# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_av73
_database_code_depnum_ccdc_archive 'CCDC 1051824'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 N O5'
_chemical_formula_sum            'C17 H19 N O5'
_chemical_formula_weight         317.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.6571(12)
_cell_length_b                   7.7611(7)
_cell_length_c                   14.9680(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.630(2)
_cell_angle_gamma                90
_cell_volume                     1585.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1366
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      19.58

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14739
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_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         1.991
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2794
_reflns_number_gt                2100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL-2014/7

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+1.3664P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2794
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0975
_refine_ls_wR_factor_ref         0.1823
_refine_ls_wR_factor_gt          0.1684
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_restrained_S_all      1.242
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7880(3) 1.0954(5) 0.2946(2) 0.0393(9) Uani 1 1 d . . . . .
C2 C 0.9533(3) 1.1401(6) 0.2977(3) 0.0554(12) Uani 1 1 d . . . . .
H2A H 0.9892 1.2479 0.3012 0.066 Uiso 1 1 calc R U . . .
H2B H 0.9942 1.0540 0.2704 0.066 Uiso 1 1 calc R U . . .
C3 C 0.9245(3) 1.0826(6) 0.3900(3) 0.0530(11) Uani 1 1 d . . . . .
H3A H 0.9609 0.9811 0.4090 0.064 Uiso 1 1 calc R U . . .
H3B H 0.9350 1.1735 0.4337 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8172(3) 1.0430(5) 0.3767(2) 0.0410(10) Uani 1 1 d . . . . .
C5 C 0.6913(3) 1.0983(5) 0.2481(2) 0.0389(9) Uani 1 1 d . . . . .
C6 C 0.6089(3) 1.1444(5) 0.2950(3) 0.0488(10) Uani 1 1 d . . . . .
H6 H 0.6160 1.1704 0.3554 0.059 Uiso 1 1 calc R U . . .
C7 C 0.5177(3) 1.1527(6) 0.2548(3) 0.0568(12) Uani 1 1 d . . . . .
H7 H 0.4636 1.1821 0.2880 0.068 Uiso 1 1 calc R U . . .
C8 C 0.5068(3) 1.1169(6) 0.1648(3) 0.0571(12) Uani 1 1 d . . . . .
H8 H 0.4451 1.1229 0.1371 0.069 Uiso 1 1 calc R U . . .
C9 C 0.5871(3) 1.0723(5) 0.1156(3) 0.0517(11) Uani 1 1 d . . . . .
H9 H 0.5794 1.0505 0.0547 0.062 Uiso 1 1 calc R U . . .
C10 C 0.6791(3) 1.0599(5) 0.1564(2) 0.0410(10) Uani 1 1 d . . . . .
C11 C 0.7628(3) 0.9575(5) 0.4434(2) 0.0442(10) Uani 1 1 d . . . . .
H11 H 0.6978 0.9295 0.4300 0.053 Uiso 1 1 calc R U . . .
C12 C 0.7997(3) 0.9151(6) 0.5243(3) 0.0515(11) Uani 1 1 d . . . . .
H12 H 0.8631 0.9508 0.5392 0.062 Uiso 1 1 calc R U . . .
C13 C 0.7473(3) 0.8175(6) 0.5897(2) 0.0477(10) Uani 1 1 d . . . . .
C14 C 0.7663(4) 0.6618(7) 0.7244(3) 0.0730(15) Uani 1 1 d . . . . .
H14A H 0.7196 0.7233 0.7589 0.109 Uiso 1 1 calc R U . . .
H14B H 0.8179 0.6191 0.7633 0.109 Uiso 1 1 calc R U . . .
H14C H 0.7345 0.5669 0.6944 0.109 Uiso 1 1 calc R U . . .
C15 C 0.7672(3) 0.9381(5) 0.0271(3) 0.0490(11) Uani 1 1 d . . . . .
C16 C 0.8854(4) 0.8278(8) -0.0710(3) 0.096(2) Uani 1 1 d . . . . .
H16A H 0.8303 0.7622 -0.0950 0.116 Uiso 1 1 calc R U . . .
H16B H 0.8978 0.9217 -0.1119 0.116 Uiso 1 1 calc R U . . .
C17 C 0.9680(4) 0.7214(8) -0.0649(3) 0.0903(18) Uani 1 1 d . . . . .
H17A H 1.0239 0.7882 -0.0457 0.135 Uiso 1 1 calc R U . . .
H17B H 0.9798 0.6718 -0.1224 0.135 Uiso 1 1 calc R U . . .
H17C H 0.9571 0.6311 -0.0225 0.135 Uiso 1 1 calc R U . . .
N1 N 0.7616(3) 1.0101(5) 0.1094(2) 0.0483(9) Uani 1 1 d . . . . .
H1N H 0.816(2) 1.028(4) 0.135(2) 0.030(10) Uiso 1 1 d . . . . .
O1 O 0.86257(18) 1.1621(4) 0.24614(16) 0.0498(7) Uani 1 1 d . . . . .
O2 O 0.6630(2) 0.7747(4) 0.5849(2) 0.0682(10) Uani 1 1 d . . . . .
O3 O 0.8064(2) 0.7744(4) 0.65999(18) 0.0601(9) Uani 1 1 d . . . . .
O4 O 0.7014(2) 0.9117(4) -0.02527(19) 0.0677(9) Uani 1 1 d . . . . .
O5 O 0.8610(2) 0.8973(4) 0.01469(17) 0.0615(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.344(5) . ?
C1 O1 1.368(4) . ?
C1 C5 1.476(5) . ?
C2 O1 1.451(4) . ?
C2 C3 1.514(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.505(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C11 1.425(5) . ?
C5 C6 1.389(5) . ?
C5 C10 1.410(5) . ?
C6 C7 1.369(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(5) . ?
C9 H9 0.9300 . ?
C10 N1 1.400(5) . ?
C11 C12 1.338(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.444(6) . ?
C12 H12 0.9300 . ?
C13 O2 1.199(5) . ?
C13 O3 1.350(4) . ?
C14 O3 1.422(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O4 1.194(5) . ?
C15 O5 1.338(5) . ?
C15 N1 1.356(5) . ?
C16 C17 1.399(6) . ?
C16 O5 1.439(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 H1N 0.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 O1 113.2(3) . . ?
C4 C1 C5 132.3(4) . . ?
O1 C1 C5 114.5(3) . . ?
O1 C2 C3 106.3(3) . . ?
O1 C2 H2A 110.5 . . ?
C3 C2 H2A 110.5 . . ?
O1 C2 H2B 110.5 . . ?
C3 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C4 C3 C2 102.5(3) . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C1 C4 C11 129.5(3) . . ?
C1 C4 C3 108.7(3) . . ?
C11 C4 C3 121.8(3) . . ?
C6 C5 C10 118.1(4) . . ?
C6 C5 C1 119.5(3) . . ?
C10 C5 C1 122.3(3) . . ?
C7 C6 C5 122.0(4) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 119.4(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 120.3(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 120.4(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 N1 122.0(4) . . ?
C9 C10 C5 119.7(4) . . ?
N1 C10 C5 118.3(3) . . ?
C12 C11 C4 123.9(4) . . ?
C12 C11 H11 118.0 . . ?
C4 C11 H11 118.0 . . ?
C11 C12 C13 124.2(4) . . ?
C11 C12 H12 117.9 . . ?
C13 C12 H12 117.9 . . ?
O2 C13 O3 122.0(4) . . ?
O2 C13 C12 126.7(4) . . ?
O3 C13 C12 111.2(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O5 125.1(4) . . ?
O4 C15 N1 127.3(4) . . ?
O5 C15 N1 107.6(3) . . ?
C17 C16 O5 111.7(4) . . ?
C17 C16 H16A 109.3 . . ?
O5 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
O5 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 N1 C10 129.6(4) . . ?
C15 N1 H1N 114(2) . . ?
C10 N1 H1N 116(2) . . ?
C1 O1 C2 108.1(3) . . ?
C13 O3 C14 116.6(3) . . ?
C15 O5 C16 117.3(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
O1 C2 C3 C4 10.8(4) . . . . ?
O1 C1 C4 C11 -175.4(4) . . . . ?
C5 C1 C4 C11 6.3(7) . . . . ?
O1 C1 C4 C3 2.3(5) . . . . ?
C5 C1 C4 C3 -176.0(4) . . . . ?
C2 C3 C4 C1 -8.2(5) . . . . ?
C2 C3 C4 C11 169.7(4) . . . . ?
C4 C1 C5 C6 40.0(6) . . . . ?
O1 C1 C5 C6 -138.3(4) . . . . ?
C4 C1 C5 C10 -141.6(4) . . . . ?
O1 C1 C5 C10 40.1(5) . . . . ?
C10 C5 C6 C7 0.2(6) . . . . ?
C1 C5 C6 C7 178.6(4) . . . . ?
C5 C6 C7 C8 -1.0(7) . . . . ?
C6 C7 C8 C9 0.3(7) . . . . ?
C7 C8 C9 C10 1.2(7) . . . . ?
C8 C9 C10 N1 178.0(4) . . . . ?
C8 C9 C10 C5 -2.0(6) . . . . ?
C6 C5 C10 C9 1.3(6) . . . . ?
C1 C5 C10 C9 -177.1(4) . . . . ?
C6 C5 C10 N1 -178.7(4) . . . . ?
C1 C5 C10 N1 2.9(6) . . . . ?
C1 C4 C11 C12 -178.3(4) . . . . ?
C3 C4 C11 C12 4.2(6) . . . . ?
C4 C11 C12 C13 -175.3(4) . . . . ?
C11 C12 C13 O2 -7.0(7) . . . . ?
C11 C12 C13 O3 171.9(4) . . . . ?
O4 C15 N1 C10 5.1(8) . . . . ?
O5 C15 N1 C10 -173.7(4) . . . . ?
C9 C10 N1 C15 -13.2(7) . . . . ?
C5 C10 N1 C15 166.9(4) . . . . ?
C4 C1 O1 C2 5.1(4) . . . . ?
C5 C1 O1 C2 -176.3(3) . . . . ?
C3 C2 O1 C1 -10.1(4) . . . . ?
O2 C13 O3 C14 5.7(6) . . . . ?
C12 C13 O3 C14 -173.2(4) . . . . ?
O4 C15 O5 C16 4.8(7) . . . . ?
N1 C15 O5 C16 -176.4(4) . . . . ?
C17 C16 O5 C15 -152.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.84(3) 2.05(3) 2.706(4) 135(3) .

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_az56
_database_code_depnum_ccdc_archive 'CCDC 1405059'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 I N O2'
_chemical_formula_sum            'C17 H14 I N O2'
_chemical_formula_weight         391.19

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   13.7811(12)
_cell_length_b                   13.3475(11)
_cell_length_c                   16.9711(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3121.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9684
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.09

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.055
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33971
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.400
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3837
_reflns_number_gt                2902
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+2.5869P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3837
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8769(2) 0.4678(2) 0.63074(16) 0.0427(6) Uani 1 1 d . . . . .
C2 C 0.9979(3) 0.3503(3) 0.6387(3) 0.0670(10) Uani 1 1 d . . . . .
H2A H 1.0190 0.3004 0.6008 0.080 Uiso 1 1 calc R U . . .
H2B H 1.0156 0.3278 0.6911 0.080 Uiso 1 1 calc R U . . .
C3 C 1.0444(3) 0.4501(3) 0.6212(2) 0.0690(10) Uani 1 1 d . . . . .
H3A H 1.0928 0.4673 0.6605 0.083 Uiso 1 1 calc R U . . .
H3B H 1.0742 0.4507 0.5694 0.083 Uiso 1 1 calc R U . . .
C4 C 0.9588(2) 0.5195(3) 0.62481(19) 0.0523(7) Uani 1 1 d . . . . .
C5 C 0.7738(2) 0.4960(2) 0.63564(15) 0.0397(6) Uani 1 1 d . . . . .
C6 C 0.7460(2) 0.5738(2) 0.68539(19) 0.0532(7) Uani 1 1 d . . . . .
H6 H 0.7931 0.6077 0.7141 0.064 Uiso 1 1 calc R U . . .
C7 C 0.6500(3) 0.6018(3) 0.6931(2) 0.0623(9) Uani 1 1 d . . . . .
H7 H 0.6328 0.6544 0.7262 0.075 Uiso 1 1 calc R U . . .
C8 C 0.5806(3) 0.5515(3) 0.6516(2) 0.0636(9) Uani 1 1 d . . . . .
H8 H 0.5160 0.5703 0.6564 0.076 Uiso 1 1 calc R U . . .
C9 C 0.6051(2) 0.4727(3) 0.6023(2) 0.0571(8) Uani 1 1 d . . . . .
H9 H 0.5569 0.4382 0.5752 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7017(2) 0.4452(2) 0.59342(17) 0.0430(6) Uani 1 1 d . . . . .
C11 C 0.6824(2) 0.3338(2) 0.47730(18) 0.0438(6) Uani 1 1 d . . . . .
C12 C 0.7335(2) 0.2528(2) 0.43282(16) 0.0413(6) Uani 1 1 d . . . . .
C13 C 0.7930(2) 0.1822(2) 0.46785(19) 0.0492(7) Uani 1 1 d . . . . .
H13 H 0.8031 0.1837 0.5220 0.059 Uiso 1 1 calc R U . . .
C14 C 0.8376(3) 0.1092(3) 0.4224(2) 0.0595(8) Uani 1 1 d . . . . .
H14 H 0.8773 0.0616 0.4461 0.071 Uiso 1 1 calc R U . . .
C15 C 0.8229(3) 0.1073(3) 0.3423(2) 0.0643(9) Uani 1 1 d . . . . .
H15 H 0.8536 0.0590 0.3117 0.077 Uiso 1 1 calc R U . . .
C16 C 0.7628(3) 0.1766(3) 0.3072(2) 0.0640(9) Uani 1 1 d . . . . .
H16 H 0.7525 0.1748 0.2531 0.077 Uiso 1 1 calc R U . . .
C17 C 0.7182(2) 0.2484(2) 0.35226(18) 0.0510(7) Uani 1 1 d . . . . .
H17 H 0.6771 0.2946 0.3284 0.061 Uiso 1 1 calc R U . . .
I1 I 0.97492(2) 0.67215(2) 0.61170(2) 0.08618(16) Uani 1 1 d . . . . .
N1 N 0.7296(2) 0.3671(2) 0.54195(16) 0.0487(6) Uani 1 1 d . . . . .
H1N H 0.783(3) 0.344(2) 0.5499(19) 0.044(9) Uiso 1 1 d . . . . .
O1 O 0.89308(16) 0.36520(17) 0.63335(14) 0.0529(5) Uani 1 1 d . . . . .
O2 O 0.60465(18) 0.36720(18) 0.45495(14) 0.0634(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.326(5) . ?
C1 O1 1.388(4) . ?
C1 C5 1.473(4) . ?
C2 O1 1.461(4) . ?
C2 C3 1.508(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.502(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 I1 2.061(3) . ?
C5 C6 1.392(4) . ?
C5 C10 1.400(4) . ?
C6 C7 1.380(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C10 N1 1.414(4) . ?
C11 O2 1.221(4) . ?
C11 N1 1.350(4) . ?
C11 C12 1.495(4) . ?
C12 C13 1.383(4) . ?
C12 C17 1.385(4) . ?
C13 C14 1.386(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N1 H1N 0.81(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 O1 112.3(3) . . ?
C4 C1 C5 133.8(3) . . ?
O1 C1 C5 113.9(3) . . ?
O1 C2 C3 106.8(3) . . ?
O1 C2 H2A 110.4 . . ?
C3 C2 H2A 110.4 . . ?
O1 C2 H2B 110.4 . . ?
C3 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C4 C3 C2 101.7(3) . . ?
C4 C3 H3A 111.4 . . ?
C2 C3 H3A 111.4 . . ?
C4 C3 H3B 111.4 . . ?
C2 C3 H3B 111.4 . . ?
H3A C3 H3B 109.3 . . ?
C1 C4 C3 110.5(3) . . ?
C1 C4 I1 127.9(3) . . ?
C3 C4 I1 121.3(3) . . ?
C6 C5 C10 118.4(3) . . ?
C6 C5 C1 119.4(3) . . ?
C10 C5 C1 122.2(2) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C6 119.3(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 119.8(3) . . ?
C9 C10 N1 121.5(3) . . ?
C5 C10 N1 118.7(3) . . ?
O2 C11 N1 123.7(3) . . ?
O2 C11 C12 121.4(3) . . ?
N1 C11 C12 114.9(3) . . ?
C13 C12 C17 119.1(3) . . ?
C13 C12 C11 123.7(3) . . ?
C17 C12 C11 117.2(3) . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C11 N1 C10 127.9(3) . . ?
C11 N1 H1N 117(2) . . ?
C10 N1 H1N 115(2) . . ?
C1 O1 C2 107.1(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
O1 C2 C3 C4 12.1(4) . . . . ?
O1 C1 C4 C3 1.1(4) . . . . ?
C5 C1 C4 C3 -179.4(3) . . . . ?
O1 C1 C4 I1 175.7(2) . . . . ?
C5 C1 C4 I1 -4.8(5) . . . . ?
C2 C3 C4 C1 -8.4(4) . . . . ?
C2 C3 C4 I1 176.6(3) . . . . ?
C4 C1 C5 C6 -44.6(5) . . . . ?
O1 C1 C5 C6 134.8(3) . . . . ?
C4 C1 C5 C10 137.2(4) . . . . ?
O1 C1 C5 C10 -43.3(4) . . . . ?
C10 C5 C6 C7 -0.6(5) . . . . ?
C1 C5 C6 C7 -178.8(3) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C6 C7 C8 C9 0.3(6) . . . . ?
C7 C8 C9 C10 -1.3(6) . . . . ?
C8 C9 C10 C5 1.4(5) . . . . ?
C8 C9 C10 N1 -178.2(3) . . . . ?
C6 C5 C10 C9 -0.4(4) . . . . ?
C1 C5 C10 C9 177.7(3) . . . . ?
C6 C5 C10 N1 179.1(3) . . . . ?
C1 C5 C10 N1 -2.7(4) . . . . ?
O2 C11 C12 C13 -149.7(3) . . . . ?
N1 C11 C12 C13 31.4(4) . . . . ?
O2 C11 C12 C17 29.1(4) . . . . ?
N1 C11 C12 C17 -149.8(3) . . . . ?
C17 C12 C13 C14 1.0(4) . . . . ?
C11 C12 C13 C14 179.8(3) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
C14 C15 C16 C17 0.6(5) . . . . ?
C15 C16 C17 C12 0.7(5) . . . . ?
C13 C12 C17 C16 -1.5(4) . . . . ?
C11 C12 C17 C16 179.6(3) . . . . ?
O2 C11 N1 C10 -1.8(5) . . . . ?
C12 C11 N1 C10 177.1(3) . . . . ?
C9 C10 N1 C11 25.7(5) . . . . ?
C5 C10 N1 C11 -153.9(3) . . . . ?
C4 C1 O1 C2 7.1(4) . . . . ?
C5 C1 O1 C2 -172.5(3) . . . . ?
C3 C2 O1 C1 -12.2(4) . . . . ?

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
N1 H1N O1 0.81(4) 2.09(3) 2.736(3) 136(3) .

_refine_diff_density_max         1.262
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.078



