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

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

data_100509a_0m
_database_code_depnum_ccdc_archive 'CCDC 1423134'
_audit_update_record             
;
2015-09-08 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H32 N3 O4 S'
_chemical_formula_weight         326.48

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/n  '

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

_cell_length_a                   15.4997(3)
_cell_length_b                   7.5991(2)
_cell_length_c                   16.5240(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.066(2)
_cell_angle_gamma                90.00
_cell_volume                     1828.12(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9332
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            9924
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         27.80
_reflns_number_total             4267
_reflns_number_gt                2294
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0708P)²+0.1281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4267
_refine_ls_number_parameters     191
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
S1 S 0.93451(4) 0.35391(8) 0.65597(4) 0.0638(2) Uani 1 1 d . . .
O1 O 0.94601(13) 0.5298(2) 0.69089(13) 0.0835(6) Uani 1 1 d . . .
O1W O 0.99089(19) 0.8752(3) 0.63368(13) 0.1253(9) Uani 1 1 d D . .
H1WA H 0.9812 0.7834 0.6587 0.188 Uiso 1 1 d RD . .
H1WB H 0.9952 0.9616 0.6675 0.188 Uiso 1 1 d RD . .
N1 N 0.94563(16) 0.2130(3) 0.51295(14) 0.0866(7) Uani 1 1 d . . .
H1A H 0.9209 0.1281 0.5325 0.130 Uiso 1 1 d R . .
H1B H 0.9618 0.1966 0.4636 0.130 Uiso 1 1 d R . .
C1 C 0.95955(14) 0.3635(3) 0.55765(14) 0.0509(5) Uani 1 1 d . . .
O2 O 0.84247(12) 0.2885(3) 0.63204(15) 0.1039(7) Uani 1 1 d . . .
N2 N 0.98953(12) 0.5079(2) 0.53865(11) 0.0534(5) Uani 1 1 d . . .
C2 C 0.7497(2) 0.7433(3) 0.82496(19) 0.0830(8) Uani 1 1 d . . .
H2A H 0.6955 0.6690 0.8061 0.100 Uiso 1 1 calc R . .
H2B H 0.7441 0.8195 0.8700 0.100 Uiso 1 1 calc R . .
N3 N 0.7500 0.8569(3) 0.7500 0.0660(8) Uani 1 2 d S . .
O3 O 1.00222(12) 0.2309(2) 0.70845(11) 0.0761(5) Uani 1 1 d . . .
C3 C 0.8344(3) 0.6253(4) 0.8639(3) 0.1182(13) Uani 1 1 d . . .
H3A H 0.8311 0.5265 0.8258 0.142 Uiso 1 1 calc R . .
H3B H 0.8895 0.6917 0.8693 0.142 Uiso 1 1 calc R . .
N4 N 0.2500 0.4796(3) 0.7500 0.0599(7) Uani 1 2 d S . .
C4 C 0.8394(3) 0.5584(5) 0.9507(2) 0.1241(13) Uani 1 1 d . . .
H4A H 0.8932 0.4867 0.9743 0.186 Uiso 1 1 calc R . .
H4B H 0.7857 0.4895 0.9451 0.186 Uiso 1 1 calc R . .
H4C H 0.8425 0.6562 0.9884 0.186 Uiso 1 1 calc R . .
C5 C 0.66420(17) 0.9708(3) 0.72545(19) 0.0752(8) Uani 1 1 d . . .
H5A H 0.6117 0.8948 0.7176 0.090 Uiso 1 1 calc R . .
H5B H 0.6691 1.0487 0.7733 0.090 Uiso 1 1 calc R . .
C6 C 0.6453(2) 1.0820(4) 0.6449(2) 0.1078(12) Uani 1 1 d . . .
H6A H 0.6882 1.1796 0.6576 0.129 Uiso 1 1 calc R . .
H6B H 0.6561 1.0112 0.6004 0.129 Uiso 1 1 calc R . .
C7 C 0.5513(2) 1.1519(5) 0.6115(2) 0.1160(11) Uani 1 1 d . . .
H7A H 0.5435 1.2195 0.5604 0.174 Uiso 1 1 calc R . .
H7B H 0.5407 1.2258 0.6543 0.174 Uiso 1 1 calc R . .
H7C H 0.5083 1.0562 0.5980 0.174 Uiso 1 1 calc R . .
C8 C 0.32353(17) 0.5921(3) 0.73422(19) 0.0736(7) Uani 1 1 d . . .
H8A H 0.3489 0.6699 0.7832 0.088 Uiso 1 1 calc R . .
H8B H 0.3727 0.5153 0.7321 0.088 Uiso 1 1 calc R . .
C9 C 0.2930(2) 0.7030(4) 0.6532(2) 0.0996(10) Uani 1 1 d . . .
H9A H 0.2609 0.6296 0.6040 0.120 Uiso 1 1 calc R . .
H9B H 0.2510 0.7935 0.6581 0.120 Uiso 1 1 calc R . .
C10 C 0.3751(2) 0.7881(4) 0.6391(2) 0.1147(11) Uani 1 1 d . . .
H10A H 0.3549 0.8552 0.5867 0.172 Uiso 1 1 calc R . .
H10B H 0.4171 0.6984 0.6351 0.172 Uiso 1 1 calc R . .
H10C H 0.4054 0.8644 0.6867 0.172 Uiso 1 1 calc R . .
C11 C 0.20166(15) 0.3668(3) 0.67221(16) 0.0653(6) Uani 1 1 d . . .
H11A H 0.1560 0.2960 0.6853 0.078 Uiso 1 1 calc R . .
H11B H 0.1691 0.4440 0.6248 0.078 Uiso 1 1 calc R . .
C12 C 0.26146(18) 0.2453(3) 0.64197(19) 0.0818(8) Uani 1 1 d . . .
H12A H 0.2903 0.1588 0.6862 0.098 Uiso 1 1 calc R . .
H12B H 0.3094 0.3121 0.6307 0.098 Uiso 1 1 calc R . .
C13 C 0.2021(2) 0.1537(4) 0.5604(2) 0.1041(10) Uani 1 1 d . . .
H13A H 0.2393 0.0759 0.5406 0.156 Uiso 1 1 calc R . .
H13B H 0.1742 0.2400 0.5168 0.156 Uiso 1 1 calc R . .
H13C H 0.1550 0.0874 0.5722 0.156 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4324(18) . ?
S1 O1 1.4427(18) . ?
S1 O3 1.4500(17) . ?
S1 C1 1.797(2) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8501 . ?
N1 C1 1.339(3) . ?
N1 H1A 0.8674 . ?
N1 H1B 0.9396 . ?
C1 N2 1.272(2) . ?
N2 N2 1.427(3) 3_766 ?
C2 N3 1.511(3) . ?
C2 C3 1.537(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N3 C2 1.511(3) 2_656 ?
N3 C5 1.521(3) 2_656 ?
N3 C5 1.521(3) . ?
C3 C4 1.498(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N4 C11 1.512(3) . ?
N4 C11 1.512(3) 2_556 ?
N4 C8 1.517(3) . ?
N4 C8 1.517(3) 2_556 ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.518(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.468(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.515(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.514(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.510(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.515(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
O2 S1 O1 114.01(12) . . ?
O2 S1 O3 112.91(11) . . ?
O1 S1 O3 113.16(12) . . ?
O2 S1 C1 105.55(12) . . ?
O1 S1 C1 106.78(10) . . ?
O3 S1 C1 103.32(9) . . ?
H1WA O1W H1WB 107.5 . . ?
C1 N1 H1A 116.0 . . ?
C1 N1 H1B 123.5 . . ?
H1A N1 H1B 120.6 . . ?
N2 C1 N1 127.2(2) . . ?
N2 C1 S1 117.95(17) . . ?
N1 C1 S1 114.86(15) . . ?
C1 N2 N2 111.3(2) . 3_766 ?
N3 C2 C3 115.7(2) . . ?
N3 C2 H2A 108.3 . . ?
C3 C2 H2A 108.3 . . ?
N3 C2 H2B 108.3 . . ?
C3 C2 H2B 108.3 . . ?
H2A C2 H2B 107.4 . . ?
C2 N3 C2 110.4(3) 2_656 . ?
C2 N3 C5 107.18(14) 2_656 2_656 ?
C2 N3 C5 110.79(16) . 2_656 ?
C2 N3 C5 110.79(16) 2_656 . ?
C2 N3 C5 107.18(14) . . ?
C5 N3 C5 110.6(2) 2_656 . ?
C4 C3 C2 110.8(3) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C11 N4 C11 111.0(2) . 2_556 ?
C11 N4 C8 110.83(15) . . ?
C11 N4 C8 106.45(14) 2_556 . ?
C11 N4 C8 106.45(14) . 2_556 ?
C11 N4 C8 110.83(15) 2_556 2_556 ?
C8 N4 C8 111.4(3) . 2_556 ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N3 116.03(19) . . ?
C6 C5 H5A 108.3 . . ?
N3 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
N3 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C5 113.5(3) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N4 116.1(2) . . ?
C9 C8 H8A 108.3 . . ?
N4 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
N4 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 110.4(3) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
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 . . ?
C12 C11 N4 116.53(18) . . ?
C12 C11 H11A 108.2 . . ?
N4 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
N4 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
C11 C12 C13 108.7(2) . . ?
C11 C12 H12A 110.0 . . ?
C13 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
C13 C12 H12B 110.0 . . ?
H12A C12 H12B 108.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O1 0.85 2.12 2.952(3) 166.3 .
O1W H1WB O3 0.85 2.15 2.952(3) 158.1 1_565
N1 H1A O1W 0.87 2.53 3.178(3) 131.7 1_545
N1 H1B O1W 0.94 2.06 2.987(3) 170.4 3_766

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.80
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_lyp-1
_database_code_depnum_ccdc_archive 'CCDC 1426125'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H27 N'
_chemical_formula_weight         509.62

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   14.249(5)
_cell_length_b                   11.262(5)
_cell_length_c                   17.886(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.314(11)
_cell_angle_gamma                90.00
_cell_volume                     2781.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.336
_exptl_crystal_size_min          0.058
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_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            26273
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_sigmaI/netI    0.1156
_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       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.49
_reflns_number_total             6340
_reflns_number_gt                2294
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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)+(0.0527P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6340
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2170
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1546
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_restrained_S_all      0.944
_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
C9 C 0.0333(4) 0.5958(5) 0.2981(4) 0.1292(19) Uani 1 1 d . . .
C10 C 0.0978(4) 0.6135(4) 0.3668(4) 0.1037(15) Uani 1 1 d . . .
C11 C 0.1955(3) 0.5899(3) 0.3767(2) 0.0772(11) Uani 1 1 d . . .
C6 C 0.2295(3) 0.5464(3) 0.31585(18) 0.0650(9) Uani 1 1 d . . .
C5 C 0.3338(2) 0.5246(3) 0.32377(16) 0.0539(8) Uani 1 1 d . . .
C12 C 0.3938(3) 0.4729(3) 0.38864(17) 0.0579(9) Uani 1 1 d . . .
C13 C 0.4901(3) 0.4523(3) 0.39318(16) 0.0555(8) Uani 1 1 d . . .
C14 C 0.5322(2) 0.4841(2) 0.33353(14) 0.0478(7) Uani 1 1 d . . .
C15 C 0.6344(2) 0.4550(2) 0.33771(15) 0.0492(7) Uani 1 1 d . . .
C20 C 0.7080(3) 0.4917(3) 0.39933(19) 0.0664(10) Uani 1 1 d . . .
C19 C 0.8031(3) 0.4655(4) 0.4023(3) 0.0835(12) Uani 1 1 d . . .
C18 C 0.8266(3) 0.4009(4) 0.3442(3) 0.0870(12) Uani 1 1 d . . .
C17 C 0.7546(3) 0.3612(4) 0.2837(2) 0.0777(11) Uani 1 1 d . . .
C16 C 0.6591(3) 0.3887(3) 0.27996(17) 0.0623(9) Uani 1 1 d . . .
C3 C 0.4734(2) 0.5407(2) 0.26893(13) 0.0468(7) Uani 1 1 d . . .
C4 C 0.3760(2) 0.5587(3) 0.26473(16) 0.0526(8) Uani 1 1 d . . .
C7 C 0.1637(3) 0.5270(5) 0.2461(2) 0.1042(15) Uani 1 1 d . . .
C8 C 0.0659(4) 0.5533(6) 0.2372(4) 0.139(2) Uani 1 1 d . . .
C2 C 0.5128(2) 0.5925(2) 0.20605(13) 0.0450(7) Uani 1 1 d . . .
C1 C 0.5934(2) 0.6720(3) 0.23204(14) 0.0566(8) Uani 1 1 d . . .
C21 C 0.4700(2) 0.5782(2) 0.13097(14) 0.0440(7) Uani 1 1 d . . .
C37 C 0.1238(3) 0.5889(3) -0.0313(2) 0.0773(11) Uani 1 1 d . . .
C36 C 0.1759(3) 0.6413(3) 0.0359(2) 0.0711(10) Uani 1 1 d . . .
C35 C 0.2734(2) 0.6686(3) 0.04551(17) 0.0545(8) Uani 1 1 d . . .
C34 C 0.3204(2) 0.6391(2) -0.01119(14) 0.0482(7) Uani 1 1 d . . .
C33 C 0.4252(2) 0.6609(2) -0.00293(13) 0.0430(7) Uani 1 1 d . . .
C22 C 0.4962(2) 0.6328(2) 0.06467(13) 0.0413(7) Uani 1 1 d . . .
C23 C 0.5928(2) 0.6530(2) 0.06632(15) 0.0462(7) Uani 1 1 d . . .
C24 C 0.6239(2) 0.6990(2) 0.00448(14) 0.0462(7) Uani 1 1 d . . .
C25 C 0.7279(2) 0.7191(2) 0.00917(16) 0.0473(7) Uani 1 1 d . . .
C26 C 0.7890(2) 0.7566(3) 0.0786(2) 0.0643(9) Uani 1 1 d . . .
C27 C 0.8858(3) 0.7782(3) 0.0838(2) 0.0819(11) Uani 1 1 d . . .
C28 C 0.9232(3) 0.7616(4) 0.0203(3) 0.0888(12) Uani 1 1 d . . .
C29 C 0.8626(3) 0.7232(4) -0.0487(3) 0.0834(11) Uani 1 1 d . . .
C30 C 0.7651(3) 0.7033(3) -0.0528(2) 0.0680(10) Uani 1 1 d . . .
C31 C 0.5520(2) 0.7277(3) -0.06138(16) 0.0540(8) Uani 1 1 d . . .
C32 C 0.4552(2) 0.7092(2) -0.06469(15) 0.0501(8) Uani 1 1 d . . .
C39 C 0.2654(2) 0.5875(3) -0.07904(17) 0.0557(8) Uani 1 1 d . . .
C38 C 0.1694(3) 0.5631(3) -0.0887(2) 0.0724(10) Uani 1 1 d . . .
H9 H -0.045(4) 0.614(4) 0.285(2) 0.160(18) Uiso 1 1 d . . .
H10 H 0.075(3) 0.645(3) 0.411(2) 0.125(15) Uiso 1 1 d . . .
H11 H 0.250(3) 0.604(3) 0.424(2) 0.120(15) Uiso 1 1 d . . .
H12 H 0.3666(19) 0.451(2) 0.4326(16) 0.064(9) Uiso 1 1 d . . .
H13 H 0.5315(18) 0.407(2) 0.4375(14) 0.062(8) Uiso 1 1 d . . .
H20 H 0.691(2) 0.538(3) 0.4388(16) 0.069(10) Uiso 1 1 d . . .
H19 H 0.855(3) 0.489(3) 0.4464(19) 0.097(12) Uiso 1 1 d . . .
H18 H 0.894(3) 0.387(3) 0.3465(19) 0.107(14) Uiso 1 1 d . . .
H17 H 0.767(2) 0.311(3) 0.2433(18) 0.101(13) Uiso 1 1 d . . .
H16 H 0.602(2) 0.359(3) 0.2336(17) 0.091(11) Uiso 1 1 d . . .
H4 H 0.335(2) 0.603(2) 0.2178(15) 0.074(9) Uiso 1 1 d . . .
H7 H 0.192(3) 0.500(4) 0.199(2) 0.142(16) Uiso 1 1 d . . .
H8 H 0.020(4) 0.532(5) 0.187(4) 0.23(3) Uiso 1 1 d . . .
H21 H 0.4136(17) 0.527(2) 0.1185(12) 0.041(7) Uiso 1 1 d . . .
H37 H 0.054(2) 0.572(3) -0.0367(15) 0.077(10) Uiso 1 1 d . . .
H36 H 0.149(2) 0.665(3) 0.0750(16) 0.078(11) Uiso 1 1 d . . .
H35 H 0.315(2) 0.711(3) 0.0940(16) 0.079(9) Uiso 1 1 d . . .
H23 H 0.6396(17) 0.629(2) 0.1127(13) 0.049(7) Uiso 1 1 d . . .
H26 H 0.760(2) 0.767(3) 0.1252(16) 0.080(10) Uiso 1 1 d . . .
H27 H 0.929(2) 0.802(3) 0.1390(19) 0.103(12) Uiso 1 1 d . . .
H28 H 0.999(3) 0.775(3) 0.0168(18) 0.119(13) Uiso 1 1 d . . .
H29 H 0.890(3) 0.707(4) -0.102(2) 0.152(16) Uiso 1 1 d . . .
H30 H 0.7225(19) 0.676(2) -0.0985(14) 0.054(9) Uiso 1 1 d . . .
H31 H 0.5698(18) 0.763(2) -0.1066(15) 0.065(8) Uiso 1 1 d . . .
H32 H 0.4017(17) 0.732(2) -0.1132(13) 0.057(8) Uiso 1 1 d . . .
H39 H 0.2971(18) 0.570(2) -0.1228(14) 0.057(8) Uiso 1 1 d . . .
H38 H 0.132(3) 0.528(3) -0.1363(19) 0.106(13) Uiso 1 1 d . . .
N N 0.6554(2) 0.7358(3) 0.25504(14) 0.0855(10) 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
C9 C10 1.355(6) . ?
C9 C8 1.373(7) . ?
C10 C11 1.384(6) . ?
C11 C6 1.387(5) . ?
C6 C7 1.380(4) . ?
C6 C5 1.478(4) . ?
C5 C12 1.387(4) . ?
C5 C4 1.392(4) . ?
C12 C13 1.374(4) . ?
C13 C14 1.394(4) . ?
C14 C3 1.402(3) . ?
C14 C15 1.476(4) . ?
C15 C20 1.383(4) . ?
C15 C16 1.388(4) . ?
C20 C19 1.375(5) . ?
C19 C18 1.376(5) . ?
C18 C17 1.369(5) . ?
C17 C16 1.381(5) . ?
C3 C4 1.386(4) . ?
C3 C2 1.494(4) . ?
C7 C8 1.394(6) . ?
C2 C21 1.340(3) . ?
C2 C1 1.440(4) . ?
C1 N 1.134(3) . ?
C21 C22 1.464(3) . ?
C37 C38 1.374(5) . ?
C37 C36 1.379(5) . ?
C36 C35 1.392(4) . ?
C35 C34 1.387(4) . ?
C34 C39 1.398(4) . ?
C34 C33 1.485(4) . ?
C33 C32 1.390(4) . ?
C33 C22 1.407(3) . ?
C22 C23 1.388(4) . ?
C23 C24 1.389(4) . ?
C24 C31 1.395(3) . ?
C24 C25 1.481(4) . ?
C25 C30 1.354(4) . ?
C25 C26 1.394(4) . ?
C26 C27 1.381(4) . ?
C27 C28 1.382(5) . ?
C28 C29 1.388(5) . ?
C29 C30 1.391(5) . ?
C31 C32 1.381(4) . ?
C39 C38 1.363(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C9 C8 119.0(6) . . ?
C9 C10 C11 121.5(5) . . ?
C10 C11 C6 120.2(5) . . ?
C7 C6 C11 118.3(4) . . ?
C7 C6 C5 120.2(3) . . ?
C11 C6 C5 121.5(3) . . ?
C12 C5 C4 117.3(3) . . ?
C12 C5 C6 123.2(3) . . ?
C4 C5 C6 119.6(3) . . ?
C13 C12 C5 121.3(3) . . ?
C12 C13 C14 121.6(3) . . ?
C13 C14 C3 117.7(3) . . ?
C13 C14 C15 120.7(3) . . ?
C3 C14 C15 121.6(3) . . ?
C20 C15 C16 118.2(3) . . ?
C20 C15 C14 121.2(3) . . ?
C16 C15 C14 120.6(3) . . ?
C19 C20 C15 120.8(4) . . ?
C20 C19 C18 120.4(4) . . ?
C17 C18 C19 119.6(4) . . ?
C18 C17 C16 120.2(4) . . ?
C17 C16 C15 120.8(4) . . ?
C4 C3 C14 119.9(3) . . ?
C4 C3 C2 117.4(2) . . ?
C14 C3 C2 122.6(3) . . ?
C3 C4 C5 122.2(3) . . ?
C6 C7 C8 120.5(5) . . ?
C9 C8 C7 120.5(6) . . ?
C21 C2 C1 121.8(3) . . ?
C21 C2 C3 123.1(3) . . ?
C1 C2 C3 114.7(2) . . ?
N C1 C2 177.2(3) . . ?
C2 C21 C22 128.2(3) . . ?
C38 C37 C36 119.3(4) . . ?
C37 C36 C35 120.5(4) . . ?
C34 C35 C36 120.3(3) . . ?
C35 C34 C39 117.8(3) . . ?
C35 C34 C33 122.9(3) . . ?
C39 C34 C33 119.3(3) . . ?
C32 C33 C22 118.3(3) . . ?
C32 C33 C34 119.0(2) . . ?
C22 C33 C34 122.7(2) . . ?
C23 C22 C33 118.7(2) . . ?
C23 C22 C21 120.1(2) . . ?
C33 C22 C21 121.2(3) . . ?
C22 C23 C24 123.6(3) . . ?
C23 C24 C31 116.5(3) . . ?
C23 C24 C25 121.6(3) . . ?
C31 C24 C25 121.9(3) . . ?
C30 C25 C26 118.9(3) . . ?
C30 C25 C24 121.5(3) . . ?
C26 C25 C24 119.5(3) . . ?
C27 C26 C25 120.5(4) . . ?
C26 C27 C28 120.2(4) . . ?
C27 C28 C29 119.4(4) . . ?
C28 C29 C30 119.4(4) . . ?
C25 C30 C29 121.6(4) . . ?
C32 C31 C24 121.2(3) . . ?
C31 C32 C33 121.7(3) . . ?
C38 C39 C34 121.6(3) . . ?
C39 C38 C37 120.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.034
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
