# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_sy11
_database_code_depnum_ccdc_archive 'CCDC 1568988'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2018-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H42 B N O'
_chemical_formula_weight         551.54

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   38.4003(15)
_cell_length_b                   9.7146(4)
_cell_length_c                   18.3058(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.338(2)
_cell_angle_gamma                90
_cell_volume                     6222.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_F_000             2368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83774
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.1461
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.375
_diffrn_reflns_theta_max         27.915
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7432
_reflns_number_gt                5010
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+6.4242P] 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         7432
_refine_ls_number_parameters     387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.62778(3) 0.51825(13) 0.55051(7) 0.0258(3) Uani 1 1 d . . . . .
B1 B 0.64123(5) 0.3673(2) 0.59369(12) 0.0227(4) Uani 1 1 d . . . . .
N1 N 0.39016(5) 0.39337(18) 0.65482(11) 0.0363(4) Uani 1 1 d . . . . .
C1 C 0.59451(5) 0.54571(18) 0.54333(10) 0.0243(4) Uani 1 1 d . . . . .
H1A H 0.5811 0.6250 0.5154 0.029 Uiso 1 1 calc R U . . .
C2 C 0.57811(5) 0.45083(18) 0.57953(10) 0.0222(4) Uani 1 1 d . . . . .
C3 C 0.60328(5) 0.33897(18) 0.60936(10) 0.0215(4) Uani 1 1 d . . . . .
C4 C 0.59202(5) 0.23920(18) 0.65005(11) 0.0246(4) Uani 1 1 d . . . . .
H4A H 0.6083 0.1629 0.6735 0.030 Uiso 1 1 calc R U . . .
C5 C 0.55749(5) 0.24973(19) 0.65672(11) 0.0249(4) Uani 1 1 d . . . . .
H5A H 0.5505 0.1787 0.6838 0.030 Uiso 1 1 calc R U . . .
C6 C 0.53223(5) 0.36133(18) 0.62512(10) 0.0228(4) Uani 1 1 d . . . . .
C7 C 0.54317(5) 0.46402(18) 0.58623(11) 0.0236(4) Uani 1 1 d . . . . .
H7A H 0.5273 0.5419 0.5645 0.028 Uiso 1 1 calc R U . . .
C8 C 0.49553(5) 0.36849(18) 0.63406(10) 0.0230(4) Uani 1 1 d . . . . .
C9 C 0.47471(5) 0.25092(19) 0.63351(11) 0.0253(4) Uani 1 1 d . . . . .
H9A H 0.4847 0.1634 0.6289 0.030 Uiso 1 1 calc R U . . .
C10 C 0.43980(5) 0.25762(19) 0.63950(11) 0.0268(4) Uani 1 1 d . . . . .
H10A H 0.4261 0.1753 0.6373 0.032 Uiso 1 1 calc R U . . .
C11 C 0.42455(5) 0.38482(19) 0.64874(11) 0.0262(4) Uani 1 1 d . . . . .
C12 C 0.44601(5) 0.5029(2) 0.65086(12) 0.0288(4) Uani 1 1 d . . . . .
H12A H 0.4369 0.5906 0.6579 0.035 Uiso 1 1 calc R U . . .
C13 C 0.48020(5) 0.49402(19) 0.64297(11) 0.0280(4) Uani 1 1 d . . . . .
H13A H 0.4937 0.5763 0.6436 0.034 Uiso 1 1 calc R U . . .
C14 C 0.37911(6) 0.5209(2) 0.68031(14) 0.0407(5) Uani 1 1 d . . . . .
H14A H 0.3992 0.5496 0.7317 0.061 Uiso 1 1 calc R U . . .
H14B H 0.3552 0.5071 0.6864 0.061 Uiso 1 1 calc R U . . .
H14C H 0.3755 0.5923 0.6400 0.061 Uiso 1 1 calc R U . . .
C15 C 0.36510(6) 0.2765(3) 0.63812(15) 0.0453(6) Uani 1 1 d . . . . .
H15A H 0.3592 0.2430 0.5838 0.068 Uiso 1 1 calc R U . . .
H15B H 0.3414 0.3035 0.6423 0.068 Uiso 1 1 calc R U . . .
H15C H 0.3776 0.2032 0.6769 0.068 Uiso 1 1 calc R U . . .
C16 C 0.64985(5) 0.28713(19) 0.52433(10) 0.0232(4) Uani 1 1 d . . . . .
C17 C 0.68259(5) 0.3246(2) 0.51147(11) 0.0287(4) Uani 1 1 d . . . . .
C18 C 0.70662(6) 0.4485(2) 0.55157(15) 0.0449(6) Uani 1 1 d . . . . .
H18A H 0.7242 0.4687 0.5265 0.067 Uiso 1 1 calc R U . . .
H18B H 0.7213 0.4291 0.6087 0.067 Uiso 1 1 calc R U . . .
H18C H 0.6899 0.5280 0.5455 0.067 Uiso 1 1 calc R U . . .
C19 C 0.69330(5) 0.2494(2) 0.45927(11) 0.0310(4) Uani 1 1 d . . . . .
H19A H 0.7156 0.2763 0.4527 0.037 Uiso 1 1 calc R U . . .
C20 C 0.67280(5) 0.1376(2) 0.41679(11) 0.0297(4) Uani 1 1 d . . . . .
C21 C 0.68583(6) 0.0525(2) 0.36348(13) 0.0414(5) Uani 1 1 d . . . . .
H21A H 0.7028 0.1079 0.3473 0.062 Uiso 1 1 calc R U . . .
H21B H 0.6635 0.0235 0.3157 0.062 Uiso 1 1 calc R U . . .
H21C H 0.6996 -0.0289 0.3929 0.062 Uiso 1 1 calc R U . . .
C22 C 0.63938(5) 0.1061(2) 0.42496(11) 0.0287(4) Uani 1 1 d . . . . .
H22A H 0.6240 0.0322 0.3945 0.034 Uiso 1 1 calc R U . . .
C23 C 0.62753(5) 0.17896(19) 0.47622(11) 0.0253(4) Uani 1 1 d . . . . .
C24 C 0.58966(5) 0.1353(2) 0.47657(13) 0.0352(5) Uani 1 1 d . . . . .
H24A H 0.5773 0.0678 0.4338 0.053 Uiso 1 1 calc R U . . .
H24B H 0.5731 0.2159 0.4676 0.053 Uiso 1 1 calc R U . . .
H24C H 0.5941 0.0938 0.5285 0.053 Uiso 1 1 calc R U . . .
C25 C 0.67752(5) 0.37670(18) 0.68130(10) 0.0225(4) Uani 1 1 d . . . . .
C26 C 0.69093(5) 0.49692(19) 0.72809(11) 0.0264(4) Uani 1 1 d . . . . .
C27 C 0.67472(6) 0.6384(2) 0.69986(13) 0.0378(5) Uani 1 1 d . . . . .
H27A H 0.6894 0.7070 0.7400 0.057 Uiso 1 1 calc R U . . .
H27B H 0.6479 0.6412 0.6924 0.057 Uiso 1 1 calc R U . . .
H27C H 0.6763 0.6590 0.6489 0.057 Uiso 1 1 calc R U . . .
C28 C 0.72059(5) 0.4900(2) 0.80472(12) 0.0303(4) Uani 1 1 d . . . . .
H28A H 0.7290 0.5725 0.8347 0.036 Uiso 1 1 calc R U . . .
C29 C 0.73812(5) 0.3675(2) 0.83857(11) 0.0311(4) Uani 1 1 d . . . . .
C30 C 0.77007(6) 0.3624(2) 0.92218(13) 0.0457(6) Uani 1 1 d . . . . .
H30A H 0.7719 0.4514 0.9487 0.068 Uiso 1 1 calc R U . . .
H30B H 0.7943 0.3423 0.9185 0.068 Uiso 1 1 calc R U . . .
H30C H 0.7646 0.2901 0.9534 0.068 Uiso 1 1 calc R U . . .
C31 C 0.72530(5) 0.2495(2) 0.79315(11) 0.0295(4) Uani 1 1 d . . . . .
H31A H 0.7371 0.1640 0.8148 0.035 Uiso 1 1 calc R U . . .
C32 C 0.69560(5) 0.25146(19) 0.71639(11) 0.0249(4) Uani 1 1 d . . . . .
C33 C 0.68499(5) 0.11416(19) 0.67372(12) 0.0312(4) Uani 1 1 d . . . . .
H33A H 0.6960 0.0396 0.7125 0.047 Uiso 1 1 calc R U . . .
H33B H 0.6950 0.1092 0.6324 0.047 Uiso 1 1 calc R U . . .
H33C H 0.6571 0.1048 0.6486 0.047 Uiso 1 1 calc R U . . .
C34 C 0.58368(6) 0.8584(2) 0.63380(14) 0.0384(5) Uani 1 1 d . . . . .
H34A H 0.6062 0.8577 0.6245 0.046 Uiso 1 1 calc R U . . .
C35 C 0.58616(7) 0.8480(2) 0.71051(14) 0.0451(6) Uani 1 1 d . . . . .
H35A H 0.6104 0.8390 0.7543 0.054 Uiso 1 1 calc R U . . .
C36 C 0.55345(7) 0.8506(3) 0.72391(14) 0.0504(6) Uani 1 1 d . . . . .
H36A H 0.5552 0.8446 0.7771 0.061 Uiso 1 1 calc R U . . .
C37 C 0.51833(7) 0.8619(2) 0.66062(16) 0.0490(6) Uani 1 1 d . . . . .
H37A H 0.4958 0.8638 0.6702 0.059 Uiso 1 1 calc R U . . .
C38 C 0.51563(6) 0.8704(2) 0.58354(15) 0.0449(6) Uani 1 1 d . . . . .
H38A H 0.4913 0.8766 0.5397 0.054 Uiso 1 1 calc R U . . .
C39 C 0.54835(7) 0.8698(2) 0.57011(13) 0.0412(5) Uani 1 1 d . . . . .
H39A H 0.5466 0.8773 0.5170 0.049 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 1.258(2) . ?
O1 B1 1.645(2) . ?
B1 C3 1.621(2) . ?
B1 C16 1.636(3) . ?
B1 C25 1.637(3) . ?
N1 C11 1.373(2) . ?
N1 C15 1.438(3) . ?
N1 C14 1.448(3) . ?
C1 C2 1.425(2) . ?
C1 H1A 0.9500 . ?
C2 C7 1.403(2) . ?
C2 C3 1.406(2) . ?
C3 C4 1.395(2) . ?
C4 C5 1.385(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.410(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.387(2) . ?
C6 C8 1.486(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.392(2) . ?
C8 C13 1.393(3) . ?
C9 C10 1.391(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.407(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.404(3) . ?
C12 C13 1.381(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C23 1.412(3) . ?
C16 C17 1.419(2) . ?
C17 C19 1.393(3) . ?
C17 C18 1.510(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.379(3) . ?
C19 H19A 0.9500 . ?
C20 C22 1.386(3) . ?
C20 C21 1.512(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.393(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.517(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.414(3) . ?
C25 C32 1.417(2) . ?
C26 C28 1.397(3) . ?
C26 C27 1.510(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.381(3) . ?
C28 H28A 0.9500 . ?
C29 C31 1.383(3) . ?
C29 C30 1.517(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.398(3) . ?
C31 H31A 0.9500 . ?
C32 C33 1.514(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.372(3) . ?
C34 C39 1.381(3) . ?
C34 H34A 0.9500 . ?
C35 C36 1.376(3) . ?
C35 H35A 0.9500 . ?
C36 C37 1.373(3) . ?
C36 H36A 0.9500 . ?
C37 C38 1.374(3) . ?
C37 H37A 0.9500 . ?
C38 C39 1.376(3) . ?
C38 H38A 0.9500 . ?
C39 H39A 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 110.09(13) . . ?
C3 B1 C16 122.74(15) . . ?
C3 B1 C25 107.49(14) . . ?
C16 B1 C25 115.09(14) . . ?
C3 B1 O1 96.29(12) . . ?
C16 B1 O1 100.10(13) . . ?
C25 B1 O1 113.16(14) . . ?
C11 N1 C15 121.13(17) . . ?
C11 N1 C14 119.82(16) . . ?
C15 N1 C14 119.03(16) . . ?
O1 C1 C2 116.04(16) . . ?
O1 C1 H1A 122.0 . . ?
C2 C1 H1A 122.0 . . ?
C7 C2 C3 124.45(16) . . ?
C7 C2 C1 127.15(16) . . ?
C3 C2 C1 108.40(15) . . ?
C4 C3 C2 115.44(15) . . ?
C4 C3 B1 135.37(16) . . ?
C2 C3 B1 108.91(15) . . ?
C5 C4 C3 120.96(16) . . ?
C5 C4 H4A 119.5 . . ?
C3 C4 H4A 119.5 . . ?
C4 C5 C6 122.85(16) . . ?
C4 C5 H5A 118.6 . . ?
C6 C5 H5A 118.6 . . ?
C7 C6 C5 117.44(15) . . ?
C7 C6 C8 121.63(16) . . ?
C5 C6 C8 120.93(16) . . ?
C6 C7 C2 118.82(16) . . ?
C6 C7 H7A 120.6 . . ?
C2 C7 H7A 120.6 . . ?
C9 C8 C13 116.75(15) . . ?
C9 C8 C6 121.93(16) . . ?
C13 C8 C6 121.32(16) . . ?
C10 C9 C8 122.04(16) . . ?
C10 C9 H9A 119.0 . . ?
C8 C9 H9A 119.0 . . ?
C9 C10 C11 120.86(16) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
N1 C11 C12 121.44(17) . . ?
N1 C11 C10 121.65(17) . . ?
C12 C11 C10 116.90(15) . . ?
C13 C12 C11 121.21(17) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C12 C13 C8 122.22(17) . . ?
C12 C13 H13A 118.9 . . ?
C8 C13 H13A 118.9 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 C16 C17 116.05(16) . . ?
C23 C16 B1 125.03(15) . . ?
C17 C16 B1 118.90(16) . . ?
C19 C17 C16 120.78(18) . . ?
C19 C17 C18 117.22(16) . . ?
C16 C17 C18 121.98(17) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 122.61(17) . . ?
C20 C19 H19A 118.7 . . ?
C17 C19 H19A 118.7 . . ?
C19 C20 C22 116.86(17) . . ?
C19 C20 C21 122.04(17) . . ?
C22 C20 C21 121.09(19) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 C23 122.32(18) . . ?
C20 C22 H22A 118.8 . . ?
C23 C22 H22A 118.8 . . ?
C22 C23 C16 121.05(16) . . ?
C22 C23 C24 116.12(17) . . ?
C16 C23 C24 122.82(16) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C32 116.51(16) . . ?
C26 C25 B1 126.15(16) . . ?
C32 C25 B1 117.18(15) . . ?
C28 C26 C25 120.73(17) . . ?
C28 C26 C27 115.99(17) . . ?
C25 C26 C27 123.29(17) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C26 122.47(18) . . ?
C29 C28 H28A 118.8 . . ?
C26 C28 H28A 118.8 . . ?
C28 C29 C31 117.23(17) . . ?
C28 C29 C30 121.52(19) . . ?
C31 C29 C30 121.25(19) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 C32 122.25(18) . . ?
C29 C31 H31A 118.9 . . ?
C32 C31 H31A 118.9 . . ?
C31 C32 C25 120.80(17) . . ?
C31 C32 C33 116.15(16) . . ?
C25 C32 C33 123.03(16) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C39 120.0(2) . . ?
C35 C34 H34A 120.0 . . ?
C39 C34 H34A 120.0 . . ?
C34 C35 C36 119.9(2) . . ?
C34 C35 H35A 120.1 . . ?
C36 C35 H35A 120.1 . . ?
C37 C36 C35 120.2(2) . . ?
C37 C36 H36A 119.9 . . ?
C35 C36 H36A 119.9 . . ?
C36 C37 C38 120.2(2) . . ?
C36 C37 H37A 119.9 . . ?
C38 C37 H37A 119.9 . . ?
C37 C38 C39 119.7(2) . . ?
C37 C38 H38A 120.2 . . ?
C39 C38 H38A 120.2 . . ?
C38 C39 C34 120.1(2) . . ?
C38 C39 H39A 120.0 . . ?
C34 C39 H39A 120.0 . . ?

_refine_diff_density_max         0.685
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_sy15
_database_code_depnum_ccdc_archive 'CCDC 1569175'
_audit_update_record             
;
2017-08-15 deposited with the CCDC.
2018-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.12 H3.38 B0.12 O0.12'
_chemical_formula_weight         44.28

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                   8.4880(6)
_cell_length_b                   10.8609(7)
_cell_length_c                   12.4693(9)
_cell_angle_alpha                97.707(2)
_cell_angle_beta                 98.593(2)
_cell_angle_gamma                105.796(2)
_cell_volume                     1075.07(13)
_cell_formula_units_Z            16
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    8962
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      30.27

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.094
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.064
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28226
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.718
_diffrn_reflns_theta_max         30.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6553
_reflns_number_gt                4543
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+0.1051P] 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         6553
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.1768
_refine_ls_wR_factor_gt          0.1625
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.46924(18) 0.62084(14) 0.30714(12) 0.0255(3) Uani 1 1 d . . . . .
O1 O 0.36317(11) 0.52120(9) 0.37689(7) 0.0276(2) Uani 1 1 d . . . . .
C1 C 0.37592(18) 0.40922(13) 0.35134(11) 0.0309(3) Uani 1 1 d . . . . .
H1A H 0.3311 0.3405 0.3881 0.037 Uiso 1 1 calc R U . . .
C2 C 0.46212(17) 0.39176(13) 0.26339(11) 0.0295(3) Uani 1 1 d . . . . .
C3 C 0.4792(2) 0.27534(15) 0.21108(13) 0.0420(4) Uani 1 1 d . . . . .
H3A H 0.4386 0.1961 0.2363 0.050 Uiso 1 1 calc R U . . .
C4 C 0.5569(2) 0.27935(16) 0.12181(13) 0.0447(4) Uani 1 1 d . . . . .
H4A H 0.5721 0.2023 0.0849 0.054 Uiso 1 1 calc R U . . .
C5 C 0.61330(18) 0.39670(15) 0.08548(11) 0.0352(3) Uani 1 1 d . . . . .
H5A H 0.6645 0.3978 0.0228 0.042 Uiso 1 1 calc R U . . .
C6 C 0.59661(16) 0.51140(13) 0.13836(10) 0.0285(3) Uani 1 1 d . . . . .
H6A H 0.6359 0.5898 0.1116 0.034 Uiso 1 1 calc R U . . .
C7 C 0.52208(15) 0.51262(12) 0.23126(10) 0.0244(3) Uani 1 1 d . . . . .
C8 C 0.59986(16) 0.72446(12) 0.41064(10) 0.0246(3) Uani 1 1 d . . . . .
C9 C 0.77314(16) 0.74078(13) 0.43591(11) 0.0284(3) Uani 1 1 d . . . . .
C10 C 0.87468(17) 0.83388(14) 0.52604(11) 0.0334(3) Uani 1 1 d . . . . .
H10A H 0.9910 0.8438 0.5409 0.040 Uiso 1 1 calc R U . . .
C11 C 0.81205(18) 0.91218(13) 0.59449(11) 0.0322(3) Uani 1 1 d . . . . .
C12 C 0.64216(18) 0.89375(12) 0.57139(11) 0.0300(3) Uani 1 1 d . . . . .
H12A H 0.5962 0.9461 0.6173 0.036 Uiso 1 1 calc R U . . .
C13 C 0.53542(16) 0.80140(12) 0.48338(10) 0.0261(3) Uani 1 1 d . . . . .
C14 C 0.35070(17) 0.78547(14) 0.47317(12) 0.0341(3) Uani 1 1 d . . . . .
H14A H 0.3346 0.8549 0.5252 0.051 Uiso 1 1 calc R U . . .
H14B H 0.2945 0.7007 0.4899 0.051 Uiso 1 1 calc R U . . .
H14C H 0.3035 0.7904 0.3978 0.051 Uiso 1 1 calc R U . . .
C15 C 0.85883(18) 0.66060(16) 0.37103(13) 0.0417(4) Uani 1 1 d . . . . .
H15A H 0.9771 0.6847 0.4057 0.063 Uiso 1 1 calc R U . . .
H15B H 0.8487 0.6770 0.2953 0.063 Uiso 1 1 calc R U . . .
H15C H 0.8064 0.5680 0.3700 0.063 Uiso 1 1 calc R U . . .
C16 C 0.9246(2) 1.01010(17) 0.69159(14) 0.0485(4) Uani 1 1 d . . . . .
H16A H 0.8780 1.0824 0.7072 0.073 Uiso 1 1 calc R U . . .
H16B H 1.0357 1.0433 0.6745 0.073 Uiso 1 1 calc R U . . .
H16C H 0.9332 0.9684 0.7563 0.073 Uiso 1 1 calc R U . . .
C17 C 0.34991(16) 0.68015(13) 0.22585(10) 0.0273(3) Uani 1 1 d . . . . .
C18 C 0.17915(17) 0.61700(14) 0.18140(11) 0.0323(3) Uani 1 1 d . . . . .
C19 C 0.0887(2) 0.67163(17) 0.10842(13) 0.0426(4) Uani 1 1 d . . . . .
H19A H -0.0260 0.6271 0.0797 0.051 Uiso 1 1 calc R U . . .
C20 C 0.1593(2) 0.78773(17) 0.07638(13) 0.0474(4) Uani 1 1 d . . . . .
C21 C 0.3268(2) 0.84826(15) 0.11793(12) 0.0429(4) Uani 1 1 d . . . . .
H21A H 0.3785 0.9281 0.0969 0.051 Uiso 1 1 calc R U . . .
C22 C 0.42346(19) 0.79688(14) 0.18973(11) 0.0344(3) Uani 1 1 d . . . . .
C23 C 0.08539(18) 0.48921(16) 0.20737(14) 0.0446(4) Uani 1 1 d . . . . .
H23A H -0.0283 0.4601 0.1635 0.067 Uiso 1 1 calc R U . . .
H23B H 0.0809 0.5001 0.2860 0.067 Uiso 1 1 calc R U . . .
H23C H 0.1425 0.4242 0.1895 0.067 Uiso 1 1 calc R U . . .
C24 C 0.6071(2) 0.87028(16) 0.22322(15) 0.0471(4) Uani 1 1 d . . . . .
H24A H 0.6379 0.9307 0.1728 0.071 Uiso 1 1 calc R U . . .
H24B H 0.6724 0.8085 0.2199 0.071 Uiso 1 1 calc R U . . .
H24C H 0.6303 0.9193 0.2987 0.071 Uiso 1 1 calc R U . . .
C25 C 0.0592(3) 0.8454(2) -0.00242(18) 0.0801(8) Uani 1 1 d . . . . .
H25A H 0.1044 0.9405 0.0140 0.120 Uiso 1 1 calc R U . . .
H25B H -0.0576 0.8199 0.0060 0.120 Uiso 1 1 calc R U . . .
H25C H 0.0659 0.8131 -0.0784 0.120 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 C7 1.6104(19) . ?
B1 C8 1.6325(19) . ?
B1 C17 1.6406(19) . ?
B1 O1 1.6414(16) . ?
O1 C1 1.2532(16) . ?
C1 C2 1.4260(19) . ?
C1 H1A 0.9500 . ?
C2 C3 1.397(2) . ?
C2 C7 1.4075(18) . ?
C3 C4 1.375(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.395(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3821(19) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4006(18) . ?
C6 H6A 0.9500 . ?
C8 C9 1.4137(18) . ?
C8 C13 1.4192(18) . ?
C9 C10 1.3999(19) . ?
C9 C15 1.508(2) . ?
C10 C11 1.386(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.380(2) . ?
C11 C16 1.505(2) . ?
C12 C13 1.3943(18) . ?
C12 H12A 0.9500 . ?
C13 C14 1.5136(19) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.4126(19) . ?
C17 C22 1.4165(19) . ?
C18 C19 1.398(2) . ?
C18 C23 1.504(2) . ?
C19 C20 1.380(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.378(3) . ?
C20 C25 1.512(2) . ?
C21 C22 1.396(2) . ?
C21 H21A 0.9500 . ?
C22 C24 1.510(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C7 B1 C8 122.51(11) . . ?
C7 B1 C17 107.82(10) . . ?
C8 B1 C17 116.27(11) . . ?
C7 B1 O1 96.44(9) . . ?
C8 B1 O1 98.71(9) . . ?
C17 B1 O1 112.58(10) . . ?
C1 O1 B1 110.31(10) . . ?
O1 C1 C2 115.62(12) . . ?
O1 C1 H1A 122.2 . . ?
C2 C1 H1A 122.2 . . ?
C3 C2 C7 123.87(13) . . ?
C3 C2 C1 127.51(13) . . ?
C7 C2 C1 108.53(12) . . ?
C4 C3 C2 117.76(14) . . ?
C4 C3 H3A 121.1 . . ?
C2 C3 H3A 121.1 . . ?
C3 C4 C5 119.96(14) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 121.73(13) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C5 C6 C7 120.32(12) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C6 C7 C2 116.31(12) . . ?
C6 C7 B1 134.55(11) . . ?
C2 C7 B1 108.80(11) . . ?
C9 C8 C13 116.95(12) . . ?
C9 C8 B1 124.85(11) . . ?
C13 C8 B1 118.17(11) . . ?
C10 C9 C8 120.27(12) . . ?
C10 C9 C15 116.31(12) . . ?
C8 C9 C15 123.41(12) . . ?
C11 C10 C9 122.52(13) . . ?
C11 C10 H10A 118.7 . . ?
C9 C10 H10A 118.7 . . ?
C12 C11 C10 117.11(12) . . ?
C12 C11 C16 121.76(13) . . ?
C10 C11 C16 121.10(14) . . ?
C11 C12 C13 122.59(12) . . ?
C11 C12 H12A 118.7 . . ?
C13 C12 H12A 118.7 . . ?
C12 C13 C8 120.46(12) . . ?
C12 C13 C14 116.64(12) . . ?
C8 C13 C14 122.87(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 116.76(12) . . ?
C18 C17 B1 124.26(12) . . ?
C22 C17 B1 118.78(12) . . ?
C19 C18 C17 120.47(14) . . ?
C19 C18 C23 116.41(13) . . ?
C17 C18 C23 123.12(12) . . ?
C20 C19 C18 122.59(15) . . ?
C20 C19 H19A 118.7 . . ?
C18 C19 H19A 118.7 . . ?
C21 C20 C19 117.06(14) . . ?
C21 C20 C25 121.15(18) . . ?
C19 C20 C25 121.78(18) . . ?
C20 C21 C22 122.65(15) . . ?
C20 C21 H21A 118.7 . . ?
C22 C21 H21A 118.7 . . ?
C21 C22 C17 120.40(14) . . ?
C21 C22 C24 116.57(13) . . ?
C17 C22 C24 123.02(13) . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_sy10
_database_code_depnum_ccdc_archive 'CCDC 1568989'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2018-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.09 H3.66 B0.11 N0.11 O0.11'
_chemical_formula_weight         45.41

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                   12.3452(6)
_cell_length_b                   9.0371(5)
_cell_length_c                   20.4924(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.199(2)
_cell_angle_gamma                90
_cell_volume                     2285.7(2)
_cell_formula_units_Z            35
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      29.89

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43562
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.463
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6954
_reflns_number_gt                4901
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²+0.6670P] 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         6954
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.70241(13) 0.32460(17) 0.43380(7) 0.0231(3) Uani 1 1 d . . . . .
O1 O 0.75696(12) 0.58648(13) 0.60783(6) 0.0522(4) Uani 1 1 d . . . . .
N1 N 0.83940(12) 0.06156(15) 0.68021(6) 0.0349(3) Uani 1 1 d . . . . .
C1 C 0.73005(13) 0.50669(16) 0.56331(7) 0.0298(3) Uani 1 1 d . . . . .
H1 H 0.6922 0.5502 0.5273 0.036 Uiso 1 1 calc R U . . .
C2 C 0.75170(11) 0.34545(15) 0.56067(6) 0.0229(3) Uani 1 1 d . . . . .
C3 C 0.73013(11) 0.26259(15) 0.50309(6) 0.0233(3) Uani 1 1 d . . . . .
C4 C 0.74672(12) 0.10897(15) 0.50961(7) 0.0267(3) Uani 1 1 d . . . . .
H4 H 0.7302 0.0477 0.4731 0.032 Uiso 1 1 calc R U . . .
C5 C 0.78552(12) 0.04260(16) 0.56585(7) 0.0280(3) Uani 1 1 d . . . . .
H5 H 0.7987 -0.0610 0.5662 0.034 Uiso 1 1 calc R U . . .
C6 C 0.80591(11) 0.12619(16) 0.62286(7) 0.0257(3) Uani 1 1 d . . . . .
C7 C 0.78729(11) 0.27984(16) 0.61849(7) 0.0253(3) Uani 1 1 d . . . . .
H7 H 0.7994 0.3399 0.6560 0.030 Uiso 1 1 calc R U . . .
C8 C 0.87047(16) 0.1495(2) 0.73644(8) 0.0423(4) Uani 1 1 d . . . . .
H8A H 0.9306 0.2148 0.7252 0.064 Uiso 1 1 calc R U . . .
H8B H 0.8933 0.0840 0.7723 0.064 Uiso 1 1 calc R U . . .
H8C H 0.8086 0.2092 0.7500 0.064 Uiso 1 1 calc R U . . .
C9 C 0.85819(17) -0.09588(19) 0.68356(9) 0.0470(5) Uani 1 1 d . . . . .
H9A H 0.7940 -0.1485 0.6668 0.070 Uiso 1 1 calc R U . . .
H9B H 0.8725 -0.1247 0.7290 0.070 Uiso 1 1 calc R U . . .
H9C H 0.9208 -0.1214 0.6572 0.070 Uiso 1 1 calc R U . . .
C10 C 0.74993(11) 0.47986(15) 0.41350(6) 0.0236(3) Uani 1 1 d . . . . .
C11 C 0.68141(11) 0.59715(15) 0.39334(6) 0.0251(3) Uani 1 1 d . . . . .
C12 C 0.56089(12) 0.57477(19) 0.38403(8) 0.0358(4) Uani 1 1 d . . . . .
H12A H 0.5255 0.6710 0.3779 0.054 Uiso 1 1 calc R U . . .
H12B H 0.5319 0.5260 0.4227 0.054 Uiso 1 1 calc R U . . .
H12C H 0.5470 0.5128 0.3455 0.054 Uiso 1 1 calc R U . . .
C13 C 0.72427(12) 0.73714(16) 0.38222(7) 0.0284(3) Uani 1 1 d . . . . .
H13 H 0.6766 0.8164 0.3714 0.034 Uiso 1 1 calc R U . . .
C14 C 0.83493(13) 0.76379(16) 0.38658(7) 0.0298(3) Uani 1 1 d . . . . .
C15 C 0.88072(16) 0.91363(19) 0.37072(10) 0.0456(4) Uani 1 1 d . . . . .
H15A H 0.9109 0.9117 0.3269 0.068 Uiso 1 1 calc R U . . .
H15B H 0.9380 0.9388 0.4027 0.068 Uiso 1 1 calc R U . . .
H15C H 0.8230 0.9880 0.3723 0.068 Uiso 1 1 calc R U . . .
C16 C 0.90276(12) 0.64688(16) 0.40351(7) 0.0288(3) Uani 1 1 d . . . . .
H16 H 0.9788 0.6630 0.4054 0.035 Uiso 1 1 calc R U . . .
C17 C 0.86290(11) 0.50681(15) 0.41788(6) 0.0245(3) Uani 1 1 d . . . . .
C18 C 0.94315(12) 0.38592(17) 0.43466(8) 0.0323(3) Uani 1 1 d . . . . .
H18A H 0.9215 0.2944 0.4123 0.048 Uiso 1 1 calc R U . . .
H18B H 0.9446 0.3695 0.4819 0.048 Uiso 1 1 calc R U . . .
H18C H 1.0154 0.4154 0.4206 0.048 Uiso 1 1 calc R U . . .
C19 C 0.63282(11) 0.22607(15) 0.38542(6) 0.0230(3) Uani 1 1 d . . . . .
C21 C 0.66780(12) 0.19531(15) 0.32151(6) 0.0245(3) Uani 1 1 d . . . . .
C22 C 0.76999(14) 0.2601(2) 0.29427(7) 0.0366(4) Uani 1 1 d . . . . .
H22A H 0.7887 0.2073 0.2543 0.055 Uiso 1 1 calc R U . . .
H22B H 0.8293 0.2501 0.3265 0.055 Uiso 1 1 calc R U . . .
H22C H 0.7584 0.3651 0.2843 0.055 Uiso 1 1 calc R U . . .
C23 C 0.60870(12) 0.10007(15) 0.28114(7) 0.0274(3) Uani 1 1 d . . . . .
H23 H 0.6342 0.0796 0.2387 0.033 Uiso 1 1 calc R U . . .
C24 C 0.51375(12) 0.03417(16) 0.30108(7) 0.0293(3) Uani 1 1 d . . . . .
C25 C 0.45158(15) -0.0711(2) 0.25717(9) 0.0456(4) Uani 1 1 d . . . . .
H25A H 0.4531 -0.0350 0.2121 0.068 Uiso 1 1 calc R U . . .
H25B H 0.3763 -0.0772 0.2713 0.068 Uiso 1 1 calc R U . . .
H25C H 0.4849 -0.1694 0.2596 0.068 Uiso 1 1 calc R U . . .
C26 C 0.47692(12) 0.06793(16) 0.36292(7) 0.0292(3) Uani 1 1 d . . . . .
H26 H 0.4108 0.0258 0.3769 0.035 Uiso 1 1 calc R U . . .
C27 C 0.53426(11) 0.16178(16) 0.40494(7) 0.0259(3) Uani 1 1 d . . . . .
C28 C 0.48396(13) 0.19743(19) 0.46977(8) 0.0341(3) Uani 1 1 d . . . . .
H28A H 0.4969 0.3017 0.4805 0.051 Uiso 1 1 calc R U . . .
H28B H 0.5166 0.1347 0.5039 0.051 Uiso 1 1 calc R U . . .
H28C H 0.4058 0.1789 0.4669 0.051 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 C3 1.558(2) . ?
B1 C19 1.574(2) . ?
B1 C10 1.580(2) . ?
O1 C1 1.2041(18) . ?
N1 C6 1.3685(18) . ?
N1 C9 1.443(2) . ?
N1 C8 1.445(2) . ?
C1 C2 1.483(2) . ?
C1 H1 0.9500 . ?
C2 C7 1.3881(19) . ?
C2 C3 1.4180(18) . ?
C3 C4 1.4092(19) . ?
C4 C5 1.376(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.410(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.4125(19) . ?
C10 C17 1.4168(19) . ?
C11 C13 1.392(2) . ?
C11 C12 1.510(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C16 1.388(2) . ?
C14 C15 1.505(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.510(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C27 1.4136(19) . ?
C19 C21 1.4152(18) . ?
C21 C23 1.3900(19) . ?
C21 C22 1.508(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.384(2) . ?
C23 H23 0.9500 . ?
C24 C26 1.389(2) . ?
C24 C25 1.508(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.3916(19) . ?
C26 H26 0.9500 . ?
C27 C28 1.513(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C3 B1 C19 118.50(12) . . ?
C3 B1 C10 118.94(12) . . ?
C19 B1 C10 122.49(12) . . ?
C6 N1 C9 120.47(14) . . ?
C6 N1 C8 121.36(13) . . ?
C9 N1 C8 117.68(13) . . ?
O1 C1 C2 124.69(14) . . ?
O1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C7 C2 C3 122.37(13) . . ?
C7 C2 C1 116.27(12) . . ?
C3 C2 C1 121.23(12) . . ?
C4 C3 C2 114.64(12) . . ?
C4 C3 B1 118.00(12) . . ?
C2 C3 B1 127.03(12) . . ?
C5 C4 C3 123.78(13) . . ?
C5 C4 H4 118.1 . . ?
C3 C4 H4 118.1 . . ?
C4 C5 C6 120.90(13) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
N1 C6 C5 121.91(13) . . ?
N1 C6 C7 121.39(13) . . ?
C5 C6 C7 116.68(12) . . ?
C2 C7 C6 121.54(13) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C17 118.18(13) . . ?
C11 C10 B1 121.34(12) . . ?
C17 C10 B1 120.43(12) . . ?
C13 C11 C10 120.17(13) . . ?
C13 C11 C12 118.56(13) . . ?
C10 C11 C12 121.27(13) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 121.60(14) . . ?
C14 C13 H13 119.2 . . ?
C11 C13 H13 119.2 . . ?
C16 C14 C13 118.16(14) . . ?
C16 C14 C15 120.76(15) . . ?
C13 C14 C15 121.04(14) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 C17 122.08(14) . . ?
C14 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C10 119.66(13) . . ?
C16 C17 C18 118.24(13) . . ?
C10 C17 C18 122.04(13) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C27 C19 C21 117.53(12) . . ?
C27 C19 B1 121.06(12) . . ?
C21 C19 B1 121.39(12) . . ?
C23 C21 C19 120.38(13) . . ?
C23 C21 C22 116.93(12) . . ?
C19 C21 C22 122.68(13) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 121.87(13) . . ?
C24 C23 H23 119.1 . . ?
C21 C23 H23 119.1 . . ?
C23 C24 C26 118.04(13) . . ?
C23 C24 C25 121.26(14) . . ?
C26 C24 C25 120.70(14) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 C27 121.76(14) . . ?
C24 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C19 120.34(13) . . ?
C26 C27 C28 117.41(13) . . ?
C19 C27 C28 122.17(13) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_junwei1sr
_database_code_depnum_ccdc_archive 'CCDC 1585930'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2018-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H34 B N O'
_chemical_formula_weight         411.37

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                   10.146(3)
_cell_length_b                   16.684(5)
_cell_length_c                   16.550(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.602(8)
_cell_angle_gamma                90
_cell_volume                     2722.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4174
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.21

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.004
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20210
_diffrn_reflns_av_unetI/netI     0.1240
_diffrn_reflns_av_R_equivalents  0.1136
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.399
_diffrn_reflns_theta_max         27.157
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5935
_reflns_number_gt                3197
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0950P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5935
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1395
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.2050
_refine_ls_wR_factor_gt          0.1781
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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 0.5868(2) 0.65221(17) 0.33336(16) 0.0319(6) Uani 1 1 d . . . . .
O1 O 0.52647(14) 0.68054(9) 0.41152(9) 0.0315(4) Uani 1 1 d . . . . .
N1 N 0.8771(2) 0.40298(15) 0.55238(14) 0.0501(6) Uani 1 1 d . . . . .
C1 C 0.6755(2) 0.57853(14) 0.38042(14) 0.0297(5) Uani 1 1 d . . . . .
C2 C 0.7705(2) 0.52561(16) 0.36165(15) 0.0387(6) Uani 1 1 d . . . . .
H2 H 0.7912 0.5283 0.3086 0.046 Uiso 1 1 calc R U . . .
C3 C 0.8350(2) 0.46946(16) 0.41851(16) 0.0407(6) Uani 1 1 d . . . . .
H3 H 0.8982 0.4342 0.4028 0.049 Uiso 1 1 calc R U . . .
C4 C 0.8116(2) 0.46210(15) 0.49855(15) 0.0371(6) Uani 1 1 d . . . . .
C5 C 0.7225(2) 0.51586(15) 0.52118(15) 0.0344(6) Uani 1 1 d . . . . .
H5 H 0.7053 0.5145 0.5752 0.041 Uiso 1 1 calc R U . . .
C6 C 0.6578(2) 0.57269(14) 0.46175(14) 0.0307(5) Uani 1 1 d . . . . .
C7 C 0.5651(2) 0.63461(14) 0.47410(14) 0.0298(5) Uani 1 1 d . . . . .
C8 C 0.5168(2) 0.64994(17) 0.54987(15) 0.0425(6) Uani 1 1 d . . . . .
H8A H 0.4475 0.6920 0.5388 0.064 Uiso 1 1 calc R U . . .
H8B H 0.5930 0.6673 0.5946 0.064 Uiso 1 1 calc R U . . .
H8C H 0.4779 0.6007 0.5667 0.064 Uiso 1 1 calc R U . . .
C9 C 0.8556(3) 0.39574(19) 0.63491(18) 0.0570(8) Uani 1 1 d . . . . .
H9A H 0.7601 0.3833 0.6316 0.086 Uiso 1 1 calc R U . . .
H9B H 0.8793 0.4464 0.6648 0.086 Uiso 1 1 calc R U . . .
H9C H 0.9127 0.3526 0.6646 0.086 Uiso 1 1 calc R U . . .
C10 C 0.9660(3) 0.34610(19) 0.5259(2) 0.0580(8) Uani 1 1 d . . . . .
H10A H 0.9150 0.3163 0.4775 0.087 Uiso 1 1 calc R U . . .
H10B H 1.0022 0.3087 0.5713 0.087 Uiso 1 1 calc R U . . .
H10C H 1.0410 0.3748 0.5108 0.087 Uiso 1 1 calc R U . . .
C11 C 0.6922(2) 0.71930(14) 0.31241(14) 0.0311(5) Uani 1 1 d . . . . .
C12 C 0.7316(2) 0.71209(16) 0.23600(15) 0.0388(6) Uani 1 1 d . . . . .
C13 C 0.6720(3) 0.64876(19) 0.17240(16) 0.0540(8) Uani 1 1 d . . . . .
H13A H 0.5803 0.6647 0.1430 0.081 Uiso 1 1 calc R U . . .
H13B H 0.6682 0.5974 0.2006 0.081 Uiso 1 1 calc R U . . .
H13C H 0.7290 0.6432 0.1324 0.081 Uiso 1 1 calc R U . . .
C14 C 0.8258(3) 0.76492(18) 0.21573(17) 0.0475(7) Uani 1 1 d . . . . .
H14 H 0.8489 0.7589 0.1636 0.057 Uiso 1 1 calc R U . . .
C15 C 0.8865(2) 0.82523(17) 0.26812(18) 0.0473(7) Uani 1 1 d . . . . .
C16 C 0.9871(3) 0.8817(2) 0.2447(2) 0.0707(10) Uani 1 1 d . . . . .
H16A H 0.9650 0.8890 0.1843 0.106 Uiso 1 1 calc R U . . .
H16B H 1.0786 0.8593 0.2629 0.106 Uiso 1 1 calc R U . . .
H16C H 0.9834 0.9336 0.2719 0.106 Uiso 1 1 calc R U . . .
C17 C 0.8511(2) 0.83183(15) 0.34328(16) 0.0382(6) Uani 1 1 d . . . . .
H17 H 0.8924 0.8727 0.3808 0.046 Uiso 1 1 calc R U . . .
C18 C 0.7573(2) 0.78105(15) 0.36665(15) 0.0339(6) Uani 1 1 d . . . . .
C19 C 0.7313(3) 0.79613(18) 0.45070(17) 0.0478(7) Uani 1 1 d . . . . .
H19A H 0.7807 0.8441 0.4750 0.072 Uiso 1 1 calc R U . . .
H19B H 0.7621 0.7499 0.4868 0.072 Uiso 1 1 calc R U . . .
H19C H 0.6339 0.8042 0.4453 0.072 Uiso 1 1 calc R U . . .
C21 C 0.3901(2) 0.56296(15) 0.23460(15) 0.0353(6) Uani 1 1 d . . . . .
C22 C 0.4635(3) 0.48493(17) 0.25618(19) 0.0570(8) Uani 1 1 d . . . . .
H22A H 0.4032 0.4405 0.2329 0.086 Uiso 1 1 calc R U . . .
H22B H 0.4913 0.4794 0.3168 0.086 Uiso 1 1 calc R U . . .
H22C H 0.5439 0.4840 0.2330 0.086 Uiso 1 1 calc R U . . .
C23 C 0.2605(2) 0.55728(17) 0.18157(17) 0.0455(7) Uani 1 1 d . . . . .
H23 H 0.2262 0.5057 0.1633 0.055 Uiso 1 1 calc R U . . .
C24 C 0.1807(2) 0.62346(18) 0.15484(17) 0.0489(7) Uani 1 1 d . . . . .
C25 C 0.0399(3) 0.6150(2) 0.0987(2) 0.0792(11) Uani 1 1 d . . . . .
H25A H 0.0286 0.6536 0.0530 0.119 Uiso 1 1 calc R U . . .
H25B H -0.0281 0.6253 0.1308 0.119 Uiso 1 1 calc R U . . .
H25C H 0.0282 0.5605 0.0760 0.119 Uiso 1 1 calc R U . . .
C26 C 0.2337(2) 0.69752(17) 0.18202(17) 0.0454(7) Uani 1 1 d . . . . .
H26 H 0.1813 0.7441 0.1638 0.054 Uiso 1 1 calc R U . . .
C27 C 0.3612(2) 0.70633(15) 0.23510(15) 0.0349(6) Uani 1 1 d . . . . .
C28 C 0.4052(2) 0.79093(16) 0.25923(18) 0.0464(7) Uani 1 1 d . . . . .
H28A H 0.4804 0.8056 0.2343 0.070 Uiso 1 1 calc R U . . .
H28B H 0.4347 0.7948 0.3199 0.070 Uiso 1 1 calc R U . . .
H28C H 0.3289 0.8275 0.2392 0.070 Uiso 1 1 calc R U . . .
C29 C 0.4438(2) 0.63876(14) 0.26375(13) 0.0301(5) Uani 1 1 d . . . . .


_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 C1 1.612(3) . ?
B1 O1 1.626(3) . ?
B1 C11 1.640(4) . ?
B1 C29 1.642(3) . ?
O1 C7 1.274(3) . ?
N1 C4 1.389(3) . ?
N1 C9 1.438(4) . ?
N1 C10 1.447(4) . ?
C1 C2 1.396(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C5 C6 1.412(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.444(3) . ?
C7 C8 1.472(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.418(3) . ?
C11 C18 1.423(3) . ?
C12 C14 1.398(4) . ?
C12 C13 1.513(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9500 . ?
C15 C17 1.378(4) . ?
C15 C16 1.505(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.395(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.497(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 C23 1.402(3) . ?
C21 C29 1.416(3) . ?
C21 C22 1.500(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.379(4) . ?
C23 H23 0.9500 . ?
C24 C26 1.380(4) . ?
C24 C25 1.516(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.390(3) . ?
C26 H26 0.9500 . ?
C27 C29 1.418(3) . ?
C27 C28 1.506(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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 B1 O1 96.26(17) . . ?
C1 B1 C11 107.75(18) . . ?
O1 B1 C11 110.84(19) . . ?
C1 B1 C29 122.4(2) . . ?
O1 B1 C29 99.33(16) . . ?
C11 B1 C29 117.23(19) . . ?
C7 O1 B1 111.75(17) . . ?
C4 N1 C9 120.8(2) . . ?
C4 N1 C10 120.6(2) . . ?
C9 N1 C10 118.5(2) . . ?
C2 C1 C6 114.9(2) . . ?
C2 C1 B1 135.4(2) . . ?
C6 C1 B1 109.5(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 123.0(2) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C5 C4 N1 122.0(2) . . ?
C5 C4 C3 117.6(2) . . ?
N1 C4 C3 120.3(2) . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 124.9(2) . . ?
C1 C6 C7 108.71(19) . . ?
C5 C6 C7 126.4(2) . . ?
O1 C7 C6 113.7(2) . . ?
O1 C7 C8 119.2(2) . . ?
C6 C7 C8 127.1(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C18 116.0(2) . . ?
C12 C11 B1 117.7(2) . . ?
C18 C11 B1 126.1(2) . . ?
C14 C12 C11 120.8(2) . . ?
C14 C12 C13 117.2(2) . . ?
C11 C12 C13 121.9(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 122.7(3) . . ?
C15 C14 H14 118.7 . . ?
C12 C14 H14 118.7 . . ?
C14 C15 C17 117.0(2) . . ?
C14 C15 C16 121.7(3) . . ?
C17 C15 C16 121.2(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 122.8(2) . . ?
C15 C17 H17 118.6 . . ?
C18 C17 H17 118.6 . . ?
C17 C18 C11 120.7(2) . . ?
C17 C18 C19 115.9(2) . . ?
C11 C18 C19 123.4(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C21 C29 120.2(2) . . ?
C23 C21 C22 115.5(2) . . ?
C29 C21 C22 124.4(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C21 122.7(2) . . ?
C24 C23 H23 118.7 . . ?
C21 C23 H23 118.7 . . ?
C23 C24 C26 117.2(2) . . ?
C23 C24 C25 121.3(3) . . ?
C26 C24 C25 121.5(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 C27 122.3(2) . . ?
C24 C26 H26 118.9 . . ?
C27 C26 H26 118.9 . . ?
C26 C27 C29 121.1(2) . . ?
C26 C27 C28 116.1(2) . . ?
C29 C27 C28 122.8(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C21 C29 C27 116.53(19) . . ?
C21 C29 B1 124.5(2) . . ?
C27 C29 B1 118.7(2) . . ?

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.065
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 1.000 0.500 230 51 ' '
2 0.500 0.500 1.000 230 51 ' '
_platon_squeeze_details          
;Disordered hexane solvent molecules were removed by Squeeze 
;

