# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_cd214501
_database_code_depnum_ccdc_archive 'CCDC 1023013'
_audit_update_record             
;
2014-09-05 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(R)-2-(4-(tert-butyl)phenyl)-2-(iodomethyl)-3,3-dimethyloxirane
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H21 I O'
_chemical_formula_weight         344.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   22.448(6)
_cell_length_b                   6.0248(16)
_cell_length_c                   11.443(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.517(5)
_cell_angle_gamma                90
_cell_volume                     1534.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2374
_cell_measurement_theta_min      4.780
_cell_measurement_theta_max      48.354

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    2.072
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5424
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4703
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.795
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_point_group_measured_fraction_full 0.816
_reflns_number_total             2451
_reflns_number_gt                2322
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.473
_reflns_Friedel_fraction_max     0.578
_reflns_Friedel_fraction_full    0.589

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0427P)²+1.8756P] 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 721 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2451
_refine_ls_number_parameters     159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.72482(2) 0.54089(14) 0.37813(4) 0.0784(2) Uani 1 1 d . . . . .
O1 O 0.6629(2) 0.6847(9) 0.0990(4) 0.0659(12) Uani 1 1 d . . . . .
C1 C 0.6917(3) 0.8466(12) 0.2979(7) 0.0658(18) Uani 1 1 d . . . . .
H1A H 0.6750 0.9373 0.3556 0.079 Uiso 1 1 calc R U . . .
H1B H 0.7246 0.9281 0.2708 0.079 Uiso 1 1 calc R U . . .
C2 C 0.6439(3) 0.8007(11) 0.1950(6) 0.0541(14) Uani 1 1 d . . . . .
C3 C 0.6449(3) 0.9112(14) 0.0785(7) 0.0682(18) Uani 1 1 d . . . . .
C4 C 0.5873(3) 0.9492(17) 0.0001(6) 0.081(2) Uani 1 1 d . . . . .
H4A H 0.5934 0.9261 -0.0805 0.121 Uiso 1 1 calc R U . . .
H4B H 0.5740 1.0986 0.0098 0.121 Uiso 1 1 calc R U . . .
H4C H 0.5574 0.8473 0.0205 0.121 Uiso 1 1 calc R U . . .
C5 C 0.6960(3) 1.070(3) 0.0576(8) 0.090(3) Uani 1 1 d . . . . .
H5A H 0.7318 1.0309 0.1088 0.135 Uiso 1 1 calc R U . . .
H5B H 0.6847 1.2195 0.0738 0.135 Uiso 1 1 calc R U . . .
H5C H 0.7034 1.0591 -0.0230 0.135 Uiso 1 1 calc R U . . .
C6 C 0.5846(2) 0.7311(11) 0.2293(5) 0.0482(12) Uani 1 1 d . . . . .
C7 C 0.5598(2) 0.5280(19) 0.1957(6) 0.0688(17) Uani 1 1 d . . . . .
H7 H 0.5809 0.4305 0.1534 0.083 Uiso 1 1 calc R U . . .
C8 C 0.5036(3) 0.4661(12) 0.2239(7) 0.0697(19) Uani 1 1 d . . . . .
H8 H 0.4876 0.3297 0.1979 0.084 Uiso 1 1 calc R U . . .
C9 C 0.4713(2) 0.6008(10) 0.2890(5) 0.0524(16) Uani 1 1 d . . . . .
C10 C 0.4974(3) 0.8027(12) 0.3256(6) 0.0589(15) Uani 1 1 d . . . . .
H10 H 0.4772 0.8974 0.3711 0.071 Uiso 1 1 calc R U . . .
C11 C 0.5529(3) 0.8666(11) 0.2959(6) 0.0566(15) Uani 1 1 d . . . . .
H11 H 0.5689 1.0033 0.3214 0.068 Uiso 1 1 calc R U . . .
C12 C 0.4099(2) 0.5313(19) 0.3211(5) 0.0598(13) Uani 1 1 d . . . . .
C13 C 0.3745(4) 0.396(2) 0.2209(9) 0.109(4) Uani 1 1 d . . . . .
H13A H 0.3737 0.4751 0.1479 0.164 Uiso 1 1 calc R U . . .
H13B H 0.3341 0.3741 0.2377 0.164 Uiso 1 1 calc R U . . .
H13C H 0.3935 0.2546 0.2147 0.164 Uiso 1 1 calc R U . . .
C14 C 0.4191(4) 0.3832(16) 0.4309(8) 0.080(2) Uani 1 1 d . . . . .
H14A H 0.4457 0.2634 0.4182 0.120 Uiso 1 1 calc R U . . .
H14B H 0.3810 0.3243 0.4457 0.120 Uiso 1 1 calc R U . . .
H14C H 0.4362 0.4693 0.4975 0.120 Uiso 1 1 calc R U . . .
C15 C 0.3722(4) 0.7282(17) 0.3501(11) 0.103(3) Uani 1 1 d . . . . .
H15A H 0.3940 0.8126 0.4128 0.154 Uiso 1 1 calc R U . . .
H15B H 0.3353 0.6759 0.3742 0.154 Uiso 1 1 calc R U . . .
H15C H 0.3635 0.8204 0.2816 0.154 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 C1 2.147(7) . ?
O1 C2 1.414(8) . ?
O1 C3 1.433(10) . ?
C1 C2 1.510(9) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.493(10) . ?
C2 C6 1.497(8) . ?
C3 C4 1.492(10) . ?
C3 C5 1.536(13) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C11 1.378(9) . ?
C6 C7 1.378(12) . ?
C7 C8 1.392(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(9) . ?
C9 C12 1.529(8) . ?
C10 C11 1.386(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C15 1.519(12) . ?
C12 C14 1.533(12) . ?
C12 C13 1.541(12) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 63.2(5) . . ?
C2 C1 I1 110.3(5) . . ?
C2 C1 H1A 109.6 . . ?
I1 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
I1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C3 59.0(5) . . ?
O1 C2 C6 115.7(5) . . ?
C3 C2 C6 118.5(5) . . ?
O1 C2 C1 116.2(5) . . ?
C3 C2 C1 121.5(6) . . ?
C6 C2 C1 114.3(6) . . ?
O1 C3 C4 116.6(7) . . ?
O1 C3 C2 57.8(4) . . ?
C4 C3 C2 119.5(6) . . ?
O1 C3 C5 114.8(7) . . ?
C4 C3 C5 114.6(7) . . ?
C2 C3 C5 121.0(6) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 117.5(5) . . ?
C11 C6 C2 121.4(6) . . ?
C7 C6 C2 121.1(6) . . ?
C6 C7 C8 121.2(7) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 121.8(7) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 116.6(6) . . ?
C8 C9 C12 121.7(6) . . ?
C10 C9 C12 121.7(6) . . ?
C11 C10 C9 121.8(6) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C6 C11 C10 121.1(6) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C15 C12 C9 112.6(8) . . ?
C15 C12 C14 107.1(7) . . ?
C9 C12 C14 109.2(5) . . ?
C15 C12 C13 109.1(8) . . ?
C9 C12 C13 111.1(5) . . ?
C14 C12 C13 107.6(9) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C3 O1 C2 C6 109.2(6) . . . . ?
C3 O1 C2 C1 -112.6(7) . . . . ?
I1 C1 C2 O1 -64.1(7) . . . . ?
I1 C1 C2 C3 -132.3(6) . . . . ?
I1 C1 C2 C6 74.7(6) . . . . ?
C2 O1 C3 C4 -109.6(7) . . . . ?
C2 O1 C3 C5 112.3(7) . . . . ?
C6 C2 C3 O1 -104.5(7) . . . . ?
C1 C2 C3 O1 103.6(7) . . . . ?
O1 C2 C3 C4 104.6(8) . . . . ?
C6 C2 C3 C4 0.1(11) . . . . ?
C1 C2 C3 C4 -151.8(8) . . . . ?
O1 C2 C3 C5 -101.5(9) . . . . ?
C6 C2 C3 C5 154.1(8) . . . . ?
C1 C2 C3 C5 2.1(12) . . . . ?
O1 C2 C6 C11 -161.0(6) . . . . ?
C3 C2 C6 C11 -93.9(8) . . . . ?
C1 C2 C6 C11 60.0(8) . . . . ?
O1 C2 C6 C7 19.3(9) . . . . ?
C3 C2 C6 C7 86.4(9) . . . . ?
C1 C2 C6 C7 -119.8(7) . . . . ?
C11 C6 C7 C8 2.6(11) . . . . ?
C2 C6 C7 C8 -177.7(7) . . . . ?
C6 C7 C8 C9 -1.9(13) . . . . ?
C7 C8 C9 C10 0.0(11) . . . . ?
C7 C8 C9 C12 -179.2(7) . . . . ?
C8 C9 C10 C11 1.2(10) . . . . ?
C12 C9 C10 C11 -179.6(6) . . . . ?
C7 C6 C11 C10 -1.4(10) . . . . ?
C2 C6 C11 C10 178.8(6) . . . . ?
C9 C10 C11 C6 -0.5(10) . . . . ?
C8 C9 C12 C15 -158.0(8) . . . . ?
C10 C9 C12 C15 22.8(9) . . . . ?
C8 C9 C12 C14 83.2(8) . . . . ?
C10 C9 C12 C14 -96.0(9) . . . . ?
C8 C9 C12 C13 -35.4(12) . . . . ?
C10 C9 C12 C13 145.5(9) . . . . ?

_refine_diff_density_max         1.005
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-4



_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_cd214569
_database_code_depnum_ccdc_archive 'CCDC 1028455'
_audit_update_record             
;
2014-10-10 deposited with the CCDC.
2015-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
(S,E)-1-(2,4-dinitrophenyl)-2-(2-(iodomethyl)-2-phenylcyclohexylidene)hydrazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 I N4 O4'
_chemical_formula_weight         494.28

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                   10.310(10)
_cell_length_b                   7.955(8)
_cell_length_c                   11.875(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.15(2)
_cell_angle_gamma                90
_cell_volume                     973.9(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2866
_cell_measurement_theta_min      5.228
_cell_measurement_theta_max      48.648

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    1.678
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5509
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5871
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.715
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_point_group_measured_fraction_full 0.878
_reflns_number_total             3341
_reflns_number_gt                3039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.627
_reflns_Friedel_fraction_max     0.728
_reflns_Friedel_fraction_full    0.739

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0665P)²] 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 1073 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.03(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3341
_refine_ls_number_parameters     257
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.19636(4) 0.43290(9) 0.51402(4) 0.0674(2) Uani 1 1 d . . . . .
N1 N 0.0953(5) 0.9189(11) 0.7268(4) 0.0471(12) Uani 1 1 d . . . . .
N2 N 0.0518(6) 1.0568(8) 0.7863(5) 0.0522(13) Uani 1 1 d D . . . .
N3 N -0.3951(7) 0.9758(11) 1.0450(5) 0.066(2) Uani 1 1 d . . . . .
N4 N -0.0681(6) 1.3460(8) 0.8926(5) 0.0558(14) Uani 1 1 d . . . . .
O1 O -0.4151(11) 0.8355(13) 1.0788(8) 0.120(3) Uani 1 1 d . . . . .
O2 O -0.4593(7) 1.0955(12) 1.0675(5) 0.088(2) Uani 1 1 d . . . . .
O3 O -0.1247(6) 1.4585(8) 0.9423(5) 0.0692(15) Uani 1 1 d . . . . .
O4 O 0.0308(6) 1.3736(7) 0.8385(5) 0.0695(14) Uani 1 1 d . . . . .
C1 C 0.2132(5) 0.9239(12) 0.6913(4) 0.0439(11) Uani 1 1 d . . . . .
C2 C 0.3129(7) 1.0575(10) 0.7185(6) 0.0577(17) Uani 1 1 d . . . . .
H2A H 0.2751 1.1425 0.7670 0.069 Uiso 1 1 calc R U . . .
H2B H 0.3418 1.1116 0.6498 0.069 Uiso 1 1 calc R U . . .
C3 C 0.4266(7) 0.9744(11) 0.7773(7) 0.066(2) Uani 1 1 d . . . . .
H3A H 0.4929 1.0576 0.7932 0.079 Uiso 1 1 calc R U . . .
H3B H 0.3982 0.9268 0.8483 0.079 Uiso 1 1 calc R U . . .
C4 C 0.4824(7) 0.8369(11) 0.7037(7) 0.065(2) Uani 1 1 d . . . . .
H4A H 0.5161 0.8858 0.6349 0.078 Uiso 1 1 calc R U . . .
H4B H 0.5536 0.7824 0.7428 0.078 Uiso 1 1 calc R U . . .
C5 C 0.3797(6) 0.7082(10) 0.6750(6) 0.0547(16) Uani 1 1 d . . . . .
H5A H 0.3538 0.6515 0.7437 0.066 Uiso 1 1 calc R U . . .
H5B H 0.4175 0.6245 0.6256 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2571(6) 0.7809(8) 0.6176(5) 0.0439(13) Uani 1 1 d . . . . .
C7 C 0.1490(6) 0.6497(9) 0.6124(5) 0.0461(13) Uani 1 1 d . . . . .
H7A H 0.0718 0.7017 0.5811 0.055 Uiso 1 1 calc R U . . .
H7B H 0.1287 0.6140 0.6885 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2820(6) 0.8478(9) 0.4999(5) 0.0424(13) Uani 1 1 d . . . . .
C9 C 0.3893(6) 0.8047(10) 0.4352(6) 0.0536(16) Uani 1 1 d . . . . .
H9 H 0.4526 0.7348 0.4658 0.064 Uiso 1 1 calc R U . . .
C10 C 0.4036(7) 0.8632(12) 0.3277(6) 0.063(2) Uani 1 1 d . . . . .
H10 H 0.4760 0.8320 0.2861 0.076 Uiso 1 1 calc R U . . .
C11 C 0.3147(8) 0.9648(13) 0.2817(6) 0.061(2) Uani 1 1 d . . . . .
H11 H 0.3253 1.0030 0.2083 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2078(8) 1.0129(11) 0.3426(6) 0.0627(19) Uani 1 1 d . . . . .
H12 H 0.1461 1.0838 0.3107 0.075 Uiso 1 1 calc R U . . .
C13 C 0.1925(5) 0.9554(11) 0.4517(5) 0.0501(16) Uani 1 1 d . . . . .
H13 H 0.1209 0.9896 0.4933 0.060 Uiso 1 1 calc R U . . .
C14 C -0.0569(6) 1.0411(9) 0.8481(5) 0.0450(14) Uani 1 1 d . . . . .
C15 C -0.1113(7) 0.8827(9) 0.8663(6) 0.0538(17) Uani 1 1 d . . . . .
H15 H -0.0723 0.7886 0.8344 0.065 Uiso 1 1 calc R U . . .
C16 C -0.2209(8) 0.8626(11) 0.9300(6) 0.0575(18) Uani 1 1 d . . . . .
H16 H -0.2556 0.7561 0.9415 0.069 Uiso 1 1 calc R U . . .
C17 C -0.2788(7) 1.0015(10) 0.9767(5) 0.0521(16) Uani 1 1 d . . . . .
C18 C -0.2317(7) 1.1571(10) 0.9628(5) 0.0498(15) Uani 1 1 d . . . . .
H18 H -0.2736 1.2491 0.9944 0.060 Uiso 1 1 calc R U . . .
C19 C -0.1183(6) 1.1787(8) 0.8997(5) 0.0448(13) Uani 1 1 d . . . . .
H2 H 0.079(6) 1.152(5) 0.773(6) 0.048(19) Uiso 1 1 d 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
I1 C7 2.141(7) . ?
N1 C1 1.289(7) . ?
N1 N2 1.380(10) . ?
N2 C14 1.346(9) . ?
N2 H2 0.82(3) . ?
N3 O2 1.190(11) . ?
N3 O1 1.204(13) . ?
N3 C17 1.464(9) . ?
N4 O3 1.221(8) . ?
N4 O4 1.226(8) . ?
N4 C19 1.431(9) . ?
C1 C6 1.506(10) . ?
C1 C2 1.513(11) . ?
C2 C3 1.515(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.515(12) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.511(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.547(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.518(9) . ?
C6 C7 1.529(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.382(9) . ?
C8 C9 1.391(8) . ?
C9 C10 1.368(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.337(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.396(10) . ?
C14 C19 1.407(9) . ?
C15 C16 1.371(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.340(11) . ?
C18 C19 1.401(9) . ?
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
C1 N1 N2 116.8(7) . . ?
C14 N2 N1 118.5(6) . . ?
C14 N2 H2 118(5) . . ?
N1 N2 H2 121(5) . . ?
O2 N3 O1 124.8(8) . . ?
O2 N3 C17 118.0(8) . . ?
O1 N3 C17 117.0(8) . . ?
O3 N4 O4 121.4(7) . . ?
O3 N4 C19 118.7(6) . . ?
O4 N4 C19 119.9(6) . . ?
N1 C1 C6 116.9(7) . . ?
N1 C1 C2 126.4(7) . . ?
C6 C1 C2 116.7(5) . . ?
C1 C2 C3 108.4(7) . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
C3 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
C4 C3 C2 110.1(6) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 110.6(6) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 114.6(6) . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C1 C6 C8 108.8(5) . . ?
C1 C6 C7 108.6(5) . . ?
C8 C6 C7 109.1(5) . . ?
C1 C6 C5 105.8(5) . . ?
C8 C6 C5 113.4(5) . . ?
C7 C6 C5 110.9(6) . . ?
C6 C7 I1 113.9(4) . . ?
C6 C7 H7A 108.8 . . ?
I1 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
I1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C13 C8 C9 117.1(6) . . ?
C13 C8 C6 118.9(5) . . ?
C9 C8 C6 124.0(6) . . ?
C10 C9 C8 121.3(7) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 120.7(7) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.2(7) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.6(7) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 121.0(6) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N2 C14 C15 120.2(6) . . ?
N2 C14 C19 122.8(7) . . ?
C15 C14 C19 117.0(6) . . ?
C16 C15 C14 121.5(6) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 119.3(7) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 122.4(6) . . ?
C18 C17 N3 119.6(7) . . ?
C16 C17 N3 118.0(7) . . ?
C17 C18 C19 118.9(6) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C14 121.0(7) . . ?
C18 C19 N4 116.7(6) . . ?
C14 C19 N4 122.3(6) . . ?

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
C1 N1 N2 C14 -163.7(6) . . . . ?
N2 N1 C1 C6 -174.6(5) . . . . ?
N2 N1 C1 C2 6.7(10) . . . . ?
N1 C1 C2 C3 119.7(8) . . . . ?
C6 C1 C2 C3 -59.0(8) . . . . ?
C1 C2 C3 C4 57.4(8) . . . . ?
C2 C3 C4 C5 -57.7(8) . . . . ?
C3 C4 C5 C6 56.2(8) . . . . ?
N1 C1 C6 C8 112.8(7) . . . . ?
C2 C1 C6 C8 -68.4(7) . . . . ?
N1 C1 C6 C7 -5.8(8) . . . . ?
C2 C1 C6 C7 173.0(6) . . . . ?
N1 C1 C6 C5 -124.9(6) . . . . ?
C2 C1 C6 C5 53.8(8) . . . . ?
C4 C5 C6 C1 -51.5(8) . . . . ?
C4 C5 C6 C8 67.8(8) . . . . ?
C4 C5 C6 C7 -169.0(6) . . . . ?
C1 C6 C7 I1 -178.5(4) . . . . ?
C8 C6 C7 I1 63.0(6) . . . . ?
C5 C6 C7 I1 -62.6(6) . . . . ?
C1 C6 C8 C13 -45.1(8) . . . . ?
C7 C6 C8 C13 73.2(8) . . . . ?
C5 C6 C8 C13 -162.6(7) . . . . ?
C1 C6 C8 C9 136.3(7) . . . . ?
C7 C6 C8 C9 -105.4(7) . . . . ?
C5 C6 C8 C9 18.8(10) . . . . ?
C13 C8 C9 C10 -1.6(11) . . . . ?
C6 C8 C9 C10 177.1(7) . . . . ?
C8 C9 C10 C11 0.4(12) . . . . ?
C9 C10 C11 C12 0.5(13) . . . . ?
C10 C11 C12 C13 -0.2(13) . . . . ?
C9 C8 C13 C12 1.9(12) . . . . ?
C6 C8 C13 C12 -176.8(7) . . . . ?
C11 C12 C13 C8 -1.1(13) . . . . ?
N1 N2 C14 C15 10.5(9) . . . . ?
N1 N2 C14 C19 -171.6(6) . . . . ?
N2 C14 C15 C16 179.1(7) . . . . ?
C19 C14 C15 C16 1.1(10) . . . . ?
C14 C15 C16 C17 0.2(11) . . . . ?
C15 C16 C17 C18 -0.3(11) . . . . ?
C15 C16 C17 N3 -179.5(7) . . . . ?
O2 N3 C17 C18 14.8(11) . . . . ?
O1 N3 C17 C18 -161.7(9) . . . . ?
O2 N3 C17 C16 -165.9(8) . . . . ?
O1 N3 C17 C16 17.5(11) . . . . ?
C16 C17 C18 C19 -1.0(10) . . . . ?
N3 C17 C18 C19 178.2(6) . . . . ?
C17 C18 C19 C14 2.4(9) . . . . ?
C17 C18 C19 N4 -176.6(6) . . . . ?
N2 C14 C19 C18 179.6(6) . . . . ?
C15 C14 C19 C18 -2.4(9) . . . . ?
N2 C14 C19 N4 -1.5(9) . . . . ?
C15 C14 C19 N4 176.5(6) . . . . ?
O3 N4 C19 C18 1.0(9) . . . . ?
O4 N4 C19 C18 -179.8(6) . . . . ?
O3 N4 C19 C14 -178.0(6) . . . . ?
O4 N4 C19 C14 1.2(9) . . . . ?

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
N2 H2 O4 0.82(3) 1.99(6) 2.604(9) 131(6) .
N2 H2 O4 0.82(3) 1.99(6) 2.604(9) 131(6) .
N2 H2 O4 0.82(3) 1.99(6) 2.604(9) 131(6) .

_refine_diff_density_max         0.804
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-4



