# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_170622_lxw_1
_database_code_depnum_ccdc_archive 'CCDC 1854824'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;
_audit_creation_date             2017-06-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H17 B9 N O, C4 H10 N0.5, C4 N0.5'
_chemical_formula_sum            'C13 H27 B9 N2 O'
_chemical_formula_weight         324.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 b1'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   31.845(4)
_cell_length_b                   10.2834(6)
_cell_length_c                   15.723(2)
_cell_angle_alpha                90
_cell_angle_beta                 118.864(19)
_cell_angle_gamma                90
_cell_volume                     4509.1(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2817
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3648
_cell_measurement_theta_min      2.7843
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.053
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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    0.956
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13933
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.790
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00    6.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -38.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -63.00   22.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00   62.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   46.0000  135.0000 99
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0177359000
_diffrn_orient_matrix_UB_12      -0.0300390000
_diffrn_orient_matrix_UB_13      -0.0430021000
_diffrn_orient_matrix_UB_21      -0.0125291000
_diffrn_orient_matrix_UB_22      -0.0195863000
_diffrn_orient_matrix_UB_23      0.0248384000
_diffrn_orient_matrix_UB_31      -0.0132489000
_diffrn_orient_matrix_UB_32      0.0589199000
_diffrn_orient_matrix_UB_33      -0.0136753000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2517
_reflns_number_total             4123
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0823
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1721P)²+0.5426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2421
_refine_ls_wR_factor_ref         0.2862
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 B9-H9
 1.1 with sigma of 0.02
3. Others
 Fixed Sof: C10(0.5) C11(0.5) C12(0.5) C14(0.5)
4.a Ternary CH refined with riding coordinates:
 C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
4.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C0AA(H0AA,H0AB,H0AC), C7(H7A,H7B,H7C)
4.e Boron cage BH refined with riding coordinates:
 B1(H1A), B2(H2), B3(H3A), B4(H4), B5(H5), B6(H6), B7(H7), B8(H8)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.11474(9) 0.64852(17) 0.24840(17) 0.0902(7) Uani 1 1 d . . . . .
N1 N 0.13216(13) 0.6277(2) 0.1296(2) 0.1017(10) Uani 1 1 d . . . . .
H1 H 0.138407 0.573507 0.095512 0.122 Uiso 1 1 calc R . . . .
C1 C 0.12825(8) 0.4361(2) 0.21074(17) 0.0571(6) Uani 1 1 d . . . . .
C2 C 0.12409(8) 0.5794(2) 0.19725(18) 0.0584(6) Uani 1 1 d . . . . .
C3 C 0.13147(16) 0.7657(3) 0.1068(3) 0.0995(12) Uani 1 1 d . . . . .
H3 H 0.126167 0.814463 0.154315 0.119 Uiso 1 1 calc R . . . .
C4 C 0.17818(19) 0.8074(4) 0.1178(4) 0.1443(19) Uani 1 1 d . . . . .
H4A H 0.203143 0.785747 0.181755 0.216 Uiso 1 1 calc GR . . . .
H4B H 0.177827 0.899648 0.108264 0.216 Uiso 1 1 calc GR . . . .
H4C H 0.183947 0.763755 0.070383 0.216 Uiso 1 1 calc GR . . . .
C5 C 0.0906(2) 0.7940(4) 0.0095(4) 0.156(2) Uani 1 1 d . . . . .
H5A H 0.093622 0.743375 -0.038552 0.234 Uiso 1 1 calc GR . . . .
H5B H 0.090505 0.884780 -0.004755 0.234 Uiso 1 1 calc GR . . . .
H5C H 0.061093 0.772087 0.008762 0.234 Uiso 1 1 calc GR . . . .
B1 B 0.12676(13) 0.3617(3) 0.2987(2) 0.0711(9) Uani 1 1 d . . . . .
H1A H 0.121726 0.414114 0.354132 0.085 Uiso 1 1 calc R . . . .
B2 B 0.17762(11) 0.3589(3) 0.2735(2) 0.0653(8) Uani 1 1 d . . . . .
H2 H 0.212425 0.409180 0.309144 0.078 Uiso 1 1 calc R . . . .
B3 B 0.13583(11) 0.3288(3) 0.1448(2) 0.0605(7) Uani 1 1 d . . . . .
H3A H 0.137844 0.355936 0.079151 0.073 Uiso 1 1 calc R . . . .
B4 B 0.08521(12) 0.3326(3) 0.1703(3) 0.0694(8) Uani 1 1 d . . . . .
H4 H 0.047612 0.361953 0.124741 0.083 Uiso 1 1 calc R . . . .
B5 B 0.10095(15) 0.2043(3) 0.2581(3) 0.0832(10) Uani 1 1 d . . . . .
H5 H 0.074264 0.167426 0.277517 0.100 Uiso 1 1 calc R . . . .
B6 B 0.16596(15) 0.2227(3) 0.3306(3) 0.0825(10) Uani 1 1 d . . . . .
H6 H 0.190810 0.200522 0.407304 0.099 Uiso 1 1 calc R . . . .
B7 B 0.17182(13) 0.1990(3) 0.2210(2) 0.0701(9) Uani 1 1 d . . . . .
H7 H 0.201156 0.158059 0.211332 0.084 Uiso 1 1 calc R . . . .
B8 B 0.10754(13) 0.1812(3) 0.1492(3) 0.0728(9) Uani 1 1 d . . . . .
H8 H 0.085912 0.126118 0.081986 0.087 Uiso 1 1 calc R . . . .
B9 B 0.13944(15) 0.0976(3) 0.2520(3) 0.0851(11) Uani 1 1 d D . . . .
H9 H 0.1420(11) -0.0111(18) 0.262(2) 0.094(9) Uiso 1 1 d D . . . .
N2 N 0.000000 0.7803(3) 0.250000 0.0661(8) Uani 1 2 d S T P . .
C0AA C 0.00259(14) 0.9526(4) 0.1358(3) 0.1194(14) Uani 1 1 d . . . . .
H0AA H -0.014743 0.901944 0.077801 0.179 Uiso 1 1 calc GR . . . .
H0AB H 0.024480 1.009535 0.128372 0.179 Uiso 1 1 calc GR . . . .
H0AC H -0.019562 1.003208 0.147130 0.179 Uiso 1 1 calc GR . . . .
C6 C 0.03500(10) 0.6967(3) 0.3340(2) 0.0797(8) Uani 1 1 d . . . . .
H6A H 0.054917 0.649682 0.313297 0.096 Uiso 1 1 calc R . . . .
H6B H 0.055861 0.753627 0.386797 0.096 Uiso 1 1 calc R . . . .
C7 C 0.01296(15) 0.6004(4) 0.3723(3) 0.1173(13) Uani 1 1 d . . . . .
H7A H -0.008164 0.543865 0.320750 0.176 Uiso 1 1 calc GR . . . .
H7B H -0.004859 0.645784 0.397900 0.176 Uiso 1 1 calc GR . . . .
H7C H 0.037794 0.549800 0.422966 0.176 Uiso 1 1 calc GR . . . .
C8 C 0.03011(10) 0.8634(3) 0.2205(2) 0.0790(8) Uani 1 1 d . . . . .
H8A H 0.051658 0.915643 0.275923 0.095 Uiso 1 1 calc R . . . .
H8B H 0.049686 0.806403 0.204869 0.095 Uiso 1 1 calc R . . . .
N3 N 0.250000 0.750000 0.500000 0.0561(7) Uani 1 2 d S T P . .
C10 C 0.2258(2) 0.6157(5) 0.4638(5) 0.0816(17) Uani 0.5 1 d . . . . .
C11 C 0.2777(2) 0.6743(6) 0.4577(4) 0.0755(15) Uani 0.5 1 d . . . . .
C12 C 0.19949(19) 0.7616(6) 0.4221(4) 0.0779(15) Uani 0.5 1 d . . . . .
C13 C 0.16826(12) 0.8465(4) 0.4610(3) 0.1021(12) Uani 1 1 d . . . . .
C14 C 0.2435(2) 0.8183(6) 0.4078(5) 0.0861(18) Uani 0.5 1 d . . . . .
C15 C 0.26899(17) 0.9636(4) 0.4418(4) 0.1402(18) 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
O1 C2 1.213(3) . ?
N1 H1 0.8600 . ?
N1 C2 1.307(3) . ?
N1 C3 1.462(4) . ?
C1 C2 1.486(3) . ?
C1 B1 1.602(4) . ?
C1 B2 1.605(4) . ?
C1 B3 1.610(4) . ?
C1 B4 1.605(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.476(6) . ?
C3 C5 1.482(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
B1 H1A 1.1000 . ?
B1 B2 1.844(5) . ?
B1 B4 1.827(5) . ?
B1 B5 1.788(4) . ?
B1 B6 1.803(5) . ?
B2 H2 1.1000 . ?
B2 B3 1.834(4) . ?
B2 B6 1.797(5) . ?
B2 B7 1.810(4) . ?
B3 H3A 1.1000 . ?
B3 B4 1.840(4) . ?
B3 B7 1.791(4) . ?
B3 B8 1.784(4) . ?
B4 H4 1.1000 . ?
B4 B5 1.797(5) . ?
B4 B8 1.807(4) . ?
B5 H5 1.1000 . ?
B5 B6 1.828(6) . ?
B5 B8 1.837(5) . ?
B5 B9 1.682(5) . ?
B6 H6 1.1000 . ?
B6 B7 1.837(5) . ?
B6 B9 1.700(5) . ?
B7 H7 1.1000 . ?
B7 B8 1.807(5) . ?
B7 B9 1.695(5) . ?
B8 H8 1.1000 . ?
B8 B9 1.672(5) . ?
B9 H9 1.126(17) . ?
N2 C6 1.518(3) 2 ?
N2 C6 1.518(3) . ?
N2 C8 1.515(3) 2 ?
N2 C8 1.515(3) . ?
C0AA H0AA 0.9600 . ?
C0AA H0AB 0.9600 . ?
C0AA H0AC 0.9600 . ?
C0AA C8 1.502(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.499(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N3 C10 1.550(5) . ?
N3 C10 1.550(5) 7_566 ?
N3 C11 1.547(5) 7_566 ?
N3 C11 1.547(5) . ?
N3 C12 1.483(5) . ?
N3 C12 1.483(5) 7_566 ?
N3 C14 1.532(5) 7_566 ?
N3 C14 1.532(5) . ?
C10 C11 1.806(9) . ?
C10 C12 1.689(9) . ?
C10 C14 1.894(9) 7_566 ?
C10 C15 1.630(8) 7_566 ?
C11 C12 1.791(8) 7_566 ?
C11 C13 1.587(7) 7_566 ?
C11 C14 1.781(8) . ?
C12 C13 1.647(7) . ?
C12 C14 1.629(8) . ?
C14 C15 1.661(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 117.2 . . ?
C2 N1 C3 125.6(2) . . ?
C3 N1 H1 117.2 . . ?
C2 C1 B1 124.0(2) . . ?
C2 C1 B2 124.9(2) . . ?
C2 C1 B3 128.2(2) . . ?
C2 C1 B4 127.0(2) . . ?
B1 C1 B2 70.2(2) . . ?
B1 C1 B3 107.8(2) . . ?
B1 C1 B4 69.5(2) . . ?
B2 C1 B3 69.55(18) . . ?
B4 C1 B2 108.1(2) . . ?
B4 C1 B3 69.81(18) . . ?
O1 C2 N1 121.7(2) . . ?
O1 C2 C1 121.3(2) . . ?
N1 C2 C1 117.0(2) . . ?
N1 C3 H3 107.3 . . ?
N1 C3 C4 111.0(3) . . ?
N1 C3 C5 110.2(4) . . ?
C4 C3 H3 107.3 . . ?
C4 C3 C5 113.4(4) . . ?
C5 C3 H3 107.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 B1 H1A 121.8 . . ?
C1 B1 B2 55.01(16) . . ?
C1 B1 B4 55.33(17) . . ?
C1 B1 B5 108.9(2) . . ?
C1 B1 B6 108.3(2) . . ?
B2 B1 H1A 131.0 . . ?
B4 B1 H1A 130.6 . . ?
B4 B1 B2 90.1(2) . . ?
B5 B1 H1A 120.6 . . ?
B5 B1 B2 102.1(2) . . ?
B5 B1 B4 59.60(19) . . ?
B5 B1 B6 61.2(2) . . ?
B6 B1 H1A 120.9 . . ?
B6 B1 B2 59.04(18) . . ?
B6 B1 B4 102.3(2) . . ?
C1 B2 B1 54.81(16) . . ?
C1 B2 H2 121.9 . . ?
C1 B2 B3 55.35(15) . . ?
C1 B2 B6 108.4(2) . . ?
C1 B2 B7 108.4(2) . . ?
B1 B2 H2 131.1 . . ?
B3 B2 B1 89.73(19) . . ?
B3 B2 H2 131.1 . . ?
B6 B2 B1 59.34(18) . . ?
B6 B2 H2 120.8 . . ?
B6 B2 B3 101.8(2) . . ?
B6 B2 B7 61.25(18) . . ?
B7 B2 B1 101.9(2) . . ?
B7 B2 H2 121.0 . . ?
B7 B2 B3 58.88(17) . . ?
C1 B3 B2 55.10(15) . . ?
C1 B3 H3A 121.7 . . ?
C1 B3 B4 54.95(15) . . ?
C1 B3 B7 109.0(2) . . ?
C1 B3 B8 108.8(2) . . ?
B2 B3 H3A 130.8 . . ?
B2 B3 B4 90.1(2) . . ?
B4 B3 H3A 130.8 . . ?
B7 B3 B2 59.88(16) . . ?
B7 B3 H3A 120.6 . . ?
B7 B3 B4 102.4(2) . . ?
B8 B3 B2 102.2(2) . . ?
B8 B3 H3A 120.8 . . ?
B8 B3 B4 59.80(17) . . ?
B8 B3 B7 60.73(19) . . ?
C1 B4 B1 55.17(17) . . ?
C1 B4 B3 55.23(15) . . ?
C1 B4 H4 121.9 . . ?
C1 B4 B5 108.3(2) . . ?
C1 B4 B8 107.9(2) . . ?
B1 B4 B3 90.1(2) . . ?
B1 B4 H4 130.9 . . ?
B3 B4 H4 131.1 . . ?
B5 B4 B1 59.11(18) . . ?
B5 B4 B3 101.7(2) . . ?
B5 B4 H4 120.9 . . ?
B5 B4 B8 61.30(19) . . ?
B8 B4 B1 101.8(2) . . ?
B8 B4 B3 58.57(17) . . ?
B8 B4 H4 121.2 . . ?
B1 B5 B4 61.29(18) . . ?
B1 B5 H5 119.7 . . ?
B1 B5 B6 59.78(19) . . ?
B1 B5 B8 102.1(2) . . ?
B4 B5 H5 120.0 . . ?
B4 B5 B6 102.4(2) . . ?
B4 B5 B8 59.61(18) . . ?
B6 B5 H5 131.0 . . ?
B6 B5 B8 89.5(2) . . ?
B8 B5 H5 131.7 . . ?
B9 B5 B1 112.9(3) . . ?
B9 B5 B4 112.1(2) . . ?
B9 B5 H5 118.2 . . ?
B9 B5 B6 57.7(2) . . ?
B9 B5 B8 56.5(2) . . ?
B1 B6 B5 59.00(19) . . ?
B1 B6 H6 120.3 . . ?
B1 B6 B7 102.4(2) . . ?
B2 B6 B1 61.62(18) . . ?
B2 B6 B5 102.3(2) . . ?
B2 B6 H6 119.8 . . ?
B2 B6 B7 59.72(17) . . ?
B5 B6 H6 131.4 . . ?
B5 B6 B7 89.9(2) . . ?
B7 B6 H6 131.0 . . ?
B9 B6 B1 111.3(3) . . ?
B9 B6 B2 112.1(2) . . ?
B9 B6 B5 56.8(2) . . ?
B9 B6 H6 118.9 . . ?
B9 B6 B7 57.09(19) . . ?
B2 B7 B6 59.03(18) . . ?
B2 B7 H7 120.3 . . ?
B3 B7 B2 61.24(17) . . ?
B3 B7 B6 101.9(2) . . ?
B3 B7 H7 120.3 . . ?
B3 B7 B8 59.44(17) . . ?
B6 B7 H7 131.2 . . ?
B8 B7 B2 102.2(2) . . ?
B8 B7 B6 90.1(2) . . ?
B8 B7 H7 131.0 . . ?
B9 B7 B2 111.7(2) . . ?
B9 B7 B3 111.7(3) . . ?
B9 B7 B6 57.4(2) . . ?
B9 B7 H7 118.7 . . ?
B9 B7 B8 56.9(2) . . ?
B3 B8 B4 61.63(16) . . ?
B3 B8 B5 102.3(2) . . ?
B3 B8 B7 59.83(17) . . ?
B3 B8 H8 119.6 . . ?
B4 B8 B5 59.09(18) . . ?
B4 B8 B7 103.1(2) . . ?
B4 B8 H8 120.0 . . ?
B5 B8 H8 131.4 . . ?
B7 B8 B5 90.5(2) . . ?
B7 B8 H8 130.3 . . ?
B9 B8 B3 113.1(3) . . ?
B9 B8 B4 112.0(2) . . ?
B9 B8 B5 57.0(2) . . ?
B9 B8 B7 58.1(2) . . ?
B9 B8 H8 118.1 . . ?
B5 B9 B6 65.5(2) . . ?
B5 B9 B7 100.2(2) . . ?
B5 B9 H9 130.0(16) . . ?
B6 B9 H9 132.1(16) . . ?
B7 B9 B6 65.5(2) . . ?
B7 B9 H9 129.8(16) . . ?
B8 B9 B5 66.4(2) . . ?
B8 B9 B6 99.8(2) . . ?
B8 B9 B7 64.9(2) . . ?
B8 B9 H9 128.0(16) . . ?
C6 N2 C6 111.0(3) . 2 ?
C8 N2 C6 111.16(18) 2 . ?
C8 N2 C6 106.16(16) 2 2 ?
C8 N2 C6 106.16(16) . . ?
C8 N2 C6 111.16(18) . 2 ?
C8 N2 C8 111.3(3) . 2 ?
H0AA C0AA H0AB 109.5 . . ?
H0AA C0AA H0AC 109.5 . . ?
H0AB C0AA H0AC 109.5 . . ?
C8 C0AA H0AA 109.5 . . ?
C8 C0AA H0AB 109.5 . . ?
C8 C0AA H0AC 109.5 . . ?
N2 C6 H6A 108.3 . . ?
N2 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 N2 115.7(2) . . ?
C7 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 108.4 . . ?
N2 C8 H8B 108.4 . . ?
C0AA C8 N2 115.5(2) . . ?
C0AA C8 H8A 108.4 . . ?
C0AA C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C10 N3 C10 180.0 . 7_566 ?
C11 N3 C10 71.3(3) . . ?
C11 N3 C10 108.7(3) 7_566 . ?
C11 N3 C10 71.3(3) 7_566 7_566 ?
C11 N3 C10 108.7(3) . 7_566 ?
C11 N3 C11 180.0(3) 7_566 . ?
C12 N3 C10 67.6(3) 7_566 7_566 ?
C12 N3 C10 67.6(3) . . ?
C12 N3 C10 112.4(3) . 7_566 ?
C12 N3 C10 112.4(3) 7_566 . ?
C12 N3 C11 107.6(3) . . ?
C12 N3 C11 72.4(3) 7_566 . ?
C12 N3 C11 72.4(3) . 7_566 ?
C12 N3 C11 107.6(3) 7_566 7_566 ?
C12 N3 C12 180.0 7_566 . ?
C12 N3 C14 114.6(3) 7_566 . ?
C12 N3 C14 65.4(3) . . ?
C12 N3 C14 114.6(3) . 7_566 ?
C12 N3 C14 65.4(3) 7_566 7_566 ?
C14 N3 C10 104.2(4) 7_566 7_566 ?
C14 N3 C10 75.8(4) 7_566 . ?
C14 N3 C10 104.2(4) . . ?
C14 N3 C10 75.8(4) . 7_566 ?
C14 N3 C11 109.3(3) . 7_566 ?
C14 N3 C11 70.7(3) . . ?
C14 N3 C11 70.7(3) 7_566 7_566 ?
C14 N3 C11 109.3(3) 7_566 . ?
C14 N3 C14 180.0 . 7_566 ?
N3 C10 C11 54.3(2) . . ?
N3 C10 C12 54.3(3) . . ?
N3 C10 C14 51.6(3) . 7_566 ?
N3 C10 C15 107.3(4) . 7_566 ?
C11 C10 C14 85.5(3) . 7_566 ?
C12 C10 C11 88.7(4) . . ?
C12 C10 C14 90.0(4) . 7_566 ?
C15 C10 C11 121.4(4) 7_566 . ?
C15 C10 C12 127.7(5) 7_566 . ?
C15 C10 C14 55.6(3) 7_566 7_566 ?
N3 C11 C10 54.4(3) . . ?
N3 C11 C12 52.1(2) . 7_566 ?
N3 C11 C13 110.0(4) . 7_566 ?
N3 C11 C14 54.2(3) . . ?
C12 C11 C10 89.0(4) 7_566 . ?
C13 C11 C10 125.2(4) 7_566 . ?
C13 C11 C12 58.0(3) 7_566 7_566 ?
C13 C11 C14 131.5(5) 7_566 . ?
C14 C11 C10 85.3(4) . . ?
C14 C11 C12 90.5(4) . 7_566 ?
N3 C12 C10 58.1(3) . . ?
N3 C12 C11 55.4(3) . 7_566 ?
N3 C12 C13 110.2(4) . . ?
N3 C12 C14 58.7(3) . . ?
C10 C12 C11 92.6(4) . 7_566 ?
C13 C12 C10 127.0(4) . . ?
C13 C12 C11 54.8(3) . 7_566 ?
C14 C12 C10 94.2(4) . . ?
C14 C12 C11 94.4(4) . 7_566 ?
C14 C12 C13 125.1(5) . . ?
C11 C13 C12 67.3(3) 7_566 . ?
N3 C14 C10 52.5(3) . 7_566 ?
N3 C14 C11 55.1(3) . . ?
N3 C14 C12 55.9(3) . . ?
N3 C14 C15 106.6(5) . . ?
C11 C14 C10 86.4(4) . 7_566 ?
C12 C14 C10 91.0(4) . 7_566 ?
C12 C14 C11 91.5(4) . . ?
C12 C14 C15 126.7(5) . . ?
C15 C14 C10 54.1(3) . 7_566 ?
C15 C14 C11 120.4(5) . . ?
C10 C15 C14 70.2(3) 7_566 . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_170929_lxw_0434_1_150k
_database_code_depnum_ccdc_archive 'CCDC 1854825'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;
_audit_creation_date             2017-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H38 B9 N2 Na O6'
_chemical_formula_sum            'C19 H38 B9 N2 Na O6'
_chemical_formula_weight         510.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o b na'
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'
Na Na 0.0362 0.0249 '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        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6821(10)
_cell_length_b                   16.6672(16)
_cell_length_c                   16.3779(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.407(9)
_cell_angle_gamma                90
_cell_volume                     2988.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3186
_cell_measurement_temperature    149.9
_cell_measurement_theta_max      29.3067
_cell_measurement_theta_min      2.9160
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.36
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12145
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_min         2.922
_diffrn_ambient_temperature      149.9
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00   64.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7808   75.0000   58.0000 107

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   37.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       12.0933  -38.0000  150.0000 81
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0082760000
_diffrn_orient_matrix_UB_12      -0.0350255000
_diffrn_orient_matrix_UB_13      -0.0259869000
_diffrn_orient_matrix_UB_21      0.0611526000
_diffrn_orient_matrix_UB_22      0.0029965000
_diffrn_orient_matrix_UB_23      0.0012433000
_diffrn_orient_matrix_UB_31      0.0196880000
_diffrn_orient_matrix_UB_32      -0.0240111000
_diffrn_orient_matrix_UB_33      0.0381708000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3810
_reflns_number_total             5444
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5444
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0971
_refine_ls_restrained_S_all      1.143
_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)+(0.1262P)²+4.4496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2546
_refine_ls_wR_factor_ref         0.2820
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C14-C15
 1.53 with sigma of 0.02
 C14A-C15
 1.53 with sigma of 0.02
 C14A-O5A
 1.5 with sigma of 0.02
 O5-C14
 1.5 with sigma of 0.02
 B9-H9
 1.1 with sigma of 0.02
 C15-O5
 2.5 with sigma of 0.04
 C15-O5A
 2.5 with sigma of 0.04
 C15-C14A \\sim C15-C14
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C14 \\sim C14A \\sim C15: within 3.8A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(O5A) = Uanis(O5)
4. Others
 Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(O5A)=Sof(C14A)=Sof(H14C)=Sof(H14D)=1-FVAR(1)
 Sof(O5)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B), C14A(H14C,H14D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C6(H6), C7(H7), C12(H12)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C17(H17A,H17B,H17C), C10(H10A,H10B,H10C), C4(H4A,H4B,H4C),
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C15(H15A,H15B,H15C), C15(H15D,H15E,
 H15F)
5.e Boron cage BH refined with riding coordinates:
 B4(H4), B6(H6A), B5(H5), B3(H3A), B8(H8), B7(H7A)
;
_atom_sites_solution_hydrogens   mixed
_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
Na1 Na 0.98603(13) 0.41747(8) 0.43675(8) 0.0409(4) Uani 1 1 d . . . . .
O6 O 0.9577(3) 0.44517(16) 0.56441(16) 0.0509(7) Uani 1 1 d . . . . .
O1 O 0.8487(2) 0.44167(19) 0.30520(17) 0.0574(8) Uani 1 1 d . . . . .
O3 O 0.7232(3) 0.70120(18) 0.06381(19) 0.0639(9) Uani 1 1 d . . . . .
O4 O 0.8175(3) 0.6235(2) 0.52190(19) 0.0721(10) Uani 1 1 d . . . . .
N1 N 0.7969(3) 0.4323(2) 0.1610(2) 0.0557(9) Uani 1 1 d . . . . .
H1 H 0.736877 0.430989 0.110329 0.067 Uiso 1 1 calc R . . . .
C2 C 0.7690(3) 0.4392(2) 0.2331(2) 0.0433(9) Uani 1 1 d . . . . .
C1 C 0.6372(3) 0.4462(2) 0.2205(2) 0.0430(9) Uani 1 1 d . . . . .
C11 C 0.6642(3) 0.5380(2) 0.3689(2) 0.0447(9) Uani 1 1 d . . . . .
H11 H 0.747729 0.522875 0.392227 0.054 Uiso 1 1 calc R . . . .
C6 C 0.6006(4) 0.5859(3) 0.1254(2) 0.0489(10) Uani 1 1 d . . . . .
H6 H 0.650664 0.569510 0.093475 0.059 Uiso 1 1 calc R . . . .
O2 O 0.5851(5) 0.7904(2) 0.0705(3) 0.1065(15) Uani 1 1 d . . . . .
C3 C 0.9234(4) 0.4266(3) 0.1620(3) 0.0640(13) Uani 1 1 d . . . . .
H3 H 0.976688 0.459658 0.211722 0.077 Uiso 1 1 calc R . . . .
C7 C 0.5833(4) 0.6625(3) 0.1296(3) 0.0633(12) Uani 1 1 d . . . . .
H7 H 0.537340 0.679698 0.164168 0.076 Uiso 1 1 calc R . . . .
C8 C 0.6287(5) 0.7242(3) 0.0859(3) 0.0660(13) Uani 1 1 d . . . . .
C12 C 0.6273(4) 0.5949(3) 0.4094(3) 0.0757(16) Uani 1 1 d . . . . .
H12 H 0.543910 0.610495 0.387452 0.091 Uiso 1 1 calc R . . . .
N2 N 0.9052(8) 0.3992(4) 0.6713(3) 0.139(3) Uani 1 1 d . . . . .
B1 B 0.5472(4) 0.5178(3) 0.1675(3) 0.0457(10) Uani 1 1 d . . . . .
C9 C 0.7684(6) 0.7588(3) 0.0151(3) 0.0803(17) Uani 1 1 d . . . . .
H9A H 0.794347 0.808882 0.048978 0.096 Uiso 1 1 calc R . . . .
H9B H 0.703527 0.771963 -0.040935 0.096 Uiso 1 1 calc R . . . .
B2 B 0.5814(4) 0.4933(3) 0.2852(3) 0.0448(10) Uani 1 1 d . . . . .
C5 C 0.9301(5) 0.4612(4) 0.0790(3) 0.0843(17) Uani 1 1 d . . . . .
H5A H 0.872529 0.432881 0.029021 0.126 Uiso 1 1 calc GR . . . .
H5B H 1.013141 0.455007 0.078296 0.126 Uiso 1 1 calc GR . . . .
H5C H 0.908829 0.518318 0.075455 0.126 Uiso 1 1 calc GR . . . .
C16 C 0.9659(8) 0.4044(4) 0.6296(4) 0.107(3) Uani 1 1 d . . . . .
B4 B 0.5241(4) 0.4103(3) 0.1410(3) 0.0527(12) Uani 1 1 d . . . . .
H4 H 0.538289 0.375342 0.086867 0.063 Uiso 1 1 calc R . . . .
C13 C 0.7102(5) 0.6352(4) 0.4874(3) 0.097(2) Uani 1 1 d . . . . .
C17 C 1.0846(6) 0.3474(4) 0.6715(4) 0.097(2) Uani 1 1 d . . . . .
H17A H 1.129592 0.343514 0.631158 0.145 Uiso 1 1 calc GR . . . .
H17B H 1.058186 0.293792 0.682019 0.145 Uiso 1 1 calc GR . . . .
H17C H 1.137683 0.370533 0.726779 0.145 Uiso 1 1 calc GR . . . .
B6 B 0.4348(4) 0.5344(4) 0.2200(3) 0.0590(13) Uani 1 1 d . . . . .
H6A H 0.410047 0.597045 0.232087 0.071 Uiso 1 1 calc R . . . .
B5 B 0.3953(4) 0.4750(4) 0.1183(3) 0.0655(15) Uani 1 1 d . . . . .
H5 H 0.339029 0.490602 0.049407 0.079 Uiso 1 1 calc R . . . .
B3 B 0.5616(5) 0.3853(3) 0.2575(3) 0.0558(12) Uani 1 1 d . . . . .
H3A H 0.605505 0.331197 0.296281 0.067 Uiso 1 1 calc R . . . .
C10 C 0.8738(6) 0.7209(5) -0.0007(4) 0.104(2) Uani 1 1 d . . . . .
H10A H 0.848322 0.669525 -0.030661 0.156 Uiso 1 1 calc GR . . . .
H10B H 0.939703 0.711741 0.055076 0.156 Uiso 1 1 calc GR . . . .
H10C H 0.902925 0.756414 -0.036995 0.156 Uiso 1 1 calc GR . . . .
B8 B 0.4051(5) 0.3823(4) 0.1808(4) 0.0712(16) Uani 1 1 d . . . . .
H8 H 0.357157 0.323362 0.161991 0.085 Uiso 1 1 calc R . . . .
O5 O 0.6300(6) 0.6633(4) 0.5329(4) 0.0643(14) Uani 0.480(5) 1 d D . P A 1
C4 C 0.9674(6) 0.3405(4) 0.1767(5) 0.108(2) Uani 1 1 d . . . . .
H4A H 0.960018 0.320556 0.230935 0.161 Uiso 1 1 calc GR . . . .
H4B H 1.053085 0.338016 0.180862 0.161 Uiso 1 1 calc GR . . . .
H4C H 0.917645 0.307313 0.127856 0.161 Uiso 1 1 calc GR . . . .
C18 C 0.7772(7) 0.4521(4) 0.6230(6) 0.110(2) Uani 1 1 d . . . . .
H18A H 0.778762 0.501057 0.656547 0.165 Uiso 1 1 calc GR . . . .
H18B H 0.706005 0.419701 0.620361 0.165 Uiso 1 1 calc GR . . . .
H18C H 0.771957 0.466580 0.563772 0.165 Uiso 1 1 calc GR . . . .
B9 B 0.3246(5) 0.4619(5) 0.1918(4) 0.0766(18) Uani 1 1 d D . . . .
B7 B 0.4442(5) 0.4414(4) 0.2818(4) 0.0674(15) Uani 1 1 d . . . . .
H7A H 0.426937 0.429869 0.343891 0.081 Uiso 1 1 calc R . . . .
C19 C 0.9087(11) 0.3564(4) 0.7495(5) 0.153(4) Uani 1 1 d . . . . .
H19A H 0.850980 0.311515 0.733481 0.230 Uiso 1 1 calc GR . . . .
H19B H 0.886242 0.393006 0.788237 0.230 Uiso 1 1 calc GR . . . .
H19C H 0.991406 0.335837 0.779460 0.230 Uiso 1 1 calc GR . . . .
C14 C 0.6857(10) 0.6986(8) 0.6114(7) 0.082(3) Uani 0.480(5) 1 d D U P A 1
H14A H 0.624322 0.740500 0.608404 0.098 Uiso 0.480(5) 1 calc R . P A 1
H14B H 0.670427 0.656821 0.649398 0.098 Uiso 0.480(5) 1 calc R . P A 1
C15 C 0.7681(8) 0.7275(6) 0.6595(6) 0.143(3) Uani 1 1 d D U . . .
H15A H 0.837889 0.690982 0.672785 0.214 Uiso 0.480(5) 1 calc GR . P A 1
H15B H 0.752028 0.739694 0.713040 0.214 Uiso 0.480(5) 1 calc GR . P A 1
H15C H 0.786420 0.777345 0.634696 0.214 Uiso 0.480(5) 1 calc GR . P A 1
H15D H 0.693446 0.723512 0.673718 0.214 Uiso 0.520(5) 1 calc GR . P A 2
H15E H 0.830800 0.756298 0.706129 0.214 Uiso 0.520(5) 1 calc GR . P A 2
H15F H 0.797520 0.673581 0.653503 0.214 Uiso 0.520(5) 1 calc GR . P A 2
O5A O 0.6713(5) 0.7111(4) 0.5042(4) 0.0643(14) Uani 0.520(5) 1 d D . P A 2
C14A C 0.7444(7) 0.7668(6) 0.5857(5) 0.062(2) Uani 0.520(5) 1 d D U P A 2
H14C H 0.821941 0.784759 0.579816 0.074 Uiso 0.520(5) 1 calc R . P A 2
H14D H 0.695084 0.814997 0.586120 0.074 Uiso 0.520(5) 1 calc R . P A 2
H9 H 0.232(3) 0.471(4) 0.193(4) 0.11(2) Uiso 1 1 d 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
Na1 Na1 3.390(3) 3_766 ?
Na1 O6 2.275(3) . ?
Na1 O6 2.384(3) 3_766 ?
Na1 O1 2.229(3) . ?
Na1 O4 2.260(3) 3_766 ?
Na1 O2 2.263(4) 2_645 ?
O6 C16 1.241(6) . ?
O1 C2 1.223(4) . ?
O3 C8 1.332(6) . ?
O3 C9 1.460(6) . ?
O4 C13 1.198(6) . ?
N1 H1 0.8800 . ?
N1 C2 1.336(5) . ?
N1 C3 1.475(5) . ?
C2 C1 1.486(5) . ?
C1 B1 1.628(6) . ?
C1 B2 1.626(6) . ?
C1 B4 1.613(6) . ?
C1 B3 1.595(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.312(6) . ?
C11 B2 1.564(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.298(6) . ?
C6 B1 1.566(7) . ?
O2 C8 1.204(6) . ?
C3 H3 1.0000 . ?
C3 C5 1.504(7) . ?
C3 C4 1.515(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.455(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.469(7) . ?
N2 C16 1.147(9) . ?
N2 C18 1.678(11) . ?
N2 C19 1.454(7) . ?
B1 B2 1.873(6) . ?
B1 B4 1.842(7) . ?
B1 B6 1.824(7) . ?
B1 B5 1.820(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.484(9) . ?
B2 B6 1.808(6) . ?
B2 B3 1.850(7) . ?
B2 B7 1.804(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C16 C17 1.622(10) . ?
B4 H4 1.1200 . ?
B4 B5 1.782(8) . ?
B4 B3 1.850(6) . ?
B4 B8 1.791(8) . ?
C13 O5 1.462(9) . ?
C13 O5A 1.403(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
B6 H6A 1.1200 . ?
B6 B5 1.852(7) . ?
B6 B9 1.708(8) . ?
B6 B7 1.833(9) . ?
B5 H5 1.1200 . ?
B5 B8 1.835(9) . ?
B5 B9 1.696(8) . ?
B3 H3A 1.1200 . ?
B3 B8 1.822(7) . ?
B3 B7 1.815(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
B8 H8 1.1200 . ?
B8 B9 1.672(10) . ?
B8 B7 1.841(8) . ?
O5 C14 1.356(11) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
B9 B7 1.675(9) . ?
B9 H9 1.10(2) . ?
B7 H7A 1.1200 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.119(10) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 H15D 0.9800 . ?
C15 H15E 0.9800 . ?
C15 H15F 0.9800 . ?
C15 C14A 1.316(10) . ?
O5A C14A 1.606(9) . ?
C14A H14C 0.9900 . ?
C14A H14D 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
O6 Na1 Na1 42.05(7) 3_766 3_766 ?
O6 Na1 Na1 44.57(7) . 3_766 ?
O6 Na1 O6 86.63(10) . 3_766 ?
O1 Na1 Na1 109.11(10) . 3_766 ?
O1 Na1 O6 124.43(12) . . ?
O1 Na1 O6 85.76(12) . 3_766 ?
O1 Na1 O4 131.13(12) . 3_766 ?
O1 Na1 O2 89.51(16) . 2_645 ?
O4 Na1 Na1 100.98(10) 3_766 3_766 ?
O4 Na1 O6 92.20(13) 3_766 3_766 ?
O4 Na1 O6 104.10(12) 3_766 . ?
O4 Na1 O2 92.81(17) 3_766 2_645 ?
O2 Na1 Na1 138.31(15) 2_645 3_766 ?
O2 Na1 O6 94.00(15) 2_645 . ?
O2 Na1 O6 174.64(16) 2_645 3_766 ?
Na1 O6 Na1 93.37(10) . 3_766 ?
C16 O6 Na1 133.4(4) . . ?
C16 O6 Na1 126.5(3) . 3_766 ?
C2 O1 Na1 167.5(3) . . ?
C8 O3 C9 116.8(4) . . ?
C13 O4 Na1 167.7(3) . 3_766 ?
C2 N1 H1 118.4 . . ?
C2 N1 C3 123.2(3) . . ?
C3 N1 H1 118.4 . . ?
O1 C2 N1 121.2(4) . . ?
O1 C2 C1 122.3(3) . . ?
N1 C2 C1 116.4(3) . . ?
C2 C1 B1 125.2(3) . . ?
C2 C1 B2 125.4(3) . . ?
C2 C1 B4 126.9(3) . . ?
C2 C1 B3 125.6(4) . . ?
B2 C1 B1 70.3(3) . . ?
B4 C1 B1 69.3(3) . . ?
B4 C1 B2 107.7(3) . . ?
B3 C1 B1 109.2(4) . . ?
B3 C1 B2 70.1(3) . . ?
B3 C1 B4 70.4(3) . . ?
C12 C11 H11 117.4 . . ?
C12 C11 B2 125.2(4) . . ?
B2 C11 H11 117.4 . . ?
C7 C6 H6 116.7 . . ?
C7 C6 B1 126.6(4) . . ?
B1 C6 H6 116.7 . . ?
C8 O2 Na1 171.5(4) . 2_655 ?
N1 C3 H3 108.1 . . ?
N1 C3 C5 109.4(4) . . ?
N1 C3 C4 110.2(5) . . ?
C5 C3 H3 108.1 . . ?
C5 C3 C4 112.6(5) . . ?
C4 C3 H3 108.1 . . ?
C6 C7 H7 117.3 . . ?
C6 C7 C8 125.4(4) . . ?
C8 C7 H7 117.3 . . ?
O3 C8 C7 114.1(4) . . ?
O2 C8 O3 122.5(5) . . ?
O2 C8 C7 123.4(5) . . ?
C11 C12 H12 118.7 . . ?
C11 C12 C13 122.5(4) . . ?
C13 C12 H12 118.7 . . ?
C16 N2 C18 108.3(6) . . ?
C16 N2 C19 136.7(10) . . ?
C19 N2 C18 114.9(7) . . ?
C1 B1 B2 54.8(2) . . ?
C1 B1 B4 55.0(2) . . ?
C1 B1 B6 107.2(3) . . ?
C1 B1 B5 107.3(4) . . ?
C6 B1 C1 119.0(3) . . ?
C6 B1 B2 129.6(3) . . ?
C6 B1 B4 130.5(3) . . ?
C6 B1 B6 124.1(4) . . ?
C6 B1 B5 124.5(3) . . ?
B4 B1 B2 89.5(3) . . ?
B6 B1 B2 58.5(2) . . ?
B6 B1 B4 100.8(4) . . ?
B5 B1 B2 101.2(3) . . ?
B5 B1 B4 58.2(3) . . ?
B5 B1 B6 61.1(3) . . ?
O3 C9 H9A 110.3 . . ?
O3 C9 H9B 110.3 . . ?
O3 C9 C10 107.2(5) . . ?
H9A C9 H9B 108.5 . . ?
C10 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
C1 B2 B1 54.9(2) . . ?
C1 B2 B6 108.1(3) . . ?
C1 B2 B3 54.2(3) . . ?
C1 B2 B7 107.6(3) . . ?
C11 B2 C1 122.4(3) . . ?
C11 B2 B1 130.0(4) . . ?
C11 B2 B6 120.4(4) . . ?
C11 B2 B3 131.7(3) . . ?
C11 B2 B7 121.8(3) . . ?
B6 B2 B1 59.4(2) . . ?
B6 B2 B3 102.2(3) . . ?
B3 B2 B1 89.8(3) . . ?
B7 B2 B1 101.8(3) . . ?
B7 B2 B6 61.0(3) . . ?
B7 B2 B3 59.6(3) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O6 C16 C17 118.9(6) . . ?
N2 C16 O6 132.5(9) . . ?
N2 C16 C17 108.6(7) . . ?
C1 B4 B1 55.7(2) . . ?
C1 B4 H4 121.8 . . ?
C1 B4 B5 109.8(4) . . ?
C1 B4 B3 54.4(2) . . ?
C1 B4 B8 108.9(3) . . ?
B1 B4 H4 130.0 . . ?
B1 B4 B3 90.8(3) . . ?
B5 B4 B1 60.2(3) . . ?
B5 B4 H4 119.8 . . ?
B5 B4 B3 103.3(4) . . ?
B5 B4 B8 61.8(4) . . ?
B3 B4 H4 130.7 . . ?
B8 B4 B1 103.7(4) . . ?
B8 B4 H4 120.1 . . ?
B8 B4 B3 60.0(3) . . ?
O4 C13 C12 126.8(4) . . ?
O4 C13 O5 124.2(5) . . ?
O4 C13 O5A 114.3(5) . . ?
O5 C13 C12 104.2(5) . . ?
O5A C13 C12 115.0(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
B1 B6 H6A 119.8 . . ?
B1 B6 B5 59.3(3) . . ?
B1 B6 B7 102.6(4) . . ?
B2 B6 B1 62.1(2) . . ?
B2 B6 H6A 119.9 . . ?
B2 B6 B5 102.5(3) . . ?
B2 B6 B7 59.4(3) . . ?
B5 B6 H6A 131.2 . . ?
B9 B6 B1 111.4(4) . . ?
B9 B6 B2 111.2(5) . . ?
B9 B6 H6A 119.4 . . ?
B9 B6 B5 56.7(3) . . ?
B9 B6 B7 56.3(3) . . ?
B7 B6 H6A 131.3 . . ?
B7 B6 B5 89.6(4) . . ?
B1 B5 B6 59.6(3) . . ?
B1 B5 H5 119.6 . . ?
B1 B5 B8 102.8(3) . . ?
B4 B5 B1 61.5(3) . . ?
B4 B5 B6 102.0(3) . . ?
B4 B5 H5 120.5 . . ?
B4 B5 B8 59.3(3) . . ?
B6 B5 H5 131.0 . . ?
B8 B5 B6 90.0(4) . . ?
B8 B5 H5 131.2 . . ?
B9 B5 B1 112.2(3) . . ?
B9 B5 B4 111.0(5) . . ?
B9 B5 B6 57.3(3) . . ?
B9 B5 H5 119.0 . . ?
B9 B5 B8 56.3(4) . . ?
C1 B3 B2 55.7(2) . . ?
C1 B3 B4 55.2(2) . . ?
C1 B3 H3A 121.5 . . ?
C1 B3 B8 108.1(4) . . ?
C1 B3 B7 108.5(4) . . ?
B2 B3 H3A 130.6 . . ?
B4 B3 B2 90.0(3) . . ?
B4 B3 H3A 131.6 . . ?
B8 B3 B2 101.9(4) . . ?
B8 B3 B4 58.4(3) . . ?
B8 B3 H3A 121.3 . . ?
B7 B3 B2 59.0(3) . . ?
B7 B3 B4 100.7(4) . . ?
B7 B3 H3A 121.4 . . ?
B7 B3 B8 60.8(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
B4 B8 B5 58.9(3) . . ?
B4 B8 B3 61.6(3) . . ?
B4 B8 H8 120.3 . . ?
B4 B8 B7 102.0(3) . . ?
B5 B8 H8 131.1 . . ?
B5 B8 B7 89.9(4) . . ?
B3 B8 B5 102.3(4) . . ?
B3 B8 H8 120.0 . . ?
B3 B8 B7 59.4(3) . . ?
B9 B8 B4 111.8(5) . . ?
B9 B8 B5 57.6(4) . . ?
B9 B8 B3 111.8(4) . . ?
B9 B8 H8 118.6 . . ?
B9 B8 B7 56.7(3) . . ?
B7 B8 H8 131.4 . . ?
C14 O5 C13 116.2(7) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
B6 B9 H9 123(3) . . ?
B5 B9 B6 65.9(3) . . ?
B5 B9 H9 136(3) . . ?
B8 B9 B6 101.0(4) . . ?
B8 B9 B5 66.0(4) . . ?
B8 B9 B7 66.7(4) . . ?
B8 B9 H9 135(3) . . ?
B7 B9 B6 65.6(3) . . ?
B7 B9 B5 100.8(4) . . ?
B7 B9 H9 122(3) . . ?
B2 B7 B6 59.6(3) . . ?
B2 B7 B3 61.5(3) . . ?
B2 B7 B8 102.9(3) . . ?
B2 B7 H7A 119.6 . . ?
B6 B7 B8 90.4(4) . . ?
B6 B7 H7A 130.7 . . ?
B3 B7 B6 102.6(3) . . ?
B3 B7 B8 59.8(3) . . ?
B3 B7 H7A 120.0 . . ?
B8 B7 H7A 131.1 . . ?
B9 B7 B2 112.9(4) . . ?
B9 B7 B6 58.1(4) . . ?
B9 B7 B3 112.0(4) . . ?
B9 B7 B8 56.6(4) . . ?
B9 B7 H7A 118.3 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C14 H14A 99.2 . . ?
O5 C14 H14B 99.2 . . ?
H14A C14 H14B 104.0 . . ?
C15 C14 O5 149.9(12) . . ?
C15 C14 H14A 99.2 . . ?
C15 C14 H14B 99.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
C14A C15 H15D 109.5 . . ?
C14A C15 H15E 109.5 . . ?
C14A C15 H15F 109.5 . . ?
C13 O5A C14A 124.7(6) . . ?
C15 C14A O5A 110.9(7) . . ?
C15 C14A H14C 109.5 . . ?
C15 C14A H14D 109.5 . . ?
O5A C14A H14C 109.5 . . ?
O5A C14A H14D 109.5 . . ?
H14C C14A H14D 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_wmj18010_0m
_database_code_depnum_ccdc_archive 'CCDC 1854827'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;
_audit_creation_date             2018-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H29 B9 N O, C8 H20 N'
_chemical_formula_sum            'C29 H49 B9 N2 O'
_chemical_formula_weight         538.99
_chemical_absolute_configuration rmad
_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 0.0150 0.0070 '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 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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'

_cell_length_a                   7.9588(2)
_cell_length_b                   22.6600(4)
_cell_length_c                   18.5609(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.4330(10)
_cell_angle_gamma                90
_cell_volume                     3347.30(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.97
_cell_measurement_theta_min      5.363
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1117 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.6841. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12239
_diffrn_reflns_point_group_measured_fraction_full 0.839
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.017
_diffrn_reflns_theta_min         5.360
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.695
_reflns_Friedel_fraction_max     0.683
_reflns_number_gt                5165
_reflns_number_total             5310
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 2035 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5310
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.5679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0857
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C24(H24A,H24B), C26(H26A,H26B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C),
 C27(H27A,H27B,H27C), C29(H29A,H29B,H29C)
2.e Boron cage BH refined with riding coordinates:
 B4(H4), B5(H5), B6(H6A), B7(H7A), B8(H8), B9(H9A)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.39117(17) 0.61539(6) 0.38201(7) 0.0334(3) Uani 1 1 d . . . . .
N1 N 0.4161(2) 0.69632(7) 0.45201(9) 0.0348(4) Uani 1 1 d . . . . .
H1 H 0.472486 0.712338 0.487978 0.042 Uiso 1 1 calc R . . . .
C1 C 0.6079(2) 0.61640(8) 0.47089(9) 0.0209(4) Uani 1 1 d . . . . .
C2 C 0.4613(2) 0.64189(8) 0.43108(9) 0.0221(4) Uani 1 1 d . . . . .
C3 C 0.2806(3) 0.73088(9) 0.41964(11) 0.0313(4) Uani 1 1 d . . . . .
H3 H 0.215257 0.704746 0.386268 0.038 Uiso 1 1 calc R . . . .
C4 C 0.1641(3) 0.75286(12) 0.47754(13) 0.0441(5) Uani 1 1 d . . . . .
H4A H 0.225712 0.779360 0.510042 0.066 Uiso 1 1 calc GR . . . .
H4B H 0.120757 0.719247 0.504925 0.066 Uiso 1 1 calc GR . . . .
H4C H 0.070196 0.774262 0.455235 0.066 Uiso 1 1 calc GR . . . .
C5 C 0.3532(3) 0.78119(11) 0.37640(13) 0.0453(5) Uani 1 1 d . . . . .
H5A H 0.425711 0.765357 0.338606 0.068 Uiso 1 1 calc GR . . . .
H5B H 0.419174 0.806904 0.408252 0.068 Uiso 1 1 calc GR . . . .
H5C H 0.261598 0.803941 0.354302 0.068 Uiso 1 1 calc GR . . . .
C6 C 0.5187(2) 0.65136(8) 0.60573(9) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.403776 0.643713 0.595193 0.030 Uiso 1 1 calc R . . . .
C7 C 0.5509(2) 0.68715(9) 0.66070(9) 0.0264(4) Uani 1 1 d . . . . .
H7 H 0.664967 0.689683 0.675875 0.032 Uiso 1 1 calc R . . . .
C8 C 0.4296(2) 0.72349(8) 0.70093(9) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.2594(3) 0.72578(10) 0.68333(10) 0.0333(4) Uani 1 1 d . . . . .
H9 H 0.216144 0.701287 0.646008 0.040 Uiso 1 1 calc R . . . .
C10 C 0.1522(3) 0.76354(11) 0.71984(12) 0.0423(5) Uani 1 1 d . . . . .
H10 H 0.036531 0.764936 0.706881 0.051 Uiso 1 1 calc R . . . .
C11 C 0.2118(3) 0.79912(11) 0.77481(12) 0.0452(6) Uani 1 1 d . . . . .
H11 H 0.137777 0.824784 0.799673 0.054 Uiso 1 1 calc R . . . .
C12 C 0.3798(3) 0.79703(11) 0.79324(12) 0.0464(6) Uani 1 1 d . . . . .
H12 H 0.421785 0.820990 0.831320 0.056 Uiso 1 1 calc R . . . .
C13 C 0.4872(3) 0.76004(10) 0.75628(11) 0.0384(5) Uani 1 1 d . . . . .
H13 H 0.603057 0.759521 0.768908 0.046 Uiso 1 1 calc R . . . .
C14 C 0.4724(2) 0.50708(8) 0.50605(9) 0.0229(4) Uani 1 1 d . . . . .
H14 H 0.364522 0.521374 0.492492 0.027 Uiso 1 1 calc R . . . .
C15 C 0.4870(2) 0.45053(9) 0.52603(9) 0.0255(4) Uani 1 1 d . . . . .
H15 H 0.598203 0.436854 0.534630 0.031 Uiso 1 1 calc R . . . .
C16 C 0.3525(2) 0.40698(8) 0.53631(9) 0.0260(4) Uani 1 1 d . . . . .
C17 C 0.3931(3) 0.35176(9) 0.56587(12) 0.0347(4) Uani 1 1 d . . . . .
H17 H 0.507006 0.342625 0.576632 0.042 Uiso 1 1 calc R . . . .
C18 C 0.2692(3) 0.31035(10) 0.57960(13) 0.0424(5) Uani 1 1 d . . . . .
H18 H 0.298986 0.273022 0.599170 0.051 Uiso 1 1 calc R . . . .
C19 C 0.1029(3) 0.32300(10) 0.56503(12) 0.0396(5) Uani 1 1 d . . . . .
H19 H 0.017914 0.294898 0.575421 0.047 Uiso 1 1 calc R . . . .
C20 C 0.0610(3) 0.37723(10) 0.53500(11) 0.0359(5) Uani 1 1 d . . . . .
H20 H -0.053222 0.386167 0.524428 0.043 Uiso 1 1 calc R . . . .
C21 C 0.1853(3) 0.41844(8) 0.52036(10) 0.0295(4) Uani 1 1 d . . . . .
H21 H 0.155198 0.455107 0.499059 0.035 Uiso 1 1 calc R . . . .
B2 B 0.6240(3) 0.55058(9) 0.50397(10) 0.0221(4) Uani 1 1 d . . . . .
B3 B 0.6509(3) 0.62051(9) 0.55658(10) 0.0235(4) Uani 1 1 d . . . . .
B4 B 0.7828(3) 0.65098(10) 0.48338(10) 0.0251(4) Uani 1 1 d . . . . .
H4 H 0.801273 0.697619 0.465109 0.030 Uiso 1 1 calc R . . . .
B5 B 0.7567(3) 0.58161(10) 0.43154(10) 0.0245(4) Uani 1 1 d . . . . .
H5 H 0.754852 0.573230 0.372072 0.029 Uiso 1 1 calc R . . . .
B6 B 0.7678(3) 0.55470(10) 0.58086(10) 0.0259(4) Uani 1 1 d . . . . .
H6A H 0.736601 0.530668 0.631767 0.031 Uiso 1 1 calc R . . . .
B7 B 0.8783(3) 0.62495(10) 0.56622(11) 0.0270(4) Uani 1 1 d . . . . .
H7A H 0.935422 0.657088 0.605172 0.032 Uiso 1 1 calc R . . . .
B8 B 0.9526(3) 0.59791(11) 0.47809(11) 0.0282(4) Uani 1 1 d . . . . .
H8 H 1.068486 0.608510 0.446776 0.034 Uiso 1 1 calc R . . . .
B9 B 0.8416(3) 0.52752(10) 0.49287(11) 0.0263(4) Uani 1 1 d . . . . .
H9A H 0.869497 0.481816 0.473366 0.032 Uiso 1 1 calc R . . . .
B10 B 0.9725(3) 0.55817(10) 0.55548(11) 0.0295(5) Uani 1 1 d . . . . .
N2 N 0.2674(2) 0.48209(8) 0.26819(8) 0.0329(4) Uani 1 1 d . . . . .
C22 C 0.1436(3) 0.53015(10) 0.28897(11) 0.0387(5) Uani 1 1 d . . . . .
H22A H 0.072786 0.515193 0.328603 0.046 Uiso 1 1 calc R . . . .
H22B H 0.207695 0.564355 0.307769 0.046 Uiso 1 1 calc R . . . .
C23 C 0.0304(4) 0.55117(15) 0.22902(16) 0.0630(8) Uani 1 1 d . . . . .
H23A H -0.047992 0.580674 0.247730 0.094 Uiso 1 1 calc GR . . . .
H23B H -0.032902 0.517664 0.209378 0.094 Uiso 1 1 calc GR . . . .
H23C H 0.098378 0.568862 0.190870 0.094 Uiso 1 1 calc GR . . . .
C24 C 0.3772(3) 0.50205(10) 0.20667(10) 0.0344(5) Uani 1 1 d . . . . .
H24A H 0.451930 0.469025 0.193018 0.041 Uiso 1 1 calc R . . . .
H24B H 0.304407 0.510983 0.164590 0.041 Uiso 1 1 calc R . . . .
C25 C 0.4840(3) 0.55544(12) 0.22283(12) 0.0491(6) Uani 1 1 d . . . . .
H25A H 0.556734 0.547224 0.264480 0.074 Uiso 1 1 calc GR . . . .
H25B H 0.411308 0.589155 0.233593 0.074 Uiso 1 1 calc GR . . . .
H25C H 0.553454 0.564635 0.180922 0.074 Uiso 1 1 calc GR . . . .
C26 C 0.1777(4) 0.42709(11) 0.24185(12) 0.0490(6) Uani 1 1 d . . . . .
H26A H 0.113790 0.437150 0.197564 0.059 Uiso 1 1 calc R . . . .
H26B H 0.263240 0.397363 0.228606 0.059 Uiso 1 1 calc R . . . .
C27 C 0.0587(6) 0.39950(17) 0.29491(18) 0.0896(13) Uani 1 1 d . . . . .
H27A H 0.121223 0.387465 0.338172 0.134 Uiso 1 1 calc GR . . . .
H27B H 0.005332 0.364854 0.272968 0.134 Uiso 1 1 calc GR . . . .
H27C H -0.027731 0.428253 0.308105 0.134 Uiso 1 1 calc GR . . . .
C28 C 0.3730(4) 0.46921(11) 0.33496(11) 0.0461(6) Uani 1 1 d . . . . .
H28A H 0.425688 0.506492 0.351348 0.055 Uiso 1 1 calc R . . . .
H28B H 0.297451 0.455616 0.373702 0.055 Uiso 1 1 calc R . . . .
C29 C 0.5091(5) 0.42383(17) 0.32519(17) 0.0828(12) Uani 1 1 d . . . . .
H29A H 0.574125 0.420034 0.369997 0.124 Uiso 1 1 calc GR . . . .
H29B H 0.583599 0.436204 0.286196 0.124 Uiso 1 1 calc GR . . . .
H29C H 0.458185 0.385700 0.313002 0.124 Uiso 1 1 calc GR . . . .
H10A H 1.082(3) 0.5401(11) 0.5815(12) 0.033(6) Uiso 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
O001 C2 1.222(2) . ?
N1 H1 0.8800 . ?
N1 C2 1.343(2) . ?
N1 C3 1.458(2) . ?
C1 C2 1.493(2) . ?
C1 B2 1.618(3) . ?
C1 B3 1.627(2) . ?
C1 B4 1.613(3) . ?
C1 B5 1.604(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.509(3) . ?
C3 C5 1.511(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 0.9500 . ?
C6 C7 1.327(3) . ?
C6 B3 1.563(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.476(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.394(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.339(3) . ?
C14 B2 1.559(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.470(3) . ?
C16 C17 1.403(3) . ?
C16 C21 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(3) . ?
C21 H21 0.9500 . ?
B2 B3 1.873(3) . ?
B2 B5 1.854(3) . ?
B2 B6 1.825(3) . ?
B2 B9 1.822(3) . ?
B3 B4 1.856(3) . ?
B3 B6 1.813(3) . ?
B3 B7 1.820(3) . ?
B4 H4 1.1200 . ?
B4 B5 1.854(3) . ?
B4 B7 1.809(3) . ?
B4 B8 1.812(3) . ?
B5 H5 1.1200 . ?
B5 B8 1.815(3) . ?
B5 B9 1.801(3) . ?
B6 H6A 1.1200 . ?
B6 B7 1.840(3) . ?
B6 B9 1.846(3) . ?
B6 B10 1.702(3) . ?
B7 H7A 1.1200 . ?
B7 B8 1.848(3) . ?
B7 B10 1.701(3) . ?
B8 H8 1.1200 . ?
B8 B9 1.845(3) . ?
B8 B10 1.702(3) . ?
B9 H9A 1.1200 . ?
B9 B10 1.703(3) . ?
B10 H10A 1.07(2) . ?
N2 C22 1.520(3) . ?
N2 C24 1.512(3) . ?
N2 C26 1.515(3) . ?
N2 C28 1.520(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.504(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.507(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.507(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.505(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 117.5 . . ?
C2 N1 C3 124.94(15) . . ?
C3 N1 H1 117.5 . . ?
C2 C1 B2 127.18(15) . . ?
C2 C1 B3 128.30(15) . . ?
C2 C1 B4 123.63(15) . . ?
C2 C1 B5 122.83(14) . . ?
B2 C1 B3 70.50(12) . . ?
B4 C1 B2 109.10(14) . . ?
B4 C1 B3 69.91(12) . . ?
B5 C1 B2 70.29(12) . . ?
B5 C1 B3 108.81(14) . . ?
B5 C1 B4 70.39(13) . . ?
O001 C2 N1 123.03(16) . . ?
O001 C2 C1 121.97(16) . . ?
N1 C2 C1 114.97(15) . . ?
N1 C3 H3 108.5 . . ?
N1 C3 C4 109.89(17) . . ?
N1 C3 C5 109.86(18) . . ?
C4 C3 H3 108.5 . . ?
C4 C3 C5 111.60(19) . . ?
C5 C3 H3 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6 116.7 . . ?
C7 C6 B3 126.53(17) . . ?
B3 C6 H6 116.7 . . ?
C6 C7 H7 116.3 . . ?
C6 C7 C8 127.35(17) . . ?
C8 C7 H7 116.3 . . ?
C9 C8 C7 122.77(17) . . ?
C9 C8 C13 117.68(18) . . ?
C13 C8 C7 119.43(18) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.58(19) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.2 . . ?
C12 C13 C8 121.6(2) . . ?
C12 C13 H13 119.2 . . ?
C15 C14 H14 118.4 . . ?
C15 C14 B2 123.13(16) . . ?
B2 C14 H14 118.4 . . ?
C14 C15 H15 116.0 . . ?
C14 C15 C16 128.10(17) . . ?
C16 C15 H15 116.0 . . ?
C17 C16 C15 118.95(17) . . ?
C21 C16 C15 123.08(17) . . ?
C21 C16 C17 117.93(18) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 120.92(19) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 121.11(18) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C1 B2 B3 54.99(10) . . ?
C1 B2 B5 54.49(11) . . ?
C1 B2 B6 107.29(14) . . ?
C1 B2 B9 107.12(14) . . ?
C14 B2 C1 122.22(15) . . ?
C14 B2 B3 127.42(15) . . ?
C14 B2 B5 134.66(14) . . ?
C14 B2 B6 119.60(14) . . ?
C14 B2 B9 123.92(15) . . ?
B5 B2 B3 89.63(13) . . ?
B6 B2 B3 58.69(11) . . ?
B6 B2 B5 100.98(13) . . ?
B9 B2 B3 101.34(13) . . ?
B9 B2 B5 58.65(11) . . ?
B9 B2 B6 60.82(11) . . ?
C1 B3 B2 54.52(10) . . ?
C1 B3 B4 54.68(10) . . ?
C1 B3 B6 107.45(14) . . ?
C1 B3 B7 107.52(14) . . ?
C6 B3 C1 117.29(15) . . ?
C6 B3 B2 127.45(15) . . ?
C6 B3 B4 130.38(15) . . ?
C6 B3 B6 124.70(15) . . ?
C6 B3 B7 126.25(15) . . ?
B4 B3 B2 89.78(12) . . ?
B6 B3 B2 59.33(11) . . ?
B6 B3 B4 101.31(14) . . ?
B6 B3 B7 60.87(12) . . ?
B7 B3 B2 101.99(14) . . ?
B7 B3 B4 58.93(11) . . ?
C1 B4 B3 55.41(10) . . ?
C1 B4 H4 122.0 . . ?
C1 B4 B5 54.57(11) . . ?
C1 B4 B7 108.71(15) . . ?
C1 B4 B8 108.25(15) . . ?
B3 B4 H4 130.4 . . ?
B5 B4 B3 90.16(13) . . ?
B5 B4 H4 131.1 . . ?
B7 B4 B3 59.54(11) . . ?
B7 B4 H4 120.6 . . ?
B7 B4 B5 102.09(14) . . ?
B7 B4 B8 61.37(12) . . ?
B8 B4 B3 102.64(14) . . ?
B8 B4 H4 120.7 . . ?
B8 B4 B5 59.33(11) . . ?
C1 B5 B2 55.21(11) . . ?
C1 B5 B4 55.04(11) . . ?
C1 B5 H5 121.9 . . ?
C1 B5 B8 108.55(14) . . ?
C1 B5 B9 108.76(14) . . ?
B2 B5 H5 130.3 . . ?
B4 B5 B2 90.43(12) . . ?
B4 B5 H5 131.0 . . ?
B8 B5 B2 102.94(13) . . ?
B8 B5 B4 59.19(11) . . ?
B8 B5 H5 120.6 . . ?
B9 B5 B2 59.77(11) . . ?
B9 B5 B4 102.07(13) . . ?
B9 B5 H5 120.6 . . ?
B9 B5 B8 61.37(12) . . ?
B2 B6 H6A 119.6 . . ?
B2 B6 B7 103.09(13) . . ?
B2 B6 B9 59.51(11) . . ?
B3 B6 B2 61.98(11) . . ?
B3 B6 H6A 119.6 . . ?
B3 B6 B7 59.78(11) . . ?
B3 B6 B9 102.75(13) . . ?
B7 B6 H6A 130.9 . . ?
B7 B6 B9 90.13(13) . . ?
B9 B6 H6A 131.2 . . ?
B10 B6 B2 112.46(14) . . ?
B10 B6 B3 112.57(16) . . ?
B10 B6 H6A 118.3 . . ?
B10 B6 B7 57.25(13) . . ?
B10 B6 B9 57.22(12) . . ?
B3 B7 B6 59.36(11) . . ?
B3 B7 H7A 119.8 . . ?
B3 B7 B8 102.66(13) . . ?
B4 B7 B3 61.53(11) . . ?
B4 B7 B6 102.07(13) . . ?
B4 B7 H7A 120.2 . . ?
B4 B7 B8 59.40(11) . . ?
B6 B7 H7A 131.2 . . ?
B6 B7 B8 90.02(13) . . ?
B8 B7 H7A 131.0 . . ?
B10 B7 B3 112.22(15) . . ?
B10 B7 B4 111.91(15) . . ?
B10 B7 B6 57.28(12) . . ?
B10 B7 H7A 118.5 . . ?
B10 B7 B8 57.12(12) . . ?
B4 B8 B5 61.48(12) . . ?
B4 B8 B7 59.23(11) . . ?
B4 B8 H8 120.2 . . ?
B4 B8 B9 101.97(14) . . ?
B5 B8 B7 102.10(14) . . ?
B5 B8 H8 120.3 . . ?
B5 B8 B9 58.94(11) . . ?
B7 B8 H8 131.2 . . ?
B9 B8 B7 89.91(14) . . ?
B9 B8 H8 131.3 . . ?
B10 B8 B4 111.73(15) . . ?
B10 B8 B5 111.63(16) . . ?
B10 B8 B7 57.09(12) . . ?
B10 B8 H8 118.7 . . ?
B10 B8 B9 57.24(12) . . ?
B2 B9 B6 59.67(11) . . ?
B2 B9 B8 103.04(14) . . ?
B2 B9 H9A 119.5 . . ?
B5 B9 B2 61.58(11) . . ?
B5 B9 B6 102.24(14) . . ?
B5 B9 B8 59.69(12) . . ?
B5 B9 H9A 120.0 . . ?
B6 B9 H9A 131.3 . . ?
B8 B9 B6 89.95(13) . . ?
B8 B9 H9A 130.9 . . ?
B10 B9 B2 112.53(15) . . ?
B10 B9 B5 112.23(16) . . ?
B10 B9 B6 57.14(12) . . ?
B10 B9 B8 57.15(12) . . ?
B10 B9 H9A 118.4 . . ?
B6 B10 B9 65.64(13) . . ?
B6 B10 H10A 129.2(13) . . ?
B7 B10 B6 65.47(13) . . ?
B7 B10 B8 65.79(13) . . ?
B7 B10 B9 100.06(14) . . ?
B7 B10 H10A 130.1(13) . . ?
B8 B10 B6 100.06(15) . . ?
B8 B10 B9 65.62(13) . . ?
B8 B10 H10A 130.7(13) . . ?
B9 B10 H10A 129.9(13) . . ?
C22 N2 C28 106.63(15) . . ?
C24 N2 C22 110.89(17) . . ?
C24 N2 C26 106.02(15) . . ?
C24 N2 C28 110.73(17) . . ?
C26 N2 C22 111.48(18) . . ?
C26 N2 C28 111.18(18) . . ?
N2 C22 H22A 108.5 . . ?
N2 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C23 C22 N2 115.15(18) . . ?
C23 C22 H22A 108.5 . . ?
C23 C22 H22B 108.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 108.6 . . ?
N2 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 N2 114.71(16) . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 H26A 108.5 . . ?
N2 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
C27 C26 N2 115.28(19) . . ?
C27 C26 H26A 108.5 . . ?
C27 C26 H26B 108.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N2 C28 H28A 108.5 . . ?
N2 C28 H28B 108.5 . . ?
H28A C28 H28B 107.5 . . ?
C29 C28 N2 115.25(19) . . ?
C29 C28 H28A 108.5 . . ?
C29 C28 H28B 108.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_wmj18026_0m
_database_code_depnum_ccdc_archive 'CCDC 1854826'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;
_audit_creation_date             2018-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H25 B9 N Na O5 S2'
_chemical_formula_sum            'C11 H25 B9 N Na O5 S2'
_chemical_formula_weight         435.72
_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 0.0150 0.0070 '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 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1104 0.0938 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4250 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3755(8)
_cell_length_b                   11.2861(6)
_cell_length_c                   51.571(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8367.1(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9527
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.91
_cell_measurement_theta_min      3.409
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  0.7431
_exptl_absorpt_correction_T_min  0.4926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1919 before and 0.1338 after correction. The Ratio of minimum to maximum transmission is 0.6629. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1503
_diffrn_reflns_av_unetI/netI     0.1156
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            73033
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.138
_diffrn_reflns_theta_min         4.007
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5190
_reflns_number_total             7759
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         7759
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1897
_refine_ls_R_factor_gt           0.1650
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1100P)²+82.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3796
_refine_ls_wR_factor_ref         0.3961
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C3-C5
 1.53 with sigma of 0.02
 C3-C4
 1.53 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C9(H9), C10(H10)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C)
3.d Boron cage BH refined with riding coordinates:
 B2(H2), B3(H3A), B5(H5), B6(H6A), B7(H7A), B8(H8)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.71597(13) 0.12013(17) 0.18959(5) 0.0598(6) Uani 1 1 d . . . . .
S2 S 0.44459(13) -0.58465(17) 0.16933(5) 0.0639(6) Uani 1 1 d . . . . .
Na1 Na 0.8123(2) -0.1193(3) 0.14792(8) 0.0826(11) Uani 1 1 d . . . . .
O1 O 0.4945(5) -0.1623(8) 0.14456(14) 0.094(2) Uani 1 1 d . . . . .
O2 O 0.7543(5) 0.0384(5) 0.17063(13) 0.0775(18) Uani 1 1 d . . . . .
O3 O 0.6901(4) 0.2333(6) 0.17988(14) 0.0805(18) Uani 1 1 d . . . . .
O4 O 0.5358(4) -0.5650(6) 0.15853(14) 0.0822(19) Uani 1 1 d . . . . .
O5 O 0.3696(4) -0.6092(5) 0.15226(13) 0.0756(17) Uani 1 1 d . . . . .
N1 N 0.3451(6) -0.1323(9) 0.14006(18) 0.094(3) Uani 1 1 d . . . . .
H1 H 0.293806 -0.112258 0.148275 0.113 Uiso 1 1 calc R . . . .
C1 C 0.4072(4) -0.1403(7) 0.18303(15) 0.0490(17) Uani 1 1 d . . . . .
C2 C 0.4190(5) -0.1506(8) 0.15392(19) 0.066(2) Uani 1 1 d . . . . .
C3 C 0.3405(8) -0.1424(10) 0.1121(2) 0.091(3) Uani 1 1 d D . . . .
H3 H 0.402362 -0.127325 0.103874 0.109 Uiso 1 1 calc R . . . .
C4 C 0.2668(15) -0.061(2) 0.1015(3) 0.203(10) Uani 1 1 d D . . . .
H4A H 0.258602 -0.076353 0.082941 0.304 Uiso 1 1 calc GR . . . .
H4B H 0.285691 0.021316 0.104133 0.304 Uiso 1 1 calc GR . . . .
H4C H 0.207920 -0.075784 0.110570 0.304 Uiso 1 1 calc GR . . . .
C5 C 0.3135(17) -0.2776(14) 0.1110(4) 0.210(10) Uani 1 1 d D . . . .
H5A H 0.358233 -0.320124 0.100112 0.315 Uiso 1 1 calc GR . . . .
H5B H 0.250947 -0.285898 0.103646 0.315 Uiso 1 1 calc GR . . . .
H5C H 0.314380 -0.310745 0.128560 0.315 Uiso 1 1 calc GR . . . .
C6 C 0.5763(6) -0.0407(7) 0.19449(18) 0.062(2) Uani 1 1 d . . . . .
H6 H 0.608259 -0.080522 0.180923 0.074 Uiso 1 1 calc R . . . .
C7 C 0.6159(6) 0.0578(6) 0.2038(2) 0.068(2) Uani 1 1 d . . . . .
H7 H 0.589153 0.095316 0.218501 0.081 Uiso 1 1 calc R . . . .
C8 C 0.7911(5) 0.1500(8) 0.21639(19) 0.069(2) Uani 1 1 d . . . . .
H8A H 0.789149 0.083336 0.228552 0.104 Uiso 1 1 calc GR . . . .
H8B H 0.770437 0.222278 0.225209 0.104 Uiso 1 1 calc GR . . . .
H8C H 0.854857 0.160780 0.210107 0.104 Uiso 1 1 calc GR . . . .
C9 C 0.4676(6) -0.3654(9) 0.18873(19) 0.073(2) Uani 1 1 d . . . . .
H9 H 0.528754 -0.370172 0.181836 0.088 Uiso 1 1 calc R . . . .
C10 C 0.4121(5) -0.4584(7) 0.18643(16) 0.0540(18) Uani 1 1 d . . . . .
H10 H 0.352576 -0.456175 0.194397 0.065 Uiso 1 1 calc R . . . .
C11 C 0.4489(6) -0.6972(8) 0.1921(2) 0.080(3) Uani 1 1 d . . . . .
H11A H 0.385605 -0.716648 0.197753 0.120 Uiso 1 1 calc GR . . . .
H11B H 0.485679 -0.671285 0.207040 0.120 Uiso 1 1 calc GR . . . .
H11C H 0.477736 -0.767516 0.184356 0.120 Uiso 1 1 calc GR . . . .
B1 B 0.4853(6) -0.0952(6) 0.2035(2) 0.065(3) Uani 1 1 d . . . . .
B2 B 0.3610(6) -0.0361(9) 0.2002(2) 0.068(3) Uani 1 1 d . . . . .
H2 H 0.333846 0.048227 0.191569 0.082 Uiso 1 1 calc R . . . .
B3 B 0.3154(6) -0.1873(10) 0.1972(2) 0.067(3) Uani 1 1 d . . . . .
H3A H 0.254070 -0.223236 0.186354 0.081 Uiso 1 1 calc R . . . .
B4 B 0.4352(6) -0.2427(7) 0.20296(19) 0.054(2) Uani 1 1 d . . . . .
B5 B 0.4715(6) -0.1825(9) 0.2329(2) 0.060(2) Uani 1 1 d . . . . .
H5 H 0.534841 -0.216029 0.243213 0.072 Uiso 1 1 calc R . . . .
B6 B 0.4234(6) -0.0391(9) 0.2321(2) 0.069(3) Uani 1 1 d . . . . .
H6A H 0.449112 0.044167 0.241522 0.083 Uiso 1 1 calc R . . . .
B7 B 0.3029(7) -0.0984(8) 0.2273(2) 0.067(3) Uani 1 1 d . . . . .
H7A H 0.232833 -0.064240 0.233228 0.080 Uiso 1 1 calc R . . . .
B8 B 0.3574(8) -0.2496(9) 0.2277(2) 0.075(3) Uani 1 1 d . . . . .
H8 H 0.329442 -0.337848 0.233840 0.090 Uiso 1 1 calc R . . . .
B9 B 0.3798(6) -0.1412(8) 0.2512(2) 0.057(2) Uani 1 1 d . . . . .
H9A H 0.373(4) -0.146(5) 0.2743(12) 0.033(15) Uiso 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
S1 O2 1.453(6) . ?
S1 O3 1.422(6) . ?
S1 C7 1.761(9) . ?
S1 C8 1.786(9) . ?
S2 O4 1.442(7) . ?
S2 O5 1.419(6) . ?
S2 C10 1.739(7) . ?
S2 C11 1.731(10) . ?
Na1 O2 2.288(7) . ?
Na1 O3 2.342(8) 7_755 ?
Na1 O4 2.333(7) 7_765 ?
O1 C2 1.195(10) . ?
N1 C2 1.297(11) . ?
N1 C3 1.447(14) . ?
C1 C2 1.515(12) . ?
C1 B1 1.622(12) . ?
C1 B2 1.613(12) . ?
C1 B3 1.599(11) . ?
C1 B4 1.598(11) . ?
C3 C4 1.504(15) . ?
C3 C5 1.575(14) . ?
C6 C7 1.339(11) . ?
C6 B1 1.517(12) . ?
C9 C10 1.323(11) . ?
C9 B4 1.635(12) . ?
B1 B2 1.915(13) . ?
B1 B4 1.814(11) . ?
B1 B5 1.821(15) . ?
B1 B6 1.838(15) . ?
B2 B3 1.834(15) . ?
B2 B6 1.877(17) . ?
B2 B7 1.777(15) . ?
B3 B4 1.856(13) . ?
B3 B7 1.859(16) . ?
B3 B8 1.826(17) . ?
B4 B5 1.766(14) . ?
B4 B8 1.697(13) . ?
B5 B6 1.761(14) . ?
B5 B8 1.826(14) . ?
B5 B9 1.686(13) . ?
B6 B7 1.874(14) . ?
B6 B9 1.639(15) . ?
B7 B8 1.879(14) . ?
B7 B9 1.722(14) . ?
B8 B9 1.752(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C7 109.6(4) . . ?
O2 S1 C8 114.3(4) . . ?
O3 S1 O2 115.7(4) . . ?
O3 S1 C7 106.9(4) . . ?
O3 S1 C8 105.1(4) . . ?
C7 S1 C8 104.3(4) . . ?
O4 S2 C10 108.3(4) . . ?
O4 S2 C11 110.0(4) . . ?
O5 S2 O4 118.8(4) . . ?
O5 S2 C10 105.7(4) . . ?
O5 S2 C11 107.7(4) . . ?
C11 S2 C10 105.5(5) . . ?
O2 Na1 O3 100.7(3) . 7_755 ?
O2 Na1 O4 91.0(3) . 7_765 ?
O4 Na1 O3 92.0(3) 7_765 7_755 ?
S1 O2 Na1 167.6(4) . . ?
S1 O3 Na1 152.9(4) . 7_765 ?
S2 O4 Na1 154.3(5) . 7_755 ?
C2 N1 C3 125.0(9) . . ?
C2 C1 B1 126.2(7) . . ?
C2 C1 B2 130.1(7) . . ?
C2 C1 B3 121.3(7) . . ?
C2 C1 B4 123.6(7) . . ?
B2 C1 B1 72.6(6) . . ?
B3 C1 B1 112.2(7) . . ?
B3 C1 B2 69.6(6) . . ?
B4 C1 B1 68.6(5) . . ?
B4 C1 B2 106.2(7) . . ?
B4 C1 B3 71.0(6) . . ?
O1 C2 N1 122.6(9) . . ?
O1 C2 C1 120.7(8) . . ?
N1 C2 C1 116.2(7) . . ?
N1 C3 C4 110.2(10) . . ?
N1 C3 C5 97.1(11) . . ?
C4 C3 C5 113.8(15) . . ?
C7 C6 B1 126.5(8) . . ?
C6 C7 S1 122.0(7) . . ?
C10 C9 B4 122.7(8) . . ?
C9 C10 S2 122.2(6) . . ?
C1 B1 B2 53.5(5) . . ?
C1 B1 B4 55.1(5) . . ?
C1 B1 B5 107.3(6) . . ?
C1 B1 B6 107.2(6) . . ?
C6 B1 C1 121.7(9) . . ?
C6 B1 B2 129.5(7) . . ?
C6 B1 B4 135.2(7) . . ?
C6 B1 B5 124.6(8) . . ?
C6 B1 B6 121.5(7) . . ?
B4 B1 B2 87.0(5) . . ?
B4 B1 B5 58.1(5) . . ?
B4 B1 B6 97.8(6) . . ?
B5 B1 B2 99.3(6) . . ?
B5 B1 B6 57.6(6) . . ?
B6 B1 B2 60.0(6) . . ?
C1 B2 B1 53.9(5) . . ?
C1 B2 B3 54.8(5) . . ?
C1 B2 B6 105.7(6) . . ?
C1 B2 B7 109.7(7) . . ?
B3 B2 B1 91.0(6) . . ?
B3 B2 B6 103.1(7) . . ?
B6 B2 B1 58.0(5) . . ?
B7 B2 B1 103.3(7) . . ?
B7 B2 B3 62.0(6) . . ?
B7 B2 B6 61.6(6) . . ?
C1 B3 B2 55.6(5) . . ?
C1 B3 B4 54.5(5) . . ?
C1 B3 B7 106.4(7) . . ?
C1 B3 B8 104.4(7) . . ?
B2 B3 B4 88.2(5) . . ?
B2 B3 B7 57.5(6) . . ?
B4 B3 B7 97.9(7) . . ?
B8 B3 B2 99.7(7) . . ?
B8 B3 B4 54.9(5) . . ?
B8 B3 B7 61.3(6) . . ?
C1 B4 C9 113.3(7) . . ?
C1 B4 B1 56.3(5) . . ?
C1 B4 B3 54.5(5) . . ?
C1 B4 B5 111.0(6) . . ?
C1 B4 B8 110.5(6) . . ?
C9 B4 B1 132.1(7) . . ?
C9 B4 B3 118.6(7) . . ?
C9 B4 B5 129.3(7) . . ?
C9 B4 B8 119.1(7) . . ?
B1 B4 B3 93.5(6) . . ?
B5 B4 B1 61.1(6) . . ?
B5 B4 B3 106.6(6) . . ?
B8 B4 B1 107.0(7) . . ?
B8 B4 B3 61.7(6) . . ?
B8 B4 B5 63.6(6) . . ?
B1 B5 B8 101.5(7) . . ?
B4 B5 B1 60.7(5) . . ?
B4 B5 B8 56.3(5) . . ?
B6 B5 B1 61.7(6) . . ?
B6 B5 B4 102.5(7) . . ?
B6 B5 B8 91.4(6) . . ?
B9 B5 B1 113.6(7) . . ?
B9 B5 B4 111.3(6) . . ?
B9 B5 B6 56.7(5) . . ?
B9 B5 B8 59.7(5) . . ?
B1 B6 B2 62.0(6) . . ?
B1 B6 B7 102.6(7) . . ?
B5 B6 B1 60.7(5) . . ?
B5 B6 B2 103.0(7) . . ?
B5 B6 B7 92.2(6) . . ?
B7 B6 B2 56.6(6) . . ?
B9 B6 B1 115.1(7) . . ?
B9 B6 B2 110.9(7) . . ?
B9 B6 B5 59.3(6) . . ?
B9 B6 B7 58.3(6) . . ?
B2 B7 B3 60.5(6) . . ?
B2 B7 B6 61.8(6) . . ?
B2 B7 B8 99.8(7) . . ?
B3 B7 B6 102.3(7) . . ?
B3 B7 B8 58.5(6) . . ?
B6 B7 B8 86.4(6) . . ?
B9 B7 B2 111.8(7) . . ?
B9 B7 B3 112.5(7) . . ?
B9 B7 B6 54.0(6) . . ?
B9 B7 B8 58.0(6) . . ?
B3 B8 B7 60.2(6) . . ?
B4 B8 B3 63.5(6) . . ?
B4 B8 B5 60.0(6) . . ?
B4 B8 B7 103.1(7) . . ?
B4 B8 B9 111.5(7) . . ?
B5 B8 B3 105.3(7) . . ?
B5 B8 B7 90.0(6) . . ?
B9 B8 B3 112.8(7) . . ?
B9 B8 B5 56.2(6) . . ?
B9 B8 B7 56.5(6) . . ?
B5 B9 B7 100.4(7) . . ?
B5 B9 B8 64.1(6) . . ?
B6 B9 B5 64.0(6) . . ?
B6 B9 B7 67.7(6) . . ?
B6 B9 B8 98.5(7) . . ?
B7 B9 B8 65.5(6) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.343 -0.571 0.000 2050.0 57.5 ?
2 -0.561 -0.779 0.500 2050.0 57.5 ?

_olex2_submission_special_instructions 'No special instructions were received'
