# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1492145'
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT220_4a                  
;
PROBLEM: Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        3.6 Ratio
RESPONSE: No omission
;
_vrf_PLAT242_4a                  
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         S1 Check
RESPONSE: no oversight
;
# Added during the CSD deposition process: Monday 11 July 2016 08:09 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 Br N O5 S'
_chemical_formula_weight         510.35

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'
Br Br -0.2901 2.4595 '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                   10.4343(4)
_cell_length_b                   14.6016(5)
_cell_length_c                   13.8826(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.748(2)
_cell_angle_gamma                90.00
_cell_volume                     2112.69(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5467
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.7

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    2.083
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS Bruker, 2007)'

_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  'Bruker SMART APEX CCD diffractometer'
_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            29923
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.73
_reflns_number_total             5467
_reflns_number_gt                2721
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       'SMART, SAINT'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1999)'
_computing_publication_material  'SHELXTLCIF-97 (Sheldrick, 2008)'

_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)+(0.0674P)²+0.3963P] 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         5467
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1559
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.3823(6) 0.2158(4) 0.8065(6) 0.129(3) Uani 1 1 d . . .
H1A H 0.3740 0.2809 0.7987 0.193 Uiso 1 1 calc R . .
H1B H 0.3903 0.2011 0.8739 0.193 Uiso 1 1 calc R . .
H1C H 0.3078 0.1861 0.7779 0.193 Uiso 1 1 calc R . .
C2 C 0.1944(5) 0.1246(4) 0.3503(4) 0.0848(15) Uani 1 1 d . . .
H2A H 0.1775 0.0863 0.2940 0.102 Uiso 1 1 calc R . .
H2B H 0.1933 0.1880 0.3297 0.102 Uiso 1 1 calc R . .
C3 C 0.7729(4) -0.3332(3) 0.9844(3) 0.0684(13) Uani 1 1 d . . .
H3A H 0.8471 -0.3695 0.9692 0.082 Uiso 1 1 calc R . .
H3B H 0.7415 -0.3553 1.0448 0.082 Uiso 1 1 calc R . .
C4 C 0.8617(4) 0.1903(3) 1.0060(3) 0.0567(11) Uani 1 1 d . . .
H4 H 0.9192 0.2246 1.0446 0.068 Uiso 1 1 calc R . .
C5 C 0.7438(4) 0.1695(3) 1.0378(3) 0.0570(11) Uani 1 1 d . . .
H5 H 0.7201 0.1908 1.0976 0.068 Uiso 1 1 calc R . .
C6 C 0.3794(3) 0.0586(2) 0.5593(3) 0.0455(9) Uani 1 1 d . . .
H6 H 0.4667 0.0589 0.5486 0.055 Uiso 1 1 calc R . .
C7 C 0.2935(4) 0.0809(2) 0.4882(3) 0.0475(9) Uani 1 1 d . . .
C9 C 0.1640(4) 0.0841(3) 0.5020(3) 0.0496(10) Uani 1 1 d . . .
C11 C 0.8955(4) 0.1608(3) 0.9171(3) 0.0584(11) Uani 1 1 d . . .
H11 H 0.9757 0.1758 0.8952 0.070 Uiso 1 1 calc R . .
C12 C 0.8122(3) 0.1089(3) 0.8596(3) 0.0478(9) Uani 1 1 d . . .
H12 H 0.8354 0.0892 0.7991 0.057 Uiso 1 1 calc R . .
C13 C 0.7184(3) -0.1010(3) 0.9220(3) 0.0472(9) Uani 1 1 d . . .
H13 H 0.7746 -0.0613 0.9551 0.057 Uiso 1 1 calc R . .
C14 C 0.6591(4) 0.1169(3) 0.9820(3) 0.0504(9) Uani 1 1 d . . .
H14 H 0.5792 0.1019 1.0043 0.060 Uiso 1 1 calc R . .
C15 C 0.5369(3) -0.1289(2) 0.8078(2) 0.0358(8) Uani 1 1 d . . .
C16 C 0.1156(4) 0.0624(3) 0.5876(3) 0.0521(10) Uani 1 1 d . . .
H16 H 0.0279 0.0638 0.5968 0.062 Uiso 1 1 calc R . .
C17 C 0.5485(3) -0.2240(2) 0.8225(2) 0.0424(8) Uani 1 1 d . . .
H17 H 0.4933 -0.2652 0.7906 0.051 Uiso 1 1 calc R . .
C18 C 0.6938(3) 0.0869(2) 0.8932(2) 0.0392(8) Uani 1 1 d . . .
C19 C 0.6437(3) -0.2528(2) 0.8851(3) 0.0442(9) Uani 1 1 d . . .
C20 C 0.7253(3) -0.1920(2) 0.9344(3) 0.0427(9) Uani 1 1 d . . .
C21 C 0.3352(3) 0.0347(2) 0.6506(3) 0.0400(8) Uani 1 1 d . . .
C22 C 0.4354(3) -0.0964(2) 0.7412(2) 0.0418(8) Uani 1 1 d . . .
C23 C 0.4298(3) 0.0015(2) 0.7268(2) 0.0395(8) Uani 1 1 d . . .
C24 C 0.6205(3) -0.0679(2) 0.8554(2) 0.0377(8) Uani 1 1 d . . .
C25 C 0.2048(3) 0.0374(3) 0.6620(3) 0.0450(9) Uani 1 1 d . . .
C26 C 0.5157(3) 0.0585(2) 0.7733(2) 0.0389(8) Uani 1 1 d . . .
N1 N 0.6092(3) 0.02581(19) 0.8375(2) 0.0404(7) Uani 1 1 d . . .
O1 O 0.3157(3) 0.1027(2) 0.3940(2) 0.0728(9) Uani 1 1 d . . .
O2 O 0.0986(3) 0.1100(2) 0.4179(2) 0.0720(9) Uani 1 1 d . . .
O3 O 0.6771(3) -0.34243(17) 0.9111(2) 0.0599(8) Uani 1 1 d . . .
O4 O 0.8088(3) -0.23917(19) 0.9940(2) 0.0652(8) Uani 1 1 d . . .
O5 O 0.3609(3) -0.14940(18) 0.6988(2) 0.0619(8) Uani 1 1 d . . .
S1 S 0.51889(10) 0.17803(7) 0.74987(8) 0.0579(3) Uani 1 1 d . . .
Br1 Br 0.13867(4) 0.00622(4) 0.78253(3) 0.0753(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
C1 S1 1.749(5) . ?
C2 O1 1.414(5) . ?
C2 O2 1.420(6) . ?
C3 O3 1.399(5) . ?
C3 O4 1.428(5) . ?
C4 C5 1.362(6) . ?
C4 C11 1.370(6) . ?
C5 C14 1.380(5) . ?
C6 C7 1.340(5) . ?
C6 C21 1.414(5) . ?
C7 C9 1.375(5) . ?
C7 O1 1.376(4) . ?
C9 C16 1.351(5) . ?
C9 O2 1.376(4) . ?
C11 C12 1.378(5) . ?
C12 C18 1.380(5) . ?
C13 C20 1.342(5) . ?
C13 C24 1.428(5) . ?
C14 C18 1.373(5) . ?
C15 C24 1.391(5) . ?
C15 C17 1.408(5) . ?
C15 C22 1.452(4) . ?
C16 C25 1.405(5) . ?
C17 C19 1.355(5) . ?
C18 N1 1.452(4) . ?
C19 C20 1.388(5) . ?
C19 O3 1.397(4) . ?
C20 O4 1.360(4) . ?
C21 C25 1.379(5) . ?
C21 C23 1.492(5) . ?
C22 O5 1.227(4) . ?
C22 C23 1.444(5) . ?
C23 C26 1.364(5) . ?
C24 N1 1.395(4) . ?
C25 Br1 1.896(4) . ?
C26 N1 1.375(4) . ?
C26 S1 1.776(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
O1 C2 O2 109.1(3) . . ?
O3 C3 O4 109.6(3) . . ?
C5 C4 C11 119.8(4) . . ?
C4 C5 C14 120.4(4) . . ?
C7 C6 C21 119.0(3) . . ?
C6 C7 C9 122.2(4) . . ?
C6 C7 O1 128.2(4) . . ?
C9 C7 O1 109.6(3) . . ?
C16 C9 C7 121.7(3) . . ?
C16 C9 O2 128.3(4) . . ?
C7 C9 O2 110.0(4) . . ?
C4 C11 C12 120.8(4) . . ?
C11 C12 C18 118.8(4) . . ?
C20 C13 C24 116.8(3) . . ?
C18 C14 C5 119.5(4) . . ?
C24 C15 C17 121.0(3) . . ?
C24 C15 C22 121.0(3) . . ?
C17 C15 C22 118.0(3) . . ?
C9 C16 C25 116.4(4) . . ?
C19 C17 C15 117.0(3) . . ?
C14 C18 C12 120.6(3) . . ?
C14 C18 N1 119.7(3) . . ?
C12 C18 N1 119.6(3) . . ?
C17 C19 C20 122.1(3) . . ?
C17 C19 O3 128.5(3) . . ?
C20 C19 O3 109.4(3) . . ?
C13 C20 O4 127.6(3) . . ?
C13 C20 C19 122.8(3) . . ?
O4 C20 C19 109.6(3) . . ?
C25 C21 C6 117.5(3) . . ?
C25 C21 C23 123.5(3) . . ?
C6 C21 C23 118.9(3) . . ?
O5 C22 C23 122.5(3) . . ?
O5 C22 C15 121.7(3) . . ?
C23 C22 C15 115.8(3) . . ?
C26 C23 C22 121.2(3) . . ?
C26 C23 C21 122.3(3) . . ?
C22 C23 C21 116.2(3) . . ?
C15 C24 N1 119.9(3) . . ?
C15 C24 C13 120.2(3) . . ?
N1 C24 C13 119.9(3) . . ?
C21 C25 C16 123.1(4) . . ?
C21 C25 Br1 119.8(3) . . ?
C16 C25 Br1 117.1(3) . . ?
C23 C26 N1 121.6(3) . . ?
C23 C26 S1 122.1(3) . . ?
N1 C26 S1 116.2(2) . . ?
C26 N1 C24 120.5(3) . . ?
C26 N1 C18 121.7(3) . . ?
C24 N1 C18 117.6(3) . . ?
C7 O1 C2 105.8(3) . . ?
C9 O2 C2 105.4(3) . . ?
C19 O3 C3 105.0(3) . . ?
C20 O4 C3 105.9(3) . . ?
C1 S1 C26 101.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.73
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_8a
_database_code_depnum_ccdc_archive 'CCDC 1492146'
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H13 N O2'
_chemical_formula_weight         311.32

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   5.2728(2)
_cell_length_b                   25.3300(7)
_cell_length_c                   11.4784(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.154(2)
_cell_angle_gamma                90.00
_cell_volume                     1513.53(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3346
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      27.1

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.6902
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS Bruker, 2007)'

_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  'Bruker SMART APEX CCD diffractometer'
_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            19781
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.12
_reflns_number_total             3346
_reflns_number_gt                2275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       'SMART, SAINT'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond (Brandenburg, 1999)'
_computing_publication_material  'SHELXTLCIF-97 (Sheldrick, 2008)'

_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)+(0.0851P)²+0.0310P] 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     SHELXL
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3346
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1240
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 -0.3043(4) 0.51079(6) 0.25323(15) 0.0652(5) Uani 1 1 d . . .
H1 H -0.2336 0.5428 0.2817 0.078 Uiso 1 1 calc R . .
C2 C -0.5173(3) 0.41285(6) 0.16820(15) 0.0592(4) Uani 1 1 d . . .
H2 H -0.5890 0.3809 0.1398 0.071 Uiso 1 1 calc R . .
C3 C -0.6343(4) 0.46034(7) 0.13252(17) 0.0691(5) Uani 1 1 d . . .
H3 H -0.7871 0.4601 0.0794 0.083 Uiso 1 1 calc R . .
C4 C -0.5288(4) 0.50826(7) 0.17425(18) 0.0726(5) Uani 1 1 d . . .
H4 H -0.6122 0.5394 0.1481 0.087 Uiso 1 1 calc R . .
C5 C -0.0395(3) 0.15819(6) 0.46265(17) 0.0641(5) Uani 1 1 d . . .
H5 H -0.1374 0.1395 0.5093 0.077 Uiso 1 1 calc R . .
C6 C 0.2537(3) 0.15918(6) 0.32605(15) 0.0578(4) Uani 1 1 d . . .
H6 H 0.3562 0.1410 0.2806 0.069 Uiso 1 1 calc R . .
C7 C -0.1898(3) 0.46335(6) 0.28777(14) 0.0524(4) Uani 1 1 d . . .
C8 C 0.6675(3) 0.38422(7) 0.59719(15) 0.0603(4) Uani 1 1 d . . .
H8 H 0.8002 0.4032 0.6414 0.072 Uiso 1 1 calc R . .
C9 C 0.6601(3) 0.32964(7) 0.60609(14) 0.0579(4) Uani 1 1 d . . .
H9 H 0.7862 0.3123 0.6581 0.069 Uiso 1 1 calc R . .
C10 C -0.0442(3) 0.21273(6) 0.46248(16) 0.0587(4) Uani 1 1 d . . .
H10 H -0.1424 0.2309 0.5099 0.070 Uiso 1 1 calc R . .
C11 C 0.1090(3) 0.13153(6) 0.39422(14) 0.0568(4) Uani 1 1 d . . .
H11 H 0.1115 0.0948 0.3941 0.068 Uiso 1 1 calc R . .
C12 C 0.2494(3) 0.21368(6) 0.32399(14) 0.0515(4) Uani 1 1 d . . .
H12 H 0.3479 0.2323 0.2775 0.062 Uiso 1 1 calc R . .
C13 C -0.2896(3) 0.41443(6) 0.24765(13) 0.0484(4) Uani 1 1 d . . .
C14 C 0.0726(3) 0.40425(6) 0.37789(13) 0.0475(4) Uani 1 1 d . . .
C15 C 0.4790(3) 0.40988(6) 0.52326(14) 0.0560(4) Uani 1 1 d . . .
H15 H 0.4822 0.4465 0.5183 0.067 Uiso 1 1 calc R . .
C16 C 0.4687(3) 0.30068(6) 0.53915(13) 0.0508(4) Uani 1 1 d . . .
H16 H 0.4665 0.2641 0.5464 0.061 Uiso 1 1 calc R . .
C17 C -0.1135(3) 0.37654(6) 0.30849(12) 0.0456(4) Uani 1 1 d . . .
C18 C -0.1119(3) 0.31947(6) 0.30805(13) 0.0454(4) Uani 1 1 d . . .
C19 C 0.0977(2) 0.23997(5) 0.39154(12) 0.0442(4) Uani 1 1 d . . .
C20 C 0.2789(3) 0.32601(6) 0.46076(12) 0.0440(4) Uani 1 1 d . . .
C21 C 0.2809(3) 0.38162(6) 0.45484(12) 0.0464(4) Uani 1 1 d . . .
N1 N 0.0876(2) 0.29711(4) 0.38858(10) 0.0453(3) Uani 1 1 d . . .
O1 O -0.2670(2) 0.29179(4) 0.24447(10) 0.0593(3) Uani 1 1 d . . .
O2 O 0.0346(2) 0.45760(4) 0.36818(10) 0.0561(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 C4 1.373(3) . ?
C1 C7 1.375(2) . ?
C2 C3 1.384(2) . ?
C2 C13 1.388(2) . ?
C3 C4 1.388(3) . ?
C5 C11 1.372(2) . ?
C5 C10 1.382(2) . ?
C6 C11 1.369(2) . ?
C6 C12 1.381(2) . ?
C7 O2 1.3874(19) . ?
C7 C13 1.395(2) . ?
C8 C15 1.365(2) . ?
C8 C9 1.387(2) . ?
C9 C16 1.378(2) . ?
C10 C19 1.376(2) . ?
C12 C19 1.3718(19) . ?
C13 C17 1.4370(19) . ?
C14 C17 1.357(2) . ?
C14 O2 1.3680(17) . ?
C14 C21 1.416(2) . ?
C15 C21 1.400(2) . ?
C16 C20 1.391(2) . ?
C17 C18 1.445(2) . ?
C18 O1 1.2259(16) . ?
C18 N1 1.4044(17) . ?
C19 N1 1.4485(17) . ?
C20 N1 1.4052(17) . ?
C20 C21 1.411(2) . ?

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
C4 C1 C7 116.26(16) . . ?
C3 C2 C13 117.89(16) . . ?
C2 C3 C4 121.50(18) . . ?
C1 C4 C3 121.64(16) . . ?
C11 C5 C10 120.20(15) . . ?
C11 C6 C12 120.79(14) . . ?
C1 C7 O2 124.92(15) . . ?
C1 C7 C13 123.76(17) . . ?
O2 C7 C13 111.31(13) . . ?
C15 C8 C9 119.60(15) . . ?
C16 C9 C8 121.06(16) . . ?
C19 C10 C5 119.40(14) . . ?
C6 C11 C5 119.75(15) . . ?
C19 C12 C6 119.02(14) . . ?
C2 C13 C7 118.94(14) . . ?
C2 C13 C17 136.44(14) . . ?
C7 C13 C17 104.60(13) . . ?
C17 C14 O2 112.35(13) . . ?
C17 C14 C21 124.98(14) . . ?
O2 C14 C21 122.65(13) . . ?
C8 C15 C21 120.68(15) . . ?
C9 C16 C20 120.18(15) . . ?
C14 C17 C13 106.90(13) . . ?
C14 C17 C18 121.01(13) . . ?
C13 C17 C18 132.06(13) . . ?
O1 C18 N1 121.31(13) . . ?
O1 C18 C17 124.78(13) . . ?
N1 C18 C17 113.91(12) . . ?
C12 C19 C10 120.81(14) . . ?
C12 C19 N1 119.62(12) . . ?
C10 C19 N1 119.57(12) . . ?
C16 C20 N1 121.08(13) . . ?
C16 C20 C21 118.79(13) . . ?
N1 C20 C21 120.13(13) . . ?
C15 C21 C20 119.61(14) . . ?
C15 C21 C14 125.34(14) . . ?
C20 C21 C14 115.05(12) . . ?
C18 N1 C20 124.77(12) . . ?
C18 N1 C19 116.07(11) . . ?
C20 N1 C19 119.10(11) . . ?
C14 O2 C7 104.84(11) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.12
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.070
