# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_neal013
_database_code_depnum_ccdc_archive 'CCDC 1438138'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-19 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         ?
_chemical_formula_sum            'C16 H20 I N O5'
_chemical_formula_weight         433.23

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.4983(17)
_cell_length_b                   10.457(3)
_cell_length_c                   27.274(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1853.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1616
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      19.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    1.750
_shelx_estimated_absorpt_T_min   0.671
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5887
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'APEX2 (Bruker, 2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            14104
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.493
_diffrn_reflns_theta_max         27.637
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4306
_reflns_number_gt                2769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 837 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.02(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4306
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
I1 I 0.76825(8) 0.72164(5) 0.04001(2) 0.0588(2) Uani 1 1 d . . . . .
N1 N -0.1490(8) 0.6642(5) 0.2856(2) 0.0293(13) Uani 1 1 d . . . . .
O1 O -0.1332(7) 0.6410(5) 0.36591(17) 0.0393(12) Uani 1 1 d . . . . .
O2 O -0.3665(6) 0.7812(5) 0.33309(17) 0.0370(11) Uani 1 1 d . . . . .
O3 O 0.2428(7) 0.7360(4) 0.30754(16) 0.0405(11) Uani 1 1 d . . . . .
H3 H 0.3675 0.7553 0.3110 0.049 Uiso 1 1 calc R U . . .
O4 O 0.3739(7) 0.5449(5) 0.2883(2) 0.0474(14) Uani 1 1 d . . . . .
O5 O 0.0688(6) 0.7486(4) 0.19643(16) 0.0340(12) Uani 1 1 d . . . . .
C1 C 0.0128(10) 0.5698(6) 0.2800(3) 0.0282(17) Uani 1 1 d . . . . .
H1A H -0.0201 0.4937 0.3008 0.034 Uiso 1 1 calc R U . . .
C2 C -0.0051(11) 0.5323(6) 0.2259(2) 0.0325(17) Uani 1 1 d . . . . .
H2A H 0.1309 0.5092 0.2122 0.039 Uiso 1 1 calc R U . . .
H2B H -0.1005 0.4594 0.2216 0.039 Uiso 1 1 calc R U . . .
C3 C -0.0901(10) 0.6532(6) 0.2015(3) 0.0327(17) Uani 1 1 d . . . . .
H3A H -0.1582 0.6339 0.1695 0.039 Uiso 1 1 calc R U . . .
C4 C -0.2400(10) 0.7043(6) 0.2386(2) 0.0333(15) Uani 1 1 d . . . . .
H4A H -0.2506 0.7985 0.2365 0.040 Uiso 1 1 calc R U . . .
H4B H -0.3783 0.6664 0.2340 0.040 Uiso 1 1 calc R U . . .
C5 C -0.2283(10) 0.7014(6) 0.3288(2) 0.0341(15) Uani 1 1 d . . . . .
C6 C 0.2280(11) 0.6161(6) 0.2922(2) 0.0290(15) Uani 1 1 d . . . . .
C7 C 0.2193(9) 0.7337(6) 0.1611(2) 0.0283(14) Uani 1 1 d . . . . .
C8 C 0.2195(12) 0.6406(6) 0.1254(2) 0.0414(18) Uani 1 1 d . . . . .
H8A H 0.1117 0.5793 0.1242 0.050 Uiso 1 1 calc R U . . .
C9 C 0.3768(11) 0.6366(7) 0.0914(3) 0.044(2) Uani 1 1 d . . . . .
H9A H 0.3781 0.5714 0.0672 0.053 Uiso 1 1 calc R U . . .
C10 C 0.5309(9) 0.7259(7) 0.0924(2) 0.0361(16) Uani 1 1 d . . . . .
C11 C 0.5317(10) 0.8190(7) 0.1281(2) 0.0363(18) Uani 1 1 d . . . . .
H11A H 0.6390 0.8806 0.1292 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3760(10) 0.8222(7) 0.1624(2) 0.0340(17) Uani 1 1 d . . . . .
H12A H 0.3767 0.8862 0.1871 0.041 Uiso 1 1 calc R U . . .
C13 C -0.1761(12) 0.6723(7) 0.4175(3) 0.043(2) Uani 1 1 d . . . . .
C14 C -0.0356(16) 0.5820(9) 0.4443(3) 0.076(3) Uani 1 1 d . . . . .
H14A H -0.0783 0.4937 0.4379 0.115 Uiso 1 1 calc R U . . .
H14B H -0.0429 0.5992 0.4796 0.115 Uiso 1 1 calc R U . . .
H14C H 0.1060 0.5944 0.4329 0.115 Uiso 1 1 calc R U . . .
C15 C -0.1151(16) 0.8111(8) 0.4265(3) 0.081(3) Uani 1 1 d . . . . .
H15A H -0.1984 0.8673 0.4057 0.121 Uiso 1 1 calc R U . . .
H15B H 0.0308 0.8226 0.4187 0.121 Uiso 1 1 calc R U . . .
H15C H -0.1387 0.8327 0.4611 0.121 Uiso 1 1 calc R U . . .
C16 C -0.3992(14) 0.6461(11) 0.4294(3) 0.082(4) Uani 1 1 d . . . . .
H16A H -0.4330 0.5578 0.4205 0.123 Uiso 1 1 calc R U . . .
H16B H -0.4868 0.7050 0.4108 0.123 Uiso 1 1 calc R U . . .
H16C H -0.4224 0.6586 0.4646 0.123 Uiso 1 1 calc R U . . .


_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 C10 2.102(6) . ?
N1 C5 1.345(8) . ?
N1 C1 1.450(8) . ?
N1 C4 1.472(8) . ?
O1 C5 1.343(7) . ?
O1 C13 1.472(8) . ?
O2 C5 1.232(7) . ?
O3 C6 1.326(7) . ?
O3 H3 0.8400 . ?
O4 C6 1.210(7) . ?
O5 C7 1.383(7) . ?
O5 C3 1.442(7) . ?
C1 C6 1.516(9) . ?
C1 C2 1.531(9) . ?
C1 H1A 1.0000 . ?
C2 C3 1.531(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.502(8) . ?
C3 H3A 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C7 C8 1.376(8) . ?
C7 C12 1.377(8) . ?
C8 C9 1.381(9) . ?
C8 H8A 0.9500 . ?
C9 C10 1.370(9) . ?
C9 H9A 0.9500 . ?
C10 C11 1.378(9) . ?
C11 C12 1.377(9) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.503(11) . ?
C13 C16 1.510(11) . ?
C13 C15 1.525(11) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C5 N1 C1 124.5(6) . . ?
C5 N1 C4 121.8(5) . . ?
C1 N1 C4 113.2(5) . . ?
C5 O1 C13 121.9(5) . . ?
C6 O3 H3 109.5 . . ?
C7 O5 C3 119.7(5) . . ?
N1 C1 C6 115.4(5) . . ?
N1 C1 C2 102.7(5) . . ?
C6 C1 C2 111.2(5) . . ?
N1 C1 H1A 109.1 . . ?
C6 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
C3 C2 C1 103.6(5) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
O5 C3 C4 106.4(5) . . ?
O5 C3 C2 110.8(5) . . ?
C4 C3 C2 103.6(5) . . ?
O5 C3 H3A 111.9 . . ?
C4 C3 H3A 111.9 . . ?
C2 C3 H3A 111.9 . . ?
N1 C4 C3 102.9(5) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
O2 C5 O1 125.6(6) . . ?
O2 C5 N1 124.0(6) . . ?
O1 C5 N1 110.4(6) . . ?
O4 C6 O3 123.5(7) . . ?
O4 C6 C1 120.5(5) . . ?
O3 C6 C1 116.0(6) . . ?
C8 C7 C12 119.6(6) . . ?
C8 C7 O5 125.0(6) . . ?
C12 C7 O5 115.4(5) . . ?
C7 C8 C9 119.8(7) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C10 C9 C8 120.5(7) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C9 C10 C11 119.8(6) . . ?
C9 C10 I1 120.6(5) . . ?
C11 C10 I1 119.6(5) . . ?
C12 C11 C10 119.7(7) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 C7 120.6(6) . . ?
C11 C12 H12A 119.7 . . ?
C7 C12 H12A 119.7 . . ?
O1 C13 C14 102.1(6) . . ?
O1 C13 C16 110.3(7) . . ?
C14 C13 C16 111.4(8) . . ?
O1 C13 C15 108.4(6) . . ?
C14 C13 C15 111.2(7) . . ?
C16 C13 C15 112.8(8) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
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 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C6 -76.6(8) . . . . ?
C4 N1 C1 C6 111.2(6) . . . . ?
C5 N1 C1 C2 162.3(5) . . . . ?
C4 N1 C1 C2 -9.9(7) . . . . ?
N1 C1 C2 C3 29.0(6) . . . . ?
C6 C1 C2 C3 -95.0(6) . . . . ?
C7 O5 C3 C4 -173.8(5) . . . . ?
C7 O5 C3 C2 74.2(7) . . . . ?
C1 C2 C3 O5 75.9(6) . . . . ?
C1 C2 C3 C4 -37.9(6) . . . . ?
C5 N1 C4 C3 174.0(5) . . . . ?
C1 N1 C4 C3 -13.5(7) . . . . ?
O5 C3 C4 N1 -85.7(6) . . . . ?
C2 C3 C4 N1 31.2(6) . . . . ?
C13 O1 C5 O2 -4.6(9) . . . . ?
C13 O1 C5 N1 174.3(5) . . . . ?
C1 N1 C5 O2 -179.6(6) . . . . ?
C4 N1 C5 O2 -8.0(9) . . . . ?
C1 N1 C5 O1 1.4(8) . . . . ?
C4 N1 C5 O1 173.0(5) . . . . ?
N1 C1 C6 O4 -179.5(6) . . . . ?
C2 C1 C6 O4 -63.0(8) . . . . ?
N1 C1 C6 O3 1.6(8) . . . . ?
C2 C1 C6 O3 118.0(6) . . . . ?
C3 O5 C7 C8 7.9(9) . . . . ?
C3 O5 C7 C12 -173.4(5) . . . . ?
C12 C7 C8 C9 0.2(10) . . . . ?
O5 C7 C8 C9 178.8(6) . . . . ?
C7 C8 C9 C10 -1.1(11) . . . . ?
C8 C9 C10 C11 1.4(11) . . . . ?
C8 C9 C10 I1 -179.1(5) . . . . ?
C9 C10 C11 C12 -0.7(10) . . . . ?
I1 C10 C11 C12 179.8(5) . . . . ?
C10 C11 C12 C7 -0.2(10) . . . . ?
C8 C7 C12 C11 0.5(9) . . . . ?
O5 C7 C12 C11 -178.3(6) . . . . ?
C5 O1 C13 C14 -179.9(6) . . . . ?
C5 O1 C13 C16 61.6(9) . . . . ?
C5 O1 C13 C15 -62.4(8) . . . . ?

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
O3 H3 O2 0.84 1.85 2.675(6) 166.4 1_655

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_neal012
_database_code_depnum_ccdc_archive 'CCDC 1438139'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-19 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         ?
_chemical_formula_sum            'C27 H26 I N O6'
_chemical_formula_weight         587.39

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   9.8340(9)
_cell_length_b                   8.9990(8)
_cell_length_c                   14.7646(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.4220(14)
_cell_angle_gamma                90
_cell_volume                     1253.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7005
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.47

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.320
_shelx_estimated_absorpt_T_min   0.674
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'APEX2 (Bruker, 2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            19303
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.159
_diffrn_reflns_theta_max         27.780
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5883
_reflns_number_gt                5212
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.999

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+0.3251P] 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_abs_structure_details 
; 
 Flack x determined using 2169 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.023(7)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5883
_refine_ls_number_parameters     323
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_gt          0.0590
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_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
I1 I 1.05011(3) 0.59476(4) 0.16072(2) 0.05246(10) Uani 1 1 d . . . . .
N1 N 0.4139(3) 0.4205(3) 0.4748(2) 0.0226(6) Uani 1 1 d . . . . .
O1 O 0.4131(3) 0.4099(3) 0.62584(18) 0.0253(6) Uani 1 1 d . . . . .
O2 O 0.2182(3) 0.4935(3) 0.51450(18) 0.0323(6) Uani 1 1 d . . . . .
O3 O 0.7959(3) 0.3787(3) 0.5606(2) 0.0416(7) Uani 1 1 d D . . . .
H3 H 0.865(5) 0.430(5) 0.579(3) 0.050 Uiso 1 1 d D U . . .
O4 O 0.6641(2) 0.5827(3) 0.55182(16) 0.0316(5) Uani 1 1 d . . . . .
O5 O 0.5401(3) 0.5457(2) 0.33157(18) 0.0307(6) Uani 1 1 d . . . . .
O6 O 0.0135(3) 0.5578(4) 0.5994(3) 0.0490(9) Uani 1 1 d D . . . .
H6 H 0.078(5) 0.539(5) 0.576(4) 0.059 Uiso 1 1 d D U . . .
C1 C 0.5513(4) 0.3465(4) 0.4952(2) 0.0242(7) Uani 1 1 d . . . . .
H1A H 0.5539 0.2589 0.5373 0.029 Uiso 1 1 calc R U . . .
C2 C 0.5545(4) 0.2946(4) 0.3961(3) 0.0288(8) Uani 1 1 d . . . . .
H2A H 0.6526 0.2944 0.3907 0.035 Uiso 1 1 calc R U . . .
H2B H 0.5143 0.1935 0.3824 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4644(4) 0.4071(4) 0.3300(3) 0.0290(8) Uani 1 1 d . . . . .
H3A H 0.4272 0.3671 0.2644 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3456(4) 0.4406(4) 0.3741(2) 0.0295(8) Uani 1 1 d . . . . .
H4A H 0.3105 0.5436 0.3601 0.035 Uiso 1 1 calc R U . . .
H4B H 0.2655 0.3707 0.3512 0.035 Uiso 1 1 calc R U . . .
C5 C 0.3391(3) 0.4441(4) 0.5367(2) 0.0229(7) Uani 1 1 d . . . . .
C6 C 0.6734(4) 0.4513(4) 0.5389(2) 0.0260(7) Uani 1 1 d . . . . .
C7 C 0.6541(4) 0.5422(4) 0.2940(3) 0.0285(8) Uani 1 1 d . . . . .
C8 C 0.6403(5) 0.4942(5) 0.2028(3) 0.0370(9) Uani 1 1 d . . . . .
H8A H 0.5534 0.4530 0.1658 0.044 Uiso 1 1 calc R U . . .
C9 C 0.7558(5) 0.5071(5) 0.1656(3) 0.0418(10) Uani 1 1 d . . . . .
H9A H 0.7474 0.4753 0.1029 0.050 Uiso 1 1 calc R U . . .
C10 C 0.8819(4) 0.5661(4) 0.2200(3) 0.0334(9) Uani 1 1 d . . . . .
C11 C 0.8963(4) 0.6114(5) 0.3117(2) 0.0336(8) Uani 1 1 d . . . . .
H11A H 0.9834 0.6517 0.3491 0.040 Uiso 1 1 calc R U . . .
C12 C 0.7816(3) 0.5973(6) 0.3486(2) 0.0327(7) Uani 1 1 d . . . . .
H12A H 0.7912 0.6258 0.4121 0.039 Uiso 1 1 calc R U . . .
C13 C 0.3440(4) 0.4551(4) 0.6960(2) 0.0261(7) Uani 1 1 d . . . . .
H13A H 0.2526 0.4022 0.6852 0.031 Uiso 1 1 calc R U . . .
H13B H 0.3245 0.5632 0.6907 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4395(4) 0.4191(4) 0.7940(2) 0.0276(7) Uani 1 1 d . . . . .
H14A H 0.4494 0.3093 0.8041 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5841(4) 0.4946(4) 0.8164(3) 0.0321(8) Uani 1 1 d . . . . .
C16 C 0.6938(4) 0.4699(5) 0.7772(3) 0.0433(10) Uani 1 1 d . . . . .
H16A H 0.6870 0.3952 0.7307 0.052 Uiso 1 1 calc R U . . .
C17 C 0.8148(4) 0.5576(6) 0.8077(3) 0.0532(15) Uani 1 1 d . . . . .
H17A H 0.8918 0.5421 0.7819 0.064 Uiso 1 1 calc R U . . .
C18 C 0.8244(5) 0.6662(6) 0.8746(4) 0.0586(13) Uani 1 1 d . . . . .
H18A H 0.9072 0.7259 0.8932 0.070 Uiso 1 1 calc R U . . .
C19 C 0.7156(5) 0.6902(5) 0.9154(3) 0.0473(11) Uani 1 1 d . . . . .
H19A H 0.7243 0.7640 0.9627 0.057 Uiso 1 1 calc R U . . .
C20 C 0.5941(3) 0.6049(6) 0.8861(2) 0.0338(7) Uani 1 1 d . . . . .
C21 C 0.4647(3) 0.6010(6) 0.9161(2) 0.0316(7) Uani 1 1 d . . . . .
C22 C 0.4236(5) 0.6853(5) 0.9830(3) 0.0445(10) Uani 1 1 d . . . . .
H22A H 0.4852 0.7589 1.0187 0.053 Uiso 1 1 calc R U . . .
C23 C 0.2924(5) 0.6605(5) 0.9968(3) 0.0490(11) Uani 1 1 d . . . . .
H23A H 0.2632 0.7185 1.0418 0.059 Uiso 1 1 calc R U . . .
C24 C 0.2025(5) 0.5516(5) 0.9457(3) 0.0442(11) Uani 1 1 d . . . . .
H24A H 0.1130 0.5353 0.9566 0.053 Uiso 1 1 calc R U . . .
C25 C 0.2420(4) 0.4660(5) 0.8785(3) 0.0375(9) Uani 1 1 d . . . . .
H25A H 0.1802 0.3923 0.8431 0.045 Uiso 1 1 calc R U . . .
C26 C 0.3742(4) 0.4911(4) 0.8647(3) 0.0302(8) Uani 1 1 d . . . . .
C27 C 0.0175(6) 0.7098(6) 0.6215(5) 0.0599(15) Uani 1 1 d . . . . .
H27A H -0.0635 0.7347 0.6450 0.090 Uiso 1 1 calc R U . . .
H27B H 0.0129 0.7683 0.5648 0.090 Uiso 1 1 calc R U . . .
H27C H 0.1058 0.7324 0.6703 0.090 Uiso 1 1 calc R U . . .


_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 C10 2.095(3) . ?
N1 C5 1.341(4) . ?
N1 C1 1.459(5) . ?
N1 C4 1.460(4) . ?
O1 C5 1.347(4) . ?
O1 C13 1.448(4) . ?
O2 C5 1.224(4) . ?
O3 C6 1.328(4) . ?
O3 H3 0.80(4) . ?
O4 C6 1.205(5) . ?
O5 C7 1.384(4) . ?
O5 C3 1.449(4) . ?
O6 C27 1.404(6) . ?
O6 H6 0.82(4) . ?
C1 C6 1.520(5) . ?
C1 C2 1.545(5) . ?
C1 H1A 1.0000 . ?
C2 C3 1.508(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.519(5) . ?
C3 H3A 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C7 C12 1.377(5) . ?
C7 C8 1.385(5) . ?
C8 C9 1.399(6) . ?
C8 H8A 0.9500 . ?
C9 C10 1.379(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.383(5) . ?
C11 C12 1.390(4) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.520(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C26 1.517(5) . ?
C14 C15 1.526(5) . ?
C14 H14A 1.0000 . ?
C15 C16 1.379(6) . ?
C15 C20 1.412(6) . ?
C16 C17 1.393(7) . ?
C16 H16A 0.9500 . ?
C17 C18 1.373(7) . ?
C17 H17A 0.9500 . ?
C18 C19 1.385(7) . ?
C18 H18A 0.9500 . ?
C19 C20 1.382(6) . ?
C19 H19A 0.9500 . ?
C20 C21 1.462(5) . ?
C21 C22 1.392(6) . ?
C21 C26 1.402(6) . ?
C22 C23 1.381(7) . ?
C22 H22A 0.9500 . ?
C23 C24 1.391(6) . ?
C23 H23A 0.9500 . ?
C24 C25 1.395(6) . ?
C24 H24A 0.9500 . ?
C25 C26 1.390(5) . ?
C25 H25A 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C5 N1 C1 125.9(3) . . ?
C5 N1 C4 119.4(3) . . ?
C1 N1 C4 113.5(3) . . ?
C5 O1 C13 113.7(3) . . ?
C6 O3 H3 115(4) . . ?
C7 O5 C3 116.4(3) . . ?
C27 O6 H6 109(3) . . ?
N1 C1 C6 112.3(3) . . ?
N1 C1 C2 102.1(3) . . ?
C6 C1 C2 111.4(3) . . ?
N1 C1 H1A 110.3 . . ?
C6 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
C3 C2 C1 104.1(3) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 109.0 . . ?
O5 C3 C2 111.2(3) . . ?
O5 C3 C4 106.0(3) . . ?
C2 C3 C4 103.8(3) . . ?
O5 C3 H3A 111.8 . . ?
C2 C3 H3A 111.8 . . ?
C4 C3 H3A 111.8 . . ?
N1 C4 C3 102.9(3) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
O2 C5 N1 123.6(3) . . ?
O2 C5 O1 124.0(3) . . ?
N1 C5 O1 112.4(3) . . ?
O4 C6 O3 123.3(3) . . ?
O4 C6 C1 126.1(3) . . ?
O3 C6 C1 110.5(3) . . ?
C12 C7 C8 120.3(3) . . ?
C12 C7 O5 117.6(3) . . ?
C8 C7 O5 122.0(3) . . ?
C7 C8 C9 119.3(4) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
C10 C9 C8 119.9(4) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 I1 119.3(3) . . ?
C11 C10 I1 119.9(3) . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
C7 C12 C11 120.6(3) . . ?
C7 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
O1 C13 C14 109.4(3) . . ?
O1 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O1 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C26 C14 C13 107.2(3) . . ?
C26 C14 C15 102.1(3) . . ?
C13 C14 C15 113.5(3) . . ?
C26 C14 H14A 111.2 . . ?
C13 C14 H14A 111.2 . . ?
C15 C14 H14A 111.2 . . ?
C16 C15 C20 121.2(4) . . ?
C16 C15 C14 128.9(4) . . ?
C20 C15 C14 109.9(3) . . ?
C15 C16 C17 118.1(4) . . ?
C15 C16 H16A 121.0 . . ?
C17 C16 H16A 121.0 . . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 H18A 119.4 . . ?
C19 C18 H18A 119.4 . . ?
C20 C19 C18 118.9(4) . . ?
C20 C19 H19A 120.6 . . ?
C18 C19 H19A 120.6 . . ?
C19 C20 C15 119.6(4) . . ?
C19 C20 C21 131.9(4) . . ?
C15 C20 C21 108.4(4) . . ?
C22 C21 C26 120.1(3) . . ?
C22 C21 C20 130.8(4) . . ?
C26 C21 C20 109.1(3) . . ?
C23 C22 C21 119.2(4) . . ?
C23 C22 H22A 120.4 . . ?
C21 C22 H22A 120.4 . . ?
C22 C23 C24 120.7(4) . . ?
C22 C23 H23A 119.7 . . ?
C24 C23 H23A 119.7 . . ?
C23 C24 C25 120.9(4) . . ?
C23 C24 H24A 119.6 . . ?
C25 C24 H24A 119.6 . . ?
C26 C25 C24 118.3(4) . . ?
C26 C25 H25A 120.8 . . ?
C24 C25 H25A 120.8 . . ?
C25 C26 C21 120.8(3) . . ?
C25 C26 C14 128.8(4) . . ?
C21 C26 C14 110.3(3) . . ?
O6 C27 H27A 109.5 . . ?
O6 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O6 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C6 -83.1(4) . . . . ?
C4 N1 C1 C6 109.7(3) . . . . ?
C5 N1 C1 C2 157.5(3) . . . . ?
C4 N1 C1 C2 -9.7(4) . . . . ?
N1 C1 C2 C3 28.8(3) . . . . ?
C6 C1 C2 C3 -91.2(3) . . . . ?
C7 O5 C3 C2 68.1(4) . . . . ?
C7 O5 C3 C4 -179.7(3) . . . . ?
C1 C2 C3 O5 76.2(3) . . . . ?
C1 C2 C3 C4 -37.4(3) . . . . ?
C5 N1 C4 C3 178.8(3) . . . . ?
C1 N1 C4 C3 -13.0(4) . . . . ?
O5 C3 C4 N1 -86.5(3) . . . . ?
C2 C3 C4 N1 30.8(3) . . . . ?
C1 N1 C5 O2 -172.6(3) . . . . ?
C4 N1 C5 O2 -6.0(5) . . . . ?
C1 N1 C5 O1 8.6(5) . . . . ?
C4 N1 C5 O1 175.2(3) . . . . ?
C13 O1 C5 O2 -7.7(5) . . . . ?
C13 O1 C5 N1 171.1(3) . . . . ?
N1 C1 C6 O4 -4.0(5) . . . . ?
C2 C1 C6 O4 109.8(4) . . . . ?
N1 C1 C6 O3 177.0(3) . . . . ?
C2 C1 C6 O3 -69.3(4) . . . . ?
C3 O5 C7 C12 -128.3(4) . . . . ?
C3 O5 C7 C8 55.7(4) . . . . ?
C12 C7 C8 C9 -2.2(6) . . . . ?
O5 C7 C8 C9 173.7(3) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C8 C9 C10 C11 0.7(6) . . . . ?
C8 C9 C10 I1 -176.8(3) . . . . ?
C9 C10 C11 C12 -0.2(7) . . . . ?
I1 C10 C11 C12 177.3(3) . . . . ?
C8 C7 C12 C11 2.8(7) . . . . ?
O5 C7 C12 C11 -173.3(4) . . . . ?
C10 C11 C12 C7 -1.5(7) . . . . ?
C5 O1 C13 C14 -177.0(3) . . . . ?
O1 C13 C14 C26 170.7(3) . . . . ?
O1 C13 C14 C15 58.7(4) . . . . ?
C26 C14 C15 C16 177.2(4) . . . . ?
C13 C14 C15 C16 -67.7(5) . . . . ?
C26 C14 C15 C20 -4.4(4) . . . . ?
C13 C14 C15 C20 110.7(4) . . . . ?
C20 C15 C16 C17 -0.4(6) . . . . ?
C14 C15 C16 C17 177.8(4) . . . . ?
C15 C16 C17 C18 -0.3(7) . . . . ?
C16 C17 C18 C19 1.4(7) . . . . ?
C17 C18 C19 C20 -1.5(7) . . . . ?
C18 C19 C20 C15 0.7(7) . . . . ?
C18 C19 C20 C21 178.5(5) . . . . ?
C16 C15 C20 C19 0.2(6) . . . . ?
C14 C15 C20 C19 -178.3(4) . . . . ?
C16 C15 C20 C21 -178.0(4) . . . . ?
C14 C15 C20 C21 3.5(4) . . . . ?
C19 C20 C21 C22 1.4(8) . . . . ?
C15 C20 C21 C22 179.3(4) . . . . ?
C19 C20 C21 C26 -178.8(5) . . . . ?
C15 C20 C21 C26 -0.9(5) . . . . ?
C26 C21 C22 C23 -0.9(6) . . . . ?
C20 C21 C22 C23 178.9(4) . . . . ?
C21 C22 C23 C24 0.8(7) . . . . ?
C22 C23 C24 C25 -0.7(7) . . . . ?
C23 C24 C25 C26 0.7(6) . . . . ?
C24 C25 C26 C21 -0.8(6) . . . . ?
C24 C25 C26 C14 -177.1(4) . . . . ?
C22 C21 C26 C25 0.9(6) . . . . ?
C20 C21 C26 C25 -178.9(4) . . . . ?
C22 C21 C26 C14 177.8(4) . . . . ?
C20 C21 C26 C14 -2.0(4) . . . . ?
C13 C14 C26 C25 60.9(5) . . . . ?
C15 C14 C26 C25 -179.6(4) . . . . ?
C13 C14 C26 C21 -115.8(3) . . . . ?
C15 C14 C26 C21 3.8(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
O3 H3 O6 0.80(4) 1.81(4) 2.610(4) 170(5) 1_655
O6 H6 O2 0.82(4) 1.90(4) 2.718(4) 176(5) .

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.394
_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_neal030
_database_code_depnum_ccdc_archive 'CCDC 1438140'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-01-19 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         ?
_chemical_formula_sum            'C17 H22 I N O5'
_chemical_formula_weight         447.25

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   6.5131(13)
_cell_length_b                   16.581(3)
_cell_length_c                   8.9446(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.961(3)
_cell_angle_gamma                90
_cell_volume                     960.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3392
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      21.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.114
_exptl_absorpt_coefficient_mu    1.691
_shelx_estimated_absorpt_T_min   0.662
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'APEX3 (Bruker, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            15874
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.289
_diffrn_reflns_theta_max         28.677
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4955
_reflns_number_gt                4168
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1630 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.031(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4955
_refine_ls_number_parameters     221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0725
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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 1.1765(7) 0.6926(4) 0.3126(5) 0.0364(13) Uani 1 1 d . . . . .
C2 C 1.0454(7) 0.6172(3) 0.2903(6) 0.0327(11) Uani 1 1 d . . . . .
H2 H 1.1164 0.5772 0.2296 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8280(8) 0.6352(3) 0.2110(6) 0.0381(12) Uani 1 1 d . . . . .
H3A H 0.7804 0.6895 0.2380 0.046 Uiso 1 1 calc R U . . .
H3B H 0.8269 0.6318 0.1004 0.046 Uiso 1 1 calc R U . . .
C4 C 0.6938(8) 0.5697(3) 0.2698(6) 0.0359(11) Uani 1 1 d . . . . .
H4 H 0.5449 0.5856 0.2593 0.043 Uiso 1 1 calc R U . . .
C5 C 0.7788(7) 0.5612(3) 0.4345(5) 0.0341(11) Uani 1 1 d . . . . .
H5A H 0.7129 0.6001 0.4986 0.041 Uiso 1 1 calc R U . . .
H5B H 0.7584 0.5058 0.4718 0.041 Uiso 1 1 calc R U . . .
C6 C 1.1507(7) 0.5619(3) 0.5390(5) 0.0300(10) Uani 1 1 d . . . . .
C7 C 1.2175(8) 0.4929(4) 0.7814(6) 0.0408(13) Uani 1 1 d . . . . .
C8 C 1.0670(10) 0.4578(5) 0.8849(7) 0.0596(18) Uani 1 1 d . . . . .
H8A H 0.9780 0.5009 0.9166 0.089 Uiso 1 1 calc R U . . .
H8B H 1.1448 0.4338 0.9736 0.089 Uiso 1 1 calc R U . . .
H8C H 0.9818 0.4163 0.8308 0.089 Uiso 1 1 calc R U . . .
C9 C 1.3492(12) 0.5579(5) 0.8615(8) 0.055(2) Uani 1 1 d . . . . .
H9A H 1.4376 0.5823 0.7916 0.083 Uiso 1 1 calc R U . . .
H9B H 1.4355 0.5342 0.9466 0.083 Uiso 1 1 calc R U . . .
H9C H 1.2599 0.5995 0.8984 0.083 Uiso 1 1 calc R U . . .
C10 C 1.3440(12) 0.4261(5) 0.7201(8) 0.066(2) Uani 1 1 d . . . . .
H10A H 1.2517 0.3880 0.6627 0.098 Uiso 1 1 calc R U . . .
H10B H 1.4224 0.3978 0.8037 0.098 Uiso 1 1 calc R U . . .
H10C H 1.4398 0.4493 0.6543 0.098 Uiso 1 1 calc R U . . .
C11 C 1.2525(11) 0.8074(4) 0.4641(9) 0.067(2) Uani 1 1 d . . . . .
H11A H 1.3963 0.7901 0.4863 0.100 Uiso 1 1 calc R U . . .
H11B H 1.2064 0.8338 0.5528 0.100 Uiso 1 1 calc R U . . .
H11C H 1.2419 0.8454 0.3798 0.100 Uiso 1 1 calc R U . . .
C12 C 0.4279(8) 0.4371(3) 0.2833(6) 0.0356(11) Uani 1 1 d . . . . .
H12 H 0.4044 0.4835 0.3415 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2960(8) 0.3714(3) 0.2840(6) 0.0369(12) Uani 1 1 d . . . . .
H13 H 0.1809 0.3734 0.3410 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3310(8) 0.3034(3) 0.2025(6) 0.0369(12) Uani 1 1 d . . . . .
C15 C 0.4964(8) 0.3005(3) 0.1161(6) 0.0412(12) Uani 1 1 d . . . . .
H15 H 0.5198 0.2535 0.0593 0.049 Uiso 1 1 calc R U . . .
C16 C 0.6271(10) 0.3664(4) 0.1132(7) 0.0381(15) Uani 1 1 d . . . . .
H16 H 0.7393 0.3648 0.0534 0.046 Uiso 1 1 calc R U . . .
C17 C 0.5941(7) 0.4352(3) 0.1980(5) 0.0324(11) Uani 1 1 d . . . . .
I1 I 0.13246(5) 0.20461(3) 0.21343(4) 0.05095(13) Uani 1 1 d . . . . .
N1 N 0.9979(6) 0.5792(3) 0.4308(4) 0.0307(9) Uani 1 1 d . . . . .
O1 O 1.3068(5) 0.7091(4) 0.2317(4) 0.0561(10) Uani 1 1 d . . . . .
O2 O 1.1230(6) 0.7374(2) 0.4248(4) 0.0460(9) Uani 1 1 d . . . . .
O3 O 1.3318(5) 0.5758(2) 0.5268(4) 0.0395(9) Uani 1 1 d . . . . .
O4 O 1.0757(5) 0.5275(2) 0.6582(4) 0.0358(8) Uani 1 1 d . . . . .
O5 O 0.7265(6) 0.4977(2) 0.1864(4) 0.0378(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.202(6) . ?
C1 O2 1.325(6) . ?
C1 C2 1.516(8) . ?
C2 N1 1.468(6) . ?
C2 C3 1.546(7) . ?
C2 H2 1.0000 . ?
C3 C4 1.522(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O5 1.435(7) . ?
C4 C5 1.526(7) . ?
C4 H4 1.0000 . ?
C5 N1 1.461(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O3 1.218(6) . ?
C6 O4 1.345(6) . ?
C6 N1 1.345(6) . ?
C7 O4 1.478(6) . ?
C7 C9 1.512(10) . ?
C7 C10 1.517(9) . ?
C7 C8 1.532(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.456(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.388(7) . ?
C12 C13 1.388(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(7) . ?
C14 I1 2.096(5) . ?
C15 C16 1.387(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.399(9) . ?
C16 H16 0.9500 . ?
C17 O5 1.359(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 125.9(6) . . ?
O1 C1 C2 122.2(6) . . ?
O2 C1 C2 111.9(4) . . ?
N1 C2 C1 114.1(4) . . ?
N1 C2 C3 102.2(4) . . ?
C1 C2 C3 112.2(4) . . ?
N1 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C4 C3 C2 103.6(4) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
O5 C4 C3 107.0(4) . . ?
O5 C4 C5 111.5(4) . . ?
C3 C4 C5 103.6(4) . . ?
O5 C4 H4 111.4 . . ?
C3 C4 H4 111.4 . . ?
C5 C4 H4 111.4 . . ?
N1 C5 C4 102.5(4) . . ?
N1 C5 H5A 111.3 . . ?
C4 C5 H5A 111.3 . . ?
N1 C5 H5B 111.3 . . ?
C4 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
O3 C6 O4 125.9(4) . . ?
O3 C6 N1 123.1(5) . . ?
O4 C6 N1 111.0(4) . . ?
O4 C7 C9 110.9(5) . . ?
O4 C7 C10 109.6(5) . . ?
C9 C7 C10 112.9(6) . . ?
O4 C7 C8 102.0(4) . . ?
C9 C7 C8 110.6(5) . . ?
C10 C7 C8 110.3(6) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 120.2(5) . . ?
C17 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 120.3(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 I1 118.6(4) . . ?
C15 C14 I1 121.1(4) . . ?
C16 C15 C14 119.7(5) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.2(6) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
O5 C17 C12 124.1(5) . . ?
O5 C17 C16 116.5(5) . . ?
C12 C17 C16 119.3(5) . . ?
C6 N1 C5 126.3(4) . . ?
C6 N1 C2 120.1(4) . . ?
C5 N1 C2 113.6(4) . . ?
C1 O2 C11 116.0(5) . . ?
C6 O4 C7 120.4(4) . . ?
C17 O5 C4 117.8(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
O1 C1 C2 N1 143.4(5) . . . . ?
O2 C1 C2 N1 -39.2(6) . . . . ?
O1 C1 C2 C3 -100.9(6) . . . . ?
O2 C1 C2 C3 76.4(5) . . . . ?
N1 C2 C3 C4 -28.9(5) . . . . ?
C1 C2 C3 C4 -151.5(4) . . . . ?
C2 C3 C4 O5 -79.5(5) . . . . ?
C2 C3 C4 C5 38.5(5) . . . . ?
O5 C4 C5 N1 82.5(5) . . . . ?
C3 C4 C5 N1 -32.3(5) . . . . ?
C17 C12 C13 C14 1.2(8) . . . . ?
C12 C13 C14 C15 -1.4(8) . . . . ?
C12 C13 C14 I1 178.0(4) . . . . ?
C13 C14 C15 C16 0.4(8) . . . . ?
I1 C14 C15 C16 -178.9(4) . . . . ?
C14 C15 C16 C17 0.7(9) . . . . ?
C13 C12 C17 O5 177.5(5) . . . . ?
C13 C12 C17 C16 -0.2(8) . . . . ?
C15 C16 C17 O5 -178.6(5) . . . . ?
C15 C16 C17 C12 -0.8(9) . . . . ?
O3 C6 N1 C5 177.2(5) . . . . ?
O4 C6 N1 C5 -2.4(7) . . . . ?
O3 C6 N1 C2 -0.4(8) . . . . ?
O4 C6 N1 C2 180.0(4) . . . . ?
C4 C5 N1 C6 -163.2(5) . . . . ?
C4 C5 N1 C2 14.5(6) . . . . ?
C1 C2 N1 C6 -51.9(6) . . . . ?
C3 C2 N1 C6 -173.2(5) . . . . ?
C1 C2 N1 C5 130.3(5) . . . . ?
C3 C2 N1 C5 9.0(6) . . . . ?
O1 C1 O2 C11 -8.3(8) . . . . ?
C2 C1 O2 C11 174.5(5) . . . . ?
O3 C6 O4 C7 -8.3(8) . . . . ?
N1 C6 O4 C7 171.3(4) . . . . ?
C9 C7 O4 C6 65.0(7) . . . . ?
C10 C7 O4 C6 -60.4(7) . . . . ?
C8 C7 O4 C6 -177.3(5) . . . . ?
C12 C17 O5 C4 1.1(7) . . . . ?
C16 C17 O5 C4 178.8(5) . . . . ?
C3 C4 O5 C17 -167.5(4) . . . . ?
C5 C4 O5 C17 79.8(5) . . . . ?

_refine_diff_density_max         0.856
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.064

