# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 986777'
_audit_update_record             
;
2015-08-01 deposited with the CCDC.
2015-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 I O2'
_chemical_formula_weight         374.16

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   11.327(4)
_cell_length_b                   11.780(5)
_cell_length_c                   10.747(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.540(4)
_cell_angle_gamma                90.00
_cell_volume                     1429.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1824
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.22

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    2.238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_T_max  0.6758
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6008
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2592
_reflns_number_gt                1793
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0328P)²+1.3095P] 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         2592
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.3705(4) 0.8299(4) 0.5624(4) 0.0441(11) Uani 1 1 d . . .
C2 C 0.4900(4) 0.8152(4) 0.5563(4) 0.0462(12) Uani 1 1 d . . .
C3 C 0.5736(4) 0.8891(4) 0.6172(4) 0.0389(10) Uani 1 1 d . . .
C4 C 0.6969(5) 0.8762(4) 0.6174(4) 0.0550(13) Uani 1 1 d . . .
H4 H 0.7273 0.8157 0.5744 0.066 Uiso 1 1 calc R . .
C5 C 0.7721(5) 0.9494(5) 0.6783(5) 0.0622(14) Uani 1 1 d . . .
H5 H 0.8533 0.9380 0.6776 0.075 Uiso 1 1 calc R . .
C6 C 0.7300(4) 1.0425(5) 0.7427(5) 0.0597(14) Uani 1 1 d . . .
H6 H 0.7829 1.0930 0.7837 0.072 Uiso 1 1 calc R . .
C7 C 0.6122(4) 1.0586(4) 0.7451(4) 0.0493(12) Uani 1 1 d . . .
H7 H 0.5845 1.1204 0.7880 0.059 Uiso 1 1 calc R . .
C8 C 0.5309(4) 0.9832(3) 0.6836(4) 0.0374(10) Uani 1 1 d . . .
C9 C 0.4088(4) 0.9964(3) 0.6892(4) 0.0405(11) Uani 1 1 d . . .
H9 H 0.3810 1.0580 0.7324 0.049 Uiso 1 1 calc R . .
C10 C 0.3288(4) 0.9218(3) 0.6335(4) 0.0397(10) Uani 1 1 d . . .
C11 C 0.1995(4) 0.9382(4) 0.6396(5) 0.0530(13) Uani 1 1 d . . .
C12 C 0.1543(4) 1.0186(4) 0.7305(5) 0.0504(12) Uani 1 1 d . . .
C13 C 0.1853(5) 1.0095(5) 0.8574(5) 0.0636(14) Uani 1 1 d . . .
H13 H 0.2405 0.9555 0.8868 0.076 Uiso 1 1 calc R . .
C14 C 0.1347(5) 1.0800(6) 0.9396(6) 0.0817(18) Uani 1 1 d . . .
H14 H 0.1537 1.0722 1.0250 0.098 Uiso 1 1 calc R . .
C15 C 0.0564(5) 1.1617(6) 0.8961(7) 0.0814(18) Uani 1 1 d . . .
H15 H 0.0234 1.2103 0.9521 0.098 Uiso 1 1 calc R . .
C16 C 0.0263(5) 1.1727(5) 0.7723(8) 0.0831(19) Uani 1 1 d . . .
H16 H -0.0262 1.2293 0.7436 0.100 Uiso 1 1 calc R . .
C17 C 0.0738(4) 1.0995(5) 0.6879(6) 0.0652(15) Uani 1 1 d . . .
H17 H 0.0512 1.1054 0.6031 0.078 Uiso 1 1 calc R . .
I1 I 0.54250(4) 0.68029(3) 0.44782(3) 0.07476(18) Uani 1 1 d . . .
O1 O 0.2919(3) 0.7563(3) 0.5039(3) 0.0642(10) Uani 1 1 d . . .
H1 H 0.3026 0.7537 0.4294 0.096 Uiso 1 1 calc R . .
O2 O 0.1279(3) 0.8852(3) 0.5695(4) 0.0719(11) 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 O1 1.360(5) . ?
C1 C2 1.371(7) . ?
C1 C10 1.427(6) . ?
C2 C3 1.409(6) . ?
C2 I1 2.085(4) . ?
C3 C4 1.405(6) . ?
C3 C8 1.424(6) . ?
C4 C5 1.345(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.349(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(6) . ?
C9 C10 1.366(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.485(6) . ?
C11 O2 1.232(5) . ?
C11 C12 1.480(7) . ?
C12 C17 1.372(7) . ?
C12 C13 1.385(7) . ?
C13 C14 1.371(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.353(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
O1 H1 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
O1 C1 C2 120.7(4) . . ?
O1 C1 C10 119.9(4) . . ?
C2 C1 C10 119.4(4) . . ?
C1 C2 C3 122.0(4) . . ?
C1 C2 I1 116.7(3) . . ?
C3 C2 I1 121.3(3) . . ?
C4 C3 C2 124.4(4) . . ?
C4 C3 C8 117.4(4) . . ?
C2 C3 C8 118.2(4) . . ?
C5 C4 C3 121.5(5) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 121.0(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 119.7(5) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 C3 119.0(4) . . ?
C7 C8 C3 119.4(4) . . ?
C10 C9 C8 122.3(4) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C1 119.2(4) . . ?
C9 C10 C11 121.3(4) . . ?
C1 C10 C11 119.5(4) . . ?
O2 C11 C12 118.9(4) . . ?
O2 C11 C10 120.7(5) . . ?
C12 C11 C10 120.4(4) . . ?
C17 C12 C13 119.5(5) . . ?
C17 C12 C11 118.7(5) . . ?
C13 C12 C11 121.7(5) . . ?
C14 C13 C12 120.1(5) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.0(6) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.7(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.1(6) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.6(6) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C1 O1 H1 109.5 . . ?

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 C1 C2 C3 -179.2(4) . . . . ?
C10 C1 C2 C3 -0.7(6) . . . . ?
O1 C1 C2 I1 2.6(5) . . . . ?
C10 C1 C2 I1 -179.0(3) . . . . ?
C1 C2 C3 C4 178.0(4) . . . . ?
I1 C2 C3 C4 -3.8(6) . . . . ?
C1 C2 C3 C8 -1.8(6) . . . . ?
I1 C2 C3 C8 176.3(3) . . . . ?
C2 C3 C4 C5 -179.5(4) . . . . ?
C8 C3 C4 C5 0.4(7) . . . . ?
C3 C4 C5 C6 -0.9(8) . . . . ?
C4 C5 C6 C7 0.7(8) . . . . ?
C5 C6 C7 C8 -0.1(7) . . . . ?
C6 C7 C8 C9 177.5(4) . . . . ?
C6 C7 C8 C3 -0.4(7) . . . . ?
C4 C3 C8 C9 -177.7(4) . . . . ?
C2 C3 C8 C9 2.1(6) . . . . ?
C4 C3 C8 C7 0.3(6) . . . . ?
C2 C3 C8 C7 -179.9(4) . . . . ?
C7 C8 C9 C10 -177.8(4) . . . . ?
C3 C8 C9 C10 0.2(6) . . . . ?
C8 C9 C10 C1 -2.8(6) . . . . ?
C8 C9 C10 C11 -179.4(4) . . . . ?
O1 C1 C10 C9 -178.5(4) . . . . ?
C2 C1 C10 C9 3.0(6) . . . . ?
O1 C1 C10 C11 -1.8(6) . . . . ?
C2 C1 C10 C11 179.7(4) . . . . ?
C9 C10 C11 O2 165.2(4) . . . . ?
C1 C10 C11 O2 -11.4(7) . . . . ?
C9 C10 C11 C12 -14.9(6) . . . . ?
C1 C10 C11 C12 168.5(4) . . . . ?
O2 C11 C12 C17 -52.2(6) . . . . ?
C10 C11 C12 C17 127.8(5) . . . . ?
O2 C11 C12 C13 123.6(5) . . . . ?
C10 C11 C12 C13 -56.3(6) . . . . ?
C17 C12 C13 C14 0.8(8) . . . . ?
C11 C12 C13 C14 -175.0(5) . . . . ?
C12 C13 C14 C15 -2.1(9) . . . . ?
C13 C14 C15 C16 1.2(9) . . . . ?
C14 C15 C16 C17 0.9(9) . . . . ?
C13 C12 C17 C16 1.2(7) . . . . ?
C11 C12 C17 C16 177.2(5) . . . . ?
C15 C16 C17 C12 -2.1(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 986778'
_audit_update_record             
;
2015-08-01 deposited with the CCDC.
2015-10-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 I O2 S'
_chemical_formula_weight         380.18

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'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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'

_cell_length_a                   16.603(3)
_cell_length_b                   4.1488(8)
_cell_length_c                   19.295(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1329.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5710
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      31.01

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.900
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    2.560
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6849
_exptl_absorpt_correction_T_max  0.7839
_exptl_absorpt_process_details   ?

_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            6961
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2584
_reflns_number_gt                2485
_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    '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)+(0.0400P)²+0.6343P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_number_reflns         2584
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.179
_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 0.1522(3) 0.1870(13) 0.6239(2) 0.0437(11) Uani 1 1 d . . .
C2 C 0.2243(3) 0.1014(13) 0.6569(2) 0.0464(11) Uani 1 1 d . . .
H2 H 0.2225 -0.0132 0.6983 0.056 Uiso 1 1 calc R . .
C3 C 0.2972(4) 0.1837(15) 0.6292(3) 0.0553(13) Uani 1 1 d . . .
H3 H 0.3447 0.1228 0.6512 0.066 Uiso 1 1 calc R . .
C4 C 0.3001(4) 0.3589(15) 0.5678(3) 0.0603(15) Uani 1 1 d . . .
H4 H 0.3496 0.4207 0.5497 0.072 Uiso 1 1 calc R . .
C5 C 0.2304(4) 0.4417(16) 0.5338(3) 0.0579(14) Uani 1 1 d . . .
H5 H 0.2329 0.5562 0.4924 0.070 Uiso 1 1 calc R . .
C6 C 0.1578(3) 0.3560(14) 0.5607(3) 0.0515(14) Uani 1 1 d . . .
H6 H 0.1109 0.4097 0.5369 0.062 Uiso 1 1 calc R . .
C7 C 0.0722(3) 0.0886(16) 0.6488(3) 0.0510(12) Uani 1 1 d . . .
C8 C 0.0501(3) 0.1091(12) 0.7230(2) 0.0361(9) Uani 1 1 d . . .
C9 C -0.0243(3) -0.0283(12) 0.7452(2) 0.0391(9) Uani 1 1 d . . .
C10 C -0.0475(3) -0.0065(11) 0.8137(2) 0.0384(9) Uani 1 1 d . . .
C11 C 0.0014(3) 0.1467(11) 0.8624(2) 0.0375(10) Uani 1 1 d . . .
C12 C 0.0749(2) 0.2815(9) 0.8396(3) 0.0372(8) Uani 1 1 d . . .
C13 C 0.0990(3) 0.2672(11) 0.7715(2) 0.0375(9) Uani 1 1 d . . .
H13 H 0.1473 0.3613 0.7578 0.045 Uiso 1 1 calc R . .
C14 C -0.0108(3) 0.1996(15) 0.9354(3) 0.0516(13) Uani 1 1 d . . .
H14 H -0.0558 0.1293 0.9597 0.062 Uiso 1 1 calc R . .
C15 C 0.0510(3) 0.3634(14) 0.9644(2) 0.0488(12) Uani 1 1 d . . .
H15 H 0.0526 0.4162 1.0112 0.059 Uiso 1 1 calc R . .
I1 I -0.159993(17) -0.18702(8) 0.84267(2) 0.05865(14) Uani 1 1 d . . .
O1 O 0.0214(3) -0.0004(16) 0.60599(19) 0.0805(17) Uani 1 1 d . . .
O2 O -0.0727(3) -0.1840(10) 0.7006(2) 0.0568(10) Uani 1 1 d . . .
H2A H -0.0613 -0.1313 0.6608 0.085 Uiso 1 1 calc R . .
S1 S 0.12646(7) 0.4659(3) 0.90735(6) 0.0461(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 C2 1.401(7) . ?
C1 C6 1.411(8) . ?
C1 C7 1.470(7) . ?
C2 C3 1.368(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.237(6) . ?
C7 C8 1.480(6) . ?
C8 C13 1.403(7) . ?
C8 C9 1.427(6) . ?
C9 O2 1.344(6) . ?
C9 C10 1.379(6) . ?
C10 C11 1.396(6) . ?
C10 I1 2.088(4) . ?
C11 C12 1.413(6) . ?
C11 C14 1.438(6) . ?
C12 C13 1.374(9) . ?
C12 S1 1.740(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.352(8) . ?
C14 H14 0.9300 . ?
C15 S1 1.721(6) . ?
C15 H15 0.9300 . ?
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
C2 C1 C6 117.6(5) . . ?
C2 C1 C7 123.6(5) . . ?
C6 C1 C7 118.6(5) . . ?
C3 C2 C1 121.0(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.9(5) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 121.2(5) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O1 C7 C1 118.8(5) . . ?
O1 C7 C8 119.6(5) . . ?
C1 C7 C8 121.6(4) . . ?
C13 C8 C9 119.2(4) . . ?
C13 C8 C7 121.9(4) . . ?
C9 C8 C7 118.9(4) . . ?
O2 C9 C10 118.6(4) . . ?
O2 C9 C8 121.1(4) . . ?
C10 C9 C8 120.3(4) . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 I1 118.9(3) . . ?
C11 C10 I1 120.2(3) . . ?
C10 C11 C12 118.2(4) . . ?
C10 C11 C14 130.3(5) . . ?
C12 C11 C14 111.5(5) . . ?
C13 C12 C11 122.2(4) . . ?
C13 C12 S1 126.5(3) . . ?
C11 C12 S1 111.3(4) . . ?
C12 C13 C8 119.3(4) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C15 C14 C11 112.0(5) . . ?
C15 C14 H14 124.0 . . ?
C11 C14 H14 124.0 . . ?
C14 C15 S1 114.3(4) . . ?
C14 C15 H15 122.8 . . ?
S1 C15 H15 122.8 . . ?
C9 O2 H2A 109.5 . . ?
C15 S1 C12 90.8(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
C6 C1 C2 C3 1.0(8) . . . . ?
C7 C1 C2 C3 176.1(5) . . . . ?
C1 C2 C3 C4 0.9(8) . . . . ?
C2 C3 C4 C5 -2.0(9) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?
C4 C5 C6 C1 1.1(9) . . . . ?
C2 C1 C6 C5 -2.0(8) . . . . ?
C7 C1 C6 C5 -177.3(6) . . . . ?
C2 C1 C7 O1 -138.1(6) . . . . ?
C6 C1 C7 O1 36.9(9) . . . . ?
C2 C1 C7 C8 44.9(9) . . . . ?
C6 C1 C7 C8 -140.1(6) . . . . ?
O1 C7 C8 C13 -167.1(6) . . . . ?
C1 C7 C8 C13 9.9(8) . . . . ?
O1 C7 C8 C9 11.1(9) . . . . ?
C1 C7 C8 C9 -171.9(5) . . . . ?
C13 C8 C9 O2 -179.5(4) . . . . ?
C7 C8 C9 O2 2.3(7) . . . . ?
C13 C8 C9 C10 -0.2(7) . . . . ?
C7 C8 C9 C10 -178.4(5) . . . . ?
O2 C9 C10 C11 178.6(4) . . . . ?
C8 C9 C10 C11 -0.7(7) . . . . ?
O2 C9 C10 I1 -4.3(6) . . . . ?
C8 C9 C10 I1 176.4(3) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
I1 C10 C11 C12 -176.4(3) . . . . ?
C9 C10 C11 C14 179.4(5) . . . . ?
I1 C10 C11 C14 2.4(7) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C14 C11 C12 C13 -178.7(4) . . . . ?
C10 C11 C12 S1 179.1(3) . . . . ?
C14 C11 C12 S1 0.2(5) . . . . ?
C11 C12 C13 C8 -1.1(6) . . . . ?
S1 C12 C13 C8 -179.8(3) . . . . ?
C9 C8 C13 C12 1.1(7) . . . . ?
C7 C8 C13 C12 179.3(5) . . . . ?
C10 C11 C14 C15 -179.1(5) . . . . ?
C12 C11 C14 C15 -0.3(6) . . . . ?
C11 C14 C15 S1 0.3(7) . . . . ?
C14 C15 S1 C12 -0.2(5) . . . . ?
C13 C12 S1 C15 178.8(4) . . . . ?
C11 C12 S1 C15 0.0(3) . . . . ?

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
C3 H3 O2 0.93 2.47 3.295(7) 147.9 3_545
O2 H2A O1 0.82 1.82 2.520(6) 143.1 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.182
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 986779'
_audit_update_record             
;
2015-08-01 deposited with the CCDC.
2015-10-12 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 H14 O2'
_chemical_formula_weight         298.32

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'
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                   13.966(2)
_cell_length_b                   12.7793(19)
_cell_length_c                   8.4353(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.374(2)
_cell_angle_gamma                90.00
_cell_volume                     1480.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5464
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      31.89

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9865
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_process_details   ?

_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            7985
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2741
_reflns_number_gt                2235
_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    '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)+(0.0748P)²+0.3721P] 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       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2741
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.59832(13) 0.50029(14) 0.2028(2) 0.0514(4) Uani 1 1 d . . .
H1 H 0.5580 0.5507 0.1459 0.062 Uiso 1 1 calc R . .
C2 C 0.69410(14) 0.49613(16) 0.1879(2) 0.0615(5) Uani 1 1 d . . .
H2 H 0.7181 0.5438 0.1215 0.074 Uiso 1 1 calc R . .
C3 C 0.75614(13) 0.42125(17) 0.2713(2) 0.0641(5) Uani 1 1 d . . .
H3 H 0.8212 0.4188 0.2604 0.077 Uiso 1 1 calc R . .
C4 C 0.72075(13) 0.35133(16) 0.3694(2) 0.0573(5) Uani 1 1 d . . .
H4 H 0.7624 0.3016 0.4252 0.069 Uiso 1 1 calc R . .
C5 C 0.62250(11) 0.35331(12) 0.38738(19) 0.0445(4) Uani 1 1 d . . .
C6 C 0.55970(11) 0.42941(12) 0.30300(17) 0.0401(4) Uani 1 1 d . . .
C7 C 0.45781(11) 0.43043(11) 0.31996(17) 0.0374(4) Uani 1 1 d . . .
C8 C 0.42488(11) 0.35477(11) 0.42105(18) 0.0394(4) Uani 1 1 d . . .
C9 C 0.49223(12) 0.28024(13) 0.5051(2) 0.0466(4) Uani 1 1 d . . .
H9 H 0.4704 0.2315 0.5723 0.056 Uiso 1 1 calc R . .
C10 C 0.58597(13) 0.27927(13) 0.4890(2) 0.0510(4) Uani 1 1 d . . .
H10 H 0.6279 0.2297 0.5446 0.061 Uiso 1 1 calc R . .
C11 C 0.32679(11) 0.35378(12) 0.43519(18) 0.0407(4) Uani 1 1 d . . .
H11 H 0.3057 0.3040 0.5016 0.049 Uiso 1 1 calc R . .
C12 C 0.25960(11) 0.42394(12) 0.35448(18) 0.0397(4) Uani 1 1 d . . .
C13 C 0.29500(12) 0.50267(12) 0.25962(19) 0.0439(4) Uani 1 1 d . . .
C14 C 0.39066(12) 0.50388(12) 0.24267(19) 0.0434(4) Uani 1 1 d . . .
H14 H 0.4117 0.5548 0.1781 0.052 Uiso 1 1 calc R . .
C15 C 0.15573(11) 0.42161(12) 0.36695(19) 0.0425(4) Uani 1 1 d . . .
C16 C 0.10922(11) 0.32657(12) 0.42175(19) 0.0430(4) Uani 1 1 d . . .
C17 C 0.13638(12) 0.22543(13) 0.3872(2) 0.0509(4) Uani 1 1 d . . .
H17 H 0.1891 0.2148 0.3355 0.061 Uiso 1 1 calc R . .
C18 C 0.08476(14) 0.14072(15) 0.4299(3) 0.0627(5) Uani 1 1 d . . .
H18 H 0.1030 0.0732 0.4066 0.075 Uiso 1 1 calc R . .
C19 C 0.00686(13) 0.15534(16) 0.5064(3) 0.0604(5) Uani 1 1 d . . .
H19 H -0.0273 0.0979 0.5347 0.072 Uiso 1 1 calc R . .
C20 C -0.02055(13) 0.25478(16) 0.5409(2) 0.0601(5) Uani 1 1 d . . .
H20 H -0.0731 0.2646 0.5932 0.072 Uiso 1 1 calc R . .
C21 C 0.02972(12) 0.34025(14) 0.4982(2) 0.0530(4) Uani 1 1 d . . .
H21 H 0.0103 0.4074 0.5207 0.064 Uiso 1 1 calc R . .
O1 O 0.23531(9) 0.57778(10) 0.18334(17) 0.0627(4) Uani 1 1 d . . .
H1A H 0.1822 0.5741 0.2114 0.094 Uiso 1 1 calc R . .
O2 O 0.10402(9) 0.49891(9) 0.32635(17) 0.0588(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
C1 C2 1.367(3) . ?
C1 C6 1.411(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.413(2) . ?
C5 C10 1.431(2) . ?
C6 C7 1.456(2) . ?
C7 C14 1.402(2) . ?
C7 C8 1.419(2) . ?
C8 C11 1.396(2) . ?
C8 C9 1.433(2) . ?
C9 C10 1.340(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.428(2) . ?
C12 C15 1.474(2) . ?
C13 O1 1.3555(19) . ?
C13 C14 1.369(2) . ?
C14 H14 0.9300 . ?
C15 O2 1.2352(18) . ?
C15 C16 1.490(2) . ?
C16 C21 1.392(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.384(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
O1 H1A 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
C2 C1 C6 121.06(17) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.69(18) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.59(17) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.23(18) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 119.13(16) . . ?
C4 C5 C10 120.82(16) . . ?
C6 C5 C10 120.05(14) . . ?
C1 C6 C5 118.30(15) . . ?
C1 C6 C7 122.63(15) . . ?
C5 C6 C7 119.06(14) . . ?
C14 C7 C8 118.25(14) . . ?
C14 C7 C6 122.97(13) . . ?
C8 C7 C6 118.77(13) . . ?
C11 C8 C7 119.11(13) . . ?
C11 C8 C9 121.22(14) . . ?
C7 C8 C9 119.66(14) . . ?
C10 C9 C8 121.47(15) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C5 120.98(15) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 C8 122.71(14) . . ?
C12 C11 H11 118.6 . . ?
C8 C11 H11 118.6 . . ?
C11 C12 C13 117.34(14) . . ?
C11 C12 C15 122.71(14) . . ?
C13 C12 C15 119.92(14) . . ?
O1 C13 C14 118.08(14) . . ?
O1 C13 C12 121.30(15) . . ?
C14 C13 C12 120.62(14) . . ?
C13 C14 C7 121.84(14) . . ?
C13 C14 H14 119.1 . . ?
C7 C14 H14 119.1 . . ?
O2 C15 C12 119.87(14) . . ?
O2 C15 C16 118.18(14) . . ?
C12 C15 C16 121.91(13) . . ?
C21 C16 C17 118.93(15) . . ?
C21 C16 C15 118.04(14) . . ?
C17 C16 C15 122.78(14) . . ?
C18 C17 C16 119.82(16) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.63(18) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.01(17) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.14(17) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.47(17) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C13 O1 H1A 109.5 . . ?

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
C6 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C3 C4 C5 C10 179.39(16) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C6 C7 -179.06(15) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C10 C5 C6 C1 -179.34(14) . . . . ?
C4 C5 C6 C7 179.16(13) . . . . ?
C10 C5 C6 C7 -0.6(2) . . . . ?
C1 C6 C7 C14 -2.2(2) . . . . ?
C5 C6 C7 C14 179.08(13) . . . . ?
C1 C6 C7 C8 178.74(13) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C14 C7 C8 C11 2.3(2) . . . . ?
C6 C7 C8 C11 -178.61(12) . . . . ?
C14 C7 C8 C9 -178.42(14) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C11 C8 C9 C10 178.41(15) . . . . ?
C7 C8 C9 C10 -0.9(2) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
C4 C5 C10 C9 -179.31(16) . . . . ?
C6 C5 C10 C9 0.4(2) . . . . ?
C7 C8 C11 C12 -0.1(2) . . . . ?
C9 C8 C11 C12 -179.33(14) . . . . ?
C8 C11 C12 C13 -2.9(2) . . . . ?
C8 C11 C12 C15 178.79(14) . . . . ?
C11 C12 C13 O1 -176.56(14) . . . . ?
C15 C12 C13 O1 1.8(2) . . . . ?
C11 C12 C13 C14 3.8(2) . . . . ?
C15 C12 C13 C14 -177.91(14) . . . . ?
O1 C13 C14 C7 178.69(14) . . . . ?
C12 C13 C14 C7 -1.6(2) . . . . ?
C8 C7 C14 C13 -1.5(2) . . . . ?
C6 C7 C14 C13 179.49(13) . . . . ?
C11 C12 C15 O2 162.42(15) . . . . ?
C13 C12 C15 O2 -15.8(2) . . . . ?
C11 C12 C15 C16 -20.0(2) . . . . ?
C13 C12 C15 C16 161.80(14) . . . . ?
O2 C15 C16 C21 -30.6(2) . . . . ?
C12 C15 C16 C21 151.71(15) . . . . ?
O2 C15 C16 C17 143.57(17) . . . . ?
C12 C15 C16 C17 -34.1(2) . . . . ?
C21 C16 C17 C18 -0.4(3) . . . . ?
C15 C16 C17 C18 -174.55(17) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C19 C20 C21 C16 -0.8(3) . . . . ?
C17 C16 C21 C20 0.8(3) . . . . ?
C15 C16 C21 C20 175.26(16) . . . . ?

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
O1 H1A O2 0.82 1.85 2.5749(18) 146.1 .

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.042
