# Electronic Supplementary Material (ESI) for ChemComm.
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 2181492'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-02-17 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_audit_creation_date             2022-06-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 B N O6'
_chemical_formula_sum            'C22 H26 B N O6'
_chemical_formula_weight         411.25
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        Pc
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   15.3311(2)
_cell_length_b                   10.06926(11)
_cell_length_c                   13.62417(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.3120(13)
_cell_angle_gamma                90
_cell_volume                     2062.35(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17270
_cell_measurement_temperature    173
_cell_measurement_theta_max      76.7610
_cell_measurement_theta_min      2.9510
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29685
_diffrn_reflns_point_group_measured_fraction_full 0.858
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.955
_diffrn_reflns_theta_min         2.939
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   0.50    5.00    --  -25.00  60.00  36.00  360
  2  ω   -115.00  32.00   0.50    5.00    --  -25.00  60.00   0.00  294
  3  ω    -22.00  23.00   0.50    5.00    --  -25.00  40.00 -72.00   90
  4  ω   -193.00 -13.00   0.50   10.00    -- -103.00  46.00-144.00  360
  5  ω   -162.00 -13.00   0.50   10.00    -- -103.00  60.00  36.00  298
  6  ω   -193.00 -29.50   0.50   10.00    -- -103.00  60.00 -36.00  327
  7  ω   -167.00 -13.00   0.50   10.00    -- -103.00  60.00 108.00  308
  8  ω   -167.00 -43.00   0.50   10.00    -- -103.00  26.00 144.00  248
  9  ω   -175.50 -13.00   0.50   10.00    -- -103.00  60.00-108.00  325
 10  ω   -193.00 -17.00   0.50   10.00    -- -103.00  60.00-180.00  352
 11  ω   -153.00 -15.00   0.50   10.00    -- -103.00  40.00  36.00  276
 12  ω   -114.50 -44.50   0.50   10.00    -- -103.00  40.00 -36.00  140
 13  ω   -137.00 -22.00   0.50   10.00    -- -103.00  53.00 108.00  230
 14  ω    -69.00 -24.00   0.50   10.00    -- -103.00  60.00 -72.00   90
 15  ω    -60.00 -15.00   0.50   10.00    -- -103.00  46.00-108.00   90
 16  ω    -60.00 -14.00   0.50   10.00    -- -103.00  40.00-108.00   92
 17  ω    -60.00 -13.00   0.50   10.00    -- -103.00  53.00-108.00   94
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0945135000
_diffrn_orient_matrix_UB_12      0.0331922000
_diffrn_orient_matrix_UB_13      0.0570129000
_diffrn_orient_matrix_UB_21      0.0308744000
_diffrn_orient_matrix_UB_22      -0.1409698000
_diffrn_orient_matrix_UB_23      -0.0207988000
_diffrn_orient_matrix_UB_31      0.0247905000
_diffrn_orient_matrix_UB_32      0.0492455000
_diffrn_orient_matrix_UB_33      -0.0980769000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.715
_reflns_Friedel_fraction_max     0.702
_reflns_number_gt                6742
_reflns_number_total             7388
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011  (Burla et al.,  2007)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 2593 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         7388
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0900P)²+0.1076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1224
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C18(H18A,H18B),
 C21(H21A,H21B), C35(H35A,H35B), C38(H38A,H38B), C40(H40A,H40B), C42(H42A,H42B),
  C48(H48A,H48B), C51(H51A,H51B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C33(H33), C44(H44)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C24(H24A,H24B,
 H24C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C54(H54A,
 H54B,H54C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.20605(16) 0.7444(2) 0.5679(2) 0.0472(6) Uani 1 1 d . . . . .
O11 O 0.19596(17) 0.2979(2) 0.5753(2) 0.0446(6) Uani 1 1 d . . . . .
O19 O 0.80778(19) 0.6827(3) 0.9303(2) 0.0538(6) Uani 1 1 d . . . . .
O20 O 0.71135(14) 0.71245(19) 0.78554(16) 0.0345(5) Uani 1 1 d . . . . .
O22 O 0.76805(18) 0.6843(2) 0.49974(18) 0.0465(6) Uani 1 1 d . . . . .
O23 O 0.67317(13) 0.69219(18) 0.60551(16) 0.0318(4) Uani 1 1 d . . . . .
O37 O 0.88443(16) 0.2393(2) 0.7236(2) 0.0461(6) Uani 1 1 d . . . . .
O41 O 0.90069(17) -0.2085(2) 0.7283(2) 0.0453(6) Uani 1 1 d . . . . .
O49 O 0.29079(19) 0.1821(3) 0.8205(2) 0.0570(7) Uani 1 1 d . . . . .
O50 O 0.38516(14) 0.21411(19) 0.71657(17) 0.0352(5) Uani 1 1 d . . . . .
O52 O 0.32776(19) 0.1874(2) 0.40635(18) 0.0461(6) Uani 1 1 d . . . . .
O53 O 0.42392(13) 0.19449(18) 0.55314(16) 0.0314(4) Uani 1 1 d . . . . .
N1 N 0.72495(17) 0.5010(2) 0.7089(2) 0.0299(5) Uani 1 1 d . . . . .
N31 N 0.37200(16) 0.0033(2) 0.63353(19) 0.0283(5) Uani 1 1 d . . . . .
C1 C 0.55860(18) 0.6081(2) 0.7046(2) 0.0269(5) Uani 1 1 d . . . . .
C2 C 0.5216(2) 0.6109(3) 0.7920(2) 0.0323(6) Uani 1 1 d . . . . .
C3 C 0.4315(2) 0.5836(3) 0.7855(2) 0.0334(6) Uani 1 1 d . . . . .
H3 H 0.407005 0.586632 0.844344 0.040 Uiso 1 1 calc R U . . .
C4 C 0.37724(19) 0.5522(3) 0.6949(2) 0.0289(6) Uani 1 1 d . . . . .
C5 C 0.2795(2) 0.5217(3) 0.6749(2) 0.0333(6) Uani 1 1 d . . . . .
H5A H 0.246355 0.591319 0.703481 0.040 Uiso 1 1 calc R U . . .
H5B H 0.268225 0.434856 0.704166 0.040 Uiso 1 1 calc R U . . .
C6 C 0.25163(19) 0.5182(3) 0.5597(2) 0.0294(6) Uani 1 1 d . . . . .
C7 C 0.20049(19) 0.6439(3) 0.5173(2) 0.0332(6) Uani 1 1 d . . . . .
C8 C 0.1489(2) 0.6391(3) 0.4116(3) 0.0373(7) Uani 1 1 d . . . . .
H8A H 0.191082 0.643653 0.365216 0.045 Uiso 1 1 calc R U . . .
H8B H 0.109838 0.718113 0.399305 0.045 Uiso 1 1 calc R U . . .
C9 C 0.0914(2) 0.5135(3) 0.3879(3) 0.0360(7) Uani 1 1 d . . . . .
C10 C 0.1535(2) 0.3925(3) 0.4127(2) 0.0355(6) Uani 1 1 d . . . . .
H10A H 0.118468 0.309869 0.397766 0.043 Uiso 1 1 calc R U . . .
H10B H 0.198913 0.394225 0.370142 0.043 Uiso 1 1 calc R U . . .
C11 C 0.19883(19) 0.3928(3) 0.5208(2) 0.0319(6) Uani 1 1 d . . . . .
C12 C 0.34107(19) 0.5175(3) 0.5179(2) 0.0287(5) Uani 1 1 d . . . . .
H12A H 0.351607 0.429392 0.490180 0.034 Uiso 1 1 calc R U . . .
H12B H 0.339505 0.585553 0.465113 0.034 Uiso 1 1 calc R U . . .
C13 C 0.41175(17) 0.5495(2) 0.6087(2) 0.0249(5) Uani 1 1 d . . . . .
C14 C 0.50118(18) 0.5770(2) 0.6133(2) 0.0251(5) Uani 1 1 d . . . . .
H14 H 0.524278 0.574753 0.553516 0.030 Uiso 1 1 calc R U . . .
C15 C 0.5742(3) 0.6453(5) 0.8953(3) 0.0513(9) Uani 1 1 d . . . . .
H15A H 0.619353 0.576886 0.916897 0.077 Uiso 1 1 calc R U . . .
H15B H 0.533921 0.649797 0.942840 0.077 Uiso 1 1 calc R U . . .
H15C H 0.603395 0.731542 0.892824 0.077 Uiso 1 1 calc R U . . .
C16 C 0.0196(2) 0.5110(4) 0.4512(3) 0.0476(8) Uani 1 1 d . . . . .
H16A H -0.016594 0.430612 0.435782 0.071 Uiso 1 1 calc R U . . .
H16B H -0.018431 0.589518 0.436118 0.071 Uiso 1 1 calc R U . . .
H16C H 0.047614 0.511128 0.522320 0.071 Uiso 1 1 calc R U . . .
C17 C 0.0493(3) 0.5105(4) 0.2769(3) 0.0462(8) Uani 1 1 d . . . . .
H17A H 0.095916 0.517370 0.237209 0.069 Uiso 1 1 calc R U . . .
H17B H 0.008036 0.585310 0.261093 0.069 Uiso 1 1 calc R U . . .
H17C H 0.016815 0.426939 0.261131 0.069 Uiso 1 1 calc R U . . .
C18 C 0.7741(3) 0.5008(3) 0.8134(3) 0.0454(8) Uani 1 1 d . . . . .
H18A H 0.836767 0.474351 0.816721 0.054 Uiso 1 1 calc R U . . .
H18B H 0.746500 0.438154 0.854378 0.054 Uiso 1 1 calc R U . . .
C19 C 0.7688(2) 0.6417(3) 0.8506(2) 0.0377(7) Uani 1 1 d . . . . .
C21 C 0.7857(2) 0.5328(3) 0.6374(3) 0.0402(7) Uani 1 1 d . . . . .
H21A H 0.844779 0.561274 0.674500 0.048 Uiso 1 1 calc R U . . .
H21B H 0.793453 0.453856 0.596596 0.048 Uiso 1 1 calc R U . . .
C22 C 0.7415(2) 0.6430(3) 0.5719(2) 0.0328(6) Uani 1 1 d . . . . .
C24 C 0.6773(2) 0.3739(3) 0.6772(3) 0.0457(8) Uani 1 1 d . . . . .
H24A H 0.720684 0.301897 0.679795 0.069 Uiso 1 1 calc R U . . .
H24B H 0.643328 0.383008 0.608701 0.069 Uiso 1 1 calc R U . . .
H24C H 0.636626 0.353485 0.722403 0.069 Uiso 1 1 calc R U . . .
C31 C 0.53803(18) 0.1093(2) 0.7025(2) 0.0276(5) Uani 1 1 d . . . . .
C32 C 0.5753(2) 0.1116(3) 0.8068(2) 0.0330(6) Uani 1 1 d . . . . .
C33 C 0.6651(2) 0.0804(3) 0.8397(2) 0.0334(6) Uani 1 1 d . . . . .
H33 H 0.689875 0.082524 0.909297 0.040 Uiso 1 1 calc R U . . .
C34 C 0.71849(19) 0.0467(3) 0.7728(2) 0.0284(5) Uani 1 1 d . . . . .
C35 C 0.8158(2) 0.0121(3) 0.7954(2) 0.0328(6) Uani 1 1 d . . . . .
H35A H 0.825462 -0.076363 0.827348 0.039 Uiso 1 1 calc R U . . .
H35B H 0.850115 0.078944 0.840490 0.039 Uiso 1 1 calc R U . . .
C36 C 0.84357(19) 0.0121(3) 0.6932(2) 0.0297(6) Uani 1 1 d . . . . .
C37 C 0.89236(18) 0.1407(3) 0.6751(2) 0.0322(6) Uani 1 1 d . . . . .
C38 C 0.9451(2) 0.1413(3) 0.5929(3) 0.0366(7) Uani 1 1 d . . . . .
H38A H 0.983502 0.221239 0.600221 0.044 Uiso 1 1 calc R U . . .
H38B H 0.903545 0.147533 0.527571 0.044 Uiso 1 1 calc R U . . .
C39 C 1.0036(2) 0.0177(3) 0.5928(3) 0.0349(6) Uani 1 1 d . . . . .
C40 C 0.9436(2) -0.1059(3) 0.5882(3) 0.0360(6) Uani 1 1 d . . . . .
H40A H 0.898692 -0.104352 0.525117 0.043 Uiso 1 1 calc R U . . .
H40B H 0.980252 -0.186838 0.587857 0.043 Uiso 1 1 calc R U . . .
C41 C 0.89730(19) -0.1113(3) 0.6753(2) 0.0322(6) Uani 1 1 d . . . . .
C42 C 0.75404(19) 0.0116(3) 0.6116(2) 0.0285(5) Uani 1 1 d . . . . .
H42A H 0.756046 0.078765 0.559001 0.034 Uiso 1 1 calc R U . . .
H42B H 0.742885 -0.076839 0.579956 0.034 Uiso 1 1 calc R U . . .
C43 C 0.68412(17) 0.0458(2) 0.6709(2) 0.0252(5) Uani 1 1 d . . . . .
C44 C 0.59498(18) 0.0762(2) 0.6365(2) 0.0261(5) Uani 1 1 d . . . . .
H44 H 0.571702 0.074593 0.566585 0.031 Uiso 1 1 calc R U . . .
C45 C 0.5233(3) 0.1491(5) 0.8863(3) 0.0507(9) Uani 1 1 d . . . . .
H45A H 0.476430 0.083262 0.887417 0.076 Uiso 1 1 calc R U . . .
H45B H 0.496341 0.236843 0.871055 0.076 Uiso 1 1 calc R U . . .
H45C H 0.563422 0.151529 0.951763 0.076 Uiso 1 1 calc R U . . .
C46 C 1.0749(2) 0.0138(4) 0.6882(3) 0.0484(9) Uani 1 1 d . . . . .
H46A H 1.046453 0.013643 0.746673 0.073 Uiso 1 1 calc R U . . .
H46B H 1.113260 0.092091 0.690695 0.073 Uiso 1 1 calc R U . . .
H46C H 1.110781 -0.066784 0.688581 0.073 Uiso 1 1 calc R U . . .
C47 C 1.0472(3) 0.0213(4) 0.5014(3) 0.0474(8) Uani 1 1 d . . . . .
H47A H 1.085673 -0.056550 0.501982 0.071 Uiso 1 1 calc R U . . .
H47B H 1.082914 0.102314 0.502991 0.071 Uiso 1 1 calc R U . . .
H47C H 1.001088 0.020477 0.440352 0.071 Uiso 1 1 calc R U . . .
C48 C 0.3269(2) -0.0003(3) 0.7196(3) 0.0423(8) Uani 1 1 d . . . . .
H48A H 0.358398 -0.060535 0.772290 0.051 Uiso 1 1 calc R U . . .
H48B H 0.264711 -0.030938 0.698679 0.051 Uiso 1 1 calc R U . . .
C49 C 0.3298(2) 0.1424(3) 0.7576(3) 0.0399(7) Uani 1 1 d . . . . .
C51 C 0.3094(2) 0.0384(3) 0.5382(3) 0.0383(7) Uani 1 1 d . . . . .
H51A H 0.251897 0.069844 0.552261 0.046 Uiso 1 1 calc R U . . .
H51B H 0.298141 -0.039863 0.493432 0.046 Uiso 1 1 calc R U . . .
C52 C 0.3542(2) 0.1468(3) 0.4904(2) 0.0333(6) Uani 1 1 d . . . . .
C54 C 0.4195(2) -0.1234(3) 0.6207(3) 0.0410(7) Uani 1 1 d . . . . .
H54A H 0.462935 -0.142533 0.682054 0.062 Uiso 1 1 calc R U . . .
H54B H 0.450343 -0.114418 0.564503 0.062 Uiso 1 1 calc R U . . .
H54C H 0.376377 -0.196153 0.607228 0.062 Uiso 1 1 calc R U . . .
B1 B 0.6611(2) 0.6358(3) 0.7018(3) 0.0277(6) Uani 1 1 d . . . . .
B31 B 0.4361(2) 0.1380(3) 0.6547(2) 0.0274(6) 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
O7 C7 1.217(4) . ?
O11 C11 1.216(4) . ?
O19 C19 1.205(4) . ?
O20 C19 1.328(4) . ?
O20 B1 1.465(4) . ?
O22 C22 1.208(4) . ?
O23 C22 1.320(4) . ?
O23 B1 1.474(4) . ?
O37 C37 1.212(4) . ?
O41 C41 1.211(4) . ?
O49 C49 1.206(4) . ?
O50 C49 1.319(4) . ?
O50 B31 1.471(4) . ?
O52 C52 1.209(4) . ?
O53 C52 1.321(4) . ?
O53 B31 1.474(4) . ?
N1 C18 1.474(4) . ?
N1 C21 1.508(4) . ?
N1 C24 1.495(4) . ?
N1 B1 1.664(4) . ?
N31 C48 1.474(4) . ?
N31 C51 1.499(4) . ?
N31 C54 1.496(4) . ?
N31 B31 1.667(4) . ?
C1 C2 1.417(4) . ?
C1 C14 1.411(4) . ?
C1 B1 1.604(4) . ?
C2 C3 1.393(4) . ?
C2 C15 1.519(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 C5 1.501(4) . ?
C4 C13 1.380(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.543(4) . ?
C6 C7 1.540(4) . ?
C6 C11 1.538(4) . ?
C6 C12 1.585(4) . ?
C7 C8 1.502(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.539(4) . ?
C9 C10 1.542(4) . ?
C9 C16 1.527(5) . ?
C9 C17 1.523(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.500(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.511(4) . ?
C13 C14 1.388(4) . ?
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 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.514(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.500(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C31 C32 1.424(4) . ?
C31 C44 1.410(4) . ?
C31 B31 1.597(4) . ?
C32 C33 1.398(4) . ?
C32 C45 1.513(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.382(4) . ?
C34 C35 1.504(4) . ?
C34 C43 1.385(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.533(5) . ?
C36 C37 1.539(4) . ?
C36 C41 1.537(4) . ?
C36 C42 1.588(4) . ?
C37 C38 1.505(5) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.534(4) . ?
C39 C40 1.542(4) . ?
C39 C46 1.526(5) . ?
C39 C47 1.526(5) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C40 C41 1.500(5) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C42 C43 1.503(4) . ?
C43 C44 1.389(4) . ?
C44 H44 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.524(5) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C51 C52 1.504(4) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 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
C19 O20 B1 114.6(2) . . ?
C22 O23 B1 114.3(2) . . ?
C49 O50 B31 114.5(2) . . ?
C52 O53 B31 113.8(2) . . ?
C18 N1 C21 111.2(3) . . ?
C18 N1 C24 113.9(3) . . ?
C18 N1 B1 103.9(2) . . ?
C21 N1 B1 102.7(2) . . ?
C24 N1 C21 108.9(3) . . ?
C24 N1 B1 115.6(2) . . ?
C48 N31 C51 112.0(3) . . ?
C48 N31 C54 112.8(2) . . ?
C48 N31 B31 103.5(2) . . ?
C51 N31 B31 102.3(2) . . ?
C54 N31 C51 110.1(3) . . ?
C54 N31 B31 115.5(2) . . ?
C2 C1 B1 124.9(3) . . ?
C14 C1 C2 117.5(3) . . ?
C14 C1 B1 117.6(2) . . ?
C1 C2 C15 123.8(3) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 C15 116.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 127.8(3) . . ?
C13 C4 C3 120.0(3) . . ?
C13 C4 C5 112.1(3) . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
C4 C5 C6 104.9(2) . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
C5 C6 C12 106.2(2) . . ?
C7 C6 C5 112.5(2) . . ?
C7 C6 C12 106.3(2) . . ?
C11 C6 C5 113.0(2) . . ?
C11 C6 C7 110.5(2) . . ?
C11 C6 C12 107.8(2) . . ?
O7 C7 C6 119.8(3) . . ?
O7 C7 C8 122.4(3) . . ?
C8 C7 C6 117.8(3) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C7 C8 C9 113.6(3) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C8 C9 C10 107.5(2) . . ?
C16 C9 C8 110.0(3) . . ?
C16 C9 C10 110.2(3) . . ?
C17 C9 C8 109.8(3) . . ?
C17 C9 C10 109.0(3) . . ?
C17 C9 C16 110.3(3) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.2(3) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
O11 C11 C6 121.0(3) . . ?
O11 C11 C10 122.2(3) . . ?
C10 C11 C6 116.8(2) . . ?
C6 C12 H12A 111.0 . . ?
C6 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 C6 103.7(2) . . ?
C13 C12 H12A 111.0 . . ?
C13 C12 H12B 111.0 . . ?
C4 C13 C12 111.6(2) . . ?
C4 C13 C14 119.9(3) . . ?
C14 C13 C12 128.5(2) . . ?
C1 C14 H14 119.2 . . ?
C13 C14 C1 121.6(2) . . ?
C13 C14 H14 119.2 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 110.6 . . ?
N1 C18 H18B 110.6 . . ?
N1 C18 C19 105.7(3) . . ?
H18A C18 H18B 108.7 . . ?
C19 C18 H18A 110.6 . . ?
C19 C18 H18B 110.6 . . ?
O19 C19 O20 124.4(3) . . ?
O19 C19 C18 125.0(3) . . ?
O20 C19 C18 110.6(3) . . ?
N1 C21 H21A 110.5 . . ?
N1 C21 H21B 110.5 . . ?
H21A C21 H21B 108.7 . . ?
C22 C21 N1 106.1(2) . . ?
C22 C21 H21A 110.5 . . ?
C22 C21 H21B 110.5 . . ?
O22 C22 O23 124.8(3) . . ?
O22 C22 C21 123.6(3) . . ?
O23 C22 C21 111.5(3) . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C32 C31 B31 124.9(3) . . ?
C44 C31 C32 117.6(3) . . ?
C44 C31 B31 117.5(2) . . ?
C31 C32 C45 123.6(3) . . ?
C33 C32 C31 119.6(3) . . ?
C33 C32 C45 116.8(3) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 C32 121.2(3) . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C35 127.9(3) . . ?
C33 C34 C43 120.3(3) . . ?
C43 C34 C35 111.8(3) . . ?
C34 C35 H35A 110.8 . . ?
C34 C35 H35B 110.8 . . ?
C34 C35 C36 104.8(2) . . ?
H35A C35 H35B 108.9 . . ?
C36 C35 H35A 110.8 . . ?
C36 C35 H35B 110.8 . . ?
C35 C36 C37 112.1(2) . . ?
C35 C36 C41 113.4(2) . . ?
C35 C36 C42 106.3(2) . . ?
C37 C36 C42 105.7(2) . . ?
C41 C36 C37 111.2(2) . . ?
C41 C36 C42 107.6(2) . . ?
O37 C37 C36 119.8(3) . . ?
O37 C37 C38 121.9(3) . . ?
C38 C37 C36 118.2(2) . . ?
C37 C38 H38A 108.9 . . ?
C37 C38 H38B 108.9 . . ?
C37 C38 C39 113.4(3) . . ?
H38A C38 H38B 107.7 . . ?
C39 C38 H38A 108.9 . . ?
C39 C38 H38B 108.9 . . ?
C38 C39 C40 108.2(2) . . ?
C46 C39 C38 110.0(3) . . ?
C46 C39 C40 109.6(3) . . ?
C46 C39 C47 109.9(3) . . ?
C47 C39 C38 109.3(3) . . ?
C47 C39 C40 109.8(3) . . ?
C39 C40 H40A 109.3 . . ?
C39 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
C41 C40 C39 111.6(3) . . ?
C41 C40 H40A 109.3 . . ?
C41 C40 H40B 109.3 . . ?
O41 C41 C36 121.4(3) . . ?
O41 C41 C40 122.0(3) . . ?
C40 C41 C36 116.6(2) . . ?
C36 C42 H42A 111.1 . . ?
C36 C42 H42B 111.1 . . ?
H42A C42 H42B 109.0 . . ?
C43 C42 C36 103.4(2) . . ?
C43 C42 H42A 111.1 . . ?
C43 C42 H42B 111.1 . . ?
C34 C43 C42 111.6(2) . . ?
C34 C43 C44 119.5(3) . . ?
C44 C43 C42 128.9(2) . . ?
C31 C44 H44 119.0 . . ?
C43 C44 C31 121.9(3) . . ?
C43 C44 H44 119.0 . . ?
C32 C45 H45A 109.5 . . ?
C32 C45 H45B 109.5 . . ?
C32 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C39 C46 H46A 109.5 . . ?
C39 C46 H46B 109.5 . . ?
C39 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C39 C47 H47A 109.5 . . ?
C39 C47 H47B 109.5 . . ?
C39 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
N31 C48 H48A 110.7 . . ?
N31 C48 H48B 110.7 . . ?
N31 C48 C49 105.1(2) . . ?
H48A C48 H48B 108.8 . . ?
C49 C48 H48A 110.7 . . ?
C49 C48 H48B 110.7 . . ?
O49 C49 O50 124.7(3) . . ?
O49 C49 C48 124.6(3) . . ?
O50 C49 C48 110.5(3) . . ?
N31 C51 H51A 110.5 . . ?
N31 C51 H51B 110.5 . . ?
N31 C51 C52 106.1(2) . . ?
H51A C51 H51B 108.7 . . ?
C52 C51 H51A 110.5 . . ?
C52 C51 H51B 110.5 . . ?
O52 C52 O53 124.6(3) . . ?
O52 C52 C51 124.0(3) . . ?
O53 C52 C51 111.4(3) . . ?
N31 C54 H54A 109.5 . . ?
N31 C54 H54B 109.5 . . ?
N31 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O20 B1 O23 110.6(2) . . ?
O20 B1 N1 99.8(2) . . ?
O20 B1 C1 116.1(3) . . ?
O23 B1 N1 101.1(2) . . ?
O23 B1 C1 112.5(2) . . ?
C1 B1 N1 115.1(2) . . ?
O50 B31 O53 110.7(2) . . ?
O50 B31 N31 99.3(2) . . ?
O50 B31 C31 116.6(2) . . ?
O53 B31 N31 101.0(2) . . ?
O53 B31 C31 112.7(2) . . ?
C31 B31 N31 114.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 C7 C8 C9 -136.5(3) . . . . ?
O37 C37 C38 C39 137.7(3) . . . . ?
N1 C18 C19 O19 -173.3(3) . . . . ?
N1 C18 C19 O20 10.1(4) . . . . ?
N1 C21 C22 O22 -172.7(3) . . . . ?
N1 C21 C22 O23 10.1(3) . . . . ?
N31 C48 C49 O49 171.2(3) . . . . ?
N31 C48 C49 O50 -12.6(4) . . . . ?
N31 C51 C52 O52 170.1(3) . . . . ?
N31 C51 C52 O53 -11.9(3) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C2 C1 C14 C13 -0.3(4) . . . . ?
C2 C1 B1 O20 -22.1(4) . . . . ?
C2 C1 B1 O23 -151.0(3) . . . . ?
C2 C1 B1 N1 94.0(3) . . . . ?
C2 C3 C4 C5 -179.4(3) . . . . ?
C2 C3 C4 C13 -1.0(4) . . . . ?
C3 C4 C5 C6 170.5(3) . . . . ?
C3 C4 C13 C12 -178.1(2) . . . . ?
C3 C4 C13 C14 0.7(4) . . . . ?
C4 C5 C6 C7 -104.1(3) . . . . ?
C4 C5 C6 C11 129.8(2) . . . . ?
C4 C5 C6 C12 11.8(3) . . . . ?
C4 C13 C14 C1 -0.1(4) . . . . ?
C5 C4 C13 C12 0.5(3) . . . . ?
C5 C4 C13 C14 179.3(2) . . . . ?
C5 C6 C7 O7 19.1(4) . . . . ?
C5 C6 C7 C8 -164.1(3) . . . . ?
C5 C6 C11 O11 -13.2(4) . . . . ?
C5 C6 C11 C10 168.3(2) . . . . ?
C5 C6 C12 C13 -11.5(3) . . . . ?
C6 C7 C8 C9 46.8(4) . . . . ?
C6 C12 C13 C4 7.0(3) . . . . ?
C6 C12 C13 C14 -171.7(2) . . . . ?
C7 C6 C11 O11 -140.3(3) . . . . ?
C7 C6 C11 C10 41.2(4) . . . . ?
C7 C6 C12 C13 108.5(2) . . . . ?
C7 C8 C9 C10 -55.8(4) . . . . ?
C7 C8 C9 C16 64.2(3) . . . . ?
C7 C8 C9 C17 -174.2(3) . . . . ?
C8 C9 C10 C11 59.5(3) . . . . ?
C9 C10 C11 O11 126.3(3) . . . . ?
C9 C10 C11 C6 -55.1(3) . . . . ?
C11 C6 C7 O7 146.4(3) . . . . ?
C11 C6 C7 C8 -36.7(4) . . . . ?
C11 C6 C12 C13 -132.9(2) . . . . ?
C12 C6 C7 O7 -96.8(3) . . . . ?
C12 C6 C7 C8 80.1(3) . . . . ?
C12 C6 C11 O11 103.9(3) . . . . ?
C12 C6 C11 C10 -74.7(3) . . . . ?
C12 C13 C14 C1 178.5(2) . . . . ?
C13 C4 C5 C6 -8.0(3) . . . . ?
C14 C1 C2 C3 -0.1(4) . . . . ?
C14 C1 C2 C15 -178.8(3) . . . . ?
C14 C1 B1 O20 158.7(2) . . . . ?
C14 C1 B1 O23 29.9(3) . . . . ?
C14 C1 B1 N1 -85.1(3) . . . . ?
C15 C2 C3 C4 179.5(3) . . . . ?
C16 C9 C10 C11 -60.4(3) . . . . ?
C17 C9 C10 C11 178.4(3) . . . . ?
C18 N1 C21 C22 -128.8(3) . . . . ?
C18 N1 B1 O20 22.5(3) . . . . ?
C18 N1 B1 O23 135.9(3) . . . . ?
C18 N1 B1 C1 -102.6(3) . . . . ?
C19 O20 B1 O23 -123.7(3) . . . . ?
C19 O20 B1 N1 -17.9(3) . . . . ?
C19 O20 B1 C1 106.6(3) . . . . ?
C21 N1 C18 C19 90.0(3) . . . . ?
C21 N1 B1 O20 -93.4(3) . . . . ?
C21 N1 B1 O23 20.0(3) . . . . ?
C21 N1 B1 C1 141.4(3) . . . . ?
C22 O23 B1 O20 89.5(3) . . . . ?
C22 O23 B1 N1 -15.6(3) . . . . ?
C22 O23 B1 C1 -138.9(2) . . . . ?
C24 N1 C18 C19 -146.5(3) . . . . ?
C24 N1 C21 C22 104.9(3) . . . . ?
C24 N1 B1 O20 148.2(3) . . . . ?
C24 N1 B1 O23 -98.4(3) . . . . ?
C24 N1 B1 C1 23.0(4) . . . . ?
C31 C32 C33 C34 -0.4(4) . . . . ?
C32 C31 C44 C43 0.4(4) . . . . ?
C32 C31 B31 O50 21.5(4) . . . . ?
C32 C31 B31 O53 151.1(3) . . . . ?
C32 C31 B31 N31 -94.1(3) . . . . ?
C32 C33 C34 C35 179.3(3) . . . . ?
C32 C33 C34 C43 1.4(4) . . . . ?
C33 C34 C35 C36 -168.6(3) . . . . ?
C33 C34 C43 C42 177.8(3) . . . . ?
C33 C34 C43 C44 -1.5(4) . . . . ?
C34 C35 C36 C37 101.0(3) . . . . ?
C34 C35 C36 C41 -132.1(2) . . . . ?
C34 C35 C36 C42 -14.0(3) . . . . ?
C34 C43 C44 C31 0.6(4) . . . . ?
C35 C34 C43 C42 -0.5(3) . . . . ?
C35 C34 C43 C44 -179.7(2) . . . . ?
C35 C36 C37 O37 -19.5(4) . . . . ?
C35 C36 C37 C38 163.6(3) . . . . ?
C35 C36 C41 O41 13.9(4) . . . . ?
C35 C36 C41 C40 -167.2(2) . . . . ?
C35 C36 C42 C43 13.7(3) . . . . ?
C36 C37 C38 C39 -45.5(4) . . . . ?
C36 C42 C43 C34 -8.4(3) . . . . ?
C36 C42 C43 C44 170.8(2) . . . . ?
C37 C36 C41 O41 141.3(3) . . . . ?
C37 C36 C41 C40 -39.8(4) . . . . ?
C37 C36 C42 C43 -105.5(2) . . . . ?
C37 C38 C39 C40 55.1(4) . . . . ?
C37 C38 C39 C46 -64.6(3) . . . . ?
C37 C38 C39 C47 174.6(3) . . . . ?
C38 C39 C40 C41 -59.1(3) . . . . ?
C39 C40 C41 O41 -127.3(3) . . . . ?
C39 C40 C41 C36 53.8(3) . . . . ?
C41 C36 C37 O37 -147.7(3) . . . . ?
C41 C36 C37 C38 35.5(4) . . . . ?
C41 C36 C42 C43 135.5(2) . . . . ?
C42 C36 C37 O37 95.8(3) . . . . ?
C42 C36 C37 C38 -81.0(3) . . . . ?
C42 C36 C41 O41 -103.3(3) . . . . ?
C42 C36 C41 C40 75.6(3) . . . . ?
C42 C43 C44 C31 -178.5(3) . . . . ?
C43 C34 C35 C36 9.4(3) . . . . ?
C44 C31 C32 C33 -0.5(4) . . . . ?
C44 C31 C32 C45 178.2(3) . . . . ?
C44 C31 B31 O50 -160.1(2) . . . . ?
C44 C31 B31 O53 -30.5(3) . . . . ?
C44 C31 B31 N31 84.3(3) . . . . ?
C45 C32 C33 C34 -179.1(3) . . . . ?
C46 C39 C40 C41 60.8(3) . . . . ?
C47 C39 C40 C41 -178.4(3) . . . . ?
C48 N31 C51 C52 130.9(3) . . . . ?
C48 N31 B31 O50 -25.6(3) . . . . ?
C48 N31 B31 O53 -138.9(2) . . . . ?
C48 N31 B31 C31 99.6(3) . . . . ?
C49 O50 B31 O53 125.1(3) . . . . ?
C49 O50 B31 N31 19.5(3) . . . . ?
C49 O50 B31 C31 -104.4(3) . . . . ?
C51 N31 C48 C49 -86.5(3) . . . . ?
C51 N31 B31 O50 91.0(2) . . . . ?
C51 N31 B31 O53 -22.3(3) . . . . ?
C51 N31 B31 C31 -143.8(3) . . . . ?
C52 O53 B31 O50 -87.6(3) . . . . ?
C52 O53 B31 N31 16.9(3) . . . . ?
C52 O53 B31 C31 139.9(2) . . . . ?
C54 N31 C48 C49 148.6(3) . . . . ?
C54 N31 C51 C52 -102.8(3) . . . . ?
C54 N31 B31 O50 -149.3(3) . . . . ?
C54 N31 B31 O53 97.3(3) . . . . ?
C54 N31 B31 C31 -24.2(4) . . . . ?
B1 O20 C19 O19 -170.2(3) . . . . ?
B1 O20 C19 C18 6.4(4) . . . . ?
B1 O23 C22 O22 -172.6(3) . . . . ?
B1 O23 C22 C21 4.6(3) . . . . ?
B1 N1 C18 C19 -19.8(3) . . . . ?
B1 N1 C21 C22 -18.1(3) . . . . ?
B1 C1 C2 C3 -179.2(3) . . . . ?
B1 C1 C2 C15 2.1(5) . . . . ?
B1 C1 C14 C13 179.0(2) . . . . ?
B31 O50 C49 O49 170.1(3) . . . . ?
B31 O50 C49 C48 -6.1(4) . . . . ?
B31 O53 C52 O52 173.5(3) . . . . ?
B31 O53 C52 C51 -4.5(3) . . . . ?
B31 N31 C48 C49 23.0(3) . . . . ?
B31 N31 C51 C52 20.5(3) . . . . ?
B31 C31 C32 C33 177.9(3) . . . . ?
B31 C31 C32 C45 -3.4(5) . . . . ?
B31 C31 C44 C43 -178.1(2) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/diethyl ether'
####################################################################### 
# 
# 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_33
_database_code_depnum_ccdc_archive 'CCDC 2181494'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-06-23 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_audit_creation_date             2022-06-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O3 S'
_chemical_formula_sum            'C17 H17 N O3 S'
_chemical_formula_weight         315.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1250(4)
_cell_length_b                   7.7985(2)
_cell_length_c                   12.6248(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.692(2)
_cell_angle_gamma                90
_cell_volume                     1481.78(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7905
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5530
_cell_measurement_theta_min      2.7190
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19815
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.110
_diffrn_reflns_theta_min         2.707
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00  89.00   0.50   10.00    --    0.00  42.00 -90.00   52
  2  ω    -35.00  76.00   0.50   10.00    --  -12.80  42.00 -30.00  222
  3  ω     51.00  76.00   0.50   10.00    --  -12.80  42.00   0.00   50
  4  ω     36.00  70.00   0.50   10.00    --  -12.80  42.00  30.00   68
  5  ω     39.00  64.00   0.50   10.00    --  -12.80  42.00 120.00   50
  6  ω    -39.00  74.00   0.50   10.00    --  -12.80  42.00 -90.00  226
  7  ω    -28.00  76.00   0.50   10.00    --  -12.80  42.00 150.00  208
  8  ω    -53.00 -26.00   0.50   10.00    --  -12.80  42.00-150.00   54
  9  ω    -11.00  74.00   0.50   10.00    --  -12.80  42.00-150.00  170
 10  ω     48.00  73.00   0.50   10.00    --  -12.80  42.00 -60.00   50
 11  ω     -8.00  74.00   0.50   10.00    --  -12.80  42.00  60.00  164
 12  ω    -83.00 -58.00   0.50   10.00    --  -12.80  42.00 -30.00   50
;
_diffrn_measurement_device       'AFC8: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0470538000
_diffrn_orient_matrix_UB_12      -0.0036247000
_diffrn_orient_matrix_UB_13      -0.0035812000
_diffrn_orient_matrix_UB_21      0.0004018000
_diffrn_orient_matrix_UB_22      0.0504406000
_diffrn_orient_matrix_UB_23      0.0467968000
_diffrn_orient_matrix_UB_31      -0.0025116000
_diffrn_orient_matrix_UB_32      0.0756058000
_diffrn_orient_matrix_UB_33      -0.0313998000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2826
_reflns_number_total             3514
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       ?
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3514
_refine_ls_number_restraints     380
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.4636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1017
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O6-C5 = O6A-C9
 1.36 with sigma of 0.02
 C8-C9 = C8A-C5
 1.5 with sigma of 0.02
 O6A-C7A = O6-C7
 1.45 with sigma of 0.02
 C8-C7 = C7A-C8A
 1.51 with sigma of 0.02
 C4-C3 = C4-C5 = C9-C5 = C5A-C9A = C9-C10 = C4A-C5A = C4A-C3A = C10-C11 = C3-
 C11 = C11A-C3A = C10A-C11A = C9A-C10A
 1.39 with sigma of 0.02
 C11A-C12A = C2A-C3A
 1.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O6 \\sim O6A \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C7A
\\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
4. Others
 Sof(O6A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=
 Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(C10A)=
 Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=1-FVAR(1)
 Sof(O6)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(C7)=
 Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C2A(H2AA,H2AB),
 C7A(H7AA,H7AB), C8A(H8AA,H8AB), C12A(H12C,H12D)
5.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18), C4(H4), C10(H10), C4A(H4A), C10A(H10A)
5.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29614(2) 0.65708(5) 0.76430(3) 0.03783(13) Uani 1 1 d . . . . .
O1 O 0.25512(8) 0.82245(16) 0.75789(11) 0.0536(3) Uani 1 1 d . . . . .
O2 O 0.32027(8) 0.57948(18) 0.86547(8) 0.0512(3) Uani 1 1 d . . . . .
O6 O 0.02893(18) 0.2015(4) 0.32611(19) 0.0531(9) Uani 0.550(5) 1 d D U P A 1
O6A O 0.1060(2) -0.1081(4) 0.4666(3) 0.0486(10) Uani 0.450(5) 1 d D U P A 2
N1 N 0.22717(8) 0.52696(17) 0.69945(10) 0.0351(3) Uani 1 1 d . . . . .
C13 C 0.39221(9) 0.66796(19) 0.69590(11) 0.0298(3) Uani 1 1 d . . . . .
C14 C 0.46605(10) 0.5711(2) 0.73168(12) 0.0340(3) Uani 1 1 d . . . . .
H14 H 0.465509 0.501721 0.793489 0.041 Uiso 1 1 calc R U . . .
C15 C 0.54068(10) 0.5765(2) 0.67625(13) 0.0369(3) Uani 1 1 d . . . . .
H15 H 0.591828 0.512133 0.701437 0.044 Uiso 1 1 calc R U . . .
C16 C 0.54190(10) 0.6742(2) 0.58471(12) 0.0353(3) Uani 1 1 d . . . . .
C17 C 0.46676(10) 0.7689(2) 0.54968(11) 0.0352(3) Uani 1 1 d . . . . .
H17 H 0.466526 0.835374 0.486592 0.042 Uiso 1 1 calc R U . . .
C18 C 0.39250(10) 0.76802(19) 0.60504(12) 0.0336(3) Uani 1 1 d . . . . .
H18 H 0.342053 0.835274 0.581155 0.040 Uiso 1 1 calc R U . . .
C19 C 0.62277(12) 0.6783(3) 0.52426(15) 0.0513(5) Uani 1 1 d . . . . .
H19A H 0.605795 0.647785 0.449704 0.077 Uiso 1 1 calc R U . . .
H19B H 0.666731 0.595894 0.555757 0.077 Uiso 1 1 calc R U . . .
H19C H 0.648437 0.793741 0.527954 0.077 Uiso 1 1 calc R U . . .
C2 C 0.1809(9) 0.5761(15) 0.5885(12) 0.051(3) Uani 0.550(5) 1 d . U P A 1
H2A H 0.130192 0.654111 0.595523 0.062 Uiso 0.550(5) 1 calc R U P A 1
H2B H 0.223237 0.633296 0.544916 0.062 Uiso 0.550(5) 1 calc R U P A 1
C3 C 0.1507(18) 0.415(2) 0.5408(16) 0.033(2) Uani 0.550(5) 1 d D U P A 1
C4 C 0.0965(6) 0.4027(9) 0.4462(6) 0.0366(13) Uani 0.550(5) 1 d D U P A 1
H4 H 0.073180 0.499317 0.407013 0.044 Uiso 0.550(5) 1 calc R U P A 1
C5 C 0.0801(6) 0.2393(9) 0.4152(6) 0.0350(13) Uani 0.550(5) 1 d D U P A 1
C7 C 0.0302(3) 0.0162(6) 0.3131(3) 0.0397(11) Uani 0.550(5) 1 d D U P A 1
H7A H 0.056932 -0.014085 0.247069 0.048 Uiso 0.550(5) 1 calc R U P A 1
H7B H -0.031066 -0.029695 0.307923 0.048 Uiso 0.550(5) 1 calc R U P A 1
C8 C 0.0853(2) -0.0606(5) 0.4098(4) 0.0364(8) Uani 0.550(5) 1 d D U P A 1
H8A H 0.048506 -0.133262 0.452411 0.044 Uiso 0.550(5) 1 calc R U P A 1
H8B H 0.135846 -0.128714 0.388455 0.044 Uiso 0.550(5) 1 calc R U P A 1
C9 C 0.1162(5) 0.0978(9) 0.4688(5) 0.0288(12) Uani 0.550(5) 1 d D U P A 1
C10 C 0.1693(6) 0.1191(12) 0.5643(6) 0.0334(14) Uani 0.550(5) 1 d D U P A 1
H10 H 0.194321 0.022287 0.601928 0.040 Uiso 0.550(5) 1 calc R U P A 1
C11 C 0.1855(12) 0.2837(17) 0.6041(11) 0.0270(18) Uani 0.550(5) 1 d D U P A 1
C12 C 0.2406(9) 0.3489(17) 0.6990(11) 0.037(3) Uani 0.550(5) 1 d . U P A 1
H12A H 0.222015 0.296464 0.764629 0.044 Uiso 0.550(5) 1 calc R U P A 1
H12B H 0.304115 0.322064 0.694284 0.044 Uiso 0.550(5) 1 calc R U P A 1
C2A C 0.2486(11) 0.3304(19) 0.7112(12) 0.0246(17) Uani 0.450(5) 1 d D U P A 2
H2AA H 0.312687 0.306680 0.709324 0.030 Uiso 0.450(5) 1 calc R U P A 2
H2AB H 0.228196 0.281948 0.777041 0.030 Uiso 0.450(5) 1 calc R U P A 2
C3A C 0.1941(15) 0.265(2) 0.6126(15) 0.034(3) Uani 0.450(5) 1 d D U P A 2
C4A C 0.1789(7) 0.0921(13) 0.5914(8) 0.0293(15) Uani 0.450(5) 1 d D U P A 2
H4A H 0.201847 0.004300 0.638539 0.035 Uiso 0.450(5) 1 calc R U P A 2
C5A C 0.1287(6) 0.0574(13) 0.4984(6) 0.0297(13) Uani 0.450(5) 1 d D U P A 2
C7A C 0.0567(3) -0.0982(7) 0.3624(4) 0.0431(13) Uani 0.450(5) 1 d D U P A 2
H7AA H -0.000341 -0.160385 0.362590 0.052 Uiso 0.450(5) 1 calc R U P A 2
H7AB H 0.091269 -0.151563 0.308536 0.052 Uiso 0.450(5) 1 calc R U P A 2
C8A C 0.0393(3) 0.0907(9) 0.3353(4) 0.0407(13) Uani 0.450(5) 1 d D U P A 2
H8AA H -0.024641 0.119006 0.333452 0.049 Uiso 0.450(5) 1 calc R U P A 2
H8AB H 0.060733 0.121325 0.266121 0.049 Uiso 0.450(5) 1 calc R U P A 2
C9A C 0.0944(5) 0.1813(11) 0.4290(6) 0.0310(16) Uani 0.450(5) 1 d D U P A 2
C10A C 0.1080(7) 0.3535(12) 0.4569(9) 0.044(2) Uani 0.450(5) 1 d D U P A 2
H10A H 0.082977 0.439822 0.410051 0.053 Uiso 0.450(5) 1 calc R U P A 2
C11A C 0.158(2) 0.404(2) 0.5532(19) 0.035(3) Uani 0.450(5) 1 d D U P A 2
C12A C 0.1832(9) 0.5808(13) 0.6012(13) 0.031(2) Uani 0.450(5) 1 d D U P A 2
H12C H 0.223159 0.644816 0.557845 0.037 Uiso 0.450(5) 1 calc R U P A 2
H12D H 0.130024 0.651074 0.610768 0.037 Uiso 0.450(5) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4300(14) . ?
S1 O2 1.4278(12) . ?
S1 N1 1.6183(13) . ?
S1 C13 1.7643(14) . ?
O6 C5 1.333(8) . ?
O6 C7 1.455(5) . ?
O6A C5A 1.385(11) . ?
O6A C7A 1.448(5) . ?
N1 C2 1.551(15) . ?
N1 C12 1.404(14) . ?
N1 C2A 1.571(16) . ?
N1 C12A 1.413(16) . ?
C13 C14 1.386(2) . ?
C13 C18 1.388(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 C17 1.390(2) . ?
C16 C19 1.505(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.446(15) . ?
C3 C4 1.384(12) . ?
C3 C11 1.373(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.348(10) . ?
C5 C9 1.379(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.530(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.494(8) . ?
C9 C10 1.391(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(11) . ?
C11 C12 1.481(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.512(16) . ?
C3A C4A 1.388(15) . ?
C3A C11A 1.396(15) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.360(9) . ?
C5A C9A 1.371(7) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.529(7) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.549(10) . ?
C9A C10A 1.399(11) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.423(14) . ?
C11A C12A 1.539(16) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 106.41(7) . . ?
O1 S1 C13 107.62(7) . . ?
O2 S1 O1 120.26(8) . . ?
O2 S1 N1 106.35(7) . . ?
O2 S1 C13 107.96(7) . . ?
N1 S1 C13 107.66(6) . . ?
C5 O6 C7 107.6(4) . . ?
C5A O6A C7A 107.7(4) . . ?
C2 N1 S1 120.8(4) . . ?
C12 N1 S1 122.4(5) . . ?
C12 N1 C2 107.1(7) . . ?
C2A N1 S1 116.6(5) . . ?
C12A N1 S1 118.8(4) . . ?
C12A N1 C2A 116.6(7) . . ?
C14 C13 S1 119.35(11) . . ?
C14 C13 C18 120.49(13) . . ?
C18 C13 S1 120.12(11) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.26(14) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.09(14) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 118.64(13) . . ?
C15 C16 C19 120.87(15) . . ?
C17 C16 C19 120.48(15) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.11(14) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 120.3 . . ?
C17 C18 C13 119.39(14) . . ?
C17 C18 H18 120.3 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C2 H2A 110.8 . . ?
N1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 N1 104.9(10) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C4 C3 C2 123.8(14) . . ?
C11 C3 C2 108.6(11) . . ?
C11 C3 C4 127.5(13) . . ?
C3 C4 H4 123.4 . . ?
C5 C4 C3 113.2(8) . . ?
C5 C4 H4 123.4 . . ?
O6 C5 C4 121.9(4) . . ?
O6 C5 C9 113.9(6) . . ?
C4 C5 C9 124.1(6) . . ?
O6 C7 H7A 110.1 . . ?
O6 C7 H7B 110.1 . . ?
O6 C7 C8 108.1(3) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
C7 C8 H8A 111.5 . . ?
C7 C8 H8B 111.5 . . ?
H8A C8 H8B 109.4 . . ?
C9 C8 C7 101.1(3) . . ?
C9 C8 H8A 111.5 . . ?
C9 C8 H8B 111.5 . . ?
C5 C9 C8 109.1(5) . . ?
C5 C9 C10 119.8(6) . . ?
C10 C9 C8 131.0(6) . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(8) . . ?
C11 C10 H10 120.4 . . ?
C3 C11 C10 115.9(11) . . ?
C3 C11 C12 111.5(11) . . ?
C10 C11 C12 132.3(13) . . ?
N1 C12 C11 105.8(10) . . ?
N1 C12 H12A 110.6 . . ?
N1 C12 H12B 110.6 . . ?
C11 C12 H12A 110.6 . . ?
C11 C12 H12B 110.6 . . ?
H12A C12 H12B 108.7 . . ?
N1 C2A H2AA 111.9 . . ?
N1 C2A H2AB 111.9 . . ?
H2AA C2A H2AB 109.6 . . ?
C3A C2A N1 99.3(12) . . ?
C3A C2A H2AA 111.9 . . ?
C3A C2A H2AB 111.9 . . ?
C4A C3A C2A 123.6(15) . . ?
C4A C3A C11A 127.0(15) . . ?
C11A C3A C2A 109.3(13) . . ?
C3A C4A H4A 122.4 . . ?
C5A C4A C3A 115.3(10) . . ?
C5A C4A H4A 122.4 . . ?
C4A C5A O6A 122.5(6) . . ?
C4A C5A C9A 123.7(8) . . ?
C9A C5A O6A 113.8(6) . . ?
O6A C7A H7AA 110.0 . . ?
O6A C7A H7AB 110.0 . . ?
O6A C7A C8A 108.5(4) . . ?
H7AA C7A H7AB 108.4 . . ?
C8A C7A H7AA 110.0 . . ?
C8A C7A H7AB 110.0 . . ?
C7A C8A H8AA 111.5 . . ?
C7A C8A H8AB 111.5 . . ?
C7A C8A C9A 101.6(5) . . ?
H8AA C8A H8AB 109.3 . . ?
C9A C8A H8AA 111.5 . . ?
C9A C8A H8AB 111.5 . . ?
C5A C9A C8A 107.9(6) . . ?
C5A C9A C10A 118.6(7) . . ?
C10A C9A C8A 133.3(7) . . ?
C9A C10A H10A 118.9 . . ?
C9A C10A C11A 122.2(10) . . ?
C11A C10A H10A 118.9 . . ?
C3A C11A C10A 113.0(14) . . ?
C3A C11A C12A 114.7(13) . . ?
C10A C11A C12A 132.2(16) . . ?
N1 C12A C11A 98.9(10) . . ?
N1 C12A H12C 112.0 . . ?
N1 C12A H12D 112.0 . . ?
C11A C12A H12C 112.0 . . ?
C11A C12A H12D 112.0 . . ?
H12C C12A H12D 109.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C2 C3 160.9(14) . . . . ?
S1 N1 C12 C11 -159.7(8) . . . . ?
S1 N1 C2A C3A -159.7(10) . . . . ?
S1 N1 C12A C11A 158.9(15) . . . . ?
S1 C13 C14 C15 178.39(11) . . . . ?
S1 C13 C18 C17 -177.02(11) . . . . ?
O1 S1 N1 C2 45.9(6) . . . . ?
O1 S1 N1 C12 -172.5(7) . . . . ?
O1 S1 N1 C2A -169.5(7) . . . . ?
O1 S1 N1 C12A 42.7(7) . . . . ?
O1 S1 C13 C14 146.48(12) . . . . ?
O1 S1 C13 C18 -35.77(14) . . . . ?
O2 S1 N1 C2 175.2(6) . . . . ?
O2 S1 N1 C12 -43.2(7) . . . . ?
O2 S1 N1 C2A -40.1(7) . . . . ?
O2 S1 N1 C12A 172.0(7) . . . . ?
O2 S1 C13 C14 15.28(14) . . . . ?
O2 S1 C13 C18 -166.97(12) . . . . ?
O6 C5 C9 C8 -0.7(8) . . . . ?
O6 C5 C9 C10 -178.5(8) . . . . ?
O6 C7 C8 C9 -3.4(4) . . . . ?
O6A C5A C9A C8A 0.3(9) . . . . ?
O6A C5A C9A C10A 175.6(8) . . . . ?
O6A C7A C8A C9A 6.8(5) . . . . ?
N1 S1 C13 C14 -99.17(12) . . . . ?
N1 S1 C13 C18 78.58(13) . . . . ?
N1 C2 C3 C4 172(2) . . . . ?
N1 C2 C3 C11 -9(3) . . . . ?
N1 C2A C3A C4A -170.4(18) . . . . ?
N1 C2A C3A C11A 6(2) . . . . ?
C13 S1 N1 C2 -69.2(6) . . . . ?
C13 S1 N1 C12 72.3(7) . . . . ?
C13 S1 N1 C2A 75.4(7) . . . . ?
C13 S1 N1 C12A -72.5(7) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C14 C13 C18 C17 0.7(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C14 C15 C16 C19 -179.40(14) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C13 -1.4(2) . . . . ?
C18 C13 C14 C15 0.6(2) . . . . ?
C19 C16 C17 C18 -179.22(14) . . . . ?
C2 N1 C12 C11 -13.7(13) . . . . ?
C2 C3 C4 C5 177(2) . . . . ?
C2 C3 C11 C10 -174.3(17) . . . . ?
C2 C3 C11 C12 1(3) . . . . ?
C3 C4 C5 O6 179.8(16) . . . . ?
C3 C4 C5 C9 -2.7(19) . . . . ?
C3 C11 C12 N1 9(2) . . . . ?
C4 C3 C11 C10 5(4) . . . . ?
C4 C3 C11 C12 180(2) . . . . ?
C4 C5 C9 C8 -178.4(8) . . . . ?
C4 C5 C9 C10 3.7(12) . . . . ?
C5 O6 C7 C8 3.2(6) . . . . ?
C5 C9 C10 C11 -0.2(15) . . . . ?
C7 O6 C5 C4 176.2(8) . . . . ?
C7 O6 C5 C9 -1.6(8) . . . . ?
C7 C8 C9 C5 2.5(6) . . . . ?
C7 C8 C9 C10 180.0(8) . . . . ?
C8 C9 C10 C11 -177.5(10) . . . . ?
C9 C10 C11 C3 -4(2) . . . . ?
C9 C10 C11 C12 -177.2(15) . . . . ?
C10 C11 C12 N1 -177.5(16) . . . . ?
C11 C3 C4 C5 -2(4) . . . . ?
C12 N1 C2 C3 14.2(17) . . . . ?
C2A N1 C12A C11A 11.0(19) . . . . ?
C2A C3A C4A C5A -179.6(17) . . . . ?
C2A C3A C11A C10A 178(2) . . . . ?
C2A C3A C11A C12A 0(4) . . . . ?
C3A C4A C5A O6A -178.7(13) . . . . ?
C3A C4A C5A C9A -0.3(19) . . . . ?
C3A C11A C12A N1 -7(3) . . . . ?
C4A C3A C11A C10A -6(4) . . . . ?
C4A C3A C11A C12A 176(2) . . . . ?
C4A C5A C9A C8A -178.3(10) . . . . ?
C4A C5A C9A C10A -2.9(14) . . . . ?
C5A O6A C7A C8A -7.0(6) . . . . ?
C5A C9A C10A C11A 2(2) . . . . ?
C7A O6A C5A C4A -177.2(9) . . . . ?
C7A O6A C5A C9A 4.3(8) . . . . ?
C7A C8A C9A C5A -4.3(7) . . . . ?
C7A C8A C9A C10A -178.8(10) . . . . ?
C8A C9A C10A C11A 176(2) . . . . ?
C9A C10A C11A C3A 2(4) . . . . ?
C9A C10A C11A C12A 179(3) . . . . ?
C10A C11A C12A N1 176(3) . . . . ?
C11A C3A C4A C5A 5(3) . . . . ?
C12A N1 C2A C3A -11.1(15) . . . . ?


#==END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/diethyl ether'
####################################################################### 
# 
# 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_25
_database_code_depnum_ccdc_archive 'CCDC 2181493'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-06-23 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_audit_creation_date             2022-06-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 B N O5, C3 H6 O'
_chemical_formula_sum            'C17 H22 B N O6'
_chemical_formula_weight         347.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1060(4)
_cell_length_b                   9.9589(3)
_cell_length_c                   13.1775(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.771(4)
_cell_angle_gamma                90
_cell_volume                     1719.14(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4252
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.5240
_cell_measurement_theta_min      2.5670
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11853
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.118
_diffrn_reflns_theta_min         2.564
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00  63.00   0.50   80.00    --  -12.80  21.00  90.00  292
  2  ω    -97.00 -71.00   0.50   80.00    --  -12.80  42.00  60.00   52
  3  ω    -16.00  65.00   0.50   80.00    --  -12.80  42.00  60.00  162
  4  ω   -101.00 -14.00   0.50   80.00    --  -12.80  31.00  30.00  174
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0313842000
_diffrn_orient_matrix_UB_12      0.0467162000
_diffrn_orient_matrix_UB_13      -0.0269450000
_diffrn_orient_matrix_UB_21      -0.0017213000
_diffrn_orient_matrix_UB_22      -0.0434268000
_diffrn_orient_matrix_UB_23      -0.0426713000
_diffrn_orient_matrix_UB_31      -0.0440728000
_diffrn_orient_matrix_UB_32      -0.0317109000
_diffrn_orient_matrix_UB_33      0.0188129000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3057
_reflns_number_total             3951
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011  (Burla et al.,  2007)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3951
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.4839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C11(H11A,H11B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O -0.16115(8) -0.02436(11) 0.68289(9) 0.0433(3) Uani 1 1 d . . . . .
O12 O 0.43083(8) -0.07993(12) 1.08867(8) 0.0400(3) Uani 1 1 d . . . . .
O13 O 0.31643(7) 0.00043(9) 0.97505(7) 0.0286(2) Uani 1 1 d . . . . .
O15 O 0.43114(8) 0.15458(10) 0.70214(8) 0.0357(3) Uani 1 1 d . . . . .
O16 O 0.30844(7) 0.09275(9) 0.80674(8) 0.0286(2) Uani 1 1 d . . . . .
O21 O 0.30686(9) -0.04363(10) 0.53605(8) 0.0361(3) Uani 1 1 d . . . . .
N1 N 0.35400(8) -0.14344(10) 0.83132(8) 0.0203(2) Uani 1 1 d . . . . .
C1 C 0.15733(9) -0.05088(13) 0.85682(10) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.09668(10) -0.11915(13) 0.92752(10) 0.0242(3) Uani 1 1 d . . . . .
C3 C -0.00767(10) -0.13819(14) 0.90616(11) 0.0279(3) Uani 1 1 d . . . . .
H3 H -0.048570 -0.181860 0.954454 0.033 Uiso 1 1 calc R U . . .
C4 C -0.05171(10) -0.09412(13) 0.81557(11) 0.0277(3) Uani 1 1 d . . . . .
C5 C -0.15949(11) -0.10508(16) 0.77366(12) 0.0359(4) Uani 1 1 d . . . . .
H5A H -0.176902 -0.199597 0.757570 0.043 Uiso 1 1 calc R U . . .
H5B H -0.208528 -0.070260 0.822902 0.043 Uiso 1 1 calc R U . . .
C7 C -0.05936(12) 0.00592(19) 0.65399(15) 0.0471(4) Uani 1 1 d . . . . .
H7A H -0.052601 0.102275 0.637001 0.057 Uiso 1 1 calc R U . . .
H7B H -0.040367 -0.048318 0.594508 0.057 Uiso 1 1 calc R U . . .
C8 C 0.00657(11) -0.02943(14) 0.74553(12) 0.0309(3) Uani 1 1 d . . . . .
C9 C 0.10978(11) -0.00724(14) 0.76593(12) 0.0313(3) Uani 1 1 d . . . . .
H9 H 0.148987 0.038467 0.717287 0.038 Uiso 1 1 calc R U . . .
C10 C 0.13978(11) -0.17664(16) 1.02622(11) 0.0333(3) Uani 1 1 d . . . . .
H10A H 0.186793 -0.250156 1.011572 0.050 Uiso 1 1 calc R U . . .
H10B H 0.083897 -0.210737 1.066703 0.050 Uiso 1 1 calc R U . . .
H10C H 0.176537 -0.106217 1.064277 0.050 Uiso 1 1 calc R U . . .
C11 C 0.40904(11) -0.18751(14) 0.92651(10) 0.0283(3) Uani 1 1 d . . . . .
H11A H 0.483210 -0.194574 0.915385 0.034 Uiso 1 1 calc R U . . .
H11B H 0.383735 -0.276337 0.948196 0.034 Uiso 1 1 calc R U . . .
C12 C 0.38890(10) -0.08390(14) 1.00558(10) 0.0255(3) Uani 1 1 d . . . . .
C14 C 0.42356(10) -0.07411(14) 0.75989(10) 0.0258(3) Uani 1 1 d . . . . .
H14A H 0.418931 -0.117046 0.692148 0.031 Uiso 1 1 calc R U . . .
H14B H 0.495144 -0.079727 0.785794 0.031 Uiso 1 1 calc R U . . .
C15 C 0.39027(10) 0.07028(13) 0.75262(10) 0.0254(3) Uani 1 1 d . . . . .
C17 C 0.30161(12) -0.25839(15) 0.77911(13) 0.0373(4) Uani 1 1 d . . . . .
H17A H 0.263071 -0.225505 0.719226 0.056 Uiso 1 1 calc R U . . .
H17B H 0.254759 -0.301255 0.825756 0.056 Uiso 1 1 calc R U . . .
H17C H 0.352580 -0.323899 0.758055 0.056 Uiso 1 1 calc R U . . .
C21 C 0.31189(11) 0.06558(14) 0.49510(10) 0.0269(3) Uani 1 1 d . . . . .
C22 C 0.39053(11) 0.09537(16) 0.41843(12) 0.0340(3) Uani 1 1 d . . . . .
H22A H 0.438670 0.020269 0.415491 0.051 Uiso 1 1 calc R U . . .
H22B H 0.427466 0.177415 0.437946 0.051 Uiso 1 1 calc R U . . .
H22C H 0.357010 0.107948 0.351597 0.051 Uiso 1 1 calc R U . . .
C23 C 0.24104(12) 0.17711(16) 0.51994(12) 0.0376(4) Uani 1 1 d . . . . .
H23A H 0.184781 0.141847 0.559348 0.056 Uiso 1 1 calc R U . . .
H23B H 0.213633 0.217365 0.456945 0.056 Uiso 1 1 calc R U . . .
H23C H 0.278136 0.245449 0.559856 0.056 Uiso 1 1 calc R U . . .
B1 B 0.27695(11) -0.02117(14) 0.87005(12) 0.0226(3) 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
O6 C5 1.4408(19) . ?
O6 C7 1.4308(19) . ?
O12 C12 1.2105(16) . ?
O13 C12 1.3213(17) . ?
O13 B1 1.4779(17) . ?
O15 C15 1.2068(16) . ?
O16 C15 1.3251(17) . ?
O16 B1 1.4747(17) . ?
O21 C21 1.2168(17) . ?
N1 C11 1.4935(17) . ?
N1 C14 1.4990(16) . ?
N1 C17 1.4920(17) . ?
N1 B1 1.6718(18) . ?
C1 C2 1.4169(18) . ?
C1 C9 1.4020(19) . ?
C1 B1 1.5996(19) . ?
C2 C3 1.4007(19) . ?
C2 C10 1.5144(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(2) . ?
C4 C5 1.5046(19) . ?
C4 C8 1.376(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.504(2) . ?
C8 C9 1.389(2) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.496(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5049(19) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 C22 1.495(2) . ?
C21 C23 1.491(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 O6 C5 110.38(11) . . ?
C12 O13 B1 114.84(10) . . ?
C15 O16 B1 114.83(10) . . ?
C11 N1 C14 112.05(10) . . ?
C11 N1 B1 103.79(10) . . ?
C14 N1 B1 103.94(9) . . ?
C17 N1 C11 111.43(11) . . ?
C17 N1 C14 110.12(11) . . ?
C17 N1 B1 115.21(10) . . ?
C2 C1 B1 125.80(12) . . ?
C9 C1 C2 117.83(12) . . ?
C9 C1 B1 116.36(12) . . ?
C1 C2 C10 122.97(12) . . ?
C3 C2 C1 119.80(12) . . ?
C3 C2 C10 117.22(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.66(13) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 131.04(13) . . ?
C8 C4 C3 120.17(12) . . ?
C8 C4 C5 108.79(13) . . ?
O6 C5 C4 104.72(12) . . ?
O6 C5 H5A 110.8 . . ?
O6 C5 H5B 110.8 . . ?
C4 C5 H5A 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
O6 C7 H7A 110.8 . . ?
O6 C7 H7B 110.8 . . ?
O6 C7 C8 104.75(13) . . ?
H7A C7 H7B 108.9 . . ?
C8 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C4 C8 C7 109.30(13) . . ?
C4 C8 C9 120.14(14) . . ?
C9 C8 C7 130.56(14) . . ?
C1 C9 H9 119.3 . . ?
C8 C9 C1 121.38(13) . . ?
C8 C9 H9 119.3 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 110.3 . . ?
N1 C11 H11B 110.3 . . ?
N1 C11 C12 106.93(11) . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
O12 C12 O13 123.83(13) . . ?
O12 C12 C11 124.59(13) . . ?
O13 C12 C11 111.54(11) . . ?
N1 C14 H14A 110.2 . . ?
N1 C14 H14B 110.2 . . ?
N1 C14 C15 107.42(10) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
O15 C15 O16 124.03(13) . . ?
O15 C15 C14 124.54(13) . . ?
O16 C15 C14 111.40(11) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O21 C21 C22 121.66(13) . . ?
O21 C21 C23 121.74(13) . . ?
C23 C21 C22 116.59(12) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O13 B1 N1 101.22(10) . . ?
O13 B1 C1 116.27(11) . . ?
O16 B1 O13 108.76(10) . . ?
O16 B1 N1 101.85(10) . . ?
O16 B1 C1 111.79(11) . . ?
C1 B1 N1 115.54(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C7 C8 C4 8.50(18) . . . . ?
O6 C7 C8 C9 -171.78(16) . . . . ?
N1 C11 C12 O12 -171.44(12) . . . . ?
N1 C11 C12 O13 11.00(15) . . . . ?
N1 C14 C15 O15 179.06(12) . . . . ?
N1 C14 C15 O16 -2.58(15) . . . . ?
C1 C2 C3 C4 1.7(2) . . . . ?
C2 C1 C9 C8 0.2(2) . . . . ?
C2 C1 B1 O13 -31.93(18) . . . . ?
C2 C1 B1 O16 -157.63(12) . . . . ?
C2 C1 B1 N1 86.51(16) . . . . ?
C2 C3 C4 C5 178.24(14) . . . . ?
C2 C3 C4 C8 -0.7(2) . . . . ?
C3 C4 C5 O6 172.36(14) . . . . ?
C3 C4 C8 C7 179.26(14) . . . . ?
C3 C4 C8 C9 -0.5(2) . . . . ?
C4 C8 C9 C1 0.7(2) . . . . ?
C5 O6 C7 C8 -14.21(18) . . . . ?
C5 C4 C8 C7 0.10(18) . . . . ?
C5 C4 C8 C9 -179.66(14) . . . . ?
C7 O6 C5 C4 14.28(17) . . . . ?
C7 C8 C9 C1 -178.97(16) . . . . ?
C8 C4 C5 O6 -8.59(16) . . . . ?
C9 C1 C2 C3 -1.41(19) . . . . ?
C9 C1 C2 C10 177.22(13) . . . . ?
C9 C1 B1 O13 149.41(12) . . . . ?
C9 C1 B1 O16 23.71(17) . . . . ?
C9 C1 B1 N1 -92.15(14) . . . . ?
C10 C2 C3 C4 -177.03(13) . . . . ?
C11 N1 C14 C15 -113.56(12) . . . . ?
C11 N1 B1 O13 10.74(12) . . . . ?
C11 N1 B1 O16 122.87(10) . . . . ?
C11 N1 B1 C1 -115.76(12) . . . . ?
C12 O13 B1 O16 -111.51(12) . . . . ?
C12 O13 B1 N1 -4.74(13) . . . . ?
C12 O13 B1 C1 121.28(12) . . . . ?
C14 N1 C11 C12 98.70(12) . . . . ?
C14 N1 B1 O13 -106.59(11) . . . . ?
C14 N1 B1 O16 5.54(12) . . . . ?
C14 N1 B1 C1 126.91(12) . . . . ?
C15 O16 B1 O13 98.54(12) . . . . ?
C15 O16 B1 N1 -7.79(14) . . . . ?
C15 O16 B1 C1 -131.73(12) . . . . ?
C17 N1 C11 C12 -137.40(11) . . . . ?
C17 N1 C14 C15 121.82(12) . . . . ?
C17 N1 B1 O13 132.84(11) . . . . ?
C17 N1 B1 O16 -115.04(12) . . . . ?
C17 N1 B1 C1 6.34(16) . . . . ?
B1 O13 C12 O12 179.03(12) . . . . ?
B1 O13 C12 C11 -3.39(15) . . . . ?
B1 O16 C15 O15 -174.61(12) . . . . ?
B1 O16 C15 C14 7.01(15) . . . . ?
B1 N1 C11 C12 -12.83(13) . . . . ?
B1 N1 C14 C15 -2.12(13) . . . . ?
B1 C1 C2 C3 179.95(12) . . . . ?
B1 C1 C2 C10 -1.4(2) . . . . ?
B1 C1 C9 C8 179.00(13) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone/diethyl ether'
