#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:02:25 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289525 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/46/7714645.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_7714645
loop_
_publ_author_name
'Bedi, Vaibhav'
'Mandal, Dipendu'
'Hussain, Zahid'
'Chen, Shi-Ming'
'Wu, Yile'
'Qu, Zheng-Wang'
'Grimme, Stefan'
'Stephan, Douglas W.'
_publ_section_title
;
 The impact of Lewis acid variation on reactions with di-tert-butyl
 diazo diesters.
;
_journal_issue                   2
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              439
_journal_page_last               443
_journal_paper_doi               10.1039/d3dt03506a
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'B0.5 C12 F10, C4 H9.5 N'
_chemical_formula_sum            'C16 H9.5 B0.5 F10 N'
_chemical_formula_weight         411.157
_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'
_symmetry_Int_Tables_number      15
_audit_creation_date             2023-09-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-10-19 deposited with the CCDC.	2023-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.375(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.394(3)
_cell_length_b                   8.2279(11)
_cell_length_c                   19.557(3)
_cell_measurement_reflns_used    3733
_cell_measurement_temperature    150.02
_cell_measurement_theta_max      21.96
_cell_measurement_theta_min      2.76
_cell_volume                     3267.2(8)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.02
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.9997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32500
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.9997
_diffrn_reflns_theta_full        24.9934
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.01
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_description       Block
_exptl_crystal_F_000             1641.935
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.4123
_refine_diff_density_min         -0.3941
_refine_diff_density_rms         0.1030
_refine_ls_d_res_high            0.8411
_refine_ls_d_res_low             10.1524
_refine_ls_goodness_of_fit_ref   1.0887
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0887
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0354P)²+3.1341P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              24
_reflns_limit_h_min              -24
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                1869
_reflns_number_total             2869
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3dt03506a2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7714643--7714645.cif.'
_cod_database_code               7714645
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1)
3.b Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c), C27(H27a,H27b,H27c), C28(H28a,H28b,H28c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
F1 F 0.34869(7) 0.94643(18) 0.23178(7) 0.0351(4) Uani 1.000000 1 . . .
F2 F 0.55454(7) 0.78118(18) 0.15954(7) 0.0331(4) Uani 1.000000 1 . . .
F3 F 0.28936(7) 0.72398(18) 0.15153(8) 0.0391(4) Uani 1.000000 1 . . .
F4 F 0.50277(7) 1.07256(18) 0.09476(7) 0.0357(4) Uani 1.000000 1 . . .
F5 F 0.49306(8) 0.55242(18) 0.08134(8) 0.0401(4) Uani 1.000000 1 . . .
F6 F 0.57781(9) 1.28760(19) 0.03925(8) 0.0486(5) Uani 1.000000 1 . . .
F7 F 0.59600(8) 1.23040(18) 0.31612(7) 0.0386(4) Uani 1.000000 1 . . .
F8 F 0.67276(9) 1.4429(2) 0.25838(9) 0.0537(5) Uani 1.000000 1 . . .
F9 F 0.35936(8) 0.52000(18) 0.07594(8) 0.0427(4) Uani 1.000000 1 . . .
F10 F 0.66506(9) 1.47476(19) 0.11867(10) 0.0571(5) Uani 1.000000 1 . . .
N1 N 0.72750(10) 1.7410(3) 0.01797(11) 0.0328(6) Uani 1.000000 1 . . .
H1 H 0.72092(10) 1.6449(3) 0.03587(11) 0.0394(7) Uiso 0.500000 1 R . P
C12 C 0.48768(12) 0.7719(3) 0.15901(13) 0.0263(6) Uani 1.000000 1 . . .
C13 C 0.38816(13) 0.8563(3) 0.19431(13) 0.0261(6) Uani 1.000000 1 . . .
C14 C 0.45566(12) 0.8821(3) 0.19865(12) 0.0227(6) Uani 1.000000 1 . . .
C15 C 0.39047(14) 0.6358(3) 0.11554(13) 0.0287(6) Uani 1.000000 1 . . .
C16 C 0.54630(13) 1.1349(3) 0.20915(13) 0.0254(6) Uani 1.000000 1 . . .
C17 C 0.45781(13) 0.6523(3) 0.11822(13) 0.0278(6) Uani 1.000000 1 . . .
C18 C 0.62647(15) 1.3664(3) 0.14804(16) 0.0380(8) Uani 1.000000 1 . . .
C19 C 0.58298(14) 1.2722(3) 0.10824(14) 0.0336(7) Uani 1.000000 1 . . .
C20 C 0.59018(13) 1.2393(3) 0.24640(13) 0.0306(7) Uani 1.000000 1 . . .
C21 C 0.54448(13) 1.1602(3) 0.13903(14) 0.0283(6) Uani 1.000000 1 . . .
B22 B 0.5 1.0094(5) 0.25 0.0231(9) Uani 1.000000 2 S T P
C23 C 0.35574(13) 0.7387(3) 0.15386(13) 0.0278(6) Uani 1.000000 1 . . .
C2 C 0.68321(13) 1.8790(3) 0.03227(14) 0.0328(7) Uani 1.000000 1 . . .
C25 C 0.63016(14) 1.3512(3) 0.21825(15) 0.0361(7) Uani 1.000000 1 . . .
C26 C 0.61431(14) 1.8174(4) 0.00935(16) 0.0501(9) Uani 1.000000 1 . . .
H26a H 0.6098(4) 1.803(2) -0.04060(19) 0.0752(13) Uiso 1.000000 1 GR . .
H26b H 0.6071(4) 1.7132(13) 0.0317(8) 0.0752(13) Uiso 1.000000 1 GR . .
H26c H 0.58170(15) 1.8966(12) 0.0221(9) 0.0752(13) Uiso 1.000000 1 GR . .
C27 C 0.69347(14) 1.8969(3) 0.11019(14) 0.0351(7) Uani 1.000000 1 . . .
H27a H 0.6835(8) 1.7935(7) 0.13184(14) 0.0527(11) Uiso 1.000000 1 GR . .
H27b H 0.7393(2) 1.927(2) 0.12378(16) 0.0527(11) Uiso 1.000000 1 GR . .
H27c H 0.6642(6) 1.9817(15) 0.12500(17) 0.0527(11) Uiso 1.000000 1 GR . .
C28 C 0.70108(17) 2.0325(4) -0.00477(17) 0.0551(10) Uani 1.000000 1 . . .
H28a H 0.7466(4) 2.0630(15) 0.0102(8) 0.0826(14) Uiso 1.000000 1 GR . .
H28b H 0.6968(10) 2.0129(8) -0.05442(18) 0.0826(14) Uiso 1.000000 1 GR . .
H28c H 0.6714(7) 2.1207(8) 0.0059(9) 0.0826(14) Uiso 1.000000 1 GR . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
B 0.00156 0.00068 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.19320 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.01756 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
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
C2 N1 H1 119.43(13) . . ?
C14 C12 F2 118.6(2) . . ?
C17 C12 F2 115.7(2) . . ?
C17 C12 C14 125.7(2) . . ?
C14 C13 F1 121.2(2) . . ?
C23 C13 F1 114.6(2) . . ?
C23 C13 C14 124.2(2) . . ?
C13 C14 C12 112.3(2) . . ?
B22 C14 C12 119.3(2) 2_655 . ?
B22 C14 C13 128.0(2) 2_655 . ?
C17 C15 F9 120.4(2) . . ?
C23 C15 F9 120.7(2) . . ?
C23 C15 C17 118.9(2) . . ?
C21 C16 C20 112.4(2) . . ?
B22 C16 C20 119.9(2) 2_655 . ?
B22 C16 C21 127.5(2) 2_655 . ?
C12 C17 F5 121.3(2) . . ?
C15 C17 F5 120.0(2) . . ?
C15 C17 C12 118.7(2) . . ?
C19 C18 F10 120.3(3) . . ?
C25 C18 F10 120.3(3) . . ?
C25 C18 C19 119.3(3) . . ?
C18 C19 F6 120.1(3) . . ?
C21 C19 F6 120.2(3) . . ?
C21 C19 C18 119.7(2) . . ?
C16 C20 F7 118.8(2) . . ?
C25 C20 F7 115.9(2) . . ?
C25 C20 C16 125.2(2) . . ?
C16 C21 F4 120.5(2) . . ?
C19 C21 F4 114.9(2) . . ?
C19 C21 C16 124.5(3) . . ?
C14 B22 C14 101.7(3) 2_655 . ?
C16 B22 C14 113.90(12) . . ?
C16 B22 C14 112.51(12) . 2_655 ?
C16 B22 C14 112.51(12) 2_655 . ?
C16 B22 C14 113.90(12) 2_655 2_655 ?
C16 B22 C16 102.7(3) . 2_655 ?
C13 C23 F3 120.4(2) . . ?
C15 C23 F3 119.5(2) . . ?
C15 C23 C13 120.2(2) . . ?
C26 C2 N1 104.4(2) . . ?
C27 C2 N1 103.4(2) . . ?
C27 C2 C26 111.3(2) . . ?
C28 C2 N1 111.5(2) . . ?
C28 C2 C26 113.2(3) . . ?
C28 C2 C27 112.3(2) . . ?
C18 C25 F8 120.2(3) . . ?
C20 C25 F8 121.0(3) . . ?
C20 C25 C18 118.8(3) . . ?
H26a C26 C2 109.5 . . ?
H26b C26 C2 109.5 . . ?
H26b C26 H26a 109.5 . . ?
H26c C26 C2 109.5 . . ?
H26c C26 H26a 109.5 . . ?
H26c C26 H26b 109.5 . . ?
H27a C27 C2 109.5 . . ?
H27b C27 C2 109.5 . . ?
H27b C27 H27a 109.5 . . ?
H27c C27 C2 109.5 . . ?
H27c C27 H27a 109.5 . . ?
H27c C27 H27b 109.5 . . ?
H28a C28 C2 109.5 . . ?
H28b C28 C2 109.5 . . ?
H28b C28 H28a 109.5 . . ?
H28c C28 C2 109.5 . . ?
H28c C28 H28a 109.5 . . ?
H28c C28 H28b 109.5 . . ?
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
F1 C13 1.358(3) . ?
F2 C12 1.365(3) . ?
F3 C23 1.356(3) . ?
F4 C21 1.362(3) . ?
F5 C17 1.345(3) . ?
F6 C19 1.349(3) . ?
F7 C20 1.360(3) . ?
F8 C25 1.346(3) . ?
F9 C15 1.348(3) . ?
F10 C18 1.352(3) . ?
N1 N1 1.216(4) 7_685 ?
N1 H1 0.8800 . ?
N1 C2 1.494(3) . ?
C12 C14 1.395(3) . ?
C12 C17 1.373(4) . ?
C13 C14 1.388(3) . ?
C13 C23 1.379(4) . ?
C14 B22 1.659(4) 2_655 ?
C15 C17 1.376(4) . ?
C15 C23 1.371(4) . ?
C16 C20 1.395(4) . ?
C16 C21 1.384(4) . ?
C16 B22 1.655(4) 2_655 ?
C18 C19 1.366(4) . ?
C18 C25 1.374(4) . ?
C19 C21 1.384(4) . ?
C20 C25 1.378(4) . ?
C2 C26 1.521(4) . ?
C2 C27 1.526(4) . ?
C2 C28 1.517(4) . ?
C26 H26a 0.9800 . ?
C26 H26b 0.9800 . ?
C26 H26c 0.9800 . ?
C27 H27a 0.9800 . ?
C27 H27b 0.9800 . ?
C27 H27c 0.9800 . ?
C28 H28a 0.9800 . ?
C28 H28b 0.9800 . ?
C28 H28c 0.9800 . ?
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
F1 C13 C14 C12 176.9(2) . . . . ?
F1 C13 C14 B22 4.2(3) . . . 2_655 ?
F1 C13 C23 F3 2.5(2) . . . . ?
F1 C13 C23 C15 -177.6(2) . . . . ?
F2 C12 C14 C13 -178.7(2) . . . . ?
F2 C12 C14 B22 -5.3(3) . . . 2_655 ?
F2 C12 C17 F5 -0.3(2) . . . . ?
F2 C12 C17 C15 179.7(2) . . . . ?
F3 C23 C13 C14 -178.6(2) . . . . ?
F3 C23 C15 F9 -0.3(3) . . . . ?
F3 C23 C15 C17 179.8(2) . . . . ?
F4 C21 C16 C20 -177.9(2) . . . . ?
F4 C21 C16 B22 -2.5(3) . . . 2_655 ?
F4 C21 C19 F6 -0.4(2) . . . . ?
F4 C21 C19 C18 180.0(2) . . . . ?
F5 C17 C12 C14 179.4(2) . . . . ?
F5 C17 C15 F9 -0.2(3) . . . . ?
F5 C17 C15 C23 179.7(2) . . . . ?
F6 C19 C18 F10 -0.6(3) . . . . ?
F6 C19 C18 C25 178.8(2) . . . . ?
F6 C19 C21 C16 179.8(2) . . . . ?
F7 C20 C16 C21 178.6(2) . . . . ?
F7 C20 C16 B22 2.8(3) . . . 2_655 ?
F7 C20 C25 F8 1.0(3) . . . . ?
F7 C20 C25 C18 -179.8(2) . . . . ?
F8 C25 C18 F10 -0.7(3) . . . . ?
F8 C25 C18 C19 179.9(2) . . . . ?
F8 C25 C20 C16 -177.6(2) . . . . ?
F9 C15 C17 C12 179.8(2) . . . . ?
F9 C15 C23 C13 179.8(2) . . . . ?
F10 C18 C19 C21 179.1(2) . . . . ?
F10 C18 C25 C20 -179.9(2) . . . . ?
N1 N1 C2 C26 124.3(3) 7_685 . . . ?
N1 N1 C2 C27 -119.1(3) 7_685 . . . ?
N1 N1 C2 C28 1.8(4) 7_685 . . . ?
C12 C14 C13 C23 -1.9(3) . . . . ?
C12 C14 B22 C14 -59.7(3) . . 2_655 2_655 ?
C12 C14 B22 C16 61.6(2) . . 2_655 . ?
C12 C14 B22 C16 178.0(2) . . 2_655 2_655 ?
C12 C17 C15 C23 -0.3(3) . . . . ?
C13 C14 B22 C14 112.6(2) . . 2_655 2_655 ?
C13 C14 B22 C16 -126.1(3) . . 2_655 . ?
C13 C14 B22 C16 -9.7(3) . . 2_655 2_655 ?
C13 C23 C15 C17 -0.1(3) . . . . ?
C14 B22 C16 C20 -59.6(3) 2_655 . . . ?
C14 B22 C16 C20 -174.7(2) . 2_655 . . ?
C14 B22 C16 C21 125.33(19) 2_655 . . . ?
C14 B22 C16 C21 10.2(3) . 2_655 . . ?
C16 C20 C25 C18 1.6(3) . . . . ?
C16 C21 C19 C18 0.1(3) . . . . ?
C16 B22 C16 C20 63.33(18) 2_655 . . . ?
C16 B22 C16 C21 -111.76(17) 2_655 . . . ?
