# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2263083'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki'
;University of Wurzburg
Germany
;
_audit_update_record             
;
2023-05-15 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;


_audit_creation_method           'CIF-fill 1.3r (K.Radacki, 2005-23)'
_audit_creation_date             2023-03-10
_shelx_SHELXL_version_number     2019/2
_chemical_formula_moiety         '0.97(C22 H33 B) 0.03(C22 H32 B Br)'
_chemical_formula_sum            'C22 H32.97 B Br0.03'
_chemical_formula_weight         310.66
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'


_cell_length_a                   9.7239(7)
_cell_length_b                   9.0900(5)
_cell_length_c                   11.1927(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.359(7)
_cell_angle_gamma                90
_cell_volume                     981.18(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2150
_cell_measurement_theta_min      4.5550
_cell_measurement_theta_max      66.3850

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_F_000             342
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 Crystals were grown from saturated solution of hexane at -30 °C. For data 
 collection the crystal was immersed in a film of perfluoropolyether oil, 
 mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0119
-1 0 1 0.0078
2 1 1 0.0070
-2 -1 -1 0.0242
-1 2 -1 0.0191
2 -1 -1 0.0204
-1 2 1 0.0115
1 0 0 0.0110

_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.990
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω     16.00  64.60   0.60    5.00    --   58.57 -95.00 -90.00   81
  2  ω     16.00  64.60   0.60    5.00    --   58.57 -95.00-180.00   81
  3  ω    -88.00 -15.40   0.60    5.00    --  -60.16 126.00-150.00  121
  4  ω    -88.00 -15.40   0.60    5.00    --  -60.16 126.00 -60.00  121
  5  ω     29.00  77.60   0.60    5.00    --   71.34 -95.00  60.00   81
  6  ω     29.00  77.60   0.60    5.00    --   71.34 -95.00 -30.00   81
  7  ω    -92.00 -32.00   0.60    5.00    --  -76.35 112.00 150.00  100
  8  ω   -127.00 -40.00   0.60    5.00    --  -76.35 -15.00 -30.00  145
  9  ω     46.00 133.00   0.60    5.00    --   82.28  15.00-180.00  145
 10  ω     37.00  91.60   0.60    5.00    --   82.28-112.00 -60.00   91
 11  ω     37.00  91.60   0.60    5.00    --   82.28-112.00-180.00   91
 12  ω     37.00  91.60   0.60    5.00    --   82.28-112.00-150.00   91
 13  ω     37.00  91.60   0.60    5.00    --   82.28-112.00 150.00   91
 14  ω     46.00 133.00   0.60    5.00    --   82.28  15.00  90.00  145
 15  ω     45.00  72.00   0.60    5.00    --   82.28 -95.00 -60.00   45
 16  ω     41.00  80.00   0.60    5.00    --   82.28 -95.00-150.00   65
 17  ω     53.00  98.00   0.60    5.00    --   82.28  15.00-120.00   75
 18  ω     40.00  65.20   0.60    5.00    --   82.28 -95.00  60.00   42
 19  ω     47.00  85.40   0.60    5.00    --   82.28-112.00 -90.00   64
 20  ω     53.00  79.40   0.60    5.00    --   82.28 -95.00 -90.00   44
 21  ω     37.00  79.60   0.60    5.00    --   82.28-112.00  90.00   71
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      0.0107011000
_diffrn_orient_matrix_UB_12      -0.0362238000
_diffrn_orient_matrix_UB_13      0.1352619000
_diffrn_orient_matrix_UB_21      0.1198063000
_diffrn_orient_matrix_UB_22      -0.1073284000
_diffrn_orient_matrix_UB_23      -0.0132099000
_diffrn_orient_matrix_UB_31      0.1052288000
_diffrn_orient_matrix_UB_32      0.1259383000
_diffrn_orient_matrix_UB_33      0.0281188000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            9056
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.585
_diffrn_reflns_theta_max         73.587
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2030
_reflns_number_gt                1358
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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. Completness statistics refer to single and composite 
 reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'

_refine_special_details          
;
 Molecule was refined as disordered over the mirror plane with local symmetry 
 switched off. The atomic displacement parameters of atoms were restraint with 
 RIGU keyword in ShelXL input ('enhanced rigid bond' restraint for all bonds in 
 the connectivity list). The Uii displacement parameters of all atoms 
 positioned close to the symmetry plain were restrained with ISOR keyword to 
 approximate isotropic behavior. The atomic displacement parameters of atoms 
 whose symmetry equivalents overlapped were constrained to the same volumes.  
 The distances in ethyl-groups were restrained during refinement to the same 
 value. To keep axial position of Br-atom in minor component of disorder 
 (Duryl-Bromide is a 3% impurity of main product) the 1--3 distances B-C(Dur) 
 were restrained. ADPs of this atom were based on C4 of duryl-group, and were
 kept constrained during refinement.
 Data were refined as a 2-component twin. Twin-law was computed with CrysalisPro 
 during indexing. Less than 1.5% of reflections were overlapping between both 
 twin domains. The BASF parameter was refined to just 0.3%, however using twin 
 refinement improved K-statistic for week reflections (K=Mean[Fo^2]/Mean[Fc^2]).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1018P)²+1.3674P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2030
_refine_ls_number_parameters     197
_refine_ls_number_restraints     222
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.2398
_refine_ls_wR_factor_gt          0.2164
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.050
_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_
_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
B1_1 B 0.7325(6) 0.2198(4) 0.6838(5) 0.0341(15) Uani 0.5 1 d . U P A -1
C2_1 C 0.7119(5) 0.2627(4) 0.5479(4) 0.0443(11) Uani 0.5 1 d . U P A -1
C3_1 C 0.5756(4) 0.2491(3) 0.5081(4) 0.0397(8) Uani 0.5 1 d . U P A -1
C4_1 C 0.4969(5) 0.1976(4) 0.6095(5) 0.0387(11) Uani 0.5 1 d . . P A -1
C5_1 C 0.5823(5) 0.1790(4) 0.7124(5) 0.0383(11) Uani 0.5 1 d . . P A -1
C6_1 C 0.8251(6) 0.3111(5) 0.4744(5) 0.0420(11) Uani 0.5 1 d D . P A -1
H6A_1 H 0.882205 0.389125 0.517887 0.050 Uiso 0.5 1 calc R U P A -1
H6B_1 H 0.782878 0.351317 0.395964 0.050 Uiso 0.5 1 calc R U P A -1
C7_1 C 0.9161(6) 0.1782(5) 0.4538(5) 0.0442(12) Uani 0.5 1 d D . P A -1
H7A_1 H 0.995047 0.210519 0.414142 0.066 Uiso 0.5 1 calc R U P A -1
H7B_1 H 0.861411 0.106232 0.402729 0.066 Uiso 0.5 1 calc R U P A -1
H7C_1 H 0.950043 0.132977 0.531502 0.066 Uiso 0.5 1 calc R U P A -1
C8_1 C 0.5033(6) 0.2778(5) 0.3831(5) 0.0487(16) Uani 0.5 1 d D . P A -1
H8A_1 H 0.548089 0.362303 0.347781 0.058 Uiso 0.5 1 calc R U P A -1
H8B_1 H 0.405484 0.304421 0.387973 0.058 Uiso 0.5 1 calc R U P A -1
C9_1 C 0.5076(7) 0.1441(6) 0.3005(5) 0.0519(14) Uani 0.5 1 d D . P A -1
H9A_1 H 0.454701 0.165454 0.221913 0.078 Uiso 0.5 1 calc R U P A -1
H9B_1 H 0.466710 0.059063 0.336698 0.078 Uiso 0.5 1 calc R U P A -1
H9C_1 H 0.603988 0.122194 0.290136 0.078 Uiso 0.5 1 calc R U P A -1
C10_1 C 0.3431(6) 0.1753(5) 0.5880(6) 0.0451(13) Uani 0.5 1 d D . P A -1
H10A_1 H 0.315441 0.102807 0.646462 0.054 Uiso 0.5 1 calc R U P A -1
H10B_1 H 0.316697 0.135526 0.505905 0.054 Uiso 0.5 1 calc R U P A -1
C11_1 C 0.2667(7) 0.3212(6) 0.6013(6) 0.0481(14) Uani 0.5 1 d D . P A -1
H11A_1 H 0.167018 0.302357 0.597674 0.072 Uiso 0.5 1 calc R U P A -1
H11B_1 H 0.283300 0.387895 0.535921 0.072 Uiso 0.5 1 calc R U P A -1
H11C_1 H 0.301065 0.366306 0.678971 0.072 Uiso 0.5 1 calc R U P A -1
C12_1 C 0.5413(6) 0.1303(5) 0.8313(5) 0.0472(13) Uani 0.5 1 d D . P A -1
H12A_1 H 0.600225 0.046480 0.862594 0.057 Uiso 0.5 1 calc R U P A -1
H12B_1 H 0.443713 0.096551 0.819602 0.057 Uiso 0.5 1 calc R U P A -1
C13_1 C 0.5573(5) 0.2564(13) 0.9232(4) 0.0560(13) Uani 0.5 1 d D U P A -1
H13A_1 H 0.528037 0.222843 0.999217 0.084 Uiso 0.5 1 calc R U P A -1
H13B_1 H 0.499536 0.339696 0.891957 0.084 Uiso 0.5 1 calc R U P A -1
H13C_1 H 0.654622 0.287317 0.937109 0.084 Uiso 0.5 1 calc R U P A -1
C1_2 C 0.8779(2) 0.2189(2) 0.76942(18) 0.0306(12) Uani 0.5 1 d G U P A -1
C2_2 C 0.9405(2) 0.35609(18) 0.8018(2) 0.0290(11) Uani 0.5 1 d G . P A -1
C3_2 C 1.0766(2) 0.35348(19) 0.8654(2) 0.0307(11) Uani 0.5 1 d G . P A -1
C4_2 C 1.14106(19) 0.2166(2) 0.89255(18) 0.0349(13) Uani 0.5 1 d G U P A -1
H4_2 H 1.232093 0.215849 0.935108 0.042 Uiso 0.4830(8) 1 calc R U P B -1
C5_2 C 1.0773(2) 0.08083(19) 0.8597(2) 0.0363(12) Uani 0.5 1 d G . P A -1
C6_2 C 0.9412(2) 0.08054(18) 0.7961(2) 0.0358(12) Uani 0.5 1 d G . P A -1
C7_2 C 0.8648(4) -0.0599(2) 0.7572(4) 0.0472(15) Uani 0.5 1 d G . P A -1
H7A_2 H 0.873536 -0.129604 0.824585 0.071 Uiso 0.5 1 calc R U P A -1
H7B_2 H 0.904874 -0.103247 0.689306 0.071 Uiso 0.5 1 calc R U P A -1
H7C_2 H 0.766627 -0.037940 0.732586 0.071 Uiso 0.5 1 calc R U P A -1
C8_2 C 1.1553(4) -0.0610(2) 0.8928(4) 0.0454(15) Uani 0.5 1 d G . P A -1
H8A_2 H 1.161261 -0.118764 0.819699 0.068 Uiso 0.5 1 calc R U P A -1
H8B_2 H 1.105961 -0.117827 0.948350 0.068 Uiso 0.5 1 calc R U P A -1
H8C_2 H 1.248888 -0.037927 0.931591 0.068 Uiso 0.5 1 calc R U P A -1
C9_2 C 1.1536(3) 0.4940(2) 0.9047(4) 0.0444(15) Uani 0.5 1 d G . P A -1
H9A_2 H 1.246080 0.469554 0.945284 0.067 Uiso 0.5 1 calc R U P A -1
H9B_2 H 1.102014 0.548129 0.960285 0.067 Uiso 0.5 1 calc R U P A -1
H9C_2 H 1.162311 0.555023 0.833905 0.067 Uiso 0.5 1 calc R U P A -1
C10_2 C 0.8633(3) 0.4978(2) 0.7689(4) 0.0397(14) Uani 0.5 1 d G . P A -1
H10A_2 H 0.927125 0.570223 0.741586 0.060 Uiso 0.5 1 calc R U P A -1
H10B_2 H 0.825208 0.536162 0.839639 0.060 Uiso 0.5 1 calc R U P A -1
H10C_2 H 0.787505 0.478962 0.704180 0.060 Uiso 0.5 1 calc R U P A -1
Br1_2 Br 1.2883(14) 0.238(6) 0.9884(14) 0.061 Uani 0.0170(8) 1 d . . P B -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
B1_1 C2_1 1.558(7) . ?
B1_1 C5_1 1.579(7) . ?
B1_1 C1_2 1.603(6) . ?
C2_1 C3_1 1.349(6) . ?
C2_1 C6_1 1.521(7) . ?
C3_1 C8_1 1.506(6) . ?
C3_1 C4_1 1.522(7) . ?
C4_1 C5_1 1.342(7) . ?
C4_1 C10_1 1.498(8) . ?
C5_1 C12_1 1.503(7) . ?
C6_1 C7_1 1.532(5) . ?
C6_1 H6A_1 0.9900 . ?
C6_1 H6B_1 0.9900 . ?
C7_1 H7A_1 0.9800 . ?
C7_1 H7B_1 0.9800 . ?
C7_1 H7C_1 0.9800 . ?
C8_1 C9_1 1.530(5) . ?
C8_1 H8A_1 0.9900 . ?
C8_1 H8B_1 0.9900 . ?
C9_1 H9A_1 0.9800 . ?
C9_1 H9B_1 0.9800 . ?
C9_1 H9C_1 0.9800 . ?
C10_1 C11_1 1.537(5) . ?
C10_1 H10A_1 0.9900 . ?
C10_1 H10B_1 0.9900 . ?
C11_1 H11A_1 0.9800 . ?
C11_1 H11B_1 0.9800 . ?
C11_1 H11C_1 0.9800 . ?
C12_1 C13_1 1.535(7) . ?
C12_1 H12A_1 0.9900 . ?
C12_1 H12B_1 0.9900 . ?
C13_1 H13A_1 0.9800 . ?
C13_1 H13B_1 0.9800 . ?
C13_1 H13C_1 0.9800 . ?
C1_2 C2_2 1.4145 . ?
C1_2 C6_2 1.4146 . ?
C2_2 C3_2 1.4207 . ?
C2_2 C10_2 1.5127 . ?
C3_2 C4_2 1.4087 . ?
C3_2 C9_2 1.5166 . ?
C4_2 C5_2 1.4087 . ?
C4_2 H4_2 0.9500 . ?
C5_2 C6_2 1.4207 . ?
C5_2 C8_2 1.5168 . ?
C6_2 C7_2 1.5126 . ?
C7_2 H7A_2 0.9800 . ?
C7_2 H7B_2 0.9800 . ?
C7_2 H7C_2 0.9800 . ?
C8_2 H8A_2 0.9800 . ?
C8_2 H8B_2 0.9800 . ?
C8_2 H8C_2 0.9800 . ?
C9_2 H9A_2 0.9800 . ?
C9_2 H9B_2 0.9800 . ?
C9_2 H9C_2 0.9800 . ?
C10_2 H10A_2 0.9800 . ?
C10_2 H10B_2 0.9800 . ?
C10_2 H10C_2 0.9800 . ?

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_1 B1_1 C5_1 104.5(4) . . ?
C2_1 B1_1 C1_2 125.3(4) . . ?
C5_1 B1_1 C1_2 130.2(4) . . ?
C3_1 C2_1 C6_1 126.6(4) . . ?
C3_1 C2_1 B1_1 107.3(4) . . ?
C6_1 C2_1 B1_1 126.1(4) . . ?
C2_1 C3_1 C8_1 127.8(4) . . ?
C2_1 C3_1 C4_1 110.4(4) . . ?
C8_1 C3_1 C4_1 121.8(4) . . ?
C5_1 C4_1 C10_1 128.1(5) . . ?
C5_1 C4_1 C3_1 111.4(4) . . ?
C10_1 C4_1 C3_1 120.6(5) . . ?
C4_1 C5_1 C12_1 126.3(5) . . ?
C4_1 C5_1 B1_1 106.5(4) . . ?
C12_1 C5_1 B1_1 127.3(5) . . ?
C2_1 C6_1 C7_1 109.0(3) . . ?
C2_1 C6_1 H6A_1 109.9 . . ?
C7_1 C6_1 H6A_1 109.9 . . ?
C2_1 C6_1 H6B_1 109.9 . . ?
C7_1 C6_1 H6B_1 109.9 . . ?
H6A_1 C6_1 H6B_1 108.3 . . ?
C6_1 C7_1 H7A_1 109.5 . . ?
C6_1 C7_1 H7B_1 109.5 . . ?
H7A_1 C7_1 H7B_1 109.5 . . ?
C6_1 C7_1 H7C_1 109.5 . . ?
H7A_1 C7_1 H7C_1 109.5 . . ?
H7B_1 C7_1 H7C_1 109.5 . . ?
C3_1 C8_1 C9_1 112.2(3) . . ?
C3_1 C8_1 H8A_1 109.2 . . ?
C9_1 C8_1 H8A_1 109.2 . . ?
C3_1 C8_1 H8B_1 109.2 . . ?
C9_1 C8_1 H8B_1 109.2 . . ?
H8A_1 C8_1 H8B_1 107.9 . . ?
C8_1 C9_1 H9A_1 109.5 . . ?
C8_1 C9_1 H9B_1 109.5 . . ?
H9A_1 C9_1 H9B_1 109.5 . . ?
C8_1 C9_1 H9C_1 109.5 . . ?
H9A_1 C9_1 H9C_1 109.5 . . ?
H9B_1 C9_1 H9C_1 109.5 . . ?
C4_1 C10_1 C11_1 110.7(3) . . ?
C4_1 C10_1 H10A_1 109.5 . . ?
C11_1 C10_1 H10A_1 109.5 . . ?
C4_1 C10_1 H10B_1 109.5 . . ?
C11_1 C10_1 H10B_1 109.5 . . ?
H10A_1 C10_1 H10B_1 108.1 . . ?
C10_1 C11_1 H11A_1 109.5 . . ?
C10_1 C11_1 H11B_1 109.5 . . ?
H11A_1 C11_1 H11B_1 109.5 . . ?
C10_1 C11_1 H11C_1 109.5 . . ?
H11A_1 C11_1 H11C_1 109.5 . . ?
H11B_1 C11_1 H11C_1 109.5 . . ?
C5_1 C12_1 C13_1 110.9(4) . . ?
C5_1 C12_1 H12A_1 109.5 . . ?
C13_1 C12_1 H12A_1 109.5 . . ?
C5_1 C12_1 H12B_1 109.5 . . ?
C13_1 C12_1 H12B_1 109.5 . . ?
H12A_1 C12_1 H12B_1 108.0 . . ?
C12_1 C13_1 H13A_1 109.5 . . ?
C12_1 C13_1 H13B_1 109.5 . . ?
H13A_1 C13_1 H13B_1 109.5 . . ?
C12_1 C13_1 H13C_1 109.5 . . ?
H13A_1 C13_1 H13C_1 109.5 . . ?
H13B_1 C13_1 H13C_1 109.5 . . ?
C2_2 C1_2 C6_2 124.7 . . ?
C2_2 C1_2 B1_1 117.76(17) . . ?
C6_2 C1_2 B1_1 117.20(17) . . ?
C1_2 C2_2 C3_2 117.1 . . ?
C1_2 C2_2 C10_2 120.3 . . ?
C3_2 C2_2 C10_2 122.5 . . ?
C4_2 C3_2 C2_2 118.9 . . ?
C4_2 C3_2 C9_2 119.5 . . ?
C2_2 C3_2 C9_2 121.7 . . ?
C3_2 C4_2 C5_2 123.3 . . ?
C3_2 C4_2 H4_2 118.4 . . ?
C5_2 C4_2 H4_2 118.4 . . ?
C4_2 C5_2 C6_2 118.9 . . ?
C4_2 C5_2 C8_2 119.4 . . ?
C6_2 C5_2 C8_2 121.7 . . ?
C1_2 C6_2 C5_2 117.1 . . ?
C1_2 C6_2 C7_2 120.4 . . ?
C5_2 C6_2 C7_2 122.5 . . ?
C6_2 C7_2 H7A_2 109.5 . . ?
C6_2 C7_2 H7B_2 109.5 . . ?
H7A_2 C7_2 H7B_2 109.5 . . ?
C6_2 C7_2 H7C_2 109.5 . . ?
H7A_2 C7_2 H7C_2 109.5 . . ?
H7B_2 C7_2 H7C_2 109.5 . . ?
C5_2 C8_2 H8A_2 109.5 . . ?
C5_2 C8_2 H8B_2 109.5 . . ?
H8A_2 C8_2 H8B_2 109.5 . . ?
C5_2 C8_2 H8C_2 109.5 . . ?
H8A_2 C8_2 H8C_2 109.5 . . ?
H8B_2 C8_2 H8C_2 109.5 . . ?
C3_2 C9_2 H9A_2 109.5 . . ?
C3_2 C9_2 H9B_2 109.5 . . ?
H9A_2 C9_2 H9B_2 109.5 . . ?
C3_2 C9_2 H9C_2 109.5 . . ?
H9A_2 C9_2 H9C_2 109.5 . . ?
H9B_2 C9_2 H9C_2 109.5 . . ?
C2_2 C10_2 H10A_2 109.5 . . ?
C2_2 C10_2 H10B_2 109.5 . . ?
H10A_2 C10_2 H10B_2 109.5 . . ?
C2_2 C10_2 H10C_2 109.5 . . ?
H10A_2 C10_2 H10C_2 109.5 . . ?
H10B_2 C10_2 H10C_2 109.5 . . ?

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
C5_1 B1_1 C2_1 C3_1 0.21(9) . . . . ?
C1_2 B1_1 C2_1 C3_1 179.8(2) . . . . ?
C5_1 B1_1 C2_1 C6_1 -179.82(15) . . . . ?
C1_2 B1_1 C2_1 C6_1 -0.2(3) . . . . ?
C6_1 C2_1 C3_1 C8_1 0.09(16) . . . . ?
B1_1 C2_1 C3_1 C8_1 -179.94(12) . . . . ?
C6_1 C2_1 C3_1 C4_1 179.84(15) . . . . ?
B1_1 C2_1 C3_1 C4_1 -0.19(10) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.1(2) . . . . ?
C8_1 C3_1 C4_1 C5_1 179.87(18) . . . . ?
C2_1 C3_1 C4_1 C10_1 179.51(16) . . . . ?
C8_1 C3_1 C4_1 C10_1 -0.7(3) . . . . ?
C10_1 C4_1 C5_1 C12_1 0.1(4) . . . . ?
C3_1 C4_1 C5_1 C12_1 179.50(19) . . . . ?
C10_1 C4_1 C5_1 B1_1 -179.3(2) . . . . ?
C3_1 C4_1 C5_1 B1_1 0.0(2) . . . . ?
C2_1 B1_1 C5_1 C4_1 -0.15(18) . . . . ?
C1_2 B1_1 C5_1 C4_1 -179.7(3) . . . . ?
C2_1 B1_1 C5_1 C12_1 -179.59(19) . . . . ?
C1_2 B1_1 C5_1 C12_1 0.8(4) . . . . ?
C3_1 C2_1 C6_1 C7_1 -108.9(4) . . . . ?
B1_1 C2_1 C6_1 C7_1 71.1(4) . . . . ?
C2_1 C3_1 C8_1 C9_1 85.2(5) . . . . ?
C4_1 C3_1 C8_1 C9_1 -94.5(5) . . . . ?
C5_1 C4_1 C10_1 C11_1 94.8(5) . . . . ?
C3_1 C4_1 C10_1 C11_1 -84.5(5) . . . . ?
C4_1 C5_1 C12_1 C13_1 -110.9(5) . . . . ?
B1_1 C5_1 C12_1 C13_1 68.5(5) . . . . ?
C2_1 B1_1 C1_2 C2_2 70.3(2) . . . . ?
C5_1 B1_1 C1_2 C2_2 -110.2(3) . . . . ?
C2_1 B1_1 C1_2 C6_2 -103.0(2) . . . . ?
C5_1 B1_1 C1_2 C6_2 76.5(3) . . . . ?
C6_2 C1_2 C2_2 C3_2 0.1 . . . . ?
B1_1 C1_2 C2_2 C3_2 -172.6(3) . . . . ?
C6_2 C1_2 C2_2 C10_2 -179.9 . . . . ?
B1_1 C1_2 C2_2 C10_2 7.4(3) . . . . ?
C1_2 C2_2 C3_2 C4_2 0.0 . . . . ?
C10_2 C2_2 C3_2 C4_2 180.0 . . . . ?
C1_2 C2_2 C3_2 C9_2 -180.0 . . . . ?
C10_2 C2_2 C3_2 C9_2 0.0 . . . . ?
C2_2 C3_2 C4_2 C5_2 0.0 . . . . ?
C9_2 C3_2 C4_2 C5_2 179.9 . . . . ?
C3_2 C4_2 C5_2 C6_2 0.0 . . . . ?
C3_2 C4_2 C5_2 C8_2 179.9 . . . . ?
C2_2 C1_2 C6_2 C5_2 -0.2 . . . . ?
B1_1 C1_2 C6_2 C5_2 172.6(3) . . . . ?
C2_2 C1_2 C6_2 C7_2 180.0 . . . . ?
B1_1 C1_2 C6_2 C7_2 -7.2(3) . . . . ?
C4_2 C5_2 C6_2 C1_2 0.1 . . . . ?
C8_2 C5_2 C6_2 C1_2 -179.8 . . . . ?
C4_2 C5_2 C6_2 C7_2 180.0 . . . . ?
C8_2 C5_2 C6_2 C7_2 0.0 . . . . ?


####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2263084'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki'
;University of Wurzburg
Germany
;
_audit_update_record             
;
2023-05-15 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;


_audit_creation_method           'CIF-fill 1.3q (K.Radacki, 2005-22)'
_audit_creation_date             2023-02-27
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C38 H56 B N'
_chemical_formula_sum            'C38 H56 B N'
_chemical_formula_weight         537.64
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   16.9907(2)
_cell_length_b                   10.55440(10)
_cell_length_c                   18.3576(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.4760(10)
_cell_angle_gamma                90
_cell_volume                     3271.00(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14735
_cell_measurement_theta_min      4.8340
_cell_measurement_theta_max      74.6260

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 Crystals were grown from saturated solution of C6D6 at 20 °C. For data 
 collection the crystal was immersed in a film of perfluoropolyether oil, 
 mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 1 0.0424
5 -3 9 0.0743
-4 3 -9 0.0706
-5 0 -10 0.0422
5 0 10 0.0725
-1 -6 -3 0.0789
1 6 3 0.0991
10 0 -6 0.0385
7 -4 -7 0.0528
5 1 10 0.0672
4 -1 -12 0.0350
-4 -1 -10 0.0459
10 -2 -3 0.0525

_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.961
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω   -122.00 -93.00   0.50    0.36    --  -79.50 -48.00 177.34   58
  2  ω   -128.00 -98.00   0.50    0.36    --  -79.50 -52.00 142.79   60
  3  ω   -101.00 -69.00   0.50    0.36    --  -54.00 -52.00 -11.07   64
  4  ω   -124.00 -99.00   0.50    0.36    --  -79.50 -65.00 -72.76   50
  5  ω   -107.00 -75.00   0.50    0.36    --  -62.00 -52.00-137.20   64
  6  ω    -68.00 -39.00   0.50    0.36    --  -22.00 -48.00-107.93   58
  7  ω    -78.00 -52.00   0.50    0.36    --  -79.50 111.00 -50.39   52
  8  ω    -85.00 -60.00   0.50    0.36    --  -69.45 130.00-132.00   50
  9  ω    -54.00 -20.00   0.50    0.36    --  -59.96 130.00-132.00   68
 10  ω    -61.00 -35.00   0.50    0.36    --  -76.35 130.00-132.00   52
 11  ω   -101.00 -67.00   0.50    0.36    --  -76.35 130.00-132.00   68
 12  ω    -97.00 -66.00   0.50    0.36    --  -78.00 114.00 130.94   62
 13  ω   -124.00 -98.00   0.50    0.36    --  -79.50-120.00 103.62   52
 14  ω     25.00  70.00   0.50    0.36    --   58.28-130.00 155.00   90
 15  ω     38.00  63.00   0.50    0.36    --   71.14-130.00 155.00   50
 16  ω     36.00  62.00   0.50    0.36    --   82.28-130.00 155.00   52
 17  ω     72.00  97.00   0.50    0.36    --   82.28-130.00 155.00   50
 18  ω     46.00 100.00   0.50    0.36    --   85.25-123.00 167.39  108
 19  ω     57.00  98.00   0.50    0.36    --   85.25-133.00 127.48   82
 20  ω     42.00  69.00   0.50    0.36    --   85.25-128.00 -20.28   54
 21  ω     62.00  99.00   0.50    0.36    --   85.25-121.00 -66.70   74
 22  ω     40.00  87.00   0.50    0.36    --   85.25-137.00-103.96   94
 23  ω     48.00  81.00   0.50    0.36    --   85.25-128.00-133.48   66
 24  ω     51.00  93.00   0.50    0.36    --   85.25-102.00-172.64   84
 25  ω     39.00  92.00   0.50    0.36    --   82.28-112.00-180.00  106
 26  ω     64.00  92.00   0.50    0.36    --   85.25-100.00-151.34   56
 27  ω     66.00  92.00   0.50    0.36    --   85.25 -99.00-127.20   52
 28  ω     65.00  91.00   0.50    0.36    --   85.25 -98.00 -63.67   52
 29  ω     65.00  91.00   0.50    0.36    --   85.25-100.00 -70.09   52
 30  ω     43.00  90.00   0.50    0.36    --   82.28 -95.00-120.00   94
 31  ω     46.00  71.00   0.50    0.36    --   85.25-105.00 -44.53   50
 32  ω     41.00  67.00   0.50    0.36    --   85.25-108.00  -5.32   52
 33  ω     20.00  59.00   0.50    0.36    --   58.28 -95.00  60.00   78
 34  ω     58.00  84.00   0.50    0.36    --   85.25  14.00  65.38   52
 35  ω     99.00 124.00   0.50    0.36    --   85.25  52.00 166.59   50
 36  ω     98.00 131.00   0.50    0.36    --   85.25  57.00  52.78   66
 37  ω     87.00 135.00   0.50    0.36    --   85.25  15.00 116.95   96
 38  ω     99.00 124.00   0.50    0.36    --   85.25  54.00  19.76   50
 39  ω     98.00 128.00   0.50    0.36    --   85.25  14.00  65.38   60
 40  ω     99.00 130.00   0.50    0.36    --   85.25  63.00 -46.56   62
 41  ω    101.00 132.00   0.50    0.36    --   85.25  47.00-106.90   62
 42  ω    102.00 127.00   0.50    0.36    --   85.25  60.00-151.38   50
 43  ω    102.00 127.00   0.50    0.36    --   85.25 116.00 -64.82   50
 44  ω    100.00 127.00   0.50    0.36    --   85.25 134.00  19.78   54
 45  ω    103.00 129.00   0.50    0.36    --   85.25 122.00-145.54   52
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0055210000
_diffrn_orient_matrix_UB_12      -0.1431105000
_diffrn_orient_matrix_UB_13      -0.0163019000
_diffrn_orient_matrix_UB_21      0.0467705000
_diffrn_orient_matrix_UB_22      -0.0281399000
_diffrn_orient_matrix_UB_23      0.0751334000
_diffrn_orient_matrix_UB_31      -0.0781542000
_diffrn_orient_matrix_UB_32      -0.0066793000
_diffrn_orient_matrix_UB_33      0.0349358000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            37012
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.841
_diffrn_reflns_theta_max         75.358
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6637
_reflns_number_gt                5692
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;

_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0586P)²+0.8946P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6637
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_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_
_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
N001 N 0.22559(5) 0.46044(9) 0.65208(5) 0.0180(2) Uani 1 1 d . . . . .
C002 C 0.14399(7) 0.43258(11) 0.66480(6) 0.0190(2) Uani 1 1 d . . . . .
C003 C 0.32652(7) 0.69400(11) 0.80737(6) 0.0194(2) Uani 1 1 d . . . . .
C004 C 0.08618(7) 0.52196(11) 0.63713(6) 0.0206(2) Uani 1 1 d . . . . .
C005 C 0.22356(7) 0.52557(11) 0.83739(6) 0.0208(2) Uani 1 1 d . . . . .
C006 C 0.12306(7) 0.31956(11) 0.69755(6) 0.0209(2) Uani 1 1 d . . . . .
C007 C 0.27712(7) 0.53360(10) 0.69257(6) 0.0182(2) Uani 1 1 d . . . . .
C008 C 0.37277(7) 0.46977(11) 0.80616(6) 0.0204(2) Uani 1 1 d . . . . .
C009 C 0.14170(7) 0.54526(12) 0.82367(7) 0.0237(3) Uani 1 1 d . . . . .
H009 H 0.120214 0.570662 0.775883 0.028 Uiso 1 1 calc R U . . .
C00A C 0.40127(7) 0.68135(11) 0.84086(6) 0.0199(2) Uani 1 1 d . . . . .
C00B C 0.42873(7) 0.54789(11) 0.83957(6) 0.0206(2) Uani 1 1 d . . . . .
C00C C 0.33459(7) 0.58876(11) 0.64034(6) 0.0209(2) Uani 1 1 d . . . . .
C00D C 0.04285(7) 0.29923(12) 0.70461(7) 0.0246(3) Uani 1 1 d . . . . .
H00D H 0.027428 0.223371 0.726975 0.030 Uiso 1 1 calc R U . . .
C00E C 0.25329(7) 0.41884(11) 0.57906(6) 0.0209(2) Uani 1 1 d . . . . .
C00F C 0.27986(7) 0.81622(11) 0.80533(6) 0.0224(2) Uani 1 1 d . . . . .
H00A H 0.236640 0.812144 0.764445 0.027 Uiso 1 1 calc R U . . .
H00B H 0.315137 0.887235 0.795274 0.027 Uiso 1 1 calc R U . . .
C00G C 0.00758(7) 0.49670(12) 0.64627(7) 0.0243(3) Uani 1 1 d . . . . .
H00G H -0.032093 0.556348 0.629045 0.029 Uiso 1 1 calc R U . . .
C00H C 0.10446(7) 0.64603(11) 0.59953(7) 0.0228(2) Uani 1 1 d . . . . .
H00H H 0.160205 0.641386 0.587127 0.027 Uiso 1 1 calc R U . . .
C00I C 0.38758(7) 0.32937(11) 0.79749(7) 0.0244(3) Uani 1 1 d . . . . .
H00C H 0.441506 0.317743 0.783028 0.029 Uiso 1 1 calc R U . . .
H00E H 0.349511 0.296523 0.757101 0.029 Uiso 1 1 calc R U . . .
C00J C 0.18146(7) 0.21828(11) 0.72614(7) 0.0236(3) Uani 1 1 d . . . . .
H00J H 0.235945 0.248677 0.719533 0.028 Uiso 1 1 calc R U . . .
C00K C 0.25080(7) 0.49460(12) 0.91065(7) 0.0252(3) Uani 1 1 d . . . . .
H00K H 0.306065 0.483268 0.923639 0.030 Uiso 1 1 calc R U . . .
C00L C 0.30470(7) 0.53168(11) 0.56448(6) 0.0222(2) Uani 1 1 d . . . . .
H00F H 0.273503 0.595127 0.533755 0.027 Uiso 1 1 calc R U . . .
H00I H 0.349958 0.504372 0.538709 0.027 Uiso 1 1 calc R U . . .
C00M C 0.30311(7) 0.29836(12) 0.59189(7) 0.0248(3) Uani 1 1 d . . . . .
H00L H 0.326293 0.276554 0.546999 0.037 Uiso 1 1 calc R U . . .
H00M H 0.269385 0.228612 0.605097 0.037 Uiso 1 1 calc R U . . .
H00N H 0.345551 0.312790 0.631785 0.037 Uiso 1 1 calc R U . . .
C00N C 0.51236(7) 0.51004(12) 0.86945(7) 0.0243(3) Uani 1 1 d . . . . .
H00O H 0.512658 0.419298 0.883144 0.029 Uiso 1 1 calc R U . . .
H00P H 0.528571 0.559453 0.914493 0.029 Uiso 1 1 calc R U . . .
C00O C 0.18598(7) 0.39393(12) 0.51888(6) 0.0252(3) Uani 1 1 d . . . . .
H00Q H 0.154795 0.471457 0.509283 0.038 Uiso 1 1 calc R U . . .
H00R H 0.151919 0.326554 0.534519 0.038 Uiso 1 1 calc R U . . .
H00S H 0.207854 0.367706 0.474072 0.038 Uiso 1 1 calc R U . . .
C00P C 0.45205(7) 0.78434(12) 0.87864(7) 0.0243(3) Uani 1 1 d . . . . .
H00T H 0.431464 0.867540 0.860321 0.029 Uiso 1 1 calc R U . . .
H00U H 0.506605 0.775572 0.865211 0.029 Uiso 1 1 calc R U . . .
C00Q C -0.01430(7) 0.38664(13) 0.67989(7) 0.0266(3) Uani 1 1 d . . . . .
H00V H -0.068312 0.371516 0.685860 0.032 Uiso 1 1 calc R U . . .
C00R C 0.32327(8) 0.73388(11) 0.63692(7) 0.0245(3) Uani 1 1 d . . . . .
H00W H 0.348545 0.768082 0.595711 0.037 Uiso 1 1 calc R U . . .
H00X H 0.347513 0.771937 0.682746 0.037 Uiso 1 1 calc R U . . .
H00Y H 0.266571 0.753724 0.630148 0.037 Uiso 1 1 calc R U . . .
C00S C 0.09051(8) 0.52924(13) 0.87695(7) 0.0296(3) Uani 1 1 d . . . . .
H00Z H 0.035225 0.541555 0.864592 0.035 Uiso 1 1 calc R U . . .
C00T C 0.42322(7) 0.56352(12) 0.66085(7) 0.0255(3) Uani 1 1 d . . . . .
H010 H 0.431952 0.472402 0.668169 0.038 Uiso 1 1 calc R U . . .
H011 H 0.441577 0.608805 0.706203 0.038 Uiso 1 1 calc R U . . .
H012 H 0.452768 0.593221 0.621270 0.038 Uiso 1 1 calc R U . . .
C00U C 0.57283(7) 0.53140(12) 0.81501(8) 0.0281(3) Uani 1 1 d . . . . .
H013 H 0.561436 0.474044 0.773174 0.042 Uiso 1 1 calc R U . . .
H014 H 0.626216 0.514518 0.839173 0.042 Uiso 1 1 calc R U . . .
H015 H 0.569610 0.619339 0.797798 0.042 Uiso 1 1 calc R U . . .
C00V C 0.20067(8) 0.47998(13) 0.96445(7) 0.0313(3) Uani 1 1 d . . . . .
H016 H 0.221974 0.459181 1.013058 0.038 Uiso 1 1 calc R U . . .
C00W C 0.11941(8) 0.49548(14) 0.94792(8) 0.0324(3) Uani 1 1 d . . . . .
H017 H 0.084571 0.483261 0.984308 0.039 Uiso 1 1 calc R U . . .
C00X C 0.38009(8) 0.25025(12) 0.86640(8) 0.0312(3) Uani 1 1 d . . . . .
H018 H 0.327121 0.261735 0.881692 0.047 Uiso 1 1 calc R U . . .
H019 H 0.420051 0.277851 0.905887 0.047 Uiso 1 1 calc R U . . .
H01A H 0.388303 0.160565 0.855667 0.047 Uiso 1 1 calc R U . . .
C00Y C 0.24414(8) 0.84351(13) 0.87644(7) 0.0315(3) Uani 1 1 d . . . . .
H01B H 0.211375 0.920018 0.870361 0.047 Uiso 1 1 calc R U . . .
H01C H 0.286787 0.856407 0.916343 0.047 Uiso 1 1 calc R U . . .
H01D H 0.211344 0.771614 0.888236 0.047 Uiso 1 1 calc R U . . .
C00Z C 0.05022(8) 0.66934(13) 0.52818(7) 0.0313(3) Uani 1 1 d . . . . .
H01E H 0.070293 0.741341 0.502065 0.047 Uiso 1 1 calc R U . . .
H01F H -0.003524 0.688013 0.539649 0.047 Uiso 1 1 calc R U . . .
H01G H 0.049240 0.593572 0.497232 0.047 Uiso 1 1 calc R U . . .
C010 C 0.09857(8) 0.75939(12) 0.65050(7) 0.0299(3) Uani 1 1 d . . . . .
H01H H 0.115141 0.836417 0.626614 0.045 Uiso 1 1 calc R U . . .
H01I H 0.133092 0.745489 0.696267 0.045 Uiso 1 1 calc R U . . .
H01J H 0.043686 0.768910 0.661285 0.045 Uiso 1 1 calc R U . . .
C011 C 0.17815(8) 0.19312(13) 0.80779(7) 0.0309(3) Uani 1 1 d . . . . .
H01K H 0.126425 0.157201 0.815060 0.046 Uiso 1 1 calc R U . . .
H01L H 0.185888 0.272836 0.835024 0.046 Uiso 1 1 calc R U . . .
H01M H 0.220020 0.133198 0.825588 0.046 Uiso 1 1 calc R U . . .
C012 C 0.16653(8) 0.09453(12) 0.68286(8) 0.0312(3) Uani 1 1 d . . . . .
H01N H 0.163196 0.112512 0.630224 0.047 Uiso 1 1 calc R U . . .
H01O H 0.116685 0.056649 0.694205 0.047 Uiso 1 1 calc R U . . .
H01P H 0.210192 0.035409 0.696502 0.047 Uiso 1 1 calc R U . . .
C013 C 0.45517(8) 0.78276(14) 0.96229(7) 0.0340(3) Uani 1 1 d . . . . .
H01Q H 0.401700 0.794899 0.976286 0.051 Uiso 1 1 calc R U . . .
H01R H 0.489671 0.851224 0.983036 0.051 Uiso 1 1 calc R U . . .
H01S H 0.476135 0.701153 0.981114 0.051 Uiso 1 1 calc R U . . .
B014 B 0.29122(8) 0.55454(12) 0.78240(7) 0.0191(3) Uani 1 1 d . . . . .


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
N001 C007 1.3299(14) . ?
N001 C002 1.4614(14) . ?
N001 C00E 1.5342(14) . ?
C002 C006 1.3997(16) . ?
C002 C004 1.4142(16) . ?
C003 C00A 1.3538(16) . ?
C003 C00F 1.5123(16) . ?
C003 B014 1.6354(17) . ?
C004 C00G 1.3905(17) . ?
C004 C00H 1.5284(16) . ?
C005 C009 1.4007(16) . ?
C005 C00K 1.4104(16) . ?
C005 B014 1.6419(17) . ?
C006 C00D 1.4001(17) . ?
C006 C00J 1.5117(16) . ?
C007 C00C 1.5567(16) . ?
C007 B014 1.6542(17) . ?
C008 C00B 1.3521(16) . ?
C008 C00I 1.5144(16) . ?
C008 B014 1.6656(17) . ?
C009 C00S 1.3905(18) . ?
C009 H009 0.9500 . ?
C00A C00B 1.4849(16) . ?
C00A C00P 1.5073(16) . ?
C00B C00N 1.5178(16) . ?
C00C C00T 1.5338(16) . ?
C00C C00R 1.5440(16) . ?
C00C C00L 1.5495(16) . ?
C00D C00Q 1.3785(18) . ?
C00D H00D 0.9500 . ?
C00E C00L 1.5185(16) . ?
C00E C00O 1.5206(16) . ?
C00E C00M 1.5311(16) . ?
C00F C00Y 1.5279(17) . ?
C00F H00A 0.9900 . ?
C00F H00B 0.9900 . ?
C00G C00Q 1.3858(18) . ?
C00G H00G 0.9500 . ?
C00H C010 1.5291(17) . ?
C00H C00Z 1.5340(17) . ?
C00H H00H 1.0000 . ?
C00I C00X 1.5330(18) . ?
C00I H00C 0.9900 . ?
C00I H00E 0.9900 . ?
C00J C011 1.5295(18) . ?
C00J C012 1.5350(17) . ?
C00J H00J 1.0000 . ?
C00K C00V 1.3836(18) . ?
C00K H00K 0.9500 . ?
C00L H00F 0.9900 . ?
C00L H00I 0.9900 . ?
C00M H00L 0.9800 . ?
C00M H00M 0.9800 . ?
C00M H00N 0.9800 . ?
C00N C00U 1.5287(18) . ?
C00N H00O 0.9900 . ?
C00N H00P 0.9900 . ?
C00O H00Q 0.9800 . ?
C00O H00R 0.9800 . ?
C00O H00S 0.9800 . ?
C00P C013 1.5306(18) . ?
C00P H00T 0.9900 . ?
C00P H00U 0.9900 . ?
C00Q H00V 0.9500 . ?
C00R H00W 0.9800 . ?
C00R H00X 0.9800 . ?
C00R H00Y 0.9800 . ?
C00S C00W 1.3861(19) . ?
C00S H00Z 0.9500 . ?
C00T H010 0.9800 . ?
C00T H011 0.9800 . ?
C00T H012 0.9800 . ?
C00U H013 0.9800 . ?
C00U H014 0.9800 . ?
C00U H015 0.9800 . ?
C00V C00W 1.3895(19) . ?
C00V H016 0.9500 . ?
C00W H017 0.9500 . ?
C00X H018 0.9800 . ?
C00X H019 0.9800 . ?
C00X H01A 0.9800 . ?
C00Y H01B 0.9800 . ?
C00Y H01C 0.9800 . ?
C00Y H01D 0.9800 . ?
C00Z H01E 0.9800 . ?
C00Z H01F 0.9800 . ?
C00Z H01G 0.9800 . ?
C010 H01H 0.9800 . ?
C010 H01I 0.9800 . ?
C010 H01J 0.9800 . ?
C011 H01K 0.9800 . ?
C011 H01L 0.9800 . ?
C011 H01M 0.9800 . ?
C012 H01N 0.9800 . ?
C012 H01O 0.9800 . ?
C012 H01P 0.9800 . ?
C013 H01Q 0.9800 . ?
C013 H01R 0.9800 . ?
C013 H01S 0.9800 . ?

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
C007 N001 C002 127.17(9) . . ?
C007 N001 C00E 114.02(9) . . ?
C002 N001 C00E 118.16(9) . . ?
C006 C002 C004 121.53(11) . . ?
C006 C002 N001 122.12(10) . . ?
C004 C002 N001 116.19(10) . . ?
C00A C003 C00F 123.90(10) . . ?
C00A C003 B014 109.52(10) . . ?
C00F C003 B014 125.88(10) . . ?
C00G C004 C002 117.80(11) . . ?
C00G C004 C00H 117.75(10) . . ?
C002 C004 C00H 124.43(10) . . ?
C009 C005 C00K 114.72(11) . . ?
C009 C005 B014 127.72(10) . . ?
C00K C005 B014 116.88(10) . . ?
C002 C006 C00D 117.88(11) . . ?
C002 C006 C00J 124.27(11) . . ?
C00D C006 C00J 117.85(11) . . ?
N001 C007 C00C 106.98(9) . . ?
N001 C007 B014 130.32(10) . . ?
C00C C007 B014 122.25(9) . . ?
C00B C008 C00I 121.85(11) . . ?
C00B C008 B014 108.23(10) . . ?
C00I C008 B014 129.88(10) . . ?
C00S C009 C005 122.87(11) . . ?
C00S C009 H009 118.6 . . ?
C005 C009 H009 118.6 . . ?
C003 C00A C00B 111.51(10) . . ?
C003 C00A C00P 126.64(11) . . ?
C00B C00A C00P 121.80(10) . . ?
C008 C00B C00A 112.31(10) . . ?
C008 C00B C00N 125.81(11) . . ?
C00A C00B C00N 121.80(10) . . ?
C00T C00C C00R 107.26(10) . . ?
C00T C00C C00L 111.48(10) . . ?
C00R C00C C00L 108.81(10) . . ?
C00T C00C C007 116.78(10) . . ?
C00R C00C C007 108.18(10) . . ?
C00L C00C C007 104.09(9) . . ?
C00Q C00D C006 121.58(12) . . ?
C00Q C00D H00D 119.2 . . ?
C006 C00D H00D 119.2 . . ?
C00L C00E C00O 114.08(10) . . ?
C00L C00E C00M 111.06(10) . . ?
C00O C00E C00M 109.00(10) . . ?
C00L C00E N001 99.72(9) . . ?
C00O C00E N001 113.86(9) . . ?
C00M C00E N001 108.79(9) . . ?
C003 C00F C00Y 113.41(10) . . ?
C003 C00F H00A 108.9 . . ?
C00Y C00F H00A 108.9 . . ?
C003 C00F H00B 108.9 . . ?
C00Y C00F H00B 108.9 . . ?
H00A C00F H00B 107.7 . . ?
C00Q C00G C004 121.60(11) . . ?
C00Q C00G H00G 119.2 . . ?
C004 C00G H00G 119.2 . . ?
C004 C00H C010 111.31(10) . . ?
C004 C00H C00Z 112.95(10) . . ?
C010 C00H C00Z 108.81(10) . . ?
C004 C00H H00H 107.9 . . ?
C010 C00H H00H 107.9 . . ?
C00Z C00H H00H 107.9 . . ?
C008 C00I C00X 114.59(11) . . ?
C008 C00I H00C 108.6 . . ?
C00X C00I H00C 108.6 . . ?
C008 C00I H00E 108.6 . . ?
C00X C00I H00E 108.6 . . ?
H00C C00I H00E 107.6 . . ?
C006 C00J C011 111.58(10) . . ?
C006 C00J C012 111.00(10) . . ?
C011 C00J C012 109.72(11) . . ?
C006 C00J H00J 108.1 . . ?
C011 C00J H00J 108.1 . . ?
C012 C00J H00J 108.1 . . ?
C00V C00K C005 122.98(12) . . ?
C00V C00K H00K 118.5 . . ?
C005 C00K H00K 118.5 . . ?
C00E C00L C00C 106.45(9) . . ?
C00E C00L H00F 110.4 . . ?
C00C C00L H00F 110.4 . . ?
C00E C00L H00I 110.4 . . ?
C00C C00L H00I 110.4 . . ?
H00F C00L H00I 108.6 . . ?
C00E C00M H00L 109.5 . . ?
C00E C00M H00M 109.5 . . ?
H00L C00M H00M 109.5 . . ?
C00E C00M H00N 109.5 . . ?
H00L C00M H00N 109.5 . . ?
H00M C00M H00N 109.5 . . ?
C00B C00N C00U 113.31(10) . . ?
C00B C00N H00O 108.9 . . ?
C00U C00N H00O 108.9 . . ?
C00B C00N H00P 108.9 . . ?
C00U C00N H00P 108.9 . . ?
H00O C00N H00P 107.7 . . ?
C00E C00O H00Q 109.5 . . ?
C00E C00O H00R 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
C00E C00O H00S 109.5 . . ?
H00Q C00O H00S 109.5 . . ?
H00R C00O H00S 109.5 . . ?
C00A C00P C013 114.02(11) . . ?
C00A C00P H00T 108.7 . . ?
C013 C00P H00T 108.7 . . ?
C00A C00P H00U 108.7 . . ?
C013 C00P H00U 108.7 . . ?
H00T C00P H00U 107.6 . . ?
C00D C00Q C00G 119.56(11) . . ?
C00D C00Q H00V 120.2 . . ?
C00G C00Q H00V 120.2 . . ?
C00C C00R H00W 109.5 . . ?
C00C C00R H00X 109.5 . . ?
H00W C00R H00X 109.5 . . ?
C00C C00R H00Y 109.5 . . ?
H00W C00R H00Y 109.5 . . ?
H00X C00R H00Y 109.5 . . ?
C00W C00S C009 120.59(12) . . ?
C00W C00S H00Z 119.7 . . ?
C009 C00S H00Z 119.7 . . ?
C00C C00T H010 109.5 . . ?
C00C C00T H011 109.5 . . ?
H010 C00T H011 109.5 . . ?
C00C C00T H012 109.5 . . ?
H010 C00T H012 109.5 . . ?
H011 C00T H012 109.5 . . ?
C00N C00U H013 109.5 . . ?
C00N C00U H014 109.5 . . ?
H013 C00U H014 109.5 . . ?
C00N C00U H015 109.5 . . ?
H013 C00U H015 109.5 . . ?
H014 C00U H015 109.5 . . ?
C00K C00V C00W 120.49(12) . . ?
C00K C00V H016 119.8 . . ?
C00W C00V H016 119.8 . . ?
C00S C00W C00V 118.27(12) . . ?
C00S C00W H017 120.9 . . ?
C00V C00W H017 120.9 . . ?
C00I C00X H018 109.5 . . ?
C00I C00X H019 109.5 . . ?
H018 C00X H019 109.5 . . ?
C00I C00X H01A 109.5 . . ?
H018 C00X H01A 109.5 . . ?
H019 C00X H01A 109.5 . . ?
C00F C00Y H01B 109.5 . . ?
C00F C00Y H01C 109.5 . . ?
H01B C00Y H01C 109.5 . . ?
C00F C00Y H01D 109.5 . . ?
H01B C00Y H01D 109.5 . . ?
H01C C00Y H01D 109.5 . . ?
C00H C00Z H01E 109.5 . . ?
C00H C00Z H01F 109.5 . . ?
H01E C00Z H01F 109.5 . . ?
C00H C00Z H01G 109.5 . . ?
H01E C00Z H01G 109.5 . . ?
H01F C00Z H01G 109.5 . . ?
C00H C010 H01H 109.5 . . ?
C00H C010 H01I 109.5 . . ?
H01H C010 H01I 109.5 . . ?
C00H C010 H01J 109.5 . . ?
H01H C010 H01J 109.5 . . ?
H01I C010 H01J 109.5 . . ?
C00J C011 H01K 109.5 . . ?
C00J C011 H01L 109.5 . . ?
H01K C011 H01L 109.5 . . ?
C00J C011 H01M 109.5 . . ?
H01K C011 H01M 109.5 . . ?
H01L C011 H01M 109.5 . . ?
C00J C012 H01N 109.5 . . ?
C00J C012 H01O 109.5 . . ?
H01N C012 H01O 109.5 . . ?
C00J C012 H01P 109.5 . . ?
H01N C012 H01P 109.5 . . ?
H01O C012 H01P 109.5 . . ?
C00P C013 H01Q 109.5 . . ?
C00P C013 H01R 109.5 . . ?
H01Q C013 H01R 109.5 . . ?
C00P C013 H01S 109.5 . . ?
H01Q C013 H01S 109.5 . . ?
H01R C013 H01S 109.5 . . ?
C003 B014 C005 104.80(9) . . ?
C003 B014 C007 114.01(9) . . ?
C005 B014 C007 123.72(10) . . ?
C003 B014 C008 98.17(9) . . ?
C005 B014 C008 111.01(9) . . ?
C007 B014 C008 102.24(9) . . ?

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
C007 N001 C002 C006 -99.96(14) . . . . ?
C00E N001 C002 C006 89.88(13) . . . . ?
C007 N001 C002 C004 84.67(14) . . . . ?
C00E N001 C002 C004 -85.49(12) . . . . ?
C006 C002 C004 C00G 2.72(17) . . . . ?
N001 C002 C004 C00G 178.12(10) . . . . ?
C006 C002 C004 C00H -178.87(11) . . . . ?
N001 C002 C004 C00H -3.47(16) . . . . ?
C004 C002 C006 C00D -2.25(17) . . . . ?
N001 C002 C006 C00D -177.38(10) . . . . ?
C004 C002 C006 C00J 178.06(11) . . . . ?
N001 C002 C006 C00J 2.93(17) . . . . ?
C002 N001 C007 C00C -151.45(10) . . . . ?
C00E N001 C007 C00C 19.06(12) . . . . ?
C002 N001 C007 B014 36.28(18) . . . . ?
C00E N001 C007 B014 -153.21(11) . . . . ?
C00K C005 C009 C00S -3.19(18) . . . . ?
B014 C005 C009 C00S -173.34(12) . . . . ?
C00F C003 C00A C00B 174.77(10) . . . . ?
B014 C003 C00A C00B 3.87(13) . . . . ?
C00F C003 C00A C00P -2.62(19) . . . . ?
B014 C003 C00A C00P -173.52(11) . . . . ?
C00I C008 C00B C00A 179.30(10) . . . . ?
B014 C008 C00B C00A -2.75(13) . . . . ?
C00I C008 C00B C00N 2.56(19) . . . . ?
B014 C008 C00B C00N -179.49(11) . . . . ?
C003 C00A C00B C008 -0.69(14) . . . . ?
C00P C00A C00B C008 176.85(11) . . . . ?
C003 C00A C00B C00N 176.20(10) . . . . ?
C00P C00A C00B C00N -6.26(17) . . . . ?
N001 C007 C00C C00T -123.48(11) . . . . ?
B014 C007 C00C C00T 49.55(15) . . . . ?
N001 C007 C00C C00R 115.49(10) . . . . ?
B014 C007 C00C C00R -71.48(13) . . . . ?
N001 C007 C00C C00L -0.14(12) . . . . ?
B014 C007 C00C C00L 172.90(10) . . . . ?
C002 C006 C00D C00Q 0.41(18) . . . . ?
C00J C006 C00D C00Q -179.88(11) . . . . ?
C007 N001 C00E C00L -29.81(12) . . . . ?
C002 N001 C00E C00L 141.62(10) . . . . ?
C007 N001 C00E C00O -151.71(10) . . . . ?
C002 N001 C00E C00O 19.72(14) . . . . ?
C007 N001 C00E C00M 86.51(11) . . . . ?
C002 N001 C00E C00M -102.06(11) . . . . ?
C00A C003 C00F C00Y -78.78(15) . . . . ?
B014 C003 C00F C00Y 90.61(14) . . . . ?
C002 C004 C00G C00Q -1.36(17) . . . . ?
C00H C004 C00G C00Q -179.88(11) . . . . ?
C00G C004 C00H C010 74.30(13) . . . . ?
C002 C004 C00H C010 -104.12(13) . . . . ?
C00G C004 C00H C00Z -48.46(15) . . . . ?
C002 C004 C00H C00Z 133.13(12) . . . . ?
C00B C008 C00I C00X 79.40(15) . . . . ?
B014 C008 C00I C00X -98.06(14) . . . . ?
C002 C006 C00J C011 121.46(12) . . . . ?
C00D C006 C00J C011 -58.23(14) . . . . ?
C002 C006 C00J C012 -115.83(13) . . . . ?
C00D C006 C00J C012 64.48(14) . . . . ?
C009 C005 C00K C00V 2.31(18) . . . . ?
B014 C005 C00K C00V 173.59(12) . . . . ?
C00O C00E C00L C00C 148.68(10) . . . . ?
C00M C00E C00L C00C -87.66(11) . . . . ?
N001 C00E C00L C00C 26.93(11) . . . . ?
C00T C00C C00L C00E 108.64(11) . . . . ?
C00R C00C C00L C00E -133.27(10) . . . . ?
C007 C00C C00L C00E -18.09(12) . . . . ?
C008 C00B C00N C00U 94.00(15) . . . . ?
C00A C00B C00N C00U -82.45(14) . . . . ?
C003 C00A C00P C013 100.87(14) . . . . ?
C00B C00A C00P C013 -76.27(14) . . . . ?
C006 C00D C00Q C00G 0.91(19) . . . . ?
C004 C00G C00Q C00D -0.41(19) . . . . ?
C005 C009 C00S C00W 1.7(2) . . . . ?
C005 C00K C00V C00W 0.1(2) . . . . ?
C009 C00S C00W C00V 0.9(2) . . . . ?
C00K C00V C00W C00S -1.8(2) . . . . ?
C00A C003 B014 C005 109.44(11) . . . . ?
C00F C003 B014 C005 -61.23(14) . . . . ?
C00A C003 B014 C007 -112.29(11) . . . . ?
C00F C003 B014 C007 77.04(14) . . . . ?
C00A C003 B014 C008 -4.92(12) . . . . ?
C00F C003 B014 C008 -175.59(10) . . . . ?
C009 C005 B014 C003 96.45(13) . . . . ?
C00K C005 B014 C003 -73.52(12) . . . . ?
C009 C005 B014 C007 -36.58(18) . . . . ?
C00K C005 B014 C007 153.45(11) . . . . ?
C009 C005 B014 C008 -158.54(11) . . . . ?
C00K C005 B014 C008 31.48(14) . . . . ?
N001 C007 B014 C003 -151.74(11) . . . . ?
C00C C007 B014 C003 37.01(14) . . . . ?
N001 C007 B014 C005 -22.43(18) . . . . ?
C00C C007 B014 C005 166.32(10) . . . . ?
N001 C007 B014 C008 103.43(13) . . . . ?
C00C C007 B014 C008 -67.81(12) . . . . ?
C00B C008 B014 C003 4.47(12) . . . . ?
C00I C008 B014 C003 -177.80(11) . . . . ?
C00B C008 B014 C005 -104.89(11) . . . . ?
C00I C008 B014 C005 72.84(15) . . . . ?
C00B C008 B014 C007 121.33(10) . . . . ?
C00I C008 B014 C007 -60.94(15) . . . . ?


####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2263085'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Radacki'
;University of Wurzburg
Germany
;
_audit_update_record             
;
2023-05-15 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;



_audit_creation_method           'CIF-fill 1.3q (K.Radacki, 2005-22)'
_audit_creation_date             2023-01-30
_shelx_SHELXL_version_number     2019/2
_chemical_formula_moiety         'C39 H58 B N'
_chemical_formula_sum            'C39 H58 B N'
_chemical_formula_weight         551.67
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_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.
;
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                   17.1660(2)
_cell_length_b                   10.52710(10)
_cell_length_c                   18.3364(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.4030(10)
_cell_angle_gamma                90
_cell_volume                     3292.87(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18297
_cell_measurement_theta_min      4.8470
_cell_measurement_theta_max      74.9700

_exptl_crystal_description       block
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.457
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_preparation       
;
 Crystals were grown from saturated solution. For data collection the crystal 
 was immersed in a film of perfluoropolyether oil, mounted on a polyimide 
 loop and transferred to stream of cold nitrogen (Oxford Cryostream 800).
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0381
-1 0 1 0.0545
0 0 -1 0.0569
0 0 1 0.0892
1 0 1 0.0874
-1 0 -1 0.0800
1 0 0 0.0653
-1 0 0 0.0743
-1 1 -1 0.0577
1 -1 1 0.0689
0 1 -1 0.0421
1 1 -1 0.0266
-1 -1 1 0.0396
0 1 0 0.0345
1 -1 -1 0.0312
-1 1 1 0.0312
1 1 0 0.0424
-1 -1 0 0.0508
0 1 1 0.0459
0 -1 -1 0.0422
1 1 1 0.0500
-1 -1 -1 0.0562

_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.973
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  ω   -120.00 -92.00   0.50    0.20    --  -79.50 -63.00 -51.88   56
  2  ω   -105.00 -80.00   0.50    0.20    --  -62.00 -52.00-112.36   50
  3  ω   -119.00 -93.00   0.50    0.20    --  -79.50 -57.00-131.36   52
  4  ω    -99.00 -68.00   0.50    0.20    --  -54.00 -49.00 -32.95   62
  5  ω   -113.00 -81.00   0.50    0.20    --  -66.00 -47.00  17.19   64
  6  ω   -118.00 -92.00   0.50    0.20    --  -74.00 -56.00-158.03   52
  7  ω   -128.00 -96.00   0.50    0.20    --  -79.50 -50.00-175.53   64
  8  ω    -97.00 -55.00   0.50    0.20    --  -79.50 115.00-161.92   84
  9  ω     -6.00  19.00   0.50    0.20    --  -10.00  78.00 131.87   50
 10  ω    -82.00 -56.00   0.50    0.20    --  -69.76 113.00 -83.00   52
 11  ω    -86.00 -61.00   0.50    0.20    --  -76.35 113.00 -83.00   50
 12  ω    -78.00 -18.00   0.50    0.20    --  -60.16 113.00 -83.00  120
 13  ω   -125.00 -87.00   0.50    0.20    --  -79.50-133.00  14.36   76
 14  ω     46.00 100.00   0.50    0.20    --   85.25-125.00 -25.78  108
 15  ω     41.00  81.00   0.50    0.20    --   85.25-138.00-159.93   80
 16  ω     56.00  97.00   0.50    0.20    --   85.25-114.00-114.56   82
 17  ω     75.00 101.00   0.50    0.20    --   85.25-126.00 -44.84   52
 18  ω     38.00  80.00   0.50    0.20    --   85.25-127.00  95.87   84
 19  ω     43.00  86.00   0.50    0.20    --   85.25-123.00 139.72   86
 20  ω     56.00  82.00   0.50    0.20    --   85.25-119.00 110.25   52
 21  ω     66.00  91.00   0.50    0.20    --   82.28-112.00  90.00   50
 22  ω     37.00  62.00   0.50    0.20    --   82.28-112.00  60.00   50
 23  ω     43.00  69.00   0.50    0.20    --   85.25-112.00 -26.16   52
 24  ω     41.00  66.00   0.50    0.20    --   82.28-113.00-175.00   50
 25  ω     67.00  93.00   0.50    0.20    --   85.25-106.00-166.57   52
 26  ω     47.00  78.00   0.50    0.20    --   71.34-113.00-175.00   62
 27  ω     21.00  46.00   0.50    0.20    --   58.57-113.00-175.00   50
 28  ω     43.00  93.00   0.50    0.20    --   85.25 -97.00-163.82  100
 29  ω     64.00  89.00   0.50    0.20    --   82.28 -95.00-120.00   50
 30  ω     60.00  86.00   0.50    0.20    --   85.25 -85.00-134.88   52
 31  ω     19.00  46.00   0.50    0.20    --   58.57 -95.00 -90.00   54
 32  ω     46.00  71.00   0.50    0.20    --   85.25 -82.00-100.99   50
 33  ω     42.00  70.00   0.50    0.20    --   82.28 -95.00 -30.00   56
 34  ω     44.00  70.00   0.50    0.20    --   85.25 -72.00 -33.40   52
 35  ω     46.00  73.00   0.50    0.20    --   85.25 -85.00   9.40   54
 36  ω     51.00  84.00   0.50    0.20    --   85.25 -88.00  29.57   66
 37  ω     42.00  91.00   0.50    0.20    --   85.25 -99.00 156.61   98
 38  ω     99.00 134.00   0.50    0.20    --   85.25  38.00  11.34   70
 39  ω     98.00 127.00   0.50    0.20    --   85.25  53.00-154.12   58
 40  ω    102.00 128.00   0.50    0.20    --   85.25  56.00 -46.09   52
 41  ω    100.00 128.00   0.50    0.20    --   85.25  64.00 116.39   56
 42  ω    104.00 130.00   0.50    0.20    --   85.25 117.00 157.94   52
 43  ω     92.00 117.00   0.50    0.20    --   85.25 135.00  51.19   50
 44  ω     98.00 123.00   0.50    0.20    --   85.25 122.00  16.76   50
 45  ω     96.00 129.00   0.50    0.20    --   85.25 127.00-108.55   66
;
_diffrn_orient_matrix_type       
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0360101000
_diffrn_orient_matrix_UB_12      0.0918867000
_diffrn_orient_matrix_UB_13      -0.0598767000
_diffrn_orient_matrix_UB_21      0.0092347000
_diffrn_orient_matrix_UB_22      0.1106791000
_diffrn_orient_matrix_UB_23      0.0554133000
_diffrn_orient_matrix_UB_31      0.0822139000
_diffrn_orient_matrix_UB_32      0.0278270000
_diffrn_orient_matrix_UB_33      -0.0220868000
_diffrn_detector                 HPA
_diffrn_detector_type            'HyPix Arc150'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            36724
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.852
_diffrn_reflns_theta_max         70.070
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6242
_reflns_number_gt                5531
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;

_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0497P)²+1.0040P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6242
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_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_
_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
B1_1 B 0.29262(7) 0.55480(12) 0.79142(6) 0.0165(2) Uani 1 1 d . . . . .
C2_1 C 0.32795(6) 0.69440(11) 0.81401(6) 0.0175(2) Uani 1 1 d . . . . .
C3_1 C 0.40371(6) 0.68282(11) 0.84358(6) 0.0176(2) Uani 1 1 d . . . . .
C4_1 C 0.43080(6) 0.54915(11) 0.84064(6) 0.0184(2) Uani 1 1 d . . . . .
C5_1 C 0.37388(6) 0.47031(11) 0.81068(6) 0.0174(2) Uani 1 1 d . . . . .
C6_1 C 0.28113(7) 0.81610(11) 0.81277(6) 0.0204(2) Uani 1 1 d . . . . .
H6A_1 H 0.237072 0.810593 0.773164 0.024 Uiso 1 1 calc R U . . .
H6B_1 H 0.315043 0.887580 0.800971 0.024 Uiso 1 1 calc R U . . .
C7_1 C 0.24831(8) 0.84466(13) 0.88511(7) 0.0303(3) Uani 1 1 d . . . . .
H7A_1 H 0.216134 0.921704 0.879702 0.046 Uiso 1 1 calc R U . . .
H7B_1 H 0.291683 0.857489 0.923893 0.046 Uiso 1 1 calc R U . . .
H7C_1 H 0.216049 0.773112 0.898125 0.046 Uiso 1 1 calc R U . . .
C8_1 C 0.45598(7) 0.78793(11) 0.87654(6) 0.0218(2) Uani 1 1 d . . . . .
H8A_1 H 0.434641 0.870176 0.857241 0.026 Uiso 1 1 calc R U . . .
H8B_1 H 0.508596 0.777502 0.860055 0.026 Uiso 1 1 calc R U . . .
C9_1 C 0.46491(8) 0.79328(13) 0.96071(7) 0.0302(3) Uani 1 1 d . . . . .
H9A_1 H 0.500557 0.862613 0.977560 0.045 Uiso 1 1 calc R U . . .
H9B_1 H 0.486340 0.712554 0.980579 0.045 Uiso 1 1 calc R U . . .
H9C_1 H 0.413550 0.808098 0.977717 0.045 Uiso 1 1 calc R U . . .
C10_1 C 0.51376(6) 0.51070(12) 0.86893(6) 0.0215(2) Uani 1 1 d . . . . .
H10A_1 H 0.514014 0.419713 0.882617 0.026 Uiso 1 1 calc R U . . .
H10B_1 H 0.530710 0.560019 0.913884 0.026 Uiso 1 1 calc R U . . .
C11_1 C 0.57311(7) 0.53163(12) 0.81329(7) 0.0245(3) Uani 1 1 d . . . . .
H11A_1 H 0.626153 0.514556 0.836854 0.037 Uiso 1 1 calc R U . . .
H11B_1 H 0.569845 0.619722 0.795938 0.037 Uiso 1 1 calc R U . . .
H11C_1 H 0.561187 0.473967 0.771580 0.037 Uiso 1 1 calc R U . . .
C12_1 C 0.38871(7) 0.33050(11) 0.79812(6) 0.0212(2) Uani 1 1 d . . . . .
H12A_1 H 0.442624 0.321048 0.784511 0.025 Uiso 1 1 calc R U . . .
H12B_1 H 0.352213 0.301788 0.755708 0.025 Uiso 1 1 calc R U . . .
C13_1 C 0.37963(8) 0.24202(12) 0.86290(7) 0.0279(3) Uani 1 1 d . . . . .
H13A_1 H 0.384769 0.153587 0.847446 0.042 Uiso 1 1 calc R U . . .
H13B_1 H 0.327887 0.254688 0.879556 0.042 Uiso 1 1 calc R U . . .
H13C_1 H 0.420408 0.261165 0.903160 0.042 Uiso 1 1 calc R U . . .
C1_2 C 0.22372(6) 0.52799(10) 0.84578(6) 0.0176(2) Uani 1 1 d . . . . .
C2_2 C 0.23867(7) 0.49967(11) 0.92217(6) 0.0205(2) Uani 1 1 d . . . . .
C3_2 C 0.17617(7) 0.47751(12) 0.96334(7) 0.0264(3) Uani 1 1 d . . . . .
H3_2 H 0.187515 0.455326 1.013625 0.032 Uiso 1 1 calc R U . . .
C4_2 C 0.09847(7) 0.48650(13) 0.93401(7) 0.0301(3) Uani 1 1 d . . . . .
H4_2 H 0.057270 0.466379 0.962597 0.036 Uiso 1 1 calc R U . . .
C5_2 C 0.08263(7) 0.52553(12) 0.86207(7) 0.0263(3) Uani 1 1 d . . . . .
H5_2 H 0.030013 0.537771 0.841121 0.032 Uiso 1 1 calc R U . . .
C6_2 C 0.14432(7) 0.54681(11) 0.82047(6) 0.0204(2) Uani 1 1 d . . . . .
H6_2 H 0.131890 0.576106 0.771552 0.024 Uiso 1 1 calc R U . . .
C7_2 C 0.31883(7) 0.50057(13) 0.96560(6) 0.0249(3) Uani 1 1 d . . . . .
H7A_2 H 0.313444 0.487060 1.017677 0.037 Uiso 1 1 calc R U . . .
H7B_2 H 0.344132 0.582699 0.959340 0.037 Uiso 1 1 calc R U . . .
H7C_2 H 0.350895 0.432547 0.947941 0.037 Uiso 1 1 calc R U . . .
C1_3 C 0.27692(6) 0.53424(10) 0.70009(6) 0.0158(2) Uani 1 1 d . . . . .
N2_3 N 0.22636(5) 0.46115(9) 0.65887(5) 0.0159(2) Uani 1 1 d . . . . .
C3_3 C 0.25448(6) 0.41987(11) 0.58569(6) 0.0187(2) Uani 1 1 d . . . . .
C4_3 C 0.30451(7) 0.53387(11) 0.57140(6) 0.0198(2) Uani 1 1 d . . . . .
H4A_3 H 0.273228 0.597091 0.540732 0.024 Uiso 1 1 calc R U . . .
H4B_3 H 0.349522 0.507540 0.545562 0.024 Uiso 1 1 calc R U . . .
C5_3 C 0.33362(6) 0.59126(11) 0.64732(6) 0.0183(2) Uani 1 1 d . . . . .
C6_3 C 0.18845(7) 0.39339(12) 0.52500(6) 0.0222(3) Uani 1 1 d . . . . .
H6A_3 H 0.210720 0.367265 0.480399 0.033 Uiso 1 1 calc R U . . .
H6B_3 H 0.157113 0.470525 0.514995 0.033 Uiso 1 1 calc R U . . .
H6C_3 H 0.155023 0.325327 0.540557 0.033 Uiso 1 1 calc R U . . .
C7_3 C 0.30438(7) 0.29992(11) 0.59867(6) 0.0226(3) Uani 1 1 d . . . . .
H7A_3 H 0.325693 0.276230 0.553166 0.034 Uiso 1 1 calc R U . . .
H7B_3 H 0.271854 0.230476 0.614015 0.034 Uiso 1 1 calc R U . . .
H7C_3 H 0.347575 0.316204 0.637157 0.034 Uiso 1 1 calc R U . . .
C8_3 C 0.42176(6) 0.56923(12) 0.66602(6) 0.0227(3) Uani 1 1 d . . . . .
H8A_3 H 0.449564 0.599721 0.625553 0.034 Uiso 1 1 calc R U . . .
H8B_3 H 0.431800 0.478263 0.673515 0.034 Uiso 1 1 calc R U . . .
H8C_3 H 0.440323 0.615614 0.710959 0.034 Uiso 1 1 calc R U . . .
C9_3 C 0.32071(7) 0.73637(11) 0.64373(6) 0.0222(2) Uani 1 1 d . . . . .
H9A_3 H 0.344323 0.771171 0.601759 0.033 Uiso 1 1 calc R U . . .
H9B_3 H 0.345229 0.775472 0.689091 0.033 Uiso 1 1 calc R U . . .
H9C_3 H 0.264367 0.754577 0.638058 0.033 Uiso 1 1 calc R U . . .
C1_4 C 0.14496(6) 0.43122(11) 0.66909(6) 0.0168(2) Uani 1 1 d . . . . .
C2_4 C 0.12407(6) 0.31818(11) 0.70210(6) 0.0187(2) Uani 1 1 d . . . . .
C3_4 C 0.04443(7) 0.29559(12) 0.70588(6) 0.0230(3) Uani 1 1 d . . . . .
H3_4 H 0.029014 0.219485 0.728130 0.028 Uiso 1 1 calc R U . . .
C4_4 C -0.01239(7) 0.38059(12) 0.67823(7) 0.0247(3) Uani 1 1 d . . . . .
H4_4 H -0.066153 0.363449 0.681873 0.030 Uiso 1 1 calc R U . . .
C5_4 C 0.00952(7) 0.49112(12) 0.64512(6) 0.0223(3) Uani 1 1 d . . . . .
H5_4 H -0.029862 0.549476 0.626195 0.027 Uiso 1 1 calc R U . . .
C6_4 C 0.08777(6) 0.51902(11) 0.63883(6) 0.0186(2) Uani 1 1 d . . . . .
C7_4 C 0.18207(7) 0.21984(11) 0.73470(6) 0.0209(2) Uani 1 1 d . . . . .
H7_4 H 0.236195 0.251752 0.730192 0.025 Uiso 1 1 calc R U . . .
C8_4 C 0.17117(8) 0.09322(12) 0.69333(7) 0.0281(3) Uani 1 1 d . . . . .
H8A_4 H 0.214683 0.036128 0.709836 0.042 Uiso 1 1 calc R U . . .
H8B_4 H 0.170263 0.108507 0.640525 0.042 Uiso 1 1 calc R U . . .
H8C_4 H 0.121595 0.054182 0.703226 0.042 Uiso 1 1 calc R U . . .
C9_4 C 0.17422(7) 0.19804(12) 0.81628(7) 0.0267(3) Uani 1 1 d . . . . .
H9A_4 H 0.213456 0.135941 0.836281 0.040 Uiso 1 1 calc R U . . .
H9B_4 H 0.121628 0.165814 0.821730 0.040 Uiso 1 1 calc R U . . .
H9C_4 H 0.182575 0.278453 0.842936 0.040 Uiso 1 1 calc R U . . .
C10_4 C 0.10619(7) 0.64386(11) 0.60177(6) 0.0201(2) Uani 1 1 d . . . . .
H10_4 H 0.161775 0.639863 0.590404 0.024 Uiso 1 1 calc R U . . .
C11_4 C 0.09855(7) 0.75844(12) 0.65198(7) 0.0256(3) Uani 1 1 d . . . . .
H11A_4 H 0.113459 0.835875 0.627317 0.038 Uiso 1 1 calc R U . . .
H11B_4 H 0.133137 0.746962 0.697755 0.038 Uiso 1 1 calc R U . . .
H11C_4 H 0.044163 0.765781 0.662996 0.038 Uiso 1 1 calc R U . . .
C12_4 C 0.05380(8) 0.66667(13) 0.52930(7) 0.0281(3) Uani 1 1 d . . . . .
H12A_4 H 0.074411 0.738337 0.503241 0.042 Uiso 1 1 calc R U . . .
H12B_4 H 0.000311 0.685930 0.539771 0.042 Uiso 1 1 calc R U . . .
H12C_4 H 0.053299 0.590272 0.498709 0.042 Uiso 1 1 calc R U . . .


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
B1_1 C2_1 1.6257(17) . ?
B1_1 C1_2 1.6538(16) . ?
B1_1 C5_1 1.6588(16) . ?
B1_1 C1_3 1.6803(16) . ?
C2_1 C3_1 1.3575(16) . ?
C2_1 C6_1 1.5113(15) . ?
C3_1 C4_1 1.4848(16) . ?
C3_1 C8_1 1.5078(16) . ?
C4_1 C5_1 1.3512(16) . ?
C4_1 C10_1 1.5153(15) . ?
C5_1 C12_1 1.5157(16) . ?
C6_1 C7_1 1.5277(16) . ?
C8_1 C9_1 1.5349(16) . ?
C10_1 C11_1 1.5360(16) . ?
C12_1 C13_1 1.5310(16) . ?
C1_2 C6_2 1.4039(16) . ?
C1_2 C2_2 1.4272(15) . ?
C2_2 C3_2 1.3987(16) . ?
C2_2 C7_2 1.5110(16) . ?
C3_2 C4_2 1.3846(18) . ?
C4_2 C5_2 1.3794(18) . ?
C5_2 C6_2 1.3907(16) . ?
C1_3 N2_3 1.3305(14) . ?
C1_3 C5_3 1.5666(14) . ?
N2_3 C1_4 1.4646(14) . ?
N2_3 C3_3 1.5385(13) . ?
C3_3 C4_3 1.5155(16) . ?
C3_3 C6_3 1.5230(15) . ?
C3_3 C7_3 1.5296(16) . ?
C4_3 C5_3 1.5484(15) . ?
C5_3 C8_3 1.5313(15) . ?
C5_3 C9_3 1.5439(16) . ?
C1_4 C2_4 1.3997(16) . ?
C1_4 C6_4 1.4159(16) . ?
C2_4 C3_4 1.3968(16) . ?
C2_4 C7_4 1.5125(16) . ?
C3_4 C4_4 1.3779(17) . ?
C4_4 C5_4 1.3837(18) . ?
C5_4 C6_4 1.3924(16) . ?
C6_4 C10_4 1.5286(16) . ?
C7_4 C9_4 1.5341(16) . ?
C7_4 C8_4 1.5347(17) . ?
C10_4 C11_4 1.5319(16) . ?
C10_4 C12_4 1.5381(15) . ?

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_1 B1_1 C1_2 105.80(9) . . ?
C2_1 B1_1 C5_1 98.60(8) . . ?
C1_2 B1_1 C5_1 114.90(9) . . ?
C2_1 B1_1 C1_3 112.60(9) . . ?
C1_2 B1_1 C1_3 122.18(9) . . ?
C5_1 B1_1 C1_3 100.42(8) . . ?
C3_1 C2_1 C6_1 124.50(10) . . ?
C3_1 C2_1 B1_1 109.52(10) . . ?
C6_1 C2_1 B1_1 125.44(9) . . ?
C2_1 C3_1 C4_1 111.14(10) . . ?
C2_1 C3_1 C8_1 126.50(11) . . ?
C4_1 C3_1 C8_1 122.36(10) . . ?
C5_1 C4_1 C3_1 112.43(10) . . ?
C5_1 C4_1 C10_1 125.77(11) . . ?
C3_1 C4_1 C10_1 121.80(10) . . ?
C4_1 C5_1 C12_1 122.15(10) . . ?
C4_1 C5_1 B1_1 108.06(10) . . ?
C12_1 C5_1 B1_1 129.78(10) . . ?
C2_1 C6_1 C7_1 113.62(10) . . ?
C3_1 C8_1 C9_1 114.72(10) . . ?
C4_1 C10_1 C11_1 113.70(9) . . ?
C5_1 C12_1 C13_1 116.07(10) . . ?
C6_2 C1_2 C2_2 114.56(10) . . ?
C6_2 C1_2 B1_1 120.66(10) . . ?
C2_2 C1_2 B1_1 124.38(10) . . ?
C3_2 C2_2 C1_2 119.98(11) . . ?
C3_2 C2_2 C7_2 115.15(10) . . ?
C1_2 C2_2 C7_2 124.72(10) . . ?
C4_2 C3_2 C2_2 122.86(11) . . ?
C5_2 C4_2 C3_2 118.07(11) . . ?
C4_2 C5_2 C6_2 119.44(11) . . ?
C5_2 C6_2 C1_2 124.51(11) . . ?
N2_3 C1_3 C5_3 106.36(9) . . ?
N2_3 C1_3 B1_1 131.50(9) . . ?
C5_3 C1_3 B1_1 121.64(9) . . ?
C1_3 N2_3 C1_4 128.53(9) . . ?
C1_3 N2_3 C3_3 114.24(9) . . ?
C1_4 N2_3 C3_3 116.58(8) . . ?
C4_3 C3_3 C6_3 114.12(9) . . ?
C4_3 C3_3 C7_3 111.24(9) . . ?
C6_3 C3_3 C7_3 108.72(10) . . ?
C4_3 C3_3 N2_3 99.56(8) . . ?
C6_3 C3_3 N2_3 114.12(9) . . ?
C7_3 C3_3 N2_3 108.79(9) . . ?
C3_3 C4_3 C5_3 106.61(9) . . ?
C8_3 C5_3 C9_3 107.04(9) . . ?
C8_3 C5_3 C4_3 110.73(9) . . ?
C9_3 C5_3 C4_3 108.50(9) . . ?
C8_3 C5_3 C1_3 118.04(9) . . ?
C9_3 C5_3 C1_3 108.02(9) . . ?
C4_3 C5_3 C1_3 104.20(9) . . ?
C2_4 C1_4 C6_4 121.64(10) . . ?
C2_4 C1_4 N2_3 122.17(10) . . ?
C6_4 C1_4 N2_3 116.04(10) . . ?
C3_4 C2_4 C1_4 117.75(11) . . ?
C3_4 C2_4 C7_4 117.95(10) . . ?
C1_4 C2_4 C7_4 124.30(10) . . ?
C4_4 C3_4 C2_4 121.85(11) . . ?
C3_4 C4_4 C5_4 119.44(11) . . ?
C4_4 C5_4 C6_4 121.71(11) . . ?
C5_4 C6_4 C1_4 117.58(11) . . ?
C5_4 C6_4 C10_4 117.87(10) . . ?
C1_4 C6_4 C10_4 124.52(10) . . ?
C2_4 C7_4 C9_4 111.23(10) . . ?
C2_4 C7_4 C8_4 111.13(10) . . ?
C9_4 C7_4 C8_4 109.44(10) . . ?
C6_4 C10_4 C11_4 111.96(9) . . ?
C6_4 C10_4 C12_4 112.85(10) . . ?
C11_4 C10_4 C12_4 108.38(10) . . ?

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_2 B1_1 C2_1 C3_1 114.13(10) . . . . ?
C5_1 B1_1 C2_1 C3_1 -4.91(11) . . . . ?
C1_3 B1_1 C2_1 C3_1 -110.04(10) . . . . ?
C1_2 B1_1 C2_1 C6_1 -57.70(13) . . . . ?
C5_1 B1_1 C2_1 C6_1 -176.73(9) . . . . ?
C1_3 B1_1 C2_1 C6_1 78.14(13) . . . . ?
C6_1 C2_1 C3_1 C4_1 175.98(9) . . . . ?
B1_1 C2_1 C3_1 C4_1 4.06(12) . . . . ?
C6_1 C2_1 C3_1 C8_1 -3.40(17) . . . . ?
B1_1 C2_1 C3_1 C8_1 -175.32(10) . . . . ?
C2_1 C3_1 C4_1 C5_1 -1.09(13) . . . . ?
C8_1 C3_1 C4_1 C5_1 178.32(10) . . . . ?
C2_1 C3_1 C4_1 C10_1 178.93(10) . . . . ?
C8_1 C3_1 C4_1 C10_1 -1.65(16) . . . . ?
C3_1 C4_1 C5_1 C12_1 176.71(9) . . . . ?
C10_1 C4_1 C5_1 C12_1 -3.32(17) . . . . ?
C3_1 C4_1 C5_1 B1_1 -2.33(12) . . . . ?
C10_1 C4_1 C5_1 B1_1 177.64(10) . . . . ?
C2_1 B1_1 C5_1 C4_1 4.21(11) . . . . ?
C1_2 B1_1 C5_1 C4_1 -107.73(11) . . . . ?
C1_3 B1_1 C5_1 C4_1 119.24(9) . . . . ?
C2_1 B1_1 C5_1 C12_1 -174.73(10) . . . . ?
C1_2 B1_1 C5_1 C12_1 73.32(14) . . . . ?
C1_3 B1_1 C5_1 C12_1 -59.71(13) . . . . ?
C3_1 C2_1 C6_1 C7_1 -80.36(14) . . . . ?
B1_1 C2_1 C6_1 C7_1 90.28(13) . . . . ?
C2_1 C3_1 C8_1 C9_1 100.53(13) . . . . ?
C4_1 C3_1 C8_1 C9_1 -78.80(13) . . . . ?
C5_1 C4_1 C10_1 C11_1 96.67(14) . . . . ?
C3_1 C4_1 C10_1 C11_1 -83.36(13) . . . . ?
C4_1 C5_1 C12_1 C13_1 86.68(13) . . . . ?
B1_1 C5_1 C12_1 C13_1 -94.50(13) . . . . ?
C2_1 B1_1 C1_2 C6_2 99.64(11) . . . . ?
C5_1 B1_1 C1_2 C6_2 -152.74(10) . . . . ?
C1_3 B1_1 C1_2 C6_2 -30.89(16) . . . . ?
C2_1 B1_1 C1_2 C2_2 -72.70(13) . . . . ?
C5_1 B1_1 C1_2 C2_2 34.92(15) . . . . ?
C1_3 B1_1 C1_2 C2_2 156.77(11) . . . . ?
C6_2 C1_2 C2_2 C3_2 7.72(16) . . . . ?
B1_1 C1_2 C2_2 C3_2 -179.52(11) . . . . ?
C6_2 C1_2 C2_2 C7_2 -167.53(11) . . . . ?
B1_1 C1_2 C2_2 C7_2 5.22(18) . . . . ?
C1_2 C2_2 C3_2 C4_2 -2.60(19) . . . . ?
C7_2 C2_2 C3_2 C4_2 173.09(12) . . . . ?
C2_2 C3_2 C4_2 C5_2 -3.5(2) . . . . ?
C3_2 C4_2 C5_2 C6_2 3.9(2) . . . . ?
C4_2 C5_2 C6_2 C1_2 1.87(19) . . . . ?
C2_2 C1_2 C6_2 C5_2 -7.58(17) . . . . ?
B1_1 C1_2 C6_2 C5_2 179.37(11) . . . . ?
C2_1 B1_1 C1_3 N2_3 -152.63(11) . . . . ?
C1_2 B1_1 C1_3 N2_3 -25.02(17) . . . . ?
C5_1 B1_1 C1_3 N2_3 103.41(12) . . . . ?
C2_1 B1_1 C1_3 C5_3 36.68(13) . . . . ?
C1_2 B1_1 C1_3 C5_3 164.29(10) . . . . ?
C5_1 B1_1 C1_3 C5_3 -67.27(12) . . . . ?
C5_3 C1_3 N2_3 C1_4 -150.51(10) . . . . ?
B1_1 C1_3 N2_3 C1_4 37.75(18) . . . . ?
C5_3 C1_3 N2_3 C3_3 19.82(12) . . . . ?
B1_1 C1_3 N2_3 C3_3 -151.93(11) . . . . ?
C1_3 N2_3 C3_3 C4_3 -30.56(11) . . . . ?
C1_4 N2_3 C3_3 C4_3 140.99(9) . . . . ?
C1_3 N2_3 C3_3 C6_3 -152.52(10) . . . . ?
C1_4 N2_3 C3_3 C6_3 19.03(14) . . . . ?
C1_3 N2_3 C3_3 C7_3 85.89(11) . . . . ?
C1_4 N2_3 C3_3 C7_3 -102.56(11) . . . . ?
C6_3 C3_3 C4_3 C5_3 149.14(9) . . . . ?
C7_3 C3_3 C4_3 C5_3 -87.41(11) . . . . ?
N2_3 C3_3 C4_3 C5_3 27.17(11) . . . . ?
C3_3 C4_3 C5_3 C8_3 109.90(10) . . . . ?
C3_3 C4_3 C5_3 C9_3 -132.91(10) . . . . ?
C3_3 C4_3 C5_3 C1_3 -18.00(11) . . . . ?
N2_3 C1_3 C5_3 C8_3 -123.94(10) . . . . ?
B1_1 C1_3 C5_3 C8_3 48.80(14) . . . . ?
N2_3 C1_3 C5_3 C9_3 114.57(10) . . . . ?
B1_1 C1_3 C5_3 C9_3 -72.69(12) . . . . ?
N2_3 C1_3 C5_3 C4_3 -0.68(11) . . . . ?
B1_1 C1_3 C5_3 C4_3 172.06(9) . . . . ?
C1_3 N2_3 C1_4 C2_4 -98.41(14) . . . . ?
C3_3 N2_3 C1_4 C2_4 91.46(12) . . . . ?
C1_3 N2_3 C1_4 C6_4 86.04(13) . . . . ?
C3_3 N2_3 C1_4 C6_4 -84.10(12) . . . . ?
C6_4 C1_4 C2_4 C3_4 -1.45(16) . . . . ?
N2_3 C1_4 C2_4 C3_4 -176.76(10) . . . . ?
C6_4 C1_4 C2_4 C7_4 179.32(10) . . . . ?
N2_3 C1_4 C2_4 C7_4 4.01(16) . . . . ?
C1_4 C2_4 C3_4 C4_4 0.09(17) . . . . ?
C7_4 C2_4 C3_4 C4_4 179.37(11) . . . . ?
C2_4 C3_4 C4_4 C5_4 0.59(18) . . . . ?
C3_4 C4_4 C5_4 C6_4 0.07(18) . . . . ?
C4_4 C5_4 C6_4 C1_4 -1.36(16) . . . . ?
C4_4 C5_4 C6_4 C10_4 -179.65(10) . . . . ?
C2_4 C1_4 C6_4 C5_4 2.07(16) . . . . ?
N2_3 C1_4 C6_4 C5_4 177.65(9) . . . . ?
C2_4 C1_4 C6_4 C10_4 -179.77(10) . . . . ?
N2_3 C1_4 C6_4 C10_4 -4.18(15) . . . . ?
C3_4 C2_4 C7_4 C9_4 -58.00(14) . . . . ?
C1_4 C2_4 C7_4 C9_4 121.23(12) . . . . ?
C3_4 C2_4 C7_4 C8_4 64.22(13) . . . . ?
C1_4 C2_4 C7_4 C8_4 -116.56(12) . . . . ?
C5_4 C6_4 C10_4 C11_4 75.41(13) . . . . ?
C1_4 C6_4 C10_4 C11_4 -102.76(12) . . . . ?
C5_4 C6_4 C10_4 C12_4 -47.19(14) . . . . ?
C1_4 C6_4 C10_4 C12_4 134.64(11) . . . . ?


