# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 1012693'
_audit_update_record             
;
2014-07-07 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N O'
_chemical_formula_weight         285.33

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

_cell_length_a                   13.099(17)
_cell_length_b                   9.359(12)
_cell_length_c                   24.26(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2974(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    538
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      28.26

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9822
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   ?

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6636
_diffrn_reflns_av_R_equivalents  0.1314
_diffrn_reflns_av_sigmaI/netI    0.1821
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2556
_reflns_number_gt                891
_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)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2556
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2492
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.2581(4) 0.0490(6) 0.2316(2) 0.0539(15) Uani 1 1 d . . .
H1 H 0.3276 0.0612 0.2379 0.065 Uiso 1 1 calc R . .
C2 C 0.2262(5) -0.0469(6) 0.1917(2) 0.0623(16) Uani 1 1 d . . .
H2 H 0.2743 -0.0974 0.1713 0.075 Uiso 1 1 calc R . .
C3 C 0.1239(5) -0.0677(6) 0.1820(2) 0.0717(18) Uani 1 1 d . . .
H3 H 0.1022 -0.1331 0.1556 0.086 Uiso 1 1 calc R . .
C4 C 0.0552(5) 0.0091(6) 0.2116(3) 0.090(2) Uani 1 1 d . . .
H4 H -0.0141 -0.0037 0.2050 0.108 Uiso 1 1 calc R . .
C5 C 0.0862(4) 0.1063(6) 0.2515(2) 0.0697(18) Uani 1 1 d . . .
H5 H 0.0376 0.1578 0.2712 0.084 Uiso 1 1 calc R . .
C6 C 0.1887(4) 0.1269(5) 0.26219(19) 0.0418(14) Uani 1 1 d . . .
C7 C 0.2215(4) 0.2275(5) 0.3068(2) 0.0430(13) Uani 1 1 d . . .
C8 C 0.3232(4) 0.2554(5) 0.3166(2) 0.0483(15) Uani 1 1 d . . .
H8 H 0.3713 0.2094 0.2947 0.058 Uiso 1 1 calc R . .
C9 C 0.3589(5) 0.3491(6) 0.3577(2) 0.0586(16) Uani 1 1 d . . .
C10 C 0.2817(5) 0.4107(6) 0.3859(2) 0.0507(15) Uani 1 1 d . . .
C11 C 0.1796(4) 0.3813(5) 0.3754(2) 0.0444(14) Uani 1 1 d . . .
C12 C 0.1244(4) 0.4676(5) 0.4133(2) 0.0523(15) Uani 1 1 d . . .
H12 H 0.0537 0.4711 0.4165 0.063 Uiso 1 1 calc R . .
C13 C 0.1904(5) 0.5427(6) 0.4434(2) 0.0514(15) Uani 1 1 d . . .
C14 C 0.1823(5) 0.6479(6) 0.4880(2) 0.0543(15) Uani 1 1 d . . .
C15 C 0.2661(5) 0.7024(6) 0.5149(2) 0.0629(16) Uani 1 1 d . . .
H15 H 0.3311 0.6710 0.5052 0.075 Uiso 1 1 calc R . .
C16 C 0.2552(5) 0.8028(6) 0.5562(2) 0.0718(18) Uani 1 1 d . . .
H16 H 0.3126 0.8399 0.5736 0.086 Uiso 1 1 calc R . .
C17 C 0.1596(5) 0.8482(6) 0.5715(2) 0.0697(18) Uani 1 1 d . . .
H17 H 0.1526 0.9164 0.5991 0.084 Uiso 1 1 calc R . .
C18 C 0.0751(5) 0.7936(6) 0.5463(2) 0.079(2) Uani 1 1 d . . .
H18 H 0.0105 0.8235 0.5573 0.094 Uiso 1 1 calc R . .
C19 C 0.0849(5) 0.6938(6) 0.5044(2) 0.0715(18) Uani 1 1 d . . .
H19 H 0.0271 0.6574 0.4872 0.086 Uiso 1 1 calc R . .
C20 C 0.4710(4) 0.3792(6) 0.3686(2) 0.086(2) Uani 1 1 d . . .
H20A H 0.4866 0.4755 0.3579 0.128 Uiso 1 1 calc R . .
H20B H 0.5121 0.3141 0.3476 0.128 Uiso 1 1 calc R . .
H20C H 0.4851 0.3671 0.4072 0.128 Uiso 1 1 calc R . .
N1 N 0.1457(3) 0.2910(4) 0.33601(16) 0.0470(12) Uani 1 1 d . . .
O2 O 0.2903(3) 0.5082(4) 0.42862(14) 0.0567(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 C6 1.382(6) . ?
C1 C2 1.384(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(6) . ?
C7 N1 1.357(5) . ?
C7 C8 1.379(6) . ?
C8 C9 1.409(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.350(6) . ?
C9 C20 1.518(7) . ?
C10 O2 1.385(6) . ?
C10 C11 1.389(6) . ?
C11 N1 1.351(6) . ?
C11 C12 1.421(6) . ?
C12 C13 1.333(6) . ?
C12 H12 0.9300 . ?
C13 O2 1.395(6) . ?
C13 C14 1.467(7) . ?
C14 C15 1.376(6) . ?
C14 C19 1.403(7) . ?
C15 C16 1.380(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(7) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 121.3(5) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 120.3(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 118.8(6) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 121.5(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 117.8(5) . . ?
C5 C6 C7 120.1(5) . . ?
C1 C6 C7 122.1(5) . . ?
N1 C7 C8 122.3(5) . . ?
N1 C7 C6 116.3(5) . . ?
C8 C7 C6 121.4(5) . . ?
C7 C8 C9 124.1(5) . . ?
C7 C8 H8 117.9 . . ?
C9 C8 H8 117.9 . . ?
C10 C9 C8 112.1(5) . . ?
C10 C9 C20 123.9(5) . . ?
C8 C9 C20 124.0(5) . . ?
C9 C10 O2 126.8(6) . . ?
C9 C10 C11 122.9(5) . . ?
O2 C10 C11 110.2(5) . . ?
N1 C11 C10 124.8(5) . . ?
N1 C11 C12 130.2(6) . . ?
C10 C11 C12 105.0(5) . . ?
C13 C12 C11 108.9(5) . . ?
C13 C12 H12 125.6 . . ?
C11 C12 H12 125.6 . . ?
C12 C13 O2 110.2(5) . . ?
C12 C13 C14 135.4(6) . . ?
O2 C13 C14 114.4(5) . . ?
C15 C14 C19 118.5(5) . . ?
C15 C14 C13 122.7(6) . . ?
C19 C14 C13 118.8(6) . . ?
C14 C15 C16 120.9(6) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.1(6) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.3(6) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.3(6) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.9(6) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 N1 C7 113.8(4) . . ?
C10 O2 C13 105.6(4) . . ?

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 -0.7(8) . . . . ?
C1 C2 C3 C4 1.1(9) . . . . ?
C2 C3 C4 C5 -0.6(10) . . . . ?
C3 C4 C5 C6 -0.2(9) . . . . ?
C4 C5 C6 C1 0.6(8) . . . . ?
C4 C5 C6 C7 -177.6(5) . . . . ?
C2 C1 C6 C5 -0.2(8) . . . . ?
C2 C1 C6 C7 178.0(5) . . . . ?
C5 C6 C7 N1 2.0(6) . . . . ?
C1 C6 C7 N1 -176.1(4) . . . . ?
C5 C6 C7 C8 -176.9(5) . . . . ?
C1 C6 C7 C8 5.0(7) . . . . ?
N1 C7 C8 C9 1.0(8) . . . . ?
C6 C7 C8 C9 179.8(5) . . . . ?
C7 C8 C9 C10 -1.1(7) . . . . ?
C7 C8 C9 C20 179.8(5) . . . . ?
C8 C9 C10 O2 -179.6(5) . . . . ?
C20 C9 C10 O2 -0.5(8) . . . . ?
C8 C9 C10 C11 1.1(7) . . . . ?
C20 C9 C10 C11 -179.8(5) . . . . ?
C9 C10 C11 N1 -1.0(8) . . . . ?
O2 C10 C11 N1 179.6(4) . . . . ?
C9 C10 C11 C12 -179.7(5) . . . . ?
O2 C10 C11 C12 0.9(5) . . . . ?
N1 C11 C12 C13 -178.2(5) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 O2 -1.6(6) . . . . ?
C11 C12 C13 C14 179.9(5) . . . . ?
C12 C13 C14 C15 175.2(6) . . . . ?
O2 C13 C14 C15 -3.2(7) . . . . ?
C12 C13 C14 C19 -4.0(9) . . . . ?
O2 C13 C14 C19 177.5(4) . . . . ?
C19 C14 C15 C16 -1.7(8) . . . . ?
C13 C14 C15 C16 179.0(5) . . . . ?
C14 C15 C16 C17 1.0(9) . . . . ?
C15 C16 C17 C18 0.5(9) . . . . ?
C16 C17 C18 C19 -1.2(9) . . . . ?
C17 C18 C19 C14 0.5(8) . . . . ?
C15 C14 C19 C18 1.0(8) . . . . ?
C13 C14 C19 C18 -179.7(5) . . . . ?
C10 C11 N1 C7 0.7(7) . . . . ?
C12 C11 N1 C7 179.0(5) . . . . ?
C8 C7 N1 C11 -0.7(6) . . . . ?
C6 C7 N1 C11 -179.6(4) . . . . ?
C9 C10 O2 C13 178.8(5) . . . . ?
C11 C10 O2 C13 -1.9(5) . . . . ?
C12 C13 O2 C10 2.1(5) . . . . ?
C14 C13 O2 C10 -179.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.923
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_xianglikui0408
_database_code_depnum_ccdc_archive 'CCDC 1032635'
_audit_update_record             
;
2014-11-04 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;
_audit_creation_date             2014-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H14 I N O'
_chemical_formula_sum            'C20 H14 I N O'
_chemical_formula_weight         411.22
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.4452(3)
_cell_length_b                   19.3722(6)
_cell_length_c                   11.2423(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.073(4)
_cell_angle_gamma                90.00
_cell_volume                     1621.19(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2609
_cell_measurement_temperature    294.64(10)
_cell_measurement_theta_max      26.8140
_cell_measurement_theta_min      3.4490
_exptl_absorpt_coefficient_mu    1.979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6383
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      294.64(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0875661000
_diffrn_orient_matrix_UB_12      0.0057308000
_diffrn_orient_matrix_UB_13      0.0238363000
_diffrn_orient_matrix_UB_21      0.0357342000
_diffrn_orient_matrix_UB_22      -0.0023997000
_diffrn_orient_matrix_UB_23      -0.0578951000
_diffrn_orient_matrix_UB_31      -0.0115413000
_diffrn_orient_matrix_UB_32      0.0361014000
_diffrn_orient_matrix_UB_33      -0.0076595000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2472
_reflns_number_total             3186
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0377P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0981
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C4(H4), C1(H1), C2(H2), C5(H5), C8(H8), C17(H17), C3(H3), C15(H15),
 C24(H24), C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
I1 I 0.23372(4) 0.494584(13) 0.62289(3) 0.05563(14) Uani 1 d . . .
C9 C 0.2740(5) 0.49378(15) 1.1112(3) 0.0327(8) Uani 1 d . . .
O1 O 0.1764(3) 0.58354(10) 0.9686(2) 0.0363(6) Uani 1 d . . .
C16 C -0.0407(5) 0.7179(2) 0.6385(4) 0.0491(10) Uani 1 d . . .
H16 H -0.1024 0.7198 0.5659 0.059 Uiso 1 calc . . R
N1 N 0.3148(4) 0.41299(13) 0.8976(3) 0.0335(7) Uani 1 d . . .
C12 C 0.2104(5) 0.52366(17) 0.7990(3) 0.0337(8) Uani 1 d . . .
C4 C 0.4029(5) 0.20068(17) 1.1029(4) 0.0432(10) Uani 1 d . . .
H4 H 0.3702 0.1727 1.1661 0.052 Uiso 1 calc . . R
C1 C 0.4958(5) 0.28394(18) 0.9149(4) 0.0407(9) Uani 1 d . . .
H1 H 0.5275 0.3116 0.8510 0.049 Uiso 1 calc . . R
C2 C 0.5410(5) 0.21461(18) 0.9151(4) 0.0453(10) Uani 1 d . . .
H2 H 0.6026 0.1959 0.8515 0.054 Uiso 1 calc . . R
C10 C 0.2359(5) 0.51848(16) 0.9988(3) 0.0322(8) Uani 1 d . . .
C7 C 0.3485(4) 0.38674(15) 1.0060(3) 0.0322(8) Uani 1 d . . .
C11 C 0.2589(4) 0.47892(17) 0.8962(3) 0.0303(8) Uani 1 d . . .
C5 C 0.3585(5) 0.27021(16) 1.1031(3) 0.0381(9) Uani 1 d . . .
H5 H 0.2976 0.2886 1.1672 0.046 Uiso 1 calc . . R
C14 C 0.1026(5) 0.65101(17) 0.7952(3) 0.0357(8) Uani 1 d . . .
C8 C 0.3307(4) 0.42510(16) 1.1111(3) 0.0346(8) Uani 1 d . . .
H8 H 0.3577 0.4039 1.1835 0.042 Uiso 1 calc . . R
C17 C 0.0019(6) 0.7779(2) 0.6989(4) 0.0528(11) Uani 1 d . . .
H17 H -0.0302 0.8203 0.6662 0.063 Uiso 1 calc . . R
C3 C 0.4947(5) 0.1731(2) 1.0098(4) 0.0495(11) Uani 1 d . . .
H3 H 0.5258 0.1266 1.0103 0.059 Uiso 1 calc . . R
C13 C 0.1610(4) 0.58493(17) 0.8453(3) 0.0340(8) Uani 1 d . . .
C6 C 0.4035(5) 0.31247(16) 1.0091(3) 0.0329(8) Uani 1 d . . .
C15 C 0.0092(5) 0.65488(19) 0.6869(3) 0.0410(9) Uani 1 d . . .
H15 H -0.0202 0.6144 0.6464 0.049 Uiso 1 calc . . R
C19 C 0.2575(5) 0.53649(19) 1.2214(3) 0.0460(10) Uani 1 d . . .
H19A H 0.3566 0.5681 1.2271 0.069 Uiso 1 calc . . GR
H19B H 0.2586 0.5069 1.2898 0.069 Uiso 1 calc . . GR
H19C H 0.1469 0.5619 1.2179 0.069 Uiso 1 calc . . GR
C24 C 0.1412(5) 0.71231(17) 0.8557(4) 0.0425(9) Uani 1 d . . .
H24 H 0.2006 0.7110 0.9292 0.051 Uiso 1 calc . . R
C18 C 0.0908(5) 0.77553(18) 0.8063(4) 0.0472(10) Uani 1 d . . .
H18 H 0.1178 0.8163 0.8465 0.057 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C12 2.069(4) . ?
C9 C10 1.376(5) . ?
C9 C8 1.396(4) . ?
C9 C19 1.496(5) . ?
O1 C10 1.376(4) . ?
O1 C13 1.390(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(6) . ?
C16 C15 1.385(5) . ?
N1 C7 1.339(4) . ?
N1 C11 1.343(4) . ?
C12 C11 1.436(5) . ?
C12 C13 1.350(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(4) . ?
C4 C3 1.369(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(5) . ?
C1 C6 1.388(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(5) . ?
C10 C11 1.399(5) . ?
C7 C8 1.405(5) . ?
C7 C6 1.496(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(5) . ?
C14 C13 1.461(4) . ?
C14 C15 1.393(5) . ?
C14 C24 1.396(5) . ?
C8 H8 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.367(6) . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C24 H24 0.9300 . ?
C24 C18 1.393(5) . ?
C18 H18 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
C10 C9 C8 112.8(3) . . ?
C10 C9 C19 123.3(3) . . ?
C8 C9 C19 123.9(3) . . ?
C10 O1 C13 106.5(3) . . ?
C17 C16 H16 120.3 . . ?
C17 C16 C15 119.4(4) . . ?
C15 C16 H16 120.3 . . ?
C7 N1 C11 115.1(3) . . ?
C11 C12 I1 122.7(3) . . ?
C13 C12 I1 129.5(3) . . ?
C13 C12 C11 107.7(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(4) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(4) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(4) . . ?
C3 C2 H2 119.9 . . ?
C9 C10 C11 122.7(3) . . ?
O1 C10 C9 127.2(3) . . ?
O1 C10 C11 110.0(3) . . ?
N1 C7 C8 123.1(3) . . ?
N1 C7 C6 115.7(3) . . ?
C8 C7 C6 121.3(3) . . ?
N1 C11 C12 131.1(3) . . ?
N1 C11 C10 123.6(3) . . ?
C10 C11 C12 105.3(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C15 C14 C13 121.6(3) . . ?
C15 C14 C24 118.4(3) . . ?
C24 C14 C13 120.1(4) . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.7 . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O1 C13 C14 114.8(3) . . ?
C12 C13 O1 110.5(3) . . ?
C12 C13 C14 134.7(3) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 121.1(3) . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C24 H24 119.9 . . ?
C18 C24 C14 120.1(4) . . ?
C18 C24 H24 119.9 . . ?
C17 C18 C24 120.3(4) . . ?
C17 C18 H18 119.9 . . ?
C24 C18 H18 119.9 . . ?

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
I1 C12 C11 N1 -4.2(5) . . . . ?
I1 C12 C11 C10 176.0(2) . . . . ?
I1 C12 C13 O1 -175.5(2) . . . . ?
I1 C12 C13 C14 2.0(6) . . . . ?
C9 C10 C11 N1 2.0(5) . . . . ?
C9 C10 C11 C12 -178.2(3) . . . . ?
O1 C10 C11 N1 -179.6(3) . . . . ?
O1 C10 C11 C12 0.2(4) . . . . ?
C16 C17 C18 C24 0.6(6) . . . . ?
N1 C7 C8 C9 0.8(5) . . . . ?
N1 C7 C6 C1 30.0(5) . . . . ?
N1 C7 C6 C5 -147.6(3) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C4 C5 C6 C7 177.1(3) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C2 C1 C6 C7 -177.5(4) . . . . ?
C2 C1 C6 C5 0.2(6) . . . . ?
C10 C9 C8 C7 0.9(5) . . . . ?
C10 O1 C13 C12 -0.6(4) . . . . ?
C10 O1 C13 C14 -178.7(3) . . . . ?
C7 N1 C11 C12 -179.8(3) . . . . ?
C7 N1 C11 C10 -0.2(5) . . . . ?
C11 N1 C7 C8 -1.2(5) . . . . ?
C11 N1 C7 C6 177.6(3) . . . . ?
C11 C12 C13 O1 0.8(4) . . . . ?
C11 C12 C13 C14 178.3(4) . . . . ?
C5 C4 C3 C2 -0.9(6) . . . . ?
C14 C24 C18 C17 0.6(6) . . . . ?
C8 C9 C10 O1 179.6(3) . . . . ?
C8 C9 C10 C11 -2.3(5) . . . . ?
C8 C7 C6 C1 -151.3(3) . . . . ?
C8 C7 C6 C5 31.2(5) . . . . ?
C17 C16 C15 C14 -0.4(6) . . . . ?
C3 C4 C5 C6 0.9(6) . . . . ?
C13 O1 C10 C9 178.6(4) . . . . ?
C13 O1 C10 C11 0.3(4) . . . . ?
C13 C12 C11 N1 179.2(3) . . . . ?
C13 C12 C11 C10 -0.6(4) . . . . ?
C13 C14 C15 C16 -178.0(3) . . . . ?
C13 C14 C24 C18 177.9(3) . . . . ?
C6 C1 C2 C3 -0.1(6) . . . . ?
C6 C7 C8 C9 -177.9(3) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C15 C14 C13 O1 -152.2(3) . . . . ?
C15 C14 C13 C12 30.3(6) . . . . ?
C15 C14 C24 C18 -1.7(5) . . . . ?
C19 C9 C10 O1 -0.8(6) . . . . ?
C19 C9 C10 C11 177.3(3) . . . . ?
C19 C9 C8 C7 -178.6(3) . . . . ?
C24 C14 C13 O1 28.2(4) . . . . ?
C24 C14 C13 C12 -149.2(4) . . . . ?
C24 C14 C15 C16 1.6(5) . . . . ?

