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

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

data_I534
_audit_block_doi                 10.5072/ccdc.csd.cc20plbn
_database_code_depnum_ccdc_archive 'CCDC 1867791'
_audit_update_record             
;
2018-09-14 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H21 Cl N2 O'
_chemical_formula_weight         256.77

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.7652(11)
_cell_length_b                   14.8258(18)
_cell_length_c                   10.1665(12)
_cell_angle_alpha                90
_cell_angle_beta                 108.135(4)
_cell_angle_gamma                90
_cell_volume                     1398.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5507
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      29.15

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.182
_exptl_absorpt_coefficient_mu    0.261
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13329
_diffrn_reflns_av_unetI/netI     0.0980
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.516
_diffrn_reflns_theta_max         29.651
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3929
_reflns_number_gt                2468
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2016.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_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)+(0.0375P)²+1.0184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3929
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
Cl1 Cl 0.92510(6) 0.78248(4) 0.30208(6) 0.02316(15) Uani 1 1 d . . . . .
N1 N 0.63110(17) 0.57820(11) 0.31698(17) 0.0131(4) Uani 1 1 d . . . . .
N2 N 0.58163(17) 0.68451(11) 0.44484(17) 0.0131(4) Uani 1 1 d . . . . .
C1 C 0.6767(2) 0.65470(13) 0.3846(2) 0.0147(4) Uani 1 1 d . . . . .
H1 H 0.764537 0.684097 0.389421 0.018 Uiso 1 1 calc R U . . .
C2 C 0.4977(2) 0.55690(13) 0.3317(2) 0.0135(4) Uani 1 1 d . . . . .
C3 C 0.4049(2) 0.48421(14) 0.2836(2) 0.0165(4) Uani 1 1 d . . . . .
H3 H 0.427243 0.436862 0.230694 0.020 Uiso 1 1 calc R U . . .
C4 C 0.2783(2) 0.48530(15) 0.3177(2) 0.0192(5) Uani 1 1 d . . . . .
H4 H 0.210932 0.437746 0.285605 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2459(2) 0.55429(15) 0.3980(2) 0.0198(5) Uani 1 1 d . . . . .
H5 H 0.157351 0.552252 0.418316 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3397(2) 0.62494(14) 0.4482(2) 0.0170(4) Uani 1 1 d . . . . .
H6 H 0.319001 0.671262 0.503755 0.020 Uiso 1 1 calc R U . . .
C7 C 0.4659(2) 0.62438(13) 0.4127(2) 0.0134(4) Uani 1 1 d . . . . .
C8 C 0.7025(2) 0.52859(14) 0.2291(2) 0.0185(5) Uani 1 1 d . . . . .
H8 H 0.669318 0.464448 0.221359 0.022 Uiso 1 1 calc R U . . .
C9 C 0.6576(3) 0.5694(2) 0.0857(2) 0.0356(6) Uani 1 1 d . . . . .
H9A H 0.690535 0.530713 0.023402 0.053 Uiso 1 1 calc R U . . .
H9B H 0.700788 0.629423 0.089475 0.053 Uiso 1 1 calc R U . . .
H9C H 0.552385 0.574605 0.051229 0.053 Uiso 1 1 calc R U . . .
C10 C 0.8644(2) 0.52986(16) 0.2939(2) 0.0234(5) Uani 1 1 d . . . . .
H10A H 0.908946 0.492952 0.238374 0.035 Uiso 1 1 calc R U . . .
H10B H 0.889732 0.505416 0.388002 0.035 Uiso 1 1 calc R U . . .
H10C H 0.899418 0.592033 0.297380 0.035 Uiso 1 1 calc R U . . .
C11 C 0.5904(2) 0.76817(14) 0.5279(2) 0.0177(4) Uani 1 1 d . . . . .
H11 H 0.560279 0.753485 0.610883 0.021 Uiso 1 1 calc R U . . .
C12 C 0.4865(2) 0.83791(15) 0.4414(3) 0.0257(5) Uani 1 1 d . . . . .
H12A H 0.491911 0.893176 0.495693 0.039 Uiso 1 1 calc R U . . .
H12B H 0.388101 0.814013 0.414932 0.039 Uiso 1 1 calc R U . . .
H12C H 0.512613 0.851464 0.357933 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7448(2) 0.80302(16) 0.5772(2) 0.0235(5) Uani 1 1 d . . . . .
H13A H 0.751301 0.854213 0.639797 0.035 Uiso 1 1 calc R U . . .
H13B H 0.773183 0.822453 0.497226 0.035 Uiso 1 1 calc R U . . .
H13C H 0.809298 0.754801 0.626171 0.035 Uiso 1 1 calc R U . . .
O1W O 1.0757(2) 0.69041(14) 0.6162(2) 0.0419(5) Uani 1 1 d . . . . .
H1W H 1.045(4) 0.723(2) 0.532(4) 0.079(12) Uiso 1 1 d . . . . .
H2W H 1.168(5) 0.703(3) 0.660(4) 0.088(14) 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
N1 C1 1.329(3) . ?
N1 C2 1.393(2) . ?
N1 C8 1.488(3) . ?
N2 C1 1.336(2) . ?
N2 C7 1.396(2) . ?
N2 C11 1.488(3) . ?
C1 H1 0.9500 . ?
C2 C7 1.391(3) . ?
C2 C3 1.395(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C8 C10 1.511(3) . ?
C8 C9 1.512(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.522(3) . ?
C11 C13 1.524(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O1W H1W 0.95(4) . ?
O1W H2W 0.89(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
C1 N1 C2 108.16(16) . . ?
C1 N1 C8 126.04(16) . . ?
C2 N1 C8 125.54(16) . . ?
C1 N2 C7 107.97(16) . . ?
C1 N2 C11 127.62(16) . . ?
C7 N2 C11 124.38(16) . . ?
N1 C1 N2 110.54(17) . . ?
N1 C1 H1 124.7 . . ?
N2 C1 H1 124.7 . . ?
C7 C2 N1 106.80(17) . . ?
C7 C2 C3 121.52(18) . . ?
N1 C2 C3 131.67(19) . . ?
C4 C3 C2 115.90(19) . . ?
C4 C3 H3 122.1 . . ?
C2 C3 H3 122.1 . . ?
C3 C4 C5 122.29(19) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 121.59(19) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 116.11(19) . . ?
C5 C6 H6 121.9 . . ?
C7 C6 H6 121.9 . . ?
C6 C7 C2 122.56(18) . . ?
C6 C7 N2 130.92(19) . . ?
C2 C7 N2 106.52(17) . . ?
N1 C8 C10 110.73(17) . . ?
N1 C8 C9 109.37(17) . . ?
C10 C8 C9 111.46(19) . . ?
N1 C8 H8 108.4 . . ?
C10 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 109.17(17) . . ?
N2 C11 C13 110.20(16) . . ?
C12 C11 C13 111.91(18) . . ?
N2 C11 H11 108.5 . . ?
C12 C11 H11 108.5 . . ?
C13 C11 H11 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H1W O1W H2W 109(3) . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.074



####################################################################### 
# 
# 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_F530
_database_code_depnum_ccdc_archive 'CCDC 1853201'
_audit_update_record             
;
2018-07-03 deposited with the CCDC.
2018-10-08 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            'C14 H19 N3 S'
_chemical_formula_weight         261.38

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.1115(3)
_cell_length_b                   12.4689(7)
_cell_length_c                   15.8457(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.346(2)
_cell_angle_gamma                90
_cell_volume                     1402.68(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3959
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.10

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.218
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6846
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Microfocusing Source'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13226
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.575
_diffrn_reflns_theta_max         28.265
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3484
_reflns_number_gt                2485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+1.0583P] 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         3484
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_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 0.78937(7) 0.88865(4) 0.33882(3) 0.02770(15) Uani 1 1 d . . . . .
N1 N 0.2275(2) 0.69983(12) 0.48105(9) 0.0166(3) Uani 1 1 d . . . . .
N2 N 0.1683(2) 0.59377(11) 0.37250(8) 0.0140(3) Uani 1 1 d . . . . .
N3 N 0.4684(3) 0.78022(15) 0.27316(13) 0.0370(5) Uani 1 1 d . . . . .
C1 C 0.1812(2) 0.69520(14) 0.39827(10) 0.0166(4) Uani 1 1 d . . . . .
H1 H 0.1604 0.7559 0.3627 0.020 Uiso 1 1 calc R U . . .
C2 C 0.2457(2) 0.59540(14) 0.51127(10) 0.0154(4) Uani 1 1 d . . . . .
C3 C 0.2900(2) 0.55470(16) 0.59208(11) 0.0199(4) Uani 1 1 d . . . . .
H3 H 0.3131 0.6004 0.6395 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2985(3) 0.44440(16) 0.59920(12) 0.0228(4) Uani 1 1 d . . . . .
H4 H 0.3296 0.4134 0.6530 0.027 Uiso 1 1 calc R U . . .
C5 C 0.2624(3) 0.37682(16) 0.52937(12) 0.0226(4) Uani 1 1 d . . . . .
H5 H 0.2697 0.3014 0.5373 0.027 Uiso 1 1 calc R U . . .
C6 C 0.2167(2) 0.41659(15) 0.44965(11) 0.0183(4) Uani 1 1 d . . . . .
H6 H 0.1914 0.3707 0.4025 0.022 Uiso 1 1 calc R U . . .
C7 C 0.2096(2) 0.52805(14) 0.44221(10) 0.0146(4) Uani 1 1 d . . . . .
C8 C 0.2531(3) 0.79844(15) 0.53302(11) 0.0217(4) Uani 1 1 d . . . . .
H8 H 0.3580 0.7849 0.5766 0.026 Uiso 1 1 calc R U . . .
C9 C 0.0790(4) 0.8228(2) 0.57857(15) 0.0430(6) Uani 1 1 d . . . . .
H9A H -0.0258 0.8375 0.5373 0.064 Uiso 1 1 calc R U . . .
H9B H 0.1014 0.8858 0.6148 0.064 Uiso 1 1 calc R U . . .
H9C H 0.0476 0.7611 0.6134 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3091(4) 0.89219(18) 0.47988(14) 0.0403(6) Uani 1 1 d . . . . .
H10A H 0.4202 0.8730 0.4493 0.060 Uiso 1 1 calc R U . . .
H10B H 0.3386 0.9540 0.5165 0.060 Uiso 1 1 calc R U . . .
H10C H 0.2048 0.9105 0.4393 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1223(3) 0.55436(14) 0.28531(10) 0.0168(4) Uani 1 1 d . . . . .
H11 H 0.0306 0.4939 0.2885 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2995(3) 0.51120(16) 0.24818(11) 0.0224(4) Uani 1 1 d . . . . .
H12A H 0.3910 0.5694 0.2439 0.034 Uiso 1 1 calc R U . . .
H12B H 0.2677 0.4817 0.1918 0.034 Uiso 1 1 calc R U . . .
H12C H 0.3540 0.4546 0.2849 0.034 Uiso 1 1 calc R U . . .
C13 C 0.0305(3) 0.64171(16) 0.23059(11) 0.0238(4) Uani 1 1 d . . . . .
H13A H -0.0756 0.6724 0.2592 0.036 Uiso 1 1 calc R U . . .
H13B H -0.0151 0.6112 0.1762 0.036 Uiso 1 1 calc R U . . .
H13C H 0.1230 0.6981 0.2210 0.036 Uiso 1 1 calc R U . . .
C14 C 0.6016(3) 0.82406(15) 0.30027(12) 0.0217(4) 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
S1 C14 1.646(2) . ?
N1 C1 1.335(2) . ?
N1 C2 1.391(2) . ?
N1 C8 1.485(2) . ?
N2 C1 1.331(2) . ?
N2 C7 1.393(2) . ?
N2 C11 1.485(2) . ?
N3 C14 1.154(3) . ?
C1 H1 0.9500 . ?
C2 C7 1.391(2) . ?
C2 C3 1.396(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.501(3) . ?
C8 C10 1.508(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.516(3) . ?
C11 C12 1.520(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 108.09(14) . . ?
C1 N1 C8 126.58(15) . . ?
C2 N1 C8 125.32(14) . . ?
C1 N2 C7 107.94(14) . . ?
C1 N2 C11 127.43(14) . . ?
C7 N2 C11 124.62(14) . . ?
N2 C1 N1 110.58(15) . . ?
N2 C1 H1 124.7 . . ?
N1 C1 H1 124.7 . . ?
N1 C2 C7 106.56(14) . . ?
N1 C2 C3 131.88(17) . . ?
C7 C2 C3 121.56(17) . . ?
C4 C3 C2 116.32(17) . . ?
C4 C3 H3 121.8 . . ?
C2 C3 H3 121.8 . . ?
C3 C4 C5 121.93(17) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 121.97(18) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 116.17(17) . . ?
C5 C6 H6 121.9 . . ?
C7 C6 H6 121.9 . . ?
C2 C7 N2 106.82(15) . . ?
C2 C7 C6 122.05(16) . . ?
N2 C7 C6 131.13(16) . . ?
N1 C8 C9 110.89(16) . . ?
N1 C8 C10 111.10(15) . . ?
C9 C8 C10 111.34(19) . . ?
N1 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C10 C8 H8 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C13 111.01(14) . . ?
N2 C11 C12 109.57(14) . . ?
C13 C11 C12 111.84(15) . . ?
N2 C11 H11 108.1 . . ?
C13 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 S1 178.96(19) . . ?

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
C7 N2 C1 N1 -0.4(2) . . . . ?
C11 N2 C1 N1 -179.21(15) . . . . ?
C2 N1 C1 N2 -0.1(2) . . . . ?
C8 N1 C1 N2 -179.30(16) . . . . ?
C1 N1 C2 C7 0.52(19) . . . . ?
C8 N1 C2 C7 179.75(16) . . . . ?
C1 N1 C2 C3 -179.44(18) . . . . ?
C8 N1 C2 C3 -0.2(3) . . . . ?
N1 C2 C3 C4 -179.17(18) . . . . ?
C7 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
N1 C2 C7 N2 -0.75(18) . . . . ?
C3 C2 C7 N2 179.21(15) . . . . ?
N1 C2 C7 C6 179.64(15) . . . . ?
C3 C2 C7 C6 -0.4(3) . . . . ?
C1 N2 C7 C2 0.72(19) . . . . ?
C11 N2 C7 C2 179.57(15) . . . . ?
C1 N2 C7 C6 -179.73(18) . . . . ?
C11 N2 C7 C6 -0.9(3) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C5 C6 C7 N2 -179.79(17) . . . . ?
C1 N1 C8 C9 98.1(2) . . . . ?
C2 N1 C8 C9 -81.0(2) . . . . ?
C1 N1 C8 C10 -26.3(3) . . . . ?
C2 N1 C8 C10 154.63(18) . . . . ?
C1 N2 C11 C13 -17.9(2) . . . . ?
C7 N2 C11 C13 163.47(16) . . . . ?
C1 N2 C11 C12 106.1(2) . . . . ?
C7 N2 C11 C12 -72.5(2) . . . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_f531
_database_code_depnum_ccdc_archive 'CCDC 1853200'
_audit_update_record             
;
2018-07-03 deposited with the CCDC.
2018-10-08 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            'C37 H39 B N2'
_chemical_formula_weight         522.51

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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                   9.8653(3)
_cell_length_b                   16.7612(5)
_cell_length_c                   18.1753(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3005.36(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      26.58

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.287
_exptl_crystal_size_min          0.206
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7005
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Microfocusing Source'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35919
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7458
_reflns_number_gt                6097
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0329P)²+0.5542P] 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_abs_structure_details 
; 
 Flack x determined using 2243 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -1.0(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7458
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N1 N 0.58759(17) 0.31757(10) 0.31470(8) 0.0189(4) Uani 1 1 d . . . . .
N2 N 0.76886(17) 0.27565(10) 0.25737(9) 0.0188(4) Uani 1 1 d . . . . .
C1 C 0.6937(2) 0.33870(13) 0.27418(10) 0.0191(4) Uani 1 1 d . . . . .
H1 H 0.7132 0.3918 0.2592 0.023 Uiso 1 1 calc R U . . .
C2 C 0.5945(2) 0.23524(12) 0.32667(10) 0.0189(4) Uani 1 1 d . . . . .
C3 C 0.5131(2) 0.18449(13) 0.36809(11) 0.0227(5) Uani 1 1 d . . . . .
H3 H 0.4340 0.2030 0.3926 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5535(2) 0.10612(13) 0.37157(12) 0.0254(5) Uani 1 1 d . . . . .
H4 H 0.5007 0.0692 0.3990 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6706(2) 0.07917(13) 0.33559(12) 0.0266(5) Uani 1 1 d . . . . .
H5 H 0.6950 0.0245 0.3396 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7514(2) 0.12932(13) 0.29461(11) 0.0239(5) Uani 1 1 d . . . . .
H6 H 0.8307 0.1107 0.2705 0.029 Uiso 1 1 calc R U . . .
C7 C 0.7108(2) 0.20870(12) 0.29042(10) 0.0198(4) Uani 1 1 d . . . . .
C8 C 0.4781(2) 0.37018(13) 0.34270(12) 0.0245(5) Uani 1 1 d . . . . .
H8 H 0.4633 0.3572 0.3958 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3476(2) 0.35191(16) 0.30165(16) 0.0397(6) Uani 1 1 d . . . . .
H9A H 0.3577 0.3671 0.2499 0.060 Uiso 1 1 calc R U . . .
H9B H 0.2728 0.3821 0.3236 0.060 Uiso 1 1 calc R U . . .
H9C H 0.3281 0.2947 0.3049 0.060 Uiso 1 1 calc R U . . .
C10 C 0.5183(3) 0.45723(13) 0.33748(13) 0.0308(5) Uani 1 1 d . . . . .
H10A H 0.6046 0.4654 0.3631 0.046 Uiso 1 1 calc R U . . .
H10B H 0.4481 0.4903 0.3603 0.046 Uiso 1 1 calc R U . . .
H10C H 0.5283 0.4722 0.2856 0.046 Uiso 1 1 calc R U . . .
C11 C 0.8895(2) 0.27895(13) 0.20818(11) 0.0229(5) Uani 1 1 d . . . . .
H11 H 0.8960 0.3346 0.1887 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8694(2) 0.22381(14) 0.14266(11) 0.0265(5) Uani 1 1 d . . . . .
H12A H 0.8624 0.1686 0.1599 0.040 Uiso 1 1 calc R U . . .
H12B H 0.9469 0.2287 0.1092 0.040 Uiso 1 1 calc R U . . .
H12C H 0.7861 0.2386 0.1167 0.040 Uiso 1 1 calc R U . . .
C13 C 1.0181(2) 0.26256(14) 0.25114(13) 0.0293(5) Uani 1 1 d . . . . .
H13A H 1.0238 0.2994 0.2929 0.044 Uiso 1 1 calc R U . . .
H13B H 1.0969 0.2702 0.2190 0.044 Uiso 1 1 calc R U . . .
H13C H 1.0168 0.2075 0.2693 0.044 Uiso 1 1 calc R U . . .
C14 C 0.4643(2) 0.51168(12) 0.54761(10) 0.0176(4) Uani 1 1 d . . . . .
C15 C 0.3828(2) 0.45333(12) 0.51482(11) 0.0206(4) Uani 1 1 d . . . . .
H15 H 0.4174 0.4006 0.5111 0.025 Uiso 1 1 calc R U . . .
C16 C 0.2540(2) 0.46849(13) 0.48750(11) 0.0242(5) Uani 1 1 d . . . . .
H16 H 0.2034 0.4266 0.4655 0.029 Uiso 1 1 calc R U . . .
C17 C 0.1989(2) 0.54397(13) 0.49209(11) 0.0250(5) Uani 1 1 d . . . . .
H17 H 0.1109 0.5547 0.4733 0.030 Uiso 1 1 calc R U . . .
C18 C 0.2752(2) 0.60377(13) 0.52476(12) 0.0276(5) Uani 1 1 d . . . . .
H18 H 0.2389 0.6561 0.5290 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4042(2) 0.58760(12) 0.55131(11) 0.0235(5) Uani 1 1 d . . . . .
H19 H 0.4543 0.6299 0.5730 0.028 Uiso 1 1 calc R U . . .
C20 C 0.6777(2) 0.41149(12) 0.54446(10) 0.0182(4) Uani 1 1 d . . . . .
C21 C 0.6295(2) 0.33543(12) 0.56453(11) 0.0213(4) Uani 1 1 d . . . . .
H21 H 0.5635 0.3317 0.6024 0.026 Uiso 1 1 calc R U . . .
C22 C 0.6742(2) 0.26573(13) 0.53142(11) 0.0251(5) Uani 1 1 d . . . . .
H22 H 0.6378 0.2158 0.5463 0.030 Uiso 1 1 calc R U . . .
C23 C 0.7722(2) 0.26861(13) 0.47653(11) 0.0255(5) Uani 1 1 d . . . . .
H23 H 0.8035 0.2210 0.4538 0.031 Uiso 1 1 calc R U . . .
C24 C 0.8234(2) 0.34211(13) 0.45564(11) 0.0245(5) Uani 1 1 d . . . . .
H24 H 0.8907 0.3452 0.4184 0.029 Uiso 1 1 calc R U . . .
C25 C 0.7764(2) 0.41146(12) 0.48921(10) 0.0206(4) Uani 1 1 d . . . . .
H25 H 0.8130 0.4611 0.4738 0.025 Uiso 1 1 calc R U . . .
C26 C 0.7213(2) 0.56723(11) 0.56291(10) 0.0177(4) Uani 1 1 d . . . . .
C27 C 0.7093(2) 0.61498(12) 0.49951(11) 0.0213(4) Uani 1 1 d . . . . .
H27 H 0.6344 0.6066 0.4676 0.026 Uiso 1 1 calc R U . . .
C28 C 0.8027(2) 0.67372(12) 0.48186(11) 0.0244(5) Uani 1 1 d . . . . .
H28 H 0.7911 0.7040 0.4381 0.029 Uiso 1 1 calc R U . . .
C29 C 0.9125(2) 0.68878(13) 0.52709(11) 0.0254(5) Uani 1 1 d . . . . .
H29 H 0.9749 0.7301 0.5156 0.031 Uiso 1 1 calc R U . . .
C30 C 0.9295(2) 0.64239(13) 0.58956(12) 0.0244(5) Uani 1 1 d . . . . .
H30 H 1.0047 0.6513 0.6211 0.029 Uiso 1 1 calc R U . . .
C31 C 0.8360(2) 0.58271(12) 0.60599(11) 0.0207(4) Uani 1 1 d . . . . .
H31 H 0.8509 0.5509 0.6485 0.025 Uiso 1 1 calc R U . . .
C32 C 0.6057(2) 0.48189(11) 0.67167(10) 0.0171(4) Uani 1 1 d . . . . .
C33 C 0.5054(2) 0.51763(12) 0.71552(11) 0.0202(4) Uani 1 1 d . . . . .
H33 H 0.4382 0.5495 0.6923 0.024 Uiso 1 1 calc R U . . .
C34 C 0.5005(2) 0.50825(13) 0.79178(11) 0.0243(5) Uani 1 1 d . . . . .
H34 H 0.4308 0.5336 0.8192 0.029 Uiso 1 1 calc R U . . .
C35 C 0.5961(2) 0.46242(12) 0.82760(11) 0.0251(5) Uani 1 1 d . . . . .
H35 H 0.5923 0.4556 0.8794 0.030 Uiso 1 1 calc R U . . .
C36 C 0.6974(2) 0.42664(12) 0.78684(11) 0.0230(5) Uani 1 1 d . . . . .
H36 H 0.7646 0.3953 0.8107 0.028 Uiso 1 1 calc R U . . .
C37 C 0.7013(2) 0.43647(12) 0.71067(11) 0.0207(4) Uani 1 1 d . . . . .
H37 H 0.7720 0.4112 0.6839 0.025 Uiso 1 1 calc R U . . .
B1 B 0.6159(2) 0.49350(13) 0.58131(12) 0.0163(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.328(3) . ?
N1 C2 1.399(3) . ?
N1 C8 1.485(3) . ?
N2 C1 1.326(3) . ?
N2 C7 1.396(3) . ?
N2 C11 1.490(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(3) . ?
C2 C7 1.395(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(3) . ?
C6 H6 0.9500 . ?
C8 C10 1.515(3) . ?
C8 C9 1.519(3) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.515(3) . ?
C11 C12 1.520(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.399(3) . ?
C14 C19 1.405(3) . ?
C14 B1 1.645(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.398(3) . ?
C20 C21 1.409(3) . ?
C20 B1 1.646(3) . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C31 1.401(3) . ?
C26 C27 1.408(3) . ?
C26 B1 1.649(3) . ?
C27 C28 1.386(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.392(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C37 1.404(3) . ?
C32 C33 1.404(3) . ?
C32 B1 1.657(3) . ?
C33 C34 1.396(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.382(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.395(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 108.10(17) . . ?
C1 N1 C8 127.26(17) . . ?
C2 N1 C8 124.64(17) . . ?
C1 N2 C7 108.18(16) . . ?
C1 N2 C11 123.72(17) . . ?
C7 N2 C11 128.02(17) . . ?
N2 C1 N1 110.84(18) . . ?
N2 C1 H1 124.6 . . ?
N1 C1 H1 124.6 . . ?
C3 C2 C7 122.35(19) . . ?
C3 C2 N1 131.22(19) . . ?
C7 C2 N1 106.35(17) . . ?
C4 C3 C2 116.2(2) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 121.9 . . ?
C3 C4 C5 121.7(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 116.5(2) . . ?
C5 C6 H6 121.7 . . ?
C7 C6 H6 121.7 . . ?
C6 C7 C2 121.04(19) . . ?
C6 C7 N2 132.39(19) . . ?
C2 C7 N2 106.50(17) . . ?
N1 C8 C10 111.07(18) . . ?
N1 C8 C9 109.18(17) . . ?
C10 C8 C9 112.7(2) . . ?
N1 C8 H8 107.9 . . ?
C10 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C13 110.68(16) . . ?
N2 C11 C12 110.09(17) . . ?
C13 C11 C12 113.74(18) . . ?
N2 C11 H11 107.3 . . ?
C13 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 114.3(2) . . ?
C15 C14 B1 123.48(18) . . ?
C19 C14 B1 122.24(18) . . ?
C16 C15 C14 123.4(2) . . ?
C16 C15 H15 118.3 . . ?
C14 C15 H15 118.3 . . ?
C17 C16 C15 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 118.3(2) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 123.2(2) . . ?
C18 C19 H19 118.4 . . ?
C14 C19 H19 118.4 . . ?
C25 C20 C21 114.87(19) . . ?
C25 C20 B1 123.38(18) . . ?
C21 C20 B1 121.69(18) . . ?
C22 C21 C20 122.9(2) . . ?
C22 C21 H21 118.6 . . ?
C20 C21 H21 118.6 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 118.78(19) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 120.1(2) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 123.2(2) . . ?
C24 C25 H25 118.4 . . ?
C20 C25 H25 118.4 . . ?
C31 C26 C27 114.82(19) . . ?
C31 C26 B1 122.35(17) . . ?
C27 C26 B1 122.63(18) . . ?
C28 C27 C26 122.5(2) . . ?
C28 C27 H27 118.7 . . ?
C26 C27 H27 118.7 . . ?
C29 C28 C27 120.82(19) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 118.6(2) . . ?
C28 C29 H29 120.7 . . ?
C30 C29 H29 120.7 . . ?
C29 C30 C31 119.9(2) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C26 123.25(19) . . ?
C30 C31 H31 118.4 . . ?
C26 C31 H31 118.4 . . ?
C37 C32 C33 114.71(17) . . ?
C37 C32 B1 121.54(18) . . ?
C33 C32 B1 123.73(18) . . ?
C34 C33 C32 122.7(2) . . ?
C34 C33 H33 118.7 . . ?
C32 C33 H33 118.7 . . ?
C35 C34 C33 120.5(2) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 118.90(19) . . ?
C34 C35 H35 120.6 . . ?
C36 C35 H35 120.6 . . ?
C35 C36 C37 120.0(2) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C32 123.2(2) . . ?
C36 C37 H37 118.4 . . ?
C32 C37 H37 118.4 . . ?
C14 B1 C20 109.88(16) . . ?
C14 B1 C26 111.04(16) . . ?
C20 B1 C26 108.04(16) . . ?
C14 B1 C32 109.61(17) . . ?
C20 B1 C32 109.13(16) . . ?
C26 B1 C32 109.11(16) . . ?

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
C7 N2 C1 N1 -1.6(2) . . . . ?
C11 N2 C1 N1 175.61(16) . . . . ?
C2 N1 C1 N2 1.2(2) . . . . ?
C8 N1 C1 N2 -178.17(18) . . . . ?
C1 N1 C2 C3 176.4(2) . . . . ?
C8 N1 C2 C3 -4.1(3) . . . . ?
C1 N1 C2 C7 -0.3(2) . . . . ?
C8 N1 C2 C7 179.06(17) . . . . ?
C7 C2 C3 C4 0.1(3) . . . . ?
N1 C2 C3 C4 -176.3(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?
C5 C6 C7 N2 176.9(2) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
N1 C2 C7 C6 176.69(18) . . . . ?
C3 C2 C7 N2 -177.73(18) . . . . ?
N1 C2 C7 N2 -0.6(2) . . . . ?
C1 N2 C7 C6 -175.5(2) . . . . ?
C11 N2 C7 C6 7.4(3) . . . . ?
C1 N2 C7 C2 1.3(2) . . . . ?
C11 N2 C7 C2 -175.73(17) . . . . ?
C1 N1 C8 C10 -15.4(3) . . . . ?
C2 N1 C8 C10 165.29(18) . . . . ?
C1 N1 C8 C9 109.4(2) . . . . ?
C2 N1 C8 C9 -69.8(2) . . . . ?
C1 N2 C11 C13 112.5(2) . . . . ?
C7 N2 C11 C13 -70.9(3) . . . . ?
C1 N2 C11 C12 -120.9(2) . . . . ?
C7 N2 C11 C12 55.7(3) . . . . ?
C19 C14 C15 C16 0.5(3) . . . . ?
B1 C14 C15 C16 178.91(18) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C14 -0.5(3) . . . . ?
C15 C14 C19 C18 -0.1(3) . . . . ?
B1 C14 C19 C18 -178.45(19) . . . . ?
C25 C20 C21 C22 -1.1(3) . . . . ?
B1 C20 C21 C22 176.22(19) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C23 C24 C25 C20 0.1(3) . . . . ?
C21 C20 C25 C24 0.6(3) . . . . ?
B1 C20 C25 C24 -176.70(19) . . . . ?
C31 C26 C27 C28 -1.1(3) . . . . ?
B1 C26 C27 C28 -175.98(19) . . . . ?
C26 C27 C28 C29 -0.8(3) . . . . ?
C27 C28 C29 C30 1.8(3) . . . . ?
C28 C29 C30 C31 -0.7(3) . . . . ?
C29 C30 C31 C26 -1.3(3) . . . . ?
C27 C26 C31 C30 2.2(3) . . . . ?
B1 C26 C31 C30 177.08(19) . . . . ?
C37 C32 C33 C34 -0.5(3) . . . . ?
B1 C32 C33 C34 -178.66(19) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C33 C34 C35 C36 0.6(3) . . . . ?
C34 C35 C36 C37 -0.6(3) . . . . ?
C35 C36 C37 C32 0.0(3) . . . . ?
C33 C32 C37 C36 0.5(3) . . . . ?
B1 C32 C37 C36 178.73(19) . . . . ?
C15 C14 B1 C20 21.1(2) . . . . ?
C19 C14 B1 C20 -160.63(18) . . . . ?
C15 C14 B1 C26 140.60(18) . . . . ?
C19 C14 B1 C26 -41.2(2) . . . . ?
C15 C14 B1 C32 -98.8(2) . . . . ?
C19 C14 B1 C32 79.5(2) . . . . ?
C25 C20 B1 C14 103.1(2) . . . . ?
C21 C20 B1 C14 -73.9(2) . . . . ?
C25 C20 B1 C26 -18.1(2) . . . . ?
C21 C20 B1 C26 164.77(17) . . . . ?
C25 C20 B1 C32 -136.65(19) . . . . ?
C21 C20 B1 C32 46.3(2) . . . . ?
C31 C26 B1 C14 155.37(17) . . . . ?
C27 C26 B1 C14 -30.1(3) . . . . ?
C31 C26 B1 C20 -84.1(2) . . . . ?
C27 C26 B1 C20 90.4(2) . . . . ?
C31 C26 B1 C32 34.5(2) . . . . ?
C27 C26 B1 C32 -151.06(18) . . . . ?
C37 C32 B1 C14 154.36(18) . . . . ?
C33 C32 B1 C14 -27.6(3) . . . . ?
C37 C32 B1 C20 34.0(3) . . . . ?
C33 C32 B1 C20 -147.95(19) . . . . ?
C37 C32 B1 C26 -83.9(2) . . . . ?
C33 C32 B1 C26 94.2(2) . . . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.039



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
