# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 
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data_mo_TSL2_119_0m
_database_code_depnum_ccdc_archive 'CCDC 1483204'
_audit_update_record             
;
2016-06-02 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N O S'
_chemical_formula_weight         357.45
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'

_symmetry_cell_setting           Orthorhombic
_space_group_IT_number           19
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_space_group_name_Hall           'P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.6327(6)
_cell_length_b                   14.2928(15)
_cell_length_c                   21.544(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1734.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    616
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      20.94

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            11276
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.710
_diffrn_reflns_theta_max         26.346
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3394
_reflns_number_gt                2650
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_max     0.936
_reflns_Friedel_fraction_full    0.943

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.1691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_number_reflns         3394
_refine_ls_number_parameters     254
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.1740(6) 0.3995(2) 0.88135(19) 0.0234(6) Uani 0.6 1 d D U P A 1
S1' S 0.0377(12) 0.3605(4) 0.8330(4) 0.0260(10) Uani 0.4 1 d D U P A 2
N1 N 0.2020(6) 0.6320(2) 0.55737(13) 0.0200(7) Uani 1 1 d . . . . .
O1 O 0.2759(5) 0.63591(19) 0.97383(11) 0.0269(7) Uani 1 1 d . . . . .
C1 C 0.4534(7) 0.7635(3) 0.83682(15) 0.0176(8) Uani 1 1 d . . . . .
H1 H 0.6199 0.7672 0.8209 0.021 Uiso 1 1 calc R U . . .
C2 C 0.3283(7) 0.6755(3) 0.81462(15) 0.0175(8) Uani 1 1 d . . . . .
C3 C 0.2573(7) 0.6201(3) 0.86243(15) 0.0174(9) Uani 1 1 d . . . . .
C4 C 0.3213(7) 0.6657(3) 0.92220(16) 0.0204(9) Uani 1 1 d . . . . .
C5 C 0.4459(7) 0.7570(2) 0.90845(14) 0.0188(8) Uani 1 1 d . . . . .
H5 H 0.6087 0.7589 0.9269 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2959(7) 0.8451(3) 0.92713(16) 0.0232(9) Uani 1 1 d . . . . .
H6 H 0.2272 0.8449 0.9699 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4531(7) 0.9278(3) 0.91069(17) 0.0216(9) Uani 1 1 d . . . . .
H7 H 0.5312 0.9682 0.9391 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4611(8) 0.9333(3) 0.84908(17) 0.0236(9) Uani 1 1 d . . . . .
H8 H 0.5460 0.9785 0.8256 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3115(7) 0.8548(3) 0.82300(16) 0.0216(9) Uani 1 1 d . . . . .
H9 H 0.2546 0.8630 0.7794 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1178(6) 0.8487(3) 0.87343(17) 0.0244(9) Uani 1 1 d . . . . .
H10A H 0.0147 0.9047 0.8748 0.029 Uiso 1 1 calc R U . . .
H10B H 0.0203 0.7912 0.8702 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2840(7) 0.6620(3) 0.74757(15) 0.0168(8) Uani 1 1 d . . . . .
C12 C 0.4428(7) 0.6970(3) 0.70429(15) 0.0177(8) Uani 1 1 d . . . . .
H12 H 0.5791 0.7302 0.7180 0.021 Uiso 1 1 calc R U . . .
C13 C 0.4057(7) 0.6842(3) 0.64086(15) 0.0172(9) Uani 1 1 d . . . . .
C14 C 0.5358(7) 0.7075(3) 0.58580(16) 0.0219(9) Uani 1 1 d . . . . .
H14 H 0.6828 0.7400 0.5837 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4072(7) 0.6740(3) 0.53716(16) 0.0225(10) Uani 1 1 d . . . . .
H15 H 0.4534 0.6789 0.4949 0.027 Uiso 1 1 calc R U . . .
C16 C 0.1976(7) 0.6371(2) 0.62135(15) 0.0168(8) Uani 1 1 d . . . . .
C17 C 0.0288(7) 0.6043(2) 0.66331(16) 0.0179(8) Uani 1 1 d . . . . .
H17 H -0.1125 0.5745 0.6495 0.022 Uiso 1 1 calc R U . . .
C18 C 0.0751(7) 0.6169(2) 0.72588(15) 0.0167(8) Uani 1 1 d . . . . .
H18 H -0.0367 0.5945 0.7554 0.020 Uiso 1 1 calc R U . . .
C19 C 0.0359(8) 0.5797(3) 0.51830(16) 0.0269(10) Uani 1 1 d . . . . .
H19A H 0.0251 0.6095 0.4774 0.040 Uiso 1 1 calc R U . . .
H19B H -0.1212 0.5792 0.5379 0.040 Uiso 1 1 calc R U . . .
H19C H 0.0926 0.5153 0.5134 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1352(6) 0.5296(3) 0.86065(15) 0.0185(9) Uani 1 1 d . . . . .
C21 C 0.2067(7) 0.4531(3) 0.82499(17) 0.0253(9) Uani 1 1 d D . . . .
H21A H 0.3483 0.4514 0.7999 0.030 Uiso 0.6 1 d R U P A 1
H21B H 0.3434 0.4544 0.7981 0.030 Uiso 0.4 1 d R U P A 2
C22 C 0.058(3) 0.3797(10) 0.8310(9) 0.032(3) Uani 0.6 1 d D U P A 1
H22 H 0.0799 0.3224 0.8095 0.038 Uiso 0.6 1 calc R U P A 1
C22' C -0.151(4) 0.4204(10) 0.8811(11) 0.023(4) Uani 0.4 1 d D U P A 2
H22' H -0.2959 0.3956 0.8969 0.028 Uiso 0.4 1 calc R U P A 2
C23 C -0.0679(8) 0.5091(3) 0.89410(17) 0.0280(10) Uani 1 1 d D . . . .
H23A H -0.1427 0.5525 0.9220 0.034 Uiso 0.6 1 d R U P A 1
H23B H -0.1457 0.5514 0.9222 0.034 Uiso 0.4 1 d 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 C23 1.699(5) . ?
S1 C22 1.723(12) . ?
S1' C21 1.640(6) . ?
S1' C22' 1.715(12) . ?
N1 C15 1.373(5) . ?
N1 C16 1.381(4) . ?
N1 C19 1.464(5) . ?
O1 C4 1.218(4) . ?
C1 C2 1.518(5) . ?
C1 C5 1.547(4) . ?
C1 C9 1.559(5) . ?
C2 C3 1.360(5) . ?
C2 C11 1.479(4) . ?
C3 C20 1.466(5) . ?
C3 C4 1.488(5) . ?
C4 C5 1.512(5) . ?
C5 C6 1.568(5) . ?
C6 C7 1.519(5) . ?
C6 C10 1.532(5) . ?
C7 C8 1.330(5) . ?
C8 C9 1.511(5) . ?
C9 C10 1.543(5) . ?
C11 C12 1.385(5) . ?
C11 C18 1.421(5) . ?
C12 C13 1.394(5) . ?
C13 C16 1.416(5) . ?
C13 C14 1.434(5) . ?
C14 C15 1.361(5) . ?
C16 C17 1.393(5) . ?
C17 C18 1.385(5) . ?
C20 C23 1.383(5) . ?
C20 C21 1.395(5) . ?
C21 C22 1.347(11) . ?
C22' C23 1.381(11) . ?

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
C23 S1 C22 89.2(5) . . ?
C21 S1' C22' 91.2(6) . . ?
C15 N1 C16 108.0(3) . . ?
C15 N1 C19 125.4(3) . . ?
C16 N1 C19 126.1(3) . . ?
C2 C1 C5 104.6(3) . . ?
C2 C1 C9 113.3(3) . . ?
C5 C1 C9 103.1(3) . . ?
C3 C2 C11 127.9(3) . . ?
C3 C2 C1 112.4(3) . . ?
C11 C2 C1 119.6(3) . . ?
C2 C3 C20 129.2(3) . . ?
C2 C3 C4 109.2(3) . . ?
C20 C3 C4 121.5(3) . . ?
O1 C4 C3 125.9(4) . . ?
O1 C4 C5 125.3(3) . . ?
C3 C4 C5 108.7(3) . . ?
C4 C5 C1 105.1(3) . . ?
C4 C5 C6 113.1(3) . . ?
C1 C5 C6 102.9(3) . . ?
C7 C6 C10 100.4(3) . . ?
C7 C6 C5 104.5(3) . . ?
C10 C6 C5 100.7(3) . . ?
C8 C7 C6 107.3(3) . . ?
C7 C8 C9 108.0(3) . . ?
C8 C9 C10 100.1(3) . . ?
C8 C9 C1 105.3(3) . . ?
C10 C9 C1 100.4(3) . . ?
C6 C10 C9 94.0(3) . . ?
C12 C11 C18 118.5(3) . . ?
C12 C11 C2 120.1(3) . . ?
C18 C11 C2 121.3(3) . . ?
C11 C12 C13 121.0(4) . . ?
C12 C13 C16 118.5(3) . . ?
C12 C13 C14 134.7(4) . . ?
C16 C13 C14 106.8(3) . . ?
C15 C14 C13 106.4(3) . . ?
C14 C15 N1 111.0(3) . . ?
N1 C16 C17 130.0(3) . . ?
N1 C16 C13 107.8(3) . . ?
C17 C16 C13 122.2(3) . . ?
C18 C17 C16 117.4(3) . . ?
C17 C18 C11 122.3(3) . . ?
C23 C20 C21 111.1(4) . . ?
C23 C20 C3 124.1(3) . . ?
C21 C20 C3 124.8(3) . . ?
C22 C21 C20 112.2(7) . . ?
C20 C21 S1' 114.0(4) . . ?
C21 C22 S1 113.8(9) . . ?
C23 C22' S1' 111.7(10) . . ?
C22' C23 C20 111.7(7) . . ?
C20 C23 S1 113.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 -1.5(4) . . . . ?
C9 C1 C2 C3 -113.0(4) . . . . ?
C5 C1 C2 C11 174.8(3) . . . . ?
C9 C1 C2 C11 63.3(4) . . . . ?
C11 C2 C3 C20 5.1(7) . . . . ?
C1 C2 C3 C20 -179.0(4) . . . . ?
C11 C2 C3 C4 -174.5(4) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 O1 177.4(4) . . . . ?
C20 C3 C4 O1 -2.2(6) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C20 C3 C4 C5 179.6(3) . . . . ?
O1 C4 C5 C1 -178.4(4) . . . . ?
C3 C4 C5 C1 -0.2(4) . . . . ?
O1 C4 C5 C6 -66.9(5) . . . . ?
C3 C4 C5 C6 111.3(3) . . . . ?
C2 C1 C5 C4 0.9(4) . . . . ?
C9 C1 C5 C4 119.6(3) . . . . ?
C2 C1 C5 C6 -117.7(3) . . . . ?
C9 C1 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C7 179.0(3) . . . . ?
C1 C5 C6 C7 -68.2(3) . . . . ?
C4 C5 C6 C10 -77.2(3) . . . . ?
C1 C5 C6 C10 35.6(4) . . . . ?
C10 C6 C7 C8 -33.1(4) . . . . ?
C5 C6 C7 C8 70.9(4) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C7 C8 C9 C10 33.1(4) . . . . ?
C7 C8 C9 C1 -70.7(4) . . . . ?
C2 C1 C9 C8 179.2(3) . . . . ?
C5 C1 C9 C8 66.7(4) . . . . ?
C2 C1 C9 C10 75.6(3) . . . . ?
C5 C1 C9 C10 -36.9(3) . . . . ?
C7 C6 C10 C9 49.8(3) . . . . ?
C5 C6 C10 C9 -57.3(3) . . . . ?
C8 C9 C10 C6 -49.8(3) . . . . ?
C1 C9 C10 C6 58.0(3) . . . . ?
C3 C2 C11 C12 -151.9(4) . . . . ?
C1 C2 C11 C12 32.5(5) . . . . ?
C3 C2 C11 C18 30.8(6) . . . . ?
C1 C2 C11 C18 -144.8(4) . . . . ?
C18 C11 C12 C13 -3.3(5) . . . . ?
C2 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C13 C16 2.0(5) . . . . ?
C11 C12 C13 C14 -177.2(4) . . . . ?
C12 C13 C14 C15 178.7(4) . . . . ?
C16 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 N1 0.9(4) . . . . ?
C16 N1 C15 C14 -0.9(4) . . . . ?
C19 N1 C15 C14 -172.9(3) . . . . ?
C15 N1 C16 C17 -179.6(4) . . . . ?
C19 N1 C16 C17 -7.7(6) . . . . ?
C15 N1 C16 C13 0.5(4) . . . . ?
C19 N1 C16 C13 172.4(3) . . . . ?
C12 C13 C16 N1 -179.3(3) . . . . ?
C14 C13 C16 N1 0.1(4) . . . . ?
C12 C13 C16 C17 0.7(5) . . . . ?
C14 C13 C16 C17 -179.9(3) . . . . ?
N1 C16 C17 C18 178.0(3) . . . . ?
C13 C16 C17 C18 -2.0(5) . . . . ?
C16 C17 C18 C11 0.7(5) . . . . ?
C12 C11 C18 C17 1.9(5) . . . . ?
C2 C11 C18 C17 179.3(3) . . . . ?
C2 C3 C20 C23 -129.3(4) . . . . ?
C4 C3 C20 C23 50.3(5) . . . . ?
C2 C3 C20 C21 50.3(6) . . . . ?
C4 C3 C20 C21 -130.1(4) . . . . ?
C23 C20 C21 C22 1.3(12) . . . . ?
C3 C20 C21 C22 -178.4(11) . . . . ?
C23 C20 C21 S1' -1.1(5) . . . . ?
C3 C20 C21 S1' 179.2(4) . . . . ?
C22' S1' C21 C20 3.6(11) . . . . ?
C20 C21 C22 S1 -0.8(18) . . . . ?
C23 S1 C22 C21 0.1(15) . . . . ?
C21 S1' C22' C23 -5.1(18) . . . . ?
S1' C22' C23 C20 5(2) . . . . ?
C21 C20 C23 C22' -2.8(14) . . . . ?
C3 C20 C23 C22' 176.8(13) . . . . ?
C21 C20 C23 S1 -1.2(4) . . . . ?
C3 C20 C23 S1 178.4(3) . . . . ?
C22 S1 C23 C20 0.6(9) . . . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_TSL163_0m
_database_code_depnum_ccdc_archive 'CCDC 1483205'
_audit_update_record             
;
2016-06-02 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 B O3'
_chemical_formula_weight         348.23
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_space_group_IT_number           2
_symmetry_space_group_name_H-M   P-1
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7865(5)
_cell_length_b                   12.5627(6)
_cell_length_c                   16.1123(7)
_cell_angle_alpha                90.4912(14)
_cell_angle_beta                 102.2018(14)
_cell_angle_gamma                93.6195(14)
_cell_volume                     1931.82(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      31.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            28656
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.054
_diffrn_reflns_theta_max         31.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             12256
_reflns_number_gt                9722
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0677P)²+0.5554P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12256
_refine_ls_number_parameters     553
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1A B 0.88181(13) 0.67054(9) 0.12278(7) 0.0160(2) Uani 1 1 d . . . . .
O1A O 0.70620(10) 0.59493(7) 0.38609(5) 0.0277(2) Uani 1 1 d . . . . .
O2A O 0.83483(8) 0.76297(6) 0.08730(5) 0.01709(15) Uani 1 1 d . . . . .
O3A O 0.97751(9) 0.62544(6) 0.08520(5) 0.01951(16) Uani 1 1 d . . . . .
C1A C 0.73687(12) 0.57982(9) 0.31769(6) 0.0182(2) Uani 1 1 d . . . . .
C2A C 0.82712(11) 0.65266(8) 0.27569(6) 0.01598(19) Uani 1 1 d . . . . .
C3A C 0.82284(11) 0.61513(8) 0.19595(6) 0.01614(19) Uani 1 1 d . . . . .
C4A C 0.74280(12) 0.50739(8) 0.17842(6) 0.01697(19) Uani 1 1 d . . . . .
H4A H 0.8053 0.4511 0.1679 0.020 Uiso 1 1 calc R U . . .
C5A C 0.60737(13) 0.50632(9) 0.10634(7) 0.0210(2) Uani 1 1 d . . . . .
H5A H 0.6185 0.5391 0.0516 0.025 Uiso 1 1 calc R U . . .
C6A C 0.54655(14) 0.39129(10) 0.10068(7) 0.0255(2) Uani 1 1 d . . . . .
H6A H 0.5447 0.3415 0.0557 0.031 Uiso 1 1 calc R U . . .
C7A C 0.49629(13) 0.37318(10) 0.17046(7) 0.0249(2) Uani 1 1 d . . . . .
H7A H 0.4521 0.3081 0.1841 0.030 Uiso 1 1 calc R U . . .
C8A C 0.52248(12) 0.47541(10) 0.22410(7) 0.0217(2) Uani 1 1 d . . . . .
H8A H 0.4630 0.4827 0.2670 0.026 Uiso 1 1 calc R U . . .
C9A C 0.68427(12) 0.48427(9) 0.25899(6) 0.01760(19) Uani 1 1 d . . . . .
H9A H 0.7178 0.4165 0.2857 0.021 Uiso 1 1 calc R U . . .
C10A C 0.50685(13) 0.55898(10) 0.15346(7) 0.0242(2) Uani 1 1 d . . . . .
H10A H 0.4101 0.5591 0.1192 0.029 Uiso 1 1 calc R U . . .
H10B H 0.5412 0.6319 0.1752 0.029 Uiso 1 1 calc R U . . .
C11A C 0.90240(11) 0.75207(8) 0.31488(6) 0.01652(19) Uani 1 1 d . . . . .
C12A C 0.85048(12) 0.81201(9) 0.37359(7) 0.0195(2) Uani 1 1 d . . . . .
H12A H 0.7695 0.7856 0.3925 0.023 Uiso 1 1 calc R U . . .
C13A C 0.91666(13) 0.91000(10) 0.40443(7) 0.0229(2) Uani 1 1 d . . . . .
H13A H 0.8802 0.9502 0.4440 0.028 Uiso 1 1 calc R U . . .
C14A C 1.03561(13) 0.94933(10) 0.37780(7) 0.0246(2) Uani 1 1 d . . . . .
H14A H 1.0791 1.0171 0.3979 0.030 Uiso 1 1 calc R U . . .
C15A C 1.09076(12) 0.88899(10) 0.32158(8) 0.0247(2) Uani 1 1 d . . . . .
H15A H 1.1730 0.9151 0.3038 0.030 Uiso 1 1 calc R U . . .
C16A C 1.02602(12) 0.79073(9) 0.29134(7) 0.0207(2) Uani 1 1 d . . . . .
H16A H 1.0659 0.7491 0.2542 0.025 Uiso 1 1 calc R U . . .
C17A C 0.92140(11) 0.79296(8) 0.02548(7) 0.01601(19) Uani 1 1 d . . . . .
C18A C 0.98021(11) 0.68441(8) 0.00686(6) 0.01645(19) Uani 1 1 d . . . . .
C19A C 1.03390(13) 0.87554(9) 0.06949(8) 0.0233(2) Uani 1 1 d . . . . .
H19A H 0.9897 0.9357 0.0897 0.035 Uiso 1 1 calc R U . . .
H19B H 1.0905 0.9010 0.0293 0.035 Uiso 1 1 calc R U . . .
H19C H 1.0941 0.8432 0.1178 0.035 Uiso 1 1 calc R U . . .
C20A C 0.82772(12) 0.83988(9) -0.05103(7) 0.0209(2) Uani 1 1 d . . . . .
H20A H 0.7457 0.7905 -0.0717 0.031 Uiso 1 1 calc R U . . .
H20B H 0.8801 0.8512 -0.0961 0.031 Uiso 1 1 calc R U . . .
H20C H 0.7969 0.9082 -0.0346 0.031 Uiso 1 1 calc R U . . .
C21A C 1.12978(12) 0.69258(10) -0.00633(8) 0.0236(2) Uani 1 1 d . . . . .
H21A H 1.1927 0.7230 0.0451 0.035 Uiso 1 1 calc R U . . .
H21B H 1.1356 0.7387 -0.0544 0.035 Uiso 1 1 calc R U . . .
H21C H 1.1575 0.6214 -0.0182 0.035 Uiso 1 1 calc R U . . .
C22A C 0.88403(13) 0.61947(9) -0.06494(7) 0.0216(2) Uani 1 1 d . . . . .
H22A H 0.9189 0.5485 -0.0683 0.032 Uiso 1 1 calc R U . . .
H22B H 0.8821 0.6557 -0.1188 0.032 Uiso 1 1 calc R U . . .
H22C H 0.7892 0.6124 -0.0540 0.032 Uiso 1 1 calc R U . . .
B1B B 0.62945(12) 0.16674(10) 0.37519(7) 0.0161(2) Uani 1 1 d . . . . .
O1B O 0.93380(10) 0.10046(7) 0.17203(6) 0.0280(2) Uani 1 1 d . . . . .
C1B C 0.84573(11) 0.08263(9) 0.21439(7) 0.0179(2) Uani 1 1 d . . . . .
C2B C 0.82172(11) 0.15054(8) 0.28572(6) 0.01594(19) Uani 1 1 d . . . . .
C3B C 0.70335(11) 0.11328(8) 0.30970(6) 0.01580(19) Uani 1 1 d . . . . .
C4B C 0.64027(11) 0.01125(9) 0.26230(7) 0.0179(2) Uani 1 1 d . . . . .
H4B H 0.6360 -0.0490 0.3020 0.021 Uiso 1 1 calc R U . . .
C5B C 0.49480(12) 0.02220(11) 0.20049(8) 0.0275(3) Uani 1 1 d . . . . .
H5B H 0.4228 0.0579 0.2246 0.033 Uiso 1 1 calc R U . . .
C6B C 0.45240(14) -0.08988(12) 0.16255(9) 0.0343(3) Uani 1 1 d . . . . .
H6B H 0.3793 -0.1370 0.1742 0.041 Uiso 1 1 calc R U . . .
C7B C 0.53708(14) -0.10929(12) 0.11012(9) 0.0316(3) Uani 1 1 d . . . . .
H7B H 0.5354 -0.1731 0.0777 0.038 Uiso 1 1 calc R U . . .
C8B C 0.63619(13) -0.01183(10) 0.11136(7) 0.0236(2) Uani 1 1 d . . . . .
H8B H 0.6816 -0.0041 0.0615 0.028 Uiso 1 1 calc R U . . .
C9B C 0.73724(11) -0.01075(9) 0.20044(6) 0.01728(19) Uani 1 1 d . . . . .
H9B H 0.7814 -0.0802 0.2120 0.021 Uiso 1 1 calc R U . . .
C10B C 0.54125(14) 0.07704(11) 0.12503(8) 0.0288(3) Uani 1 1 d . . . . .
H10C H 0.5937 0.1468 0.1409 0.035 Uiso 1 1 calc R U . . .
H10D H 0.4627 0.0847 0.0759 0.035 Uiso 1 1 calc R U . . .
C11B C 0.91321(11) 0.24482(9) 0.32063(7) 0.01699(19) Uani 1 1 d . . . . .
C12B C 0.97095(12) 0.31394(9) 0.26762(7) 0.0208(2) Uani 1 1 d . . . . .
H12B H 0.9571 0.2970 0.2087 0.025 Uiso 1 1 calc R U . . .
C13B C 1.04829(13) 0.40701(10) 0.30016(8) 0.0264(2) Uani 1 1 d . . . . .
H13B H 1.0858 0.4539 0.2634 0.032 Uiso 1 1 calc R U . . .
C14B C 1.07098(13) 0.43175(11) 0.38669(9) 0.0297(3) Uani 1 1 d . . . . .
H14B H 1.1217 0.4964 0.4088 0.036 Uiso 1 1 calc R U . . .
C15B C 1.01909(13) 0.36147(11) 0.44044(8) 0.0284(3) Uani 1 1 d . . . . .
H15B H 1.0370 0.3771 0.4997 0.034 Uiso 1 1 calc R U . . .
C16B C 0.94133(12) 0.26865(10) 0.40796(7) 0.0222(2) Uani 1 1 d . . . . .
H16B H 0.9068 0.2208 0.4452 0.027 Uiso 1 1 calc R U . . .
O2B O 0.59052(12) 0.26917(8) 0.36933(6) 0.0178(2) Uani 0.85 1 d D U P A 1
O3B O 0.59269(13) 0.11203(9) 0.44100(8) 0.0192(2) Uani 0.85 1 d D U P A 1
C17B C 0.54119(14) 0.29292(10) 0.44712(8) 0.0167(2) Uani 0.85 1 d D U P A 1
C18B C 0.50040(13) 0.17948(10) 0.47626(8) 0.0170(2) Uani 0.85 1 d D U P A 1
C19B C 0.4201(4) 0.3650(2) 0.4259(3) 0.0285(8) Uani 0.85 1 d D U P A 1
H19D H 0.4548 0.4353 0.4105 0.043 Uiso 0.85 1 calc R U P A 1
H19E H 0.3778 0.3724 0.4755 0.043 Uiso 0.85 1 calc R U P A 1
H19F H 0.3496 0.3336 0.3781 0.043 Uiso 0.85 1 calc R U P A 1
C20B C 0.66464(18) 0.35015(14) 0.50815(11) 0.0252(3) Uani 0.85 1 d D U P A 1
H20D H 0.7405 0.3019 0.5230 0.038 Uiso 0.85 1 calc R U P A 1
H20E H 0.6349 0.3721 0.5598 0.038 Uiso 0.85 1 calc R U P A 1
H20F H 0.6979 0.4133 0.4810 0.038 Uiso 0.85 1 calc R U P A 1
C21B C 0.35152(17) 0.13833(16) 0.43668(11) 0.0282(3) Uani 0.85 1 d D U P A 1
H21D H 0.3350 0.1453 0.3749 0.042 Uiso 0.85 1 calc R U P A 1
H21E H 0.2855 0.1800 0.4591 0.042 Uiso 0.85 1 calc R U P A 1
H21F H 0.3379 0.0631 0.4505 0.042 Uiso 0.85 1 calc R U P A 1
C22B C 0.5296(5) 0.1679(3) 0.57260(19) 0.0246(7) Uani 0.85 1 d D U P A 1
H22D H 0.5010 0.0951 0.5862 0.037 Uiso 0.85 1 calc R U P A 1
H22E H 0.4766 0.2187 0.5973 0.037 Uiso 0.85 1 calc R U P A 1
H22F H 0.6300 0.1824 0.5960 0.037 Uiso 0.85 1 calc R U P A 1
O2B' O 0.5311(7) 0.2402(5) 0.3511(4) 0.0219(12) Uani 0.15 1 d D U P A 2
O3B' O 0.6477(7) 0.1415(5) 0.4581(4) 0.0222(12) Uani 0.15 1 d D U P A 2
C17' C 0.4628(6) 0.2541(5) 0.4232(4) 0.0236(13) Uani 0.15 1 d D U P A 2
C18' C 0.5769(7) 0.2209(5) 0.4988(4) 0.0248(14) Uani 0.15 1 d D U P A 2
C19' C 0.3285(8) 0.1808(8) 0.4064(6) 0.0275(17) Uani 0.15 1 d D U P A 2
H19G H 0.2727 0.1942 0.3499 0.041 Uiso 0.15 1 calc R U P A 2
H19H H 0.2741 0.1949 0.4494 0.041 Uiso 0.15 1 calc R U P A 2
H19I H 0.3527 0.1062 0.4092 0.041 Uiso 0.15 1 calc R U P A 2
C20' C 0.435(2) 0.3716(8) 0.4261(14) 0.024(3) Uani 0.15 1 d D U P A 2
H20G H 0.5227 0.4150 0.4292 0.036 Uiso 0.15 1 calc R U P A 2
H20H H 0.3969 0.3866 0.4762 0.036 Uiso 0.15 1 calc R U P A 2
H20I H 0.3672 0.3888 0.3747 0.036 Uiso 0.15 1 calc R U P A 2
C21' C 0.521(3) 0.1601(18) 0.5671(12) 0.031(4) Uani 0.15 1 d D U P A 2
H21G H 0.4504 0.1043 0.5404 0.047 Uiso 0.15 1 calc R U P A 2
H21H H 0.4781 0.2094 0.6000 0.047 Uiso 0.15 1 calc R U P A 2
H21I H 0.5980 0.1274 0.6050 0.047 Uiso 0.15 1 calc R U P A 2
C22' C 0.6873(10) 0.3115(7) 0.5345(6) 0.0295(19) Uani 0.15 1 d D U P A 2
H22G H 0.7683 0.2816 0.5710 0.044 Uiso 0.15 1 calc R U P A 2
H22H H 0.6467 0.3618 0.5677 0.044 Uiso 0.15 1 calc R U P A 2
H22I H 0.7172 0.3487 0.4875 0.044 Uiso 0.15 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
B1A O2A 1.3617(14) . ?
B1A O3A 1.3658(13) . ?
B1A C3A 1.5680(15) . ?
O1A C1A 1.2182(13) . ?
O2A C17A 1.4747(12) . ?
O3A C18A 1.4734(12) . ?
C1A C2A 1.4956(15) . ?
C1A C9A 1.5156(15) . ?
C2A C3A 1.3561(14) . ?
C2A C11A 1.4747(15) . ?
C3A C4A 1.5137(15) . ?
C4A C9A 1.5484(14) . ?
C4A C5A 1.5660(15) . ?
C5A C6A 1.5222(16) . ?
C5A C10A 1.5398(17) . ?
C6A C7A 1.3347(18) . ?
C7A C8A 1.5191(17) . ?
C8A C10A 1.5455(16) . ?
C8A C9A 1.5607(16) . ?
C11A C12A 1.3996(15) . ?
C11A C16A 1.4023(16) . ?
C12A C13A 1.3908(16) . ?
C13A C14A 1.3876(18) . ?
C14A C15A 1.3903(18) . ?
C15A C16A 1.3868(17) . ?
C17A C19A 1.5181(16) . ?
C17A C20A 1.5200(15) . ?
C17A C18A 1.5639(14) . ?
C18A C21A 1.5202(15) . ?
C18A C22A 1.5219(16) . ?
B1B O3B' 1.354(6) . ?
B1B O2B 1.3633(16) . ?
B1B O3B 1.3670(16) . ?
B1B O2B' 1.374(6) . ?
B1B C3B 1.5682(15) . ?
O1B C1B 1.2189(13) . ?
C1B C2B 1.4921(14) . ?
C1B C9B 1.5137(16) . ?
C2B C3B 1.3544(15) . ?
C2B C11B 1.4706(15) . ?
C3B C4B 1.5137(15) . ?
C4B C9B 1.5487(14) . ?
C4B C5B 1.5701(16) . ?
C5B C6B 1.5274(19) . ?
C5B C10B 1.539(2) . ?
C6B C7B 1.3334(19) . ?
C7B C8B 1.5105(19) . ?
C8B C10B 1.5400(17) . ?
C8B C9B 1.5608(15) . ?
C11B C12B 1.3992(16) . ?
C11B C16B 1.4015(15) . ?
C12B C13B 1.3875(17) . ?
C13B C14B 1.3937(18) . ?
C14B C15B 1.389(2) . ?
C15B C16B 1.3863(18) . ?
O2B C17B 1.4700(14) . ?
O3B C18B 1.4703(15) . ?
C17B C19B 1.520(3) . ?
C17B C20B 1.523(2) . ?
C17B C18B 1.5587(18) . ?
C18B C21B 1.518(2) . ?
C18B C22B 1.528(3) . ?
O2B' C17' 1.471(7) . ?
O3B' C18' 1.475(7) . ?
C17' C20' 1.520(7) . ?
C17' C19' 1.530(6) . ?
C17' C18' 1.548(7) . ?
C18' C21' 1.521(7) . ?
C18' C22' 1.537(6) . ?

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
O2A B1A O3A 114.45(9) . . ?
O2A B1A C3A 123.07(9) . . ?
O3A B1A C3A 122.30(9) . . ?
B1A O2A C17A 106.89(8) . . ?
B1A O3A C18A 106.67(8) . . ?
O1A C1A C2A 126.61(10) . . ?
O1A C1A C9A 125.02(10) . . ?
C2A C1A C9A 108.33(9) . . ?
C3A C2A C11A 126.30(10) . . ?
C3A C2A C1A 109.31(9) . . ?
C11A C2A C1A 124.32(9) . . ?
C2A C3A C4A 112.21(9) . . ?
C2A C3A B1A 128.73(10) . . ?
C4A C3A B1A 118.99(9) . . ?
C3A C4A C9A 105.00(8) . . ?
C3A C4A C5A 114.57(9) . . ?
C9A C4A C5A 103.09(9) . . ?
C6A C5A C10A 100.27(10) . . ?
C6A C5A C4A 104.75(9) . . ?
C10A C5A C4A 100.65(8) . . ?
C7A C6A C5A 107.51(10) . . ?
C6A C7A C8A 107.67(11) . . ?
C7A C8A C10A 100.18(9) . . ?
C7A C8A C9A 104.11(9) . . ?
C10A C8A C9A 101.33(9) . . ?
C1A C9A C4A 104.80(9) . . ?
C1A C9A C8A 114.27(9) . . ?
C4A C9A C8A 102.97(8) . . ?
C5A C10A C8A 93.85(9) . . ?
C12A C11A C16A 118.41(10) . . ?
C12A C11A C2A 121.38(10) . . ?
C16A C11A C2A 120.17(9) . . ?
C13A C12A C11A 120.48(11) . . ?
C14A C13A C12A 120.41(11) . . ?
C13A C14A C15A 119.65(11) . . ?
C16A C15A C14A 120.15(11) . . ?
C15A C16A C11A 120.80(11) . . ?
O2A C17A C19A 106.80(8) . . ?
O2A C17A C20A 108.20(8) . . ?
C19A C17A C20A 110.85(9) . . ?
O2A C17A C18A 102.42(8) . . ?
C19A C17A C18A 113.38(9) . . ?
C20A C17A C18A 114.43(9) . . ?
O3A C18A C21A 108.44(9) . . ?
O3A C18A C22A 106.32(9) . . ?
C21A C18A C22A 110.73(9) . . ?
O3A C18A C17A 102.50(7) . . ?
C21A C18A C17A 115.00(9) . . ?
C22A C18A C17A 113.05(9) . . ?
O2B B1B O3B 114.37(10) . . ?
O3B' B1B O2B' 113.4(3) . . ?
O3B' B1B C3B 124.6(2) . . ?
O2B B1B C3B 123.32(10) . . ?
O3B B1B C3B 122.24(10) . . ?
O2B' B1B C3B 121.9(2) . . ?
O1B C1B C2B 126.40(11) . . ?
O1B C1B C9B 125.23(10) . . ?
C2B C1B C9B 108.32(9) . . ?
C3B C2B C11B 126.99(9) . . ?
C3B C2B C1B 109.51(9) . . ?
C11B C2B C1B 123.48(9) . . ?
C2B C3B C4B 112.14(9) . . ?
C2B C3B B1B 127.01(10) . . ?
C4B C3B B1B 120.81(9) . . ?
C3B C4B C9B 104.98(9) . . ?
C3B C4B C5B 114.44(9) . . ?
C9B C4B C5B 102.61(8) . . ?
C6B C5B C10B 100.19(10) . . ?
C6B C5B C4B 104.50(10) . . ?
C10B C5B C4B 100.82(9) . . ?
C7B C6B C5B 107.27(12) . . ?
C6B C7B C8B 107.86(11) . . ?
C7B C8B C10B 100.65(10) . . ?
C7B C8B C9B 105.09(10) . . ?
C10B C8B C9B 100.41(9) . . ?
C1B C9B C4B 104.75(8) . . ?
C1B C9B C8B 113.20(9) . . ?
C4B C9B C8B 103.28(9) . . ?
C5B C10B C8B 93.92(10) . . ?
C12B C11B C16B 118.61(11) . . ?
C12B C11B C2B 121.06(10) . . ?
C16B C11B C2B 120.31(10) . . ?
C13B C12B C11B 120.68(11) . . ?
C12B C13B C14B 120.05(12) . . ?
C15B C14B C13B 119.72(12) . . ?
C16B C15B C14B 120.27(11) . . ?
C15B C16B C11B 120.57(11) . . ?
B1B O2B C17B 106.63(9) . . ?
B1B O3B C18B 106.37(10) . . ?
O2B C17B C19B 109.19(19) . . ?
O2B C17B C20B 106.42(11) . . ?
C19B C17B C20B 110.33(19) . . ?
O2B C17B C18B 102.30(9) . . ?
C19B C17B C18B 114.43(19) . . ?
C20B C17B C18B 113.49(12) . . ?
O3B C18B C21B 106.25(11) . . ?
O3B C18B C22B 108.91(19) . . ?
C21B C18B C22B 110.53(19) . . ?
O3B C18B C17B 102.57(9) . . ?
C21B C18B C17B 113.94(13) . . ?
C22B C18B C17B 113.94(18) . . ?
B1B O2B' C17' 106.5(4) . . ?
B1B O3B' C18' 106.6(5) . . ?
O2B' C17' C20' 106.0(9) . . ?
O2B' C17' C19' 107.4(6) . . ?
C20' C17' C19' 112.9(10) . . ?
O2B' C17' C18' 101.8(5) . . ?
C20' C17' C18' 113.2(9) . . ?
C19' C17' C18' 114.2(6) . . ?
O3B' C18' C21' 104.8(10) . . ?
O3B' C18' C22' 107.1(6) . . ?
C21' C18' C22' 113.4(11) . . ?
O3B' C18' C17' 101.7(5) . . ?
C21' C18' C17' 114.6(10) . . ?
C22' C18' C17' 113.7(6) . . ?

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
O3A B1A O2A C17A -8.29(12) . . . . ?
C3A B1A O2A C17A 176.35(10) . . . . ?
O2A B1A O3A C18A -9.72(12) . . . . ?
C3A B1A O3A C18A 165.68(10) . . . . ?
O1A C1A C2A C3A -172.44(12) . . . . ?
C9A C1A C2A C3A 5.47(12) . . . . ?
O1A C1A C2A C11A 4.86(18) . . . . ?
C9A C1A C2A C11A -177.23(9) . . . . ?
C11A C2A C3A C4A 176.58(10) . . . . ?
C1A C2A C3A C4A -6.19(12) . . . . ?
C11A C2A C3A B1A -6.65(18) . . . . ?
C1A C2A C3A B1A 170.58(10) . . . . ?
O2A B1A C3A C2A -62.67(17) . . . . ?
O3A B1A C3A C2A 122.33(13) . . . . ?
O2A B1A C3A C4A 113.92(12) . . . . ?
O3A B1A C3A C4A -61.08(14) . . . . ?
C2A C3A C4A C9A 4.43(12) . . . . ?
B1A C3A C4A C9A -172.69(9) . . . . ?
C2A C3A C4A C5A 116.78(10) . . . . ?
B1A C3A C4A C5A -60.34(13) . . . . ?
C3A C4A C5A C6A 179.95(9) . . . . ?
C9A C4A C5A C6A -66.56(11) . . . . ?
C3A C4A C5A C10A -76.33(11) . . . . ?
C9A C4A C5A C10A 37.16(10) . . . . ?
C10A C5A C6A C7A -33.34(12) . . . . ?
C4A C5A C6A C7A 70.67(12) . . . . ?
C5A C6A C7A C8A -0.04(14) . . . . ?
C6A C7A C8A C10A 33.25(13) . . . . ?
C6A C7A C8A C9A -71.28(12) . . . . ?
O1A C1A C9A C4A 175.39(11) . . . . ?
C2A C1A C9A C4A -2.56(11) . . . . ?
O1A C1A C9A C8A 63.43(15) . . . . ?
C2A C1A C9A C8A -114.52(10) . . . . ?
C3A C4A C9A C1A -0.84(11) . . . . ?
C5A C4A C9A C1A -121.12(9) . . . . ?
C3A C4A C9A C8A 118.98(9) . . . . ?
C5A C4A C9A C8A -1.30(10) . . . . ?
C7A C8A C9A C1A -178.17(9) . . . . ?
C10A C8A C9A C1A 78.17(11) . . . . ?
C7A C8A C9A C4A 68.78(10) . . . . ?
C10A C8A C9A C4A -34.88(10) . . . . ?
C6A C5A C10A C8A 50.00(10) . . . . ?
C4A C5A C10A C8A -57.29(9) . . . . ?
C7A C8A C10A C5A -50.03(10) . . . . ?
C9A C8A C10A C5A 56.74(10) . . . . ?
C3A C2A C11A C12A 146.93(11) . . . . ?
C1A C2A C11A C12A -29.91(16) . . . . ?
C3A C2A C11A C16A -30.68(16) . . . . ?
C1A C2A C11A C16A 152.49(11) . . . . ?
C16A C11A C12A C13A 3.07(16) . . . . ?
C2A C11A C12A C13A -174.58(10) . . . . ?
C11A C12A C13A C14A -0.40(17) . . . . ?
C12A C13A C14A C15A -1.63(18) . . . . ?
C13A C14A C15A C16A 0.94(18) . . . . ?
C14A C15A C16A C11A 1.81(18) . . . . ?
C12A C11A C16A C15A -3.77(16) . . . . ?
C2A C11A C16A C15A 173.90(10) . . . . ?
B1A O2A C17A C19A -98.16(10) . . . . ?
B1A O2A C17A C20A 142.46(9) . . . . ?
B1A O2A C17A C18A 21.25(10) . . . . ?
B1A O3A C18A C21A 144.07(9) . . . . ?
B1A O3A C18A C22A -96.82(10) . . . . ?
B1A O3A C18A C17A 22.05(11) . . . . ?
O2A C17A C18A O3A -26.01(10) . . . . ?
C19A C17A C18A O3A 88.68(10) . . . . ?
C20A C17A C18A O3A -142.84(9) . . . . ?
O2A C17A C18A C21A -143.45(9) . . . . ?
C19A C17A C18A C21A -28.76(13) . . . . ?
C20A C17A C18A C21A 99.72(11) . . . . ?
O2A C17A C18A C22A 88.02(10) . . . . ?
C19A C17A C18A C22A -157.30(9) . . . . ?
C20A C17A C18A C22A -28.82(13) . . . . ?
O1B C1B C2B C3B 171.61(11) . . . . ?
C9B C1B C2B C3B -5.87(12) . . . . ?
O1B C1B C2B C11B -6.61(17) . . . . ?
C9B C1B C2B C11B 175.91(9) . . . . ?
C11B C2B C3B C4B -177.35(10) . . . . ?
C1B C2B C3B C4B 4.51(12) . . . . ?
C11B C2B C3B B1B 5.23(18) . . . . ?
C1B C2B C3B B1B -172.92(10) . . . . ?
O3B' B1B C3B C2B -96.3(4) . . . . ?
O2B B1B C3B C2B 54.14(17) . . . . ?
O3B B1B C3B C2B -129.09(13) . . . . ?
O2B' B1B C3B C2B 88.2(4) . . . . ?
O3B' B1B C3B C4B 86.5(4) . . . . ?
O2B B1B C3B C4B -123.09(12) . . . . ?
O3B B1B C3B C4B 53.69(15) . . . . ?
O2B' B1B C3B C4B -89.1(4) . . . . ?
C2B C3B C4B C9B -1.42(12) . . . . ?
B1B C3B C4B C9B 176.19(9) . . . . ?
C2B C3B C4B C5B -113.13(11) . . . . ?
B1B C3B C4B C5B 64.48(13) . . . . ?
C3B C4B C5B C6B -178.76(10) . . . . ?
C9B C4B C5B C6B 68.12(12) . . . . ?
C3B C4B C5B C10B 77.62(11) . . . . ?
C9B C4B C5B C10B -35.50(11) . . . . ?
C10B C5B C6B C7B 33.33(14) . . . . ?
C4B C5B C6B C7B -70.77(14) . . . . ?
C5B C6B C7B C8B -0.30(16) . . . . ?
C6B C7B C8B C10B -32.86(14) . . . . ?
C6B C7B C8B C9B 71.09(14) . . . . ?
O1B C1B C9B C4B -172.78(11) . . . . ?
C2B C1B C9B C4B 4.73(11) . . . . ?
O1B C1B C9B C8B -60.98(15) . . . . ?
C2B C1B C9B C8B 116.53(10) . . . . ?
C3B C4B C9B C1B -2.16(11) . . . . ?
C5B C4B C9B C1B 117.76(10) . . . . ?
C3B C4B C9B C8B -120.89(9) . . . . ?
C5B C4B C9B C8B -0.97(11) . . . . ?
C7B C8B C9B C1B -179.77(9) . . . . ?
C10B C8B C9B C1B -75.63(11) . . . . ?
C7B C8B C9B C4B -67.07(11) . . . . ?
C10B C8B C9B C4B 37.07(11) . . . . ?
C6B C5B C10B C8B -49.65(11) . . . . ?
C4B C5B C10B C8B 57.40(10) . . . . ?
C7B C8B C10B C5B 49.76(10) . . . . ?
C9B C8B C10B C5B -57.93(10) . . . . ?
C3B C2B C11B C12B -139.39(12) . . . . ?
C1B C2B C11B C12B 38.51(15) . . . . ?
C3B C2B C11B C16B 38.94(16) . . . . ?
C1B C2B C11B C16B -143.16(11) . . . . ?
C16B C11B C12B C13B -3.34(17) . . . . ?
C2B C11B C12B C13B 175.02(10) . . . . ?
C11B C12B C13B C14B 0.97(18) . . . . ?
C12B C13B C14B C15B 1.73(19) . . . . ?
C13B C14B C15B C16B -1.99(19) . . . . ?
C14B C15B C16B C11B -0.45(18) . . . . ?
C12B C11B C16B C15B 3.08(17) . . . . ?
C2B C11B C16B C15B -175.29(10) . . . . ?
O3B B1B O2B C17B 9.67(15) . . . . ?
C3B B1B O2B C17B -173.33(10) . . . . ?
O2B B1B O3B C18B 9.16(15) . . . . ?
C3B B1B O3B C18B -167.88(10) . . . . ?
B1B O2B C17B C19B -144.4(2) . . . . ?
B1B O2B C17B C20B 96.51(13) . . . . ?
B1B O2B C17B C18B -22.81(13) . . . . ?
B1B O3B C18B C21B 97.32(13) . . . . ?
B1B O3B C18B C22B -143.60(19) . . . . ?
B1B O3B C18B C17B -22.55(13) . . . . ?
O2B C17B C18B O3B 27.35(13) . . . . ?
C19B C17B C18B O3B 145.3(2) . . . . ?
C20B C17B C18B O3B -86.88(13) . . . . ?
O2B C17B C18B C21B -87.03(13) . . . . ?
C19B C17B C18B C21B 30.9(2) . . . . ?
C20B C17B C18B C21B 158.75(12) . . . . ?
O2B C17B C18B C22B 144.9(2) . . . . ?
C19B C17B C18B C22B -97.2(3) . . . . ?
C20B C17B C18B C22B 30.7(2) . . . . ?
O3B' B1B O2B' C17' -8.5(7) . . . . ?
C3B B1B O2B' C17' 167.5(3) . . . . ?
O2B' B1B O3B' C18' -12.5(7) . . . . ?
C3B B1B O3B' C18' 171.6(3) . . . . ?
B1B O2B' C17' C20' 143.1(10) . . . . ?
B1B O2B' C17' C19' -95.9(7) . . . . ?
B1B O2B' C17' C18' 24.4(6) . . . . ?
B1B O3B' C18' C21' 146.4(11) . . . . ?
B1B O3B' C18' C22' -92.9(7) . . . . ?
B1B O3B' C18' C17' 26.7(7) . . . . ?
O2B' C17' C18' O3B' -30.6(6) . . . . ?
C20' C17' C18' O3B' -144.0(10) . . . . ?
C19' C17' C18' O3B' 84.8(7) . . . . ?
O2B' C17' C18' C21' -143.0(11) . . . . ?
C20' C17' C18' C21' 103.6(14) . . . . ?
C19' C17' C18' C21' -27.6(12) . . . . ?
O2B' C17' C18' C22' 84.3(7) . . . . ?
C20' C17' C18' C22' -29.1(12) . . . . ?
C19' C17' C18' C22' -160.3(7) . . . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_TSL2-3
_database_code_depnum_ccdc_archive 'CCDC 1483206'
_audit_update_record             
;
2016-06-02 deposited with the CCDC.
2016-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 B N2 O'
_chemical_formula_weight         388.26
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'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_H-M   P2(1)/c
_space_group_name_Hall           '-P 2ybc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.3909(10)
_cell_length_b                   10.1233(4)
_cell_length_c                   20.4987(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.235(4)
_cell_angle_gamma                90
_cell_volume                     4007.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8775
_cell_measurement_theta_min      1.9970
_cell_measurement_theta_max      29.9290

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
; 
 CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            40608
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.995
_diffrn_reflns_theta_max         30.535
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             10796
_reflns_number_gt                7349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²+4.3639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10796
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.1958
_refine_ls_wR_factor_gt          0.1782
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1A B 0.65840(15) 0.7916(2) 0.73475(12) 0.0220(5) Uani 1 1 d . . . . .
N1A N 0.71738(10) 0.78675(19) 0.69927(9) 0.0242(4) Uani 1 1 d . . . . .
H1AN H 0.7203 0.7234 0.6703 0.029 Uiso 1 1 calc R U . . .
N2A N 0.65486(10) 0.89552(18) 0.78128(9) 0.0216(4) Uani 1 1 d . . . . .
H2AN H 0.6175 0.9028 0.8024 0.026 Uiso 1 1 calc R U . . .
O1A O 0.47511(9) 0.46610(17) 0.65898(8) 0.0292(4) Uani 1 1 d . . . . .
C1A C 0.77125(13) 0.8780(2) 0.70819(11) 0.0239(5) Uani 1 1 d . . . . .
C2A C 0.82739(14) 0.8757(2) 0.67150(12) 0.0305(5) Uani 1 1 d . . . . .
H2A H 0.8297 0.8113 0.6381 0.037 Uiso 1 1 calc R U . . .
C3A C 0.88086(14) 0.9671(3) 0.68315(13) 0.0344(6) Uani 1 1 d . . . . .
H3A H 0.9189 0.9646 0.6571 0.041 Uiso 1 1 calc R U . . .
C4A C 0.87967(14) 1.0607(3) 0.73159(13) 0.0328(6) Uani 1 1 d . . . . .
H4A H 0.9172 1.1207 0.7393 0.039 Uiso 1 1 calc R U . . .
C5A C 0.82282(13) 1.0679(2) 0.77000(12) 0.0271(5) Uani 1 1 d . . . . .
C6A C 0.81841(14) 1.1642(2) 0.82022(13) 0.0310(6) Uani 1 1 d . . . . .
H6A H 0.8552 1.2252 0.8296 0.037 Uiso 1 1 calc R U . . .
C7A C 0.76159(14) 1.1691(2) 0.85480(13) 0.0313(6) Uani 1 1 d . . . . .
H7A H 0.7597 1.2338 0.8881 0.038 Uiso 1 1 calc R U . . .
C8A C 0.70582(14) 1.0814(2) 0.84262(11) 0.0267(5) Uani 1 1 d . . . . .
H8A H 0.6667 1.0875 0.8672 0.032 Uiso 1 1 calc R U . . .
C9A C 0.70835(12) 0.9859(2) 0.79444(11) 0.0218(5) Uani 1 1 d . . . . .
C10A C 0.76702(13) 0.9774(2) 0.75758(11) 0.0234(5) Uani 1 1 d . . . . .
C11A C 0.60122(12) 0.6819(2) 0.72915(10) 0.0204(4) Uani 1 1 d . . . . .
C12A C 0.58750(12) 0.6071(2) 0.79035(10) 0.0224(5) Uani 1 1 d . . . . .
H12A H 0.5689 0.6653 0.8240 0.027 Uiso 1 1 calc R U . . .
C13A C 0.65379(13) 0.5285(2) 0.81835(11) 0.0247(5) Uani 1 1 d . . . . .
H13A H 0.6977 0.5806 0.8253 0.030 Uiso 1 1 calc R U . . .
C14A C 0.63281(14) 0.4519(2) 0.87720(12) 0.0289(5) Uani 1 1 d . . . . .
H14A H 0.6478 0.4691 0.9218 0.035 Uiso 1 1 calc R U . . .
C15A C 0.58973(14) 0.3567(2) 0.85500(11) 0.0282(5) Uani 1 1 d . . . . .
H15A H 0.5686 0.2931 0.8809 0.034 Uiso 1 1 calc R U . . .
C16A C 0.58042(14) 0.3677(2) 0.78069(11) 0.0265(5) Uani 1 1 d . . . . .
H16A H 0.5634 0.2866 0.7565 0.032 Uiso 1 1 calc R U . . .
C17A C 0.53622(13) 0.4960(2) 0.76684(10) 0.0226(5) Uani 1 1 d . . . . .
H17A H 0.4937 0.4965 0.7911 0.027 Uiso 1 1 calc R U . . .
C18A C 0.65307(13) 0.4159(2) 0.76761(11) 0.0268(5) Uani 1 1 d . . . . .
H18A H 0.6554 0.4483 0.7223 0.032 Uiso 1 1 calc R U . . .
H18B H 0.6895 0.3490 0.7786 0.032 Uiso 1 1 calc R U . . .
C19A C 0.51970(12) 0.5232(2) 0.69432(11) 0.0220(5) Uani 1 1 d . . . . .
C20A C 0.56504(12) 0.6318(2) 0.67512(10) 0.0201(4) Uani 1 1 d . . . . .
C21A C 0.56995(12) 0.6709(2) 0.60618(10) 0.0220(5) Uani 1 1 d . . . . .
C22A C 0.57776(13) 0.8026(2) 0.58863(11) 0.0239(5) Uani 1 1 d . . . . .
H22A H 0.5771 0.8698 0.6209 0.029 Uiso 1 1 calc R U . . .
C23A C 0.58650(13) 0.8367(2) 0.52401(11) 0.0278(5) Uani 1 1 d . . . . .
H23A H 0.5917 0.9268 0.5124 0.033 Uiso 1 1 calc R U . . .
C24A C 0.58760(13) 0.7389(3) 0.47677(11) 0.0287(5) Uani 1 1 d . . . . .
H24A H 0.5944 0.7617 0.4329 0.034 Uiso 1 1 calc R U . . .
C25A C 0.57879(13) 0.6075(2) 0.49361(11) 0.0279(5) Uani 1 1 d . . . . .
H25A H 0.5790 0.5407 0.4611 0.034 Uiso 1 1 calc R U . . .
C26A C 0.56972(13) 0.5738(2) 0.55779(11) 0.0254(5) Uani 1 1 d . . . . .
H26A H 0.5633 0.4838 0.5689 0.030 Uiso 1 1 calc R U . . .
B1B B 0.83998(15) 0.1608(3) 0.50944(14) 0.0274(6) Uani 1 1 d . . . . .
N1B N 0.88671(11) 0.1489(2) 0.46039(10) 0.0305(5) Uani 1 1 d . . . . .
H1BN H 0.9150 0.2151 0.4547 0.037 Uiso 1 1 calc R U . . .
N2B N 0.79986(11) 0.0485(2) 0.52063(10) 0.0289(5) Uani 1 1 d . . . . .
H2BN H 0.7712 0.0526 0.5515 0.035 Uiso 1 1 calc R U . . .
O1B O 0.74643(11) 0.54382(18) 0.62462(9) 0.0401(5) Uani 1 1 d . . . . .
C1B C 0.89016(13) 0.0369(2) 0.42048(12) 0.0288(5) Uani 1 1 d . . . . .
C2B C 0.93242(15) 0.0318(3) 0.36992(13) 0.0350(6) Uani 1 1 d . . . . .
H2B H 0.9612 0.1048 0.3618 0.042 Uiso 1 1 calc R U . . .
C3B C 0.93274(15) -0.0822(3) 0.33036(14) 0.0379(6) Uani 1 1 d . . . . .
H3B H 0.9610 -0.0842 0.2949 0.046 Uiso 1 1 calc R U . . .
C4B C 0.89325(15) -0.1894(3) 0.34199(13) 0.0351(6) Uani 1 1 d . . . . .
H4B H 0.8945 -0.2651 0.3148 0.042 Uiso 1 1 calc R U . . .
C5B C 0.85029(14) -0.1888(3) 0.39448(12) 0.0305(5) Uani 1 1 d . . . . .
C6B C 0.80889(14) -0.2989(3) 0.40892(13) 0.0320(6) Uani 1 1 d . . . . .
H6B H 0.8104 -0.3773 0.3836 0.038 Uiso 1 1 calc R U . . .
C7B C 0.76692(14) -0.2932(3) 0.45886(13) 0.0334(6) Uani 1 1 d . . . . .
H7B H 0.7395 -0.3676 0.4677 0.040 Uiso 1 1 calc R U . . .
C8B C 0.76364(14) -0.1777(3) 0.49768(13) 0.0311(5) Uani 1 1 d . . . . .
H8B H 0.7342 -0.1753 0.5323 0.037 Uiso 1 1 calc R U . . .
C9B C 0.80306(13) -0.0694(2) 0.48526(12) 0.0259(5) Uani 1 1 d . . . . .
C10B C 0.84799(13) -0.0732(2) 0.43385(11) 0.0265(5) Uani 1 1 d . . . . .
C11B C 0.83284(13) 0.2962(2) 0.54609(12) 0.0279(5) Uani 1 1 d . . . . .
C12B C 0.89127(14) 0.3963(2) 0.55249(14) 0.0333(6) Uani 1 1 d . . . . .
H12B H 0.9068 0.4200 0.5088 0.040 Uiso 1 1 calc R U . . .
C13B C 0.95350(15) 0.3546(3) 0.60165(15) 0.0418(7) Uani 1 1 d . . . . .
H13B H 0.9715 0.2630 0.5965 0.050 Uiso 1 1 calc R U . . .
C14B C 1.00649(17) 0.4654(3) 0.60044(17) 0.0505(8) Uani 1 1 d . . . . .
H14B H 1.0500 0.4607 0.5826 0.061 Uiso 1 1 calc R U . . .
C15B C 0.98092(18) 0.5687(3) 0.62858(17) 0.0535(9) Uani 1 1 d . . . . .
H15B H 1.0027 0.6525 0.6342 0.064 Uiso 1 1 calc R U . . .
C16B C 0.91057(18) 0.5320(3) 0.65071(15) 0.0446(7) Uani 1 1 d . . . . .
H16B H 0.8934 0.5878 0.6861 0.054 Uiso 1 1 calc R U . . .
C17B C 0.86127(15) 0.5177(2) 0.58633(13) 0.0348(6) Uani 1 1 d . . . . .
H17B H 0.8616 0.5987 0.5584 0.042 Uiso 1 1 calc R U . . .
C18B C 0.92408(17) 0.3852(3) 0.66743(15) 0.0440(7) Uani 1 1 d . . . . .
H18C H 0.8811 0.3355 0.6735 0.053 Uiso 1 1 calc R U . . .
H18D H 0.9585 0.3725 0.7057 0.053 Uiso 1 1 calc R U . . .
C19B C 0.78820(15) 0.4771(2) 0.59872(12) 0.0312(6) Uani 1 1 d . . . . .
C20B C 0.77622(13) 0.3412(2) 0.57278(11) 0.0266(5) Uani 1 1 d . . . . .
C21B C 0.70925(13) 0.2740(2) 0.57853(11) 0.0259(5) Uani 1 1 d . . . . .
C22B C 0.69625(14) 0.2126(2) 0.63740(12) 0.0309(6) Uani 1 1 d . . . . .
H22B H 0.7313 0.2111 0.6729 0.037 Uiso 1 1 calc R U . . .
C23B C 0.63248(15) 0.1539(2) 0.64430(12) 0.0316(6) Uani 1 1 d . . . . .
H23B H 0.6244 0.1113 0.6842 0.038 Uiso 1 1 calc R U . . .
C24B C 0.58055(14) 0.1576(2) 0.59290(12) 0.0286(5) Uani 1 1 d . . . . .
H24B H 0.5366 0.1195 0.5979 0.034 Uiso 1 1 calc R U . . .
C25B C 0.59340(14) 0.2174(3) 0.53411(12) 0.0303(5) Uani 1 1 d . . . . .
H25B H 0.5582 0.2191 0.4987 0.036 Uiso 1 1 calc R U . . .
C26B C 0.65692(14) 0.2743(2) 0.52684(12) 0.0298(5) Uani 1 1 d . . . . .
H26B H 0.6652 0.3140 0.4863 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1A N1A 1.411(3) . ?
B1A N2A 1.426(3) . ?
B1A C11A 1.566(3) . ?
N1A C1A 1.394(3) . ?
N2A C9A 1.391(3) . ?
O1A C19A 1.221(3) . ?
C1A C2A 1.379(3) . ?
C1A C10A 1.435(3) . ?
C2A C3A 1.394(4) . ?
C3A C4A 1.374(4) . ?
C4A C5A 1.414(4) . ?
C5A C10A 1.423(3) . ?
C5A C6A 1.426(3) . ?
C6A C7A 1.364(4) . ?
C7A C8A 1.404(4) . ?
C8A C9A 1.387(3) . ?
C9A C10A 1.425(3) . ?
C11A C20A 1.355(3) . ?
C11A C12A 1.510(3) . ?
C12A C17A 1.549(3) . ?
C12A C13A 1.575(3) . ?
C13A C14A 1.521(3) . ?
C13A C18A 1.543(3) . ?
C14A C15A 1.329(4) . ?
C15A C16A 1.522(3) . ?
C16A C18A 1.537(4) . ?
C16A C17A 1.567(3) . ?
C17A C19A 1.517(3) . ?
C19A C20A 1.483(3) . ?
C20A C21A 1.479(3) . ?
C21A C22A 1.394(3) . ?
C21A C26A 1.396(3) . ?
C22A C23A 1.394(3) . ?
C23A C24A 1.387(3) . ?
C24A C25A 1.388(4) . ?
C25A C26A 1.386(3) . ?
B1B N2B 1.408(3) . ?
B1B N1B 1.419(4) . ?
B1B C11B 1.575(4) . ?
N1B C1B 1.403(3) . ?
N2B C9B 1.401(3) . ?
O1B C19B 1.213(3) . ?
C1B C2B 1.380(4) . ?
C1B C10B 1.424(3) . ?
C2B C3B 1.411(4) . ?
C3B C4B 1.362(4) . ?
C4B C5B 1.420(4) . ?
C5B C6B 1.421(4) . ?
C5B C10B 1.425(3) . ?
C6B C7B 1.366(4) . ?
C7B C8B 1.418(3) . ?
C8B C9B 1.374(3) . ?
C9B C10B 1.428(3) . ?
C11B C20B 1.350(4) . ?
C11B C12B 1.517(4) . ?
C12B C17B 1.551(4) . ?
C12B C13B 1.558(4) . ?
C13B C14B 1.523(4) . ?
C13B C18B 1.543(4) . ?
C14B C15B 1.313(5) . ?
C15B C16B 1.522(5) . ?
C16B C18B 1.542(4) . ?
C16B C17B 1.564(4) . ?
C17B C19B 1.519(4) . ?
C19B C20B 1.485(3) . ?
C20B C21B 1.480(4) . ?
C21B C26B 1.399(4) . ?
C21B C22B 1.400(3) . ?
C22B C23B 1.390(4) . ?
C23B C24B 1.390(4) . ?
C24B C25B 1.392(3) . ?
C25B C26B 1.380(4) . ?

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
N1A B1A N2A 117.4(2) . . ?
N1A B1A C11A 122.7(2) . . ?
N2A B1A C11A 119.7(2) . . ?
C1A N1A B1A 122.84(19) . . ?
C9A N2A B1A 122.3(2) . . ?
C2A C1A N1A 122.4(2) . . ?
C2A C1A C10A 119.7(2) . . ?
N1A C1A C10A 117.8(2) . . ?
C1A C2A C3A 120.5(2) . . ?
C4A C3A C2A 121.3(2) . . ?
C3A C4A C5A 120.2(2) . . ?
C4A C5A C10A 119.1(2) . . ?
C4A C5A C6A 122.6(2) . . ?
C10A C5A C6A 118.3(2) . . ?
C7A C6A C5A 120.3(2) . . ?
C6A C7A C8A 122.0(2) . . ?
C9A C8A C7A 119.4(2) . . ?
C8A C9A N2A 121.5(2) . . ?
C8A C9A C10A 120.1(2) . . ?
N2A C9A C10A 118.38(19) . . ?
C5A C10A C9A 119.8(2) . . ?
C5A C10A C1A 119.1(2) . . ?
C9A C10A C1A 121.1(2) . . ?
C20A C11A C12A 111.96(19) . . ?
C20A C11A B1A 129.5(2) . . ?
C12A C11A B1A 118.18(19) . . ?
C11A C12A C17A 105.23(17) . . ?
C11A C12A C13A 110.88(19) . . ?
C17A C12A C13A 103.10(18) . . ?
C14A C13A C18A 99.86(19) . . ?
C14A C13A C12A 106.15(19) . . ?
C18A C13A C12A 99.82(18) . . ?
C15A C14A C13A 107.7(2) . . ?
C14A C15A C16A 107.6(2) . . ?
C15A C16A C18A 99.8(2) . . ?
C15A C16A C17A 104.80(18) . . ?
C18A C16A C17A 101.57(18) . . ?
C19A C17A C12A 104.20(17) . . ?
C19A C17A C16A 113.02(18) . . ?
C12A C17A C16A 102.71(19) . . ?
C16A C18A C13A 93.95(18) . . ?
O1A C19A C20A 126.7(2) . . ?
O1A C19A C17A 124.7(2) . . ?
C20A C19A C17A 108.50(19) . . ?
C11A C20A C21A 127.4(2) . . ?
C11A C20A C19A 109.63(19) . . ?
C21A C20A C19A 122.90(19) . . ?
C22A C21A C26A 118.9(2) . . ?
C22A C21A C20A 121.4(2) . . ?
C26A C21A C20A 119.6(2) . . ?
C21A C22A C23A 120.5(2) . . ?
C24A C23A C22A 119.8(2) . . ?
C23A C24A C25A 120.0(2) . . ?
C26A C25A C24A 120.1(2) . . ?
C25A C26A C21A 120.6(2) . . ?
N2B B1B N1B 116.4(2) . . ?
N2B B1B C11B 123.4(2) . . ?
N1B B1B C11B 120.1(2) . . ?
C1B N1B B1B 123.3(2) . . ?
C9B N2B B1B 123.5(2) . . ?
C2B C1B N1B 122.1(2) . . ?
C2B C1B C10B 120.4(2) . . ?
N1B C1B C10B 117.5(2) . . ?
C1B C2B C3B 119.8(3) . . ?
C4B C3B C2B 121.3(2) . . ?
C3B C4B C5B 120.5(2) . . ?
C4B C5B C6B 122.5(2) . . ?
C4B C5B C10B 118.9(2) . . ?
C6B C5B C10B 118.6(2) . . ?
C7B C6B C5B 120.6(2) . . ?
C6B C7B C8B 121.1(2) . . ?
C9B C8B C7B 120.0(2) . . ?
C8B C9B N2B 122.2(2) . . ?
C8B C9B C10B 120.2(2) . . ?
N2B C9B C10B 117.6(2) . . ?
C1B C10B C5B 119.1(2) . . ?
C1B C10B C9B 121.4(2) . . ?
C5B C10B C9B 119.5(2) . . ?
C20B C11B C12B 111.6(2) . . ?
C20B C11B B1B 126.7(2) . . ?
C12B C11B B1B 121.7(2) . . ?
C11B C12B C17B 105.1(2) . . ?
C11B C12B C13B 113.8(2) . . ?
C17B C12B C13B 103.0(2) . . ?
C14B C13B C18B 99.8(3) . . ?
C14B C13B C12B 105.9(2) . . ?
C18B C13B C12B 100.6(2) . . ?
C15B C14B C13B 107.3(3) . . ?
C14B C15B C16B 108.7(3) . . ?
C15B C16B C18B 99.4(3) . . ?
C15B C16B C17B 105.5(3) . . ?
C18B C16B C17B 100.2(2) . . ?
C19B C17B C12B 104.7(2) . . ?
C19B C17B C16B 113.1(2) . . ?
C12B C17B C16B 103.0(2) . . ?
C16B C18B C13B 93.9(2) . . ?
O1B C19B C20B 125.7(3) . . ?
O1B C19B C17B 126.3(2) . . ?
C20B C19B C17B 108.0(2) . . ?
C11B C20B C21B 128.9(2) . . ?
C11B C20B C19B 110.6(2) . . ?
C21B C20B C19B 120.5(2) . . ?
C26B C21B C22B 118.6(2) . . ?
C26B C21B C20B 121.3(2) . . ?
C22B C21B C20B 120.1(2) . . ?
C23B C22B C21B 120.6(2) . . ?
C24B C23B C22B 120.1(2) . . ?
C23B C24B C25B 119.6(2) . . ?
C26B C25B C24B 120.5(2) . . ?
C25B C26B C21B 120.7(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
N2A B1A N1A C1A 0.2(3) . . . . ?
C11A B1A N1A C1A -174.4(2) . . . . ?
N1A B1A N2A C9A -3.2(3) . . . . ?
C11A B1A N2A C9A 171.6(2) . . . . ?
B1A N1A C1A C2A -177.4(2) . . . . ?
B1A N1A C1A C10A 2.5(3) . . . . ?
N1A C1A C2A C3A -178.5(2) . . . . ?
C10A C1A C2A C3A 1.6(4) . . . . ?
C1A C2A C3A C4A 0.7(4) . . . . ?
C2A C3A C4A C5A -1.4(4) . . . . ?
C3A C4A C5A C10A -0.2(4) . . . . ?
C3A C4A C5A C6A -179.1(2) . . . . ?
C4A C5A C6A C7A 178.3(2) . . . . ?
C10A C5A C6A C7A -0.5(4) . . . . ?
C5A C6A C7A C8A -0.2(4) . . . . ?
C6A C7A C8A C9A 0.6(4) . . . . ?
C7A C8A C9A N2A 179.0(2) . . . . ?
C7A C8A C9A C10A -0.2(3) . . . . ?
B1A N2A C9A C8A -176.1(2) . . . . ?
B1A N2A C9A C10A 3.2(3) . . . . ?
C4A C5A C10A C9A -178.1(2) . . . . ?
C6A C5A C10A C9A 0.8(3) . . . . ?
C4A C5A C10A C1A 2.4(3) . . . . ?
C6A C5A C10A C1A -178.7(2) . . . . ?
C8A C9A C10A C5A -0.5(3) . . . . ?
N2A C9A C10A C5A -179.7(2) . . . . ?
C8A C9A C10A C1A 179.0(2) . . . . ?
N2A C9A C10A C1A -0.2(3) . . . . ?
C2A C1A C10A C5A -3.1(3) . . . . ?
N1A C1A C10A C5A 176.9(2) . . . . ?
C2A C1A C10A C9A 177.4(2) . . . . ?
N1A C1A C10A C9A -2.5(3) . . . . ?
N1A B1A C11A C20A -52.7(4) . . . . ?
N2A B1A C11A C20A 132.8(2) . . . . ?
N1A B1A C11A C12A 119.8(2) . . . . ?
N2A B1A C11A C12A -54.7(3) . . . . ?
C20A C11A C12A C17A 0.9(3) . . . . ?
B1A C11A C12A C17A -172.84(19) . . . . ?
C20A C11A C12A C13A 111.7(2) . . . . ?
B1A C11A C12A C13A -62.0(2) . . . . ?
C11A C12A C13A C14A -177.05(18) . . . . ?
C17A C12A C13A C14A -64.9(2) . . . . ?
C11A C12A C13A C18A -73.7(2) . . . . ?
C17A C12A C13A C18A 38.5(2) . . . . ?
C18A C13A C14A C15A -33.1(3) . . . . ?
C12A C13A C14A C15A 70.2(2) . . . . ?
C13A C14A C15A C16A -0.4(3) . . . . ?
C14A C15A C16A C18A 33.9(2) . . . . ?
C14A C15A C16A C17A -71.0(3) . . . . ?
C11A C12A C17A C19A -4.7(2) . . . . ?
C13A C12A C17A C19A -120.96(18) . . . . ?
C11A C12A C17A C16A 113.38(19) . . . . ?
C13A C12A C17A C16A -2.9(2) . . . . ?
C15A C16A C17A C19A -178.7(2) . . . . ?
C18A C16A C17A C19A 77.7(2) . . . . ?
C15A C16A C17A C12A 69.6(2) . . . . ?
C18A C16A C17A C12A -33.9(2) . . . . ?
C15A C16A C18A C13A -50.50(19) . . . . ?
C17A C16A C18A C13A 56.97(19) . . . . ?
C14A C13A C18A C16A 50.3(2) . . . . ?
C12A C13A C18A C16A -58.15(19) . . . . ?
C12A C17A C19A O1A -171.6(2) . . . . ?
C16A C17A C19A O1A 77.7(3) . . . . ?
C12A C17A C19A C20A 6.8(2) . . . . ?
C16A C17A C19A C20A -103.9(2) . . . . ?
C12A C11A C20A C21A -173.9(2) . . . . ?
B1A C11A C20A C21A -1.1(4) . . . . ?
C12A C11A C20A C19A 3.5(3) . . . . ?
B1A C11A C20A C19A 176.3(2) . . . . ?
O1A C19A C20A C11A 171.7(2) . . . . ?
C17A C19A C20A C11A -6.6(3) . . . . ?
O1A C19A C20A C21A -10.7(4) . . . . ?
C17A C19A C20A C21A 171.0(2) . . . . ?
C11A C20A C21A C22A -39.4(4) . . . . ?
C19A C20A C21A C22A 143.5(2) . . . . ?
C11A C20A C21A C26A 137.9(3) . . . . ?
C19A C20A C21A C26A -39.2(3) . . . . ?
C26A C21A C22A C23A -1.2(4) . . . . ?
C20A C21A C22A C23A 176.1(2) . . . . ?
C21A C22A C23A C24A -0.1(4) . . . . ?
C22A C23A C24A C25A 1.1(4) . . . . ?
C23A C24A C25A C26A -0.8(4) . . . . ?
C24A C25A C26A C21A -0.6(4) . . . . ?
C22A C21A C26A C25A 1.5(4) . . . . ?
C20A C21A C26A C25A -175.8(2) . . . . ?
N2B B1B N1B C1B 5.2(4) . . . . ?
C11B B1B N1B C1B -172.4(2) . . . . ?
N1B B1B N2B C9B -1.5(4) . . . . ?
C11B B1B N2B C9B 175.9(2) . . . . ?
B1B N1B C1B C2B 175.1(2) . . . . ?
B1B N1B C1B C10B -4.9(4) . . . . ?
N1B C1B C2B C3B -178.6(2) . . . . ?
C10B C1B C2B C3B 1.4(4) . . . . ?
C1B C2B C3B C4B -1.6(4) . . . . ?
C2B C3B C4B C5B 0.2(4) . . . . ?
C3B C4B C5B C6B -179.2(3) . . . . ?
C3B C4B C5B C10B 1.4(4) . . . . ?
C4B C5B C6B C7B -178.3(3) . . . . ?
C10B C5B C6B C7B 1.1(4) . . . . ?
C5B C6B C7B C8B -0.2(4) . . . . ?
C6B C7B C8B C9B 0.0(4) . . . . ?
C7B C8B C9B N2B 177.7(2) . . . . ?
C7B C8B C9B C10B -0.8(4) . . . . ?
B1B N2B C9B C8B 179.5(3) . . . . ?
B1B N2B C9B C10B -2.1(4) . . . . ?
C2B C1B C10B C5B 0.3(4) . . . . ?
N1B C1B C10B C5B -179.8(2) . . . . ?
C2B C1B C10B C9B -179.0(2) . . . . ?
N1B C1B C10B C9B 0.9(4) . . . . ?
C4B C5B C10B C1B -1.6(4) . . . . ?
C6B C5B C10B C1B 179.0(2) . . . . ?
C4B C5B C10B C9B 177.7(2) . . . . ?
C6B C5B C10B C9B -1.7(4) . . . . ?
C8B C9B C10B C1B -179.1(2) . . . . ?
N2B C9B C10B C1B 2.4(4) . . . . ?
C8B C9B C10B C5B 1.6(4) . . . . ?
N2B C9B C10B C5B -176.9(2) . . . . ?
N2B B1B C11B C20B -25.5(4) . . . . ?
N1B B1B C11B C20B 151.9(3) . . . . ?
N2B B1B C11B C12B 157.4(2) . . . . ?
N1B B1B C11B C12B -25.3(4) . . . . ?
C20B C11B C12B C17B -1.9(3) . . . . ?
B1B C11B C12B C17B 175.6(2) . . . . ?
C20B C11B C12B C13B 110.1(3) . . . . ?
B1B C11B C12B C13B -72.4(3) . . . . ?
C11B C12B C13B C14B 179.2(2) . . . . ?
C17B C12B C13B C14B -67.6(3) . . . . ?
C11B C12B C13B C18B -77.3(3) . . . . ?
C17B C12B C13B C18B 35.9(3) . . . . ?
C18B C13B C14B C15B -34.1(3) . . . . ?
C12B C13B C14B C15B 70.0(3) . . . . ?
C13B C14B C15B C16B 0.8(4) . . . . ?
C14B C15B C16B C18B 32.8(3) . . . . ?
C14B C15B C16B C17B -70.6(3) . . . . ?
C11B C12B C17B C19B 1.5(3) . . . . ?
C13B C12B C17B C19B -117.9(2) . . . . ?
C11B C12B C17B C16B 120.0(2) . . . . ?
C13B C12B C17B C16B 0.6(3) . . . . ?
C15B C16B C17B C19B 178.4(2) . . . . ?
C18B C16B C17B C19B 75.6(3) . . . . ?
C15B C16B C17B C12B 66.0(3) . . . . ?
C18B C16B C17B C12B -36.8(3) . . . . ?
C15B C16B C18B C13B -49.8(3) . . . . ?
C17B C16B C18B C13B 57.9(3) . . . . ?
C14B C13B C18B C16B 50.6(3) . . . . ?
C12B C13B C18B C16B -57.8(2) . . . . ?
C12B C17B C19B O1B 179.9(3) . . . . ?
C16B C17B C19B O1B 68.5(3) . . . . ?
C12B C17B C19B C20B -0.8(3) . . . . ?
C16B C17B C19B C20B -112.2(2) . . . . ?
C12B C11B C20B C21B -178.2(2) . . . . ?
B1B C11B C20B C21B 4.4(4) . . . . ?
C12B C11B C20B C19B 1.5(3) . . . . ?
B1B C11B C20B C19B -175.9(2) . . . . ?
O1B C19B C20B C11B 178.9(3) . . . . ?
C17B C19B C20B C11B -0.4(3) . . . . ?
O1B C19B C20B C21B -1.4(4) . . . . ?
C17B C19B C20B C21B 179.3(2) . . . . ?
C11B C20B C21B C26B -83.8(3) . . . . ?
C19B C20B C21B C26B 96.6(3) . . . . ?
C11B C20B C21B C22B 98.7(3) . . . . ?
C19B C20B C21B C22B -81.0(3) . . . . ?
C26B C21B C22B C23B -0.3(4) . . . . ?
C20B C21B C22B C23B 177.3(2) . . . . ?
C21B C22B C23B C24B -1.0(4) . . . . ?
C22B C23B C24B C25B 1.6(4) . . . . ?
C23B C24B C25B C26B -0.8(4) . . . . ?
C24B C25B C26B C21B -0.6(4) . . . . ?
C22B C21B C26B C25B 1.2(4) . . . . ?
C20B C21B C26B C25B -176.4(2) . . . . ?

_refine_diff_density_max         0.358
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.064
_shelxl_version_number           2014-3
