F1 B1 N2 108.58(17) 7_565 . ?
F1 B1 N2 108.58(17) . . ?
F1 B1 N3 111.90(17) . . ?
F1 B1 N3 111.90(17) 7_565 . ?
N3 B1 N2 106.6(2) . . ?
C1 N1 H1 125.0 . . ?
C2 N1 C1 110.0(3) . . ?
C2 N1 H1 125.0 . . ?
C5 N2 B1 116.5(2) . . ?
C5 N2 N4 115.6(2) . . ?
N4 N2 B1 127.9(2) . . ?
C6 N3 C10 107.3(2) . . ?
C6 N3 B1 123.9(2) . . ?
C10 N3 B1 128.8(2) . . ?
C7 N4 N2 115.4(2) . . ?
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
C1 C4 1.413(4) . ?
C1 C5 1.389(4) . ?
C1 N1 1.393(4) . ?
C2 C3 1.406(4) . ?
C2 C8 1.489(4) . ?
C2 N1 1.331(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(4) . ?
C4 C9 1.504(4) . ?
C5 H5 0.9500 . ?
C5 N2 1.333(4) . ?
C6 C7 1.441(4) . ?
C6 C12 1.397(4) . ?
C6 N3 1.366(4) . ?
C7 H7 0.9500 . ?
C7 N4 1.301(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.394(4) . ?
C10 C13 1.449(4) . ?
C10 N3 1.379(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(4) . ?
C12 C14 1.504(4) . ?
C13 H13 0.9500 . ?
C13 O1 1.213(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
B1 F1 1.388(2) 7_565 ?
B1 F1 1.388(2) . ?
B1 N2 1.581(4) . ?
B1 N3 1.523(4) . ?
N1 H1 0.8800 . ?
N2 N4 1.397(3) . ?
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
C1 C5 N2 B1 180.000(0) . . . . ?
C1 C5 N2 N4 0.000(0) . . . . ?
C2 C3 C4 C1 0.000(0) . . . . ?
C2 C3 C4 C9 180.000(0) . . . . ?
C3 C2 N1 C1 0.000(0) . . . . ?
C4 C1 C5 N2 180.000(0) . . . . ?
C4 C1 N1 C2 0.000(0) . . . . ?
C5 C1 C4 C3 180.000(0) . . . . ?
C5 C1 C4 C9 0.000(0) . . . . ?
C5 C1 N1 C2 180.000(0) . . . . ?
C5 N2 N4 C7 180.000(0) . . . . ?
C6 C7 N4 N2 0.000(1) . . . . ?
C7 C6 C12 C11 180.000(1) . . . . ?
C7 C6 C12 C14 0.000(1) . . . . ?
C7 C6 N3 C10 180.000(1) . . . . ?
C7 C6 N3 B1 0.000(1) . . . . ?
C8 C2 C3 C4 180.000(0) . . . . ?
C8 C2 N1 C1 180.000(0) . . . . ?
C10 C11 C12 C6 0.000(1) . . . . ?
C10 C11 C12 C14 180.000(1) . . . . ?
C11 C10 C13 O1 0.000(1) . . . . ?
C11 C10 N3 C6 0.000(1) . . . . ?
C11 C10 N3 B1 180.000(1) . . . . ?
C12 C6 C7 N4 180.000(1) . . . . ?
C12 C6 N3 C10 0.000(1) . . . . ?
C12 C6 N3 B1 180.000(1) . . . . ?
C13 C10 C11 C12 180.000(1) . . . . ?
C13 C10 N3 C6 180.000(1) . . . . ?
C13 C10 N3 B1 0.000(1) . . . . ?
B1 N2 N4 C7 0.000(0) . . . . ?
F1 B1 N2 C5 59.30(17) 7_565 . . . ?
F1 B1 N2 C5 -59.30(17) . . . . ?
F1 B1 N2 N4 120.70(17) . . . . ?
F1 B1 N2 N4 -120.70(17) 7_565 . . . ?
F1 B1 N3 C6 118.55(19) 7_565 . . . ?
F1 B1 N3 C6 -118.54(19) . . . . ?
F1 B1 N3 C10 61.46(19) . . . . ?
F1 B1 N3 C10 -61.45(19) 7_565 . . . ?
N1 C1 C4 C3 0.000(0) . . . . ?
N1 C1 C4 C9 180.000(0) . . . . ?
N1 C1 C5 N2 0.000(0) . . . . ?
N1 C2 C3 C4 0.000(0) . . . . ?
N2 B1 N3 C6 0.000(1) . . . . ?
N2 B1 N3 C10 180.000(1) . . . . ?
N3 C6 C7 N4 0.000(1) . . . . ?
N3 C6 C12 C11 0.000(1) . . . . ?
N3 C6 C12 C14 180.000(1) . . . . ?
N3 C10 C11 C12 0.000(1) . . . . ?
N3 C10 C13 O1 180.000(1) . . . . ?
N3 B1 N2 C5 180.000(0) . . . . ?
N3 B1 N2 N4 0.000(0) . . . . ?
