# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_jus1710
_database_code_depnum_ccdc_archive 'CCDC 1997197'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;Department of Chemistry, University of Alberta
Canada
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2021-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'ethyl (2,3-diiodo-5-methoxyphenyl)carbamate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 I2 N O3'
_chemical_formula_sum            'C10 H11 I2 N O3'
_chemical_formula_weight         447.00

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   4.7279(3)
_cell_length_b                   14.6599(10)
_cell_length_c                   19.2246(13)
_cell_angle_alpha                102.2361(8)
_cell_angle_beta                 95.5377(8)
_cell_angle_gamma                92.5611(9)
_cell_volume                     1293.21(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8313
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.09

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.296
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.726
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    4.856
_shelx_estimated_absorpt_T_min   0.126
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2738
_exptl_absorpt_correction_T_max  0.9049
_exptl_absorpt_process_details   'SADABS 2016/2 (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11890
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.973
_diffrn_reflns_theta_max         28.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6233
_reflns_number_gt                5308
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'DIRDIF-2008 (Beurskens et al., 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0289P)²+1.1161P] 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_number_reflns         6233
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0665
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
I1A I 0.53912(5) 0.12949(2) 0.57118(2) 0.03236(7) Uani 1 1 d . . . . .
I2A I 0.44327(6) 0.35142(2) 0.69200(2) 0.04231(8) Uani 1 1 d . . . . .
O1A O -0.2919(5) 0.09634(17) 0.36437(13) 0.0323(5) Uani 1 1 d . . . . .
O2A O 0.0619(5) 0.00146(16) 0.33413(12) 0.0280(5) Uani 1 1 d . . . . .
O3A O -0.2792(5) 0.42087(17) 0.48486(13) 0.0347(6) Uani 1 1 d . . . . .
N1A N 0.1614(6) 0.1247(2) 0.42307(15) 0.0276(6) Uani 1 1 d . . . . .
H1NA H 0.330437 0.101959 0.424953 0.033 Uiso 1 1 calc R U . . .
C1A C 0.1228(6) 0.2091(2) 0.47219(17) 0.0245(6) Uani 1 1 d . . . . .
C2A C 0.2758(6) 0.2281(2) 0.54024(17) 0.0245(6) Uani 1 1 d . . . . .
C3A C 0.2363(7) 0.3127(3) 0.58741(18) 0.0302(7) Uani 1 1 d . . . . .
C4A C 0.0500(7) 0.3749(2) 0.56829(18) 0.0313(7) Uani 1 1 d . . . . .
H4A H 0.024492 0.431387 0.601218 0.038 Uiso 1 1 calc R U . . .
C5A C -0.1009(7) 0.3545(2) 0.50035(18) 0.0298(7) Uani 1 1 d . . . . .
C6A C -0.0621(7) 0.2721(2) 0.45164(18) 0.0283(7) Uani 1 1 d . . . . .
H6A H -0.161099 0.259045 0.404849 0.034 Uiso 1 1 calc R U . . .
C7A C -0.0468(6) 0.0767(2) 0.37323(17) 0.0248(6) Uani 1 1 d . . . . .
C8A C -0.1323(7) -0.0504(3) 0.27465(18) 0.0334(8) Uani 1 1 d . . . . .
H8A H -0.196534 -0.008898 0.242665 0.040 Uiso 1 1 calc R U . . .
H8B H -0.301585 -0.076151 0.292416 0.040 Uiso 1 1 calc R U . . .
C9A C 0.0226(10) -0.1279(3) 0.2350(2) 0.0577(13) Uani 1 1 d . . . . .
H9A H -0.104193 -0.164274 0.194286 0.069 Uiso 1 1 calc R U . . .
H9B H 0.189310 -0.101629 0.217515 0.069 Uiso 1 1 calc R U . . .
H9C H 0.084669 -0.168621 0.267072 0.069 Uiso 1 1 calc R U . . .
C10A C -0.4380(8) 0.4027(3) 0.41750(19) 0.0346(8) Uani 1 1 d . . . . .
H10A H -0.554847 0.455358 0.413676 0.041 Uiso 1 1 calc R U . . .
H10B H -0.308535 0.394547 0.380119 0.041 Uiso 1 1 calc R U . . .
H10C H -0.561748 0.345555 0.411556 0.041 Uiso 1 1 calc R U . . .
I1B I 1.10616(5) 0.39252(2) 0.25632(2) 0.03874(7) Uani 1 1 d . . . . .
I2B I 1.35192(5) 0.15891(2) 0.23177(2) 0.03606(7) Uani 1 1 d . . . . .
O1B O 0.3171(6) 0.39057(19) 0.02905(14) 0.0429(6) Uani 1 1 d . . . . .
O2B O 0.3920(6) 0.51727(18) 0.12029(13) 0.0400(6) Uani 1 1 d . . . . .
O3B O 0.7127(6) 0.0844(2) -0.01808(15) 0.0481(7) Uani 1 1 d . . . . .
N1B N 0.6481(6) 0.3967(2) 0.12614(16) 0.0348(7) Uani 1 1 d . . . . .
H1NB H 0.723868 0.436108 0.165334 0.042 Uiso 1 1 calc R U . . .
C1B C 0.7574(7) 0.3090(2) 0.11395(18) 0.0287(7) Uani 1 1 d . . . . .
C2B C 0.9634(7) 0.2888(2) 0.16493(17) 0.0274(7) Uani 1 1 d . . . . .
C3B C 1.0734(7) 0.2001(3) 0.15385(18) 0.0298(7) Uani 1 1 d . . . . .
C4B C 0.9868(7) 0.1334(3) 0.09263(19) 0.0329(7) Uani 1 1 d . . . . .
H4B H 1.063896 0.073778 0.085092 0.039 Uiso 1 1 calc R U . . .
C5B C 0.7835(7) 0.1547(3) 0.04166(19) 0.0331(7) Uani 1 1 d . . . . .
C6B C 0.6687(7) 0.2408(3) 0.05189(18) 0.0319(7) Uani 1 1 d . . . . .
H6B H 0.529541 0.253741 0.016853 0.038 Uiso 1 1 calc R U . . .
C7B C 0.4398(7) 0.4308(3) 0.08610(18) 0.0309(7) Uani 1 1 d . . . . .
C8B C 0.1818(9) 0.5648(3) 0.0829(2) 0.0403(9) Uani 1 1 d . . . . .
H8C H -0.003805 0.527964 0.073510 0.048 Uiso 1 1 calc R U . . .
H8D H 0.244254 0.571566 0.036449 0.048 Uiso 1 1 calc R U . . .
C9B C 0.1530(13) 0.6587(3) 0.1289(3) 0.0745(17) Uani 1 1 d . . . . .
H9D H 0.012327 0.691805 0.104635 0.089 Uiso 1 1 calc R U . . .
H9E H 0.090168 0.651255 0.174603 0.089 Uiso 1 1 calc R U . . .
H9F H 0.337363 0.694705 0.137670 0.089 Uiso 1 1 calc R U . . .
C10B C 0.4825(9) 0.0965(3) -0.0676(2) 0.0469(10) Uani 1 1 d . . . . .
H10D H 0.454851 0.041595 -0.107371 0.056 Uiso 1 1 calc R U . . .
H10E H 0.308633 0.103802 -0.043541 0.056 Uiso 1 1 calc R U . . .
H10F H 0.524755 0.152433 -0.085998 0.056 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
I1A C2A 2.092(3) . ?
I2A C3A 2.100(3) . ?
O1A C7A 1.212(4) . ?
O2A C7A 1.349(4) . ?
O2A C8A 1.448(4) . ?
O3A C5A 1.376(4) . ?
O3A C10A 1.400(4) . ?
N1A C7A 1.361(4) . ?
N1A C1A 1.419(4) . ?
C1A C6A 1.391(4) . ?
C1A C2A 1.399(4) . ?
C2A C3A 1.404(5) . ?
C3A C4A 1.377(5) . ?
C4A C5A 1.393(5) . ?
C5A C6A 1.395(5) . ?
C8A C9A 1.491(5) . ?
I1B C2B 2.098(3) . ?
I2B C3B 2.102(3) . ?
O1B C7B 1.208(4) . ?
O2B C7B 1.339(4) . ?
O2B C8B 1.458(4) . ?
O3B C5B 1.374(4) . ?
O3B C10B 1.418(5) . ?
N1B C7B 1.368(4) . ?
N1B C1B 1.389(4) . ?
C1B C6B 1.400(5) . ?
C1B C2B 1.400(5) . ?
C2B C3B 1.404(5) . ?
C3B C4B 1.376(5) . ?
C4B C5B 1.399(5) . ?
C5B C6B 1.379(5) . ?
C8B C9B 1.489(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
C7A O2A C8A 114.2(2) . . ?
C5A O3A C10A 118.0(3) . . ?
C7A N1A C1A 124.1(3) . . ?
C6A C1A C2A 121.1(3) . . ?
C6A C1A N1A 119.6(3) . . ?
C2A C1A N1A 119.2(3) . . ?
C1A C2A C3A 118.0(3) . . ?
C1A C2A I1A 120.2(2) . . ?
C3A C2A I1A 121.7(2) . . ?
C4A C3A C2A 121.5(3) . . ?
C4A C3A I2A 115.4(2) . . ?
C2A C3A I2A 123.1(2) . . ?
C3A C4A C5A 119.6(3) . . ?
O3A C5A C4A 116.1(3) . . ?
O3A C5A C6A 123.5(3) . . ?
C4A C5A C6A 120.4(3) . . ?
C1A C6A C5A 119.4(3) . . ?
O1A C7A O2A 124.2(3) . . ?
O1A C7A N1A 126.8(3) . . ?
O2A C7A N1A 109.0(3) . . ?
O2A C8A C9A 107.7(3) . . ?
C7B O2B C8B 115.6(3) . . ?
C5B O3B C10B 117.9(3) . . ?
C7B N1B C1B 129.4(3) . . ?
N1B C1B C6B 121.7(3) . . ?
N1B C1B C2B 119.0(3) . . ?
C6B C1B C2B 119.3(3) . . ?
C1B C2B C3B 119.7(3) . . ?
C1B C2B I1B 119.3(2) . . ?
C3B C2B I1B 121.0(2) . . ?
C4B C3B C2B 120.9(3) . . ?
C4B C3B I2B 116.6(3) . . ?
C2B C3B I2B 122.4(2) . . ?
C3B C4B C5B 119.0(3) . . ?
O3B C5B C6B 123.8(3) . . ?
O3B C5B C4B 114.9(3) . . ?
C6B C5B C4B 121.3(3) . . ?
C5B C6B C1B 119.9(3) . . ?
O1B C7B O2B 124.7(3) . . ?
O1B C7B N1B 126.4(3) . . ?
O2B C7B N1B 108.9(3) . . ?
O2B C8B C9B 108.2(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
C7A N1A C1A C6A -33.4(5) . . . . ?
C7A N1A C1A C2A 147.7(3) . . . . ?
C6A C1A C2A C3A 0.2(5) . . . . ?
N1A C1A C2A C3A 179.2(3) . . . . ?
C6A C1A C2A I1A 177.4(2) . . . . ?
N1A C1A C2A I1A -3.7(4) . . . . ?
C1A C2A C3A C4A 1.0(5) . . . . ?
I1A C2A C3A C4A -176.1(3) . . . . ?
C1A C2A C3A I2A 179.0(2) . . . . ?
I1A C2A C3A I2A 1.9(4) . . . . ?
C2A C3A C4A C5A -0.8(5) . . . . ?
I2A C3A C4A C5A -178.9(3) . . . . ?
C10A O3A C5A C4A -179.2(3) . . . . ?
C10A O3A C5A C6A 2.6(5) . . . . ?
C3A C4A C5A O3A -178.9(3) . . . . ?
C3A C4A C5A C6A -0.6(5) . . . . ?
C2A C1A C6A C5A -1.6(5) . . . . ?
N1A C1A C6A C5A 179.5(3) . . . . ?
O3A C5A C6A C1A 180.0(3) . . . . ?
C4A C5A C6A C1A 1.8(5) . . . . ?
C8A O2A C7A O1A 6.0(4) . . . . ?
C8A O2A C7A N1A -174.3(3) . . . . ?
C1A N1A C7A O1A -2.0(5) . . . . ?
C1A N1A C7A O2A 178.3(3) . . . . ?
C7A O2A C8A C9A 177.3(3) . . . . ?
C7B N1B C1B C6B 3.5(6) . . . . ?
C7B N1B C1B C2B -177.0(3) . . . . ?
N1B C1B C2B C3B 179.2(3) . . . . ?
C6B C1B C2B C3B -1.3(5) . . . . ?
N1B C1B C2B I1B -1.5(4) . . . . ?
C6B C1B C2B I1B 178.0(2) . . . . ?
C1B C2B C3B C4B 1.7(5) . . . . ?
I1B C2B C3B C4B -177.6(3) . . . . ?
C1B C2B C3B I2B -173.8(2) . . . . ?
I1B C2B C3B I2B 6.9(4) . . . . ?
C2B C3B C4B C5B -0.9(5) . . . . ?
I2B C3B C4B C5B 174.8(3) . . . . ?
C10B O3B C5B C6B -8.5(6) . . . . ?
C10B O3B C5B C4B 172.1(3) . . . . ?
C3B C4B C5B O3B 179.2(3) . . . . ?
C3B C4B C5B C6B -0.2(5) . . . . ?
O3B C5B C6B C1B -178.8(3) . . . . ?
C4B C5B C6B C1B 0.6(5) . . . . ?
N1B C1B C6B C5B 179.7(3) . . . . ?
C2B C1B C6B C5B 0.2(5) . . . . ?
C8B O2B C7B O1B -2.1(5) . . . . ?
C8B O2B C7B N1B 177.7(3) . . . . ?
C1B N1B C7B O1B -3.6(6) . . . . ?
C1B N1B C7B O2B 176.5(3) . . . . ?
C7B O2B C8B C9B 179.1(4) . . . . ?

_refine_diff_density_max         0.872
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_jus1711
_database_code_depnum_ccdc_archive 'CCDC 1997198'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;Department of Chemistry, University of Alberta
Canada
;
_audit_update_record             
;
2020-04-15 deposited with the CCDC.	2021-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'ethyl (2,3-diiodophenyl)carbamate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H9 I2 N O2'
_chemical_formula_sum            'C9 H9 I2 N O2'
_chemical_formula_weight         416.97

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.230(3)
_cell_length_b                   13.783(4)
_cell_length_c                   7.0214(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.948(3)
_cell_angle_gamma                90
_cell_volume                     1165.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4513
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.22

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.376
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.396
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    5.371
_shelx_estimated_absorpt_T_min   0.225
_shelx_estimated_absorpt_T_max   0.551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2287
_exptl_absorpt_correction_T_max  0.3742
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9415
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.691
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2585
_reflns_number_gt                2403
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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    'DIRDIF-2008 (Beurskens et al., 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+3.7884P] 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_number_reflns         2585
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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 0.33053(4) 0.00919(3) 0.13582(7) 0.03223(14) Uani 1 1 d . . . . .
I2 I 0.06847(4) 0.13694(4) 0.01482(8) 0.03922(16) Uani 1 1 d . . . . .
O1 O 0.6467(5) 0.2903(4) 0.3380(12) 0.0575(19) Uani 1 1 d . . . . .
O2 O 0.6969(4) 0.1331(3) 0.3480(9) 0.0369(12) Uani 1 1 d . . . . .
N N 0.5216(5) 0.1666(4) 0.2407(10) 0.0344(13) Uani 1 1 d . . . . .
H1N H 0.518943 0.103033 0.229669 0.041 Uiso 1 1 calc R U . . .
C1 C 0.4204(5) 0.2164(5) 0.1846(9) 0.0272(13) Uani 1 1 d . . . . .
C2 C 0.3217(5) 0.1617(4) 0.1341(9) 0.0249(11) Uani 1 1 d . . . . .
C3 C 0.2209(5) 0.2097(5) 0.0822(9) 0.0276(13) Uani 1 1 d . . . . .
C4 C 0.2164(6) 0.3110(5) 0.0764(10) 0.0304(13) Uani 1 1 d . . . . .
H4 H 0.147611 0.343564 0.038111 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3135(6) 0.3630(4) 0.1274(10) 0.0302(14) Uani 1 1 d . . . . .
H5 H 0.310489 0.431916 0.126790 0.036 Uiso 1 1 calc R U . . .
C6 C 0.4148(6) 0.3177(4) 0.1792(10) 0.0294(14) Uani 1 1 d . . . . .
H6 H 0.480596 0.355214 0.211150 0.035 Uiso 1 1 calc R U . . .
C7 C 0.6237(6) 0.2059(5) 0.3105(11) 0.0316(15) Uani 1 1 d . . . . .
C8 C 0.8099(6) 0.1622(6) 0.4241(17) 0.050(2) Uani 1 1 d . . . . .
H8A H 0.812049 0.197518 0.547454 0.060 Uiso 1 1 calc R U . . .
H8B H 0.837428 0.206220 0.331462 0.060 Uiso 1 1 calc R U . . .
C9 C 0.8813(6) 0.0755(6) 0.4564(16) 0.048(2) Uani 1 1 d . . . . .
H9A H 0.957723 0.095215 0.507901 0.057 Uiso 1 1 calc R U . . .
H9B H 0.854241 0.032449 0.549213 0.057 Uiso 1 1 calc R U . . .
H9C H 0.879559 0.041130 0.333736 0.057 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 C2 2.105(6) . ?
I2 C3 2.098(7) . ?
O1 C7 1.205(9) . ?
O2 C7 1.340(8) . ?
O2 C8 1.450(9) . ?
N C7 1.371(9) . ?
N C1 1.412(9) . ?
C1 C6 1.398(9) . ?
C1 C2 1.415(9) . ?
C2 C3 1.391(9) . ?
C3 C4 1.398(9) . ?
C4 C5 1.381(10) . ?
C5 C6 1.379(10) . ?
C8 C9 1.475(11) . ?

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
C7 O2 C8 115.3(5) . . ?
C7 N C1 127.5(6) . . ?
C6 C1 N 122.0(6) . . ?
C6 C1 C2 119.4(6) . . ?
N C1 C2 118.6(6) . . ?
C3 C2 C1 119.4(6) . . ?
C3 C2 I1 121.2(5) . . ?
C1 C2 I1 119.4(5) . . ?
C2 C3 C4 120.8(6) . . ?
C2 C3 I2 123.0(5) . . ?
C4 C3 I2 116.2(5) . . ?
C5 C4 C3 118.9(6) . . ?
C6 C5 C4 121.8(6) . . ?
C5 C6 C1 119.8(6) . . ?
O1 C7 O2 124.2(7) . . ?
O1 C7 N 127.7(6) . . ?
O2 C7 N 108.1(5) . . ?
O2 C8 C9 109.5(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
C7 N C1 C6 5.6(12) . . . . ?
C7 N C1 C2 -173.8(7) . . . . ?
C6 C1 C2 C3 -0.7(9) . . . . ?
N C1 C2 C3 178.7(6) . . . . ?
C6 C1 C2 I1 178.6(5) . . . . ?
N C1 C2 I1 -2.0(8) . . . . ?
C1 C2 C3 C4 1.0(10) . . . . ?
I1 C2 C3 C4 -178.2(5) . . . . ?
C1 C2 C3 I2 -177.6(5) . . . . ?
I1 C2 C3 I2 3.2(7) . . . . ?
C2 C3 C4 C5 -1.4(10) . . . . ?
I2 C3 C4 C5 177.3(5) . . . . ?
C3 C4 C5 C6 1.6(11) . . . . ?
C4 C5 C6 C1 -1.3(11) . . . . ?
N C1 C6 C5 -178.6(7) . . . . ?
C2 C1 C6 C5 0.8(10) . . . . ?
C8 O2 C7 O1 -0.8(12) . . . . ?
C8 O2 C7 N -179.8(8) . . . . ?
C1 N C7 O1 0.3(14) . . . . ?
C1 N C7 O2 179.3(7) . . . . ?
C7 O2 C8 C9 -179.4(8) . . . . ?

_refine_diff_density_max         1.058
_refine_diff_density_min         -1.218
_refine_diff_density_rms         0.230

