# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# 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_hexamer
_database_code_depnum_ccdc_archive 'CCDC 2284250'
loop_
_audit_author_name
_audit_author_address
'Pierre Thuery'
;CEA Saclay
France
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT910_hexamer             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         17 Note  
RESPONSE: Some reflections had to be deleted from the data set for this
rather low-quality and poorly diffracting crystal.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C94 H170 B6 O16'
_chemical_formula_weight         1621.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5184(6)
_cell_length_b                   14.6526(7)
_cell_length_c                   16.1480(9)
_cell_angle_alpha                97.730(3)
_cell_angle_beta                 108.931(2)
_cell_angle_gamma                98.573(3)
_cell_volume                     2500.0(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    123007
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      25.68

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_special_details           'crystal-to-detector distance 30 mm'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'2 φ and 11 ω scans with 2° steps (672 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            123007
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.008
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9438
_reflns_number_gt                7006
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by intrinsic phasing and subsequent difference Fourier
 synthesis. Both THF solvent molecules are disordered over two positions 
 sharing either two or one C atom, which have been refined with occupancy
 parameters constrained to sum to unity. All non-hydrogen atoms were
 refined with anisotropic displacement parameters, with restraints for
 bond lengths and displacement parameters for the two disordered THF
 molecules. The H atoms were introduced at calculated positions and were
 treated as riding atoms with an isotropic displacement parameter equal to
 1.2 times that of the parent atom. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1126P)²+0.5003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9438
_refine_ls_number_parameters     588
_refine_ls_number_restraints     212
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.2003
_refine_ls_wR_factor_gt          0.1854
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.47012(12) 0.23120(8) 0.37864(8) 0.0452(3) Uani 1 1 d . . . . .
O2 O 0.45372(11) 0.34135(8) 0.30089(8) 0.0409(3) Uani 1 1 d . . . . .
O3 O 0.45373(12) 0.49058(8) 0.25324(8) 0.0408(3) Uani 1 1 d . . . . .
O4 O 0.46819(14) 0.61472(8) 0.35259(8) 0.0499(3) Uani 1 1 d . . . . .
O5 O 0.48822(12) 0.78237(8) 0.37264(8) 0.0426(3) Uani 1 1 d . . . . .
O6 O 0.50196(12) 0.85690(8) 0.50268(8) 0.0439(3) Uani 1 1 d . . . . .
B1 B 0.4967(2) 0.13288(14) 0.40033(13) 0.0433(5) Uani 1 1 d . . . . .
B2 B 0.4446(2) 0.38468(14) 0.21638(13) 0.0403(4) Uani 1 1 d . . . . .
B3 B 0.4603(2) 0.69423(13) 0.29690(13) 0.0395(4) Uani 1 1 d . . . . .
C1 C 0.48178(17) 0.26332(12) 0.31278(11) 0.0406(4) Uani 1 1 d . . . . .
H1 H 0.5115 0.2290 0.2724 0.049 Uiso 1 1 calc R U . . .
C2 C 0.46470(19) 0.52829(12) 0.32931(12) 0.0453(4) Uani 1 1 d . . . . .
H2 H 0.4709 0.4899 0.3729 0.054 Uiso 1 1 calc R U . . .
C3 C 0.48831(16) 0.78167(12) 0.44977(11) 0.0396(4) Uani 1 1 d . . . . .
H3 H 0.4779 0.7234 0.4688 0.048 Uiso 1 1 calc R U . . .
C4 C 0.63289(19) 0.12334(12) 0.39990(13) 0.0465(4) Uani 1 1 d . . . . .
H4 H 0.6298 0.1197 0.3369 0.056 Uiso 1 1 calc R U . . .
C5 C 0.7380(2) 0.20751(15) 0.45737(16) 0.0596(5) Uani 1 1 d . . . . .
H5A H 0.7182 0.2655 0.4358 0.072 Uiso 1 1 calc R U . . .
H5B H 0.7407 0.2149 0.5198 0.072 Uiso 1 1 calc R U . . .
C6 C 0.8665(2) 0.19698(19) 0.4554(2) 0.0765(7) Uani 1 1 d . . . . .
H6A H 0.8675 0.1976 0.3944 0.092 Uiso 1 1 calc R U . . .
H6B H 0.9306 0.2511 0.4965 0.092 Uiso 1 1 calc R U . . .
C7 C 0.8992(3) 0.1063(2) 0.4827(2) 0.0878(8) Uani 1 1 d . . . . .
H7A H 0.9097 0.1093 0.5464 0.105 Uiso 1 1 calc R U . . .
H7B H 0.9798 0.0990 0.4756 0.105 Uiso 1 1 calc R U . . .
C8 C 0.7970(3) 0.02163(19) 0.4260(2) 0.0817(8) Uani 1 1 d . . . . .
H8A H 0.7945 0.0139 0.3636 0.098 Uiso 1 1 calc R U . . .
H8B H 0.8176 -0.0358 0.4483 0.098 Uiso 1 1 calc R U . . .
C9 C 0.6690(2) 0.03247(15) 0.42827(17) 0.0594(5) Uani 1 1 d . . . . .
H9A H 0.6688 0.0324 0.4895 0.071 Uiso 1 1 calc R U . . .
H9B H 0.6051 -0.0222 0.3880 0.071 Uiso 1 1 calc R U . . .
C10 C 0.37592(19) 0.05274(13) 0.34141(12) 0.0483(5) Uani 1 1 d . . . . .
H10 H 0.3879 -0.0053 0.3667 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3623(3) 0.02672(16) 0.24290(14) 0.0661(6) Uani 1 1 d . . . . .
H11A H 0.4385 0.0056 0.2391 0.079 Uiso 1 1 calc R U . . .
H11B H 0.3553 0.0832 0.2157 0.079 Uiso 1 1 calc R U . . .
C12 C 0.2464(3) -0.05178(19) 0.18988(18) 0.0860(9) Uani 1 1 d . . . . .
H12A H 0.2377 -0.0629 0.1261 0.103 Uiso 1 1 calc R U . . .
H12B H 0.2588 -0.1108 0.2118 0.103 Uiso 1 1 calc R U . . .
C13 C 0.1274(3) -0.0276(2) 0.19829(19) 0.0882(9) Uani 1 1 d . . . . .
H13A H 0.0566 -0.0814 0.1664 0.106 Uiso 1 1 calc R U . . .
H13B H 0.1093 0.0271 0.1701 0.106 Uiso 1 1 calc R U . . .
C14 C 0.1392(2) -0.0046(2) 0.29512(19) 0.0814(8) Uani 1 1 d . . . . .
H14A H 0.1483 -0.0614 0.3216 0.098 Uiso 1 1 calc R U . . .
H14B H 0.0620 0.0146 0.2990 0.098 Uiso 1 1 calc R U . . .
C15 C 0.2520(2) 0.07434(17) 0.34790(17) 0.0656(6) Uani 1 1 d . . . . .
H15A H 0.2593 0.0854 0.4114 0.079 Uiso 1 1 calc R U . . .
H15B H 0.2380 0.1329 0.3255 0.079 Uiso 1 1 calc R U . . .
C16 C 0.5629(2) 0.37796(14) 0.18613(14) 0.0512(5) Uani 1 1 d . . . . .
H16 H 0.5583 0.3097 0.1650 0.061 Uiso 1 1 calc R U . . .
C17 C 0.5561(3) 0.42671(18) 0.10673(19) 0.0790(8) Uani 1 1 d . . . . .
H17A H 0.4764 0.3983 0.0569 0.095 Uiso 1 1 calc R U . . .
H17B H 0.5565 0.4942 0.1245 0.095 Uiso 1 1 calc R U . . .
C18 C 0.6664(4) 0.4177(2) 0.0749(3) 0.1122(13) Uani 1 1 d . . . . .
H18A H 0.6588 0.3509 0.0490 0.135 Uiso 1 1 calc R U . . .
H18B H 0.6627 0.4546 0.0274 0.135 Uiso 1 1 calc R U . . .
C19 C 0.7917(5) 0.4521(3) 0.1500(4) 0.143(2) Uani 1 1 d . . . . .
H19A H 0.8048 0.5210 0.1701 0.171 Uiso 1 1 calc R U . . .
H19B H 0.8595 0.4398 0.1277 0.171 Uiso 1 1 calc R U . . .
C20 C 0.7990(3) 0.4041(3) 0.2286(3) 0.1196(14) Uani 1 1 d . . . . .
H20A H 0.8794 0.4316 0.2779 0.143 Uiso 1 1 calc R U . . .
H20B H 0.7963 0.3362 0.2106 0.143 Uiso 1 1 calc R U . . .
C21 C 0.6906(2) 0.4157(2) 0.2608(2) 0.0756(7) Uani 1 1 d . . . . .
H21A H 0.6980 0.4833 0.2838 0.091 Uiso 1 1 calc R U . . .
H21B H 0.6958 0.3819 0.3105 0.091 Uiso 1 1 calc R U . . .
C22 C 0.30657(18) 0.34523(13) 0.14401(12) 0.0463(4) Uani 1 1 d . . . . .
H22 H 0.2922 0.3901 0.1020 0.056 Uiso 1 1 calc R U . . .
C23 C 0.2921(2) 0.24809(15) 0.08708(15) 0.0603(6) Uani 1 1 d . . . . .
H23A H 0.3563 0.2515 0.0585 0.072 Uiso 1 1 calc R U . . .
H23B H 0.3067 0.2014 0.1264 0.072 Uiso 1 1 calc R U . . .
C24 C 0.1619(3) 0.21522(19) 0.01491(18) 0.0806(8) Uani 1 1 d . . . . .
H24A H 0.1509 0.2575 -0.0288 0.097 Uiso 1 1 calc R U . . .
H24B H 0.1546 0.1509 -0.0173 0.097 Uiso 1 1 calc R U . . .
C25 C 0.0600(3) 0.2150(2) 0.0550(2) 0.0875(9) Uani 1 1 d . . . . .
H25A H 0.0647 0.1668 0.0928 0.105 Uiso 1 1 calc R U . . .
H25B H -0.0229 0.1977 0.0064 0.105 Uiso 1 1 calc R U . . .
C26 C 0.0716(2) 0.31023(18) 0.11099(18) 0.0727(7) Uani 1 1 d . . . . .
H26A H 0.0070 0.3060 0.1393 0.087 Uiso 1 1 calc R U . . .
H26B H 0.0570 0.3573 0.0721 0.087 Uiso 1 1 calc R U . . .
C27 C 0.20169(19) 0.34195(16) 0.18318(14) 0.0557(5) Uani 1 1 d . . . . .
H27A H 0.2125 0.2981 0.2254 0.067 Uiso 1 1 calc R U . . .
H27B H 0.2084 0.4053 0.2170 0.067 Uiso 1 1 calc R U . . .
C28 C 0.57115(17) 0.70647(13) 0.25746(12) 0.0430(4) Uani 1 1 d . . . . .
H28 H 0.5559 0.6479 0.2125 0.052 Uiso 1 1 calc R U . . .
C29 C 0.5713(2) 0.78883(16) 0.20796(16) 0.0608(6) Uani 1 1 d . . . . .
H29A H 0.5845 0.8483 0.2501 0.073 Uiso 1 1 calc R U . . .
H29B H 0.4887 0.7803 0.1601 0.073 Uiso 1 1 calc R U . . .
C30 C 0.6748(3) 0.7954(2) 0.1670(2) 0.0828(8) Uani 1 1 d . . . . .
H30A H 0.6571 0.7385 0.1206 0.099 Uiso 1 1 calc R U . . .
H30B H 0.6748 0.8508 0.1379 0.099 Uiso 1 1 calc R U . . .
C31 C 0.8030(3) 0.8042(2) 0.2371(2) 0.0876(9) Uani 1 1 d . . . . .
H31A H 0.8665 0.8041 0.2080 0.105 Uiso 1 1 calc R U . . .
H31B H 0.8251 0.8649 0.2796 0.105 Uiso 1 1 calc R U . . .
C32 C 0.8055(2) 0.7247(2) 0.2874(2) 0.0801(8) Uani 1 1 d . . . . .
H32A H 0.8879 0.7355 0.3360 0.096 Uiso 1 1 calc R U . . .
H32B H 0.7952 0.6650 0.2465 0.096 Uiso 1 1 calc R U . . .
C33 C 0.70224(19) 0.71607(17) 0.32710(15) 0.0602(5) Uani 1 1 d . . . . .
H33A H 0.7194 0.7724 0.3740 0.072 Uiso 1 1 calc R U . . .
H33B H 0.7036 0.6604 0.3557 0.072 Uiso 1 1 calc R U . . .
C34 C 0.31932(17) 0.68710(13) 0.23163(13) 0.0460(4) Uani 1 1 d . . . . .
H34 H 0.3168 0.7504 0.2153 0.055 Uiso 1 1 calc R U . . .
C35 C 0.2196(2) 0.6699(2) 0.27394(17) 0.0823(8) Uani 1 1 d . . . . .
H35A H 0.2426 0.7182 0.3289 0.099 Uiso 1 1 calc R U . . .
H35B H 0.2176 0.6076 0.2912 0.099 Uiso 1 1 calc R U . . .
C36 C 0.0884(2) 0.6733(2) 0.2111(2) 0.0907(9) Uani 1 1 d . . . . .
H36A H 0.0265 0.6579 0.2402 0.109 Uiso 1 1 calc R U . . .
H36B H 0.0873 0.7377 0.1991 0.109 Uiso 1 1 calc R U . . .
C37 C 0.0521(2) 0.60510(19) 0.12464(18) 0.0731(7) Uani 1 1 d . . . . .
H37A H -0.0302 0.6118 0.0840 0.088 Uiso 1 1 calc R U . . .
H37B H 0.0434 0.5401 0.1358 0.088 Uiso 1 1 calc R U . . .
C38 C 0.1486(2) 0.6218(2) 0.08079(17) 0.0715(7) Uani 1 1 d . . . . .
H38A H 0.1511 0.6844 0.0640 0.086 Uiso 1 1 calc R U . . .
H38B H 0.1245 0.5737 0.0256 0.086 Uiso 1 1 calc R U . . .
C39 C 0.2775(2) 0.61711(16) 0.14318(13) 0.0561(5) Uani 1 1 d . . . . .
H39A H 0.3392 0.6302 0.1134 0.067 Uiso 1 1 calc R U . . .
H39B H 0.2763 0.5526 0.1554 0.067 Uiso 1 1 calc R U . . .
O7A O 0.3364(5) 0.4485(3) 0.4652(4) 0.0920(13) Uani 0.603(7) 1 d D U P . .
O7B O 0.3008(9) 0.4686(6) 0.4793(8) 0.128(3) Uani 0.397(7) 1 d D U P . .
C40A C 0.2786(5) 0.5249(4) 0.4834(4) 0.0848(15) Uani 0.603(7) 1 d D U P . .
H40A H 0.3155 0.5565 0.5470 0.102 Uiso 0.603(7) 1 d R U P . .
H40B H 0.2870 0.5713 0.4454 0.102 Uiso 0.603(7) 1 d R U P . .
C40B C 0.1858(10) 0.5096(7) 0.4711(9) 0.118(3) Uani 0.397(7) 1 d D U P . .
H40C H 0.1498 0.5261 0.4140 0.141 Uiso 0.397(7) 1 d R U P . .
H40D H 0.2025 0.5631 0.5178 0.141 Uiso 0.397(7) 1 d R U P . .
C41A C 0.1391(7) 0.4736(5) 0.4478(8) 0.147(3) Uani 0.603(7) 1 d D U P . .
H41A H 0.0823 0.5031 0.4041 0.177 Uiso 0.603(7) 1 d R U P . .
H41B H 0.1149 0.4767 0.5015 0.177 Uiso 0.603(7) 1 d R U P . .
C41B C 0.1037(10) 0.4261(6) 0.4835(7) 0.122(3) Uani 0.397(7) 1 d D U P . .
H41C H 0.0177 0.4306 0.4710 0.146 Uiso 0.397(7) 1 d R U P . .
H41D H 0.1379 0.4080 0.5401 0.146 Uiso 0.397(7) 1 d R U P . .
C42 C 0.1276(4) 0.3688(4) 0.4114(4) 0.1689(19) Uani 1 1 d D U . . .
H42A H 0.0829 0.3245 0.4375 0.203 Uiso 0.603(7) 1 d R U P . .
H42B H 0.0848 0.3557 0.3458 0.203 Uiso 0.603(7) 1 d R U P . .
H42C H 0.1066 0.3972 0.3597 0.203 Uiso 0.397(7) 1 d R U P . .
H42D H 0.0770 0.3065 0.3959 0.203 Uiso 0.397(7) 1 d R U P . .
C43 C 0.2598(4) 0.3650(3) 0.4407(2) 0.1077(10) Uani 1 1 d D U . . .
H43A H 0.2817 0.3282 0.4887 0.129 Uiso 0.603(7) 1 d R U P . .
H43B H 0.2734 0.3316 0.3882 0.129 Uiso 0.603(7) 1 d R U P . .
H43C H 0.2819 0.3274 0.4855 0.129 Uiso 0.397(7) 1 d R U P . .
H43D H 0.2888 0.3456 0.3930 0.129 Uiso 0.397(7) 1 d R U P . .
O8A O 0.2954(13) 0.8711(8) 0.8163(7) 0.203(3) Uani 0.532(8) 1 d D U P . .
O8B O 0.3718(12) 0.8547(7) 0.8378(7) 0.166(3) Uani 0.468(8) 1 d D U P . .
C44A C 0.4093(13) 0.8948(11) 0.8951(9) 0.180(3) Uani 0.532(8) 1 d D U P . .
H44A H 0.4635 0.9557 0.9100 0.216 Uiso 0.532(8) 1 d R U P . .
H44B H 0.4597 0.8478 0.9033 0.216 Uiso 0.532(8) 1 d R U P . .
C44B C 0.4043(11) 0.8604(9) 0.9333(7) 0.162(3) Uani 0.468(8) 1 d D U P . .
H44C H 0.4799 0.9114 0.9607 0.194 Uiso 0.468(8) 1 d R U P . .
H44D H 0.4297 0.8012 0.9480 0.194 Uiso 0.468(8) 1 d R U P . .
C45A C 0.3550(12) 0.8998(11) 0.9687(9) 0.195(3) Uani 0.532(8) 1 d D U P . .
H45A H 0.3985 0.9305 1.0299 0.234 Uiso 0.532(8) 1 d R U P . .
H45B H 0.3129 0.8369 0.9651 0.234 Uiso 0.532(8) 1 d R U P . .
C45B C 0.2933(14) 0.8639(11) 0.9634(10) 0.181(3) Uani 0.468(8) 1 d D U P . .
H45C H 0.3443 0.9133 1.0129 0.217 Uiso 0.468(8) 1 d R U P . .
H45D H 0.2511 0.8162 0.9851 0.217 Uiso 0.468(8) 1 d R U P . .
C46 C 0.2449(8) 0.9388(6) 0.9170(6) 0.214(2) Uani 1 1 d D U . . .
H46A H 0.2875 1.0033 0.9289 0.257 Uiso 0.532(8) 1 d R U P . .
H46B H 0.1708 0.9368 0.9323 0.257 Uiso 0.532(8) 1 d R U P . .
H46C H 0.2465 1.0037 0.9376 0.257 Uiso 0.468(8) 1 d R U P . .
H46D H 0.1613 0.9028 0.9008 0.257 Uiso 0.468(8) 1 d R U P . .
C47A C 0.1842(14) 0.8942(10) 0.8236(8) 0.210(4) Uani 0.532(8) 1 d D U P . .
H47A H 0.1161 0.8406 0.8049 0.252 Uiso 0.532(8) 1 d R U P . .
H47B H 0.1625 0.9390 0.7859 0.252 Uiso 0.532(8) 1 d R U P . .
C47B C 0.3019(19) 0.9297(11) 0.8410(10) 0.199(3) Uani 0.468(8) 1 d D U P . .
H47C H 0.2314 0.9112 0.7861 0.238 Uiso 0.468(8) 1 d R U P . .
H47D H 0.3483 0.9895 0.8402 0.238 Uiso 0.468(8) 1 d R U P . .


_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 C1 1.257(2) . ?
O1 B1 1.578(2) . ?
O2 C1 1.256(2) . ?
O2 B2 1.561(2) . ?
O3 C2 1.235(2) . ?
O3 B2 1.561(2) . ?
O4 C2 1.262(2) . ?
O4 B3 1.560(2) . ?
O5 C3 1.247(2) . ?
O5 B3 1.569(2) . ?
O6 C3 1.256(2) . ?
O6 B1 1.548(2) 2_666 ?
B1 O6 1.548(2) 2_666 ?
B1 C4 1.598(3) . ?
B1 C10 1.604(3) . ?
B2 C16 1.601(3) . ?
B2 C22 1.602(3) . ?
B3 C28 1.600(3) . ?
B3 C34 1.602(3) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C9 1.536(3) . ?
C4 C5 1.538(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.517(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.524(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.519(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.536(3) . ?
C10 C15 1.540(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.541(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.508(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.511(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.533(3) . ?
C16 C17 1.536(3) . ?
C16 H16 1.0000 . ?
C17 C18 1.534(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.513(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.517(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.523(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.532(3) . ?
C22 C23 1.541(3) . ?
C22 H22 1.0000 . ?
C23 C24 1.529(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.513(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.519(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.528(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.535(3) . ?
C28 C33 1.535(3) . ?
C28 H28 1.0000 . ?
C29 C30 1.538(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.516(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.506(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.520(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.523(3) . ?
C34 C39 1.528(3) . ?
C34 H34 1.0000 . ?
C35 C36 1.535(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.497(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.507(4) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.518(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
O7A C43 1.324(5) . ?
O7A C40A 1.429(6) . ?
O7B C43 1.503(8) . ?
O7B C40B 1.509(9) . ?
C40A C41A 1.550(7) . ?
C40A H40A 0.9898 . ?
C40A H40B 0.9902 . ?
C40B C41B 1.510(9) . ?
C40B H40C 0.9600 . ?
C40B H40D 0.9601 . ?
C41A C42 1.538(5) . ?
C41A H41A 0.9899 . ?
C41A H41B 0.9902 . ?
C41B C42 1.466(5) . ?
C41B H41C 0.9600 . ?
C41B H41D 0.9600 . ?
C42 C43 1.453(4) . ?
C42 H42A 0.9901 . ?
C42 H42B 0.9899 . ?
C42 H42C 0.9600 . ?
C42 H42D 0.9600 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9902 . ?
C43 H43C 0.9600 . ?
C43 H43D 0.9599 . ?
O8A C47A 1.409(9) . ?
O8A C44A 1.458(9) . ?
O8B C44B 1.452(5) . ?
O8B C47B 1.461(9) . ?
C44A C45A 1.510(9) . ?
C44A H44A 0.9598 . ?
C44A H44B 0.9601 . ?
C44B C45B 1.514(5) . ?
C44B H44C 0.9899 . ?
C44B H44D 0.9900 . ?
C45A C46 1.514(5) . ?
C45A H45A 0.9600 . ?
C45A H45B 0.9601 . ?
C45B C46 1.486(8) . ?
C45B H45C 0.9600 . ?
C45B H45D 0.9600 . ?
C46 C47A 1.451(9) . ?
C46 C47B 1.569(8) . ?
C46 H46A 0.9602 . ?
C46 H46B 0.9599 . ?
C46 H46C 0.9599 . ?
C46 H46D 0.9600 . ?
C47A H47A 0.9601 . ?
C47A H47B 0.9599 . ?
C47B H47C 0.9600 . ?
C47B H47D 0.9601 . ?

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
C1 O1 B1 125.10(14) . . ?
C1 O2 B2 125.80(14) . . ?
C2 O3 B2 128.39(14) . . ?
C2 O4 B3 129.80(14) . . ?
C3 O5 B3 126.56(13) . . ?
C3 O6 B1 126.84(14) . 2_666 ?
O6 B1 O1 101.18(13) 2_666 . ?
O6 B1 C4 109.10(15) 2_666 . ?
O1 B1 C4 109.71(15) . . ?
O6 B1 C10 105.79(15) 2_666 . ?
O1 B1 C10 108.70(15) . . ?
C4 B1 C10 120.58(16) . . ?
O3 B2 O2 101.28(13) . . ?
O3 B2 C16 107.49(15) . . ?
O2 B2 C16 112.11(15) . . ?
O3 B2 C22 107.35(14) . . ?
O2 B2 C22 108.31(15) . . ?
C16 B2 C22 118.75(16) . . ?
O4 B3 O5 100.15(13) . . ?
O4 B3 C28 111.66(14) . . ?
O5 B3 C28 107.38(14) . . ?
O4 B3 C34 111.16(15) . . ?
O5 B3 C34 105.55(14) . . ?
C28 B3 C34 118.93(15) . . ?
O2 C1 O1 119.25(16) . . ?
O2 C1 H1 120.4 . . ?
O1 C1 H1 120.4 . . ?
O3 C2 O4 123.95(16) . . ?
O3 C2 H2 118.0 . . ?
O4 C2 H2 118.0 . . ?
O5 C3 O6 120.96(15) . . ?
O5 C3 H3 119.5 . . ?
O6 C3 H3 119.5 . . ?
C9 C4 C5 108.88(17) . . ?
C9 C4 B1 112.26(16) . . ?
C5 C4 B1 114.18(16) . . ?
C9 C4 H4 107.0 . . ?
C5 C4 H4 107.0 . . ?
B1 C4 H4 107.0 . . ?
C6 C5 C4 113.15(19) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 111.5(2) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 111.0(2) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 111.9(2) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C4 112.67(19) . . ?
C8 C9 H9A 109.1 . . ?
C4 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C4 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 109.67(18) . . ?
C11 C10 B1 114.11(17) . . ?
C15 C10 B1 113.72(16) . . ?
C11 C10 H10 106.2 . . ?
C15 C10 H10 106.2 . . ?
B1 C10 H10 106.2 . . ?
C10 C11 C12 111.9(2) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 112.3(2) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 111.0(2) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 111.2(2) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C10 113.0(2) . . ?
C14 C15 H15A 109.0 . . ?
C10 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C10 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C21 C16 C17 109.7(2) . . ?
C21 C16 B2 114.62(17) . . ?
C17 C16 B2 111.13(17) . . ?
C21 C16 H16 107.0 . . ?
C17 C16 H16 107.0 . . ?
B2 C16 H16 107.0 . . ?
C18 C17 C16 111.7(2) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 112.1(3) . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 111.8(3) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 C21 110.8(3) . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 C16 112.0(2) . . ?
C20 C21 H21A 109.2 . . ?
C16 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
C16 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C27 C22 C23 109.27(17) . . ?
C27 C22 B2 114.14(15) . . ?
C23 C22 B2 113.34(16) . . ?
C27 C22 H22 106.5 . . ?
C23 C22 H22 106.5 . . ?
B2 C22 H22 106.5 . . ?
C24 C23 C22 112.04(18) . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C25 C24 C23 111.1(2) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 112.1(2) . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 C27 110.6(2) . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C26 C27 C22 112.18(19) . . ?
C26 C27 H27A 109.2 . . ?
C22 C27 H27A 109.2 . . ?
C26 C27 H27B 109.2 . . ?
C22 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
C29 C28 C33 109.19(17) . . ?
C29 C28 B3 112.83(15) . . ?
C33 C28 B3 114.07(16) . . ?
C29 C28 H28 106.8 . . ?
C33 C28 H28 106.8 . . ?
B3 C28 H28 106.8 . . ?
C28 C29 C30 111.40(19) . . ?
C28 C29 H29A 109.3 . . ?
C30 C29 H29A 109.3 . . ?
C28 C29 H29B 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
C31 C30 C29 111.5(2) . . ?
C31 C30 H30A 109.3 . . ?
C29 C30 H30A 109.3 . . ?
C31 C30 H30B 109.3 . . ?
C29 C30 H30B 109.3 . . ?
H30A C30 H30B 108.0 . . ?
C32 C31 C30 111.4(2) . . ?
C32 C31 H31A 109.4 . . ?
C30 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
C30 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C31 C32 C33 111.8(2) . . ?
C31 C32 H32A 109.3 . . ?
C33 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C33 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C32 C33 C28 113.0(2) . . ?
C32 C33 H33A 109.0 . . ?
C28 C33 H33A 109.0 . . ?
C32 C33 H33B 109.0 . . ?
C28 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C35 C34 C39 108.48(18) . . ?
C35 C34 B3 115.05(18) . . ?
C39 C34 B3 115.56(15) . . ?
C35 C34 H34 105.6 . . ?
C39 C34 H34 105.6 . . ?
B3 C34 H34 105.6 . . ?
C34 C35 C36 112.6(2) . . ?
C34 C35 H35A 109.1 . . ?
C36 C35 H35A 109.1 . . ?
C34 C35 H35B 109.1 . . ?
C36 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C37 C36 C35 111.1(2) . . ?
C37 C36 H36A 109.4 . . ?
C35 C36 H36A 109.4 . . ?
C37 C36 H36B 109.4 . . ?
C35 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?
C36 C37 C38 111.2(2) . . ?
C36 C37 H37A 109.4 . . ?
C38 C37 H37A 109.4 . . ?
C36 C37 H37B 109.4 . . ?
C38 C37 H37B 109.4 . . ?
H37A C37 H37B 108.0 . . ?
C37 C38 C39 110.9(2) . . ?
C37 C38 H38A 109.5 . . ?
C39 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C39 C38 H38B 109.5 . . ?
H38A C38 H38B 108.1 . . ?
C38 C39 C34 112.57(18) . . ?
C38 C39 H39A 109.1 . . ?
C34 C39 H39A 109.1 . . ?
C38 C39 H39B 109.1 . . ?
C34 C39 H39B 109.1 . . ?
H39A C39 H39B 107.8 . . ?
C43 O7A C40A 113.9(4) . . ?
C43 O7B C40B 108.7(7) . . ?
O7A C40A C41A 100.4(5) . . ?
O7A C40A H40A 111.6 . . ?
C41A C40A H40A 117.5 . . ?
O7A C40A H40B 110.4 . . ?
C41A C40A H40B 107.1 . . ?
H40A C40A H40B 109.5 . . ?
O7B C40B C41B 98.6(8) . . ?
O7B C40B H40C 113.1 . . ?
C41B C40B H40C 112.0 . . ?
O7B C40B H40D 111.8 . . ?
C41B C40B H40D 111.1 . . ?
H40C C40B H40D 109.8 . . ?
C42 C41A C40A 109.9(5) . . ?
C42 C41A H41A 111.9 . . ?
C40A C41A H41A 114.4 . . ?
C42 C41A H41B 106.8 . . ?
C40A C41A H41B 104.6 . . ?
H41A C41A H41B 108.7 . . ?
C42 C41B C40B 87.9(7) . . ?
C42 C41B H41C 114.7 . . ?
C40B C41B H41C 115.0 . . ?
C42 C41B H41D 112.8 . . ?
C40B C41B H41D 113.7 . . ?
H41C C41B H41D 111.1 . . ?
C43 C42 C41B 108.7(6) . . ?
C43 C42 C41A 99.2(4) . . ?
C43 C42 H42A 109.9 . . ?
C41A C42 H42A 114.9 . . ?
C43 C42 H42B 114.6 . . ?
C41A C42 H42B 108.9 . . ?
H42A C42 H42B 109.1 . . ?
C43 C42 H42C 109.5 . . ?
C41B C42 H42C 109.3 . . ?
C43 C42 H42D 110.2 . . ?
C41B C42 H42D 110.5 . . ?
H42C C42 H42D 108.6 . . ?
O7A C43 C42 114.1(4) . . ?
C42 C43 O7B 93.0(5) . . ?
O7A C43 H43A 110.5 . . ?
C42 C43 H43A 111.3 . . ?
O7A C43 H43B 106.5 . . ?
C42 C43 H43B 106.0 . . ?
H43A C43 H43B 108.0 . . ?
C42 C43 H43C 112.4 . . ?
O7B C43 H43C 112.3 . . ?
C42 C43 H43D 114.1 . . ?
O7B C43 H43D 113.6 . . ?
H43C C43 H43D 110.5 . . ?
C47A O8A C44A 119.1(11) . . ?
C44B O8B C47B 90.4(9) . . ?
O8A C44A C45A 101.0(11) . . ?
O8A C44A H44A 120.2 . . ?
C45A C44A H44A 102.0 . . ?
O8A C44A H44B 115.8 . . ?
C45A C44A H44B 106.6 . . ?
H44A C44A H44B 109.0 . . ?
O8B C44B C45B 112.8(10) . . ?
O8B C44B H44C 104.9 . . ?
C45B C44B H44C 119.1 . . ?
O8B C44B H44D 108.2 . . ?
C45B C44B H44D 104.0 . . ?
H44C C44B H44D 107.3 . . ?
C44A C45A C46 93.7(9) . . ?
C44A C45A H45A 126.1 . . ?
C46 C45A H45A 116.3 . . ?
C44A C45A H45B 106.4 . . ?
C46 C45A H45B 99.9 . . ?
H45A C45A H45B 110.5 . . ?
C46 C45B C44B 98.4(7) . . ?
C46 C45B H45C 87.0 . . ?
C44B C45B H45C 89.8 . . ?
H45B C45B H45C 108.3 . . ?
C46 C45B H45D 129.8 . . ?
C44B C45B H45D 127.8 . . ?
H45C C45B H45D 108.8 . . ?
C47A C46 C45A 115.4(10) . . ?
C45B C46 C47B 99.7(6) . . ?
C47A C46 H46A 116.0 . . ?
C45A C46 H46A 97.8 . . ?
C47A C46 H46B 97.8 . . ?
C45A C46 H46B 122.2 . . ?
H46A C46 H46B 108.6 . . ?
C45B C46 H46C 132.9 . . ?
C47B C46 H46C 110.0 . . ?
C45B C46 H46D 88.9 . . ?
C47B C46 H46D 114.7 . . ?
H46C C46 H46D 109.4 . . ?
O8A C47A C46 93.2(9) . . ?
O8A C47A H47A 112.7 . . ?
C46 C47A H47A 121.1 . . ?
O8A C47A H47B 106.4 . . ?
C46 C47A H47B 112.3 . . ?
H47A C47A H47B 109.4 . . ?
O8B C47B C46 116.2(7) . . ?
O8B C47B H47C 103.4 . . ?
C46 C47B H47C 105.6 . . ?
O8B C47B H47D 112.3 . . ?
C46 C47B H47D 110.8 . . ?
H47C C47B H47D 107.6 . . ?

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2284251'
loop_
_audit_author_name
_audit_author_address
'Pierre Thuery'
;CEA Saclay
France
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 B N O2'
_chemical_formula_weight         245.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.7670(2)
_cell_length_b                   12.8036(5)
_cell_length_c                   18.9389(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2610.85(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    59510
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      25.68

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_special_details           'crystal-to-detector distance 30 mm'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'two φ and two ω scans with 2° steps (302 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            59510
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.696
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2468
_reflns_number_gt                2140
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by intrinsic phasing and subsequent difference Fourier
 synthesis. All non-hydrogen atoms were refined with anisotropic
 displacement parameters. The H atoms were introduced at calculated
 positions and were treated as riding atoms with an isotropic displacement
 parameter equal to 1.2 times that of the parent atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+0.6479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2468
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.21022(8) 0.21466(6) 0.58874(5) 0.0314(2) Uani 1 1 d . . . . .
O2 O 0.01755(8) 0.28478(7) 0.58795(5) 0.0380(2) Uani 1 1 d . . . . .
B1 B 0.28193(12) 0.31501(11) 0.60311(7) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.24775(9) 0.38712(8) 0.53482(5) 0.0274(2) Uani 1 1 d . . . . .
C1 C 0.08900(12) 0.21218(10) 0.58367(7) 0.0346(3) Uani 1 1 d . . . . .
H1 H 0.0529 0.1455 0.5757 0.042 Uiso 1 1 calc R U . . .
C2 C 0.25042(12) 0.36920(10) 0.67780(6) 0.0301(3) Uani 1 1 d . . . . .
H2 H 0.1618 0.3925 0.6774 0.036 Uiso 1 1 calc R U . . .
C3 C 0.26617(12) 0.28337(10) 0.73466(7) 0.0364(3) Uani 1 1 d . . . . .
H3A H 0.2492 0.3144 0.7816 0.044 Uiso 1 1 calc R U . . .
H3B H 0.2032 0.2284 0.7263 0.044 Uiso 1 1 calc R U . . .
C4 C 0.39515(13) 0.23231(11) 0.73630(7) 0.0388(3) Uani 1 1 d . . . . .
H4A H 0.3902 0.1676 0.7647 0.047 Uiso 1 1 calc R U . . .
H4B H 0.4534 0.2802 0.7605 0.047 Uiso 1 1 calc R U . . .
C5 C 0.44865(12) 0.20506(10) 0.66338(7) 0.0345(3) Uani 1 1 d . . . . .
H5A H 0.4122 0.1378 0.6480 0.041 Uiso 1 1 calc R U . . .
H5B H 0.5393 0.1943 0.6685 0.041 Uiso 1 1 calc R U . . .
C6 C 0.42713(11) 0.28613(10) 0.60425(6) 0.0304(3) Uani 1 1 d . . . . .
H6 H 0.4491 0.2531 0.5580 0.036 Uiso 1 1 calc R U . . .
C7 C 0.50498(12) 0.38602(11) 0.61284(7) 0.0390(3) Uani 1 1 d . . . . .
H7A H 0.5940 0.3666 0.6141 0.047 Uiso 1 1 calc R U . . .
H7B H 0.4919 0.4310 0.5710 0.047 Uiso 1 1 calc R U . . .
C8 C 0.47420(13) 0.44888(11) 0.67917(8) 0.0427(3) Uani 1 1 d . . . . .
H8A H 0.5147 0.5181 0.6757 0.051 Uiso 1 1 calc R U . . .
H8B H 0.5098 0.4126 0.7206 0.051 Uiso 1 1 calc R U . . .
C9 C 0.33448(13) 0.46507(10) 0.69165(7) 0.0377(3) Uani 1 1 d . . . . .
H9A H 0.3060 0.5230 0.6610 0.045 Uiso 1 1 calc R U . . .
H9B H 0.3224 0.4874 0.7412 0.045 Uiso 1 1 calc R U . . .
C10 C 0.28120(11) 0.35379(11) 0.46986(6) 0.0337(3) Uani 1 1 d . . . . .
H10 H 0.3288 0.2916 0.4656 0.040 Uiso 1 1 calc R U . . .
C11 C 0.24828(13) 0.40724(12) 0.40965(7) 0.0403(3) Uani 1 1 d . . . . .
H11 H 0.2719 0.3816 0.3645 0.048 Uiso 1 1 calc R U . . .
C12 C 0.18048(13) 0.49866(11) 0.41545(7) 0.0409(3) Uani 1 1 d . . . . .
H12 H 0.1576 0.5370 0.3745 0.049 Uiso 1 1 calc R U . . .
C13 C 0.14692(13) 0.53288(11) 0.48152(7) 0.0386(3) Uani 1 1 d . . . . .
H13 H 0.1009 0.5957 0.4870 0.046 Uiso 1 1 calc R U . . .
C14 C 0.18084(12) 0.47503(9) 0.53983(7) 0.0332(3) Uani 1 1 d . . . . .
H14 H 0.1558 0.4984 0.5853 0.040 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 C1 1.3091(16) . ?
O1 B1 1.5235(16) . ?
O2 C1 1.2093(16) . ?
B1 C6 1.6067(18) . ?
B1 C2 1.6116(17) . ?
B1 N1 1.6311(16) . ?
N1 C14 1.3397(16) . ?
N1 C10 1.3511(15) . ?
C1 H1 0.9500 . ?
C2 C9 1.5476(18) . ?
C2 C3 1.5479(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5352(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5365(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5443(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5377(17) . ?
C6 H6 1.0000 . ?
C7 C8 1.528(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.537(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3764(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3789(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C1 O1 B1 122.61(10) . . ?
O1 B1 C6 107.54(10) . . ?
O1 B1 C2 114.40(10) . . ?
C6 B1 C2 106.98(10) . . ?
O1 B1 N1 102.79(9) . . ?
C6 B1 N1 111.13(10) . . ?
C2 B1 N1 113.88(10) . . ?
C14 N1 C10 118.25(10) . . ?
C14 N1 B1 122.73(10) . . ?
C10 N1 B1 118.89(10) . . ?
O2 C1 O1 127.64(12) . . ?
O2 C1 H1 116.2 . . ?
O1 C1 H1 116.2 . . ?
C9 C2 C3 112.40(10) . . ?
C9 C2 B1 111.54(10) . . ?
C3 C2 B1 106.38(10) . . ?
C9 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
B1 C2 H2 108.8 . . ?
C4 C3 C2 114.55(10) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 114.68(10) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 116.29(10) . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C5 113.61(10) . . ?
C7 C6 B1 109.90(10) . . ?
C5 C6 B1 108.08(10) . . ?
C7 C6 H6 108.4 . . ?
C5 C6 H6 108.4 . . ?
B1 C6 H6 108.4 . . ?
C8 C7 C6 114.00(11) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 114.19(11) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C2 116.07(11) . . ?
C8 C9 H9A 108.3 . . ?
C2 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C2 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
N1 C10 C11 121.92(12) . . ?
N1 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 119.38(12) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 118.73(12) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 119.23(13) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N1 C14 C13 122.48(12) . . ?
N1 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2284252'
loop_
_audit_author_name
_audit_author_address
'Pierre Thuery'
;CEA Saclay
France
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H25 B N2 O2'
_chemical_formula_weight         288.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8725(5)
_cell_length_b                   7.3758(4)
_cell_length_c                   21.8820(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.551(3)
_cell_angle_gamma                90
_cell_volume                     1575.68(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    70088
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      25.68

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_special_details           'crystal-to-detector distance 33 mm'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'two φ and nine ω scans with 2° steps (625 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            70088
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.918
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2965
_reflns_number_gt                2550
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by intrinsic phasing and subsequent difference Fourier
 synthesis. All non-hydrogen atoms were refined with anisotropic
 displacement parameters. The H atoms were introduced at calculated
 positions and were treated as riding atoms with an isotropic displacement
 parameter equal to 1.2 times that of the parent atom (1.5 for CH₃, with
 optimized geometry). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+0.3088P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2965
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.91841(8) 0.04291(12) 0.56420(4) 0.0267(2) Uani 1 1 d . . . . .
O2 O 0.72479(8) -0.11148(12) 0.52927(4) 0.0284(2) Uani 1 1 d . . . . .
N1 N 0.75223(9) 0.22065(14) 0.61583(4) 0.0224(2) Uani 1 1 d . . . . .
N2 N 0.40321(10) 0.54531(14) 0.57353(5) 0.0255(2) Uani 1 1 d . . . . .
B1 B 0.88720(13) 0.09525(19) 0.62849(6) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.83833(12) -0.05541(18) 0.52457(5) 0.0276(3) Uani 1 1 d . . . . .
H1 H 0.8729 -0.0868 0.4877 0.033 Uiso 1 1 calc R U . . .
C2 C 1.01921(11) 0.20640(17) 0.66115(5) 0.0236(3) Uani 1 1 d . . . . .
H2 H 1.0336 0.3122 0.6343 0.028 Uiso 1 1 calc R U . . .
C3 C 1.14673(11) 0.08198(18) 0.66532(6) 0.0269(3) Uani 1 1 d . . . . .
H3A H 1.1689 0.0640 0.6231 0.032 Uiso 1 1 calc R U . . .
H3B H 1.2252 0.1457 0.6895 0.032 Uiso 1 1 calc R U . . .
C4 C 1.13287(12) -0.10531(18) 0.69461(6) 0.0299(3) Uani 1 1 d . . . . .
H4A H 1.2067 -0.1848 0.6840 0.036 Uiso 1 1 calc R U . . .
H4B H 1.1466 -0.0915 0.7401 0.036 Uiso 1 1 calc R U . . .
C5 C 0.99462(12) -0.19923(18) 0.67438(6) 0.0302(3) Uani 1 1 d . . . . .
H5A H 0.9857 -0.3011 0.7030 0.036 Uiso 1 1 calc R U . . .
H5B H 0.9945 -0.2510 0.6326 0.036 Uiso 1 1 calc R U . . .
C6 C 0.86849(12) -0.07436(17) 0.67284(5) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.7851 -0.1436 0.6546 0.029 Uiso 1 1 calc R U . . .
C7 C 0.84689(12) -0.00522(18) 0.73748(5) 0.0276(3) Uani 1 1 d . . . . .
H7A H 0.7548 0.0504 0.7339 0.033 Uiso 1 1 calc R U . . .
H7B H 0.8477 -0.1110 0.7654 0.033 Uiso 1 1 calc R U . . .
C8 C 0.95245(13) 0.13338(18) 0.76796(5) 0.0289(3) Uani 1 1 d . . . . .
H8A H 0.9149 0.1934 0.8023 0.035 Uiso 1 1 calc R U . . .
H8B H 1.0363 0.0676 0.7860 0.035 Uiso 1 1 calc R U . . .
C9 C 0.99180(12) 0.27955(18) 0.72400(5) 0.0265(3) Uani 1 1 d . . . . .
H9A H 1.0750 0.3427 0.7443 0.032 Uiso 1 1 calc R U . . .
H9B H 0.9170 0.3700 0.7168 0.032 Uiso 1 1 calc R U . . .
C10 C 0.76013(12) 0.39539(17) 0.59806(5) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.8482 0.4438 0.5953 0.029 Uiso 1 1 calc R U . . .
C11 C 0.64936(12) 0.50657(17) 0.58378(5) 0.0248(3) Uani 1 1 d . . . . .
H11 H 0.6617 0.6283 0.5716 0.030 Uiso 1 1 calc R U . . .
C12 C 0.51611(12) 0.44040(17) 0.58715(5) 0.0232(3) Uani 1 1 d . . . . .
C13 C 0.50850(12) 0.25773(17) 0.60562(5) 0.0245(3) Uani 1 1 d . . . . .
H13 H 0.4220 0.2051 0.6089 0.029 Uiso 1 1 calc R U . . .
C14 C 0.62513(11) 0.15606(17) 0.61888(5) 0.0240(3) Uani 1 1 d . . . . .
H14 H 0.6164 0.0334 0.6309 0.029 Uiso 1 1 calc R U . . .
C15 C 0.41075(12) 0.73817(18) 0.56030(6) 0.0293(3) Uani 1 1 d . . . . .
H15A H 0.4142 0.8072 0.5988 0.044 Uiso 1 1 calc R U . . .
H15B H 0.3297 0.7743 0.5314 0.044 Uiso 1 1 calc R U . . .
H15C H 0.4934 0.7628 0.5418 0.044 Uiso 1 1 calc R U . . .
C16 C 0.26917(12) 0.47510(19) 0.58180(6) 0.0317(3) Uani 1 1 d . . . . .
H16A H 0.2513 0.3622 0.5584 0.048 Uiso 1 1 calc R U . . .
H16B H 0.1986 0.5646 0.5669 0.048 Uiso 1 1 calc R U . . .
H16C H 0.2675 0.4513 0.6257 0.048 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 C1 1.3035(15) . ?
O1 B1 1.5336(15) . ?
O2 C1 1.2134(15) . ?
N1 C10 1.3519(16) . ?
N1 C14 1.3530(15) . ?
N1 B1 1.6119(16) . ?
N2 C12 1.3532(15) . ?
N2 C15 1.4558(17) . ?
N2 C16 1.4571(16) . ?
B1 C6 1.6107(18) . ?
B1 C2 1.6138(17) . ?
C1 H1 0.9500 . ?
C2 C9 1.5382(16) . ?
C2 C3 1.5496(16) . ?
C2 H2 1.0000 . ?
C3 C4 1.5375(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5359(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5452(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5478(17) . ?
C6 H6 1.0000 . ?
C7 C8 1.5393(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5329(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3654(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.4153(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.4119(18) . ?
C13 C14 1.3686(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C1 O1 B1 124.45(9) . . ?
C10 N1 C14 116.32(10) . . ?
C10 N1 B1 120.99(9) . . ?
C14 N1 B1 122.59(10) . . ?
C12 N2 C15 122.53(10) . . ?
C12 N2 C16 120.19(11) . . ?
C15 N2 C16 116.50(10) . . ?
O1 B1 C6 114.45(10) . . ?
O1 B1 N1 105.10(9) . . ?
C6 B1 N1 112.53(9) . . ?
O1 B1 C2 105.96(9) . . ?
C6 B1 C2 106.56(9) . . ?
N1 B1 C2 112.16(10) . . ?
O2 C1 O1 127.57(11) . . ?
O2 C1 H1 116.2 . . ?
O1 C1 H1 116.2 . . ?
C9 C2 C3 113.86(9) . . ?
C9 C2 B1 109.65(9) . . ?
C3 C2 B1 108.71(10) . . ?
C9 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
B1 C2 H2 108.2 . . ?
C4 C3 C2 115.77(10) . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
C2 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C5 C4 C3 114.55(10) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 114.59(11) . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 C7 113.36(10) . . ?
C5 C6 B1 108.17(10) . . ?
C7 C6 B1 109.78(10) . . ?
C5 C6 H6 108.5 . . ?
C7 C6 H6 108.5 . . ?
B1 C6 H6 108.5 . . ?
C8 C7 C6 116.00(10) . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C9 C8 C7 114.43(10) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C2 114.14(11) . . ?
C8 C9 H9A 108.7 . . ?
C2 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C2 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N1 C10 C11 124.05(11) . . ?
N1 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C10 C11 C12 120.00(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C12 C13 122.12(11) . . ?
N2 C12 C11 122.20(11) . . ?
C13 C12 C11 115.68(11) . . ?
C14 C13 C12 120.31(11) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N1 C14 C13 123.63(11) . . ?
N1 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 2284254'
loop_
_audit_author_name
_audit_author_address
'Pierre Thuery'
;CEA Saclay
France
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H33 B N2 O2'
_chemical_formula_weight         344.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.5923(8)
_cell_length_b                   10.8437(6)
_cell_length_c                   14.9151(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.370(5)
_cell_angle_gamma                90
_cell_volume                     2036.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    55323
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      25.68

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_special_details           'crystal-to-detector distance 33 mm'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'two φ and four ω scans with 2° steps (414 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            55323
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.825
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3861
_reflns_number_gt                2652
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by intrinsic phasing and subsequent difference Fourier
 synthesis. All non-hydrogen atoms were refined with anisotropic
 displacement parameters. The H atoms were introduced at calculated
 positions and were treated as riding atoms with an isotropic displacement
 parameter equal to 1.2 times that of the parent atom (1.5 for CH₃, with
 optimized geometry). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3861
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.28423(8) 0.11951(8) 0.48204(6) 0.0408(3) Uani 1 1 d . . . . .
O2 O 0.28146(8) 0.00615(9) 0.60555(6) 0.0469(3) Uani 1 1 d . . . . .
N1 N 0.35444(9) 0.24058(10) 0.36044(7) 0.0362(3) Uani 1 1 d . . . . .
N2 N 0.62024(9) 0.27778(10) 0.19525(8) 0.0394(3) Uani 1 1 d . . . . .
B1 B 0.25169(13) 0.23111(15) 0.42541(11) 0.0380(4) Uani 1 1 d . . . . .
C1 C 0.25068(11) 0.09394(13) 0.56192(10) 0.0408(4) Uani 1 1 d . . . . .
H1 H 0.1991 0.1468 0.5878 0.049 Uiso 1 1 calc R U . . .
C2 C 0.14818(11) 0.19682(13) 0.36547(9) 0.0398(4) Uani 1 1 d . . . . .
H2 H 0.1357 0.2673 0.3235 0.048 Uiso 1 1 calc R U . . .
C3 C 0.16115(12) 0.08062(14) 0.30772(10) 0.0477(4) Uani 1 1 d . . . . .
H3A H 0.2237 0.0910 0.2686 0.057 Uiso 1 1 calc R U . . .
H3B H 0.1748 0.0091 0.3474 0.057 Uiso 1 1 calc R U . . .
C4 C 0.06381(13) 0.05349(16) 0.24945(11) 0.0533(4) Uani 1 1 d . . . . .
H4A H 0.0540 0.1207 0.2052 0.064 Uiso 1 1 calc R U . . .
H4B H 0.0751 -0.0243 0.2161 0.064 Uiso 1 1 calc R U . . .
C5 C -0.03562(12) 0.04210(15) 0.30678(11) 0.0508(4) Uani 1 1 d . . . . .
H5A H -0.0294 -0.0315 0.3458 0.061 Uiso 1 1 calc R U . . .
H5B H -0.0984 0.0308 0.2673 0.061 Uiso 1 1 calc R U . . .
C6 C -0.05125(12) 0.15654(14) 0.36476(11) 0.0482(4) Uani 1 1 d . . . . .
H6A H -0.0660 0.2285 0.3258 0.058 Uiso 1 1 calc R U . . .
H6B H -0.1133 0.1442 0.4042 0.058 Uiso 1 1 calc R U . . .
C7 C 0.04706(11) 0.18242(14) 0.42206(10) 0.0435(4) Uani 1 1 d . . . . .
H7A H 0.0573 0.1139 0.4651 0.052 Uiso 1 1 calc R U . . .
H7B H 0.0356 0.2589 0.4569 0.052 Uiso 1 1 calc R U . . .
C8 C 0.24457(11) 0.35601(13) 0.48510(9) 0.0395(4) Uani 1 1 d . . . . .
H8 H 0.1951 0.3372 0.5354 0.047 Uiso 1 1 calc R U . . .
C9 C 0.19647(12) 0.46760(12) 0.43511(10) 0.0436(4) Uani 1 1 d . . . . .
H9A H 0.2417 0.4880 0.3831 0.052 Uiso 1 1 calc R U . . .
H9B H 0.1252 0.4452 0.4120 0.052 Uiso 1 1 calc R U . . .
C10 C 0.18700(13) 0.58081(13) 0.49517(10) 0.0482(4) Uani 1 1 d . . . . .
H10A H 0.1586 0.6508 0.4598 0.058 Uiso 1 1 calc R U . . .
H10B H 0.1366 0.5633 0.5442 0.058 Uiso 1 1 calc R U . . .
C11 C 0.29406(14) 0.61596(14) 0.53477(11) 0.0517(4) Uani 1 1 d . . . . .
H11A H 0.2855 0.6881 0.5748 0.062 Uiso 1 1 calc R U . . .
H11B H 0.3429 0.6396 0.4859 0.062 Uiso 1 1 calc R U . . .
C12 C 0.34176(14) 0.50936(13) 0.58754(10) 0.0498(4) Uani 1 1 d . . . . .
H12A H 0.2966 0.4912 0.6400 0.060 Uiso 1 1 calc R U . . .
H12B H 0.4132 0.5328 0.6098 0.060 Uiso 1 1 calc R U . . .
C13 C 0.35050(12) 0.39415(13) 0.52900(10) 0.0439(4) Uani 1 1 d . . . . .
H13A H 0.3770 0.3250 0.5662 0.053 Uiso 1 1 calc R U . . .
H13B H 0.4033 0.4095 0.4814 0.053 Uiso 1 1 calc R U . . .
C14 C 0.44839(11) 0.18589(12) 0.38009(9) 0.0377(3) Uani 1 1 d . . . . .
H14 H 0.4529 0.1383 0.4334 0.045 Uiso 1 1 calc R U . . .
C15 C 0.53685(11) 0.19465(12) 0.32836(9) 0.0381(3) Uani 1 1 d . . . . .
H15 H 0.5999 0.1525 0.3454 0.046 Uiso 1 1 calc R U . . .
C16 C 0.53482(11) 0.26640(12) 0.24939(9) 0.0365(3) Uani 1 1 d . . . . .
C17 C 0.43759(11) 0.32581(12) 0.23011(9) 0.0380(3) Uani 1 1 d . . . . .
H17 H 0.4316 0.3773 0.1788 0.046 Uiso 1 1 calc R U . . .
C18 C 0.35203(12) 0.30970(12) 0.28484(9) 0.0377(3) Uani 1 1 d . . . . .
H18 H 0.2873 0.3492 0.2689 0.045 Uiso 1 1 calc R U . . .
C19 C 0.72460(11) 0.23371(14) 0.22414(10) 0.0459(4) Uani 1 1 d . . . . .
H19A H 0.7539 0.2900 0.2694 0.069 Uiso 1 1 calc R U . . .
H19B H 0.7722 0.2306 0.1725 0.069 Uiso 1 1 calc R U . . .
H19C H 0.7177 0.1510 0.2499 0.069 Uiso 1 1 calc R U . . .
C20 C 0.61715(12) 0.36269(13) 0.11964(10) 0.0453(4) Uani 1 1 d . . . . .
H20A H 0.5561 0.3431 0.0812 0.068 Uiso 1 1 calc R U . . .
H20B H 0.6827 0.3547 0.0851 0.068 Uiso 1 1 calc R U . . .
H20C H 0.6106 0.4474 0.1418 0.068 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 C1 1.2967(16) . ?
O1 B1 1.5302(18) . ?
O2 C1 1.2151(16) . ?
N1 C14 1.3539(17) . ?
N1 C18 1.3541(17) . ?
N1 B1 1.6248(18) . ?
N2 C16 1.3548(17) . ?
N2 C20 1.4561(18) . ?
N2 C19 1.4607(18) . ?
B1 C2 1.619(2) . ?
B1 C8 1.624(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.5357(19) . ?
C2 C7 1.5401(19) . ?
C2 H2 1.0000 . ?
C3 C4 1.527(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.526(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.526(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.526(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.539(2) . ?
C8 C9 1.5432(19) . ?
C8 H8 1.0000 . ?
C9 C10 1.525(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.517(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.528(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.3625(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.4117(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.4114(19) . ?
C17 C18 1.3671(19) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C1 O1 B1 126.06(11) . . ?
C14 N1 C18 115.95(12) . . ?
C14 N1 B1 122.77(11) . . ?
C18 N1 B1 121.20(11) . . ?
C16 N2 C20 120.12(11) . . ?
C16 N2 C19 120.70(12) . . ?
C20 N2 C19 117.05(11) . . ?
O1 B1 C2 109.57(11) . . ?
O1 B1 C8 111.87(12) . . ?
C2 B1 C8 116.57(12) . . ?
O1 B1 N1 99.66(10) . . ?
C2 B1 N1 109.06(11) . . ?
C8 B1 N1 108.74(11) . . ?
O2 C1 O1 123.69(14) . . ?
O2 C1 H1 118.2 . . ?
O1 C1 H1 118.2 . . ?
C3 C2 C7 108.39(11) . . ?
C3 C2 B1 114.21(12) . . ?
C7 C2 B1 112.72(11) . . ?
C3 C2 H2 107.0 . . ?
C7 C2 H2 107.0 . . ?
B1 C2 H2 107.0 . . ?
C4 C3 C2 112.93(13) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 110.81(12) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 111.16(13) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 111.09(13) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C2 112.48(12) . . ?
C6 C7 H7A 109.1 . . ?
C2 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C2 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C13 C8 C9 109.35(12) . . ?
C13 C8 B1 114.00(12) . . ?
C9 C8 B1 114.33(11) . . ?
C13 C8 H8 106.2 . . ?
C9 C8 H8 106.2 . . ?
B1 C8 H8 106.2 . . ?
C10 C9 C8 112.29(12) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 111.00(13) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 110.96(13) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 110.82(12) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C8 113.41(13) . . ?
C12 C13 H13A 108.9 . . ?
C8 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C8 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N1 C14 C15 124.29(13) . . ?
N1 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C14 C15 C16 120.03(13) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
N2 C16 C17 121.86(13) . . ?
N2 C16 C15 122.50(13) . . ?
C17 C16 C15 115.63(13) . . ?
C18 C17 C16 120.39(13) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
N1 C18 C17 123.67(13) . . ?
N1 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.047

_shelxl_version_number           2014-3


####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 2284253'
loop_
_audit_author_name
_audit_author_address
'Pierre Thuery'
;CEA Saclay
France
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H28 B N O2'
_chemical_formula_weight         301.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.1407(4)
_cell_length_b                   28.0242(11)
_cell_length_c                   12.2214(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.627(3)
_cell_angle_gamma                90
_cell_volume                     3461.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    105117
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      25.68

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_special_details           'crystal-to-detector distance 33 mm'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       
'two φ and four ω scans with 2° steps (440 frames)'
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            105117
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         25.682
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6562
_reflns_number_gt                5121
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'

_refine_special_details          
;
 Structure solved by intrinsic phasing and subsequent difference Fourier
 synthesis. All non-hydrogen atoms were refined with anisotropic
 displacement parameters. The H atoms were introduced at calculated
 positions and were treated as riding atoms with an isotropic displacement
 parameter equal to 1.2 times that of the parent atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+0.3295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6562
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 B 0.87612(13) 0.38411(5) 0.35060(12) 0.0281(3) Uani 1 1 d . . . . .
B2 B 0.34643(13) 0.37762(5) 0.80250(12) 0.0287(3) Uani 1 1 d . . . . .
O1 O 0.79600(8) 0.42038(3) 0.41052(7) 0.0288(2) Uani 1 1 d . . . . .
O2 O 0.61141(8) 0.46217(3) 0.42136(7) 0.0374(2) Uani 1 1 d . . . . .
O3 O 0.25101(8) 0.40673(3) 0.72733(7) 0.0298(2) Uani 1 1 d . . . . .
O4 O 0.05316(9) 0.43907(4) 0.68718(8) 0.0476(3) Uani 1 1 d . . . . .
N1 N 1.02637(10) 0.40069(4) 0.39184(8) 0.0279(2) Uani 1 1 d . . . . .
N2 N 0.48749(9) 0.39666(4) 0.76393(8) 0.0273(2) Uani 1 1 d . . . . .
C1 C 0.67558(12) 0.43259(5) 0.37692(10) 0.0320(3) Uani 1 1 d . . . . .
H1 H 0.6355 0.4173 0.3133 0.038 Uiso 1 1 calc R U . . .
C2 C 0.85903(12) 0.39166(4) 0.21796(10) 0.0296(3) Uani 1 1 d . . . . .
H2 H 0.7638 0.3853 0.1950 0.036 Uiso 1 1 calc R U . . .
C3 C 0.88661(14) 0.44286(5) 0.18069(10) 0.0355(3) Uani 1 1 d . . . . .
H3A H 0.8301 0.4652 0.2187 0.043 Uiso 1 1 calc R U . . .
H3B H 0.9800 0.4509 0.2027 0.043 Uiso 1 1 calc R U . . .
C4 C 0.86068(14) 0.44966(5) 0.05718(11) 0.0384(3) Uani 1 1 d . . . . .
H4A H 0.7652 0.4452 0.0359 0.046 Uiso 1 1 calc R U . . .
H4B H 0.8849 0.4826 0.0374 0.046 Uiso 1 1 calc R U . . .
C5 C 0.93994(13) 0.41439(5) -0.00543(11) 0.0382(3) Uani 1 1 d . . . . .
H5A H 1.0355 0.4213 0.0091 0.046 Uiso 1 1 calc R U . . .
H5B H 0.9165 0.4181 -0.0852 0.046 Uiso 1 1 calc R U . . .
C6 C 0.91285(15) 0.36332(5) 0.02827(11) 0.0418(3) Uani 1 1 d . . . . .
H6A H 0.9702 0.3413 -0.0099 0.050 Uiso 1 1 calc R U . . .
H6B H 0.8196 0.3551 0.0058 0.050 Uiso 1 1 calc R U . . .
C7 C 0.93894(14) 0.35682(5) 0.15254(11) 0.0367(3) Uani 1 1 d . . . . .
H7A H 1.0344 0.3616 0.1734 0.044 Uiso 1 1 calc R U . . .
H7B H 0.9162 0.3237 0.1722 0.044 Uiso 1 1 calc R U . . .
C8 C 0.84838(12) 0.33074(4) 0.39596(10) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.9142 0.3089 0.3654 0.036 Uiso 1 1 calc R U . . .
C9 C 0.70989(13) 0.31228(5) 0.35610(13) 0.0442(4) Uani 1 1 d . . . . .
H9A H 0.6424 0.3344 0.3813 0.053 Uiso 1 1 calc R U . . .
H9B H 0.7010 0.3121 0.2748 0.053 Uiso 1 1 calc R U . . .
C10 C 0.68340(16) 0.26202(6) 0.39822(15) 0.0558(4) Uani 1 1 d . . . . .
H10A H 0.5919 0.2525 0.3732 0.067 Uiso 1 1 calc R U . . .
H10B H 0.7447 0.2392 0.3668 0.067 Uiso 1 1 calc R U . . .
C11 C 0.70135(15) 0.25960(6) 0.52251(15) 0.0551(4) Uani 1 1 d . . . . .
H11A H 0.6883 0.2264 0.5468 0.066 Uiso 1 1 calc R U . . .
H11B H 0.6342 0.2799 0.5542 0.066 Uiso 1 1 calc R U . . .
C12 C 0.83884(15) 0.27643(5) 0.56346(13) 0.0478(4) Uani 1 1 d . . . . .
H12A H 0.9054 0.2539 0.5385 0.057 Uiso 1 1 calc R U . . .
H12B H 0.8469 0.2766 0.6447 0.057 Uiso 1 1 calc R U . . .
C13 C 0.86674(14) 0.32655(5) 0.52113(11) 0.0399(3) Uani 1 1 d . . . . .
H13A H 0.8069 0.3495 0.5538 0.048 Uiso 1 1 calc R U . . .
H13B H 0.9587 0.3355 0.5461 0.048 Uiso 1 1 calc R U . . .
C14 C 1.12805(12) 0.37013(5) 0.38543(11) 0.0337(3) Uani 1 1 d . . . . .
H14 H 1.1096 0.3382 0.3632 0.040 Uiso 1 1 calc R U . . .
C15 C 1.25741(13) 0.38355(5) 0.40985(11) 0.0381(3) Uani 1 1 d . . . . .
H15 H 1.3270 0.3613 0.4032 0.046 Uiso 1 1 calc R U . . .
C16 C 1.28518(13) 0.42960(5) 0.44418(11) 0.0387(3) Uani 1 1 d . . . . .
H16 H 1.3738 0.4395 0.4626 0.046 Uiso 1 1 calc R U . . .
C17 C 1.18186(13) 0.46088(5) 0.45118(11) 0.0391(3) Uani 1 1 d . . . . .
H17 H 1.1983 0.4928 0.4748 0.047 Uiso 1 1 calc R U . . .
C18 C 1.05431(13) 0.44567(5) 0.42373(10) 0.0341(3) Uani 1 1 d . . . . .
H18 H 0.9837 0.4677 0.4275 0.041 Uiso 1 1 calc R U . . .
C19 C 0.13010(12) 0.41692(5) 0.74773(11) 0.0345(3) Uani 1 1 d . . . . .
H19 H 0.1005 0.4061 0.8152 0.041 Uiso 1 1 calc R U . . .
C20 C 0.34077(12) 0.39155(4) 0.93167(10) 0.0306(3) Uani 1 1 d . . . . .
H20 H 0.2507 0.3822 0.9519 0.037 Uiso 1 1 calc R U . . .
C21 C 0.44027(13) 0.36464(5) 1.01113(11) 0.0370(3) Uani 1 1 d . . . . .
H21A H 0.4276 0.3299 1.0005 0.044 Uiso 1 1 calc R U . . .
H21B H 0.5313 0.3726 0.9935 0.044 Uiso 1 1 calc R U . . .
C22 C 0.42482(15) 0.37702(5) 1.13094(11) 0.0425(3) Uani 1 1 d . . . . .
H22A H 0.3372 0.3660 1.1510 0.051 Uiso 1 1 calc R U . . .
H22B H 0.4934 0.3601 1.1783 0.051 Uiso 1 1 calc R U . . .
C23 C 0.43746(13) 0.43037(5) 1.15127(11) 0.0398(3) Uani 1 1 d . . . . .
H23A H 0.5284 0.4408 1.1391 0.048 Uiso 1 1 calc R U . . .
H23B H 0.4215 0.4374 1.2285 0.048 Uiso 1 1 calc R U . . .
C24 C 0.33872(14) 0.45792(5) 1.07497(11) 0.0390(3) Uani 1 1 d . . . . .
H24A H 0.3529 0.4926 1.0860 0.047 Uiso 1 1 calc R U . . .
H24B H 0.2476 0.4503 1.0930 0.047 Uiso 1 1 calc R U . . .
C25 C 0.35418(13) 0.44529(5) 0.95540(10) 0.0353(3) Uani 1 1 d . . . . .
H25A H 0.4421 0.4562 0.9358 0.042 Uiso 1 1 calc R U . . .
H25B H 0.2863 0.4626 0.9082 0.042 Uiso 1 1 calc R U . . .
C26 C 0.33094(12) 0.32160(4) 0.77022(10) 0.0319(3) Uani 1 1 d . . . . .
H26 H 0.4007 0.3036 0.8157 0.038 Uiso 1 1 calc R U . . .
C27 C 0.35088(14) 0.31170(5) 0.64920(11) 0.0390(3) Uani 1 1 d . . . . .
H27A H 0.2849 0.3302 0.6026 0.047 Uiso 1 1 calc R U . . .
H27B H 0.4399 0.3230 0.6334 0.047 Uiso 1 1 calc R U . . .
C28 C 0.33772(15) 0.25907(5) 0.61842(14) 0.0497(4) Uani 1 1 d . . . . .
H28A H 0.3479 0.2552 0.5390 0.060 Uiso 1 1 calc R U . . .
H28B H 0.4087 0.2406 0.6596 0.060 Uiso 1 1 calc R U . . .
C29 C 0.20395(15) 0.24008(6) 0.64472(15) 0.0565(4) Uani 1 1 d . . . . .
H29A H 0.1993 0.2054 0.6290 0.068 Uiso 1 1 calc R U . . .
H29B H 0.1335 0.2561 0.5973 0.068 Uiso 1 1 calc R U . . .
C30 C 0.18101(15) 0.24865(5) 0.76436(16) 0.0548(4) Uani 1 1 d . . . . .
H30A H 0.2451 0.2295 0.8114 0.066 Uiso 1 1 calc R U . . .
H30B H 0.0909 0.2378 0.7780 0.066 Uiso 1 1 calc R U . . .
C31 C 0.19622(13) 0.30133(5) 0.79578(13) 0.0428(3) Uani 1 1 d . . . . .
H31A H 0.1859 0.3049 0.8752 0.051 Uiso 1 1 calc R U . . .
H31B H 0.1251 0.3199 0.7552 0.051 Uiso 1 1 calc R U . . .
C32 C 0.59798(12) 0.37037(5) 0.78499(10) 0.0319(3) Uani 1 1 d . . . . .
H32 H 0.5915 0.3405 0.8208 0.038 Uiso 1 1 calc R U . . .
C33 C 0.71964(12) 0.38530(5) 0.75648(11) 0.0362(3) Uani 1 1 d . . . . .
H33 H 0.7958 0.3660 0.7725 0.043 Uiso 1 1 calc R U . . .
C34 C 0.73001(13) 0.42872(5) 0.70422(11) 0.0389(3) Uani 1 1 d . . . . .
H34 H 0.8130 0.4397 0.6835 0.047 Uiso 1 1 calc R U . . .
C35 C 0.61740(13) 0.45560(5) 0.68283(11) 0.0365(3) Uani 1 1 d . . . . .
H35 H 0.6220 0.4856 0.6470 0.044 Uiso 1 1 calc R U . . .
C36 C 0.49803(12) 0.43897(4) 0.71340(10) 0.0310(3) Uani 1 1 d . . . . .
H36 H 0.4210 0.4579 0.6984 0.037 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
B1 O1 1.5249(16) . ?
B1 C8 1.6275(19) . ?
B1 C2 1.6301(18) . ?
B1 N1 1.6333(17) . ?
B2 O3 1.5174(16) . ?
B2 C26 1.6232(19) . ?
B2 N2 1.6315(16) . ?
B2 C20 1.6317(18) . ?
O1 C1 1.3023(14) . ?
O2 C1 1.2093(15) . ?
O3 C19 1.3024(15) . ?
O4 C19 1.2036(16) . ?
N1 C18 1.3429(16) . ?
N1 C14 1.3477(16) . ?
N2 C36 1.3451(16) . ?
N2 C32 1.3482(16) . ?
C1 H1 0.9500 . ?
C2 C7 1.5341(17) . ?
C2 C3 1.5378(18) . ?
C2 H2 1.0000 . ?
C3 C4 1.5232(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5191(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.520(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5313(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.5307(18) . ?
C8 C9 1.5385(17) . ?
C8 H8 1.0000 . ?
C9 C10 1.531(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.517(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.518(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5311(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.3742(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3774(18) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.5375(18) . ?
C20 C21 1.5400(18) . ?
C20 H20 1.0000 . ?
C21 C22 1.5250(19) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.519(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5224(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5239(18) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.5342(18) . ?
C26 C31 1.5348(17) . ?
C26 H26 1.0000 . ?
C27 C28 1.5253(19) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.516(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.518(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.530(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.3740(18) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.3755(19) . ?
C34 H34 0.9500 . ?
C35 C36 1.3766(17) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

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
O1 B1 C8 109.60(10) . . ?
O1 B1 C2 111.91(10) . . ?
C8 B1 C2 116.78(10) . . ?
O1 B1 N1 100.49(9) . . ?
C8 B1 N1 109.81(10) . . ?
C2 B1 N1 106.96(10) . . ?
O3 B2 C26 109.17(10) . . ?
O3 B2 N2 100.40(9) . . ?
C26 B2 N2 108.42(10) . . ?
O3 B2 C20 112.74(10) . . ?
C26 B2 C20 117.15(11) . . ?
N2 B2 C20 107.54(10) . . ?
C1 O1 B1 123.10(10) . . ?
C19 O3 B2 124.48(10) . . ?
C18 N1 C14 117.97(11) . . ?
C18 N1 B1 121.76(10) . . ?
C14 N1 B1 120.02(10) . . ?
C36 N2 C32 118.27(10) . . ?
C36 N2 B2 121.66(10) . . ?
C32 N2 B2 120.04(10) . . ?
O2 C1 O1 124.29(12) . . ?
O2 C1 H1 117.9 . . ?
O1 C1 H1 117.9 . . ?
C7 C2 C3 108.84(10) . . ?
C7 C2 B1 114.67(10) . . ?
C3 C2 B1 114.10(10) . . ?
C7 C2 H2 106.2 . . ?
C3 C2 H2 106.2 . . ?
B1 C2 H2 106.2 . . ?
C4 C3 C2 112.92(11) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.20(11) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 111.20(11) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 111.10(11) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C2 112.64(11) . . ?
C6 C7 H7A 109.1 . . ?
C2 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C2 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C13 C8 C9 108.96(11) . . ?
C13 C8 B1 113.61(10) . . ?
C9 C8 B1 112.31(10) . . ?
C13 C8 H8 107.2 . . ?
C9 C8 H8 107.2 . . ?
B1 C8 H8 107.2 . . ?
C10 C9 C8 112.54(12) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C9 111.59(13) . . ?
C11 C10 H10A 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 110.43(12) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 111.31(12) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C8 C13 C12 113.40(12) . . ?
C8 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C8 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N1 C14 C15 122.33(13) . . ?
N1 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C14 C15 C16 119.35(13) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 118.56(12) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 119.54(13) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
N1 C18 C17 122.22(12) . . ?
N1 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
O4 C19 O3 124.68(12) . . ?
O4 C19 H19 117.7 . . ?
O3 C19 H19 117.7 . . ?
C25 C20 C21 108.49(11) . . ?
C25 C20 B2 114.04(10) . . ?
C21 C20 B2 114.86(10) . . ?
C25 C20 H20 106.3 . . ?
C21 C20 H20 106.3 . . ?
B2 C20 H20 106.3 . . ?
C22 C21 C20 112.41(11) . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C21 111.53(11) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 110.87(11) . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C23 C24 C25 110.86(11) . . ?
C23 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 C20 113.20(11) . . ?
C24 C25 H25A 108.9 . . ?
C20 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C20 C25 H25B 108.9 . . ?
H25A C25 H25B 107.8 . . ?
C27 C26 C31 108.54(11) . . ?
C27 C26 B2 113.05(10) . . ?
C31 C26 B2 112.26(10) . . ?
C27 C26 H26 107.6 . . ?
C31 C26 H26 107.6 . . ?
B2 C26 H26 107.6 . . ?
C28 C27 C26 113.38(12) . . ?
C28 C27 H27A 108.9 . . ?
C26 C27 H27A 108.9 . . ?
C28 C27 H27B 108.9 . . ?
C26 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C29 C28 C27 110.44(12) . . ?
C29 C28 H28A 109.6 . . ?
C27 C28 H28A 109.6 . . ?
C29 C28 H28B 109.6 . . ?
C27 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C28 C29 C30 110.98(13) . . ?
C28 C29 H29A 109.4 . . ?
C30 C29 H29A 109.4 . . ?
C28 C29 H29B 109.4 . . ?
C30 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C29 C30 C31 111.96(13) . . ?
C29 C30 H30A 109.2 . . ?
C31 C30 H30A 109.2 . . ?
C29 C30 H30B 109.2 . . ?
C31 C30 H30B 109.2 . . ?
H30A C30 H30B 107.9 . . ?
C30 C31 C26 112.30(12) . . ?
C30 C31 H31A 109.1 . . ?
C26 C31 H31A 109.1 . . ?
C30 C31 H31B 109.1 . . ?
C26 C31 H31B 109.1 . . ?
H31A C31 H31B 107.9 . . ?
N2 C32 C33 122.31(12) . . ?
N2 C32 H32 118.8 . . ?
C33 C32 H32 118.8 . . ?
C32 C33 C34 119.25(12) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C35 C34 C33 118.50(12) . . ?
C35 C34 H34 120.8 . . ?
C33 C34 H34 120.8 . . ?
C34 C35 C36 119.84(13) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
N2 C36 C35 121.82(12) . . ?
N2 C36 H36 119.1 . . ?
C35 C36 H36 119.1 . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-3


