# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2apra
_database_code_depnum_ccdc_archive 'CCDC 1063837'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 B F2 N2 O2'
_chemical_formula_sum            'C21 H25 B F2 N2 O2'
_chemical_formula_weight         386.24

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Cmc2(1)
_symmetry_space_group_name_HALL  'C 2c -2'

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

_cell_length_a                   22.3720(18)
_cell_length_b                   10.6579(9)
_cell_length_c                   8.0526(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1920.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2910
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      27.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6800
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1824
_reflns_number_gt                1636
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT+ 6.45  (Bruker, 2003)'
_computing_structure_solution    Sir92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'diamond 3.1d'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0322P)²+0.7935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(8)
_refine_ls_number_reflns         1824
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0675
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.0000 0.2183(3) 0.4181(4) 0.0215(6) Uani 1 2 d S . .
C1 C 0.0000 0.1868(2) 0.8651(3) 0.0128(5) Uani 1 2 d S . .
H1 H 0.0000 0.1315 0.9544 0.015 Uiso 1 2 calc SR . .
C2 C 0.03466(7) 0.31649(16) 0.6569(2) 0.0167(4) Uani 1 1 d . . .
H2 H 0.0505 0.4008 0.6781 0.020 Uiso 1 1 calc R . .
C4 C 0.11026(7) 0.20768(15) 0.8477(2) 0.0135(4) Uani 1 1 d . . .
C5 C 0.13708(7) 0.29638(14) 0.9502(2) 0.0161(4) Uani 1 1 d . . .
C6 C 0.19732(7) 0.28208(16) 0.9851(2) 0.0189(4) Uani 1 1 d . . .
H6 H 0.2161 0.3411 1.0523 0.023 Uiso 1 1 calc R . .
C7 C 0.23061(7) 0.18280(16) 0.9231(2) 0.0192(4) Uani 1 1 d . . .
C8 C 0.20143(7) 0.09414(16) 0.8265(2) 0.0169(4) Uani 1 1 d . . .
H8 H 0.2229 0.0252 0.7881 0.020 Uiso 1 1 calc R . .
C9 C 0.14116(7) 0.10456(15) 0.7849(2) 0.0142(4) Uani 1 1 d . . .
C10 C 0.10187(8) 0.40262(16) 1.0266(2) 0.0213(4) Uani 1 1 d . . .
H10A H 0.0884 0.4583 0.9406 0.032 Uiso 1 1 calc R . .
H10B H 0.1268 0.4478 1.1029 0.032 Uiso 1 1 calc R . .
H10C H 0.0679 0.3693 1.0847 0.032 Uiso 1 1 calc R . .
C11 C 0.29629(8) 0.17194(19) 0.9615(3) 0.0298(5) Uani 1 1 d . . .
H11A H 0.3121 0.0982 0.9092 0.045 Uiso 1 1 calc R . .
H11B H 0.3018 0.1660 1.0795 0.045 Uiso 1 1 calc R . .
H11C H 0.3168 0.2447 0.9204 0.045 Uiso 1 1 calc R . .
C12 C 0.11162(7) 0.00685(17) 0.6786(2) 0.0199(4) Uani 1 1 d . . .
H12A H 0.1401 -0.0574 0.6514 0.030 Uiso 1 1 calc R . .
H12B H 0.0972 0.0450 0.5783 0.030 Uiso 1 1 calc R . .
H12C H 0.0787 -0.0295 0.7381 0.030 Uiso 1 1 calc R . .
F1 F 0.0000 0.08792(13) 0.4328(2) 0.0252(4) Uani 1 2 d S . .
F2 F 0.0000 0.24853(16) 0.25081(19) 0.0310(4) Uani 1 2 d S . .
N1 N 0.04924(6) 0.22918(12) 0.79663(18) 0.0145(3) Uani 1 1 d . . .
O1 O 0.05206(5) 0.27346(11) 0.50420(16) 0.0188(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F2 1.385(3) . ?
B1 F1 1.395(3) . ?
B1 O1 1.477(2) 4 ?
B1 O1 1.477(2) . ?
C1 N1 1.3119(19) . ?
C1 N1 1.3119(19) 4 ?
C1 H1 0.9300 . ?
C2 O1 1.369(2) . ?
C2 N1 1.496(2) . ?
C2 C2 1.551(3) 4 ?
C2 H2 0.9800 . ?
C4 C5 1.391(2) . ?
C4 C9 1.394(2) . ?
C4 N1 1.444(2) . ?
C5 C6 1.385(2) . ?
C5 C10 1.510(2) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(3) . ?
C7 C11 1.506(2) . ?
C8 C9 1.394(2) . ?
C8 H8 0.9300 . ?
C9 C12 1.501(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
F2 B1 F1 108.3(2) . . ?
F2 B1 O1 111.33(15) . 4 ?
F1 B1 O1 110.91(15) . 4 ?
F2 B1 O1 111.33(15) . . ?
F1 B1 O1 110.91(15) . . ?
O1 B1 O1 104.1(2) 4 . ?
N1 C1 N1 114.2(2) . 4 ?
N1 C1 H1 122.9 . . ?
N1 C1 H1 122.9 4 . ?
O1 C2 N1 113.90(13) . . ?
O1 C2 C2 106.51(8) . 4 ?
N1 C2 C2 102.59(8) . 4 ?
O1 C2 H2 111.1 . . ?
N1 C2 H2 111.1 . . ?
C2 C2 H2 111.1 4 . ?
C5 C4 C9 122.52(14) . . ?
C5 C4 N1 117.97(14) . . ?
C9 C4 N1 119.37(14) . . ?
C6 C5 C4 117.72(14) . . ?
C6 C5 C10 120.49(16) . . ?
C4 C5 C10 121.75(15) . . ?
C5 C6 C7 122.25(16) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C8 117.95(15) . . ?
C6 C7 C11 120.59(16) . . ?
C8 C7 C11 121.46(16) . . ?
C7 C8 C9 122.41(15) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C4 C9 C8 117.08(15) . . ?
C4 C9 C12 122.40(14) . . ?
C8 C9 C12 120.51(15) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C4 128.28(16) . . ?
C1 N1 C2 110.30(14) . . ?
C4 N1 C2 121.27(12) . . ?
C2 O1 B1 109.31(14) . . ?

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
C9 C4 C5 C6 2.2(2) . . . . ?
N1 C4 C5 C6 -173.56(15) . . . . ?
C9 C4 C5 C10 -175.77(16) . . . . ?
N1 C4 C5 C10 8.5(2) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C10 C5 C6 C7 177.19(17) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C5 C6 C7 C11 178.89(18) . . . . ?
C6 C7 C8 C9 2.7(3) . . . . ?
C11 C7 C8 C9 -177.79(16) . . . . ?
C5 C4 C9 C8 -1.1(2) . . . . ?
N1 C4 C9 C8 174.53(15) . . . . ?
C5 C4 C9 C12 178.06(16) . . . . ?
N1 C4 C9 C12 -6.3(2) . . . . ?
C7 C8 C9 C4 -1.4(2) . . . . ?
C7 C8 C9 C12 179.43(17) . . . . ?
N1 C1 N1 C4 175.77(11) 4 . . . ?
N1 C1 N1 C2 0.3(3) 4 . . . ?
C5 C4 N1 C1 -94.7(2) . . . . ?
C9 C4 N1 C1 89.5(2) . . . . ?
C5 C4 N1 C2 80.39(19) . . . . ?
C9 C4 N1 C2 -95.47(18) . . . . ?
O1 C2 N1 C1 -114.84(17) . . . . ?
C2 C2 N1 C1 -0.16(15) 4 . . . ?
O1 C2 N1 C4 69.30(19) . . . . ?
C2 C2 N1 C4 -176.01(12) 4 . . . ?
N1 C2 O1 B1 99.55(17) . . . . ?
C2 C2 O1 B1 -12.79(15) 4 . . . ?
F2 B1 O1 C2 140.22(17) . . . . ?
F1 B1 O1 C2 -99.13(19) . . . . ?
O1 B1 O1 C2 20.2(2) 4 . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_28apram
_database_code_depnum_ccdc_archive 'CCDC 1063838'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N2 O2 S, C4 H8 O2'
_chemical_formula_sum            'C25 H34 N2 O4 S'
_chemical_formula_weight         458.61

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   7.1062(9)
_cell_length_b                   22.149(3)
_cell_length_c                   16.237(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.192(2)
_cell_angle_gamma                90.00
_cell_volume                     2522.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2602
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.12

_exptl_crystal_description       block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13571
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4674
_reflns_number_gt                3415
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT+ 6.45  (Bruker, 2003)'
_computing_structure_solution    Sir92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'diamond 3.1d'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0654P)²+1.1316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4674
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8906(3) 0.04073(10) 0.24384(14) 0.0243(5) Uani 1 1 d . . .
C2 C 1.0742(3) 0.11225(11) 0.18705(15) 0.0251(5) Uani 1 1 d . . .
H2 H 1.0918 0.1176 0.1276 0.030 Uiso 1 1 calc R . .
C3 C 1.2068(3) 0.06304(11) 0.22949(14) 0.0251(5) Uani 1 1 d . . .
H3 H 1.3091 0.0811 0.2718 0.030 Uiso 1 1 calc R . .
C4 C 1.1409(3) -0.01687(11) 0.33472(14) 0.0238(5) Uani 1 1 d . . .
C5 C 1.1506(3) -0.07800(11) 0.31396(15) 0.0273(5) Uani 1 1 d . . .
C6 C 1.2085(3) -0.11851(12) 0.37770(16) 0.0328(6) Uani 1 1 d . . .
H6 H 1.2147 -0.1602 0.3647 0.039 Uiso 1 1 calc R . .
C7 C 1.2580(3) -0.10022(12) 0.46047(16) 0.0317(6) Uani 1 1 d . . .
C8 C 1.2500(3) -0.03911(12) 0.47814(15) 0.0317(6) Uani 1 1 d . . .
H8 H 1.2858 -0.0259 0.5341 0.038 Uiso 1 1 calc R . .
C9 C 1.1912(3) 0.00338(11) 0.41635(15) 0.0254(5) Uani 1 1 d . . .
C10 C 1.0924(4) -0.09986(12) 0.22581(17) 0.0413(7) Uani 1 1 d . . .
H10A H 1.1133 -0.1435 0.2235 0.062 Uiso 1 1 calc R . .
H10B H 1.1689 -0.0793 0.1892 0.062 Uiso 1 1 calc R . .
H10C H 0.9571 -0.0910 0.2074 0.062 Uiso 1 1 calc R . .
C11 C 1.3121(4) -0.14583(14) 0.52868(18) 0.0470(8) Uani 1 1 d . . .
H11A H 1.3289 -0.1255 0.5829 0.070 Uiso 1 1 calc R . .
H11B H 1.4316 -0.1656 0.5212 0.070 Uiso 1 1 calc R . .
H11C H 1.2110 -0.1762 0.5264 0.070 Uiso 1 1 calc R . .
C12 C 1.1773(4) 0.06903(12) 0.43824(17) 0.0374(6) Uani 1 1 d . . .
H12A H 1.1855 0.0732 0.4988 0.056 Uiso 1 1 calc R . .
H12B H 1.0552 0.0853 0.4105 0.056 Uiso 1 1 calc R . .
H12C H 1.2820 0.0913 0.4197 0.056 Uiso 1 1 calc R . .
C13 C 0.7163(3) 0.10679(10) 0.13503(14) 0.0228(5) Uani 1 1 d . . .
C14 C 0.5990(3) 0.15329(10) 0.15655(14) 0.0234(5) Uani 1 1 d . . .
C15 C 0.4411(3) 0.16971(10) 0.09778(14) 0.0253(5) Uani 1 1 d . . .
H15 H 0.3608 0.2015 0.1107 0.030 Uiso 1 1 calc R . .
C16 C 0.3986(3) 0.14095(11) 0.02135(15) 0.0267(5) Uani 1 1 d . . .
C17 C 0.5189(3) 0.09539(11) 0.00199(15) 0.0267(5) Uani 1 1 d . . .
H17 H 0.4909 0.0757 -0.0505 0.032 Uiso 1 1 calc R . .
C18 C 0.6792(3) 0.07800(10) 0.05772(14) 0.0245(5) Uani 1 1 d . . .
C19 C 0.6349(4) 0.18361(12) 0.24033(15) 0.0323(6) Uani 1 1 d . . .
H19A H 0.5129 0.1932 0.2581 0.048 Uiso 1 1 calc R . .
H19B H 0.7072 0.2209 0.2364 0.048 Uiso 1 1 calc R . .
H19C H 0.7081 0.1565 0.2811 0.048 Uiso 1 1 calc R . .
C20 C 0.2200(4) 0.15700(12) -0.03848(16) 0.0363(6) Uani 1 1 d . . .
H20A H 0.1200 0.1274 -0.0333 0.054 Uiso 1 1 calc R . .
H20B H 0.2475 0.1566 -0.0957 0.054 Uiso 1 1 calc R . .
H20C H 0.1767 0.1973 -0.0252 0.054 Uiso 1 1 calc R . .
C21 C 0.8083(4) 0.02877(11) 0.03604(16) 0.0325(6) Uani 1 1 d . . .
H21A H 0.7589 0.0129 -0.0196 0.049 Uiso 1 1 calc R . .
H21B H 0.8137 -0.0038 0.0772 0.049 Uiso 1 1 calc R . .
H21C H 0.9366 0.0451 0.0363 0.049 Uiso 1 1 calc R . .
C22 C 0.3159(4) 0.15891(14) 0.65734(19) 0.0472(7) Uani 1 1 d . . .
H22A H 0.3883 0.1233 0.6450 0.071 Uiso 1 1 calc R . .
H22B H 0.1795 0.1493 0.6482 0.071 Uiso 1 1 calc R . .
H22C H 0.3560 0.1708 0.7156 0.071 Uiso 1 1 calc R . .
C23 C 0.3523(4) 0.20975(12) 0.60126(18) 0.0379(6) Uani 1 1 d . . .
C24 C 0.2571(4) 0.25780(12) 0.47091(18) 0.0392(7) Uani 1 1 d . . .
H24A H 0.3838 0.2543 0.4534 0.047 Uiso 1 1 calc R . .
H24B H 0.2487 0.2977 0.4975 0.047 Uiso 1 1 calc R . .
C25 C 0.1037(5) 0.25181(13) 0.39697(18) 0.0493(8) Uani 1 1 d . . .
H25A H 0.1168 0.2130 0.3695 0.074 Uiso 1 1 calc R . .
H25B H 0.1147 0.2847 0.3577 0.074 Uiso 1 1 calc R . .
H25C H -0.0212 0.2538 0.4152 0.074 Uiso 1 1 calc R . .
N1 N 1.0760(3) 0.02638(9) 0.27052(12) 0.0240(4) Uani 1 1 d . . .
N2 N 0.8832(3) 0.08881(9) 0.19208(12) 0.0237(4) Uani 1 1 d . . .
O1 O 1.1127(2) 0.16624(7) 0.23186(10) 0.0297(4) Uani 1 1 d . . .
H1 H 1.0711 0.1956 0.2015 0.045 Uiso 1 1 calc R . .
O2 O 1.2865(2) 0.02884(8) 0.17107(10) 0.0297(4) Uani 1 1 d . . .
H2A H 1.4043 0.0252 0.1871 0.045 Uiso 1 1 calc R . .
O3 O 0.4795(3) 0.24686(8) 0.61667(13) 0.0425(5) Uani 1 1 d . . .
O4 O 0.2320(2) 0.20965(8) 0.52987(12) 0.0384(5) Uani 1 1 d . . .
S1 S 0.70303(8) 0.00403(3) 0.27149(4) 0.02904(19) 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
C1 N2 1.352(3) . ?
C1 N1 1.357(3) . ?
C1 S1 1.682(2) . ?
C2 O1 1.404(3) . ?
C2 N2 1.467(3) . ?
C2 C3 1.531(3) . ?
C2 H2 1.0000 . ?
C3 O2 1.402(3) . ?
C3 N1 1.471(3) . ?
C3 H3 1.0000 . ?
C4 C9 1.391(3) . ?
C4 C5 1.400(3) . ?
C4 N1 1.437(3) . ?
C5 C6 1.382(3) . ?
C5 C10 1.505(3) . ?
C6 C7 1.394(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(4) . ?
C7 C11 1.503(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C12 1.504(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.395(3) . ?
C13 C14 1.404(3) . ?
C13 N2 1.440(3) . ?
C14 C15 1.400(3) . ?
C14 C19 1.502(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(3) . ?
C16 C20 1.512(3) . ?
C17 C18 1.392(3) . ?
C17 H17 0.9500 . ?
C18 C21 1.503(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.496(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 O3 1.218(3) . ?
C23 O4 1.326(3) . ?
C24 O4 1.463(3) . ?
C24 C25 1.493(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O1 H1 0.8400 . ?
O2 H2A 0.8400 . ?

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
N2 C1 N1 108.8(2) . . ?
N2 C1 S1 126.35(17) . . ?
N1 C1 S1 124.87(18) . . ?
O1 C2 N2 112.21(19) . . ?
O1 C2 C3 108.55(18) . . ?
N2 C2 C3 103.37(18) . . ?
O1 C2 H2 110.8 . . ?
N2 C2 H2 110.8 . . ?
C3 C2 H2 110.8 . . ?
O2 C3 N1 111.16(19) . . ?
O2 C3 C2 111.49(19) . . ?
N1 C3 C2 102.06(17) . . ?
O2 C3 H3 110.6 . . ?
N1 C3 H3 110.6 . . ?
C2 C3 H3 110.6 . . ?
C9 C4 C5 121.8(2) . . ?
C9 C4 N1 118.7(2) . . ?
C5 C4 N1 119.5(2) . . ?
C6 C5 C4 117.9(2) . . ?
C6 C5 C10 120.5(2) . . ?
C4 C5 C10 121.6(2) . . ?
C5 C6 C7 122.2(2) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C8 C7 C6 118.1(2) . . ?
C8 C7 C11 121.2(2) . . ?
C6 C7 C11 120.7(2) . . ?
C7 C8 C9 121.9(2) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C4 118.1(2) . . ?
C8 C9 C12 120.5(2) . . ?
C4 C9 C12 121.4(2) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 121.7(2) . . ?
C18 C13 N2 118.0(2) . . ?
C14 C13 N2 120.2(2) . . ?
C15 C14 C13 117.6(2) . . ?
C15 C14 C19 120.2(2) . . ?
C13 C14 C19 122.1(2) . . ?
C16 C15 C14 121.9(2) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 118.8(2) . . ?
C15 C16 C20 120.5(2) . . ?
C17 C16 C20 120.6(2) . . ?
C16 C17 C18 121.5(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 118.4(2) . . ?
C17 C18 C21 121.0(2) . . ?
C13 C18 C21 120.5(2) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 O4 122.3(3) . . ?
O3 C23 C22 125.3(3) . . ?
O4 C23 C22 112.4(2) . . ?
O4 C24 C25 108.2(2) . . ?
O4 C24 H24A 110.1 . . ?
C25 C24 H24A 110.1 . . ?
O4 C24 H24B 110.1 . . ?
C25 C24 H24B 110.1 . . ?
H24A C24 H24B 108.4 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C4 124.80(19) . . ?
C1 N1 C3 112.17(18) . . ?
C4 N1 C3 122.94(18) . . ?
C1 N2 C13 124.30(19) . . ?
C1 N2 C2 111.66(18) . . ?
C13 N2 C2 122.72(18) . . ?
C2 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C23 O4 C24 116.2(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
O1 C2 C3 O2 -135.38(19) . . . . ?
N2 C2 C3 O2 105.3(2) . . . . ?
O1 C2 C3 N1 105.9(2) . . . . ?
N2 C2 C3 N1 -13.4(2) . . . . ?
C9 C4 C5 C6 1.3(4) . . . . ?
N1 C4 C5 C6 -178.2(2) . . . . ?
C9 C4 C5 C10 178.8(2) . . . . ?
N1 C4 C5 C10 -0.7(3) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C10 C5 C6 C7 -178.0(2) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C5 C6 C7 C11 177.3(2) . . . . ?
C6 C7 C8 C9 1.3(4) . . . . ?
C11 C7 C8 C9 -176.8(2) . . . . ?
C7 C8 C9 C4 -0.5(4) . . . . ?
C7 C8 C9 C12 177.7(2) . . . . ?
C5 C4 C9 C8 -0.8(3) . . . . ?
N1 C4 C9 C8 178.7(2) . . . . ?
C5 C4 C9 C12 -179.0(2) . . . . ?
N1 C4 C9 C12 0.5(3) . . . . ?
C18 C13 C14 C15 0.6(3) . . . . ?
N2 C13 C14 C15 178.59(19) . . . . ?
C18 C13 C14 C19 178.5(2) . . . . ?
N2 C13 C14 C19 -3.5(3) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C19 C14 C15 C16 -177.1(2) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C14 C15 C16 C20 176.0(2) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C20 C16 C17 C18 -177.0(2) . . . . ?
C16 C17 C18 C13 1.0(3) . . . . ?
C16 C17 C18 C21 -179.9(2) . . . . ?
C14 C13 C18 C17 -1.5(3) . . . . ?
N2 C13 C18 C17 -179.6(2) . . . . ?
C14 C13 C18 C21 179.4(2) . . . . ?
N2 C13 C18 C21 1.3(3) . . . . ?
N2 C1 N1 C4 171.2(2) . . . . ?
S1 C1 N1 C4 -8.8(3) . . . . ?
N2 C1 N1 C3 -5.4(3) . . . . ?
S1 C1 N1 C3 174.65(17) . . . . ?
C9 C4 N1 C1 -93.4(3) . . . . ?
C5 C4 N1 C1 86.1(3) . . . . ?
C9 C4 N1 C3 82.8(3) . . . . ?
C5 C4 N1 C3 -97.7(3) . . . . ?
O2 C3 N1 C1 -106.9(2) . . . . ?
C2 C3 N1 C1 12.1(2) . . . . ?
O2 C3 N1 C4 76.5(3) . . . . ?
C2 C3 N1 C4 -164.6(2) . . . . ?
N1 C1 N2 C13 162.7(2) . . . . ?
S1 C1 N2 C13 -17.3(3) . . . . ?
N1 C1 N2 C2 -4.4(3) . . . . ?
S1 C1 N2 C2 175.55(17) . . . . ?
C18 C13 N2 C1 -83.5(3) . . . . ?
C14 C13 N2 C1 98.5(3) . . . . ?
C18 C13 N2 C2 82.3(3) . . . . ?
C14 C13 N2 C2 -95.8(3) . . . . ?
O1 C2 N2 C1 -105.1(2) . . . . ?
C3 C2 N2 C1 11.6(2) . . . . ?
O1 C2 N2 C13 87.5(3) . . . . ?
C3 C2 N2 C13 -155.7(2) . . . . ?
O3 C23 O4 C24 -1.6(4) . . . . ?
C22 C23 O4 C24 -179.9(2) . . . . ?
C25 C24 O4 C23 -177.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.264
_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_10jula_0m
_database_code_depnum_ccdc_archive 'CCDC 1063839'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N2 O2 Se'
_chemical_formula_sum            'C21 H26 N2 O2 Se'
_chemical_formula_weight         417.40

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_HALL  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.417(5)
_cell_length_b                   11.759(5)
_cell_length_c                   15.714(5)
_cell_angle_alpha                106.783(5)
_cell_angle_beta                 98.029(5)
_cell_angle_gamma                97.972(5)
_cell_volume                     1275.9(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4965
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.52

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    1.485
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_T_max  0.7556
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12356
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4713
_reflns_number_gt                3382
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4713
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3028(3) 0.5058(2) 0.25200(16) 0.0391(6) Uani 1 1 d . . .
C2 C 0.1522(4) 0.6671(2) 0.25992(19) 0.0480(7) Uani 1 1 d . . .
H2 H 0.0983 0.6960 0.2113 0.058 Uiso 1 1 calc R . .
C3 C 0.0181(4) 0.5616(3) 0.26830(18) 0.0462(7) Uani 1 1 d . . .
H3 H -0.0341 0.5864 0.3233 0.055 Uiso 1 1 calc R . .
C4 C 0.0941(3) 0.3792(2) 0.31226(17) 0.0423(6) Uani 1 1 d . . .
C5 C 0.1462(4) 0.4039(3) 0.40452(19) 0.0482(7) Uani 1 1 d . . .
C6 C 0.0975(4) 0.3115(3) 0.4402(2) 0.0587(8) Uani 1 1 d . . .
H6 H 0.1295 0.3268 0.5024 0.070 Uiso 1 1 calc R . .
C7 C 0.0034(4) 0.1977(3) 0.3871(2) 0.0589(8) Uani 1 1 d . . .
C8 C -0.0443(4) 0.1776(3) 0.2953(2) 0.0604(8) Uani 1 1 d . . .
H8 H -0.1080 0.1015 0.2585 0.073 Uiso 1 1 calc R . .
C9 C -0.0007(4) 0.2665(3) 0.25580(18) 0.0511(7) Uani 1 1 d . . .
C10 C 0.2530(5) 0.5256(3) 0.4645(2) 0.0683(9) Uani 1 1 d . . .
H10A H 0.3691 0.5423 0.4460 0.102 Uiso 1 1 calc R . .
H10B H 0.2757 0.5254 0.5261 0.102 Uiso 1 1 calc R . .
H10C H 0.1823 0.5868 0.4598 0.102 Uiso 1 1 calc R . .
C11 C -0.0411(6) 0.0989(3) 0.4281(3) 0.0853(11) Uani 1 1 d . . .
H11A H 0.0647 0.0614 0.4350 0.128 Uiso 1 1 calc R . .
H11B H -0.1443 0.0395 0.3893 0.128 Uiso 1 1 calc R . .
H11C H -0.0721 0.1327 0.4864 0.128 Uiso 1 1 calc R . .
C12 C -0.0548(6) 0.2394(3) 0.1552(2) 0.0838(11) Uani 1 1 d . . .
H12A H -0.0483 0.1569 0.1252 0.126 Uiso 1 1 calc R . .
H12B H 0.0283 0.2923 0.1355 0.126 Uiso 1 1 calc R . .
H12C H -0.1792 0.2518 0.1407 0.126 Uiso 1 1 calc R . .
C13 C 0.4471(3) 0.6647(2) 0.19512(17) 0.0382(6) Uani 1 1 d . . .
C14 C 0.6111(4) 0.7399(2) 0.24781(17) 0.0423(6) Uani 1 1 d . . .
C15 C 0.7346(4) 0.7877(2) 0.2033(2) 0.0511(7) Uani 1 1 d . . .
H15 H 0.8453 0.8375 0.2373 0.061 Uiso 1 1 calc R . .
C16 C 0.7015(4) 0.7653(3) 0.1118(2) 0.0555(8) Uani 1 1 d . . .
C17 C 0.5390(5) 0.6909(3) 0.06232(19) 0.0586(8) Uani 1 1 d . . .
H17 H 0.5154 0.6746 -0.0001 0.070 Uiso 1 1 calc R . .
C18 C 0.4082(4) 0.6390(2) 0.10204(18) 0.0483(7) Uani 1 1 d . . .
C19 C 0.6540(4) 0.7645(3) 0.34828(19) 0.0650(8) Uani 1 1 d . . .
H19A H 0.5845 0.8226 0.3770 0.097 Uiso 1 1 calc R . .
H19B H 0.7842 0.7959 0.3703 0.097 Uiso 1 1 calc R . .
H19C H 0.6210 0.6907 0.3619 0.097 Uiso 1 1 calc R . .
C20 C 0.8395(6) 0.8187(4) 0.0654(3) 0.0896(12) Uani 1 1 d . . .
H20A H 0.8744 0.9043 0.0949 0.134 Uiso 1 1 calc R . .
H20B H 0.7845 0.8033 0.0031 0.134 Uiso 1 1 calc R . .
H20C H 0.9474 0.7823 0.0685 0.134 Uiso 1 1 calc R . .
C21 C 0.2315(5) 0.5566(3) 0.0450(2) 0.0720(9) Uani 1 1 d . . .
H21A H 0.2189 0.4809 0.0575 0.108 Uiso 1 1 calc R . .
H21B H 0.2357 0.5425 -0.0179 0.108 Uiso 1 1 calc R . .
H21C H 0.1275 0.5938 0.0591 0.108 Uiso 1 1 calc R . .
N1 N 0.1399(3) 0.47585(18) 0.27459(14) 0.0431(5) Uani 1 1 d . . .
N2 N 0.3131(3) 0.61358(18) 0.23756(14) 0.0421(5) Uani 1 1 d . . .
O1 O 0.1939(3) 0.75980(19) 0.34308(15) 0.0734(6) Uani 1 1 d . . .
H1 H 0.2418 0.8228 0.3361 0.110 Uiso 1 1 calc R . .
O2 O -0.1213(3) 0.5160(2) 0.19197(14) 0.0652(6) Uani 1 1 d . . .
H2A H -0.2224 0.5099 0.2074 0.098 Uiso 1 1 calc R . .
Se1 Se 0.48090(4) 0.41149(3) 0.24151(2) 0.05801(15) 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
C1 N1 1.335(3) . ?
C1 N2 1.345(3) . ?
C1 Se1 1.834(3) . ?
C2 O1 1.401(3) . ?
C2 N2 1.464(3) . ?
C2 C3 1.528(4) . ?
C2 H2 0.9800 . ?
C3 O2 1.387(3) . ?
C3 N1 1.459(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.380(4) . ?
C4 C9 1.389(4) . ?
C4 N1 1.447(3) . ?
C5 C6 1.388(4) . ?
C5 C10 1.504(4) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(4) . ?
C7 C11 1.504(4) . ?
C8 C9 1.385(4) . ?
C8 H8 0.9300 . ?
C9 C12 1.502(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.384(3) . ?
C13 C14 1.394(4) . ?
C13 N2 1.430(3) . ?
C14 C15 1.381(4) . ?
C14 C19 1.499(4) . ?
C15 C16 1.365(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(4) . ?
C16 C20 1.507(4) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C18 C21 1.509(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O1 H1 0.8200 . ?
O2 H2A 0.8200 . ?

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
N1 C1 N2 109.4(2) . . ?
N1 C1 Se1 124.36(18) . . ?
N2 C1 Se1 126.20(19) . . ?
O1 C2 N2 112.5(2) . . ?
O1 C2 C3 108.6(2) . . ?
N2 C2 C3 103.1(2) . . ?
O1 C2 H2 110.8 . . ?
N2 C2 H2 110.8 . . ?
C3 C2 H2 110.8 . . ?
O2 C3 N1 112.0(2) . . ?
O2 C3 C2 110.1(2) . . ?
N1 C3 C2 101.7(2) . . ?
O2 C3 H3 110.9 . . ?
N1 C3 H3 110.9 . . ?
C2 C3 H3 110.9 . . ?
C5 C4 C9 122.3(2) . . ?
C5 C4 N1 117.9(2) . . ?
C9 C4 N1 119.8(2) . . ?
C4 C5 C6 117.4(3) . . ?
C4 C5 C10 121.7(3) . . ?
C6 C5 C10 120.9(3) . . ?
C7 C6 C5 122.7(3) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C8 C7 C6 117.6(3) . . ?
C8 C7 C11 121.4(3) . . ?
C6 C7 C11 120.9(3) . . ?
C7 C8 C9 122.4(3) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C8 C9 C4 117.6(3) . . ?
C8 C9 C12 120.2(3) . . ?
C4 C9 C12 122.1(2) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 121.8(2) . . ?
C18 C13 N2 118.5(2) . . ?
C14 C13 N2 119.8(2) . . ?
C15 C14 C13 117.3(2) . . ?
C15 C14 C19 121.4(3) . . ?
C13 C14 C19 121.3(2) . . ?
C16 C15 C14 122.9(3) . . ?
C16 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C15 C16 C17 118.1(3) . . ?
C15 C16 C20 121.6(3) . . ?
C17 C16 C20 120.3(3) . . ?
C16 C17 C18 122.4(3) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C13 C18 C17 117.6(3) . . ?
C13 C18 C21 121.7(3) . . ?
C17 C18 C21 120.8(3) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C4 124.9(2) . . ?
C1 N1 C3 112.4(2) . . ?
C4 N1 C3 122.2(2) . . ?
C1 N2 C13 126.0(2) . . ?
C1 N2 C2 110.9(2) . . ?
C13 N2 C2 122.6(2) . . ?
C2 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.499 0.000 0.054 338 82 ' '
_platon_squeeze_details          
;
;

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
O1 C2 C3 O2 136.8(2) . . . . ?
N2 C2 C3 O2 -103.8(2) . . . . ?
O1 C2 C3 N1 -104.4(2) . . . . ?
N2 C2 C3 N1 15.1(3) . . . . ?
C9 C4 C5 C6 -1.1(4) . . . . ?
N1 C4 C5 C6 178.4(2) . . . . ?
C9 C4 C5 C10 178.5(3) . . . . ?
N1 C4 C5 C10 -2.0(4) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C10 C5 C6 C7 -178.4(3) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C5 C6 C7 C11 177.9(3) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C11 C7 C8 C9 -178.4(3) . . . . ?
C7 C8 C9 C4 -0.1(5) . . . . ?
C7 C8 C9 C12 179.6(3) . . . . ?
C5 C4 C9 C8 0.6(4) . . . . ?
N1 C4 C9 C8 -178.9(2) . . . . ?
C5 C4 C9 C12 -179.1(3) . . . . ?
N1 C4 C9 C12 1.4(4) . . . . ?
C18 C13 C14 C15 -0.2(4) . . . . ?
N2 C13 C14 C15 -179.4(2) . . . . ?
C18 C13 C14 C19 -178.3(3) . . . . ?
N2 C13 C14 C19 2.5(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C19 C14 C15 C16 178.7(3) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C14 C15 C16 C20 -179.8(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C20 C16 C17 C18 179.6(3) . . . . ?
C14 C13 C18 C17 0.0(4) . . . . ?
N2 C13 C18 C17 179.1(2) . . . . ?
C14 C13 C18 C21 179.4(3) . . . . ?
N2 C13 C18 C21 -1.5(4) . . . . ?
C16 C17 C18 C13 -0.1(4) . . . . ?
C16 C17 C18 C21 -179.5(3) . . . . ?
N2 C1 N1 C4 -167.0(2) . . . . ?
Se1 C1 N1 C4 13.7(4) . . . . ?
N2 C1 N1 C3 5.5(3) . . . . ?
Se1 C1 N1 C3 -173.84(18) . . . . ?
C5 C4 N1 C1 84.1(3) . . . . ?
C9 C4 N1 C1 -96.4(3) . . . . ?
C5 C4 N1 C3 -87.7(3) . . . . ?
C9 C4 N1 C3 91.8(3) . . . . ?
O2 C3 N1 C1 104.2(2) . . . . ?
C2 C3 N1 C1 -13.3(3) . . . . ?
O2 C3 N1 C4 -83.1(3) . . . . ?
C2 C3 N1 C4 159.5(2) . . . . ?
N1 C1 N2 C13 -166.6(2) . . . . ?
Se1 C1 N2 C13 12.7(4) . . . . ?
N1 C1 N2 C2 5.6(3) . . . . ?
Se1 C1 N2 C2 -175.11(18) . . . . ?
C18 C13 N2 C1 89.1(3) . . . . ?
C14 C13 N2 C1 -91.7(3) . . . . ?
C18 C13 N2 C2 -82.2(3) . . . . ?
C14 C13 N2 C2 96.9(3) . . . . ?
O1 C2 N2 C1 103.3(3) . . . . ?
C3 C2 N2 C1 -13.4(3) . . . . ?
O1 C2 N2 C13 -84.2(3) . . . . ?
C3 C2 N2 C13 159.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_3jula_0m
_database_code_depnum_ccdc_archive 'CCDC 1063840'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H29 B N2 O2 S'
_chemical_formula_sum            'C27 H29 B N2 O2 S'
_chemical_formula_weight         456.40

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '
_symmetry_space_group_name_HALL  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   14.6181(19)
_cell_length_b                   11.4652(14)
_cell_length_c                   15.805(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.013(4)
_cell_angle_gamma                90.00
_cell_volume                     2533.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1531
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      20.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11555
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_sigmaI/netI    0.2001
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4964
_reflns_number_gt                1618
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0513P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4964
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2440
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.2587(4) 0.0561(4) 0.9674(4) 0.0566(14) Uani 1 1 d . . .
C1 C 0.1788(3) 0.3282(3) 0.8389(3) 0.0504(11) Uani 1 1 d . . .
C2 C 0.2325(3) 0.1378(3) 0.8316(3) 0.0576(12) Uani 1 1 d . . .
H2 H 0.2266 0.0955 0.7764 0.069 Uiso 1 1 calc R . .
C3 C 0.1396(3) 0.1345(3) 0.8574(3) 0.0550(11) Uani 1 1 d . . .
H3 H 0.0897 0.0903 0.8144 0.066 Uiso 1 1 calc R . .
C4 C 0.0261(3) 0.2896(3) 0.8754(3) 0.0490(11) Uani 1 1 d . . .
C5 C 0.0272(3) 0.3246(3) 0.9591(3) 0.0561(12) Uani 1 1 d . . .
C6 C -0.0600(4) 0.3502(3) 0.9741(3) 0.0663(13) Uani 1 1 d . . .
H6 H -0.0606 0.3748 1.0300 0.080 Uiso 1 1 calc R . .
C7 C -0.1452(4) 0.3400(4) 0.9080(4) 0.0689(14) Uani 1 1 d . . .
C8 C -0.1430(3) 0.3062(3) 0.8249(3) 0.0677(13) Uani 1 1 d . . .
H8 H -0.2004 0.3004 0.7799 0.081 Uiso 1 1 calc R . .
C9 C -0.0582(4) 0.2804(3) 0.8061(3) 0.0570(12) Uani 1 1 d . . .
C10 C 0.1197(3) 0.3353(3) 1.0335(3) 0.0787(14) Uani 1 1 d . . .
H10A H 0.1069 0.3703 1.0840 0.118 Uiso 1 1 calc R . .
H10B H 0.1638 0.3833 1.0145 0.118 Uiso 1 1 calc R . .
H10C H 0.1469 0.2593 1.0490 0.118 Uiso 1 1 calc R . .
C11 C -0.2398(3) 0.3674(4) 0.9242(3) 0.0963(17) Uani 1 1 d . . .
H11A H -0.2287 0.3936 0.9841 0.144 Uiso 1 1 calc R . .
H11B H -0.2789 0.2985 0.9146 0.144 Uiso 1 1 calc R . .
H11C H -0.2720 0.4276 0.8842 0.144 Uiso 1 1 calc R . .
C12 C -0.0591(3) 0.2469(4) 0.7137(3) 0.0776(14) Uani 1 1 d . . .
H12A H -0.1212 0.2624 0.6735 0.116 Uiso 1 1 calc R . .
H12B H -0.0449 0.1653 0.7121 0.116 Uiso 1 1 calc R . .
H12C H -0.0119 0.2916 0.6966 0.116 Uiso 1 1 calc R . .
C13 C 0.3209(4) 0.3022(3) 0.7859(4) 0.0578(12) Uani 1 1 d . . .
C14 C 0.3011(4) 0.3003(3) 0.6943(4) 0.0647(13) Uani 1 1 d . . .
C15 C 0.3742(5) 0.3323(4) 0.6591(4) 0.0826(16) Uani 1 1 d . . .
H15 H 0.3637 0.3294 0.5982 0.099 Uiso 1 1 calc R . .
C16 C 0.4621(5) 0.3683(4) 0.7128(5) 0.0845(19) Uani 1 1 d . . .
C17 C 0.4771(4) 0.3748(4) 0.8033(5) 0.0888(17) Uani 1 1 d . . .
H17 H 0.5353 0.4029 0.8392 0.107 Uiso 1 1 calc R . .
C18 C 0.4072(4) 0.3402(4) 0.8417(4) 0.0742(15) Uani 1 1 d . . .
C19 C 0.2045(3) 0.2667(4) 0.6347(3) 0.0829(15) Uani 1 1 d . . .
H19A H 0.2029 0.2786 0.5741 0.124 Uiso 1 1 calc R . .
H19B H 0.1563 0.3139 0.6480 0.124 Uiso 1 1 calc R . .
H19C H 0.1925 0.1860 0.6437 0.124 Uiso 1 1 calc R . .
C20 C 0.5412(4) 0.4039(4) 0.6727(4) 0.130(2) Uani 1 1 d . . .
H20A H 0.5831 0.3389 0.6747 0.196 Uiso 1 1 calc R . .
H20B H 0.5769 0.4676 0.7059 0.196 Uiso 1 1 calc R . .
H20C H 0.5132 0.4275 0.6124 0.196 Uiso 1 1 calc R . .
C21 C 0.4276(3) 0.3443(4) 0.9415(4) 0.1034(17) Uani 1 1 d . . .
H21A H 0.3774 0.3863 0.9561 0.155 Uiso 1 1 calc R . .
H21B H 0.4876 0.3828 0.9674 0.155 Uiso 1 1 calc R . .
H21C H 0.4305 0.2662 0.9642 0.155 Uiso 1 1 calc R . .
C22 C 0.3122(3) 0.0009(3) 1.0560(3) 0.0544(11) Uani 1 1 d . . .
C23 C 0.4087(4) -0.0249(4) 1.0769(4) 0.0749(14) Uani 1 1 d . . .
H23 H 0.4406 -0.0115 1.0348 0.090 Uiso 1 1 calc R . .
C24 C 0.4587(4) -0.0693(4) 1.1574(4) 0.0876(16) Uani 1 1 d . . .
H24 H 0.5234 -0.0865 1.1692 0.105 Uiso 1 1 calc R . .
C25 C 0.4136(5) -0.0882(4) 1.2203(4) 0.0856(16) Uani 1 1 d . . .
H25 H 0.4480 -0.1155 1.2759 0.103 Uiso 1 1 calc R . .
C26 C 0.3183(4) -0.0672(4) 1.2018(4) 0.0781(15) Uani 1 1 d . . .
H26 H 0.2872 -0.0826 1.2442 0.094 Uiso 1 1 calc R . .
C27 C 0.2675(3) -0.0232(3) 1.1203(4) 0.0683(13) Uani 1 1 d . . .
H27 H 0.2022 -0.0094 1.1083 0.082 Uiso 1 1 calc R . .
N1 N 0.1143(2) 0.2556(3) 0.8589(2) 0.0511(9) Uani 1 1 d . . .
N2 N 0.2484(2) 0.2603(3) 0.8227(2) 0.0548(10) Uani 1 1 d . . .
O1 O 0.30277(19) 0.0866(2) 0.9046(2) 0.0639(8) Uani 1 1 d . . .
O2 O 0.1634(2) 0.0827(2) 0.94264(19) 0.0579(8) Uani 1 1 d . . .
S1 S 0.17191(8) 0.47127(9) 0.83384(8) 0.0661(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
B1 O2 1.367(5) . ?
B1 O1 1.376(5) . ?
B1 C22 1.528(6) . ?
C1 N2 1.363(4) . ?
C1 N1 1.363(4) . ?
C1 S1 1.644(4) . ?
C2 O1 1.427(4) . ?
C2 N2 1.438(4) . ?
C2 C3 1.529(5) . ?
C2 H2 0.9800 . ?
C3 O2 1.419(4) . ?
C3 N1 1.440(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.379(5) . ?
C4 C9 1.392(5) . ?
C4 N1 1.441(4) . ?
C5 C6 1.394(5) . ?
C5 C10 1.514(5) . ?
C6 C7 1.377(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(5) . ?
C7 C11 1.512(5) . ?
C8 C9 1.389(5) . ?
C8 H8 0.9300 . ?
C9 C12 1.506(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.382(6) . ?
C13 C14 1.390(5) . ?
C13 N2 1.433(5) . ?
C14 C15 1.391(5) . ?
C14 C19 1.502(5) . ?
C15 C16 1.379(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(7) . ?
C16 C20 1.528(6) . ?
C17 C18 1.390(6) . ?
C17 H17 0.9300 . ?
C18 C21 1.519(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.383(5) . ?
C22 C27 1.388(5) . ?
C23 C24 1.366(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.361(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.359(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.380(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 B1 O1 113.0(4) . . ?
O2 B1 C22 124.1(5) . . ?
O1 B1 C22 123.0(5) . . ?
N2 C1 N1 107.5(3) . . ?
N2 C1 S1 126.8(3) . . ?
N1 C1 S1 125.7(3) . . ?
O1 C2 N2 112.5(3) . . ?
O1 C2 C3 105.1(3) . . ?
N2 C2 C3 103.4(3) . . ?
O1 C2 H2 111.8 . . ?
N2 C2 H2 111.8 . . ?
C3 C2 H2 111.8 . . ?
O2 C3 N1 112.4(3) . . ?
O2 C3 C2 105.8(3) . . ?
N1 C3 C2 103.5(3) . . ?
O2 C3 H3 111.6 . . ?
N1 C3 H3 111.6 . . ?
C2 C3 H3 111.6 . . ?
C5 C4 C9 122.4(4) . . ?
C5 C4 N1 119.4(4) . . ?
C9 C4 N1 118.1(4) . . ?
C4 C5 C6 118.0(4) . . ?
C4 C5 C10 121.7(4) . . ?
C6 C5 C10 120.3(5) . . ?
C7 C6 C5 121.5(4) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 118.6(4) . . ?
C6 C7 C11 121.6(5) . . ?
C8 C7 C11 119.8(5) . . ?
C7 C8 C9 122.3(5) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C8 C9 C4 117.1(4) . . ?
C8 C9 C12 120.5(5) . . ?
C4 C9 C12 122.4(4) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.8(5) . . ?
C18 C13 N2 119.5(5) . . ?
C14 C13 N2 117.7(5) . . ?
C13 C14 C15 117.5(5) . . ?
C13 C14 C19 121.9(5) . . ?
C15 C14 C19 120.6(5) . . ?
C16 C15 C14 121.2(5) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 119.4(5) . . ?
C15 C16 C20 120.4(7) . . ?
C17 C16 C20 120.2(7) . . ?
C16 C17 C18 121.3(6) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C17 117.6(5) . . ?
C13 C18 C21 122.5(5) . . ?
C17 C18 C21 119.9(5) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 116.7(4) . . ?
C23 C22 B1 121.3(5) . . ?
C27 C22 B1 122.0(4) . . ?
C24 C23 C22 122.2(5) . . ?
C24 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
C25 C24 C23 119.8(5) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 120.1(5) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.2(5) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 121.0(4) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
C1 N1 C3 112.7(3) . . ?
C1 N1 C4 126.4(3) . . ?
C3 N1 C4 120.8(3) . . ?
C1 N2 C13 124.5(3) . . ?
C1 N2 C2 112.9(3) . . ?
C13 N2 C2 121.8(3) . . ?
B1 O1 C2 108.0(3) . . ?
B1 O2 C3 108.1(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
O1 C2 C3 O2 0.3(4) . . . . ?
N2 C2 C3 O2 -117.8(3) . . . . ?
O1 C2 C3 N1 118.6(3) . . . . ?
N2 C2 C3 N1 0.5(4) . . . . ?
C9 C4 C5 C6 0.7(6) . . . . ?
N1 C4 C5 C6 -176.3(3) . . . . ?
C9 C4 C5 C10 -179.3(3) . . . . ?
N1 C4 C5 C10 3.7(5) . . . . ?
C4 C5 C6 C7 0.7(6) . . . . ?
C10 C5 C6 C7 -179.3(4) . . . . ?
C5 C6 C7 C8 -1.5(6) . . . . ?
C5 C6 C7 C11 179.8(4) . . . . ?
C6 C7 C8 C9 1.0(6) . . . . ?
C11 C7 C8 C9 179.7(4) . . . . ?
C7 C8 C9 C4 0.3(6) . . . . ?
C7 C8 C9 C12 -178.4(4) . . . . ?
C5 C4 C9 C8 -1.2(6) . . . . ?
N1 C4 C9 C8 175.8(3) . . . . ?
C5 C4 C9 C12 177.4(4) . . . . ?
N1 C4 C9 C12 -5.5(5) . . . . ?
C18 C13 C14 C15 3.6(6) . . . . ?
N2 C13 C14 C15 -175.1(3) . . . . ?
C18 C13 C14 C19 -175.6(4) . . . . ?
N2 C13 C14 C19 5.7(6) . . . . ?
C13 C14 C15 C16 -2.1(6) . . . . ?
C19 C14 C15 C16 177.2(4) . . . . ?
C14 C15 C16 C17 -1.3(7) . . . . ?
C14 C15 C16 C20 -179.6(4) . . . . ?
C15 C16 C17 C18 3.3(7) . . . . ?
C20 C16 C17 C18 -178.4(4) . . . . ?
C14 C13 C18 C17 -1.7(6) . . . . ?
N2 C13 C18 C17 177.0(3) . . . . ?
C14 C13 C18 C21 178.8(4) . . . . ?
N2 C13 C18 C21 -2.6(6) . . . . ?
C16 C17 C18 C13 -1.9(6) . . . . ?
C16 C17 C18 C21 177.7(4) . . . . ?
O2 B1 C22 C23 179.4(4) . . . . ?
O1 B1 C22 C23 -2.0(6) . . . . ?
O2 B1 C22 C27 -2.2(6) . . . . ?
O1 B1 C22 C27 176.3(4) . . . . ?
C27 C22 C23 C24 -1.5(6) . . . . ?
B1 C22 C23 C24 176.9(4) . . . . ?
C22 C23 C24 C25 -0.7(7) . . . . ?
C23 C24 C25 C26 2.6(7) . . . . ?
C24 C25 C26 C27 -2.1(7) . . . . ?
C25 C26 C27 C22 -0.2(7) . . . . ?
C23 C22 C27 C26 1.9(6) . . . . ?
B1 C22 C27 C26 -176.5(4) . . . . ?
N2 C1 N1 C3 0.5(5) . . . . ?
S1 C1 N1 C3 179.5(3) . . . . ?
N2 C1 N1 C4 -176.0(4) . . . . ?
S1 C1 N1 C4 3.1(6) . . . . ?
O2 C3 N1 C1 113.1(4) . . . . ?
C2 C3 N1 C1 -0.6(5) . . . . ?
O2 C3 N1 C4 -70.2(5) . . . . ?
C2 C3 N1 C4 176.0(4) . . . . ?
C5 C4 N1 C1 -85.0(5) . . . . ?
C9 C4 N1 C1 97.9(5) . . . . ?
C5 C4 N1 C3 98.8(4) . . . . ?
C9 C4 N1 C3 -78.3(5) . . . . ?
N1 C1 N2 C13 169.6(4) . . . . ?
S1 C1 N2 C13 -9.4(6) . . . . ?
N1 C1 N2 C2 -0.1(5) . . . . ?
S1 C1 N2 C2 -179.1(3) . . . . ?
C18 C13 N2 C1 91.1(5) . . . . ?
C14 C13 N2 C1 -90.2(5) . . . . ?
C18 C13 N2 C2 -100.1(5) . . . . ?
C14 C13 N2 C2 78.6(5) . . . . ?
O1 C2 N2 C1 -113.1(4) . . . . ?
C3 C2 N2 C1 -0.3(5) . . . . ?
O1 C2 N2 C13 76.9(5) . . . . ?
C3 C2 N2 C13 -170.3(4) . . . . ?
O2 B1 O1 C2 0.0(4) . . . . ?
C22 B1 O1 C2 -178.7(4) . . . . ?
N2 C2 O1 B1 111.6(4) . . . . ?
C3 C2 O1 B1 -0.2(4) . . . . ?
O1 B1 O2 C3 0.2(4) . . . . ?
C22 B1 O2 C3 178.9(4) . . . . ?
N1 C3 O2 B1 -112.6(4) . . . . ?
C2 C3 O2 B1 -0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_22janb_0m
_database_code_depnum_ccdc_archive 'CCDC 1063841'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H29 B N2 O2 Se'
_chemical_formula_sum            'C27 H29 B N2 O2 Se'
_chemical_formula_weight         503.29

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_HALL  '-P 2yn'
loop_
_symmetry_equiv_pos_as_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                   14.5257(8)
_cell_length_b                   11.2585(6)
_cell_length_c                   15.9893(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.794(2)
_cell_angle_gamma                90.00
_cell_volume                     2503.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6504
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.44

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    1.526
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7923
_exptl_absorpt_correction_T_max  0.8381
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22532
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0656
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         27.00
_reflns_number_total             5472
_reflns_number_gt                4039
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0685P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5472
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.7520(3) 0.9471(3) 0.0374(3) 0.0173(8) Uani 1 1 d . . .
C1 C 0.8310(2) 0.6708(3) 0.16377(19) 0.0151(7) Uani 1 1 d . . .
C2 C 0.7793(2) 0.8658(3) 0.1721(2) 0.0172(7) Uani 1 1 d . . .
H2 H 0.7859 0.9093 0.2265 0.021 Uiso 1 1 calc R . .
C3 C 0.8735(2) 0.8667(3) 0.1454(2) 0.0170(7) Uani 1 1 d . . .
H3 H 0.9250 0.9103 0.1873 0.020 Uiso 1 1 calc R . .
C4 C 0.9840(2) 0.7061(3) 0.1256(2) 0.0155(7) Uani 1 1 d . . .
C5 C 1.0688(2) 0.7137(3) 0.1933(2) 0.0173(7) Uani 1 1 d . . .
C6 C 1.1543(2) 0.6873(3) 0.1747(2) 0.0195(7) Uani 1 1 d . . .
H6 H 1.2119 0.6920 0.2193 0.023 Uiso 1 1 calc R . .
C7 C 1.1564(2) 0.6542(3) 0.0915(2) 0.0185(7) Uani 1 1 d . . .
C8 C 1.0697(2) 0.6455(3) 0.0262(2) 0.0191(7) Uani 1 1 d . . .
H8 H 1.0702 0.6214 -0.0292 0.023 Uiso 1 1 calc R . .
C9 C 0.9816(2) 0.6718(3) 0.0409(2) 0.0165(7) Uani 1 1 d . . .
C10 C 1.0701(2) 0.7456(3) 0.2852(2) 0.0252(8) Uani 1 1 d . . .
H10A H 1.0565 0.8287 0.2881 0.038 Uiso 1 1 calc R . .
H10B H 1.1324 0.7284 0.3245 0.038 Uiso 1 1 calc R . .
H10C H 1.0222 0.7000 0.3017 0.038 Uiso 1 1 calc R . .
C11 C 1.2508(2) 0.6277(3) 0.0749(2) 0.0291(9) Uani 1 1 d . . .
H11A H 1.2907 0.6972 0.0868 0.044 Uiso 1 1 calc R . .
H11B H 1.2399 0.6048 0.0150 0.044 Uiso 1 1 calc R . .
H11C H 1.2823 0.5641 0.1123 0.044 Uiso 1 1 calc R . .
C12 C 0.8891(2) 0.6624(3) -0.0304(2) 0.0214(7) Uani 1 1 d . . .
H12A H 0.8448 0.6141 -0.0111 0.032 Uiso 1 1 calc R . .
H12B H 0.9008 0.6269 -0.0810 0.032 Uiso 1 1 calc R . .
H12C H 0.8623 0.7403 -0.0450 0.032 Uiso 1 1 calc R . .
C13 C 0.6885(2) 0.6996(3) 0.2177(2) 0.0181(7) Uani 1 1 d . . .
C14 C 0.6003(2) 0.6640(3) 0.1627(2) 0.0228(8) Uani 1 1 d . . .
C15 C 0.5291(2) 0.6325(3) 0.2006(3) 0.0294(9) Uani 1 1 d . . .
H15 H 0.4700 0.6062 0.1651 0.035 Uiso 1 1 calc R . .
C16 C 0.5440(3) 0.6394(3) 0.2903(3) 0.0292(9) Uani 1 1 d . . .
C17 C 0.6336(3) 0.6737(3) 0.3437(2) 0.0264(8) Uani 1 1 d . . .
H17 H 0.6440 0.6774 0.4038 0.032 Uiso 1 1 calc R . .
C18 C 0.7082(2) 0.7026(3) 0.3087(2) 0.0200(7) Uani 1 1 d . . .
C19 C 0.5812(2) 0.6588(3) 0.0649(2) 0.0332(9) Uani 1 1 d . . .
H19A H 0.5170 0.6306 0.0385 0.050 Uiso 1 1 calc R . .
H19B H 0.6263 0.6057 0.0508 0.050 Uiso 1 1 calc R . .
H19C H 0.5881 0.7367 0.0431 0.050 Uiso 1 1 calc R . .
C20 C 0.4637(3) 0.6095(3) 0.3293(3) 0.0431(11) Uani 1 1 d . . .
H20A H 0.4894 0.6006 0.3914 0.065 Uiso 1 1 calc R . .
H20B H 0.4336 0.5367 0.3044 0.065 Uiso 1 1 calc R . .
H20C H 0.4170 0.6723 0.3167 0.065 Uiso 1 1 calc R . .
C21 C 0.8071(2) 0.7311(3) 0.3672(2) 0.0254(8) Uani 1 1 d . . .
H21A H 0.8535 0.6807 0.3526 0.038 Uiso 1 1 calc R . .
H21B H 0.8089 0.7182 0.4270 0.038 Uiso 1 1 calc R . .
H21C H 0.8221 0.8127 0.3594 0.038 Uiso 1 1 calc R . .
C22 C 0.6972(2) 1.0026(3) -0.0508(2) 0.0175(7) Uani 1 1 d . . .
C23 C 0.7409(2) 1.0232(3) -0.1164(2) 0.0206(7) Uani 1 1 d . . .
H23 H 0.8063 1.0085 -0.1057 0.025 Uiso 1 1 calc R . .
C24 C 0.6878(3) 1.0654(3) -0.1975(2) 0.0237(8) Uani 1 1 d . . .
H24 H 0.7178 1.0780 -0.2409 0.028 Uiso 1 1 calc R . .
C25 C 0.5914(3) 1.0887(3) -0.2141(2) 0.0257(8) Uani 1 1 d . . .
H25 H 0.5560 1.1162 -0.2688 0.031 Uiso 1 1 calc R . .
C26 C 0.5468(2) 1.0712(3) -0.1491(2) 0.0267(8) Uani 1 1 d . . .
H26 H 0.4817 1.0880 -0.1598 0.032 Uiso 1 1 calc R . .
C27 C 0.5991(2) 1.0290(3) -0.0692(2) 0.0218(8) Uani 1 1 d . . .
H27 H 0.5687 1.0175 -0.0260 0.026 Uiso 1 1 calc R . .
N1 N 0.89582(18) 0.7420(2) 0.14232(16) 0.0145(6) Uani 1 1 d . . .
N2 N 0.76258(18) 0.7400(2) 0.18117(17) 0.0157(6) Uani 1 1 d . . .
O1 O 0.70881(15) 0.91742(19) 0.10033(14) 0.0181(5) Uani 1 1 d . . .
O2 O 0.84837(15) 0.91954(18) 0.06071(14) 0.0170(5) Uani 1 1 d . . .
Se1 Se 0.83559(2) 0.51011(3) 0.16883(2) 0.01740(12) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 O1 1.373(4) . ?
B1 O2 1.376(4) . ?
B1 C22 1.536(5) . ?
C1 N2 1.353(4) . ?
C1 N1 1.354(4) . ?
C1 Se1 1.812(3) . ?
C2 O1 1.423(4) . ?
C2 N2 1.451(4) . ?
C2 C3 1.546(4) . ?
C2 H2 0.9800 . ?
C3 O2 1.426(4) . ?
C3 N1 1.444(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.387(4) . ?
C4 C9 1.398(4) . ?
C4 N1 1.441(4) . ?
C5 C6 1.391(4) . ?
C5 C10 1.508(4) . ?
C6 C7 1.391(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(5) . ?
C7 C11 1.500(4) . ?
C8 C9 1.397(4) . ?
C8 H8 0.9300 . ?
C9 C12 1.494(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.388(5) . ?
C13 C18 1.399(4) . ?
C13 N2 1.439(4) . ?
C14 C15 1.387(4) . ?
C14 C19 1.508(5) . ?
C15 C16 1.389(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(5) . ?
C16 C20 1.511(4) . ?
C17 C18 1.394(4) . ?
C17 H17 0.9300 . ?
C18 C21 1.506(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.394(4) . ?
C22 C27 1.401(4) . ?
C23 C24 1.387(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.374(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.389(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.369(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 B1 O2 113.0(3) . . ?
O1 B1 C22 123.1(3) . . ?
O2 B1 C22 123.9(3) . . ?
N2 C1 N1 108.5(3) . . ?
N2 C1 Se1 125.8(2) . . ?
N1 C1 Se1 125.7(2) . . ?
O1 C2 N2 112.2(3) . . ?
O1 C2 C3 105.3(2) . . ?
N2 C2 C3 102.8(2) . . ?
O1 C2 H2 112.0 . . ?
N2 C2 H2 112.0 . . ?
C3 C2 H2 112.0 . . ?
O2 C3 N1 111.8(2) . . ?
O2 C3 C2 105.1(2) . . ?
N1 C3 C2 103.2(2) . . ?
O2 C3 H3 112.1 . . ?
N1 C3 H3 112.1 . . ?
C2 C3 H3 112.1 . . ?
C5 C4 C9 122.8(3) . . ?
C5 C4 N1 118.3(3) . . ?
C9 C4 N1 118.8(3) . . ?
C4 C5 C6 117.8(3) . . ?
C4 C5 C10 122.3(3) . . ?
C6 C5 C10 119.9(3) . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C8 C7 C6 118.1(3) . . ?
C8 C7 C11 122.1(3) . . ?
C6 C7 C11 119.8(3) . . ?
C7 C8 C9 122.4(3) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C8 C9 C4 116.9(3) . . ?
C8 C9 C12 121.5(3) . . ?
C4 C9 C12 121.6(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 122.7(3) . . ?
C14 C13 N2 119.7(3) . . ?
C18 C13 N2 117.5(3) . . ?
C15 C14 C13 117.7(3) . . ?
C15 C14 C19 120.4(3) . . ?
C13 C14 C19 121.9(3) . . ?
C14 C15 C16 121.6(3) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 C20 120.4(4) . . ?
C15 C16 C20 120.3(4) . . ?
C16 C17 C18 121.2(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C13 117.5(3) . . ?
C17 C18 C21 120.9(3) . . ?
C13 C18 C21 121.6(3) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 117.6(3) . . ?
C23 C22 B1 122.0(3) . . ?
C27 C22 B1 120.3(3) . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C22 121.8(3) . . ?
C26 C27 H27 119.1 . . ?
C22 C27 H27 119.1 . . ?
C1 N1 C4 127.0(3) . . ?
C1 N1 C3 112.8(2) . . ?
C4 N1 C3 119.9(2) . . ?
C1 N2 C13 125.6(3) . . ?
C1 N2 C2 112.7(2) . . ?
C13 N2 C2 121.1(2) . . ?
B1 O1 C2 108.4(2) . . ?
B1 O2 C3 108.3(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
O1 C2 C3 O2 0.3(3) . . . . ?
N2 C2 C3 O2 117.9(2) . . . . ?
O1 C2 C3 N1 -117.0(2) . . . . ?
N2 C2 C3 N1 0.6(3) . . . . ?
C9 C4 C5 C6 0.9(4) . . . . ?
N1 C4 C5 C6 -175.3(3) . . . . ?
C9 C4 C5 C10 -177.2(3) . . . . ?
N1 C4 C5 C10 6.5(4) . . . . ?
C4 C5 C6 C7 -0.1(5) . . . . ?
C10 C5 C6 C7 178.1(3) . . . . ?
C5 C6 C7 C8 -1.2(5) . . . . ?
C5 C6 C7 C11 179.5(3) . . . . ?
C6 C7 C8 C9 1.7(5) . . . . ?
C11 C7 C8 C9 -179.0(3) . . . . ?
C7 C8 C9 C4 -0.9(4) . . . . ?
C7 C8 C9 C12 179.7(3) . . . . ?
C5 C4 C9 C8 -0.5(4) . . . . ?
N1 C4 C9 C8 175.7(3) . . . . ?
C5 C4 C9 C12 179.0(3) . . . . ?
N1 C4 C9 C12 -4.8(4) . . . . ?
C18 C13 C14 C15 1.2(5) . . . . ?
N2 C13 C14 C15 -176.2(3) . . . . ?
C18 C13 C14 C19 -178.6(3) . . . . ?
N2 C13 C14 C19 3.9(5) . . . . ?
C13 C14 C15 C16 1.8(5) . . . . ?
C19 C14 C15 C16 -178.3(3) . . . . ?
C14 C15 C16 C17 -2.8(5) . . . . ?
C14 C15 C16 C20 177.3(3) . . . . ?
C15 C16 C17 C18 0.8(5) . . . . ?
C20 C16 C17 C18 -179.4(3) . . . . ?
C16 C17 C18 C13 2.1(4) . . . . ?
C16 C17 C18 C21 -175.5(3) . . . . ?
C14 C13 C18 C17 -3.1(5) . . . . ?
N2 C13 C18 C17 174.4(3) . . . . ?
C14 C13 C18 C21 174.4(3) . . . . ?
N2 C13 C18 C21 -8.0(4) . . . . ?
O1 B1 C22 C23 -174.7(3) . . . . ?
O2 B1 C22 C23 3.7(5) . . . . ?
O1 B1 C22 C27 2.2(5) . . . . ?
O2 B1 C22 C27 -179.4(3) . . . . ?
C27 C22 C23 C24 -1.6(4) . . . . ?
B1 C22 C23 C24 175.4(3) . . . . ?
C22 C23 C24 C25 0.6(5) . . . . ?
C23 C24 C25 C26 0.7(5) . . . . ?
C24 C25 C26 C27 -1.0(5) . . . . ?
C25 C26 C27 C22 -0.1(5) . . . . ?
C23 C22 C27 C26 1.3(5) . . . . ?
B1 C22 C27 C26 -175.7(3) . . . . ?
N2 C1 N1 C4 174.9(3) . . . . ?
Se1 C1 N1 C4 -4.8(4) . . . . ?
N2 C1 N1 C3 0.6(3) . . . . ?
Se1 C1 N1 C3 -179.1(2) . . . . ?
C5 C4 N1 C1 -96.4(4) . . . . ?
C9 C4 N1 C1 87.2(4) . . . . ?
C5 C4 N1 C3 77.5(4) . . . . ?
C9 C4 N1 C3 -98.9(3) . . . . ?
O2 C3 N1 C1 -113.2(3) . . . . ?
C2 C3 N1 C1 -0.8(3) . . . . ?
O2 C3 N1 C4 72.1(3) . . . . ?
C2 C3 N1 C4 -175.5(3) . . . . ?
N1 C1 N2 C13 -171.0(3) . . . . ?
Se1 C1 N2 C13 8.7(4) . . . . ?
N1 C1 N2 C2 -0.2(3) . . . . ?
Se1 C1 N2 C2 179.5(2) . . . . ?
C14 C13 N2 C1 -91.1(4) . . . . ?
C18 C13 N2 C1 91.3(4) . . . . ?
C14 C13 N2 C2 98.8(4) . . . . ?
C18 C13 N2 C2 -78.8(4) . . . . ?
O1 C2 N2 C1 112.3(3) . . . . ?
C3 C2 N2 C1 -0.3(3) . . . . ?
O1 C2 N2 C13 -76.4(3) . . . . ?
C3 C2 N2 C13 171.0(3) . . . . ?
O2 B1 O1 C2 -0.1(4) . . . . ?
C22 B1 O1 C2 178.5(3) . . . . ?
N2 C2 O1 B1 -111.2(3) . . . . ?
C3 C2 O1 B1 -0.2(3) . . . . ?
O1 B1 O2 C3 0.3(3) . . . . ?
C22 B1 O2 C3 -178.3(3) . . . . ?
N1 C3 O2 B1 110.9(3) . . . . ?
C2 C3 O2 B1 -0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.196
####################################################################### 
# 
# 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_9aprb_0m
_database_code_depnum_ccdc_archive 'CCDC 1063842'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C88 H108 B4 F8 N8 O8 S4'
_chemical_formula_sum            'C88 H108 B4 F8 N8 O8 S4'
_chemical_formula_weight         1729.30

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_HALL  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.9074(6)
_cell_length_b                   12.1853(6)
_cell_length_c                   17.8010(9)
_cell_angle_alpha                93.320(2)
_cell_angle_beta                 103.831(2)
_cell_angle_gamma                103.498(2)
_cell_volume                     2420.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5854
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      21.35

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30629
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_sigmaI/netI    0.1271
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.50
_reflns_number_total             9017
_reflns_number_gt                4638
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1058P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9017
_refine_ls_number_parameters     555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1478
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.1993
_refine_ls_wR_factor_gt          0.1772
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.1928(4) 1.0936(4) -0.0254(3) 0.0377(12) Uani 1 1 d . . .
B2 B 0.7741(4) -0.0737(4) 0.4449(3) 0.0358(12) Uani 1 1 d . . .
C1 C 0.2781(3) 0.9567(3) 0.1526(2) 0.0278(9) Uani 1 1 d . . .
C2 C 0.1440(3) 1.0552(3) 0.0917(2) 0.0296(9) Uani 1 1 d . . .
H2 H 0.0716 1.0579 0.1081 0.035 Uiso 1 1 calc R . .
C3 C 0.1267(3) 0.9434(3) 0.0409(2) 0.0293(9) Uani 1 1 d . . .
H3 H 0.0455 0.8950 0.0326 0.035 Uiso 1 1 calc R . .
C4 C 0.2310(4) 0.7813(3) 0.0645(2) 0.0313(10) Uani 1 1 d . . .
C5 C 0.1521(4) 0.6862(4) 0.0795(2) 0.0440(12) Uani 1 1 d . . .
C6 C 0.1676(5) 0.5815(4) 0.0573(3) 0.0673(16) Uani 1 1 d . . .
H6 H 0.1154 0.5165 0.0657 0.081 Uiso 1 1 calc R . .
C7 C 0.2558(7) 0.5691(5) 0.0236(3) 0.0761(18) Uani 1 1 d . . .
C8 C 0.3292(5) 0.6656(5) 0.0080(3) 0.0669(15) Uani 1 1 d . . .
H8 H 0.3880 0.6579 -0.0167 0.080 Uiso 1 1 calc R . .
C9 C 0.3187(4) 0.7727(4) 0.0274(3) 0.0420(11) Uani 1 1 d . . .
C10 C 0.0576(4) 0.6954(4) 0.1198(3) 0.0686(16) Uani 1 1 d . . .
H10A H 0.0146 0.6207 0.1257 0.103 Uiso 1 1 calc R . .
H10B H 0.0033 0.7331 0.0894 0.103 Uiso 1 1 calc R . .
H10C H 0.0942 0.7383 0.1703 0.103 Uiso 1 1 calc R . .
C11 C 0.2768(7) 0.4511(5) 0.0055(4) 0.124(3) Uani 1 1 d . . .
H11A H 0.2754 0.4099 0.0498 0.185 Uiso 1 1 calc R . .
H11B H 0.3531 0.4604 -0.0058 0.185 Uiso 1 1 calc R . .
H11C H 0.2148 0.4095 -0.0387 0.185 Uiso 1 1 calc R . .
C12 C 0.4010(4) 0.8770(4) 0.0112(3) 0.0558(13) Uani 1 1 d . . .
H12A H 0.3553 0.9168 -0.0241 0.084 Uiso 1 1 calc R . .
H12B H 0.4590 0.8552 -0.0116 0.084 Uiso 1 1 calc R . .
H12C H 0.4411 0.9258 0.0591 0.084 Uiso 1 1 calc R . .
C13 C 0.2876(3) 1.1402(3) 0.2248(2) 0.0251(9) Uani 1 1 d . . .
C14 C 0.3836(3) 1.2321(3) 0.2256(2) 0.0318(10) Uani 1 1 d . . .
C15 C 0.4227(4) 1.3139(3) 0.2914(2) 0.0360(10) Uani 1 1 d . . .
H15 H 0.4837 1.3780 0.2926 0.043 Uiso 1 1 calc R . .
C16 C 0.3742(4) 1.3029(3) 0.3541(2) 0.0343(10) Uani 1 1 d . . .
C17 C 0.2813(4) 1.2101(4) 0.3504(2) 0.0356(10) Uani 1 1 d . . .
H17 H 0.2483 1.2017 0.3928 0.043 Uiso 1 1 calc R . .
C18 C 0.2346(3) 1.1286(3) 0.2865(2) 0.0291(9) Uani 1 1 d . . .
C19 C 0.4432(4) 1.2433(4) 0.1595(2) 0.0445(12) Uani 1 1 d . . .
H19A H 0.4796 1.1815 0.1554 0.067 Uiso 1 1 calc R . .
H19B H 0.5034 1.3140 0.1693 0.067 Uiso 1 1 calc R . .
H19C H 0.3844 1.2415 0.1116 0.067 Uiso 1 1 calc R . .
C20 C 0.4229(4) 1.3898(4) 0.4247(3) 0.0532(13) Uani 1 1 d . . .
H20A H 0.5087 1.4065 0.4393 0.080 Uiso 1 1 calc R . .
H20B H 0.3927 1.3606 0.4669 0.080 Uiso 1 1 calc R . .
H20C H 0.3986 1.4581 0.4131 0.080 Uiso 1 1 calc R . .
C21 C 0.1314(4) 1.0280(4) 0.2852(2) 0.0420(11) Uani 1 1 d . . .
H21A H 0.1573 0.9593 0.2832 0.063 Uiso 1 1 calc R . .
H21B H 0.0670 1.0246 0.2401 0.063 Uiso 1 1 calc R . .
H21C H 0.1045 1.0365 0.3314 0.063 Uiso 1 1 calc R . .
C22 C 0.4377(4) 0.9926(4) 0.3072(2) 0.0443(11) Uani 1 1 d . . .
H22A H 0.4606 1.0711 0.2991 0.066 Uiso 1 1 calc R . .
H22B H 0.5055 0.9718 0.3384 0.066 Uiso 1 1 calc R . .
H22C H 0.3751 0.9817 0.3336 0.066 Uiso 1 1 calc R . .
C23 C 0.8237(3) 0.2402(3) 0.4397(2) 0.0311(10) Uani 1 1 d . . .
C24 C 0.9182(4) 0.0938(3) 0.4453(2) 0.0331(10) Uani 1 1 d . . .
H24 H 1.0058 0.1130 0.4587 0.040 Uiso 1 1 calc R . .
C25 C 0.8725(4) 0.1044(3) 0.5175(2) 0.0365(10) Uani 1 1 d . . .
H25 H 0.9375 0.1169 0.5653 0.044 Uiso 1 1 calc R . .
C26 C 0.7746(4) 0.2521(3) 0.5665(2) 0.0344(10) Uani 1 1 d . . .
C27 C 0.6511(4) 0.2261(3) 0.5582(2) 0.0363(10) Uani 1 1 d . . .
C28 C 0.6121(4) 0.2780(3) 0.6151(2) 0.0395(11) Uani 1 1 d . . .
H28 H 0.5303 0.2640 0.6102 0.047 Uiso 1 1 calc R . .
C29 C 0.6888(4) 0.3486(3) 0.6780(2) 0.0432(11) Uani 1 1 d . . .
C30 C 0.8095(4) 0.3722(3) 0.6840(3) 0.0446(12) Uani 1 1 d . . .
H30 H 0.8619 0.4212 0.7265 0.054 Uiso 1 1 calc R . .
C31 C 0.8557(4) 0.3257(3) 0.6291(3) 0.0393(11) Uani 1 1 d . . .
C32 C 0.5644(4) 0.1505(4) 0.4895(3) 0.0439(11) Uani 1 1 d . . .
H32A H 0.4860 0.1323 0.4984 0.066 Uiso 1 1 calc R . .
H32B H 0.5887 0.0818 0.4821 0.066 Uiso 1 1 calc R . .
H32C H 0.5626 0.1889 0.4438 0.066 Uiso 1 1 calc R . .
C33 C 0.6421(5) 0.4020(4) 0.7386(3) 0.0626(15) Uani 1 1 d . . .
H33A H 0.5583 0.3957 0.7182 0.094 Uiso 1 1 calc R . .
H33B H 0.6843 0.4807 0.7519 0.094 Uiso 1 1 calc R . .
H33C H 0.6540 0.3635 0.7843 0.094 Uiso 1 1 calc R . .
C34 C 0.9877(4) 0.3583(4) 0.6336(3) 0.0628(15) Uani 1 1 d . . .
H34A H 1.0298 0.4092 0.6802 0.094 Uiso 1 1 calc R . .
H34B H 1.0002 0.3953 0.5890 0.094 Uiso 1 1 calc R . .
H34C H 1.0170 0.2913 0.6343 0.094 Uiso 1 1 calc R . .
C35 C 0.9105(3) 0.2100(3) 0.3308(2) 0.0301(9) Uani 1 1 d . . .
C36 C 1.0162(3) 0.2946(3) 0.3419(2) 0.0317(10) Uani 1 1 d . . .
C37 C 1.0533(4) 0.3232(3) 0.2748(3) 0.0365(10) Uani 1 1 d . . .
H37 H 1.1235 0.3796 0.2804 0.044 Uiso 1 1 calc R . .
C38 C 0.9898(4) 0.2711(3) 0.2008(2) 0.0369(10) Uani 1 1 d . . .
C39 C 0.8851(4) 0.1865(3) 0.1938(3) 0.0458(12) Uani 1 1 d . . .
H39 H 0.8418 0.1501 0.1445 0.055 Uiso 1 1 calc R . .
C40 C 0.8432(4) 0.1549(3) 0.2570(3) 0.0400(11) Uani 1 1 d . . .
C41 C 1.0854(3) 0.3574(3) 0.4209(2) 0.0353(10) Uani 1 1 d . . .
H41A H 1.1546 0.4124 0.4159 0.053 Uiso 1 1 calc R . .
H41B H 1.1100 0.3044 0.4550 0.053 Uiso 1 1 calc R . .
H41C H 1.0356 0.3953 0.4420 0.053 Uiso 1 1 calc R . .
C42 C 1.0315(5) 0.3080(4) 0.1312(3) 0.0532(13) Uani 1 1 d . . .
H42A H 0.9783 0.3479 0.1021 0.080 Uiso 1 1 calc R . .
H42B H 1.0321 0.2425 0.0988 0.080 Uiso 1 1 calc R . .
H42C H 1.1108 0.3574 0.1480 0.080 Uiso 1 1 calc R . .
C43 C 0.7266(4) 0.0656(4) 0.2454(3) 0.0598(14) Uani 1 1 d . . .
H43A H 0.6676 0.1004 0.2577 0.090 Uiso 1 1 calc R . .
H43B H 0.7386 0.0082 0.2790 0.090 Uiso 1 1 calc R . .
H43C H 0.6995 0.0315 0.1921 0.090 Uiso 1 1 calc R . .
C44 C 0.7518(4) 0.3680(4) 0.3192(2) 0.0498(12) Uani 1 1 d . . .
H44A H 0.8265 0.3719 0.3065 0.075 Uiso 1 1 calc R . .
H44B H 0.7255 0.4348 0.3057 0.075 Uiso 1 1 calc R . .
H44C H 0.6931 0.3017 0.2904 0.075 Uiso 1 1 calc R . .
F1 F 0.31329(19) 1.1259(2) -0.02551(14) 0.0477(7) Uani 1 1 d . . .
F2 F 0.1277(2) 1.1336(2) -0.08930(13) 0.0479(7) Uani 1 1 d . . .
F3 F 0.6625(2) -0.0937(2) 0.39346(14) 0.0520(7) Uani 1 1 d . . .
F4 F 0.7919(2) -0.17778(18) 0.46633(14) 0.0455(6) Uani 1 1 d . . .
N1 N 0.2165(3) 0.8906(3) 0.08743(18) 0.0277(8) Uani 1 1 d . . .
N2 N 0.2452(2) 1.0534(3) 0.15972(16) 0.0242(7) Uani 1 1 d . . .
N3 N 0.8215(3) 0.2032(3) 0.50847(19) 0.0317(8) Uani 1 1 d . . .
N4 N 0.8700(3) 0.1790(2) 0.39787(19) 0.0307(8) Uani 1 1 d . . .
O1 O 0.1737(2) 1.1411(2) 0.04766(14) 0.0316(7) Uani 1 1 d . . .
O2 O 0.1497(2) 0.9709(2) -0.02863(15) 0.0367(7) Uani 1 1 d . . .
O3 O 0.8696(2) -0.0168(2) 0.41078(16) 0.0387(7) Uani 1 1 d . . .
O4 O 0.7852(3) 0.0039(2) 0.51436(17) 0.0440(8) Uani 1 1 d . . .
S1 S 0.38530(10) 0.90588(9) 0.21532(6) 0.0400(3) Uani 1 1 d . . .
S2 S 0.77104(10) 0.36020(9) 0.42099(7) 0.0436(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F2 1.397(5) . ?
B1 F1 1.397(5) . ?
B1 O2 1.456(6) . ?
B1 O1 1.481(5) . ?
B2 F3 1.380(5) . ?
B2 F4 1.394(5) . ?
B2 O3 1.469(5) . ?
B2 O4 1.472(6) . ?
C1 N1 1.320(5) . ?
C1 N2 1.335(5) . ?
C1 S1 1.740(4) . ?
C2 O1 1.375(4) . ?
C2 N2 1.495(5) . ?
C2 C3 1.534(5) . ?
C2 H2 0.9800 . ?
C3 O2 1.374(4) . ?
C3 N1 1.484(4) . ?
C3 H3 0.9800 . ?
C4 C9 1.383(5) . ?
C4 C5 1.394(6) . ?
C4 N1 1.430(5) . ?
C5 C6 1.380(7) . ?
C5 C10 1.494(6) . ?
C6 C7 1.359(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(8) . ?
C7 C11 1.545(7) . ?
C8 C9 1.372(6) . ?
C8 H8 0.9300 . ?
C9 C12 1.501(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.390(5) . ?
C13 C14 1.398(5) . ?
C13 N2 1.430(4) . ?
C14 C15 1.404(5) . ?
C14 C19 1.510(5) . ?
C15 C16 1.374(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(5) . ?
C16 C20 1.499(6) . ?
C17 C18 1.377(5) . ?
C17 H17 0.9300 . ?
C18 C21 1.514(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 S1 1.785(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N4 1.318(5) . ?
C23 N3 1.332(5) . ?
C23 S2 1.740(4) . ?
C24 O3 1.378(4) . ?
C24 N4 1.506(4) . ?
C24 C25 1.520(6) . ?
C24 H24 0.9800 . ?
C25 O4 1.398(4) . ?
C25 N3 1.470(5) . ?
C25 H25 0.9800 . ?
C26 C31 1.394(6) . ?
C26 C27 1.400(6) . ?
C26 N3 1.447(5) . ?
C27 C28 1.389(6) . ?
C27 C32 1.495(6) . ?
C28 C29 1.363(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.375(6) . ?
C29 C33 1.507(6) . ?
C30 C31 1.385(6) . ?
C30 H30 0.9300 . ?
C31 C34 1.510(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.392(5) . ?
C35 C40 1.401(6) . ?
C35 N4 1.429(5) . ?
C36 C37 1.405(5) . ?
C36 C41 1.505(5) . ?
C37 C38 1.383(6) . ?
C37 H37 0.9300 . ?
C38 C39 1.395(6) . ?
C38 C42 1.496(6) . ?
C39 C40 1.375(6) . ?
C39 H39 0.9300 . ?
C40 C43 1.512(6) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 S2 1.783(4) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?

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
F2 B1 F1 107.7(4) . . ?
F2 B1 O2 110.9(4) . . ?
F1 B1 O2 111.8(4) . . ?
F2 B1 O1 110.1(4) . . ?
F1 B1 O1 111.2(4) . . ?
O2 B1 O1 105.1(3) . . ?
F3 B2 F4 108.1(3) . . ?
F3 B2 O3 112.1(4) . . ?
F4 B2 O3 110.0(3) . . ?
F3 B2 O4 111.6(4) . . ?
F4 B2 O4 110.3(4) . . ?
O3 B2 O4 104.8(3) . . ?
N1 C1 N2 112.8(3) . . ?
N1 C1 S1 116.9(3) . . ?
N2 C1 S1 130.3(3) . . ?
O1 C2 N2 112.5(3) . . ?
O1 C2 C3 106.4(3) . . ?
N2 C2 C3 103.0(3) . . ?
O1 C2 H2 111.5 . . ?
N2 C2 H2 111.5 . . ?
C3 C2 H2 111.5 . . ?
O2 C3 N1 112.8(3) . . ?
O2 C3 C2 107.4(3) . . ?
N1 C3 C2 103.2(3) . . ?
O2 C3 H3 111.0 . . ?
N1 C3 H3 111.0 . . ?
C2 C3 H3 111.0 . . ?
C9 C4 C5 122.4(4) . . ?
C9 C4 N1 120.2(3) . . ?
C5 C4 N1 117.4(4) . . ?
C6 C5 C4 116.7(5) . . ?
C6 C5 C10 120.8(4) . . ?
C4 C5 C10 122.4(4) . . ?
C7 C6 C5 122.9(5) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C8 118.2(5) . . ?
C6 C7 C11 121.5(6) . . ?
C8 C7 C11 120.3(6) . . ?
C9 C8 C7 122.4(5) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C8 C9 C4 117.4(4) . . ?
C8 C9 C12 121.7(4) . . ?
C4 C9 C12 121.0(4) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.0(3) . . ?
C18 C13 N2 118.9(3) . . ?
C14 C13 N2 119.0(3) . . ?
C13 C14 C15 116.6(4) . . ?
C13 C14 C19 122.1(3) . . ?
C15 C14 C19 121.3(4) . . ?
C16 C15 C14 122.6(4) . . ?
C16 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C17 C16 C15 118.1(4) . . ?
C17 C16 C20 121.3(4) . . ?
C15 C16 C20 120.6(4) . . ?
C16 C17 C18 122.8(4) . . ?
C16 C17 H17 118.6 . . ?
C18 C17 H17 118.6 . . ?
C17 C18 C13 117.9(4) . . ?
C17 C18 C21 120.6(4) . . ?
C13 C18 C21 121.4(3) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 N3 112.4(3) . . ?
N4 C23 S2 131.0(3) . . ?
N3 C23 S2 116.6(3) . . ?
O3 C24 N4 113.2(3) . . ?
O3 C24 C25 106.7(3) . . ?
N4 C24 C25 102.5(3) . . ?
O3 C24 H24 111.3 . . ?
N4 C24 H24 111.3 . . ?
C25 C24 H24 111.3 . . ?
O4 C25 N3 112.1(3) . . ?
O4 C25 C24 106.8(3) . . ?
N3 C25 C24 103.6(3) . . ?
O4 C25 H25 111.3 . . ?
N3 C25 H25 111.3 . . ?
C24 C25 H25 111.3 . . ?
C31 C26 C27 122.0(4) . . ?
C31 C26 N3 118.0(4) . . ?
C27 C26 N3 120.0(4) . . ?
C28 C27 C26 116.9(4) . . ?
C28 C27 C32 121.3(4) . . ?
C26 C27 C32 121.8(4) . . ?
C29 C28 C27 122.8(4) . . ?
C29 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
C28 C29 C30 118.6(4) . . ?
C28 C29 C33 120.7(4) . . ?
C30 C29 C33 120.6(4) . . ?
C29 C30 C31 122.3(4) . . ?
C29 C30 H30 118.9 . . ?
C31 C30 H30 118.9 . . ?
C30 C31 C26 117.4(4) . . ?
C30 C31 C34 121.8(4) . . ?
C26 C31 C34 120.8(4) . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C29 C33 H33A 109.5 . . ?
C29 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C29 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C40 122.6(4) . . ?
C36 C35 N4 118.1(3) . . ?
C40 C35 N4 119.3(3) . . ?
C35 C36 C37 116.6(4) . . ?
C35 C36 C41 122.5(4) . . ?
C37 C36 C41 120.8(4) . . ?
C38 C37 C36 122.8(4) . . ?
C38 C37 H37 118.6 . . ?
C36 C37 H37 118.6 . . ?
C37 C38 C39 117.7(4) . . ?
C37 C38 C42 120.3(4) . . ?
C39 C38 C42 121.9(4) . . ?
C40 C39 C38 122.6(4) . . ?
C40 C39 H39 118.7 . . ?
C38 C39 H39 118.7 . . ?
C39 C40 C35 117.7(4) . . ?
C39 C40 C43 120.1(4) . . ?
C35 C40 C43 122.1(4) . . ?
C36 C41 H41A 109.5 . . ?
C36 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C36 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C40 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C40 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
S2 C44 H44A 109.5 . . ?
S2 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
S2 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C1 N1 C4 125.3(3) . . ?
C1 N1 C3 110.9(3) . . ?
C4 N1 C3 123.8(3) . . ?
C1 N2 C13 127.4(3) . . ?
C1 N2 C2 110.0(3) . . ?
C13 N2 C2 122.2(3) . . ?
C23 N3 C26 125.2(3) . . ?
C23 N3 C25 110.7(3) . . ?
C26 N3 C25 124.1(3) . . ?
C23 N4 C35 126.4(3) . . ?
C23 N4 C24 109.9(3) . . ?
C35 N4 C24 120.1(3) . . ?
C2 O1 B1 109.9(3) . . ?
C3 O2 B1 110.1(3) . . ?
C24 O3 B2 110.4(3) . . ?
C25 O4 B2 109.8(3) . . ?
C1 S1 C22 110.13(19) . . ?
C23 S2 C44 105.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 O2 1.2(4) . . . . ?
N2 C2 C3 O2 -117.3(3) . . . . ?
O1 C2 C3 N1 120.6(3) . . . . ?
N2 C2 C3 N1 2.0(3) . . . . ?
C9 C4 C5 C6 1.7(6) . . . . ?
N1 C4 C5 C6 -179.8(4) . . . . ?
C9 C4 C5 C10 179.8(4) . . . . ?
N1 C4 C5 C10 -1.7(6) . . . . ?
C4 C5 C6 C7 1.2(7) . . . . ?
C10 C5 C6 C7 -176.9(5) . . . . ?
C5 C6 C7 C8 -3.1(9) . . . . ?
C5 C6 C7 C11 175.0(5) . . . . ?
C6 C7 C8 C9 2.2(9) . . . . ?
C11 C7 C8 C9 -175.9(5) . . . . ?
C7 C8 C9 C4 0.5(8) . . . . ?
C7 C8 C9 C12 178.9(5) . . . . ?
C5 C4 C9 C8 -2.5(7) . . . . ?
N1 C4 C9 C8 179.1(4) . . . . ?
C5 C4 C9 C12 179.1(4) . . . . ?
N1 C4 C9 C12 0.6(6) . . . . ?
C18 C13 C14 C15 -1.3(5) . . . . ?
N2 C13 C14 C15 -179.1(3) . . . . ?
C18 C13 C14 C19 178.5(4) . . . . ?
N2 C13 C14 C19 0.7(5) . . . . ?
C13 C14 C15 C16 3.2(6) . . . . ?
C19 C14 C15 C16 -176.6(4) . . . . ?
C14 C15 C16 C17 -2.4(6) . . . . ?
C14 C15 C16 C20 177.1(4) . . . . ?
C15 C16 C17 C18 -0.5(6) . . . . ?
C20 C16 C17 C18 -179.9(4) . . . . ?
C16 C17 C18 C13 2.2(6) . . . . ?
C16 C17 C18 C21 -179.6(4) . . . . ?
C14 C13 C18 C17 -1.3(5) . . . . ?
N2 C13 C18 C17 176.5(3) . . . . ?
C14 C13 C18 C21 -179.4(3) . . . . ?
N2 C13 C18 C21 -1.6(5) . . . . ?
O3 C24 C25 O4 -8.9(4) . . . . ?
N4 C24 C25 O4 110.3(3) . . . . ?
O3 C24 C25 N3 -127.4(3) . . . . ?
N4 C24 C25 N3 -8.2(4) . . . . ?
C31 C26 C27 C28 0.6(6) . . . . ?
N3 C26 C27 C28 -178.5(3) . . . . ?
C31 C26 C27 C32 177.7(4) . . . . ?
N3 C26 C27 C32 -1.4(6) . . . . ?
C26 C27 C28 C29 -1.9(6) . . . . ?
C32 C27 C28 C29 -179.1(4) . . . . ?
C27 C28 C29 C30 2.1(6) . . . . ?
C27 C28 C29 C33 -179.4(4) . . . . ?
C28 C29 C30 C31 -0.9(6) . . . . ?
C33 C29 C30 C31 -179.4(4) . . . . ?
C29 C30 C31 C26 -0.4(6) . . . . ?
C29 C30 C31 C34 175.8(4) . . . . ?
C27 C26 C31 C30 0.5(6) . . . . ?
N3 C26 C31 C30 179.6(3) . . . . ?
C27 C26 C31 C34 -175.7(4) . . . . ?
N3 C26 C31 C34 3.4(6) . . . . ?
C40 C35 C36 C37 0.1(6) . . . . ?
N4 C35 C36 C37 -179.8(3) . . . . ?
C40 C35 C36 C41 177.2(4) . . . . ?
N4 C35 C36 C41 -2.8(5) . . . . ?
C35 C36 C37 C38 -0.2(6) . . . . ?
C41 C36 C37 C38 -177.3(4) . . . . ?
C36 C37 C38 C39 -0.2(6) . . . . ?
C36 C37 C38 C42 177.8(4) . . . . ?
C37 C38 C39 C40 0.7(6) . . . . ?
C42 C38 C39 C40 -177.3(4) . . . . ?
C38 C39 C40 C35 -0.7(6) . . . . ?
C38 C39 C40 C43 177.8(4) . . . . ?
C36 C35 C40 C39 0.3(6) . . . . ?
N4 C35 C40 C39 -179.7(3) . . . . ?
C36 C35 C40 C43 -178.2(4) . . . . ?
N4 C35 C40 C43 1.8(6) . . . . ?
N2 C1 N1 C4 -179.2(3) . . . . ?
S1 C1 N1 C4 -0.1(5) . . . . ?
N2 C1 N1 C3 -0.5(4) . . . . ?
S1 C1 N1 C3 178.6(2) . . . . ?
C9 C4 N1 C1 -84.1(5) . . . . ?
C5 C4 N1 C1 97.3(5) . . . . ?
C9 C4 N1 C3 97.4(5) . . . . ?
C5 C4 N1 C3 -81.2(5) . . . . ?
O2 C3 N1 C1 114.5(3) . . . . ?
C2 C3 N1 C1 -1.1(4) . . . . ?
O2 C3 N1 C4 -66.9(4) . . . . ?
C2 C3 N1 C4 177.6(3) . . . . ?
N1 C1 N2 C13 175.6(3) . . . . ?
S1 C1 N2 C13 -3.3(5) . . . . ?
N1 C1 N2 C2 2.0(4) . . . . ?
S1 C1 N2 C2 -177.0(3) . . . . ?
C18 C13 N2 C1 -84.8(4) . . . . ?
C14 C13 N2 C1 93.0(4) . . . . ?
C18 C13 N2 C2 88.2(4) . . . . ?
C14 C13 N2 C2 -94.0(4) . . . . ?
O1 C2 N2 C1 -116.6(3) . . . . ?
C3 C2 N2 C1 -2.5(4) . . . . ?
O1 C2 N2 C13 69.3(4) . . . . ?
C3 C2 N2 C13 -176.5(3) . . . . ?
N4 C23 N3 C26 -179.2(3) . . . . ?
S2 C23 N3 C26 2.8(5) . . . . ?
N4 C23 N3 C25 0.2(4) . . . . ?
S2 C23 N3 C25 -177.9(3) . . . . ?
C31 C26 N3 C23 -99.9(4) . . . . ?
C27 C26 N3 C23 79.3(5) . . . . ?
C31 C26 N3 C25 80.8(5) . . . . ?
C27 C26 N3 C25 -100.0(4) . . . . ?
O4 C25 N3 C23 -109.3(4) . . . . ?
C24 C25 N3 C23 5.5(4) . . . . ?
O4 C25 N3 C26 70.1(5) . . . . ?
C24 C25 N3 C26 -175.1(3) . . . . ?
N3 C23 N4 C35 -164.6(3) . . . . ?
S2 C23 N4 C35 13.2(6) . . . . ?
N3 C23 N4 C24 -6.1(4) . . . . ?
S2 C23 N4 C24 171.7(3) . . . . ?
C36 C35 N4 C23 72.3(5) . . . . ?
C40 C35 N4 C23 -107.6(5) . . . . ?
C36 C35 N4 C24 -84.2(4) . . . . ?
C40 C35 N4 C24 95.8(4) . . . . ?
O3 C24 N4 C23 123.5(3) . . . . ?
C25 C24 N4 C23 8.9(4) . . . . ?
O3 C24 N4 C35 -76.5(4) . . . . ?
C25 C24 N4 C35 169.0(3) . . . . ?
N2 C2 O1 B1 104.7(3) . . . . ?
C3 C2 O1 B1 -7.4(4) . . . . ?
F2 B1 O1 C2 130.2(3) . . . . ?
F1 B1 O1 C2 -110.5(4) . . . . ?
O2 B1 O1 C2 10.7(4) . . . . ?
N1 C3 O2 B1 -107.4(4) . . . . ?
C2 C3 O2 B1 5.6(4) . . . . ?
F2 B1 O2 C3 -128.8(3) . . . . ?
F1 B1 O2 C3 110.9(4) . . . . ?
O1 B1 O2 C3 -9.9(4) . . . . ?
N4 C24 O3 B2 -99.3(4) . . . . ?
C25 C24 O3 B2 12.6(4) . . . . ?
F3 B2 O3 C24 109.7(4) . . . . ?
F4 B2 O3 C24 -130.0(4) . . . . ?
O4 B2 O3 C24 -11.5(4) . . . . ?
N3 C25 O4 B2 114.7(4) . . . . ?
C24 C25 O4 B2 1.8(4) . . . . ?
F3 B2 O4 C25 -116.0(4) . . . . ?
F4 B2 O4 C25 123.8(3) . . . . ?
O3 B2 O4 C25 5.4(4) . . . . ?
N1 C1 S1 C22 -168.7(3) . . . . ?
N2 C1 S1 C22 10.2(4) . . . . ?
N4 C23 S2 C44 15.8(4) . . . . ?
N3 C23 S2 C44 -166.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.070
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.067

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.298 0.352 0.778 176 50 ' '
2 0.702 0.648 0.222 176 51 ' '
_platon_squeeze_details          
;
;

####################################################################### 
# 
# 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_viv
_database_code_depnum_ccdc_archive 'CCDC 1063843'
_audit_update_record             
;
2015-05-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 N2 O2 S'
_chemical_formula_sum            'C22 H28 N2 O2 S'
_chemical_formula_weight         384.53

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_HALL  '-C 2yc'

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

_cell_length_a                   41.799(8)
_cell_length_b                   7.8933(16)
_cell_length_c                   26.972(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.32(3)
_cell_angle_gamma                90.00
_cell_volume                     8448(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3296
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27768
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_sigmaI/netI    0.1038
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.50
_reflns_number_total             7861
_reflns_number_gt                4190
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0709P)²+7.1494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7861
_refine_ls_number_parameters     503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1721
_refine_ls_wR_factor_gt          0.1406
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.13680(9) 0.4477(5) 0.46073(14) 0.0287(9) Uani 1 1 d . . .
C2 C 0.18271(9) 0.5817(5) 0.52056(14) 0.0353(10) Uani 1 1 d . . .
H2 H 0.1865 0.7043 0.5233 0.042 Uiso 1 1 calc R . .
C3 C 0.15730(9) 0.5280(5) 0.54811(15) 0.0351(9) Uani 1 1 d . . .
H3 H 0.1678 0.4502 0.5770 0.042 Uiso 1 1 calc R . .
C4 C 0.17475(9) 0.6063(5) 0.42413(14) 0.0310(9) Uani 1 1 d . . .
C5 C 0.19720(9) 0.5226(5) 0.40404(15) 0.0387(10) Uani 1 1 d . . .
C6 C 0.20665(11) 0.6056(7) 0.36493(17) 0.0527(13) Uani 1 1 d . . .
H6 H 0.2218 0.5531 0.3510 0.063 Uiso 1 1 calc R . .
C7 C 0.19430(13) 0.7610(7) 0.34668(17) 0.0555(13) Uani 1 1 d . . .
C8 C 0.17124(11) 0.8367(6) 0.36592(16) 0.0517(13) Uani 1 1 d . . .
H8 H 0.1625 0.9419 0.3530 0.062 Uiso 1 1 calc R . .
C9 C 0.16044(10) 0.7604(5) 0.40431(16) 0.0389(10) Uani 1 1 d . . .
C10 C 0.21032(11) 0.3503(6) 0.42140(18) 0.0565(13) Uani 1 1 d . . .
H10A H 0.2113 0.3342 0.4571 0.085 Uiso 1 1 calc R . .
H10B H 0.2325 0.3385 0.4184 0.085 Uiso 1 1 calc R . .
H10C H 0.1956 0.2671 0.3999 0.085 Uiso 1 1 calc R . .
C11 C 0.20734(16) 0.8513(8) 0.30703(19) 0.099(2) Uani 1 1 d . . .
H11A H 0.2240 0.9335 0.3246 0.149 Uiso 1 1 calc R . .
H11B H 0.1890 0.9073 0.2817 0.149 Uiso 1 1 calc R . .
H11C H 0.2173 0.7701 0.2898 0.149 Uiso 1 1 calc R . .
C12 C 0.13368(11) 0.8395(6) 0.42275(19) 0.0602(14) Uani 1 1 d . . .
H12A H 0.1135 0.7727 0.4110 0.090 Uiso 1 1 calc R . .
H12B H 0.1291 0.9521 0.4088 0.090 Uiso 1 1 calc R . .
H12C H 0.1412 0.8444 0.4602 0.090 Uiso 1 1 calc R . .
C13 C 0.10558(9) 0.3414(5) 0.51773(13) 0.0310(9) Uani 1 1 d . . .
C14 C 0.07385(10) 0.4112(5) 0.51037(14) 0.0349(10) Uani 1 1 d . . .
C15 C 0.05048(10) 0.3110(6) 0.52367(14) 0.0398(11) Uani 1 1 d . . .
H15 H 0.0290 0.3542 0.5189 0.048 Uiso 1 1 calc R . .
C16 C 0.05796(10) 0.1489(6) 0.54386(14) 0.0419(11) Uani 1 1 d . . .
C17 C 0.08970(10) 0.0844(6) 0.54889(15) 0.0422(11) Uani 1 1 d . . .
H17 H 0.0949 -0.0251 0.5616 0.051 Uiso 1 1 calc R . .
C18 C 0.11371(10) 0.1770(5) 0.53571(14) 0.0338(9) Uani 1 1 d . . .
C19 C 0.06500(10) 0.5861(5) 0.48858(15) 0.0413(11) Uani 1 1 d . . .
H19A H 0.0437 0.6189 0.4919 0.062 Uiso 1 1 calc R . .
H19B H 0.0636 0.5869 0.4524 0.062 Uiso 1 1 calc R . .
H19C H 0.0821 0.6643 0.5075 0.062 Uiso 1 1 calc R . .
C20 C 0.03278(11) 0.0476(7) 0.56150(17) 0.0615(14) Uani 1 1 d . . .
H20A H 0.0111 0.1009 0.5491 0.092 Uiso 1 1 calc R . .
H20B H 0.0400 0.0427 0.5990 0.092 Uiso 1 1 calc R . .
H20C H 0.0313 -0.0652 0.5476 0.092 Uiso 1 1 calc R . .
C21 C 0.14789(11) 0.1032(5) 0.54061(16) 0.0471(11) Uani 1 1 d . . .
H21A H 0.1650 0.1692 0.5650 0.071 Uiso 1 1 calc R . .
H21B H 0.1514 0.1051 0.5071 0.071 Uiso 1 1 calc R . .
H21C H 0.1489 -0.0115 0.5528 0.071 Uiso 1 1 calc R . .
C22 C 0.24196(13) 0.5774(9) 0.5450(3) 0.130(3) Uani 1 1 d . . .
H22A H 0.2428 0.5973 0.5103 0.195 Uiso 1 1 calc R . .
H22B H 0.2610 0.5100 0.5640 0.195 Uiso 1 1 calc R . .
H22C H 0.2426 0.6838 0.5625 0.195 Uiso 1 1 calc R . .
C23 C 0.09580(8) 0.3788(4) 0.18881(13) 0.0258(8) Uani 1 1 d . . .
C24 C 0.11901(9) 0.4695(5) 0.27403(13) 0.0301(9) Uani 1 1 d . . .
H24 H 0.1248 0.5831 0.2887 0.036 Uiso 1 1 calc R . .
C25 C 0.08139(8) 0.4305(5) 0.26373(13) 0.0274(9) Uani 1 1 d . . .
H25 H 0.0783 0.3501 0.2896 0.033 Uiso 1 1 calc R . .
C26 C 0.14882(9) 0.5373(5) 0.20720(13) 0.0292(9) Uani 1 1 d . . .
C27 C 0.14334(10) 0.7022(5) 0.18841(14) 0.0363(10) Uani 1 1 d . . .
C28 C 0.16907(10) 0.7796(6) 0.17398(15) 0.0429(11) Uani 1 1 d . . .
H28 H 0.1659 0.8897 0.1611 0.051 Uiso 1 1 calc R . .
C29 C 0.19895(10) 0.6991(6) 0.17809(15) 0.0444(11) Uani 1 1 d . . .
C30 C 0.20299(9) 0.5351(6) 0.19604(16) 0.0465(12) Uani 1 1 d . . .
H30 H 0.2229 0.4785 0.1982 0.056 Uiso 1 1 calc R . .
C31 C 0.17833(9) 0.4510(6) 0.21105(15) 0.0376(10) Uani 1 1 d . . .
C32 C 0.11063(10) 0.7908(5) 0.18260(18) 0.0523(12) Uani 1 1 d . . .
H32A H 0.0927 0.7337 0.1567 0.078 Uiso 1 1 calc R . .
H32B H 0.1120 0.9059 0.1719 0.078 Uiso 1 1 calc R . .
H32C H 0.1062 0.7896 0.2154 0.078 Uiso 1 1 calc R . .
C33 C 0.22639(10) 0.7886(7) 0.16276(18) 0.0628(14) Uani 1 1 d . . .
H33A H 0.2470 0.7861 0.1915 0.094 Uiso 1 1 calc R . .
H33B H 0.2199 0.9041 0.1538 0.094 Uiso 1 1 calc R . .
H33C H 0.2297 0.7325 0.1332 0.094 Uiso 1 1 calc R . .
C34 C 0.18286(10) 0.2692(6) 0.22874(18) 0.0555(13) Uani 1 1 d . . .
H34A H 0.1831 0.2622 0.2644 0.083 Uiso 1 1 calc R . .
H34B H 0.2038 0.2270 0.2260 0.083 Uiso 1 1 calc R . .
H34C H 0.1646 0.2025 0.2071 0.083 Uiso 1 1 calc R . .
C35 C 0.04081(8) 0.2676(5) 0.18869(14) 0.0264(9) Uani 1 1 d . . .
C36 C 0.03697(9) 0.1044(5) 0.20574(14) 0.0297(9) Uani 1 1 d . . .
C37 C 0.00768(9) 0.0174(5) 0.18020(14) 0.0338(10) Uani 1 1 d . . .
H37 H 0.0048 -0.0921 0.1909 0.041 Uiso 1 1 calc R . .
C38 C -0.01748(9) 0.0884(5) 0.13927(15) 0.0337(10) Uani 1 1 d . . .
C39 C -0.01323(9) 0.2528(5) 0.12508(15) 0.0345(10) Uani 1 1 d . . .
H39 H -0.0303 0.3023 0.0981 0.041 Uiso 1 1 calc R . .
C40 C 0.01528(9) 0.3470(5) 0.14920(14) 0.0303(9) Uani 1 1 d . . .
C41 C 0.06391(10) 0.0249(5) 0.25080(15) 0.0399(10) Uani 1 1 d . . .
H41A H 0.0857 0.0604 0.2500 0.060 Uiso 1 1 calc R . .
H41B H 0.0623 -0.0962 0.2480 0.060 Uiso 1 1 calc R . .
H41C H 0.0609 0.0601 0.2831 0.060 Uiso 1 1 calc R . .
C42 C -0.04839(9) -0.0103(5) 0.10932(16) 0.0464(11) Uani 1 1 d . . .
H42A H -0.0666 0.0168 0.1225 0.070 Uiso 1 1 calc R . .
H42B H -0.0437 -0.1294 0.1134 0.070 Uiso 1 1 calc R . .
H42C H -0.0546 0.0189 0.0730 0.070 Uiso 1 1 calc R . .
C43 C 0.01901(9) 0.5261(5) 0.13310(16) 0.0397(10) Uani 1 1 d . . .
H43A H 0.0334 0.5281 0.1114 0.060 Uiso 1 1 calc R . .
H43B H 0.0288 0.5941 0.1636 0.060 Uiso 1 1 calc R . .
H43C H -0.0027 0.5706 0.1139 0.060 Uiso 1 1 calc R . .
C44 C 0.0447(2) 0.5835(9) 0.2954(3) 0.153(4) Uani 1 1 d . . .
H44A H 0.0595 0.5860 0.3307 0.230 Uiso 1 1 calc R . .
H44B H 0.0307 0.4846 0.2903 0.230 Uiso 1 1 calc R . .
H44C H 0.0308 0.6831 0.2887 0.230 Uiso 1 1 calc R . .
N1 N 0.13116(7) 0.4417(4) 0.50683(11) 0.0302(7) Uani 1 1 d . . .
N2 N 0.16596(7) 0.5322(4) 0.46639(11) 0.0323(8) Uani 1 1 d . . .
N3 N 0.07210(7) 0.3541(4) 0.21225(11) 0.0252(7) Uani 1 1 d . . .
N4 N 0.12264(7) 0.4563(4) 0.22254(11) 0.0283(7) Uani 1 1 d . . .
O1 O 0.21295(7) 0.4939(4) 0.54245(12) 0.0551(8) Uani 1 1 d . . .
O2 O 0.14572(7) 0.6729(3) 0.56631(10) 0.0406(7) Uani 1 1 d . . .
H2A H 0.1377 0.6469 0.5893 0.061 Uiso 1 1 calc R . .
O3 O 0.13957(6) 0.3446(4) 0.30599(9) 0.0395(7) Uani 1 1 d . . .
H3A H 0.1382 0.3514 0.3356 0.059 Uiso 1 1 calc R . .
O4 O 0.06270(7) 0.5792(3) 0.26289(10) 0.0407(7) Uani 1 1 d . . .
S1 S 0.11221(2) 0.36096(14) 0.40546(4) 0.0362(3) Uani 1 1 d . . .
S2 S 0.09258(2) 0.32099(14) 0.12798(4) 0.0369(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.337(4) . ?
C1 N2 1.355(4) . ?
C1 S1 1.669(4) . ?
C2 O1 1.399(4) . ?
C2 N2 1.461(4) . ?
C2 C3 1.535(5) . ?
C2 H2 0.9800 . ?
C3 O2 1.390(4) . ?
C3 N1 1.460(4) . ?
C3 H3 0.9800 . ?
C4 C9 1.386(5) . ?
C4 C5 1.390(5) . ?
C4 N2 1.428(4) . ?
C5 C6 1.400(6) . ?
C5 C10 1.486(6) . ?
C6 C7 1.361(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(6) . ?
C7 C11 1.522(6) . ?
C8 C9 1.390(6) . ?
C8 H8 0.9300 . ?
C9 C12 1.496(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.390(5) . ?
C13 C14 1.391(5) . ?
C13 N1 1.433(4) . ?
C14 C15 1.389(5) . ?
C14 C19 1.501(5) . ?
C15 C16 1.387(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(6) . ?
C16 C20 1.513(5) . ?
C17 C18 1.375(5) . ?
C17 H17 0.9300 . ?
C18 C21 1.509(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O1 1.363(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N3 1.346(4) . ?
C23 N4 1.349(4) . ?
C23 S2 1.667(4) . ?
C24 O3 1.410(4) . ?
C24 N4 1.448(4) . ?
C24 C25 1.539(5) . ?
C24 H24 0.9800 . ?
C25 O4 1.406(4) . ?
C25 N3 1.450(4) . ?
C25 H25 0.9800 . ?
C26 C31 1.384(5) . ?
C26 C27 1.390(5) . ?
C26 N4 1.436(4) . ?
C27 C28 1.394(5) . ?
C27 C32 1.500(5) . ?
C28 C29 1.374(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.374(6) . ?
C29 C33 1.511(5) . ?
C30 C31 1.389(5) . ?
C30 H30 0.9300 . ?
C31 C34 1.505(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.394(5) . ?
C35 C40 1.397(5) . ?
C35 N3 1.435(4) . ?
C36 C37 1.384(5) . ?
C36 C41 1.509(5) . ?
C37 C38 1.382(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.380(5) . ?
C38 C42 1.508(5) . ?
C39 C40 1.382(5) . ?
C39 H39 0.9300 . ?
C40 C43 1.501(5) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 O4 1.322(5) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
O2 H2A 0.8200 . ?
O3 H3A 0.8200 . ?

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
N1 C1 N2 109.1(3) . . ?
N1 C1 S1 125.2(3) . . ?
N2 C1 S1 125.6(3) . . ?
O1 C2 N2 112.0(3) . . ?
O1 C2 C3 109.2(3) . . ?
N2 C2 C3 102.9(3) . . ?
O1 C2 H2 110.8 . . ?
N2 C2 H2 110.8 . . ?
C3 C2 H2 110.8 . . ?
O2 C3 N1 113.1(3) . . ?
O2 C3 C2 108.3(3) . . ?
N1 C3 C2 103.0(3) . . ?
O2 C3 H3 110.7 . . ?
N1 C3 H3 110.7 . . ?
C2 C3 H3 110.7 . . ?
C9 C4 C5 122.0(4) . . ?
C9 C4 N2 118.6(3) . . ?
C5 C4 N2 119.4(4) . . ?
C4 C5 C6 117.1(4) . . ?
C4 C5 C10 122.7(4) . . ?
C6 C5 C10 120.2(4) . . ?
C7 C6 C5 122.0(4) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 119.3(4) . . ?
C6 C7 C11 119.8(5) . . ?
C8 C7 C11 120.9(6) . . ?
C7 C8 C9 121.8(5) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C4 C9 C8 117.7(4) . . ?
C4 C9 C12 121.0(4) . . ?
C8 C9 C12 121.3(4) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.5(4) . . ?
C18 C13 N1 118.1(3) . . ?
C14 C13 N1 119.4(3) . . ?
C15 C14 C13 117.0(4) . . ?
C15 C14 C19 121.2(4) . . ?
C13 C14 C19 121.8(3) . . ?
C16 C15 C14 122.4(4) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C17 C16 C15 117.9(4) . . ?
C17 C16 C20 120.9(4) . . ?
C15 C16 C20 121.2(4) . . ?
C18 C17 C16 122.2(4) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C13 117.9(4) . . ?
C17 C18 C21 121.3(4) . . ?
C13 C18 C21 120.8(3) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 N4 109.1(3) . . ?
N3 C23 S2 125.4(3) . . ?
N4 C23 S2 125.5(3) . . ?
O3 C24 N4 108.0(3) . . ?
O3 C24 C25 111.3(3) . . ?
N4 C24 C25 102.8(3) . . ?
O3 C24 H24 111.5 . . ?
N4 C24 H24 111.5 . . ?
C25 C24 H24 111.5 . . ?
O4 C25 N3 110.6(3) . . ?
O4 C25 C24 111.5(3) . . ?
N3 C25 C24 101.9(3) . . ?
O4 C25 H25 110.8 . . ?
N3 C25 H25 110.8 . . ?
C24 C25 H25 110.8 . . ?
C31 C26 C27 122.0(4) . . ?
C31 C26 N4 120.1(4) . . ?
C27 C26 N4 118.0(3) . . ?
C26 C27 C28 117.3(4) . . ?
C26 C27 C32 121.0(3) . . ?
C28 C27 C32 121.6(4) . . ?
C29 C28 C27 122.4(4) . . ?
C29 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C30 C29 C28 118.2(4) . . ?
C30 C29 C33 121.1(4) . . ?
C28 C29 C33 120.7(4) . . ?
C29 C30 C31 122.2(4) . . ?
C29 C30 H30 118.9 . . ?
C31 C30 H30 118.9 . . ?
C26 C31 C30 117.9(4) . . ?
C26 C31 C34 120.9(4) . . ?
C30 C31 C34 121.1(4) . . ?
C27 C32 H32A 109.5 . . ?
C27 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C27 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C29 C33 H33A 109.5 . . ?
C29 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C29 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C40 121.8(3) . . ?
C36 C35 N3 118.5(3) . . ?
C40 C35 N3 119.7(3) . . ?
C37 C36 C35 118.0(3) . . ?
C37 C36 C41 121.0(3) . . ?
C35 C36 C41 121.0(3) . . ?
C38 C37 C36 121.9(4) . . ?
C38 C37 H37 119.0 . . ?
C36 C37 H37 119.0 . . ?
C39 C38 C37 118.1(3) . . ?
C39 C38 C42 120.0(4) . . ?
C37 C38 C42 121.8(4) . . ?
C38 C39 C40 122.9(4) . . ?
C38 C39 H39 118.6 . . ?
C40 C39 H39 118.6 . . ?
C39 C40 C35 117.2(4) . . ?
C39 C40 C43 121.6(3) . . ?
C35 C40 C43 121.3(3) . . ?
C36 C41 H41A 109.5 . . ?
C36 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C36 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 H42A 109.5 . . ?
C38 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C38 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C40 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C40 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O4 C44 H44A 109.5 . . ?
O4 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
O4 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C1 N1 C13 124.8(3) . . ?
C1 N1 C3 112.6(3) . . ?
C13 N1 C3 121.9(3) . . ?
C1 N2 C4 124.0(3) . . ?
C1 N2 C2 112.1(3) . . ?
C4 N2 C2 121.8(3) . . ?
C23 N3 C35 124.3(3) . . ?
C23 N3 C25 112.0(3) . . ?
C35 N3 C25 123.7(3) . . ?
C23 N4 C26 123.7(3) . . ?
C23 N4 C24 111.4(3) . . ?
C26 N4 C24 124.3(3) . . ?
C22 O1 C2 116.9(4) . . ?
C3 O2 H2A 109.5 . . ?
C24 O3 H3A 109.5 . . ?
C44 O4 C25 116.1(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
O1 C2 C3 O2 125.7(3) . . . . ?
N2 C2 C3 O2 -115.1(3) . . . . ?
O1 C2 C3 N1 -114.2(3) . . . . ?
N2 C2 C3 N1 5.0(4) . . . . ?
C9 C4 C5 C6 4.1(6) . . . . ?
N2 C4 C5 C6 -176.0(3) . . . . ?
C9 C4 C5 C10 -174.2(4) . . . . ?
N2 C4 C5 C10 5.7(6) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
C10 C5 C6 C7 177.7(4) . . . . ?
C5 C6 C7 C8 -1.9(7) . . . . ?
C5 C6 C7 C11 175.5(4) . . . . ?
C6 C7 C8 C9 1.1(6) . . . . ?
C11 C7 C8 C9 -176.3(4) . . . . ?
C5 C4 C9 C8 -4.9(6) . . . . ?
N2 C4 C9 C8 175.2(3) . . . . ?
C5 C4 C9 C12 173.6(4) . . . . ?
N2 C4 C9 C12 -6.3(5) . . . . ?
C7 C8 C9 C4 2.2(6) . . . . ?
C7 C8 C9 C12 -176.3(4) . . . . ?
C18 C13 C14 C15 2.3(5) . . . . ?
N1 C13 C14 C15 -177.3(3) . . . . ?
C18 C13 C14 C19 -177.1(3) . . . . ?
N1 C13 C14 C19 3.3(5) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
C19 C14 C15 C16 180.0(3) . . . . ?
C14 C15 C16 C17 -2.4(6) . . . . ?
C14 C15 C16 C20 175.7(4) . . . . ?
C15 C16 C17 C18 1.5(6) . . . . ?
C20 C16 C17 C18 -176.6(4) . . . . ?
C16 C17 C18 C13 1.2(6) . . . . ?
C16 C17 C18 C21 -178.9(4) . . . . ?
C14 C13 C18 C17 -3.2(5) . . . . ?
N1 C13 C18 C17 176.4(3) . . . . ?
C14 C13 C18 C21 176.9(3) . . . . ?
N1 C13 C18 C21 -3.5(5) . . . . ?
O3 C24 C25 O4 142.7(3) . . . . ?
N4 C24 C25 O4 -102.0(3) . . . . ?
O3 C24 C25 N3 -99.3(3) . . . . ?
N4 C24 C25 N3 16.0(3) . . . . ?
C31 C26 C27 C28 -0.8(6) . . . . ?
N4 C26 C27 C28 179.6(3) . . . . ?
C31 C26 C27 C32 177.6(4) . . . . ?
N4 C26 C27 C32 -2.0(5) . . . . ?
C26 C27 C28 C29 -0.4(6) . . . . ?
C32 C27 C28 C29 -178.7(4) . . . . ?
C27 C28 C29 C30 1.5(6) . . . . ?
C27 C28 C29 C33 -179.1(4) . . . . ?
C28 C29 C30 C31 -1.4(6) . . . . ?
C33 C29 C30 C31 179.1(4) . . . . ?
C27 C26 C31 C30 0.8(6) . . . . ?
N4 C26 C31 C30 -179.6(3) . . . . ?
C27 C26 C31 C34 -176.6(4) . . . . ?
N4 C26 C31 C34 3.0(5) . . . . ?
C29 C30 C31 C26 0.3(6) . . . . ?
C29 C30 C31 C34 177.8(4) . . . . ?
C40 C35 C36 C37 3.9(5) . . . . ?
N3 C35 C36 C37 -175.4(3) . . . . ?
C40 C35 C36 C41 -176.0(3) . . . . ?
N3 C35 C36 C41 4.7(5) . . . . ?
C35 C36 C37 C38 -0.6(5) . . . . ?
C41 C36 C37 C38 179.2(3) . . . . ?
C36 C37 C38 C39 -2.0(5) . . . . ?
C36 C37 C38 C42 176.1(3) . . . . ?
C37 C38 C39 C40 1.5(6) . . . . ?
C42 C38 C39 C40 -176.6(3) . . . . ?
C38 C39 C40 C35 1.6(5) . . . . ?
C38 C39 C40 C43 -179.5(4) . . . . ?
C36 C35 C40 C39 -4.3(5) . . . . ?
N3 C35 C40 C39 175.0(3) . . . . ?
C36 C35 C40 C43 176.8(3) . . . . ?
N3 C35 C40 C43 -3.9(5) . . . . ?
N2 C1 N1 C13 -170.2(3) . . . . ?
S1 C1 N1 C13 8.6(5) . . . . ?
N2 C1 N1 C3 0.7(4) . . . . ?
S1 C1 N1 C3 179.5(3) . . . . ?
C18 C13 N1 C1 89.5(4) . . . . ?
C14 C13 N1 C1 -90.9(4) . . . . ?
C18 C13 N1 C3 -80.6(4) . . . . ?
C14 C13 N1 C3 99.0(4) . . . . ?
O2 C3 N1 C1 113.0(3) . . . . ?
C2 C3 N1 C1 -3.8(4) . . . . ?
O2 C3 N1 C13 -75.8(4) . . . . ?
C2 C3 N1 C13 167.4(3) . . . . ?
N1 C1 N2 C4 -160.5(3) . . . . ?
S1 C1 N2 C4 20.8(5) . . . . ?
N1 C1 N2 C2 3.0(4) . . . . ?
S1 C1 N2 C2 -175.8(3) . . . . ?
C9 C4 N2 C1 78.7(5) . . . . ?
C5 C4 N2 C1 -101.3(4) . . . . ?
C9 C4 N2 C2 -83.2(4) . . . . ?
C5 C4 N2 C2 96.8(4) . . . . ?
O1 C2 N2 C1 112.1(4) . . . . ?
C3 C2 N2 C1 -5.1(4) . . . . ?
O1 C2 N2 C4 -84.0(4) . . . . ?
C3 C2 N2 C4 158.8(3) . . . . ?
N4 C23 N3 C35 -176.9(3) . . . . ?
S2 C23 N3 C35 2.6(5) . . . . ?
N4 C23 N3 C25 5.0(4) . . . . ?
S2 C23 N3 C25 -175.5(3) . . . . ?
C36 C35 N3 C23 105.8(4) . . . . ?
C40 C35 N3 C23 -73.5(5) . . . . ?
C36 C35 N3 C25 -76.4(4) . . . . ?
C40 C35 N3 C25 104.3(4) . . . . ?
O4 C25 N3 C23 105.2(3) . . . . ?
C24 C25 N3 C23 -13.5(4) . . . . ?
O4 C25 N3 C35 -72.9(4) . . . . ?
C24 C25 N3 C35 168.4(3) . . . . ?
N3 C23 N4 C26 -164.6(3) . . . . ?
S2 C23 N4 C26 15.9(5) . . . . ?
N3 C23 N4 C24 6.8(4) . . . . ?
S2 C23 N4 C24 -172.7(3) . . . . ?
C31 C26 N4 C23 -96.5(4) . . . . ?
C27 C26 N4 C23 83.1(5) . . . . ?
C31 C26 N4 C24 93.3(4) . . . . ?
C27 C26 N4 C24 -87.2(4) . . . . ?
O3 C24 N4 C23 103.1(3) . . . . ?
C25 C24 N4 C23 -14.6(4) . . . . ?
O3 C24 N4 C26 -85.6(4) . . . . ?
C25 C24 N4 C26 156.7(3) . . . . ?
N2 C2 O1 C22 100.4(5) . . . . ?
C3 C2 O1 C22 -146.2(5) . . . . ?
N3 C25 O4 C44 122.6(5) . . . . ?
C24 C25 O4 C44 -124.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_24julb
_database_code_depnum_ccdc_archive 'CCDC 1401392'
_audit_update_record             
;
2015-05-18 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H46 N4 O4 S2'
_chemical_formula_sum            'C42 H46 N4 O4 S2'
_chemical_formula_weight         734.97

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
_symmetry_space_group_name_H-M   Fdd2
_symmetry_space_group_name_HALL  F2-2d

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   20.261(4)
_cell_length_b                   46.298(9)
_cell_length_c                   8.3561(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7839(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3120
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9874
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10707
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0579
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3829
_reflns_number_gt                3365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 3.2d'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_number_reflns         3829
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.93564(13) 0.03055(5) 0.8688(3) 0.0209(5) Uani 1 1 d . . .
H1 H 0.9416 0.0193 0.7705 0.025 Uiso 1 1 calc R . .
C2 C 0.83725(14) 0.05273(6) 0.9477(3) 0.0232(6) Uani 1 1 d . . .
C3 C 0.88500(13) 0.07589(6) 0.8838(3) 0.0236(6) Uani 1 1 d . . .
C4 C 0.84238(13) -0.00074(5) 0.9729(3) 0.0216(6) Uani 1 1 d . . .
C5 C 0.82742(13) -0.02042(5) 0.8504(3) 0.0218(6) Uani 1 1 d . . .
C6 C 0.80307(13) -0.04733(6) 0.8931(4) 0.0272(6) Uani 1 1 d . . .
H6 H 0.7926 -0.0605 0.8132 0.033 Uiso 1 1 calc R . .
C7 C 0.79382(14) -0.05514(6) 1.0527(4) 0.0272(7) Uani 1 1 d . . .
C8 C 0.80956(14) -0.03509(6) 1.1710(4) 0.0293(7) Uani 1 1 d . . .
H8 H 0.8036 -0.0401 1.2779 0.035 Uiso 1 1 calc R . .
C9 C 0.83394(13) -0.00790(6) 1.1337(3) 0.0237(6) Uani 1 1 d . . .
C10 C 0.85069(15) 0.01341(7) 1.2644(4) 0.0328(7) Uani 1 1 d . . .
H10A H 0.8476 0.0040 1.3666 0.049 Uiso 1 1 calc R . .
H10B H 0.8203 0.0293 1.2607 0.049 Uiso 1 1 calc R . .
H10C H 0.8948 0.0204 1.2490 0.049 Uiso 1 1 calc R . .
C11 C 0.83717(15) -0.01336(6) 0.6768(3) 0.0292(7) Uani 1 1 d . . .
H11A H 0.8810 -0.0187 0.6450 0.044 Uiso 1 1 calc R . .
H11B H 0.8312 0.0070 0.6607 0.044 Uiso 1 1 calc R . .
H11C H 0.8056 -0.0238 0.6138 0.044 Uiso 1 1 calc R . .
C12 C 0.76750(17) -0.08472(6) 1.0965(5) 0.0428(9) Uani 1 1 d . . .
H12A H 0.8026 -0.0986 1.0904 0.064 Uiso 1 1 calc R . .
H12B H 0.7330 -0.0900 1.0233 0.064 Uiso 1 1 calc R . .
H12C H 0.7502 -0.0843 1.2034 0.064 Uiso 1 1 calc R . .
C13 C 0.99680(12) 0.07462(5) 0.7638(4) 0.0224(6) Uani 1 1 d . . .
C14 C 1.04006(13) 0.09048(5) 0.8591(3) 0.0222(6) Uani 1 1 d . . .
C15 C 1.09386(13) 0.10383(5) 0.7852(4) 0.0251(6) Uani 1 1 d . . .
H15 H 1.1230 0.1147 0.8468 0.030 Uiso 1 1 calc R . .
C16 C 1.10487(14) 0.10128(6) 0.6211(4) 0.0303(7) Uani 1 1 d . . .
C17 C 1.06068(16) 0.08520(6) 0.5313(4) 0.0353(7) Uani 1 1 d . . .
H17 H 1.0679 0.0834 0.4218 0.042 Uiso 1 1 calc R . .
C18 C 1.00643(15) 0.07182(6) 0.5978(4) 0.0317(7) Uani 1 1 d . . .
C19 C 0.9580(2) 0.05524(8) 0.4951(4) 0.0516(10) Uani 1 1 d . . .
H19A H 0.9656 0.0597 0.3845 0.077 Uiso 1 1 calc R . .
H19B H 0.9138 0.0606 0.5238 0.077 Uiso 1 1 calc R . .
H19C H 0.9640 0.0349 0.5119 0.077 Uiso 1 1 calc R . .
C20 C 1.03155(15) 0.09328(6) 1.0367(4) 0.0285(6) Uani 1 1 d . . .
H20A H 0.9865 0.0893 1.0646 0.043 Uiso 1 1 calc R . .
H20B H 1.0427 0.1126 1.0692 0.043 Uiso 1 1 calc R . .
H20C H 1.0600 0.0798 1.0900 0.043 Uiso 1 1 calc R . .
C21 C 1.16428(17) 0.11548(7) 0.5447(4) 0.0442(9) Uani 1 1 d . . .
H21A H 1.1784 0.1315 0.6094 0.066 Uiso 1 1 calc R . .
H21B H 1.1527 0.1223 0.4399 0.066 Uiso 1 1 calc R . .
H21C H 1.1995 0.1017 0.5362 0.066 Uiso 1 1 calc R . .
N1 N 0.86908(11) 0.02710(4) 0.9301(3) 0.0210(5) Uani 1 1 d . . .
N2 N 0.93941(11) 0.06134(4) 0.8350(3) 0.0234(5) Uani 1 1 d . . .
O1 O 0.78245(9) 0.05710(4) 1.0002(3) 0.0286(5) Uani 1 1 d . . .
O2 O 0.87479(10) 0.10151(4) 0.8776(3) 0.0334(5) Uani 1 1 d . . .
S1 S 1.00108(3) 0.021925(12) 1.01459(10) 0.02268(17) 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
C1 N1 1.451(3) . ?
C1 N2 1.455(3) . ?
C1 S1 1.844(3) . ?
C1 H1 0.9800 . ?
C2 O1 1.211(3) . ?
C2 N1 1.359(3) . ?
C2 C3 1.540(4) . ?
C3 O2 1.205(3) . ?
C3 N2 1.355(4) . ?
C4 C9 1.394(4) . ?
C4 C5 1.404(4) . ?
C4 N1 1.443(3) . ?
C5 C6 1.387(4) . ?
C5 C11 1.499(4) . ?
C6 C7 1.394(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(4) . ?
C7 C12 1.515(4) . ?
C8 C9 1.388(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.511(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.393(4) . ?
C13 C18 1.406(4) . ?
C13 N2 1.444(3) . ?
C14 C15 1.397(4) . ?
C14 C20 1.500(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(4) . ?
C16 C21 1.513(4) . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.513(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
S1 S1 2.0307(12) 2_755 ?

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
N1 C1 N2 103.0(2) . . ?
N1 C1 S1 114.29(19) . . ?
N2 C1 S1 107.63(18) . . ?
N1 C1 H1 110.5 . . ?
N2 C1 H1 110.5 . . ?
S1 C1 H1 110.5 . . ?
O1 C2 N1 128.3(3) . . ?
O1 C2 C3 125.9(2) . . ?
N1 C2 C3 105.8(2) . . ?
O2 C3 N2 128.0(3) . . ?
O2 C3 C2 126.3(2) . . ?
N2 C3 C2 105.6(2) . . ?
C9 C4 C5 121.5(2) . . ?
C9 C4 N1 119.8(2) . . ?
C5 C4 N1 118.7(2) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C11 119.5(2) . . ?
C4 C5 C11 122.4(2) . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 118.4(2) . . ?
C8 C7 C12 120.8(3) . . ?
C6 C7 C12 120.9(3) . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C4 118.4(3) . . ?
C8 C9 C10 120.6(3) . . ?
C4 C9 C10 120.9(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 121.7(2) . . ?
C14 C13 N2 119.7(3) . . ?
C18 C13 N2 118.6(2) . . ?
C13 C14 C15 118.1(3) . . ?
C13 C14 C20 122.6(2) . . ?
C15 C14 C20 119.3(2) . . ?
C16 C15 C14 121.5(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 C15 118.4(3) . . ?
C17 C16 C21 121.3(3) . . ?
C15 C16 C21 120.4(3) . . ?
C18 C17 C16 122.5(3) . . ?
C18 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
C17 C18 C13 117.8(3) . . ?
C17 C18 C19 121.1(3) . . ?
C13 C18 C19 121.1(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C2 N1 C4 125.1(2) . . ?
C2 N1 C1 112.5(2) . . ?
C4 N1 C1 122.3(2) . . ?
C3 N2 C13 124.6(2) . . ?
C3 N2 C1 112.7(2) . . ?
C13 N2 C1 122.7(2) . . ?
C1 S1 S1 101.60(9) . 2_755 ?

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
O1 C2 C3 O2 0.3(5) . . . . ?
N1 C2 C3 O2 179.4(3) . . . . ?
O1 C2 C3 N2 -178.8(3) . . . . ?
N1 C2 C3 N2 0.3(3) . . . . ?
C9 C4 C5 C6 0.7(4) . . . . ?
N1 C4 C5 C6 178.7(2) . . . . ?
C9 C4 C5 C11 -179.0(3) . . . . ?
N1 C4 C5 C11 -1.0(4) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C11 C5 C6 C7 179.2(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C5 C6 C7 C12 -179.7(3) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C12 C7 C8 C9 179.8(3) . . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
C7 C8 C9 C10 -179.9(3) . . . . ?
C5 C4 C9 C8 -0.6(4) . . . . ?
N1 C4 C9 C8 -178.6(2) . . . . ?
C5 C4 C9 C10 179.6(3) . . . . ?
N1 C4 C9 C10 1.6(4) . . . . ?
C18 C13 C14 C15 0.3(4) . . . . ?
N2 C13 C14 C15 -177.9(2) . . . . ?
C18 C13 C14 C20 -178.7(3) . . . . ?
N2 C13 C14 C20 3.1(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C20 C14 C15 C16 178.4(3) . . . . ?
C14 C15 C16 C17 0.4(4) . . . . ?
C14 C15 C16 C21 -178.8(3) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C21 C16 C17 C18 179.5(3) . . . . ?
C16 C17 C18 C13 -0.6(5) . . . . ?
C16 C17 C18 C19 178.0(3) . . . . ?
C14 C13 C18 C17 0.4(4) . . . . ?
N2 C13 C18 C17 178.5(3) . . . . ?
C14 C13 C18 C19 -178.3(3) . . . . ?
N2 C13 C18 C19 -0.1(4) . . . . ?
O1 C2 N1 C4 -0.2(5) . . . . ?
C3 C2 N1 C4 -179.3(2) . . . . ?
O1 C2 N1 C1 -177.6(3) . . . . ?
C3 C2 N1 C1 3.4(3) . . . . ?
C9 C4 N1 C2 -70.1(4) . . . . ?
C5 C4 N1 C2 111.9(3) . . . . ?
C9 C4 N1 C1 107.0(3) . . . . ?
C5 C4 N1 C1 -71.0(3) . . . . ?
N2 C1 N1 C2 -5.5(3) . . . . ?
S1 C1 N1 C2 111.0(2) . . . . ?
N2 C1 N1 C4 177.1(2) . . . . ?
S1 C1 N1 C4 -66.5(3) . . . . ?
O2 C3 N2 C13 -0.1(5) . . . . ?
C2 C3 N2 C13 179.0(2) . . . . ?
O2 C3 N2 C1 177.0(3) . . . . ?
C2 C3 N2 C1 -3.9(3) . . . . ?
C14 C13 N2 C3 73.5(4) . . . . ?
C18 C13 N2 C3 -104.8(3) . . . . ?
C14 C13 N2 C1 -103.5(3) . . . . ?
C18 C13 N2 C1 78.3(3) . . . . ?
N1 C1 N2 C3 5.7(3) . . . . ?
S1 C1 N2 C3 -115.4(2) . . . . ?
N1 C1 N2 C13 -177.0(2) . . . . ?
S1 C1 N2 C13 61.9(3) . . . . ?
N1 C1 S1 S1 76.22(18) . . . 2_755 ?
N2 C1 S1 S1 -170.04(16) . . . 2_755 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_18junb_0m
_database_code_depnum_ccdc_archive 'CCDC 1407615'
_audit_update_record             
;
2015-06-18 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H34 B F2 N2 O2 P'
_chemical_formula_sum            'C33 H34 B F2 N2 O2 P'
_chemical_formula_weight         570.40

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_HALL  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.811(5)
_cell_length_b                   14.264(5)
_cell_length_c                   17.760(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 102.367(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2922.6(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5581
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.91

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9752
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24836
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5744
_reflns_number_gt                3672
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP 3'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0415P)²+3.5486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5744
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.0736(3) 0.1244(2) 1.0928(2) 0.0209(8) Uani 1 1 d . . .
C1 C 0.1153(2) 0.2198(2) 0.90086(16) 0.0165(6) Uani 1 1 d . . .
C2 C 0.1209(2) 0.0833(2) 0.97407(16) 0.0179(7) Uani 1 1 d . . .
H2 H 0.1219 0.0204 0.9520 0.021 Uiso 1 1 calc R . .
C3 C -0.0029(2) 0.12408(19) 0.95836(16) 0.0165(6) Uani 1 1 d . . .
H3 H -0.0592 0.0798 0.9293 0.020 Uiso 1 1 calc R . .
C4 C 0.3091(2) 0.1513(2) 0.94601(16) 0.0168(7) Uani 1 1 d . . .
C5 C 0.3617(3) 0.0827(2) 0.90957(17) 0.0222(7) Uani 1 1 d . . .
C6 C 0.4822(3) 0.0835(2) 0.92246(19) 0.0276(8) Uani 1 1 d . . .
H6 H 0.5188 0.0375 0.8992 0.033 Uiso 1 1 calc R . .
C7 C 0.5495(3) 0.1491(2) 0.96792(19) 0.0264(8) Uani 1 1 d . . .
C8 C 0.4942(3) 0.2146(2) 1.00482(18) 0.0232(7) Uani 1 1 d . . .
H8 H 0.5388 0.2587 1.0366 0.028 Uiso 1 1 calc R . .
C9 C 0.3744(2) 0.2171(2) 0.99611(16) 0.0195(7) Uani 1 1 d . . .
C10 C 0.2965(3) 0.0080(2) 0.85821(19) 0.0323(8) Uani 1 1 d . . .
H10A H 0.3123 -0.0520 0.8827 0.048 Uiso 1 1 calc R . .
H10B H 0.3208 0.0077 0.8100 0.048 Uiso 1 1 calc R . .
H10C H 0.2149 0.0207 0.8492 0.048 Uiso 1 1 calc R . .
C11 C 0.6800(3) 0.1502(3) 0.9772(2) 0.0390(10) Uani 1 1 d . . .
H11A H 0.7068 0.0882 0.9693 0.059 Uiso 1 1 calc R . .
H11B H 0.7154 0.1711 1.0282 0.059 Uiso 1 1 calc R . .
H11C H 0.7006 0.1921 0.9400 0.059 Uiso 1 1 calc R . .
C12 C 0.3210(3) 0.2884(2) 1.04041(17) 0.0245(7) Uani 1 1 d . . .
H12A H 0.3772 0.3076 1.0852 0.037 Uiso 1 1 calc R . .
H12B H 0.2554 0.2612 1.0560 0.037 Uiso 1 1 calc R . .
H12C H 0.2965 0.3419 1.0082 0.037 Uiso 1 1 calc R . .
C13 C -0.0903(2) 0.2728(2) 0.89331(16) 0.0170(7) Uani 1 1 d . . .
C14 C -0.0972(2) 0.3468(2) 0.94350(16) 0.0185(7) Uani 1 1 d . . .
C15 C -0.1962(3) 0.4013(2) 0.92844(17) 0.0237(7) Uani 1 1 d . . .
H15 H -0.2026 0.4508 0.9613 0.028 Uiso 1 1 calc R . .
C16 C -0.2867(3) 0.3844(2) 0.86551(18) 0.0263(8) Uani 1 1 d . . .
C17 C -0.2752(2) 0.3113(2) 0.81670(17) 0.0236(7) Uani 1 1 d . . .
H17 H -0.3345 0.3002 0.7739 0.028 Uiso 1 1 calc R . .
C18 C -0.1779(2) 0.2538(2) 0.82950(17) 0.0196(7) Uani 1 1 d . . .
C19 C 0.0008(3) 0.3689(2) 1.01023(17) 0.0240(7) Uani 1 1 d . . .
H19A H -0.0181 0.4237 1.0365 0.036 Uiso 1 1 calc R . .
H19B H 0.0701 0.3803 0.9916 0.036 Uiso 1 1 calc R . .
H19C H 0.0131 0.3168 1.0453 0.036 Uiso 1 1 calc R . .
C20 C -0.3944(3) 0.4447(3) 0.8503(2) 0.0440(10) Uani 1 1 d . . .
H20A H -0.4263 0.4471 0.7958 0.066 Uiso 1 1 calc R . .
H20B H -0.3748 0.5070 0.8692 0.066 Uiso 1 1 calc R . .
H20C H -0.4506 0.4185 0.8761 0.066 Uiso 1 1 calc R . .
C21 C -0.1678(3) 0.1760(2) 0.77430(18) 0.0276(8) Uani 1 1 d . . .
H21A H -0.2380 0.1721 0.7355 0.041 Uiso 1 1 calc R . .
H21B H -0.1550 0.1177 0.8018 0.041 Uiso 1 1 calc R . .
H21C H -0.1038 0.1884 0.7503 0.041 Uiso 1 1 calc R . .
C22 C 0.0543(2) 0.3770(2) 0.79276(17) 0.0192(7) Uani 1 1 d . . .
C23 C 0.0266(3) 0.4609(2) 0.82371(18) 0.0278(8) Uani 1 1 d . . .
H23 H 0.0708 0.4816 0.8705 0.033 Uiso 1 1 calc R . .
C24 C -0.0664(3) 0.5144(2) 0.78572(19) 0.0360(9) Uani 1 1 d . . .
H24 H -0.0854 0.5701 0.8073 0.043 Uiso 1 1 calc R . .
C25 C -0.1301(3) 0.4842(2) 0.71598(19) 0.0328(8) Uani 1 1 d . . .
H25 H -0.1936 0.5190 0.6908 0.039 Uiso 1 1 calc R . .
C26 C -0.1005(3) 0.4030(2) 0.68321(18) 0.0256(8) Uani 1 1 d . . .
H26 H -0.1431 0.3837 0.6355 0.031 Uiso 1 1 calc R . .
C27 C -0.0083(3) 0.3504(2) 0.72078(17) 0.0220(7) Uani 1 1 d . . .
H27 H 0.0125 0.2964 0.6977 0.026 Uiso 1 1 calc R . .
C28 C 0.2228(3) 0.2447(2) 0.77431(18) 0.0266(8) Uani 1 1 d . . .
C29 C 0.1646(3) 0.1675(2) 0.73824(19) 0.0309(8) Uani 1 1 d . . .
H29 H 0.1035 0.1420 0.7569 0.037 Uiso 1 1 calc R . .
C30 C 0.1961(4) 0.1273(3) 0.6743(2) 0.0477(11) Uani 1 1 d . . .
H30 H 0.1562 0.0754 0.6504 0.057 Uiso 1 1 calc R . .
C31 C 0.2864(4) 0.1646(3) 0.6469(3) 0.0628(14) Uani 1 1 d . . .
H31 H 0.3065 0.1388 0.6035 0.075 Uiso 1 1 calc R . .
C32 C 0.3467(4) 0.2392(4) 0.6828(3) 0.0636(14) Uani 1 1 d . . .
H32 H 0.4091 0.2630 0.6646 0.076 Uiso 1 1 calc R . .
C33 C 0.3158(3) 0.2803(3) 0.7466(2) 0.0450(10) Uani 1 1 d . . .
H33 H 0.3572 0.3315 0.7707 0.054 Uiso 1 1 calc R . .
F1 F 0.11630(15) 0.20656(12) 1.13144(10) 0.0285(4) Uani 1 1 d . . .
F2 F 0.04498(15) 0.06251(12) 1.14554(9) 0.0284(4) Uani 1 1 d . . .
N1 N 0.18443(19) 0.15205(16) 0.93511(13) 0.0160(5) Uani 1 1 d . . .
N2 N 0.00755(19) 0.20999(16) 0.91165(13) 0.0162(5) Uani 1 1 d . . .
O1 O 0.16075(17) 0.08212(14) 1.05373(11) 0.0225(5) Uani 1 1 d . . .
O2 O -0.02703(17) 0.14392(14) 1.02991(11) 0.0222(5) Uani 1 1 d . . .
P1 P 0.17801(7) 0.31375(6) 0.84921(5) 0.0198(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F2 1.380(4) . ?
B1 F1 1.397(4) . ?
B1 O2 1.473(4) . ?
B1 O1 1.487(4) . ?
C1 N1 1.326(4) . ?
C1 N2 1.334(3) . ?
C1 P1 1.865(3) . ?
C2 O1 1.392(3) . ?
C2 N1 1.492(3) . ?
C2 C3 1.542(4) . ?
C2 H2 0.9800 . ?
C3 O2 1.390(3) . ?
C3 N2 1.500(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.391(4) . ?
C4 C9 1.404(4) . ?
C4 N1 1.444(3) . ?
C5 C6 1.393(4) . ?
C5 C10 1.503(4) . ?
C6 C7 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(4) . ?
C7 C11 1.515(4) . ?
C8 C9 1.390(4) . ?
C8 H8 0.9300 . ?
C9 C12 1.504(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C18 1.388(4) . ?
C13 C14 1.396(4) . ?
C13 N2 1.442(4) . ?
C14 C15 1.381(4) . ?
C14 C19 1.502(4) . ?
C15 C16 1.392(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(4) . ?
C16 C20 1.512(4) . ?
C17 C18 1.390(4) . ?
C17 H17 0.9300 . ?
C18 C21 1.503(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.385(4) . ?
C22 C27 1.385(4) . ?
C22 P1 1.824(3) . ?
C23 C24 1.388(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.372(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.381(5) . ?
C28 C33 1.392(4) . ?
C28 P1 1.823(3) . ?
C29 C30 1.391(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.371(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.361(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.392(6) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?

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
F2 B1 F1 108.6(3) . . ?
F2 B1 O2 111.1(3) . . ?
F1 B1 O2 111.2(3) . . ?
F2 B1 O1 110.6(3) . . ?
F1 B1 O1 110.9(2) . . ?
O2 B1 O1 104.4(2) . . ?
N1 C1 N2 111.7(2) . . ?
N1 C1 P1 118.6(2) . . ?
N2 C1 P1 129.6(2) . . ?
O1 C2 N1 112.7(2) . . ?
O1 C2 C3 106.8(2) . . ?
N1 C2 C3 102.7(2) . . ?
O1 C2 H2 111.4 . . ?
N1 C2 H2 111.4 . . ?
C3 C2 H2 111.4 . . ?
O2 C3 N2 113.4(2) . . ?
O2 C3 C2 106.5(2) . . ?
N2 C3 C2 102.8(2) . . ?
O2 C3 H3 111.3 . . ?
N2 C3 H3 111.3 . . ?
C2 C3 H3 111.3 . . ?
C5 C4 C9 121.7(3) . . ?
C5 C4 N1 119.1(3) . . ?
C9 C4 N1 119.1(2) . . ?
C4 C5 C6 117.4(3) . . ?
C4 C5 C10 124.0(3) . . ?
C6 C5 C10 118.6(3) . . ?
C7 C6 C5 123.0(3) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C8 117.8(3) . . ?
C6 C7 C11 121.3(3) . . ?
C8 C7 C11 120.9(3) . . ?
C7 C8 C9 122.5(3) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C8 C9 C4 117.4(3) . . ?
C8 C9 C12 119.3(3) . . ?
C4 C9 C12 123.3(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.2(3) . . ?
C18 C13 N2 119.0(3) . . ?
C14 C13 N2 118.6(3) . . ?
C15 C14 C13 117.7(3) . . ?
C15 C14 C19 120.8(3) . . ?
C13 C14 C19 121.4(3) . . ?
C14 C15 C16 122.0(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 118.2(3) . . ?
C17 C16 C20 120.6(3) . . ?
C15 C16 C20 121.1(3) . . ?
C16 C17 C18 122.1(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C17 117.7(3) . . ?
C13 C18 C21 121.8(3) . . ?
C17 C18 C21 120.5(3) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 118.6(3) . . ?
C23 C22 P1 116.0(2) . . ?
C27 C22 P1 125.3(2) . . ?
C22 C23 C24 120.8(3) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 119.3(3) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 120.1(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 120.7(3) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C29 C28 C33 118.6(3) . . ?
C29 C28 P1 125.2(2) . . ?
C33 C28 P1 115.8(3) . . ?
C28 C29 C30 120.9(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C31 C30 C29 119.6(4) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C32 C31 C30 120.4(4) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C33 120.6(4) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C28 C33 C32 119.9(4) . . ?
C28 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C1 N1 C4 125.2(2) . . ?
C1 N1 C2 111.7(2) . . ?
C4 N1 C2 122.2(2) . . ?
C1 N2 C13 130.1(2) . . ?
C1 N2 C3 111.0(2) . . ?
C13 N2 C3 118.4(2) . . ?
C2 O1 B1 110.6(2) . . ?
C3 O2 B1 111.4(2) . . ?
C28 P1 C22 100.95(14) . . ?
C28 P1 C1 100.29(14) . . ?
C22 P1 C1 105.63(13) . . ?

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
O1 C2 C3 O2 0.0(3) . . . . ?
N1 C2 C3 O2 -118.8(2) . . . . ?
O1 C2 C3 N2 119.4(2) . . . . ?
N1 C2 C3 N2 0.7(3) . . . . ?
C9 C4 C5 C6 -2.2(4) . . . . ?
N1 C4 C5 C6 -179.0(3) . . . . ?
C9 C4 C5 C10 177.2(3) . . . . ?
N1 C4 C5 C10 0.4(4) . . . . ?
C4 C5 C6 C7 -1.0(5) . . . . ?
C10 C5 C6 C7 179.5(3) . . . . ?
C5 C6 C7 C8 2.7(5) . . . . ?
C5 C6 C7 C11 -176.9(3) . . . . ?
C6 C7 C8 C9 -1.3(4) . . . . ?
C11 C7 C8 C9 178.4(3) . . . . ?
C7 C8 C9 C4 -1.8(4) . . . . ?
C7 C8 C9 C12 177.8(3) . . . . ?
C5 C4 C9 C8 3.5(4) . . . . ?
N1 C4 C9 C8 -179.6(2) . . . . ?
C5 C4 C9 C12 -176.0(3) . . . . ?
N1 C4 C9 C12 0.8(4) . . . . ?
C18 C13 C14 C15 0.8(4) . . . . ?
N2 C13 C14 C15 -174.6(2) . . . . ?
C18 C13 C14 C19 -177.2(3) . . . . ?
N2 C13 C14 C19 7.3(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C19 C14 C15 C16 177.8(3) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C14 C15 C16 C20 179.8(3) . . . . ?
C15 C16 C17 C18 1.3(4) . . . . ?
C20 C16 C17 C18 -179.3(3) . . . . ?
C14 C13 C18 C17 -0.3(4) . . . . ?
N2 C13 C18 C17 175.1(2) . . . . ?
C14 C13 C18 C21 177.8(3) . . . . ?
N2 C13 C18 C21 -6.7(4) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C16 C17 C18 C21 -179.0(3) . . . . ?
C27 C22 C23 C24 4.0(5) . . . . ?
P1 C22 C23 C24 -179.6(3) . . . . ?
C22 C23 C24 C25 -1.2(5) . . . . ?
C23 C24 C25 C26 -1.5(5) . . . . ?
C24 C25 C26 C27 1.3(5) . . . . ?
C25 C26 C27 C22 1.6(5) . . . . ?
C23 C22 C27 C26 -4.2(4) . . . . ?
P1 C22 C27 C26 179.8(2) . . . . ?
C33 C28 C29 C30 -1.5(5) . . . . ?
P1 C28 C29 C30 170.8(3) . . . . ?
C28 C29 C30 C31 0.2(5) . . . . ?
C29 C30 C31 C32 1.5(6) . . . . ?
C30 C31 C32 C33 -1.7(7) . . . . ?
C29 C28 C33 C32 1.3(5) . . . . ?
P1 C28 C33 C32 -171.8(3) . . . . ?
C31 C32 C33 C28 0.3(6) . . . . ?
N2 C1 N1 C4 -168.4(3) . . . . ?
P1 C1 N1 C4 9.7(4) . . . . ?
N2 C1 N1 C2 1.4(3) . . . . ?
P1 C1 N1 C2 179.58(19) . . . . ?
C5 C4 N1 C1 -115.9(3) . . . . ?
C9 C4 N1 C1 67.2(4) . . . . ?
C5 C4 N1 C2 75.3(4) . . . . ?
C9 C4 N1 C2 -101.6(3) . . . . ?
O1 C2 N1 C1 -115.8(3) . . . . ?
C3 C2 N1 C1 -1.3(3) . . . . ?
O1 C2 N1 C4 54.4(3) . . . . ?
C3 C2 N1 C4 168.9(2) . . . . ?
N1 C1 N2 C13 171.3(3) . . . . ?
P1 C1 N2 C13 -6.6(5) . . . . ?
N1 C1 N2 C3 -0.9(3) . . . . ?
P1 C1 N2 C3 -178.8(2) . . . . ?
C18 C13 N2 C1 103.7(3) . . . . ?
C14 C13 N2 C1 -80.7(4) . . . . ?
C18 C13 N2 C3 -84.5(3) . . . . ?
C14 C13 N2 C3 91.0(3) . . . . ?
O2 C3 N2 C1 114.6(3) . . . . ?
C2 C3 N2 C1 0.1(3) . . . . ?
O2 C3 N2 C13 -58.7(3) . . . . ?
C2 C3 N2 C13 -173.2(2) . . . . ?
N1 C2 O1 B1 109.0(3) . . . . ?
C3 C2 O1 B1 -3.0(3) . . . . ?
F2 B1 O1 C2 124.4(3) . . . . ?
F1 B1 O1 C2 -115.1(3) . . . . ?
O2 B1 O1 C2 4.7(3) . . . . ?
N2 C3 O2 B1 -109.2(3) . . . . ?
C2 C3 O2 B1 3.1(3) . . . . ?
F2 B1 O2 C3 -124.1(3) . . . . ?
F1 B1 O2 C3 114.8(3) . . . . ?
O1 B1 O2 C3 -4.8(3) . . . . ?
C29 C28 P1 C22 -73.3(3) . . . . ?
C33 C28 P1 C22 99.3(3) . . . . ?
C29 C28 P1 C1 35.0(3) . . . . ?
C33 C28 P1 C1 -152.4(3) . . . . ?
C23 C22 P1 C28 -155.6(2) . . . . ?
C27 C22 P1 C28 20.5(3) . . . . ?
C23 C22 P1 C1 100.3(2) . . . . ?
C27 C22 P1 C1 -83.6(3) . . . . ?
N1 C1 P1 C28 63.1(2) . . . . ?
N2 C1 P1 C28 -119.1(3) . . . . ?
N1 C1 P1 C22 167.6(2) . . . . ?
N2 C1 P1 C22 -14.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.065
