# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ghuaf1cult_auto
_database_code_depnum_ccdc_archive 'CCDC 2381592'
loop_
_audit_author_name
_audit_author_address
'Herman Ho-Yung Sung'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2024-09-03 deposited with the CCDC.	2025-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-08-30
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H25 B N2 O2'
_chemical_formula_sum            'C14 H25 B N2 O2'
_chemical_formula_weight         264.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H28 B2 N4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.70607(10)
_cell_length_b                   14.11052(14)
_cell_length_c                   11.39150(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.1395(9)
_cell_angle_gamma                90
_cell_volume                     1557.81(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6965
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.4800
_cell_measurement_theta_min      4.9840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9190
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.483
_diffrn_reflns_theta_min         4.994
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00  -7.00   1.00    2.00    --  -41.13 125.00 -60.00   79
  2  ω    -66.00  30.00   1.00    2.00    --  -41.13  40.00-114.00   96
  3  ω   -114.00 -19.00   1.00    2.00    --  -41.13 -57.00  90.00   95
  4  ω     28.00 107.00   1.00    2.00    --  107.01 -94.00 -30.00   79
  5  ω     80.00 170.00   1.00    2.00    --  107.01  30.00-180.00   90
  6  ω    125.00 178.00   1.00    2.00    --  107.01  77.00   0.00   53
  7  ω    121.00 178.00   1.00    2.00    --  107.01  77.00 120.00   57
  8  ω    109.00 178.00   1.00    2.00    --  107.01 111.00  30.00   69
  9  ω     32.00  58.00   1.00    2.00    --  107.01-111.00 150.00   26
 10  ω     64.00 109.00   1.00    2.00    --  107.01-111.00 150.00   45
 11  ω     32.00 107.00   1.00    2.00    --  107.01 -94.00-180.00   75
 12  ω     37.00 133.00   1.00    2.00    --  107.01 -61.00   0.00   96
 13  ω     80.00 175.00   1.00    2.00    --  107.01  30.00  90.00   95
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0152287000
_diffrn_orient_matrix_UB_12      0.0546014000
_diffrn_orient_matrix_UB_13      0.1171689000
_diffrn_orient_matrix_UB_21      0.1580008000
_diffrn_orient_matrix_UB_22      -0.0113044000
_diffrn_orient_matrix_UB_23      0.0005412000
_diffrn_orient_matrix_UB_31      0.0102885000
_diffrn_orient_matrix_UB_32      0.0937461000
_diffrn_orient_matrix_UB_33      -0.0680052000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2933
_reflns_number_total             3124
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.029
_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)+(0.0471P)²+0.5148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0920
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), B1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C21(H21)
2.c X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O1 O 0.10841(8) 0.29784(5) 0.61603(6) 0.02150(18) Uani 1 1 d . . . . .
O2 O 0.15555(7) 0.45491(5) 0.62307(6) 0.01732(18) Uani 1 1 d . . . . .
N1 N 0.32085(9) 0.54109(6) 0.85086(7) 0.0178(2) Uani 1 1 d . . . . .
N2 N 0.45276(9) 0.41932(6) 0.85672(7) 0.0182(2) Uani 1 1 d . . . . .
C1 C 0.31899(10) 0.44542(7) 0.86003(8) 0.0164(2) Uani 1 1 d . . . . .
C2 C 0.45388(11) 0.57424(8) 0.84172(9) 0.0209(2) Uani 1 1 d . . . . .
H2 H 0.4815 0.6384 0.8340 0.025 Uiso 1 1 calc R U . . .
C3 C 0.53653(11) 0.49756(8) 0.84586(9) 0.0217(2) Uani 1 1 d . . . . .
H3 H 0.6341 0.4973 0.8420 0.026 Uiso 1 1 calc R U . . .
C4 C 0.19982(11) 0.60304(7) 0.84727(10) 0.0232(2) Uani 1 1 d . . . . .
H4A H 0.1539 0.6011 0.7685 0.035 Uiso 1 1 calc R U . . .
H4B H 0.2288 0.6681 0.8658 0.035 Uiso 1 1 calc R U . . .
H4C H 0.1357 0.5814 0.9051 0.035 Uiso 1 1 calc R U . . .
C5 C 0.50551(11) 0.32238(8) 0.86574(10) 0.0258(2) Uani 1 1 d . . . . .
H5A H 0.6058 0.3229 0.8593 0.039 Uiso 1 1 calc R U . . .
H5B H 0.4625 0.2839 0.8022 0.039 Uiso 1 1 calc R U . . .
H5C H 0.4836 0.2954 0.9418 0.039 Uiso 1 1 calc R U . . .
C11 C 0.05496(10) 0.38911(7) 0.78667(8) 0.0176(2) Uani 1 1 d . . . . .
H11 H 0.0189 0.4552 0.7926 0.021 Uiso 1 1 calc R U . . .
C12 C 0.10584(9) 0.37338(7) 0.66733(8) 0.0161(2) Uani 1 1 d . . . . .
C13 C -0.05874(11) 0.31841(8) 0.81372(9) 0.0253(2) Uani 1 1 d . . . . .
H13A H -0.1312 0.3199 0.7503 0.038 Uiso 1 1 calc R U . . .
H13B H -0.0982 0.3356 0.8882 0.038 Uiso 1 1 calc R U . . .
H13C H -0.0196 0.2545 0.8200 0.038 Uiso 1 1 calc R U . . .
C14 C 0.23443(10) 0.45662(7) 0.51640(9) 0.0181(2) Uani 1 1 d . . . . .
C15 C 0.15269(11) 0.41581(8) 0.41034(9) 0.0233(2) Uani 1 1 d . . . . .
H15A H 0.1481 0.3467 0.4177 0.035 Uiso 1 1 calc R U . . .
H15B H 0.1983 0.4324 0.3385 0.035 Uiso 1 1 calc R U . . .
H15C H 0.0591 0.4421 0.4066 0.035 Uiso 1 1 calc R U . . .
C16 C 0.25736(12) 0.56224(8) 0.49906(10) 0.0243(2) Uani 1 1 d . . . . .
H16A H 0.1681 0.5940 0.4859 0.036 Uiso 1 1 calc R U . . .
H16B H 0.3129 0.5721 0.4308 0.036 Uiso 1 1 calc R U . . .
H16C H 0.3059 0.5886 0.5693 0.036 Uiso 1 1 calc R U . . .
C17 C 0.37017(11) 0.40458(8) 0.54079(10) 0.0240(2) Uani 1 1 d . . . . .
H17A H 0.4207 0.4335 0.6085 0.036 Uiso 1 1 calc R U . . .
H17B H 0.4257 0.4088 0.4717 0.036 Uiso 1 1 calc R U . . .
H17C H 0.3516 0.3379 0.5579 0.036 Uiso 1 1 calc R U . . .
C21 C 0.14743(10) 0.38915(7) 1.01571(9) 0.0208(2) Uani 1 1 d . . . . .
H21 H 0.1176 0.4505 1.0375 0.025 Uiso 1 1 calc R U . . .
C22 C 0.15021(13) 0.32217(9) 1.09734(10) 0.0299(3) Uani 1 1 d . . . . .
H22A H 0.1794 0.2599 1.0790 0.036 Uiso 1 1 calc R U . . .
H22B H 0.1230 0.3364 1.1742 0.036 Uiso 1 1 calc R U . . .
B1 B 0.19063(11) 0.37463(8) 0.88237(10) 0.0175(2) Uani 1 1 d . . . . .
H1 H 0.2243 0.3081 0.8746 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C12 1.2164(12) . ?
O2 C12 1.3554(12) . ?
O2 C14 1.4715(11) . ?
N1 C1 1.3543(13) . ?
N1 C2 1.3826(13) . ?
N1 C4 1.4630(13) . ?
N2 C1 1.3521(13) . ?
N2 C3 1.3808(13) . ?
N2 C5 1.4621(13) . ?
C1 B1 1.6276(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3461(15) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.4882(13) . ?
C11 C13 1.5314(14) . ?
C11 B1 1.6754(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5218(14) . ?
C14 C16 1.5214(14) . ?
C14 C17 1.5206(14) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.3251(16) . ?
C21 B1 1.6108(15) . ?
C22 H22A 0.9500 . ?
C22 H22B 0.9500 . ?
B1 H1 1.0000 . ?

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
C12 O2 C14 122.21(7) . . ?
C1 N1 C2 111.06(8) . . ?
C1 N1 C4 125.71(8) . . ?
C2 N1 C4 123.20(9) . . ?
C1 N2 C3 110.84(8) . . ?
C1 N2 C5 125.87(9) . . ?
C3 N2 C5 123.27(9) . . ?
N1 C1 B1 129.59(9) . . ?
N2 C1 N1 104.63(8) . . ?
N2 C1 B1 125.57(9) . . ?
N1 C2 H2 126.8 . . ?
C3 C2 N1 106.42(9) . . ?
C3 C2 H2 126.8 . . ?
N2 C3 H3 126.5 . . ?
C2 C3 N2 107.04(9) . . ?
C2 C3 H3 126.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 C11 H11 109.6 . . ?
C12 C11 C13 111.43(8) . . ?
C12 C11 B1 106.73(8) . . ?
C13 C11 H11 109.6 . . ?
C13 C11 B1 109.82(8) . . ?
B1 C11 H11 109.6 . . ?
O1 C12 O2 123.22(9) . . ?
O1 C12 C11 125.88(9) . . ?
O2 C12 C11 110.85(8) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 112.16(8) . . ?
O2 C14 C16 102.11(8) . . ?
O2 C14 C17 109.02(8) . . ?
C16 C14 C15 109.96(9) . . ?
C17 C14 C15 111.79(9) . . ?
C17 C14 C16 111.43(9) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 H21 117.5 . . ?
C22 C21 B1 125.08(10) . . ?
B1 C21 H21 117.5 . . ?
C21 C22 H22A 120.0 . . ?
C21 C22 H22B 120.0 . . ?
H22A C22 H22B 120.0 . . ?
C1 B1 C11 113.86(8) . . ?
C1 B1 H1 107.8 . . ?
C11 B1 H1 107.8 . . ?
C21 B1 C1 108.08(8) . . ?
C21 B1 C11 111.23(8) . . ?
C21 B1 H1 107.8 . . ?

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
N1 C1 B1 C11 53.79(13) . . . . ?
N1 C1 B1 C21 -70.33(12) . . . . ?
N1 C2 C3 N2 0.33(11) . . . . ?
N2 C1 B1 C11 -132.38(10) . . . . ?
N2 C1 B1 C21 103.49(11) . . . . ?
C1 N1 C2 C3 -0.29(11) . . . . ?
C1 N2 C3 C2 -0.28(11) . . . . ?
C2 N1 C1 N2 0.11(11) . . . . ?
C2 N1 C1 B1 174.92(9) . . . . ?
C3 N2 C1 N1 0.10(11) . . . . ?
C3 N2 C1 B1 -174.98(9) . . . . ?
C4 N1 C1 N2 178.39(9) . . . . ?
C4 N1 C1 B1 -6.80(16) . . . . ?
C4 N1 C2 C3 -178.62(9) . . . . ?
C5 N2 C1 N1 178.86(9) . . . . ?
C5 N2 C1 B1 3.78(15) . . . . ?
C5 N2 C3 C2 -179.08(9) . . . . ?
C12 O2 C14 C15 58.64(11) . . . . ?
C12 O2 C14 C16 176.31(8) . . . . ?
C12 O2 C14 C17 -65.71(11) . . . . ?
C12 C11 B1 C1 58.10(10) . . . . ?
C12 C11 B1 C21 -179.49(8) . . . . ?
C13 C11 C12 O1 -29.82(14) . . . . ?
C13 C11 C12 O2 152.68(8) . . . . ?
C13 C11 B1 C1 179.02(8) . . . . ?
C13 C11 B1 C21 -58.56(11) . . . . ?
C14 O2 C12 O1 -8.68(14) . . . . ?
C14 O2 C12 C11 168.90(8) . . . . ?
C22 C21 B1 C1 -119.46(12) . . . . ?
C22 C21 B1 C11 114.85(12) . . . . ?
B1 C11 C12 O1 90.07(11) . . . . ?
B1 C11 C12 O2 -87.43(9) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.220
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ghuaf4_cu100k_auto
_database_code_depnum_ccdc_archive 'CCDC 2381595'
loop_
_audit_author_name
_audit_author_address
'Herman Ho-Yung Sung'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2024-09-03 deposited with the CCDC.	2025-06-13 downloaded from the CCDC.
;
_audit_creation_date             2024-06-03
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C43 H37 B F6 N2 Ni P2, 0.375(C6 H14), 0.125(C6 H12)'
_chemical_formula_sum            'C46 H43.75 B F6 N2 Ni P2'
_chemical_formula_weight         870.04
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   12.01864(11)
_cell_length_b                   11.91416(9)
_cell_length_c                   28.8690(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.2828(8)
_cell_angle_gamma                90
_cell_volume                     4130.53(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7886
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      73.1340
_cell_measurement_theta_min      4.0180
_shelx_estimated_absorpt_T_max   0.829
_shelx_estimated_absorpt_T_min   0.759
_exptl_absorpt_coefficient_mu    1.943
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1803
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12865
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.991
_diffrn_reflns_theta_min         3.681
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.50  42.00   0.75   16.00    --   36.13  77.00  30.00   58
  2  ω    -37.00  72.50   0.75   16.00    --   36.13 -37.00   0.00  146
  3  ω      0.00 119.25   0.75   16.00    --   36.13  57.00-150.00  159
  4  ω     25.00 146.50   0.75   48.00    --  109.64 -61.00  90.00  162
  5  ω    103.00 172.00   0.75   48.00    --  109.64  77.00  90.00   92
  6  ω    132.00 172.50   0.75   48.00    --  109.64 111.00 120.00   54
  7  ω    103.00 170.50   0.75   48.00    --  109.64  77.00-150.00   90
  8  ω     74.00 176.00   0.75   48.00    --  109.64  30.00-180.00  136
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0650395000
_diffrn_orient_matrix_UB_12      0.1114478000
_diffrn_orient_matrix_UB_13      0.0020523000
_diffrn_orient_matrix_UB_21      0.0653592000
_diffrn_orient_matrix_UB_22      -0.0365910000
_diffrn_orient_matrix_UB_23      -0.0423144000
_diffrn_orient_matrix_UB_31      -0.0891542000
_diffrn_orient_matrix_UB_32      0.0543318000
_diffrn_orient_matrix_UB_33      -0.0325563000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6998
_reflns_number_total             7963
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         7963
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.032
_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)+(0.0497P)²+2.8215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H1SA,H1SB,H1SC} of C1S, All C(H,H) groups
 At 1.5 times of:
  {H6A,H6B,H6C} of C6, {H7A,H7B,H7C} of C7
2. Restrained distances
 C11S-C12S = C13S-C12S
 1.52 with sigma of 0.01
 C11S_$1-C13S
 1.52 with sigma of 0.01
 C11S-C13S
 2.45 with sigma of 0.02
 F4A-C44 \\sim F4-C44
 with sigma of 0.02
 F3-C34 \\sim F3A-C34
 with sigma of 0.02
 F2A-C24 \\sim F2-C24
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12S) \\sim Ueq, Uanis(C13S) \\sim Ueq, Uanis(C11S) \\sim Ueq: with sigma
of 0.003 and sigma for terminal atoms of 0.008
Uanis(F4A) \\sim Ueq, Uanis(F4) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.008
Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.008
Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq: with sigma of 0.003 and sigma for
terminal atoms of 0.008
4. Rigid body (RIGU) restrains
 C11S, C12S, C13S
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: F2(0.5) F2A(0.5) F3(0.5) F3A(0.5) F4(0.5) F4A(0.5) C1S(0.75)
 H1SA(0.75) H1SB(0.75) H1SC(0.75) C2S(0.75) H2SA(0.75) H2SB(0.75) C3S(0.75)
 H3SA(0.75) H3SB(0.75) C11S(0.25) H11A(0.25) H11B(0.25) C12S(0.25) H12A(0.25)
 H12B(0.25) C13S(0.25) H13A(0.25) H13B(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C2S(H2SA,H2SB), C3S(H3SA,H3SB), C11S(H11A,H11B), C12S(H12A,H12B), C13S(H13A,
 H13B)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C23(H23),
 C25(H25), C26(H26), C32(H32), C33(H33), C35(H35), C36(H36), C42(H42), C43(H43),
  C45(H45), C46(H46), C52(H52), C53(H53), C55(H55), C56(H56), C62(H62),
 C63(H63), C65(H65), C66(H66)
6.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C1S(H1SA,H1SB,H1SC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Ni1 Ni 0.39407(2) 0.19016(2) 0.10752(2) 0.01487(8) Uani 1 1 d . . . . .
H1A H 0.426(2) 0.139(2) 0.0567(8) 0.033(6) Uiso 1 1 d . . . . .
P1 P 0.23752(3) 0.11565(3) 0.12721(2) 0.01492(10) Uani 1 1 d . . . . .
P2 P 0.53414(4) 0.15807(4) 0.15336(2) 0.01555(10) Uani 1 1 d . . . . .
F1 F -0.11201(12) 0.17362(13) -0.02314(5) 0.0464(4) Uani 1 1 d . . . . .
F2 F 0.0008(18) 0.3509(15) 0.2762(7) 0.037(3) Uani 0.5 1 d D U P A 1
F2A F 0.0120(18) 0.3686(14) 0.2747(7) 0.031(2) Uani 0.5 1 d D U P A 2
F3 F 0.220(2) -0.3750(9) 0.1686(6) 0.041(3) Uani 0.5 1 d D U P B 1
F3A F 0.2182(19) -0.3698(8) 0.1779(6) 0.036(2) Uani 0.5 1 d D U P B 2
F4 F 0.3992(12) 0.1019(13) 0.3489(4) 0.034(2) Uani 0.5 1 d D U P C 1
F4A F 0.4200(12) 0.0837(13) 0.3503(3) 0.0308(18) Uani 0.5 1 d D U P C 2
F5 F 0.81745(13) -0.23640(13) 0.10969(5) 0.0518(4) Uani 1 1 d . . . . .
F6 F 0.88774(12) 0.51004(12) 0.16659(5) 0.0461(3) Uani 1 1 d . . . . .
N1 N 0.59223(13) 0.20718(13) -0.01005(5) 0.0196(3) Uani 1 1 d . . . . .
N2 N 0.49061(13) 0.34879(13) -0.03009(5) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.33950(16) 0.30795(15) 0.06266(6) 0.0205(4) Uani 1 1 d . . . . .
H1 H 0.2551(19) 0.3208(18) 0.0606(8) 0.021(5) Uiso 1 1 d . . . . .
C2 C 0.40101(17) 0.36594(15) 0.09651(7) 0.0232(4) Uani 1 1 d . . . . .
H2A H 0.3568(18) 0.4150(18) 0.1167(7) 0.020(5) Uiso 1 1 d . . . . .
H2B H 0.483(2) 0.378(2) 0.0932(9) 0.036(7) Uiso 1 1 d . . . . .
C3 C 0.49613(15) 0.25963(14) -0.00084(6) 0.0170(3) Uani 1 1 d . . . . .
C4 C 0.64595(17) 0.26255(18) -0.04517(7) 0.0273(4) Uani 1 1 d . . . . .
H4 H 0.714616 0.241829 -0.057955 0.033 Uiso 1 1 calc R U . . .
C5 C 0.58219(17) 0.35090(17) -0.05753(7) 0.0277(4) Uani 1 1 d . . . . .
H5 H 0.597177 0.404704 -0.080755 0.033 Uiso 1 1 calc R U . . .
C6 C 0.63109(16) 0.10136(16) 0.01069(7) 0.0244(4) Uani 1 1 d . . . . .
H6A H 0.605507 0.038581 -0.008910 0.037 Uiso 1 1 calc R U . . .
H6B H 0.601139 0.093354 0.041601 0.037 Uiso 1 1 calc R U . . .
H6C H 0.712644 0.101314 0.013273 0.037 Uiso 1 1 calc R U . . .
C7 C 0.39560(17) 0.42472(16) -0.03533(7) 0.0249(4) Uani 1 1 d . . . . .
H7A H 0.332468 0.384794 -0.050206 0.037 Uiso 1 1 calc R U . . .
H7B H 0.415599 0.488852 -0.054562 0.037 Uiso 1 1 calc R U . . .
H7C H 0.374947 0.451490 -0.004746 0.037 Uiso 1 1 calc R U . . .
C11 C 0.12200(14) 0.12939(14) 0.08358(6) 0.0174(3) Uani 1 1 d . . . . .
C12 C 0.01653(16) 0.17101(17) 0.09242(7) 0.0267(4) Uani 1 1 d . . . . .
H12 H -0.001169 0.189926 0.123237 0.032 Uiso 1 1 calc R U . . .
C13 C -0.06321(18) 0.18515(19) 0.05651(8) 0.0332(5) Uani 1 1 d . . . . .
H13 H -0.135527 0.212359 0.062503 0.040 Uiso 1 1 calc R U . . .
C14 C -0.03456(18) 0.15875(18) 0.01224(7) 0.0305(4) Uani 1 1 d . . . . .
C15 C 0.06764(17) 0.11630(19) 0.00186(7) 0.0290(4) Uani 1 1 d . . . . .
H15 H 0.084582 0.097902 -0.029088 0.035 Uiso 1 1 calc R U . . .
C16 C 0.14514(15) 0.10125(17) 0.03807(6) 0.0235(4) Uani 1 1 d . . . . .
H16 H 0.216042 0.070911 0.031758 0.028 Uiso 1 1 calc R U . . .
C21 C 0.17066(15) 0.18320(15) 0.17625(6) 0.0182(3) Uani 1 1 d . . . . .
C22 C 0.11144(16) 0.12694(16) 0.20966(6) 0.0237(4) Uani 1 1 d . . . . .
H22 H 0.108277 0.047273 0.209282 0.028 Uiso 1 1 calc R U . . .
C23 C 0.05661(18) 0.18633(18) 0.24374(7) 0.0303(4) Uani 1 1 d . . . . .
H23 H 0.016751 0.148112 0.266731 0.036 Uiso 1 1 calc R U . . .
C24 C 0.06196(17) 0.30131(18) 0.24307(7) 0.0281(4) Uani 1 1 d D . . . .
C25 C 0.12034(17) 0.36054(17) 0.21103(7) 0.0293(4) Uani 1 1 d . . . . .
H25 H 0.123088 0.440209 0.211747 0.035 Uiso 1 1 calc R U . . .
C26 C 0.17499(16) 0.30026(16) 0.17771(7) 0.0241(4) Uani 1 1 d . . . . .
H26 H 0.216223 0.339417 0.155427 0.029 Uiso 1 1 calc R U . . .
C31 C 0.22596(15) -0.03472(15) 0.14156(6) 0.0176(3) Uani 1 1 d . . . . .
C32 C 0.13319(15) -0.10026(16) 0.12930(6) 0.0216(4) Uani 1 1 d . . . . .
H32 H 0.071095 -0.066485 0.113395 0.026 Uiso 1 1 calc R U . . .
C33 C 0.12981(17) -0.21427(17) 0.13992(7) 0.0269(4) Uani 1 1 d . . . . .
H33 H 0.066144 -0.258334 0.131731 0.032 Uiso 1 1 calc R U . . .
C34 C 0.22145(18) -0.26132(16) 0.16265(7) 0.0276(4) Uani 1 1 d D . . . .
C35 C 0.31535(17) -0.20037(16) 0.17514(6) 0.0247(4) Uani 1 1 d . . . . .
H35 H 0.377561 -0.235139 0.190579 0.030 Uiso 1 1 calc R U . . .
C36 C 0.31649(16) -0.08661(15) 0.16453(6) 0.0207(4) Uani 1 1 d . . . . .
H36 H 0.380325 -0.043183 0.173109 0.025 Uiso 1 1 calc R U . . .
C41 C 0.50282(15) 0.13380(15) 0.21468(6) 0.0193(3) Uani 1 1 d . . . . .
C42 C 0.54818(17) 0.04759(16) 0.24214(6) 0.0260(4) Uani 1 1 d . . . . .
H42 H 0.601601 -0.001645 0.229757 0.031 Uiso 1 1 calc R U . . .
C43 C 0.5157(2) 0.03302(17) 0.28768(7) 0.0316(5) Uani 1 1 d . . . . .
H43 H 0.545593 -0.026505 0.306216 0.038 Uiso 1 1 calc R U . . .
C44 C 0.44015(18) 0.10614(18) 0.30510(6) 0.0297(4) Uani 1 1 d D . . . .
C45 C 0.39357(17) 0.19271(18) 0.27946(7) 0.0276(4) Uani 1 1 d . . . . .
H45 H 0.341349 0.242291 0.292461 0.033 Uiso 1 1 calc R U . . .
C46 C 0.42520(16) 0.20547(16) 0.23397(6) 0.0226(4) Uani 1 1 d . . . . .
H46 H 0.393320 0.264245 0.215591 0.027 Uiso 1 1 calc R U . . .
C51 C 0.62483(15) 0.03752(15) 0.14128(6) 0.0196(3) Uani 1 1 d . . . . .
C52 C 0.73713(17) 0.03218(18) 0.15566(8) 0.0300(4) Uani 1 1 d . . . . .
H52 H 0.769331 0.092655 0.172948 0.036 Uiso 1 1 calc R U . . .
C53 C 0.80270(18) -0.0599(2) 0.14518(8) 0.0345(5) Uani 1 1 d . . . . .
H53 H 0.879067 -0.062935 0.154939 0.041 Uiso 1 1 calc R U . . .
C54 C 0.75367(19) -0.14646(18) 0.12025(7) 0.0328(5) Uani 1 1 d . . . . .
C55 C 0.64375(19) -0.14553(17) 0.10550(7) 0.0302(4) Uani 1 1 d . . . . .
H55 H 0.612241 -0.207003 0.088626 0.036 Uiso 1 1 calc R U . . .
C56 C 0.57950(16) -0.05227(16) 0.11587(6) 0.0224(4) Uani 1 1 d . . . . .
H56 H 0.503543 -0.049719 0.105479 0.027 Uiso 1 1 calc R U . . .
C61 C 0.64236(15) 0.26751(15) 0.15950(6) 0.0193(3) Uani 1 1 d . . . . .
C62 C 0.68324(17) 0.30887(18) 0.20187(7) 0.0286(4) Uani 1 1 d . . . . .
H62 H 0.653895 0.280721 0.229649 0.034 Uiso 1 1 calc R U . . .
C63 C 0.76608(19) 0.3905(2) 0.20462(8) 0.0363(5) Uani 1 1 d . . . . .
H63 H 0.793295 0.418209 0.233771 0.044 Uiso 1 1 calc R U . . .
C64 C 0.80732(17) 0.42979(18) 0.16414(8) 0.0309(4) Uani 1 1 d . . . . .
C65 C 0.77018(16) 0.39183(16) 0.12110(7) 0.0264(4) Uani 1 1 d . . . . .
H65 H 0.800698 0.420139 0.093583 0.032 Uiso 1 1 calc R U . . .
C66 C 0.68691(15) 0.31105(15) 0.11920(6) 0.0217(4) Uani 1 1 d . . . . .
H66 H 0.659513 0.284692 0.089856 0.026 Uiso 1 1 calc R U . . .
B1 B 0.39425(17) 0.21968(18) 0.02935(7) 0.0199(4) Uani 1 1 d . . . . .
H1B H 0.333(2) 0.183(2) 0.0029(8) 0.031(6) Uiso 1 1 d . . . . .
C1S C 0.0743(3) 0.4941(3) 0.08694(17) 0.0614(11) Uani 0.75 1 d . . P D 1
H1SA H 0.146830 0.496298 0.072646 0.074 Uiso 0.75 1 calc R U P D 1
H1SB H 0.046644 0.416688 0.087005 0.074 Uiso 0.75 1 calc R U P D 1
H1SC H 0.082104 0.521640 0.118887 0.074 Uiso 0.75 1 calc R U P D 1
C2S C -0.0069(5) 0.5673(4) 0.05970(17) 0.0708(12) Uani 0.75 1 d . . P D 1
H2SA H -0.070591 0.584773 0.079189 0.085 Uiso 0.75 1 calc R U P D 1
H2SB H 0.030104 0.638936 0.052311 0.085 Uiso 0.75 1 calc R U P D 1
C3S C -0.0497(5) 0.5143(5) 0.0158(2) 0.0853(17) Uani 0.75 1 d . . P D 1
H3SA H -0.101744 0.566260 -0.000793 0.102 Uiso 0.75 1 calc R U P D 1
H3SB H -0.090794 0.444788 0.022872 0.102 Uiso 0.75 1 calc R U P D 1
C11S C 0.0482(8) 0.5700(11) 0.0391(4) 0.055(2) Uani 0.25 1 d D U P E 2
H11A H 0.073646 0.645402 0.049282 0.066 Uiso 0.25 1 calc R U P E 2
H11B H 0.056182 0.518417 0.065874 0.066 Uiso 0.25 1 calc R U P E 2
C12S C -0.0760(9) 0.5757(11) 0.0221(5) 0.065(3) Uani 0.25 1 d D U P E 2
H12A H -0.122386 0.590548 0.049034 0.078 Uiso 0.25 1 calc R U P E 2
H12B H -0.085988 0.639486 0.000333 0.078 Uiso 0.25 1 calc R U P E 2
C13S C -0.1169(10) 0.4696(11) -0.0017(4) 0.070(3) Uani 0.25 1 d D U P E 2
H13A H -0.121053 0.409466 0.021798 0.084 Uiso 0.25 1 calc R U P E 2
H13B H -0.193340 0.482823 -0.014603 0.084 Uiso 0.25 1 calc R U P E 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Ni1 H1A 1.65(2) . ?
Ni1 P1 2.1763(5) . ?
Ni1 P2 2.1340(5) . ?
Ni1 C1 2.0023(18) . ?
Ni1 C2 2.1204(18) . ?
Ni1 B1 2.2841(19) . ?
P1 C11 1.8444(18) . ?
P1 C21 1.8407(18) . ?
P1 C31 1.8452(18) . ?
P2 C41 1.8473(18) . ?
P2 C51 1.8447(18) . ?
P2 C61 1.8452(19) . ?
F1 C14 1.366(2) . ?
F2 C24 1.364(10) . ?
F2A C24 1.372(9) . ?
F3 C34 1.366(10) . ?
F3A C34 1.367(9) . ?
F4 C44 1.377(10) . ?
F4A C44 1.364(9) . ?
F5 C54 1.359(2) . ?
F6 C64 1.359(2) . ?
N1 C3 1.349(2) . ?
N1 C4 1.390(2) . ?
N1 C6 1.464(2) . ?
N2 C3 1.357(2) . ?
N2 C5 1.382(2) . ?
N2 C7 1.460(2) . ?
C1 H1 1.03(2) . ?
C1 C2 1.386(3) . ?
C1 B1 1.586(3) . ?
C2 H2A 0.99(2) . ?
C2 H2B 1.00(3) . ?
C3 B1 1.603(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.342(3) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 C12 1.394(3) . ?
C11 C16 1.395(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(3) . ?
C14 C15 1.372(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9500 . ?
C21 C22 1.393(2) . ?
C21 C26 1.396(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.398(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.371(3) . ?
C24 C25 1.377(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(3) . ?
C26 H26 0.9500 . ?
C31 C32 1.395(3) . ?
C31 C36 1.396(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.394(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.378(3) . ?
C34 C35 1.378(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.390(3) . ?
C36 H36 0.9500 . ?
C41 C42 1.395(3) . ?
C41 C46 1.397(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.397(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.369(3) . ?
C44 C45 1.375(3) . ?
C45 H45 0.9500 . ?
C45 C46 1.390(3) . ?
C46 H46 0.9500 . ?
C51 C52 1.398(3) . ?
C51 C56 1.395(3) . ?
C52 H52 0.9500 . ?
C52 C53 1.391(3) . ?
C53 H53 0.9500 . ?
C53 C54 1.377(3) . ?
C54 C55 1.372(3) . ?
C55 H55 0.9500 . ?
C55 C56 1.393(3) . ?
C56 H56 0.9500 . ?
C61 C62 1.390(3) . ?
C61 C66 1.400(3) . ?
C62 H62 0.9500 . ?
C62 C63 1.392(3) . ?
C63 H63 0.9500 . ?
C63 C64 1.370(3) . ?
C64 C65 1.380(3) . ?
C65 H65 0.9500 . ?
C65 C66 1.388(3) . ?
C66 H66 0.9500 . ?
B1 H1A 1.30(2) . ?
B1 H1B 1.12(2) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C1S C2S 1.506(6) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C2S C3S 1.489(7) . ?
C3S C3S 1.568(10) 3_565 ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C11S H11A 0.9900 . ?
C11S H11B 0.9900 . ?
C11S C12S 1.554(9) . ?
C11S C13S 1.462(9) 3_565 ?
C12S H12A 0.9900 . ?
C12S H12B 0.9900 . ?
C12S C13S 1.512(9) . ?
C13S H13A 0.9900 . ?
C13S H13B 0.9900 . ?

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
P1 Ni1 H1A 108.4(8) . . ?
P1 Ni1 B1 110.84(6) . . ?
P2 Ni1 H1A 106.1(9) . . ?
P2 Ni1 P1 115.71(2) . . ?
P2 Ni1 B1 127.48(5) . . ?
C1 Ni1 H1A 76.6(9) . . ?
C1 Ni1 P1 100.98(6) . . ?
C1 Ni1 P2 139.17(6) . . ?
C1 Ni1 C2 39.16(8) . . ?
C1 Ni1 B1 42.79(7) . . ?
C2 Ni1 H1A 102.9(8) . . ?
C2 Ni1 P1 118.79(6) . . ?
C2 Ni1 P2 103.60(6) . . ?
C2 Ni1 B1 72.43(8) . . ?
B1 Ni1 H1A 33.9(8) . . ?
C11 P1 Ni1 114.87(6) . . ?
C11 P1 C31 100.26(8) . . ?
C21 P1 Ni1 115.53(6) . . ?
C21 P1 C11 98.43(8) . . ?
C21 P1 C31 102.29(8) . . ?
C31 P1 Ni1 121.89(6) . . ?
C41 P2 Ni1 115.88(6) . . ?
C51 P2 Ni1 118.67(6) . . ?
C51 P2 C41 101.76(8) . . ?
C51 P2 C61 98.56(8) . . ?
C61 P2 Ni1 117.94(6) . . ?
C61 P2 C41 100.86(8) . . ?
C3 N1 C4 110.50(15) . . ?
C3 N1 C6 125.45(15) . . ?
C4 N1 C6 123.85(16) . . ?
C3 N2 C5 110.54(16) . . ?
C3 N2 C7 124.62(15) . . ?
C5 N2 C7 124.53(16) . . ?
Ni1 C1 H1 116.1(12) . . ?
C2 C1 Ni1 75.02(11) . . ?
C2 C1 H1 117.7(12) . . ?
C2 C1 B1 122.38(17) . . ?
B1 C1 Ni1 78.13(10) . . ?
B1 C1 H1 119.9(12) . . ?
Ni1 C2 H2A 117.9(12) . . ?
Ni1 C2 H2B 101.8(15) . . ?
C1 C2 Ni1 65.82(10) . . ?
C1 C2 H2A 115.1(13) . . ?
C1 C2 H2B 120.2(15) . . ?
H2A C2 H2B 121.3(19) . . ?
N1 C3 N2 105.13(15) . . ?
N1 C3 B1 130.40(16) . . ?
N2 C3 B1 123.45(16) . . ?
N1 C4 H4 126.6 . . ?
C5 C4 N1 106.82(17) . . ?
C5 C4 H4 126.6 . . ?
N2 C5 H5 126.5 . . ?
C4 C5 N2 107.02(17) . . ?
C4 C5 H5 126.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C12 C11 P1 124.87(14) . . ?
C12 C11 C16 118.35(17) . . ?
C16 C11 P1 116.68(13) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.67(18) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.30(19) . . ?
C14 C13 H13 120.8 . . ?
F1 C14 C13 118.53(19) . . ?
F1 C14 C15 118.28(19) . . ?
C15 C14 C13 123.19(19) . . ?
C14 C15 H15 121.2 . . ?
C14 C15 C16 117.66(18) . . ?
C16 C15 H15 121.2 . . ?
C11 C16 H16 119.1 . . ?
C15 C16 C11 121.80(18) . . ?
C15 C16 H16 119.1 . . ?
C22 C21 P1 124.95(14) . . ?
C22 C21 C26 118.62(17) . . ?
C26 C21 P1 116.31(13) . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.79(18) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.9 . . ?
C24 C23 C22 118.15(18) . . ?
C24 C23 H23 120.9 . . ?
F2 C24 C23 113.3(8) . . ?
F2 C24 C25 123.5(8) . . ?
F2A C24 C25 113.3(8) . . ?
C23 C24 F2A 123.5(8) . . ?
C23 C24 C25 123.14(18) . . ?
C24 C25 H25 121.0 . . ?
C24 C25 C26 117.94(19) . . ?
C26 C25 H25 121.0 . . ?
C21 C26 H26 119.3 . . ?
C25 C26 C21 121.35(18) . . ?
C25 C26 H26 119.3 . . ?
C32 C31 P1 123.58(14) . . ?
C32 C31 C36 118.19(16) . . ?
C36 C31 P1 118.19(14) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 C31 121.32(18) . . ?
C33 C32 H32 119.3 . . ?
C32 C33 H33 120.9 . . ?
C34 C33 C32 118.12(18) . . ?
C34 C33 H33 120.9 . . ?
F3 C34 C33 116.7(10) . . ?
F3 C34 C35 120.3(10) . . ?
F3A C34 C33 120.4(9) . . ?
F3A C34 C35 116.6(9) . . ?
C35 C34 C33 122.75(18) . . ?
C34 C35 H35 120.9 . . ?
C34 C35 C36 118.12(18) . . ?
C36 C35 H35 120.9 . . ?
C31 C36 H36 119.3 . . ?
C35 C36 C31 121.49(18) . . ?
C35 C36 H36 119.3 . . ?
C42 C41 P2 124.74(14) . . ?
C42 C41 C46 118.41(17) . . ?
C46 C41 P2 116.82(14) . . ?
C41 C42 H42 119.7 . . ?
C41 C42 C43 120.59(19) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 H43 120.6 . . ?
C44 C43 C42 118.73(19) . . ?
C44 C43 H43 120.6 . . ?
F4A C44 C43 111.9(5) . . ?
F4A C44 C45 125.3(6) . . ?
C43 C44 F4 125.5(6) . . ?
C43 C44 C45 122.79(18) . . ?
C45 C44 F4 111.7(5) . . ?
C44 C45 H45 121.0 . . ?
C44 C45 C46 118.01(19) . . ?
C46 C45 H45 121.0 . . ?
C41 C46 H46 119.3 . . ?
C45 C46 C41 121.46(18) . . ?
C45 C46 H46 119.3 . . ?
C52 C51 P2 123.38(15) . . ?
C56 C51 P2 118.35(14) . . ?
C56 C51 C52 118.26(17) . . ?
C51 C52 H52 119.3 . . ?
C53 C52 C51 121.3(2) . . ?
C53 C52 H52 119.3 . . ?
C52 C53 H53 121.0 . . ?
C54 C53 C52 118.0(2) . . ?
C54 C53 H53 121.0 . . ?
F5 C54 C53 118.3(2) . . ?
F5 C54 C55 118.8(2) . . ?
C55 C54 C53 122.89(19) . . ?
C54 C55 H55 120.8 . . ?
C54 C55 C56 118.4(2) . . ?
C56 C55 H55 120.8 . . ?
C51 C56 H56 119.5 . . ?
C55 C56 C51 121.09(18) . . ?
C55 C56 H56 119.5 . . ?
C62 C61 P2 123.92(15) . . ?
C62 C61 C66 117.80(17) . . ?
C66 C61 P2 118.28(13) . . ?
C61 C62 H62 119.2 . . ?
C61 C62 C63 121.65(19) . . ?
C63 C62 H62 119.2 . . ?
C62 C63 H63 120.9 . . ?
C64 C63 C62 118.20(19) . . ?
C64 C63 H63 120.9 . . ?
F6 C64 C63 118.47(19) . . ?
F6 C64 C65 118.76(19) . . ?
C63 C64 C65 122.76(19) . . ?
C64 C65 H65 121.0 . . ?
C64 C65 C66 118.02(19) . . ?
C66 C65 H65 121.0 . . ?
C61 C66 H66 119.2 . . ?
C65 C66 C61 121.56(18) . . ?
C65 C66 H66 119.2 . . ?
Ni1 B1 H1A 45.2(11) . . ?
Ni1 B1 H1B 125.9(12) . . ?
H1A B1 H1B 107.2(16) . . ?
C1 B1 Ni1 59.08(9) . . ?
C1 B1 H1A 104.2(11) . . ?
C1 B1 C3 118.50(16) . . ?
C1 B1 H1B 113.1(12) . . ?
C3 B1 Ni1 127.85(13) . . ?
C3 B1 H1A 109.8(11) . . ?
C3 B1 H1B 103.7(12) . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
C1S C2S H2SA 108.9 . . ?
C1S C2S H2SB 108.9 . . ?
H2SA C2S H2SB 107.8 . . ?
C3S C2S C1S 113.2(4) . . ?
C3S C2S H2SA 108.9 . . ?
C3S C2S H2SB 108.9 . . ?
C2S C3S C3S 110.0(6) . 3_565 ?
C2S C3S H3SA 109.7 . . ?
C2S C3S H3SB 109.7 . . ?
C3S C3S H3SA 109.7 3_565 . ?
C3S C3S H3SB 109.7 3_565 . ?
H3SA C3S H3SB 108.2 . . ?
H11A C11S H11B 108.1 . . ?
C12S C11S H11A 109.6 . . ?
C12S C11S H11B 109.6 . . ?
C13S C11S H11A 109.6 3_565 . ?
C13S C11S H11B 109.6 3_565 . ?
C13S C11S C12S 110.2(10) 3_565 . ?
C11S C12S H12A 108.9 . . ?
C11S C12S H12B 108.9 . . ?
H12A C12S H12B 107.7 . . ?
C13S C12S C11S 113.4(10) . . ?
C13S C12S H12A 108.9 . . ?
C13S C12S H12B 108.9 . . ?
C11S C13S C12S 115.0(11) 3_565 . ?
C11S C13S H13A 108.5 3_565 . ?
C11S C13S H13B 108.5 3_565 . ?
C12S C13S H13A 108.5 . . ?
C12S C13S H13B 108.5 . . ?
H13A C13S H13B 107.5 . . ?

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
Ni1 P1 C11 C12 -128.57(15) . . . . ?
Ni1 P1 C11 C16 47.87(15) . . . . ?
Ni1 P1 C21 C22 -144.35(15) . . . . ?
Ni1 P1 C21 C26 39.73(16) . . . . ?
Ni1 P1 C31 C32 -142.38(13) . . . . ?
Ni1 P1 C31 C36 35.35(15) . . . . ?
Ni1 P2 C41 C42 134.30(15) . . . . ?
Ni1 P2 C41 C46 -43.52(16) . . . . ?
Ni1 P2 C51 C52 153.74(14) . . . . ?
Ni1 P2 C51 C56 -25.26(16) . . . . ?
Ni1 P2 C61 C62 129.18(16) . . . . ?
Ni1 P2 C61 C66 -51.41(16) . . . . ?
Ni1 C1 B1 C3 -119.25(15) . . . . ?
P1 C11 C12 C13 175.72(16) . . . . ?
P1 C11 C16 C15 -175.01(16) . . . . ?
P1 C21 C22 C23 -175.28(16) . . . . ?
P1 C21 C26 C25 175.10(16) . . . . ?
P1 C31 C32 C33 178.30(14) . . . . ?
P1 C31 C36 C35 -177.88(14) . . . . ?
P2 C41 C42 C43 -177.23(15) . . . . ?
P2 C41 C46 C45 178.35(15) . . . . ?
P2 C51 C52 C53 -179.10(16) . . . . ?
P2 C51 C56 C55 179.80(15) . . . . ?
P2 C61 C62 C63 179.12(17) . . . . ?
P2 C61 C66 C65 -178.64(15) . . . . ?
F1 C14 C15 C16 -179.74(19) . . . . ?
F2 C24 C25 C26 -177.0(13) . . . . ?
F2A C24 C25 C26 179.4(12) . . . . ?
F3 C34 C35 C36 174.3(9) . . . . ?
F3A C34 C35 C36 -173.2(9) . . . . ?
F4 C44 C45 C46 -178.4(8) . . . . ?
F4A C44 C45 C46 178.4(9) . . . . ?
F5 C54 C55 C56 -179.03(18) . . . . ?
F6 C64 C65 C66 -179.08(18) . . . . ?
N1 C3 B1 Ni1 66.5(2) . . . . ?
N1 C3 B1 C1 137.93(19) . . . . ?
N1 C4 C5 N2 0.0(2) . . . . ?
N2 C3 B1 Ni1 -126.85(17) . . . . ?
N2 C3 B1 C1 -55.4(2) . . . . ?
C2 C1 B1 Ni1 63.51(15) . . . . ?
C2 C1 B1 C3 -55.7(2) . . . . ?
C3 N1 C4 C5 0.4(2) . . . . ?
C3 N2 C5 C4 -0.3(2) . . . . ?
C4 N1 C3 N2 -0.6(2) . . . . ?
C4 N1 C3 B1 167.89(18) . . . . ?
C5 N2 C3 N1 0.6(2) . . . . ?
C5 N2 C3 B1 -168.93(17) . . . . ?
C6 N1 C3 N2 -175.55(16) . . . . ?
C6 N1 C3 B1 -7.1(3) . . . . ?
C6 N1 C4 C5 175.46(18) . . . . ?
C7 N2 C3 N1 174.43(16) . . . . ?
C7 N2 C3 B1 4.9(3) . . . . ?
C7 N2 C5 C4 -174.20(18) . . . . ?
C11 P1 C21 C22 92.83(17) . . . . ?
C11 P1 C21 C26 -83.08(16) . . . . ?
C11 P1 C31 C32 -14.36(16) . . . . ?
C11 P1 C31 C36 163.37(13) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C11 C16 C15 1.7(3) . . . . ?
C12 C13 C14 F1 -179.3(2) . . . . ?
C12 C13 C14 C15 1.8(4) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C11 -0.9(3) . . . . ?
C16 C11 C12 C13 -0.7(3) . . . . ?
C21 P1 C11 C12 -5.28(18) . . . . ?
C21 P1 C11 C16 171.16(14) . . . . ?
C21 P1 C31 C32 86.70(16) . . . . ?
C21 P1 C31 C36 -95.57(14) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C22 C21 C26 C25 -1.1(3) . . . . ?
C22 C23 C24 F2 176.7(12) . . . . ?
C22 C23 C24 F2A -179.7(13) . . . . ?
C22 C23 C24 C25 -1.3(3) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C24 C25 C26 C21 0.5(3) . . . . ?
C26 C21 C22 C23 0.5(3) . . . . ?
C31 P1 C11 C12 98.93(17) . . . . ?
C31 P1 C11 C16 -84.63(15) . . . . ?
C31 P1 C21 C22 -9.67(18) . . . . ?
C31 P1 C21 C26 174.41(15) . . . . ?
C31 C32 C33 C34 -0.6(3) . . . . ?
C32 C31 C36 C35 0.0(3) . . . . ?
C32 C33 C34 F3 -174.0(9) . . . . ?
C32 C33 C34 F3A 173.5(9) . . . . ?
C32 C33 C34 C35 0.0(3) . . . . ?
C33 C34 C35 C36 0.5(3) . . . . ?
C34 C35 C36 C31 -0.5(3) . . . . ?
C36 C31 C32 C33 0.6(3) . . . . ?
C41 P2 C51 C52 -77.80(17) . . . . ?
C41 P2 C51 C56 103.20(15) . . . . ?
C41 P2 C61 C62 1.96(18) . . . . ?
C41 P2 C61 C66 -178.63(14) . . . . ?
C41 C42 C43 C44 -1.2(3) . . . . ?
C42 C41 C46 C45 0.4(3) . . . . ?
C42 C43 C44 F4 179.2(9) . . . . ?
C42 C43 C44 F4A -177.7(8) . . . . ?
C42 C43 C44 C45 0.8(3) . . . . ?
C43 C44 C45 C46 0.1(3) . . . . ?
C44 C45 C46 C41 -0.7(3) . . . . ?
C46 C41 C42 C43 0.6(3) . . . . ?
C51 P2 C41 C42 4.08(18) . . . . ?
C51 P2 C41 C46 -173.74(14) . . . . ?
C51 P2 C61 C62 -101.85(17) . . . . ?
C51 P2 C61 C66 77.56(15) . . . . ?
C51 C52 C53 C54 -0.3(3) . . . . ?
C52 C51 C56 C55 0.8(3) . . . . ?
C52 C53 C54 F5 179.66(19) . . . . ?
C52 C53 C54 C55 0.0(3) . . . . ?
C53 C54 C55 C56 0.7(3) . . . . ?
C54 C55 C56 C51 -1.0(3) . . . . ?
C56 C51 C52 C53 -0.1(3) . . . . ?
C61 P2 C41 C42 -97.15(17) . . . . ?
C61 P2 C41 C46 85.04(15) . . . . ?
C61 P2 C51 C52 25.25(18) . . . . ?
C61 P2 C51 C56 -153.74(14) . . . . ?
C61 C62 C63 C64 -0.1(3) . . . . ?
C62 C61 C66 C65 0.8(3) . . . . ?
C62 C63 C64 F6 179.6(2) . . . . ?
C62 C63 C64 C65 0.0(4) . . . . ?
C63 C64 C65 C66 0.5(3) . . . . ?
C64 C65 C66 C61 -0.9(3) . . . . ?
C66 C61 C62 C63 -0.3(3) . . . . ?
B1 C1 C2 Ni1 -65.05(15) . . . . ?
C1S C2S C3S C3S -58.7(7) . . . 3_565 ?
C11S C12S C13S C11S -51.9(18) . . . 3_565 ?
C13S C11S C12S C13S 49.4(17) 3_565 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.887
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ghuaf2cult
_database_code_depnum_ccdc_archive 'CCDC 2381593'
loop_
_audit_author_name
_audit_author_address
'Herman Ho-Yung Sung'
;The Hong Kong University of Science and Technology
Hong Kong
;
_audit_update_record             
;
2024-09-03 deposited with the CCDC.	2025-06-13 downloaded from the CCDC.
;
_audit_creation_date             2023-10-19
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H29 B N2 O3'
_chemical_formula_sum            'C20 H29 B N2 O3'
_chemical_formula_weight         356.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'B C30 H28 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   10.3051(3)
_cell_length_b                   13.6933(5)
_cell_length_c                   13.8874(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.092(3)
_cell_angle_gamma                90
_cell_volume                     1908.73(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3133
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.2680
_cell_measurement_theta_min      4.3750
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6720
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.474
_diffrn_reflns_theta_min         4.405
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00  -6.00   1.00    1.00    --  -41.13 125.00 -30.00   80
  2  ω     13.00 112.00   1.00    1.00    --   41.13  57.00-150.00   99
  3  ω    117.00 175.00   1.00    2.50    --  107.01  77.00-180.00   58
  4  ω     31.00 121.00   1.00    2.50    --  107.01 -30.00  90.00   90
  5  ω    153.00 178.00   1.00    2.50    --  107.01  45.00-120.00   25
  6  ω     97.00 142.00   1.00    2.50    --  107.01  45.00-120.00   45
  7  ω     35.00 140.00   1.00    2.50    --  107.01 -77.00  90.00  105
  8  ω    103.00 178.00   1.00    2.50    --  107.01  77.00  90.00   75
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0322262000
_diffrn_orient_matrix_UB_12      -0.0923022000
_diffrn_orient_matrix_UB_13      -0.0645295000
_diffrn_orient_matrix_UB_21      -0.0002294000
_diffrn_orient_matrix_UB_22      0.0613071000
_diffrn_orient_matrix_UB_23      -0.0930335000
_diffrn_orient_matrix_UB_31      0.1500049000
_diffrn_orient_matrix_UB_32      -0.0196589000
_diffrn_orient_matrix_UB_33      0.0123453000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2961
_reflns_number_total             3743
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         3743
_refine_ls_number_restraints     490
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.271
_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)+(0.0650P)²+1.1406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1605
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18A-C17A = C18-C17 = C17-C16 = C17A-C16A
 1.52 with sigma of 0.02
 C19-C14 \\sim C20-C14 \\sim C15-C14 \\sim C19-C18 \\sim C21-C20 \\sim C16-C15
\\sim C17-C16 \\sim C18-C17
 \\sim C22-C18 \\sim C22-C21 \\sim C23-C21 \\sim C23-C16
 with sigma of 0.02
 C19A-C14A \\sim C20A-C14A \\sim C15A-C14A \\sim C19A-C18A \\sim C18A-C17A
\\sim C17A-C16A \\sim C22A-
 C18A \\sim C22A-C21A \\sim C23A-C21A \\sim C23A-C16A \\sim C16A-C15A \\sim
C21A-C20A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C23) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C14A)
\\sim Ueq, Uanis(C17A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C15A) \\sim Ueq,
Uanis(C19A) \\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C18A) \\sim Ueq,
Uanis(C23A) \\sim Ueq, Uanis(C22A) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(O1)
\\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma of 0.003 and sigma for terminal
atoms of 0.005
4. Rigid body (RIGU) restrains
 C14, C17, C16, C15, C19, C20, C18, C23, C22, C21, O1, O3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1A, C22A, C18A, C23A, C17A, C20A, C16A, C14A, C15A, C21A, C19A, O3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O1A)=Sof(C14A)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(C16A)=Sof(H16A)=
 Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=
 Sof(H20C)=Sof(H20D)=Sof(C18A)=Sof(H18A)=Sof(C23A)=Sof(H23C)=Sof(H23D)=
 Sof(C22A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(C14)=Sof(C17)=Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C18)=Sof(H18)=Sof(C23)=
 Sof(H23A)=Sof(H23B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C21)=Sof(H21)=Sof(O1)=
 FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C12(H12), C16(H16), C18(H18), B1(H1), C21(H21), C16A(H16A), C18A(H18A),
 C21A(H21A)
6.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C19(H19A,H19B), C20(H20A,H20B), C23(H23A,H23B), C22(H22A,
 H22B), C17A(H17A,H17B), C15A(H15C,H15D), C19A(H19C,H19D), C20A(H20C,H20D),
 C23A(H23C,H23D)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C2(H2)
6.d X=CH2 refined with riding coordinates:
 C5(H5A,H5B)
6.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C00E(H00A,H00B,H00C), C00J(H00D,H00E,H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1A O 0.3231(5) 0.0216(4) 0.3236(4) 0.0650(15) Uani 0.403(5) 1 d . U P A 2
O2 O 0.50243(19) 0.29107(19) 0.70098(11) 0.0725(7) Uani 1 1 d . . . . .
O3 O 0.47787(13) 0.33599(12) 0.54192(9) 0.0345(3) Uani 1 1 d . . . . .
N1 N 0.81397(17) 0.22169(16) 0.56557(13) 0.0411(5) Uani 1 1 d . . . . .
N2 N 0.73996(16) 0.34139(16) 0.47019(12) 0.0380(4) Uani 1 1 d . . . . .
C00E C 0.6907(2) 0.4365(2) 0.43379(15) 0.0445(6) Uani 1 1 d . . . . .
H00A H 0.594816 0.440172 0.430464 0.067 Uiso 1 1 calc R U . . .
H00B H 0.706974 0.446551 0.367654 0.067 Uiso 1 1 calc R U . . .
H00C H 0.736938 0.487102 0.478576 0.067 Uiso 1 1 calc R U . . .
C00J C 0.8661(3) 0.1607(2) 0.65239(19) 0.0521(6) Uani 1 1 d . . . . .
H00D H 0.920110 0.200907 0.704914 0.078 Uiso 1 1 calc R U . . .
H00E H 0.921380 0.108532 0.634542 0.078 Uiso 1 1 calc R U . . .
H00F H 0.791791 0.131965 0.675793 0.078 Uiso 1 1 calc R U . . .
C1 C 0.77948(18) 0.31721(18) 0.56667(15) 0.0357(5) Uani 1 1 d . . . . .
C2 C 0.7937(2) 0.1867(2) 0.47008(17) 0.0441(6) Uani 1 1 d . . . . .
H2 H 0.810130 0.122203 0.450594 0.053 Uiso 1 1 calc R U . . .
C3 C 0.7465(2) 0.2615(2) 0.41035(16) 0.0448(6) Uani 1 1 d . . . . .
H3 H 0.722107 0.260109 0.340167 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8896(2) 0.46920(19) 0.67482(15) 0.0391(5) Uani 1 1 d . . . . .
H4 H 0.883287 0.518791 0.721372 0.047 Uiso 1 1 calc R U . . .
C5 C 0.9872(2) 0.47963(19) 0.62828(17) 0.0434(5) Uani 1 1 d . . . . .
H5A H 0.999164 0.432609 0.580744 0.052 Uiso 1 1 calc R U . . .
H5B H 1.045407 0.534161 0.642323 0.052 Uiso 1 1 calc R U . . .
C11 C 0.5304(2) 0.3457(2) 0.64024(14) 0.0440(6) Uani 1 1 d . . . . .
C12 C 0.6278(2) 0.42780(19) 0.66036(14) 0.0392(5) Uani 1 1 d . . . . .
H12 H 0.604349 0.476359 0.605375 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6218(2) 0.4782(2) 0.75752(15) 0.0454(6) Uani 1 1 d . . . . .
H13A H 0.532936 0.506186 0.752164 0.068 Uiso 1 1 calc R U . . .
H13B H 0.688620 0.530351 0.771228 0.068 Uiso 1 1 calc R U . . .
H13C H 0.640072 0.430414 0.811421 0.068 Uiso 1 1 calc R U . . .
C14A C 0.3789(13) 0.2546(8) 0.5040(9) 0.0293(11) Uani 0.403(5) 1 d D U P A 2
C15A C 0.2526(7) 0.2612(5) 0.5460(5) 0.0266(12) Uani 0.403(5) 1 d D U P A 2
H15C H 0.219533 0.329322 0.541487 0.032 Uiso 0.403(5) 1 calc R U P A 2
H15D H 0.274061 0.241694 0.616427 0.032 Uiso 0.403(5) 1 calc R U P A 2
C16A C 0.1437(8) 0.1928(5) 0.4862(6) 0.0292(12) Uani 0.403(5) 1 d D U P A 2
H16A H 0.056968 0.202754 0.505764 0.035 Uiso 0.403(5) 1 calc R U P A 2
C17A C 0.1906(7) 0.0882(5) 0.5041(6) 0.0291(12) Uani 0.403(5) 1 d D U P A 2
H17A H 0.188908 0.068931 0.572487 0.035 Uiso 0.403(5) 1 calc R U P A 2
H17B H 0.129684 0.044435 0.458084 0.035 Uiso 0.403(5) 1 calc R U P A 2
C18A C 0.3264(7) 0.0779(6) 0.4890(5) 0.0396(12) Uani 0.403(5) 1 d D U P A 2
H18A H 0.361449 0.011270 0.510184 0.048 Uiso 0.403(5) 1 calc R U P A 2
C19A C 0.4261(9) 0.1566(6) 0.5418(6) 0.0355(13) Uani 0.403(5) 1 d D U P A 2
H19C H 0.433131 0.153658 0.614003 0.043 Uiso 0.403(5) 1 calc R U P A 2
H19D H 0.515416 0.144056 0.529251 0.043 Uiso 0.403(5) 1 calc R U P A 2
C20A C 0.3664(7) 0.2626(5) 0.3923(5) 0.0292(12) Uani 0.403(5) 1 d D U P A 2
H20C H 0.453345 0.248739 0.376103 0.035 Uiso 0.403(5) 1 calc R U P A 2
H20D H 0.338532 0.329450 0.369331 0.035 Uiso 0.403(5) 1 calc R U P A 2
C21A C 0.2606(6) 0.1872(5) 0.3405(4) 0.0315(11) Uani 0.403(5) 1 d D U P A 2
H21A H 0.249618 0.190001 0.267184 0.038 Uiso 0.403(5) 1 calc R U P A 2
C22A C 0.3061(6) 0.0877(5) 0.3787(5) 0.0341(11) Uani 0.403(5) 1 d D U P A 2
C23A C 0.1266(7) 0.2086(5) 0.3689(5) 0.0314(12) Uani 0.403(5) 1 d D U P A 2
H23C H 0.056790 0.164330 0.332151 0.038 Uiso 0.403(5) 1 calc R U P A 2
H23D H 0.098910 0.276714 0.351038 0.038 Uiso 0.403(5) 1 calc R U P A 2
B1 B 0.7798(2) 0.3835(2) 0.66321(16) 0.0370(6) Uani 1 1 d . . . . .
H1 H 0.805128 0.340330 0.722559 0.044 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1A C22A 1.223(7) . ?
O2 C11 1.210(3) . ?
O3 C11 1.357(2) . ?
O3 C14A 1.522(13) . ?
N1 C00J 1.465(3) . ?
N1 C1 1.356(3) . ?
N1 C2 1.381(3) . ?
N2 C00E 1.446(3) . ?
N2 C1 1.350(3) . ?
N2 C3 1.384(3) . ?
C00E H00A 0.9800 . ?
C00E H00B 0.9800 . ?
C00E H00C 0.9800 . ?
C00J H00D 0.9800 . ?
C00J H00E 0.9800 . ?
C00J H00F 0.9800 . ?
C1 B1 1.619(3) . ?
C2 H2 0.9500 . ?
C3 C2 1.339(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.320(3) . ?
C4 B1 1.612(3) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C12 C11 1.491(3) . ?
C12 H12 1.0000 . ?
C12 B1 1.672(3) . ?
C13 C12 1.529(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14A C15A 1.545(11) . ?
C14A C19A 1.483(10) . ?
C14A C20A 1.531(10) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C16A C15A 1.550(7) . ?
C16A H16A 1.0000 . ?
C16A C23A 1.614(9) . ?
C17A C16A 1.514(7) . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C17A C18A 1.468(8) . ?
C18A H18A 1.0000 . ?
C18A C22A 1.504(8) . ?
C19A C18A 1.553(9) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C20A C21A 1.555(7) . ?
C21A H21A 1.0000 . ?
C22A C21A 1.497(7) . ?
C23A C21A 1.547(8) . ?
C23A H23C 0.9900 . ?
C23A H23D 0.9900 . ?
B1 H1 1.0000 . ?

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
C11 O3 C14A 120.2(4) . . ?
C1 N1 C00J 126.0(2) . . ?
C1 N1 C2 111.3(2) . . ?
C2 N1 C00J 122.7(2) . . ?
C1 N2 C00E 124.8(2) . . ?
C1 N2 C3 110.9(2) . . ?
C3 N2 C00E 124.21(18) . . ?
N2 C00E H00A 109.5 . . ?
N2 C00E H00B 109.5 . . ?
N2 C00E H00C 109.5 . . ?
H00A C00E H00B 109.5 . . ?
H00A C00E H00C 109.5 . . ?
H00B C00E H00C 109.5 . . ?
N1 C00J H00D 109.5 . . ?
N1 C00J H00E 109.5 . . ?
N1 C00J H00F 109.5 . . ?
H00D C00J H00E 109.5 . . ?
H00D C00J H00F 109.5 . . ?
H00E C00J H00F 109.5 . . ?
N1 C1 B1 126.80(19) . . ?
N2 C1 N1 104.24(19) . . ?
N2 C1 B1 128.9(2) . . ?
N1 C2 H2 126.7 . . ?
C3 C2 N1 106.5(2) . . ?
C3 C2 H2 126.7 . . ?
N2 C3 H3 126.5 . . ?
C2 C3 N2 107.0(2) . . ?
C2 C3 H3 126.5 . . ?
C5 C4 H4 115.7 . . ?
C5 C4 B1 128.7(2) . . ?
B1 C4 H4 115.7 . . ?
C4 C5 H5A 120.0 . . ?
C4 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
O2 C11 O3 122.5(2) . . ?
O2 C11 C12 126.31(19) . . ?
O3 C11 C12 111.14(18) . . ?
C11 C12 H12 108.8 . . ?
C11 C12 C13 110.23(17) . . ?
C11 C12 B1 108.6(2) . . ?
C13 C12 H12 108.8 . . ?
C13 C12 B1 111.57(16) . . ?
B1 C12 H12 108.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14A C15A 112.5(7) . . ?
O3 C14A C20A 101.2(7) . . ?
C19A C14A O3 113.6(9) . . ?
C19A C14A C15A 99.0(8) . . ?
C19A C14A C20A 111.6(8) . . ?
C20A C14A C15A 119.6(9) . . ?
C14A C15A H15C 109.8 . . ?
C14A C15A H15D 109.8 . . ?
C14A C15A C16A 109.4(7) . . ?
H15C C15A H15D 108.2 . . ?
C16A C15A H15C 109.8 . . ?
C16A C15A H15D 109.8 . . ?
C15A C16A H16A 110.9 . . ?
C15A C16A C23A 111.1(6) . . ?
C17A C16A C15A 108.6(6) . . ?
C17A C16A H16A 110.9 . . ?
C17A C16A C23A 104.5(6) . . ?
C23A C16A H16A 110.9 . . ?
C16A C17A H17A 109.6 . . ?
C16A C17A H17B 109.6 . . ?
H17A C17A H17B 108.1 . . ?
C18A C17A C16A 110.3(6) . . ?
C18A C17A H17A 109.6 . . ?
C18A C17A H17B 109.6 . . ?
C17A C18A H18A 109.8 . . ?
C17A C18A C19A 114.6(7) . . ?
C17A C18A C22A 102.6(6) . . ?
C19A C18A H18A 109.8 . . ?
C22A C18A H18A 109.8 . . ?
C22A C18A C19A 110.0(6) . . ?
C14A C19A C18A 109.4(8) . . ?
C14A C19A H19C 109.8 . . ?
C14A C19A H19D 109.8 . . ?
C18A C19A H19C 109.8 . . ?
C18A C19A H19D 109.8 . . ?
H19C C19A H19D 108.2 . . ?
C14A C20A H20C 110.1 . . ?
C14A C20A H20D 110.1 . . ?
C14A C20A C21A 108.0(7) . . ?
H20C C20A H20D 108.4 . . ?
C21A C20A H20C 110.1 . . ?
C21A C20A H20D 110.1 . . ?
C20A C21A H21A 110.5 . . ?
C22A C21A C20A 108.1(5) . . ?
C22A C21A H21A 110.5 . . ?
C22A C21A C23A 108.0(5) . . ?
C23A C21A C20A 109.2(5) . . ?
C23A C21A H21A 110.5 . . ?
O1A C22A C18A 124.3(7) . . ?
O1A C22A C21A 121.9(6) . . ?
C21A C22A C18A 113.7(5) . . ?
C16A C23A H23C 109.8 . . ?
C16A C23A H23D 109.8 . . ?
C21A C23A C16A 109.4(5) . . ?
C21A C23A H23C 109.8 . . ?
C21A C23A H23D 109.8 . . ?
H23C C23A H23D 108.2 . . ?
C1 B1 C12 110.95(16) . . ?
C1 B1 H1 107.6 . . ?
C4 B1 C1 111.16(17) . . ?
C4 B1 C12 111.8(2) . . ?
C4 B1 H1 107.6 . . ?
C12 B1 H1 107.6 . . ?

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
O1A C22A C21A C20A -122.4(6) . . . . ?
O1A C22A C21A C23A 119.6(6) . . . . ?
O3 C14A C15A C16A 166.6(6) . . . . ?
O3 C14A C19A C18A -173.1(6) . . . . ?
O3 C14A C20A C21A -176.7(5) . . . . ?
N1 C1 B1 C4 114.3(2) . . . . ?
N1 C1 B1 C12 -120.7(2) . . . . ?
N2 C1 B1 C4 -69.1(3) . . . . ?
N2 C1 B1 C12 55.9(3) . . . . ?
N2 C3 C2 N1 0.6(2) . . . . ?
C00E N2 C1 N1 178.56(17) . . . . ?
C00E N2 C1 B1 1.4(3) . . . . ?
C00E N2 C3 C2 -178.44(18) . . . . ?
C00J N1 C1 N2 178.89(19) . . . . ?
C00J N1 C1 B1 -3.8(3) . . . . ?
C00J N1 C2 C3 -179.72(19) . . . . ?
C1 N1 C2 C3 0.3(2) . . . . ?
C1 N2 C3 C2 -1.4(2) . . . . ?
C2 N1 C1 N2 -1.1(2) . . . . ?
C2 N1 C1 B1 176.14(18) . . . . ?
C3 N2 C1 N1 1.6(2) . . . . ?
C3 N2 C1 B1 -175.65(18) . . . . ?
C5 C4 B1 C1 -12.5(3) . . . . ?
C5 C4 B1 C12 -137.0(2) . . . . ?
C11 O3 C14A C15A 59.9(8) . . . . ?
C11 O3 C14A C19A -51.5(9) . . . . ?
C11 O3 C14A C20A -171.2(4) . . . . ?
C11 C12 B1 C1 50.1(2) . . . . ?
C11 C12 B1 C4 174.84(16) . . . . ?
C13 C12 C11 O2 -36.9(4) . . . . ?
C13 C12 C11 O3 145.5(2) . . . . ?
C13 C12 B1 C1 171.8(2) . . . . ?
C13 C12 B1 C4 -63.5(2) . . . . ?
C14A O3 C11 O2 0.5(6) . . . . ?
C14A O3 C11 C12 178.2(5) . . . . ?
C14A C19A C18A C17A -60.5(9) . . . . ?
C14A C19A C18A C22A 54.5(9) . . . . ?
C14A C20A C21A C22A -58.9(7) . . . . ?
C14A C20A C21A C23A 58.3(7) . . . . ?
C15A C14A C19A C18A 67.5(9) . . . . ?
C15A C14A C20A C21A -52.6(9) . . . . ?
C15A C16A C23A C21A 59.4(7) . . . . ?
C16A C17A C18A C19A 47.9(8) . . . . ?
C16A C17A C18A C22A -71.3(8) . . . . ?
C16A C23A C21A C20A -63.9(6) . . . . ?
C16A C23A C21A C22A 53.3(6) . . . . ?
C17A C16A C15A C14A 65.9(8) . . . . ?
C17A C16A C23A C21A -57.4(7) . . . . ?
C17A C18A C22A O1A -112.9(7) . . . . ?
C17A C18A C22A C21A 66.4(7) . . . . ?
C18A C17A C16A C15A -49.8(8) . . . . ?
C18A C17A C16A C23A 68.8(7) . . . . ?
C18A C22A C21A C20A 58.3(7) . . . . ?
C18A C22A C21A C23A -59.7(7) . . . . ?
C19A C14A C15A C16A -73.2(9) . . . . ?
C19A C14A C20A C21A 62.2(10) . . . . ?
C19A C18A C22A O1A 124.8(7) . . . . ?
C19A C18A C22A C21A -56.0(8) . . . . ?
C20A C14A C15A C16A 48.1(10) . . . . ?
C20A C14A C19A C18A -59.4(11) . . . . ?
C23A C16A C15A C14A -48.4(8) . . . . ?
B1 C12 C11 O2 85.6(3) . . . . ?
B1 C12 C11 O3 -92.1(2) . . . . ?


_olex2_date_sample_data_collection 2023-10-13
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.451
_oxdiff_exptl_absorpt_empirical_full_min 0.752
