# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1021476'
_audit_update_record             
;
2014-08-27 deposited with the CCDC.
2015-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N O'

_chemical_formula_sum            'C21 H19 N O'
_chemical_formula_weight         301.37

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.7818(9)
_cell_length_b                   8.1980(10)
_cell_length_c                   14.5361(18)
_cell_angle_alpha                104.484(6)
_cell_angle_beta                 91.999(6)
_cell_angle_gamma                111.108(5)
_cell_volume                     829.56(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5786
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.66

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9717
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17649
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0712
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         24.99
_reflns_number_total             17649
_reflns_number_gt                11526
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-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)+(0.0603P)²+0.7615P] 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       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         17649
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.2017
_refine_ls_wR_factor_gt          0.1794
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.7066(2) 0.7306(3) 0.07380(13) 0.0559(5) Uani 1 1 d . . .
C2 C 0.7808(3) 0.6090(4) 0.02606(15) 0.0782(7) Uani 1 1 d . . .
H2 H 0.8349 0.6272 -0.0285 0.094 Uiso 1 1 calc R . .
C3 C 0.7778(3) 0.4639(3) 0.05576(18) 0.0838(7) Uani 1 1 d U . .
H3 H 0.8296 0.3853 0.0217 0.101 Uiso 1 1 calc R . .
C4 C 0.6988(3) 0.4322(3) 0.13578(17) 0.0739(6) Uani 1 1 d U . .
H4 H 0.6968 0.3328 0.1562 0.089 Uiso 1 1 calc R . .
C5 C 0.6236(2) 0.5482(3) 0.18453(14) 0.0550(5) Uani 1 1 d . . .
H5 H 0.5719 0.5289 0.2395 0.066 Uiso 1 1 calc R . .
C6 C 0.6224(2) 0.6948(2) 0.15380(12) 0.0454(4) Uani 1 1 d . . .
C7 C 0.5316(2) 0.8078(2) 0.20410(12) 0.0470(4) Uani 1 1 d . . .
C8 C 0.4506(2) 0.8966(2) 0.24394(12) 0.0449(4) Uani 1 1 d . . .
C9 C 0.3386(2) 0.9957(2) 0.28994(11) 0.0398(4) Uani 1 1 d . . .
C10 C 0.7129(3) 0.8906(3) 0.04099(15) 0.0817(7) Uani 1 1 d . . .
H10A H 0.6564 0.9596 0.0837 0.123 Uiso 1 1 calc R . .
H10B H 0.6465 0.8492 -0.0227 0.123 Uiso 1 1 calc R . .
H10C H 0.8400 0.9662 0.0407 0.123 Uiso 1 1 calc R . .
C11 C 0.4655(2) 1.1750(2) 0.36364(12) 0.0437(4) Uani 1 1 d . . .
C12 C 0.2734(2) 1.0029(2) 0.44748(12) 0.0368(4) Uani 1 1 d . . .
C13 C 0.1936(2) 0.9451(3) 0.52162(13) 0.0509(5) Uani 1 1 d . . .
H13 H 0.2330 1.0157 0.5850 0.061 Uiso 1 1 calc R . .
C14 C 0.0500(3) 0.7745(3) 0.49680(17) 0.0644(6) Uani 1 1 d . . .
H14 H -0.0076 0.7301 0.5454 0.077 Uiso 1 1 calc R . .
C15 C -0.0096(3) 0.6700(3) 0.40473(17) 0.0644(6) Uani 1 1 d . . .
H15 H -0.1078 0.5575 0.3913 0.077 Uiso 1 1 calc R . .
C16 C 0.0748(2) 0.7297(2) 0.33091(14) 0.0530(5) Uani 1 1 d . . .
H16 H 0.0356 0.6582 0.2676 0.064 Uiso 1 1 calc R . .
C17 C 0.2184(2) 0.8976(2) 0.35331(12) 0.0388(4) Uani 1 1 d . . .
C18 C 0.2321(2) 1.0392(3) 0.21346(12) 0.0550(5) Uani 1 1 d . . .
H18A H 0.3218 1.1205 0.1841 0.066 Uiso 1 1 calc R . .
H18B H 0.1636 0.9271 0.1636 0.066 Uiso 1 1 calc R . .
C19 C 0.1008(3) 1.1240(3) 0.25116(15) 0.0737(6) Uani 1 1 d . . .
H19 H 0.0036 1.0540 0.2774 0.088 Uiso 1 1 calc R . .
C20 C 0.1044(4) 1.2756(4) 0.25204(19) 0.1098(9) Uani 1 1 d . . .
H20A H 0.1984 1.3519 0.2268 0.132 Uiso 1 1 calc R . .
H20B H 0.0132 1.3139 0.2780 0.132 Uiso 1 1 calc R . .
C21 C 0.5126(2) 1.3115(2) 0.53960(12) 0.0535(5) Uani 1 1 d . . .
H21A H 0.5446 1.2604 0.5871 0.080 Uiso 1 1 calc R . .
H21B H 0.4306 1.3715 0.5630 0.080 Uiso 1 1 calc R . .
H21C H 0.6235 1.3982 0.5267 0.080 Uiso 1 1 calc R . .
N1 N 0.42016(17) 1.16685(18) 0.45175(9) 0.0395(3) Uani 1 1 d . . .
O1 O 0.58688(17) 1.30119(17) 0.34580(9) 0.0631(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 1.381(3) . ?
C1 C6 1.397(2) . ?
C1 C10 1.490(3) . ?
C2 C3 1.356(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.436(2) . ?
C7 C8 1.187(2) . ?
C8 C9 1.465(2) . ?
C9 C17 1.503(2) . ?
C9 C11 1.542(2) . ?
C9 C18 1.548(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O1 1.2152(18) . ?
C11 N1 1.352(2) . ?
C12 C13 1.365(2) . ?
C12 C17 1.380(2) . ?
C12 N1 1.4006(19) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.355(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(2) . ?
C16 H16 0.9300 . ?
C18 C19 1.479(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.230(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
C21 N1 1.4556(19) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C2 C1 C6 116.7(2) . . ?
C2 C1 C10 121.8(2) . . ?
C6 C1 C10 121.49(18) . . ?
C3 C2 C1 122.4(2) . . ?
C3 C2 H2 118.8 . . ?
C1 C2 H2 118.8 . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 120.28(17) . . ?
C5 C6 C7 119.34(16) . . ?
C1 C6 C7 120.37(17) . . ?
C8 C7 C6 177.64(19) . . ?
C7 C8 C9 176.05(19) . . ?
C8 C9 C17 111.19(14) . . ?
C8 C9 C11 109.87(13) . . ?
C17 C9 C11 101.40(12) . . ?
C8 C9 C18 109.98(13) . . ?
C17 C9 C18 114.68(13) . . ?
C11 C9 C18 109.37(13) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 N1 125.83(16) . . ?
O1 C11 C9 125.94(16) . . ?
N1 C11 C9 108.23(14) . . ?
C13 C12 C17 122.40(16) . . ?
C13 C12 N1 128.15(16) . . ?
C17 C12 N1 109.43(14) . . ?
C12 C13 C14 116.08(18) . . ?
C12 C13 H13 122.0 . . ?
C14 C13 H13 122.0 . . ?
C15 C14 C13 122.72(19) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C16 120.34(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 118.30(19) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C16 C17 C12 120.14(16) . . ?
C16 C17 C9 130.48(16) . . ?
C12 C17 C9 109.37(14) . . ?
C19 C18 C9 114.35(15) . . ?
C19 C18 H18A 108.7 . . ?
C9 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C9 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 128.0(3) . . ?
C20 C19 H19 116.0 . . ?
C18 C19 H19 116.0 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 N1 C12 111.53(14) . . ?
C11 N1 C21 123.84(14) . . ?
C12 N1 C21 124.63(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
C6 C1 C2 C3 -1.7(3) . . . . ?
C10 C1 C2 C3 179.3(2) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C4 C5 C6 C1 -2.8(3) . . . . ?
C4 C5 C6 C7 176.29(16) . . . . ?
C2 C1 C6 C5 2.9(3) . . . . ?
C10 C1 C6 C5 -178.00(17) . . . . ?
C2 C1 C6 C7 -176.14(16) . . . . ?
C10 C1 C6 C7 2.9(3) . . . . ?
C5 C6 C7 C8 -80(5) . . . . ?
C1 C6 C7 C8 99(5) . . . . ?
C6 C7 C8 C9 6(7) . . . . ?
C7 C8 C9 C17 61(3) . . . . ?
C7 C8 C9 C11 173(3) . . . . ?
C7 C8 C9 C18 -67(3) . . . . ?
C8 C9 C11 O1 63.1(2) . . . . ?
C17 C9 C11 O1 -179.16(16) . . . . ?
C18 C9 C11 O1 -57.7(2) . . . . ?
C8 C9 C11 N1 -116.16(15) . . . . ?
C17 C9 C11 N1 1.55(16) . . . . ?
C18 C9 C11 N1 123.04(14) . . . . ?
C17 C12 C13 C14 -1.3(2) . . . . ?
N1 C12 C13 C14 -179.50(14) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 C12 -0.8(2) . . . . ?
C15 C16 C17 C9 178.24(16) . . . . ?
C13 C12 C17 C16 1.8(2) . . . . ?
N1 C12 C17 C16 -179.67(13) . . . . ?
C13 C12 C17 C9 -177.37(15) . . . . ?
N1 C12 C17 C9 1.12(17) . . . . ?
C8 C9 C17 C16 -63.9(2) . . . . ?
C11 C9 C17 C16 179.31(16) . . . . ?
C18 C9 C17 C16 61.6(2) . . . . ?
C8 C9 C17 C12 115.15(15) . . . . ?
C11 C9 C17 C12 -1.59(16) . . . . ?
C18 C9 C17 C12 -119.30(15) . . . . ?
C8 C9 C18 C19 174.51(17) . . . . ?
C17 C9 C18 C19 48.3(2) . . . . ?
C11 C9 C18 C19 -64.8(2) . . . . ?
C9 C18 C19 C20 117.7(3) . . . . ?
O1 C11 N1 C12 179.71(16) . . . . ?
C9 C11 N1 C12 -1.01(17) . . . . ?
O1 C11 N1 C21 0.0(3) . . . . ?
C9 C11 N1 C21 179.27(14) . . . . ?
C13 C12 N1 C11 178.33(17) . . . . ?
C17 C12 N1 C11 -0.05(17) . . . . ?
C13 C12 N1 C21 -2.0(2) . . . . ?
C17 C12 N1 C21 179.67(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1022902'
_audit_update_record             
;
2014-09-04 deposited with the CCDC.
2015-06-15 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 H19 N O2'
_chemical_formula_weight         317.37

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   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                   10.2226(14)
_cell_length_b                   12.3427(15)
_cell_length_c                   13.1761(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.860(3)
_cell_angle_gamma                90.00
_cell_volume                     1632.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5322
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.8

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_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 axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            25019
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.43
_reflns_number_total             3710
_reflns_number_gt                2282
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-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)+(0.0614P)²+0.6916P] 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         3710
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.7521(2) 0.18279(17) 0.20512(16) 0.0478(5) Uani 1 1 d . . .
C2 C 0.8496(3) 0.2440(2) 0.1739(2) 0.0700(7) Uani 1 1 d . . .
H2 H 0.9394 0.2316 0.2000 0.084 Uiso 1 1 calc R . .
C3 C 0.8094(3) 0.3239(2) 0.1028(2) 0.0805(9) Uani 1 1 d . . .
H3 H 0.8734 0.3665 0.0805 0.097 Uiso 1 1 calc R . .
C4 C 0.6787(3) 0.3428(2) 0.0639(2) 0.0727(8) Uani 1 1 d . . .
H4 H 0.6548 0.3982 0.0162 0.087 Uiso 1 1 calc R . .
C5 C 0.5801(3) 0.28013(19) 0.09488(17) 0.0602(6) Uani 1 1 d . . .
H5 H 0.4905 0.2926 0.0682 0.072 Uiso 1 1 calc R . .
C6 C 0.6188(2) 0.19910(16) 0.16609(15) 0.0442(5) Uani 1 1 d . . .
C7 C 0.53835(18) 0.12006(16) 0.21581(14) 0.0407(5) Uani 1 1 d . . .
C8 C 0.6481(2) 0.05774(17) 0.28920(15) 0.0440(5) Uani 1 1 d . . .
C9 C 0.8926(2) 0.0662(2) 0.34152(19) 0.0715(7) Uani 1 1 d . . .
H9A H 0.8762 0.0125 0.3904 0.107 Uiso 1 1 calc R . .
H9B H 0.9354 0.1279 0.3778 0.107 Uiso 1 1 calc R . .
H9C H 0.9491 0.0362 0.2982 0.107 Uiso 1 1 calc R . .
C10 C 0.4536(2) 0.17801(18) 0.28081(16) 0.0460(5) Uani 1 1 d . . .
C11 C 0.33138(19) 0.15003(16) 0.28853(14) 0.0403(4) Uani 1 1 d . . .
C12 C 0.2648(2) 0.05801(16) 0.22760(15) 0.0447(5) Uani 1 1 d . . .
C13 C 0.3517(2) -0.01880(17) 0.18039(16) 0.0471(5) Uani 1 1 d . . .
H13 H 0.3993 -0.0645 0.2361 0.056 Uiso 1 1 calc R . .
C14 C 0.4546(2) 0.04465(18) 0.13680(16) 0.0490(5) Uani 1 1 d . . .
H14A H 0.4098 0.0875 0.0788 0.059 Uiso 1 1 calc R . .
H14B H 0.5134 -0.0057 0.1109 0.059 Uiso 1 1 calc R . .
C15 C 0.2702(2) -0.09341(18) 0.10021(17) 0.0568(6) Uani 1 1 d . . .
H15A H 0.2245 -0.0510 0.0434 0.085 Uiso 1 1 calc R . .
H15B H 0.2064 -0.1322 0.1311 0.085 Uiso 1 1 calc R . .
H15C H 0.3285 -0.1440 0.0756 0.085 Uiso 1 1 calc R . .
C16 C 0.25465(19) 0.21337(16) 0.35436(15) 0.0410(5) Uani 1 1 d . . .
C17 C 0.2092(3) 0.31603(18) 0.32720(17) 0.0593(6) Uani 1 1 d . . .
H17 H 0.2288 0.3479 0.2679 0.071 Uiso 1 1 calc R . .
C18 C 0.1351(3) 0.3722(2) 0.38673(19) 0.0729(8) Uani 1 1 d . . .
H18 H 0.1017 0.4404 0.3657 0.087 Uiso 1 1 calc R . .
C19 C 0.1103(2) 0.3287(2) 0.47626(18) 0.0612(6) Uani 1 1 d . . .
H19 H 0.0609 0.3671 0.5167 0.073 Uiso 1 1 calc R . .
C20 C 0.1583(2) 0.2286(2) 0.50584(17) 0.0588(6) Uani 1 1 d . . .
H20 H 0.1433 0.1992 0.5676 0.071 Uiso 1 1 calc R . .
C21 C 0.2289(2) 0.17036(18) 0.44524(16) 0.0524(5) Uani 1 1 d . . .
H21 H 0.2597 0.1014 0.4657 0.063 Uiso 1 1 calc R . .
N1 N 0.76748(16) 0.09927(15) 0.27844(13) 0.0493(4) Uani 1 1 d . . .
O1 O 0.63234(16) -0.01570(13) 0.34651(12) 0.0613(4) Uani 1 1 d . . .
O2 O 0.14642(15) 0.04551(14) 0.21910(13) 0.0700(5) Uani 1 1 d . . .
H10 H 0.491(2) 0.2400(18) 0.3215(16) 0.053(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(3) . ?
C1 C6 1.378(3) . ?
C1 N1 1.401(3) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.503(3) . ?
C7 C10 1.509(3) . ?
C7 C14 1.532(3) . ?
C7 C8 1.542(3) . ?
C8 O1 1.210(2) . ?
C8 N1 1.355(3) . ?
C9 N1 1.446(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.319(3) . ?
C10 H10 0.97(2) . ?
C11 C12 1.480(3) . ?
C11 C16 1.495(3) . ?
C12 O2 1.204(2) . ?
C12 C13 1.511(3) . ?
C13 C14 1.509(3) . ?
C13 C15 1.525(3) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.373(3) . ?
C16 C21 1.380(3) . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.359(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(3) . ?
C20 H20 0.9300 . ?
C21 H21 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
C2 C1 C6 122.0(2) . . ?
C2 C1 N1 128.1(2) . . ?
C6 C1 N1 109.81(17) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C4 C3 C2 122.0(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 C7 131.1(2) . . ?
C1 C6 C7 109.05(18) . . ?
C6 C7 C10 111.06(17) . . ?
C6 C7 C14 112.32(16) . . ?
C10 C7 C14 111.49(16) . . ?
C6 C7 C8 101.77(15) . . ?
C10 C7 C8 107.97(15) . . ?
C14 C7 C8 111.76(17) . . ?
O1 C8 N1 125.3(2) . . ?
O1 C8 C7 126.74(18) . . ?
N1 C8 C7 107.99(17) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 125.00(19) . . ?
C11 C10 H10 116.6(12) . . ?
C7 C10 H10 118.4(12) . . ?
C10 C11 C12 120.30(18) . . ?
C10 C11 C16 121.07(18) . . ?
C12 C11 C16 118.56(16) . . ?
O2 C12 C11 119.99(18) . . ?
O2 C12 C13 122.67(19) . . ?
C11 C12 C13 117.32(17) . . ?
C14 C13 C12 109.69(17) . . ?
C14 C13 C15 112.24(17) . . ?
C12 C13 C15 112.19(18) . . ?
C14 C13 H13 107.5 . . ?
C12 C13 H13 107.5 . . ?
C15 C13 H13 107.5 . . ?
C13 C14 C7 113.41(16) . . ?
C13 C14 H14A 108.9 . . ?
C7 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C7 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.08(18) . . ?
C17 C16 C11 121.33(18) . . ?
C21 C16 C11 120.59(18) . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.6(2) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C8 N1 C1 111.38(17) . . ?
C8 N1 C9 123.29(19) . . ?
C1 N1 C9 125.16(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.9(3) . . . . ?
N1 C1 C2 C3 -178.0(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
N1 C1 C6 C5 177.93(17) . . . . ?
C2 C1 C6 C7 -179.76(19) . . . . ?
N1 C1 C6 C7 -0.7(2) . . . . ?
C5 C6 C7 C10 -63.3(3) . . . . ?
C1 C6 C7 C10 115.07(18) . . . . ?
C5 C6 C7 C14 62.3(3) . . . . ?
C1 C6 C7 C14 -119.30(19) . . . . ?
C5 C6 C7 C8 -178.0(2) . . . . ?
C1 C6 C7 C8 0.4(2) . . . . ?
C6 C7 C8 O1 -179.70(19) . . . . ?
C10 C7 C8 O1 63.3(3) . . . . ?
C14 C7 C8 O1 -59.6(2) . . . . ?
C6 C7 C8 N1 0.06(19) . . . . ?
C10 C7 C8 N1 -116.91(18) . . . . ?
C14 C7 C8 N1 120.12(17) . . . . ?
C6 C7 C10 C11 141.9(2) . . . . ?
C14 C7 C10 C11 15.8(3) . . . . ?
C8 C7 C10 C11 -107.3(2) . . . . ?
C7 C10 C11 C12 -2.5(3) . . . . ?
C7 C10 C11 C16 -179.40(18) . . . . ?
C10 C11 C12 O2 -165.7(2) . . . . ?
C16 C11 C12 O2 11.3(3) . . . . ?
C10 C11 C12 C13 15.8(3) . . . . ?
C16 C11 C12 C13 -167.20(17) . . . . ?
O2 C12 C13 C14 140.3(2) . . . . ?
C11 C12 C13 C14 -41.3(2) . . . . ?
O2 C12 C13 C15 14.8(3) . . . . ?
C11 C12 C13 C15 -166.74(18) . . . . ?
C12 C13 C14 C7 54.8(2) . . . . ?
C15 C13 C14 C7 -179.77(18) . . . . ?
C6 C7 C14 C13 -167.69(17) . . . . ?
C10 C7 C14 C13 -42.3(2) . . . . ?
C8 C7 C14 C13 78.6(2) . . . . ?
C10 C11 C16 C17 69.9(3) . . . . ?
C12 C11 C16 C17 -107.0(2) . . . . ?
C10 C11 C16 C21 -109.3(2) . . . . ?
C12 C11 C16 C21 73.8(3) . . . . ?
C21 C16 C17 C18 -2.9(4) . . . . ?
C11 C16 C17 C18 177.9(2) . . . . ?
C16 C17 C18 C19 2.8(4) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C18 C19 C20 C21 -1.4(4) . . . . ?
C19 C20 C21 C16 1.3(4) . . . . ?
C17 C16 C21 C20 0.8(3) . . . . ?
C11 C16 C21 C20 -180.0(2) . . . . ?
O1 C8 N1 C1 179.30(19) . . . . ?
C7 C8 N1 C1 -0.5(2) . . . . ?
O1 C8 N1 C9 -5.3(3) . . . . ?
C7 C8 N1 C9 174.91(19) . . . . ?
C2 C1 N1 C8 179.8(2) . . . . ?
C6 C1 N1 C8 0.7(2) . . . . ?
C2 C1 N1 C9 4.5(3) . . . . ?
C6 C1 N1 C9 -174.55(19) . . . . ?

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
C9 H9C O2 0.96 2.44 3.313(3) 150.9 1_655
C13 H13 O1 0.98 2.62 3.265(3) 123.8 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1035651'
_audit_update_record             
;
2014-11-24 deposited with the CCDC.
2015-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 I2 N O'
_chemical_formula_sum            'C21 H19 I2 N O'
_chemical_formula_weight         555.17

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'
I I -0.4742 1.8119 '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

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

_cell_length_a                   8.5479(3)
_cell_length_b                   10.8667(5)
_cell_length_c                   12.2056(6)
_cell_angle_alpha                109.155(3)
_cell_angle_beta                 101.187(2)
_cell_angle_gamma                100.463(2)
_cell_volume                     1013.16(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      31.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    3.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4029
_exptl_absorpt_correction_T_max  0.5799
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_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  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22501
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3984
_reflns_number_gt                3320
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-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)+(0.0261P)²+1.7945P] 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         3984
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.3339(5) 0.4434(4) 0.2486(3) 0.0458(9) Uani 1 1 d . . .
H1 H 0.3182 0.3556 0.2464 0.055 Uiso 1 1 calc R . .
C2 C 0.2000(5) 0.4921(5) 0.2175(4) 0.0551(11) Uani 1 1 d . . .
H2 H 0.0931 0.4369 0.1950 0.066 Uiso 1 1 calc R . .
C3 C 0.2239(5) 0.6206(5) 0.2198(4) 0.0550(11) Uani 1 1 d . . .
H3 H 0.1323 0.6511 0.1979 0.066 Uiso 1 1 calc R . .
C4 C 0.3787(6) 0.7061(5) 0.2532(4) 0.0529(10) Uani 1 1 d . . .
H4 H 0.3939 0.7936 0.2547 0.063 Uiso 1 1 calc R . .
C5 C 0.5120(5) 0.6565(4) 0.2847(3) 0.0408(8) Uani 1 1 d . . .
C6 C 0.4899(4) 0.5272(4) 0.2825(3) 0.0358(8) Uani 1 1 d . . .
C7 C 0.6571(4) 0.5047(3) 0.3227(3) 0.0339(7) Uani 1 1 d . . .
C8 C 0.7742(5) 0.6420(4) 0.3493(3) 0.0418(8) Uani 1 1 d . . .
C9 C 0.7480(7) 0.8629(5) 0.3422(6) 0.0785(15) Uani 1 1 d . . .
H9A H 0.6599 0.9002 0.3180 0.118 Uiso 1 1 calc R . .
H9B H 0.8248 0.8680 0.2950 0.118 Uiso 1 1 calc R . .
H9C H 0.8039 0.9132 0.4260 0.118 Uiso 1 1 calc R . .
C10 C 0.6836(5) 0.4660(4) 0.4351(3) 0.0388(8) Uani 1 1 d . . .
H10A H 0.7500 0.5437 0.5061 0.047 Uiso 1 1 calc R . .
H10B H 0.5780 0.4345 0.4486 0.047 Uiso 1 1 calc R . .
C11 C 0.7724(4) 0.3537(3) 0.4105(3) 0.0335(7) Uani 1 1 d . . .
H11 H 0.8897 0.3954 0.4535 0.040 Uiso 1 1 calc R . .
C12 C 0.7586(4) 0.3084(3) 0.2766(3) 0.0328(7) Uani 1 1 d . . .
C13 C 0.6988(4) 0.3917(4) 0.2328(3) 0.0350(7) Uani 1 1 d . . .
C14 C 0.7129(4) 0.2437(4) 0.4538(3) 0.0422(8) Uani 1 1 d . . .
H14A H 0.7269 0.2834 0.5400 0.051 Uiso 1 1 calc R . .
H14B H 0.7808 0.1807 0.4401 0.051 Uiso 1 1 calc R . .
C15 C 0.8108(4) 0.1880(3) 0.2154(3) 0.0343(7) Uani 1 1 d . . .
C16 C 0.7157(5) 0.0900(4) 0.1069(4) 0.0505(10) Uani 1 1 d . . .
H16 H 0.6185 0.1025 0.0679 0.061 Uiso 1 1 calc R . .
C17 C 0.7608(5) -0.0262(4) 0.0545(4) 0.0598(12) Uani 1 1 d . . .
H17 H 0.6933 -0.0904 -0.0188 0.072 Uiso 1 1 calc R . .
C18 C 0.9031(5) -0.0497(4) 0.1080(4) 0.0501(10) Uani 1 1 d . . .
C19 C 0.9984(5) 0.0483(4) 0.2158(4) 0.0525(10) Uani 1 1 d . . .
H19 H 1.0962 0.0358 0.2538 0.063 Uiso 1 1 calc R . .
C20 C 0.9543(4) 0.1651(4) 0.2701(4) 0.0442(9) Uani 1 1 d . . .
H20 H 1.0215 0.2287 0.3438 0.053 Uiso 1 1 calc R . .
C21 C 0.9499(7) -0.1784(5) 0.0523(5) 0.0787(16) Uani 1 1 d . . .
H21A H 0.8686 -0.2341 -0.0225 0.118 Uiso 1 1 calc R . .
H21B H 0.9549 -0.2259 0.1062 0.118 Uiso 1 1 calc R . .
H21C H 1.0560 -0.1575 0.0376 0.118 Uiso 1 1 calc R . .
N1 N 0.6803(4) 0.7228(3) 0.3236(3) 0.0456(8) Uani 1 1 d . . .
O1 O 0.9229(3) 0.6741(3) 0.3883(3) 0.0603(8) Uani 1 1 d . . .
I1 I 0.67674(4) 0.39135(3) 0.05988(2) 0.05826(11) Uani 1 1 d . . .
I2 I 0.45874(4) 0.13531(3) 0.36582(3) 0.06821(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
C1 C6 1.369(5) . ?
C1 C2 1.384(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.365(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(5) . ?
C5 N1 1.396(5) . ?
C6 C7 1.509(5) . ?
C7 C13 1.505(5) . ?
C7 C8 1.532(5) . ?
C7 C10 1.549(5) . ?
C8 O1 1.208(4) . ?
C8 N1 1.361(5) . ?
C9 N1 1.451(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.530(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C14 1.505(5) . ?
C11 C12 1.517(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.322(5) . ?
C12 C15 1.472(5) . ?
C13 I1 2.082(3) . ?
C14 I2 2.144(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.375(5) . ?
C15 C20 1.384(5) . ?
C16 C17 1.376(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(6) . ?
C18 C21 1.505(6) . ?
C19 C20 1.382(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C6 C1 C2 118.7(4) . . ?
C6 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 122.0(4) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 117.2(4) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C6 C5 C4 121.5(4) . . ?
C6 C5 N1 110.0(3) . . ?
C4 C5 N1 128.5(4) . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 C7 131.0(3) . . ?
C5 C6 C7 108.7(3) . . ?
C13 C7 C6 115.7(3) . . ?
C13 C7 C8 111.5(3) . . ?
C6 C7 C8 102.1(3) . . ?
C13 C7 C10 101.7(3) . . ?
C6 C7 C10 115.2(3) . . ?
C8 C7 C10 110.9(3) . . ?
O1 C8 N1 125.9(4) . . ?
O1 C8 C7 126.3(3) . . ?
N1 C8 C7 107.7(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 107.2(3) . . ?
C11 C10 H10A 110.3 . . ?
C7 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
C7 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
C14 C11 C12 115.7(3) . . ?
C14 C11 C10 114.4(3) . . ?
C12 C11 C10 104.3(3) . . ?
C14 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C10 C11 H11 107.3 . . ?
C13 C12 C15 129.7(3) . . ?
C13 C12 C11 110.0(3) . . ?
C15 C12 C11 120.3(3) . . ?
C12 C13 C7 115.0(3) . . ?
C12 C13 I1 126.8(2) . . ?
C7 C13 I1 117.9(2) . . ?
C11 C14 I2 113.1(2) . . ?
C11 C14 H14A 109.0 . . ?
I2 C14 H14A 109.0 . . ?
C11 C14 H14B 109.0 . . ?
I2 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C20 117.2(3) . . ?
C16 C15 C12 122.3(3) . . ?
C20 C15 C12 120.4(3) . . ?
C15 C16 C17 121.6(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 121.6(4) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C19 C18 C17 116.8(4) . . ?
C19 C18 C21 121.7(4) . . ?
C17 C18 C21 121.5(4) . . ?
C18 C19 C20 122.3(4) . . ?
C18 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C19 C20 C15 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
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 . . ?
C8 N1 C5 111.5(3) . . ?
C8 N1 C9 123.6(4) . . ?
C5 N1 C9 124.8(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 0.6(6) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C3 C4 C5 N1 -178.8(4) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C2 C1 C6 C7 178.8(4) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
N1 C5 C6 C1 179.2(3) . . . . ?
C4 C5 C6 C7 -179.3(3) . . . . ?
N1 C5 C6 C7 -0.3(4) . . . . ?
C1 C6 C7 C13 60.3(5) . . . . ?
C5 C6 C7 C13 -120.4(3) . . . . ?
C1 C6 C7 C8 -178.4(4) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C1 C6 C7 C10 -58.2(5) . . . . ?
C5 C6 C7 C10 121.2(3) . . . . ?
C13 C7 C8 O1 -58.4(5) . . . . ?
C6 C7 C8 O1 177.5(4) . . . . ?
C10 C7 C8 O1 54.3(5) . . . . ?
C13 C7 C8 N1 122.9(3) . . . . ?
C6 C7 C8 N1 -1.3(4) . . . . ?
C10 C7 C8 N1 -124.5(3) . . . . ?
C13 C7 C10 C11 11.9(3) . . . . ?
C6 C7 C10 C11 137.8(3) . . . . ?
C8 C7 C10 C11 -106.9(3) . . . . ?
C7 C10 C11 C14 -140.3(3) . . . . ?
C7 C10 C11 C12 -12.9(4) . . . . ?
C14 C11 C12 C13 135.6(3) . . . . ?
C10 C11 C12 C13 9.0(4) . . . . ?
C14 C11 C12 C15 -45.1(4) . . . . ?
C10 C11 C12 C15 -171.8(3) . . . . ?
C15 C12 C13 C7 179.5(3) . . . . ?
C11 C12 C13 C7 -1.3(4) . . . . ?
C15 C12 C13 I1 -6.1(6) . . . . ?
C11 C12 C13 I1 173.0(2) . . . . ?
C6 C7 C13 C12 -132.4(3) . . . . ?
C8 C7 C13 C12 111.6(3) . . . . ?
C10 C7 C13 C12 -6.8(4) . . . . ?
C6 C7 C13 I1 52.7(4) . . . . ?
C8 C7 C13 I1 -63.4(3) . . . . ?
C10 C7 C13 I1 178.3(2) . . . . ?
C12 C11 C14 I2 -58.5(3) . . . . ?
C10 C11 C14 I2 62.8(3) . . . . ?
C13 C12 C15 C16 -47.2(6) . . . . ?
C11 C12 C15 C16 133.7(4) . . . . ?
C13 C12 C15 C20 137.3(4) . . . . ?
C11 C12 C15 C20 -41.8(5) . . . . ?
C20 C15 C16 C17 0.0(6) . . . . ?
C12 C15 C16 C17 -175.7(4) . . . . ?
C15 C16 C17 C18 -0.1(8) . . . . ?
C16 C17 C18 C19 -0.2(7) . . . . ?
C16 C17 C18 C21 178.3(5) . . . . ?
C17 C18 C19 C20 0.7(7) . . . . ?
C21 C18 C19 C20 -177.8(4) . . . . ?
C18 C19 C20 C15 -0.9(7) . . . . ?
C16 C15 C20 C19 0.5(6) . . . . ?
C12 C15 C20 C19 176.3(4) . . . . ?
O1 C8 N1 C5 -177.6(4) . . . . ?
C7 C8 N1 C5 1.2(4) . . . . ?
O1 C8 N1 C9 -1.3(7) . . . . ?
C7 C8 N1 C9 177.4(4) . . . . ?
C6 C5 N1 C8 -0.6(4) . . . . ?
C4 C5 N1 C8 178.3(4) . . . . ?
C6 C5 N1 C9 -176.8(4) . . . . ?
C4 C5 N1 C9 2.1(6) . . . . ?

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
C9 H9A I2 0.96 3.29 4.163(5) 152.1 1_565
C11 H11 O1 0.98 2.66 3.346(4) 127.5 2_766

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.847
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.079
