# 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 2018

####################################################################### 
# 
# 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_D1
_database_code_depnum_ccdc_archive 'CCDC 1820020'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 I2 O2, H2 O '
_chemical_formula_sum            'C10 H12 I2 O3'
_chemical_formula_weight         434.00

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           84
_space_group_name_H-M_alt        'P 42/m'
_space_group_name_Hall           '-P 4c'


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

_cell_length_a                   8.5167(5)
_cell_length_b                   8.5167(5)
_cell_length_c                   8.8404(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     641.23(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1458
_cell_measurement_theta_min      5.1350
_cell_measurement_theta_max      30.4360

_exptl_crystal_description       prizm
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.248
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    4.891
_exptl_crystal_density_meas_temp ?

# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.27380
_exptl_absorpt_correction_T_max  1.00000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurment_method        '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5273
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.611
_diffrn_reflns_theta_max         32.652
_reflns_number_total             1239
_reflns_number_gt                891
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_structure_solution    
;
SHELXS-2014/7 (Sheldrick, 2014)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
;
_computing_molecular_graphics    
;
Mercury (Bruno et al., 2002)
;
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2013) and PLATON (Spek, 2003)
;

_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)+(0.0300P)²+0.4460P] 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     SHELXL
_refine_ls_extinction_coef       0.0162(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         1152
_refine_ls_number_parameters     49
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.078
_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
I1 I 0.54515(3) 0.25103(4) 0.5000 0.03787(15) Uani 1 2 d S T P . .
O1 O -0.0913(4) 0.1851(4) 0.5000 0.0342(7) Uani 1 2 d DS T P . .
C1 C 0.3106(5) 0.2714(5) 0.5000 0.0373(10) Uani 1 2 d S T P . .
C2 C 0.1724(5) 0.2874(5) 0.5000 0.0334(9) Uani 1 2 d S T P . .
C3 C 0.0047(5) 0.3267(5) 0.5000 0.0263(8) Uani 1 2 d S T P . .
C4 C -0.0392(3) 0.4197(3) 0.3584(3) 0.0306(6) Uani 1 1 d . . . . .
H4A H -0.0069 0.3618 0.2692 0.037 Uiso 1 1 calc R U . . .
H4B H -0.1523 0.4327 0.3543 0.037 Uiso 1 1 calc R U . . .
O2 O 0.0000 0.0000 0.2500 0.0417(11) Uani 1 4 d DS T P . .
H2O H 0.071(7) 0.036(10) 0.201(8) 0.050 Uiso 0.5 1 d D U P . .
H1O H -0.077(9) 0.142(9) 0.582(5) 0.050 Uiso 0.5 1 d D U P . .


_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 2.005(5) . ?
I1 O1 3.146(3) 1_655 ?
O1 C3 1.457(5) . ?
O1 H1O 0.83(2) . ?
C1 C2 1.184(6) . ?
C2 C3 1.467(6) . ?
C3 C4 1.528(4) . ?
C3 C4 1.528(4) 7_556 ?
C4 C4 1.522(6) 3_565 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O2 H2O 0.802(19) . ?

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 I1 O1 174.68(15) . 1_655 ?
C3 O1 H1O 107(6) . . ?
C2 C1 I1 178.4(4) . . ?
C1 C2 C3 173.4(5) . . ?
O1 C3 C2 111.0(3) . . ?
O1 C3 C4 107.0(2) . . ?
C2 C3 C4 110.9(2) . . ?
O1 C3 C4 107.0(2) . 7_556 ?
C2 C3 C4 110.9(2) . 7_556 ?
C4 C3 C4 110.0(3) . 7_556 ?
C4 C4 C3 111.0(2) 3_565 . ?
C4 C4 H4A 109.4 3_565 . ?
C3 C4 H4A 109.4 . . ?
C4 C4 H4B 109.4 3_565 . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?

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 C3 C4 C4 172.5(3) . . . 3_565 ?
C2 C3 C4 C4 -66.3(4) . . . 3_565 ?
C4 C3 C4 C4 56.7(4) 7_556 . . 3_565 ?

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
C4 H4B I1 0.97 3.27 4.020(3) 135.5 1_455
O2 H2O O1 0.802(19) 2.08(4) 2.8239(19) 154(8) 6_556
O1 H1O O2 0.83(2) 2.02(3) 2.8239(19) 164(8) 5_556

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.947
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.129

####################################################################### 
# 
# 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_D3A5
_database_code_depnum_ccdc_archive 'CCDC 1820028'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H12 N2, C10 H12 O2'
_chemical_formula_sum            'C22 H24 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         348.43

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5202(15)
_cell_length_b                   7.7849(10)
_cell_length_c                   11.8577(16)
_cell_angle_alpha                90
_cell_angle_beta                 114.559(2)
_cell_angle_gamma                90
_cell_volume                     967.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3358
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      28.07
_cell_measurement_temperature    228.(2)

_exptl_crystal_description       Irregular
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.160
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372

_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      228.(2)

_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  Graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            9913
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             2395
_reflns_number_gt                1878
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1210
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_number_reflns         2395
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.2847P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker SMART'
_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'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.43914(12) 0.77159(16) 0.50891(12) 0.0337(3) Uani d . . . 1 . .
C C2 0.38734(13) 0.71513(17) 0.58890(13) 0.0372(3) Uani d . . . 1 . .
H H2 0.4081 0.7707 0.6652 0.045 Uiso calc U . R 1 . .
C C3 0.30485(13) 0.57643(18) 0.55573(14) 0.0396(3) Uani d . . . 1 . .
H H3 0.2714 0.5394 0.6116 0.048 Uiso calc U . R 1 . .
N N4 0.27034(11) 0.49259(15) 0.44883(11) 0.0405(3) Uani d . . . 1 . .
C C5 0.32048(14) 0.54729(18) 0.37218(13) 0.0419(3) Uani d . . . 1 . .
H H5 0.2975 0.4897 0.2963 0.05 Uiso calc U . R 1 . .
C C6 0.40433(13) 0.68382(18) 0.39785(13) 0.0396(3) Uani d . . . 1 . .
H H6 0.4374 0.7168 0.3407 0.048 Uiso calc U . R 1 . .
C C7 0.52951(13) 0.92226(18) 0.54145(14) 0.0412(3) Uani d . . . 1 . .
H H7A 0.6074 0.8884 0.533 0.049 Uiso calc U . R 1 . .
H H7B 0.5533 0.9543 0.6282 0.049 Uiso calc U . R 1 . .
C C8 0.07678(12) 0.13624(18) 0.47256(11) 0.0354(3) Uani d . . . 1 . .
C C9 0.05512(13) -0.0415(2) 0.41255(12) 0.0394(3) Uani d . . . 1 . .
H H9A -0.0191 -0.0371 0.3324 0.047 Uiso calc U . R 1 . .
H H9B 0.1296 -0.073 0.3971 0.047 Uiso calc U . R 1 . .
C C10 0.03325(12) -0.17855(18) 0.49249(13) 0.0393(3) Uani d . . . 1 . .
H H10A 0.1115 -0.1927 0.5684 0.047 Uiso calc U . R 1 . .
H H10B 0.0155 -0.2881 0.4478 0.047 Uiso calc U . R 1 . .
C C11 0.20012(12) 0.14111(18) 0.58426(12) 0.0355(3) Uani d . . . 1 . .
C C12 0.29834(13) 0.14640(19) 0.67239(13) 0.0410(3) Uani d . . . 1 . .
H H12 0.3766 0.1506 0.7426 0.049 Uiso calc U . R 1 . .
H H13 0.146(2) 0.330(3) 0.412(2) 0.081(6) Uiso d . . . 1 . .
O O13 0.07775(11) 0.25676(17) 0.38224(10) 0.0639(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.3854(19) ?
C1 C6 . 1.387(2) ?
C1 C7 . 1.5082(18) ?
C2 C3 . 1.3831(19) ?
C2 H2 . 0.94 ?
C3 N4 . 1.3310(19) ?
C3 H3 . 0.94 ?
N4 C5 . 1.3333(18) ?
C5 C6 . 1.382(2) ?
C5 H5 . 0.94 ?
C6 H6 . 0.94 ?
C7 C7 3_676 1.529(3) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C8 O13 . 1.4274(15) ?
C8 C11 . 1.4867(17) ?
C8 C10 3_556 1.524(2) ?
C8 C9 . 1.529(2) ?
C9 C10 . 1.516(2) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C10 C8 3_556 1.524(2) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C11 C12 . 1.1795(18) ?
C12 H12 . 0.94 ?
O13 H13 . 0.92(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 117.19(12) ?
C2 C1 C7 . . 121.30(13) ?
C6 C1 C7 . . 121.50(12) ?
C3 C2 C1 . . 119.57(13) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
N4 C3 C2 . . 123.48(13) ?
N4 C3 H3 . . 118.3 ?
C2 C3 H3 . . 118.3 ?
C3 N4 C5 . . 116.74(12) ?
N4 C5 C6 . . 123.82(13) ?
N4 C5 H5 . . 118.1 ?
C6 C5 H5 . . 118.1 ?
C5 C6 C1 . . 119.19(13) ?
C5 C6 H6 . . 120.4 ?
C1 C6 H6 . . 120.4 ?
C1 C7 C7 . 3_676 112.08(14) ?
C1 C7 H7A . . 109.2 ?
C7 C7 H7A 3_676 . 109.2 ?
C1 C7 H7B . . 109.2 ?
C7 C7 H7B 3_676 . 109.2 ?
H7A C7 H7B . . 107.9 ?
O13 C8 C11 . . 110.43(10) ?
O13 C8 C10 . 3_556 109.19(12) ?
C11 C8 C10 . 3_556 110.31(11) ?
O13 C8 C9 . . 107.25(11) ?
C11 C8 C9 . . 110.39(12) ?
C10 C8 C9 3_556 . 109.21(10) ?
C10 C9 C8 . . 112.53(11) ?
C10 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
C10 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
C9 C10 C8 . 3_556 113.02(11) ?
C9 C10 H10A . . 109.0 ?
C8 C10 H10A 3_556 . 109.0 ?
C9 C10 H10B . . 109.0 ?
C8 C10 H10B 3_556 . 109.0 ?
H10A C10 H10B . . 107.8 ?
C12 C11 C8 . . 179.32(15) ?
C11 C12 H12 . . 180.0 ?
C8 O13 H13 . . 113.0(13) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.06(19) ?
C7 C1 C2 C3 . . . . -179.98(12) ?
C1 C2 C3 N4 . . . . -0.6(2) ?
C2 C3 N4 C5 . . . . 0.6(2) ?
C3 N4 C5 C6 . . . . -0.1(2) ?
N4 C5 C6 C1 . . . . -0.4(2) ?
C2 C1 C6 C5 . . . . 0.4(2) ?
C7 C1 C6 C5 . . . . -179.56(13) ?
C2 C1 C7 C7 . . . 3_676 -111.72(18) ?
C6 C1 C7 C7 . . . 3_676 68.2(2) ?
O13 C8 C9 C10 . . . . -171.84(11) ?
C11 C8 C9 C10 . . . . 67.81(14) ?
C10 C8 C9 C10 3_556 . . . -53.64(15) ?
C8 C9 C10 C8 . . . 3_556 55.71(15) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O13 H13 N4 . 0.92(2) 1.82(2) 2.7314(16) 171.(2) ?

####################################################################### 
# 
# 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_D2
_database_code_depnum_ccdc_archive 'CCDC 1820021'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H10 I2 O2'
_chemical_formula_sum            'C10 H10 I2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         415.98

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.1961(17)
_cell_length_b                   11.5073(18)
_cell_length_c                   9.2386(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.613(4)
_cell_angle_gamma                90
_cell_volume                     1169.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      29.50
_cell_measurement_temperature    130.(2)

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    2.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

_exptl_absorpt_coefficient_mu    5.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_T_max  0.59

_exptl_special_details           
;
;

_diffrn_ambient_temperature      130.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            22544
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         29.58
_diffrn_reflns_theta_full        29.58
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             3266
_reflns_number_gt                3030
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0227
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_gt          0.0436
_refine_ls_wR_factor_ref         0.0443
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_number_reflns         3266
_refine_ls_number_parameters     135
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0129P)²+1.9323P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.085
_refine_diff_density_min         -1.799
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker SMART'
_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'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.83686(18) 0.34855(19) 0.7869(2) 0.0116(4) Uani d . . . 1 . .
C C2 0.76340(19) 0.4269(2) 0.8720(2) 0.0128(4) Uani d . . . 1 . .
H H2A 0.6811 0.4388 0.8129 0.015 Uiso calc U . R 1 . .
H H2B 0.7544 0.3882 0.9651 0.015 Uiso calc U . R 1 . .
C C3 0.8246(2) 0.54458(19) 0.9067(2) 0.0127(4) Uani d . . . 1 . .
H H3A 0.9014 0.5332 0.9779 0.015 Uiso calc U . R 1 . .
H H3B 0.7711 0.5946 0.9542 0.015 Uiso calc U . R 1 . .
C C4 0.85268(19) 0.60704(19) 0.7703(2) 0.0124(4) Uani d . . . 1 . .
C C5 0.9201(2) 0.5262(2) 0.6802(2) 0.0139(4) Uani d . . . 1 . .
H H5A 0.9282 0.5654 0.5871 0.017 Uiso calc U . R 1 . .
H H5B 1.0029 0.5113 0.7363 0.017 Uiso calc U . R 1 . .
C C6 0.85449(19) 0.41034(19) 0.6446(2) 0.0124(4) Uani d . . . 1 . .
H H6A 0.9026 0.3601 0.5898 0.015 Uiso calc U . R 1 . .
H H6B 0.7743 0.4242 0.5813 0.015 Uiso calc U . R 1 . .
C C7 0.7751(2) 0.2348(2) 0.7578(2) 0.0139(4) Uani d . . . 1 . .
C C8 0.7325(2) 0.1400(2) 0.7499(2) 0.0166(4) Uani d . . . 1 . .
I I9 0.66838(2) -0.02182(2) 0.74656(2) 0.03337(6) Uani d . . . 1 . .
H H10 0.992(3) 0.293(3) 0.831(3) 0.023(8) Uiso d . . D 1 . .
O O10 0.95268(14) 0.32742(15) 0.88031(17) 0.0142(3) Uani d . . D 1 . .
C C11 0.7388(2) 0.6494(2) 0.6781(2) 0.0140(4) Uani d . . . 1 . .
C C12 0.6458(2) 0.6784(2) 0.6021(3) 0.0174(4) Uani d . . . 1 . .
I I13 0.49184(2) 0.72876(2) 0.47092(2) 0.01803(5) Uani d . . . 1 . .
H H14 0.965(3) 0.702(3) 0.893(3) 0.033(9) Uiso d . . D 1 . .
O O14 0.92617(15) 0.70819(14) 0.81479(19) 0.0161(3) Uani d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O10 . 1.440(2) ?
C1 C7 . 1.481(3) ?
C1 C2 . 1.532(3) ?
C1 C6 . 1.539(3) ?
C2 C3 . 1.525(3) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.533(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 O14 . 1.441(3) ?
C4 C11 . 1.479(3) ?
C4 C5 . 1.536(3) ?
C5 C6 . 1.529(3) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.188(3) ?
C8 I9 . 1.994(2) ?
I9 I13 4_566 3.9222(4) ?
O10 H10 . 0.80(3) ?
C11 C12 . 1.191(3) ?
C12 I13 . 2.002(2) ?
I13 C8 3_666 3.296(2) ?
I13 C7 3_666 3.354(2) ?
O14 H14 . 0.77(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O10 C1 C7 . . 107.35(17) ?
O10 C1 C2 . . 107.52(17) ?
C7 C1 C2 . . 109.68(18) ?
O10 C1 C6 . . 110.31(17) ?
C7 C1 C6 . . 112.47(17) ?
C2 C1 C6 . . 109.38(18) ?
C3 C2 C1 . . 111.57(18) ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2B . . 109.3 ?
C1 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108.0 ?
C2 C3 C4 . . 113.30(17) ?
C2 C3 H3A . . 108.9 ?
C4 C3 H3A . . 108.9 ?
C2 C3 H3B . . 108.9 ?
C4 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.7 ?
O14 C4 C11 . . 106.53(18) ?
O14 C4 C3 . . 109.67(17) ?
C11 C4 C3 . . 110.02(18) ?
O14 C4 C5 . . 109.40(17) ?
C11 C4 C5 . . 110.20(18) ?
C3 C4 C5 . . 110.92(18) ?
C6 C5 C4 . . 112.35(18) ?
C6 C5 H5A . . 109.1 ?
C4 C5 H5A . . 109.1 ?
C6 C5 H5B . . 109.1 ?
C4 C5 H5B . . 109.1 ?
H5A C5 H5B . . 107.9 ?
C5 C6 C1 . . 110.58(17) ?
C5 C6 H6A . . 109.5 ?
C1 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
C1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 108.1 ?
C8 C7 C1 . . 172.5(2) ?
C7 C8 I9 . . 176.7(2) ?
C8 I9 I13 . 4_566 140.69(7) ?
C1 O10 H10 . . 106.(2) ?
C12 C11 C4 . . 177.0(2) ?
C11 C12 I13 . . 178.6(2) ?
C12 I13 C8 . 3_666 168.69(8) ?
C12 I13 C7 . 3_666 170.34(8) ?
C8 I13 C7 3_666 3_666 20.55(6) ?
C4 O14 H14 . . 113.(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O10 C1 C2 C3 . . . . 62.7(2) ?
C7 C1 C2 C3 . . . . 179.09(17) ?
C6 C1 C2 C3 . . . . -57.1(2) ?
C1 C2 C3 C4 . . . . 54.0(2) ?
C2 C3 C4 O14 . . . . -171.41(17) ?
C2 C3 C4 C11 . . . . 71.7(2) ?
C2 C3 C4 C5 . . . . -50.5(2) ?
O14 C4 C5 C6 . . . . 173.19(17) ?
C11 C4 C5 C6 . . . . -70.0(2) ?
C3 C4 C5 C6 . . . . 52.1(2) ?
C4 C5 C6 C1 . . . . -57.1(2) ?
O10 C1 C6 C5 . . . . -59.3(2) ?
C7 C1 C6 C5 . . . . -179.16(18) ?
C2 C1 C6 C5 . . . . 58.7(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O10 H10 O14 2_746 0.80(3) 2.01(3) 2.806(2) 173.(3) ?
O14 H14 O10 3_767 0.77(3) 2.16(3) 2.922(2) 170.(3) ?

####################################################################### 
# 
# 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_D1A5
_database_code_depnum_ccdc_archive 'CCDC 1820025'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H10 I2 O2, C12 H12 N2'
_chemical_formula_sum            'C22 H22 I2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         600.21

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8440(14)
_cell_length_b                   11.568(2)
_cell_length_c                   12.755(2)
_cell_angle_alpha                92.124(6)
_cell_angle_beta                 97.154(6)
_cell_angle_gamma                109.722(6)
_cell_volume                     1077.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.52
_cell_measurement_temperature    120.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580

_exptl_absorpt_coefficient_mu    2.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_T_max  0.80

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            22664
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             6403
_reflns_number_gt                5625
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0734
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.037
_refine_ls_number_reflns         6403
_refine_ls_number_parameters     296
_refine_ls_number_restraints     90
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+1.7057P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.735
_refine_diff_density_min         -1.034
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_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'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C11 -0.2177(3) 0.1235(2) 0.7029(2) 0.0155(5) Uani d . . . 1.0 . .
O O11 -0.3800(2) 0.14212(19) 0.65594(15) 0.0191(4) Uani d . . . 1.0 . .
H H11 -0.364 0.1708 0.597 0.023 Uiso calc U . R 1.0 . .
C C12 -0.0573(4) 0.2468(3) 0.7228(2) 0.0180(5) Uani d . . . 1.0 . .
H H12A -0.0404 0.2855 0.6551 0.022 Uiso calc U . R 1.0 . .
H H12B -0.0863 0.3031 0.7723 0.022 Uiso calc U . R 1.0 . .
C C13 0.1196(4) 0.2286(3) 0.7694(2) 0.0184(5) Uani d . . . 1.0 . .
H H13A 0.1055 0.1961 0.8397 0.022 Uiso calc U . R 1.0 . .
H H13B 0.2202 0.3093 0.7797 0.022 Uiso calc U . R 1.0 . .
C C14 0.1709(3) 0.1395(3) 0.6980(2) 0.0182(5) Uani d . . . 1.0 . .
O O14 0.3219(3) 0.1165(2) 0.75651(16) 0.0253(5) Uani d . . . 1.0 . .
H H14 0.4036 0.1236 0.7179 0.03 Uiso calc U . R 1.0 . .
C C15 0.0104(4) 0.0176(3) 0.6742(2) 0.0181(5) Uani d . . . 1.0 . .
H H15A 0.0401 -0.0361 0.6225 0.022 Uiso calc U . R 1.0 . .
H H15B -0.0062 -0.0246 0.7403 0.022 Uiso calc U . R 1.0 . .
C C16 -0.1685(4) 0.0343(2) 0.6298(2) 0.0169(5) Uani d . . . 1.0 . .
H H16A -0.2683 -0.0468 0.6206 0.02 Uiso calc U . R 1.0 . .
H H16B -0.1576 0.0665 0.5592 0.02 Uiso calc U . R 1.0 . .
C C21 -0.2517(3) 0.0721(3) 0.8051(2) 0.0181(5) Uani d . . . 1.0 . .
C C22 -0.2580(4) 0.0349(3) 0.8917(2) 0.0209(5) Uani d . . . 1.0 . .
I I1 -0.27074(2) -0.02594(2) 1.03645(2) 0.02103(6) Uani d . . . 1.0 . .
C C31 0.2175(4) 0.1972(3) 0.5997(2) 0.0191(5) Uani d . . . 1.0 . .
C C32 0.2397(4) 0.2486(3) 0.5198(2) 0.0205(5) Uani d . . . 1.0 . .
I I2 0.26393(2) 0.33295(2) 0.38425(2) 0.01993(5) Uani d . . . 1.0 . .
N N41A 0.2977(11) 0.4489(6) 0.1987(4) 0.0257(18) Uani d . P D 0.681(4) A 1
C C42A 0.2311(16) 0.3877(5) 0.1040(5) 0.049(3) Uani d . P D 0.681(4) A 1
H H42A 0.1774 0.3005 0.1003 0.059 Uiso calc U P R 0.681(4) A 1
C C43A 0.2359(10) 0.4446(4) 0.0105(4) 0.0415(17) Uani d . P D 0.681(4) A 1
H H43A 0.1902 0.397 -0.0558 0.05 Uiso calc U P R 0.681(4) A 1
C C44A 0.3083(8) 0.5719(4) 0.0147(3) 0.0331(11) Uani d . P D 0.681(4) A 1
C C45A 0.3714(7) 0.6358(4) 0.1137(3) 0.0232(11) Uani d . P D 0.681(4) A 1
H H45A 0.4219 0.7233 0.12 0.028 Uiso calc U P R 0.681(4) A 1
C C46A 0.361(2) 0.5721(6) 0.2025(4) 0.0223(10) Uani d . P D 0.681(4) A 1
H H46A 0.3994 0.6175 0.27 0.027 Uiso calc U P R 0.681(4) A 1
C C47A 0.3103(9) 0.6453(5) -0.0824(3) 0.0464(14) Uani d . P D 0.681(4) A 1
H H47A 0.2459 0.7039 -0.0706 0.056 Uiso calc U P R 0.681(4) A 1
H H47B 0.4391 0.6946 -0.0874 0.056 Uiso calc U P R 0.681(4) A 1
N N41B 0.257(3) 0.4511(14) 0.2010(8) 0.0257(18) Uani d . P D 0.319(4) A 2
C C42B 0.174(4) 0.3787(10) 0.1130(11) 0.049(3) Uani d . P D 0.319(4) A 2
H H42B 0.1329 0.292 0.1168 0.059 Uiso calc U P R 0.319(4) A 2
C C43B 0.145(2) 0.4240(7) 0.0162(8) 0.0415(17) Uani d . P D 0.319(4) A 2
H H43B 0.0753 0.3697 -0.0436 0.05 Uiso calc U P R 0.319(4) A 2
C C44B 0.2172(17) 0.5496(7) 0.0076(6) 0.0331(11) Uani d . P D 0.319(4) A 2
C C45B 0.3174(18) 0.6237(9) 0.0974(7) 0.0232(11) Uani d . P D 0.319(4) A 2
H H45B 0.368 0.7105 0.0951 0.028 Uiso calc U P R 0.319(4) A 2
C C46B 0.343(5) 0.5707(14) 0.1896(9) 0.0223(10) Uani d . P D 0.319(4) A 2
H H46B 0.4252 0.6209 0.248 0.027 Uiso calc U P R 0.319(4) A 2
C C47B 0.1840(19) 0.6096(10) -0.0940(7) 0.0464(14) Uani d . P D 0.319(4) A 2
H H47C 0.1816 0.6932 -0.0771 0.056 Uiso calc U P R 0.319(4) A 2
H H47D 0.0658 0.5595 -0.1367 0.056 Uiso calc U P R 0.319(4) A 2
N N51A 0.297(4) 0.7626(8) -0.4688(5) 0.0181(15) Uani d . P D 0.681(4) A 1
C C52A 0.331(3) 0.8272(6) -0.3754(6) 0.018(2) Uani d . P D 0.681(4) A 1
H H52A 0.3709 0.9145 -0.3738 0.021 Uiso calc U P R 0.681(4) A 1
C C53A 0.3114(9) 0.7734(4) -0.2806(5) 0.0252(14) Uani d . P D 0.681(4) A 1
H H53A 0.3404 0.8231 -0.2155 0.03 Uiso calc U P R 0.681(4) A 1
C C54A 0.2488(7) 0.6462(4) -0.2817(3) 0.0267(10) Uani d . P D 0.681(4) A 1
C C55A 0.2117(8) 0.5790(5) -0.3789(3) 0.0238(10) Uani d . P D 0.681(4) A 1
H H55A 0.1661 0.4914 -0.3833 0.029 Uiso calc U P R 0.681(4) A 1
C C56A 0.241(2) 0.6392(7) -0.4687(3) 0.0213(8) Uani d . P D 0.681(4) A 1
H H56A 0.2208 0.5916 -0.5343 0.026 Uiso calc U P R 0.681(4) A 1
C C57A 0.2291(8) 0.5754(5) -0.1827(4) 0.0420(12) Uani d . P D 0.681(4) A 1
H H57A 0.0969 0.5337 -0.1804 0.05 Uiso calc U P R 0.681(4) A 1
H H57B 0.2835 0.5103 -0.1906 0.05 Uiso calc U P R 0.681(4) A 1
N N51B 0.304(8) 0.7503(18) -0.4636(10) 0.0181(15) Uani d . P D 0.319(4) A 2
C C52B 0.356(6) 0.8286(13) -0.3771(13) 0.018(2) Uani d . P D 0.319(4) A 2
H H52B 0.3952 0.9145 -0.3855 0.021 Uiso calc U P R 0.319(4) A 2
C C53B 0.357(3) 0.7911(8) -0.2755(11) 0.0252(14) Uani d . P D 0.319(4) A 2
H H53B 0.3891 0.8499 -0.2159 0.03 Uiso calc U P R 0.319(4) A 2
C C54B 0.3094(15) 0.6666(8) -0.2617(7) 0.0267(10) Uani d . P D 0.319(4) A 2
C C55B 0.248(2) 0.5852(11) -0.3517(7) 0.0238(10) Uani d . P D 0.319(4) A 2
H H55B 0.2125 0.4989 -0.3458 0.029 Uiso calc U P R 0.319(4) A 2
C C56B 0.238(6) 0.6297(17) -0.4493(7) 0.0213(8) Uani d . P D 0.319(4) A 2
H H56B 0.1823 0.5728 -0.5097 0.026 Uiso calc U P R 0.319(4) A 2
C C57B 0.3456(17) 0.6161(10) -0.1553(7) 0.0420(12) Uani d . P D 0.319(4) A 2
H H57C 0.4626 0.6711 -0.1144 0.05 Uiso calc U P R 0.319(4) A 2
H H57D 0.3535 0.5331 -0.1668 0.05 Uiso calc U P R 0.319(4) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C11 O11 . 1.425(3) ?
C11 C21 . 1.471(4) ?
C11 C12 . 1.537(4) ?
C11 C16 . 1.540(4) ?
O11 H11 . 0.84 ?
C12 C13 . 1.525(4) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.535(4) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 O14 . 1.428(3) ?
C14 C31 . 1.470(4) ?
C14 C15 . 1.530(4) ?
O14 H14 . 0.84 ?
C15 C16 . 1.523(4) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C21 C22 . 1.201(4) ?
C22 I1 . 2.002(3) ?
I1 O14 2_557 2.901(2) ?
C31 C32 . 1.201(4) ?
C32 I2 . 2.014(3) ?
I2 N41B . 2.755(8) ?
I2 N41A . 2.761(4) ?
N41A C42A . 1.328(4) ?
N41A C46A . 1.339(4) ?
C42A C43A . 1.382(4) ?
C42A H42A . 0.95 ?
C43A C44A . 1.384(4) ?
C43A H43A . 0.95 ?
C44A C45A . 1.384(4) ?
C44A C47A . 1.527(4) ?
C45A C46A . 1.371(4) ?
C45A H45A . 0.95 ?
C46A H46A . 0.95 ?
C47A C57A . 1.439(7) ?
C47A H47A . 0.99 ?
C47A H47B . 0.99 ?
N41B C42B . 1.329(4) ?
N41B C46B . 1.341(5) ?
C42B C43B . 1.382(4) ?
C42B H42B . 0.95 ?
C43B C44B . 1.385(5) ?
C43B H43B . 0.95 ?
C44B C45B . 1.382(5) ?
C44B C47B . 1.527(5) ?
C45B C46B . 1.370(5) ?
C45B H45B . 0.95 ?
C46B H46B . 0.95 ?
C47B C57B . 1.553(19) ?
C47B H47C . 0.99 ?
C47B H47D . 0.99 ?
N51A C52A . 1.330(4) ?
N51A C56A . 1.344(4) ?
C52A C53A . 1.382(4) ?
C52A H52A . 0.95 ?
C53A C54A . 1.383(4) ?
C53A H53A . 0.95 ?
C54A C55A . 1.384(4) ?
C54A C57A . 1.526(4) ?
C55A C56A . 1.366(4) ?
C55A H55A . 0.95 ?
C56A H56A . 0.95 ?
C57A H57A . 0.99 ?
C57A H57B . 0.99 ?
N51B C52B . 1.330(4) ?
N51B C56B . 1.343(4) ?
C52B C53B . 1.382(4) ?
C52B H52B . 0.95 ?
C53B C54B . 1.385(5) ?
C53B H53B . 0.95 ?
C54B C55B . 1.383(5) ?
C54B C57B . 1.529(5) ?
C55B C56B . 1.368(5) ?
C55B H55B . 0.95 ?
C56B H56B . 0.95 ?
C57B H57C . 0.99 ?
C57B H57D . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 C11 C21 . . 107.9(2) ?
O11 C11 C12 . . 110.3(2) ?
C21 C11 C12 . . 108.9(2) ?
O11 C11 C16 . . 110.3(2) ?
C21 C11 C16 . . 110.3(2) ?
C12 C11 C16 . . 109.2(2) ?
C11 O11 H11 . . 109.5 ?
C13 C12 C11 . . 111.3(2) ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12B . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 112.3(2) ?
C12 C13 H13A . . 109.1 ?
C14 C13 H13A . . 109.1 ?
C12 C13 H13B . . 109.1 ?
C14 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.9 ?
O14 C14 C31 . . 112.2(2) ?
O14 C14 C15 . . 108.5(2) ?
C31 C14 C15 . . 111.0(2) ?
O14 C14 C13 . . 106.8(2) ?
C31 C14 C13 . . 108.5(2) ?
C15 C14 C13 . . 109.7(2) ?
C14 O14 H14 . . 109.5 ?
C16 C15 C14 . . 113.0(2) ?
C16 C15 H15A . . 109.0 ?
C14 C15 H15A . . 109.0 ?
C16 C15 H15B . . 109.0 ?
C14 C15 H15B . . 109.0 ?
H15A C15 H15B . . 107.8 ?
C15 C16 C11 . . 112.0(2) ?
C15 C16 H16A . . 109.2 ?
C11 C16 H16A . . 109.2 ?
C15 C16 H16B . . 109.2 ?
C11 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C22 C21 C11 . . 172.5(3) ?
C21 C22 I1 . . 179.3(3) ?
C22 I1 O14 . 2_557 175.12(9) ?
C32 C31 C14 . . 172.9(3) ?
C31 C32 I2 . . 177.3(2) ?
C32 I2 N41B . . 173.2(5) ?
C32 I2 N41A . . 179.9(2) ?
C42A N41A C46A . . 117.2(3) ?
C42A N41A I2 . . 122.3(3) ?
C46A N41A I2 . . 119.9(4) ?
N41A C42A C43A . . 123.3(3) ?
N41A C42A H42A . . 118.3 ?
C43A C42A H42A . . 118.3 ?
C42A C43A C44A . . 119.1(3) ?
C42A C43A H43A . . 120.5 ?
C44A C43A H43A . . 120.5 ?
C43A C44A C45A . . 117.6(3) ?
C43A C44A C47A . . 123.8(3) ?
C45A C44A C47A . . 118.4(3) ?
C46A C45A C44A . . 119.5(3) ?
C46A C45A H45A . . 120.2 ?
C44A C45A H45A . . 120.2 ?
N41A C46A C45A . . 123.1(4) ?
N41A C46A H46A . . 118.5 ?
C45A C46A H46A . . 118.5 ?
C57A C47A C44A . . 116.6(4) ?
C57A C47A H47A . . 108.1 ?
C44A C47A H47A . . 108.1 ?
C57A C47A H47B . . 108.1 ?
C44A C47A H47B . . 108.1 ?
H47A C47A H47B . . 107.3 ?
C42B N41B C46B . . 116.8(5) ?
C42B N41B I2 . . 115.7(7) ?
C46B N41B I2 . . 127.2(6) ?
N41B C42B C43B . . 122.9(5) ?
N41B C42B H42B . . 118.5 ?
C43B C42B H42B . . 118.5 ?
C42B C43B C44B . . 119.1(4) ?
C42B C43B H43B . . 120.5 ?
C44B C43B H43B . . 120.5 ?
C45B C44B C43B . . 117.6(4) ?
C45B C44B C47B . . 119.1(5) ?
C43B C44B C47B . . 123.2(5) ?
C46B C45B C44B . . 119.4(4) ?
C46B C45B H45B . . 120.3 ?
C44B C45B H45B . . 120.3 ?
N41B C46B C45B . . 122.9(6) ?
N41B C46B H46B . . 118.6 ?
C45B C46B H46B . . 118.6 ?
C44B C47B C57B . . 105.9(10) ?
C44B C47B H47C . . 110.6 ?
C57B C47B H47C . . 110.6 ?
C44B C47B H47D . . 110.6 ?
C57B C47B H47D . . 110.6 ?
H47C C47B H47D . . 108.7 ?
C52A N51A C56A . . 117.1(3) ?
N51A C52A C53A . . 123.2(3) ?
N51A C52A H52A . . 118.4 ?
C53A C52A H52A . . 118.4 ?
C52A C53A C54A . . 119.2(3) ?
C52A C53A H53A . . 120.4 ?
C54A C53A H53A . . 120.4 ?
C55A C54A C53A . . 117.6(3) ?
C55A C54A C57A . . 117.8(3) ?
C53A C54A C57A . . 124.5(4) ?
C56A C55A C54A . . 119.6(3) ?
C56A C55A H55A . . 120.2 ?
C54A C55A H55A . . 120.2 ?
N51A C56A C55A . . 123.3(4) ?
N51A C56A H56A . . 118.4 ?
C55A C56A H56A . . 118.4 ?
C47A C57A C54A . . 117.0(4) ?
C47A C57A H57A . . 108.0 ?
C54A C57A H57A . . 108.0 ?
C47A C57A H57B . . 108.0 ?
C54A C57A H57B . . 108.0 ?
H57A C57A H57B . . 107.3 ?
C52B N51B C56B . . 117.0(4) ?
N51B C52B C53B . . 123.2(4) ?
N51B C52B H52B . . 118.4 ?
C53B C52B H52B . . 118.4 ?
C52B C53B C54B . . 119.1(4) ?
C52B C53B H53B . . 120.4 ?
C54B C53B H53B . . 120.4 ?
C55B C54B C53B . . 117.5(4) ?
C55B C54B C57B . . 118.4(5) ?
C53B C54B C57B . . 123.6(5) ?
C56B C55B C54B . . 119.6(4) ?
C56B C55B H55B . . 120.2 ?
C54B C55B H55B . . 120.2 ?
N51B C56B C55B . . 123.0(6) ?
N51B C56B H56B . . 118.5 ?
C55B C56B H56B . . 118.5 ?
C54B C57B C47B . . 107.4(10) ?
C54B C57B H57C . . 110.2 ?
C47B C57B H57C . . 110.2 ?
C54B C57B H57D . . 110.2 ?
C47B C57B H57D . . 110.2 ?
H57C C57B H57D . . 108.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O11 C11 C12 C13 . . . . -178.0(2) ?
C21 C11 C12 C13 . . . . 63.9(3) ?
C16 C11 C12 C13 . . . . -56.6(3) ?
C11 C12 C13 C14 . . . . 57.6(3) ?
C12 C13 C14 O14 . . . . -171.8(2) ?
C12 C13 C14 C31 . . . . 67.0(3) ?
C12 C13 C14 C15 . . . . -54.4(3) ?
O14 C14 C15 C16 . . . . 169.5(2) ?
C31 C14 C15 C16 . . . . -66.7(3) ?
C13 C14 C15 C16 . . . . 53.1(3) ?
C14 C15 C16 C11 . . . . -55.1(3) ?
O11 C11 C16 C15 . . . . 176.7(2) ?
C21 C11 C16 C15 . . . . -64.2(3) ?
C12 C11 C16 C15 . . . . 55.3(3) ?
C46A N41A C42A C43A . . . . 4.7(17) ?
I2 N41A C42A C43A . . . . 175.7(7) ?
N41A C42A C43A C44A . . . . -2.1(15) ?
C42A C43A C44A C45A . . . . -0.4(11) ?
C42A C43A C44A C47A . . . . -176.1(8) ?
C43A C44A C45A C46A . . . . 0.1(12) ?
C47A C44A C45A C46A . . . . 176.0(11) ?
C42A N41A C46A C45A . . . . -5.(2) ?
I2 N41A C46A C45A . . . . -176.3(11) ?
C44A C45A C46A N41A . . . . 3.(2) ?
C43A C44A C47A C57A . . . . 0.8(10) ?
C45A C44A C47A C57A . . . . -174.8(6) ?
C46B N41B C42B C43B . . . . -12.(4) ?
I2 N41B C42B C43B . . . . 174.(2) ?
N41B C42B C43B C44B . . . . 5.(4) ?
C42B C43B C44B C45B . . . . 0.(3) ?
C42B C43B C44B C47B . . . . -177.(2) ?
C43B C44B C45B C46B . . . . 1.(3) ?
C47B C44B C45B C46B . . . . 178.(2) ?
C42B N41B C46B C45B . . . . 13.(5) ?
I2 N41B C46B C45B . . . . -173.(2) ?
C44B C45B C46B N41B . . . . -8.(5) ?
C45B C44B C47B C57B . . . . 90.6(14) ?
C43B C44B C47B C57B . . . . -92.5(15) ?
C56A N51A C52A C53A . . . . 0.(3) ?
N51A C52A C53A C54A . . . . -2.(2) ?
C52A C53A C54A C55A . . . . 1.0(12) ?
C52A C53A C54A C57A . . . . 177.0(10) ?
C53A C54A C55A C56A . . . . 1.3(12) ?
C57A C54A C55A C56A . . . . -175.0(10) ?
C52A N51A C56A C55A . . . . 2.(3) ?
C54A C55A C56A N51A . . . . -3.(2) ?
C44A C47A C57A C54A . . . . -173.5(5) ?
C55A C54A C57A C47A . . . . 164.9(6) ?
C53A C54A C57A C47A . . . . -11.1(9) ?
C56B N51B C52B C53B . . . . 4.(8) ?
N51B C52B C53B C54B . . . . 3.(6) ?
C52B C53B C54B C55B . . . . -6.(3) ?
C52B C53B C54B C57B . . . . 166.(3) ?
C53B C54B C55B C56B . . . . 1.(3) ?
C57B C54B C55B C56B . . . . -171.(2) ?
C52B N51B C56B C55B . . . . -10.(7) ?
C54B C55B C56B N51B . . . . 7.(5) ?
C55B C54B C57B C47B . . . . -103.9(13) ?
C53B C54B C57B C47B . . . . 84.7(16) ?
C44B C47B C57B C54B . . . . 175.7(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O11 H11 N51A 2_565 0.84 1.89 2.726(7) 172.9 ?
O11 H11 N51B 2_565 0.84 1.99 2.831(12) 174.7 ?
O14 H14 O11 1_655 0.84 1.91 2.740(3) 168.7 ?

####################################################################### 
# 
# 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_D3
_database_code_depnum_ccdc_archive 'CCDC 1820022'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H12 O2, H2 O'
_chemical_formula_sum            'C10 H14 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         182.21

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.9472(12)
_cell_length_b                   6.1399(8)
_cell_length_c                   16.775(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.248(2)
_cell_angle_gamma                90
_cell_volume                     993.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3945
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      31.47
_cell_measurement_temperature    228.(2)

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.230
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      228.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            13268
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         33.54
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             3686
_reflns_number_gt                2678
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1308
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         3686
_refine_ls_number_parameters     134
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+0.1449P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker SMART'
_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'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.50902(9) 0.00439(15) 0.41255(6) 0.02059(18) Uani d . . . 1 . .
C C2 0.45885(10) 0.20167(15) 0.45291(6) 0.02248(19) Uani d . . . 1 . .
H H2A 0.5376 0.2984 0.475 0.027 Uiso calc U . R 1 . .
H H2B 0.3909 0.2829 0.4113 0.027 Uiso calc U . R 1 . .
C C3 0.39292(10) 0.13397(16) 0.52204(6) 0.02259(19) Uani d . . . 1 . .
H H3A 0.3083 0.0506 0.4988 0.027 Uiso calc U . R 1 . .
H H3B 0.3665 0.2647 0.5481 0.027 Uiso calc U . R 1 . .
H H4 0.6036(16) -0.025(3) 0.3271(10) 0.050(4) Uiso d . . D 1 . .
O O4 0.58076(8) 0.09004(12) 0.35457(4) 0.02596(17) Uani d . . D 1 . .
C C5 0.39192(11) -0.13246(17) 0.36800(6) 0.0250(2) Uani d . . . 1 . .
C C6 0.30239(13) -0.2490(2) 0.33179(8) 0.0373(3) Uani d . . . 1 . .
H H6 0.2314 -0.3413 0.3031 0.045 Uiso calc U . R 1 . .
C C7 0.89997(10) 0.42927(17) 0.42229(7) 0.0252(2) Uani d . . . 1 . .
C C8 0.90416(10) 0.32308(17) 0.50530(7) 0.0280(2) Uani d . . . 1 . .
H H8A 0.8367 0.3954 0.5302 0.034 Uiso calc U . R 1 . .
H H8B 0.8769 0.1699 0.4965 0.034 Uiso calc U . R 1 . .
C C9 1.04730(11) 0.33570(17) 0.56447(7) 0.0276(2) Uani d . . . 1 . .
H H9A 1.1128 0.2492 0.5426 0.033 Uiso calc U . R 1 . .
H H9B 1.0431 0.2728 0.6175 0.033 Uiso calc U . R 1 . .
H H10 0.7225(18) 0.320(3) 0.3735(11) 0.054(5) Uiso d . . . 1 . .
O O10 0.75980(8) 0.44430(14) 0.37429(5) 0.03216(19) Uani d . . . 1 . .
C C11 0.98483(12) 0.3047(2) 0.37689(7) 0.0351(3) Uani d . . . 1 . .
C C12 1.05492(17) 0.2096(3) 0.34115(10) 0.0569(4) Uani d . . . 1 . .
H H12 1.1108 0.1338 0.3127 0.068 Uiso calc U . R 1 . .
H H13A 0.6870(17) 0.660(3) 0.2952(10) 0.050(5) Uiso d . . . 1 . .
H H13B 0.575(2) 0.727(3) 0.2338(13) 0.064(5) Uiso d . . . 1 . .
O O13 0.65293(10) 0.77613(14) 0.26652(5) 0.0339(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O4 . 1.4399(11) ?
C1 C5 . 1.4808(14) ?
C1 C2 . 1.5300(13) ?
C1 C3 3_656 1.5332(13) ?
C2 C3 . 1.5237(14) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C3 C1 3_656 1.5331(13) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
O4 H4 . 0.902(15) ?
C5 C6 . 1.1864(15) ?
C6 H6 . 0.94 ?
C7 O10 . 1.4312(12) ?
C7 C11 . 1.4814(16) ?
C7 C8 . 1.5289(15) ?
C7 C9 3_766 1.5328(14) ?
C8 C9 . 1.5241(14) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C9 C7 3_766 1.5328(14) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
O10 H10 . 0.845(19) ?
C11 C12 . 1.1798(19) ?
C12 H12 . 0.94 ?
O13 H13A . 0.881(19) ?
O13 H13B . 0.88(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 C1 C5 . . 108.99(8) ?
O4 C1 C2 . . 106.24(8) ?
C5 C1 C2 . . 111.77(8) ?
O4 C1 C3 . 3_656 110.61(7) ?
C5 C1 C3 . 3_656 109.25(8) ?
C2 C1 C3 . 3_656 109.95(8) ?
C3 C2 C1 . . 111.67(8) ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2B . . 109.3 ?
C1 C2 H2B . . 109.3 ?
H2A C2 H2B . . 107.9 ?
C2 C3 C1 . 3_656 112.25(8) ?
C2 C3 H3A . . 109.2 ?
C1 C3 H3A 3_656 . 109.2 ?
C2 C3 H3B . . 109.2 ?
C1 C3 H3B 3_656 . 109.2 ?
H3A C3 H3B . . 107.9 ?
C1 O4 H4 . . 106.7(10) ?
C6 C5 C1 . . 177.00(12) ?
C5 C6 H6 . . 180.0 ?
O10 C7 C11 . . 110.09(9) ?
O10 C7 C8 . . 110.14(8) ?
C11 C7 C8 . . 110.91(9) ?
O10 C7 C9 . 3_766 105.79(8) ?
C11 C7 C9 . 3_766 110.04(9) ?
C8 C7 C9 . 3_766 109.75(9) ?
C9 C8 C7 . . 112.53(8) ?
C9 C8 H8A . . 109.1 ?
C7 C8 H8A . . 109.1 ?
C9 C8 H8B . . 109.1 ?
C7 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
C8 C9 C7 . 3_766 111.95(8) ?
C8 C9 H9A . . 109.2 ?
C7 C9 H9A 3_766 . 109.2 ?
C8 C9 H9B . . 109.2 ?
C7 C9 H9B 3_766 . 109.2 ?
H9A C9 H9B . . 107.9 ?
C7 O10 H10 . . 108.3(12) ?
C12 C11 C7 . . 178.29(15) ?
C11 C12 H12 . . 180.0 ?
H13A O13 H13B . . 102.8(16) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O4 C1 C2 C3 . . . . -174.43(7) ?
C5 C1 C2 C3 . . . . 66.79(10) ?
C3 C1 C2 C3 3_656 . . . -54.71(11) ?
C1 C2 C3 C1 . . . 3_656 56.00(11) ?
O10 C7 C8 C9 . . . . -170.70(9) ?
C11 C7 C8 C9 . . . . 67.17(12) ?
C9 C7 C8 C9 3_766 . . . -54.63(13) ?
C7 C8 C9 C7 . . . 3_766 55.83(13) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H4 O13 1_545 0.902(15) 1.736(15) 2.6333(11) 173.2(16) ?
O10 H10 O4 . 0.845(19) 1.967(19) 2.7789(11) 160.8(17) ?
O13 H13A O10 . 0.881(19) 1.887(19) 2.7575(13) 168.9(16) ?
O13 H13B O4 2_655 0.88(2) 2.05(2) 2.9174(12) 169.3(18) ?

####################################################################### 
# 
# 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_D2A3
_database_code_depnum_ccdc_archive 'CCDC 1820026'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

#_audit_creation_method            SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 I2 O2, C10 H8 N2'
_chemical_formula_sum            'C20 H18 I2 N2 O2'
_chemical_formula_weight         572.16

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                   9.5108(4)
_cell_length_b                   10.5838(6)
_cell_length_c                   22.0298(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.451(4)
_cell_angle_gamma                90
_cell_volume                     2180.74(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2707
_cell_measurement_theta_min      4.7170
_cell_measurement_theta_max      30.1890

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_F_000             1096
_exptl_absorpt_coefficient_mu    2.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.45793
_exptl_absorpt_correction_T_max  1.00000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurment_method        '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10597
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         4.358
_diffrn_reflns_theta_max         26.998
_reflns_number_total             4769
_reflns_number_gt                3558
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_structure_solution    
;
SHELXS-2014/7 (Sheldrick, 2014)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
;
_computing_molecular_graphics    
;
Mercury (Bruno et al., 2002)
;
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2013) and PLATON (Spek, 2003)
;

_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)+(0.0694P)²+6.4725P] 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     SHELXL
_refine_ls_extinction_coef       0.0077(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4750
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
I1 I 0.48323(6) 0.20225(5) 0.56388(2) 0.0607(2) Uani 1 1 d . . . . .
I2 I -0.14648(5) 0.29660(5) 0.26726(3) 0.0691(2) Uani 1 1 d . . . . .
O1 O 0.6305(4) 0.3014(5) 0.3448(2) 0.0445(10) Uani 1 1 d . . . . .
O2 O 0.3277(5) 0.3485(5) 0.16713(19) 0.0494(11) Uani 1 1 d . . . . .
N1 N 0.7750(6) 0.4899(5) 0.4217(3) 0.0591(15) Uani 1 1 d . . . . .
N2 N 1.1217(7) 0.9870(5) 0.6045(3) 0.0588(14) Uani 1 1 d . . . . .
C1 C 0.4978(7) 0.2368(6) 0.4761(3) 0.0456(14) Uani 1 1 d . . . . .
C2 C 0.4939(6) 0.2589(6) 0.4229(3) 0.0418(13) Uani 1 1 d . . . . .
C3 C 0.4892(6) 0.2871(5) 0.3567(2) 0.0352(11) Uani 1 1 d . . . . .
C4 C 0.4022(6) 0.4088(5) 0.3390(3) 0.0411(12) Uani 1 1 d . . . . .
H4A H 0.3082 0.3999 0.3498 0.049 Uiso 1 1 calc R U . . .
H4B H 0.4499 0.4795 0.3621 0.049 Uiso 1 1 calc R U . . .
C5 C 0.3865(6) 0.4349(5) 0.2699(3) 0.0394(12) Uani 1 1 d . . . . .
H5A H 0.3277 0.5095 0.2598 0.047 Uiso 1 1 calc R U . . .
H5B H 0.4801 0.4528 0.2603 0.047 Uiso 1 1 calc R U . . .
C6 C 0.3196(6) 0.3251(5) 0.2296(2) 0.0357(11) Uani 1 1 d . . . . .
C7 C 0.4038(6) 0.2055(5) 0.2483(2) 0.0358(11) Uani 1 1 d . . . . .
H7A H 0.4977 0.2135 0.2373 0.043 Uiso 1 1 calc R U . . .
H7B H 0.3556 0.1350 0.2252 0.043 Uiso 1 1 calc R U . . .
C8 C 0.4217(6) 0.1766(5) 0.3176(3) 0.0390(12) Uani 1 1 d . . . . .
H8A H 0.3289 0.1583 0.3279 0.047 Uiso 1 1 calc R U . . .
H8B H 0.4813 0.1023 0.3271 0.047 Uiso 1 1 calc R U . . .
C9 C 0.1685(6) 0.3107(6) 0.2375(3) 0.0419(13) Uani 1 1 d . . . . .
C10 C 0.0489(7) 0.3029(6) 0.2451(3) 0.0517(15) Uani 1 1 d . . . . .
C11 C 0.7647(7) 0.5036(7) 0.4808(4) 0.0611(18) Uani 1 1 d . . . . .
H11 H 0.7101 0.4453 0.4979 0.073 Uiso 1 1 calc R U . . .
C12 C 0.8300(7) 0.5988(6) 0.5179(3) 0.0539(16) Uani 1 1 d . . . . .
H12 H 0.8199 0.6035 0.5590 0.065 Uiso 1 1 calc R U . . .
C13 C 0.9113(6) 0.6880(5) 0.4934(3) 0.0424(13) Uani 1 1 d . . . . .
C14 C 0.9229(7) 0.6731(6) 0.4327(3) 0.0481(14) Uani 1 1 d . . . . .
H14 H 0.9770 0.7297 0.4142 0.058 Uiso 1 1 calc R U . . .
C15 C 0.8539(8) 0.5736(7) 0.3990(3) 0.0575(17) Uani 1 1 d . . . . .
H15 H 0.8638 0.5653 0.3580 0.069 Uiso 1 1 calc R U . . .
C16 C 0.9834(6) 0.7926(5) 0.5320(3) 0.0428(13) Uani 1 1 d . . . . .
C17 C 0.9189(8) 0.8541(7) 0.5749(3) 0.0591(17) Uani 1 1 d . . . . .
H17 H 0.8272 0.8315 0.5800 0.071 Uiso 1 1 calc R U . . .
C18 C 0.9908(9) 0.9488(7) 0.6098(3) 0.0652(19) Uani 1 1 d . . . . .
H18 H 0.9461 0.9886 0.6388 0.078 Uiso 1 1 calc R U . . .
C19 C 1.1812(7) 0.9296(7) 0.5635(4) 0.0586(18) Uani 1 1 d . . . . .
H19 H 1.2729 0.9548 0.5596 0.070 Uiso 1 1 calc R U . . .
C20 C 1.1179(7) 0.8333(6) 0.5251(3) 0.0552(17) Uani 1 1 d . . . . .
H20 H 1.1644 0.7975 0.4956 0.066 Uiso 1 1 calc R U . . .
H2O H 0.267(8) 0.391(7) 0.149(3) 0.05(2) Uiso 1 1 d . . . . .
H1O H 0.674(9) 0.356(9) 0.360(4) 0.08(3) Uiso 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
I1 C1 1.998(6) . ?
I1 O2 2.978(4) 4_566 ?
I2 C10 2.006(6) . ?
I2 O1 2.955(4) 1_455 ?
O1 C3 1.423(6) . ?
O1 H1O 0.75(9) . ?
O2 C6 1.414(6) . ?
O2 H2O 0.79(7) . ?
N1 C15 1.316(10) . ?
N1 C11 1.332(10) . ?
N2 C19 1.302(9) . ?
N2 C18 1.334(9) . ?
C1 C2 1.188(8) . ?
C2 C3 1.481(8) . ?
C3 C8 1.523(7) . ?
C3 C4 1.542(8) . ?
C4 C5 1.529(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.529(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.486(8) . ?
C6 C7 1.515(7) . ?
C7 C8 1.538(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.183(8) . ?
C11 C12 1.372(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(9) . ?
C13 C16 1.486(8) . ?
C14 C15 1.383(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.380(9) . ?
C16 C20 1.384(9) . ?
C17 C18 1.369(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.390(9) . ?
C19 H19 0.9300 . ?
C20 H20 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 I1 O2 154.6(2) . 4_566 ?
C10 I2 O1 159.0(2) . 1_455 ?
C3 O1 H1O 118(7) . . ?
C6 O2 H2O 116(5) . . ?
C15 N1 C11 116.4(6) . . ?
C19 N2 C18 116.7(6) . . ?
C2 C1 I1 174.3(6) . . ?
C1 C2 C3 179.7(7) . . ?
O1 C3 C2 110.1(4) . . ?
O1 C3 C8 107.0(4) . . ?
C2 C3 C8 109.6(5) . . ?
O1 C3 C4 110.2(4) . . ?
C2 C3 C4 109.6(5) . . ?
C8 C3 C4 110.3(4) . . ?
C5 C4 C3 110.7(4) . . ?
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 . . ?
C6 C5 C4 113.3(4) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O2 C6 C9 110.8(4) . . ?
O2 C6 C7 106.9(4) . . ?
C9 C6 C7 110.9(5) . . ?
O2 C6 C5 110.0(5) . . ?
C9 C6 C5 108.6(5) . . ?
C7 C6 C5 109.5(4) . . ?
C6 C7 C8 113.2(4) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C3 C8 C7 111.7(4) . . ?
C3 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C3 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C6 177.6(7) . . ?
C9 C10 I2 173.9(6) . . ?
N1 C11 C12 123.9(7) . . ?
N1 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C11 C12 C13 119.4(7) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 116.7(6) . . ?
C14 C13 C16 122.3(6) . . ?
C12 C13 C16 121.0(6) . . ?
C13 C14 C15 119.7(6) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
N1 C15 C14 123.9(7) . . ?
N1 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
C17 C16 C20 117.6(6) . . ?
C17 C16 C13 121.8(6) . . ?
C20 C16 C13 120.6(6) . . ?
C18 C17 C16 119.4(7) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
N2 C18 C17 123.5(7) . . ?
N2 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
N2 C19 C20 124.8(7) . . ?
N2 C19 H19 117.6 . . ?
C20 C19 H19 117.6 . . ?
C16 C20 C19 117.9(7) . . ?
C16 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?

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 C3 C4 C5 62.8(6) . . . . ?
C2 C3 C4 C5 -175.9(5) . . . . ?
C8 C3 C4 C5 -55.1(6) . . . . ?
C3 C4 C5 C6 56.0(6) . . . . ?
C4 C5 C6 O2 -171.5(4) . . . . ?
C4 C5 C6 C9 67.0(6) . . . . ?
C4 C5 C6 C7 -54.3(6) . . . . ?
O2 C6 C7 C8 172.5(4) . . . . ?
C9 C6 C7 C8 -66.5(6) . . . . ?
C5 C6 C7 C8 53.4(6) . . . . ?
O1 C3 C8 C7 -65.0(6) . . . . ?
C2 C3 C8 C7 175.6(5) . . . . ?
C4 C3 C8 C7 54.8(6) . . . . ?
C6 C7 C8 C3 -55.4(6) . . . . ?
C15 N1 C11 C12 0.4(11) . . . . ?
N1 C11 C12 C13 0.6(11) . . . . ?
C11 C12 C13 C14 -1.1(9) . . . . ?
C11 C12 C13 C16 179.9(6) . . . . ?
C12 C13 C14 C15 0.7(9) . . . . ?
C16 C13 C14 C15 179.7(6) . . . . ?
C11 N1 C15 C14 -0.8(10) . . . . ?
C13 C14 C15 N1 0.3(11) . . . . ?
C14 C13 C16 C17 141.9(7) . . . . ?
C12 C13 C16 C17 -39.1(9) . . . . ?
C14 C13 C16 C20 -36.8(9) . . . . ?
C12 C13 C16 C20 142.2(7) . . . . ?
C20 C16 C17 C18 -2.1(10) . . . . ?
C13 C16 C17 C18 179.2(6) . . . . ?
C19 N2 C18 C17 0.1(12) . . . . ?
C16 C17 C18 N2 0.7(12) . . . . ?
C18 N2 C19 C20 0.6(11) . . . . ?
C17 C16 C20 C19 2.7(10) . . . . ?
C13 C16 C20 C19 -178.6(6) . . . . ?
N2 C19 C20 C16 -2.1(11) . . . . ?

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
C19 H19 I1 0.93 3.29 4.071(7) 143.2 1_665
O2 H2O N2 0.79(7) 2.01(7) 2.791(7) 174(7) 4_475
O1 H1O N1 0.75(9) 2.08(9) 2.810(7) 165(9) .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.259
_refine_diff_density_min         -1.564
_refine_diff_density_rms         0.116

_shelxl_version_number           2014-7

####################################################################### 
# 
# 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_D1A3
_database_code_depnum_ccdc_archive 'CCDC 1820023'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H10 I2 O2, C10 H8 N2'
_chemical_formula_sum            'C20 H18 I2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         572.16

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7674(8)
_cell_length_b                   10.0010(10)
_cell_length_c                   26.238(3)
_cell_angle_alpha                81.2340(10)
_cell_angle_beta                 89.2680(10)
_cell_angle_gamma                85.8440(10)
_cell_volume                     2009.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      32.28
_cell_measurement_temperature    228.(2)

_exptl_crystal_description       Irregular
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096

_exptl_absorpt_coefficient_mu    3.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  0.60

_exptl_special_details           
;
;

_diffrn_ambient_temperature      228.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_rdiation_source          'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            27960
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         33.46
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       40

_refine_special_details          
;
;

_reflns_number_total             14217
_reflns_number_gt                10970
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1070
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.149
_refine_ls_number_reflns         14217
_refine_ls_number_parameters     482
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+10.3254P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.433
_refine_diff_density_min         -1.219
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker SMART'
_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'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.0874(6) 0.7647(5) 0.40316(18) 0.0223(9) Uani d . . . 1 . .
C C2 0.0280(6) 0.8778(5) 0.38043(17) 0.0211(8) Uani d . . . 1 . .
H H2A 0.0389 0.8788 0.3431 0.025 Uiso calc U . R 1 . .
H H2B -0.0268 0.9657 0.3862 0.025 Uiso calc U . R 1 . .
C C3 0.2063(6) 0.8586(5) 0.40448(17) 0.0203(8) Uani d . . . 1 . .
H H3A 0.1963 0.8662 0.4412 0.024 Uiso calc U . R 1 . .
H H3B 0.2766 0.9307 0.3881 0.024 Uiso calc U . R 1 . .
C C4 0.2970(6) 0.7201(5) 0.39852(16) 0.0198(8) Uani d . . . 1 . .
C C5 0.1841(6) 0.6074(5) 0.42253(18) 0.0218(9) Uani d . . . 1 . .
H H5A 0.2391 0.5192 0.4172 0.026 Uiso calc U . R 1 . .
H H5B 0.1747 0.6082 0.4598 0.026 Uiso calc U . R 1 . .
C C6 0.0035(6) 0.6252(5) 0.39885(18) 0.0233(9) Uani d . . . 1 . .
H H6A -0.0664 0.5542 0.4163 0.028 Uiso calc U . R 1 . .
H H6B 0.0124 0.6143 0.3624 0.028 Uiso calc U . R 1 . .
H H7 -0.338(7) 0.754(9) 0.381(3) 0.09(3) Uiso d . . D 1 . .
O O7 -0.2429(4) 0.7872(4) 0.37247(14) 0.0302(8) Uani d . . D 1 . .
C C8 -0.1237(6) 0.7739(5) 0.45794(19) 0.0257(10) Uani d . . . 1 . .
C C9 -0.1333(7) 0.7751(5) 0.50306(19) 0.0273(10) Uani d . . . 1 . .
I I10 -0.13933(4) 0.77350(3) 0.58019(2) 0.02483(7) Uani d . . . 1 . .
H H11 0.461(10) 0.726(8) 0.4539(18) 0.07(3) Uiso d . . D 1 . .
O O11 0.4620(4) 0.7034(4) 0.42349(13) 0.0244(7) Uani d . . D 1 . .
C C12 0.3228(6) 0.7136(5) 0.34328(17) 0.0232(9) Uani d . . . 1 . .
C C13 0.3173(6) 0.7177(6) 0.29744(19) 0.0291(11) Uani d . . . 1 . .
I I14 0.29567(4) 0.73556(4) 0.22037(2) 0.02825(8) Uani d . . . 1 . .
C C15 0.7972(6) 0.7343(5) 0.08708(17) 0.0214(9) Uani d . . . 1 . .
C C16 0.7018(6) 0.8702(5) 0.06428(18) 0.0233(9) Uani d . . . 1 . .
H H16A 0.7674 0.9448 0.0719 0.028 Uiso calc U . R 1 . .
H H16B 0.6958 0.8759 0.0267 0.028 Uiso calc U . R 1 . .
C C17 0.5195(6) 0.8862(5) 0.08582(19) 0.0229(9) Uani d . . . 1 . .
H H17A 0.4619 0.9713 0.0687 0.027 Uiso calc U . R 1 . .
H H17B 0.526 0.8917 0.1227 0.027 Uiso calc U . R 1 . .
C C18 0.4123(6) 0.7688(5) 0.07828(16) 0.0201(8) Uani d . . . 1 . .
C C19 0.5083(6) 0.6324(5) 0.09944(18) 0.0244(9) Uani d . . . 1 . .
H H19A 0.5147 0.6236 0.1371 0.029 Uiso calc U . R 1 . .
H H19B 0.4427 0.5586 0.091 0.029 Uiso calc U . R 1 . .
C C20 0.6899(6) 0.6181(5) 0.07763(19) 0.0247(9) Uani d . . . 1 . .
H H20A 0.6832 0.6165 0.0405 0.03 Uiso calc U . R 1 . .
H H20B 0.7475 0.5317 0.0937 0.03 Uiso calc U . R 1 . .
H H21 0.959(10) 0.738(8) 0.0299(14) 0.06(2) Uiso d . . D 1 . .
O O21 0.9649(4) 0.7198(4) 0.06412(13) 0.0293(8) Uani d . . D 1 . .
C C22 0.8204(6) 0.7301(6) 0.14372(19) 0.0275(10) Uani d . . . 1 . .
C C23 0.8163(6) 0.7300(6) 0.18877(19) 0.0300(11) Uani d . . . 1 . .
I I24 0.79544(4) 0.73983(4) 0.26447(2) 0.02991(8) Uani d . . . 1 . .
O O25 0.2562(4) 0.7860(5) 0.10773(14) 0.0345(9) Uani d . . . 1 . .
H H25 0.1738 0.7613 0.0925 0.052 Uiso calc U . R 1 . .
C C26 0.3788(6) 0.7726(5) 0.02314(18) 0.0237(9) Uani d . . . 1 . .
C C27 0.3699(7) 0.7680(5) -0.02260(19) 0.0275(10) Uani d . . . 1 . .
I I28 0.36977(4) 0.76173(3) -0.09897(2) 0.02528(7) Uani d . . . 1 . .
C C29 0.3731(6) 0.7493(5) 0.63241(18) 0.0236(9) Uani d . . . 1 . .
C C30 0.3655(6) 0.8685(5) 0.59716(19) 0.0274(10) Uani d . . . 1 . .
H H30 0.3545 0.9531 0.6088 0.033 Uiso calc U . R 1 . .
C C31 0.3741(7) 0.8621(6) 0.54474(19) 0.0294(10) Uani d . . . 1 . .
H H31 0.3674 0.9438 0.5216 0.035 Uiso calc U . R 1 . .
N N32 0.3916(6) 0.7451(5) 0.52541(16) 0.0300(9) Uani d . . . 1 . .
C C33 0.3971(7) 0.6310(6) 0.5590(2) 0.0341(12) Uani d . . . 1 . .
H H33 0.4082 0.5482 0.546 0.041 Uiso calc U . R 1 . .
C C34 0.3874(7) 0.6271(6) 0.61193(19) 0.0298(11) Uani d . . . 1 . .
H H34 0.3904 0.5435 0.6339 0.036 Uiso calc U . R 1 . .
C C35 0.3696(6) 0.7498(5) 0.68848(18) 0.0248(9) Uani d . . . 1 . .
C C36 0.2980(8) 0.8609(6) 0.7096(2) 0.0353(12) Uani d . . . 1 . .
H H36 0.2506 0.9384 0.6882 0.042 Uiso calc U . R 1 . .
C C37 0.2979(9) 0.8554(7) 0.7630(2) 0.0411(14) Uani d . . . 1 . .
H H37 0.2476 0.9306 0.7767 0.049 Uiso calc U . R 1 . .
N N38 0.3644(8) 0.7503(5) 0.79578(17) 0.0423(13) Uani d . . . 1 . .
C C39 0.4326(9) 0.6455(6) 0.7755(2) 0.0400(14) Uani d . . . 1 . .
H H39 0.4811 0.5708 0.7981 0.048 Uiso calc U . R 1 . .
C C40 0.4379(8) 0.6380(6) 0.7229(2) 0.0344(12) Uani d . . . 1 . .
H H40 0.486 0.5597 0.7107 0.041 Uiso calc U . R 1 . .
C C41 0.8790(6) 0.7419(5) 0.85278(18) 0.0255(10) Uani d . . . 1 . .
C C42 0.8875(7) 0.6192(6) 0.88514(19) 0.0302(11) Uani d . . . 1 . .
H H42 0.8852 0.5375 0.8717 0.036 Uiso calc U . R 1 . .
C C43 0.8994(7) 0.6183(6) 0.9378(2) 0.0356(12) Uani d . . . 1 . .
H H43 0.9045 0.5344 0.9597 0.043 Uiso calc U . R 1 . .
N N44 0.9039(6) 0.7321(6) 0.95906(17) 0.0374(11) Uani d . . . 1 . .
C C45 0.8941(7) 0.8516(6) 0.9270(2) 0.0356(12) Uani d . . . 1 . .
H H45 0.8953 0.9321 0.9414 0.043 Uiso calc U . R 1 . .
C C46 0.8826(7) 0.8607(6) 0.8741(2) 0.0341(12) Uani d . . . 1 . .
H H46 0.8772 0.9456 0.8529 0.041 Uiso calc U . R 1 . .
C C47 0.8674(7) 0.7474(5) 0.79519(18) 0.0280(10) Uani d . . . 1 . .
C C48 0.9419(8) 0.6428(6) 0.7709(2) 0.0360(12) Uani d . . . 1 . .
H H48 0.9976 0.5651 0.7902 0.043 Uiso calc U . R 1 . .
C C49 0.9319(9) 0.6562(7) 0.7179(2) 0.0431(14) Uani d . . . 1 . .
H H49 0.9836 0.5859 0.7016 0.052 Uiso calc U . R 1 . .
N N50 0.8534(7) 0.7627(6) 0.68845(18) 0.0439(13) Uani d . . . 1 . .
C C51 0.7793(9) 0.8611(7) 0.7121(2) 0.0428(14) Uani d . . . 1 . .
H H51 0.7215 0.9364 0.692 0.051 Uiso calc U . R 1 . .
C C52 0.7838(8) 0.8571(6) 0.7647(2) 0.0352(12) Uani d . . . 1 . .
H H52 0.7302 0.9288 0.7799 0.042 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O7 . 1.445(6) ?
C1 C8 . 1.476(7) ?
C1 C6 . 1.536(7) ?
C1 C2 . 1.538(7) ?
C2 C3 . 1.517(6) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C3 C4 . 1.537(6) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C4 O11 . 1.434(5) ?
C4 C12 . 1.471(6) ?
C4 C5 . 1.532(6) ?
C5 C6 . 1.529(6) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
O7 H7 . 0.85(4) ?
C8 C9 . 1.187(7) ?
C9 I10 . 2.021(5) ?
I10 N50 1_455 2.826(5) ?
O11 H11 . 0.86(4) ?
C12 C13 . 1.198(7) ?
C13 I14 . 2.011(5) ?
I14 O25 . 2.938(4) ?
C15 O21 . 1.435(5) ?
C15 C22 . 1.493(6) ?
C15 C20 . 1.530(7) ?
C15 C16 . 1.540(7) ?
C16 C17 . 1.525(6) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C17 C18 . 1.526(6) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C18 O25 . 1.444(5) ?
C18 C26 . 1.468(6) ?
C18 C19 . 1.536(7) ?
C19 C20 . 1.521(7) ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
O21 H21 . 0.89(4) ?
C22 C23 . 1.182(7) ?
C23 I24 . 2.007(5) ?
I24 O7 1_655 2.951(4) ?
O25 H25 . 0.83 ?
C26 C27 . 1.211(6) ?
C27 I28 . 2.014(5) ?
I28 N38 1_554 2.782(4) ?
C29 C30 . 1.391(7) ?
C29 C34 . 1.405(7) ?
C29 C35 . 1.472(6) ?
C30 C31 . 1.387(7) ?
C30 H30 . 0.94 ?
C31 N32 . 1.342(7) ?
C31 H31 . 0.94 ?
N32 C33 . 1.329(7) ?
C33 C34 . 1.386(7) ?
C33 H33 . 0.94 ?
C34 H34 . 0.94 ?
C35 C36 . 1.394(7) ?
C35 C40 . 1.402(7) ?
C36 C37 . 1.394(7) ?
C36 H36 . 0.94 ?
C37 N38 . 1.329(8) ?
C37 H37 . 0.94 ?
N38 C39 . 1.321(8) ?
C39 C40 . 1.394(7) ?
C39 H39 . 0.94 ?
C40 H40 . 0.94 ?
C41 C42 . 1.379(7) ?
C41 C46 . 1.391(7) ?
C41 C47 . 1.507(6) ?
C42 C43 . 1.384(7) ?
C42 H42 . 0.94 ?
C43 N44 . 1.344(8) ?
C43 H43 . 0.94 ?
N44 C45 . 1.350(8) ?
C45 C46 . 1.380(7) ?
C45 H45 . 0.94 ?
C46 H46 . 0.94 ?
C47 C52 . 1.381(7) ?
C47 C48 . 1.393(7) ?
C48 C49 . 1.381(8) ?
C48 H48 . 0.94 ?
C49 N50 . 1.331(8) ?
C49 H49 . 0.94 ?
N50 C51 . 1.334(8) ?
C51 C52 . 1.376(8) ?
C51 H51 . 0.94 ?
C52 H52 . 0.94 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O7 C1 C8 . . 111.7(4) ?
O7 C1 C6 . . 110.6(4) ?
C8 C1 C6 . . 109.3(4) ?
O7 C1 C2 . . 105.4(4) ?
C8 C1 C2 . . 109.7(4) ?
C6 C1 C2 . . 110.0(4) ?
C3 C2 C1 . . 111.9(4) ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C2 C3 C4 . . 111.9(4) ?
C2 C3 H3A . . 109.2 ?
C4 C3 H3A . . 109.2 ?
C2 C3 H3B . . 109.2 ?
C4 C3 H3B . . 109.2 ?
H3A C3 H3B . . 107.9 ?
O11 C4 C12 . . 108.9(4) ?
O11 C4 C5 . . 109.8(4) ?
C12 C4 C5 . . 109.9(4) ?
O11 C4 C3 . . 110.2(4) ?
C12 C4 C3 . . 108.8(4) ?
C5 C4 C3 . . 109.3(4) ?
C6 C5 C4 . . 111.5(4) ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5B . . 109.3 ?
C4 C5 H5B . . 109.3 ?
H5A C5 H5B . . 108.0 ?
C5 C6 C1 . . 112.3(4) ?
C5 C6 H6A . . 109.1 ?
C1 C6 H6A . . 109.1 ?
C5 C6 H6B . . 109.1 ?
C1 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.9 ?
C1 O7 H7 . . 125.(6) ?
C9 C8 C1 . . 172.2(5) ?
C8 C9 I10 . . 177.6(5) ?
C9 I10 N50 . 1_455 178.30(19) ?
C4 O11 H11 . . 114.(5) ?
C13 C12 C4 . . 169.5(5) ?
C12 C13 I14 . . 176.0(5) ?
C13 I14 O25 . . 175.19(19) ?
O21 C15 C22 . . 108.1(4) ?
O21 C15 C20 . . 110.1(4) ?
C22 C15 C20 . . 109.4(4) ?
O21 C15 C16 . . 110.7(4) ?
C22 C15 C16 . . 109.4(4) ?
C20 C15 C16 . . 109.1(4) ?
C17 C16 C15 . . 112.3(4) ?
C17 C16 H16A . . 109.2 ?
C15 C16 H16A . . 109.2 ?
C17 C16 H16B . . 109.2 ?
C15 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C16 C17 C18 . . 112.3(4) ?
C16 C17 H17A . . 109.2 ?
C18 C17 H17A . . 109.2 ?
C16 C17 H17B . . 109.2 ?
C18 C17 H17B . . 109.2 ?
H17A C17 H17B . . 107.9 ?
O25 C18 C26 . . 112.7(4) ?
O25 C18 C17 . . 105.8(4) ?
C26 C18 C17 . . 109.6(4) ?
O25 C18 C19 . . 109.2(4) ?
C26 C18 C19 . . 109.0(4) ?
C17 C18 C19 . . 110.6(4) ?
C20 C19 C18 . . 112.5(4) ?
C20 C19 H19A . . 109.1 ?
C18 C19 H19A . . 109.1 ?
C20 C19 H19B . . 109.1 ?
C18 C19 H19B . . 109.1 ?
H19A C19 H19B . . 107.8 ?
C19 C20 C15 . . 111.9(4) ?
C19 C20 H20A . . 109.2 ?
C15 C20 H20A . . 109.2 ?
C19 C20 H20B . . 109.2 ?
C15 C20 H20B . . 109.2 ?
H20A C20 H20B . . 107.9 ?
C15 O21 H21 . . 111.(5) ?
C23 C22 C15 . . 171.5(5) ?
C22 C23 I24 . . 176.0(5) ?
C23 I24 O7 . 1_655 173.60(19) ?
C18 O25 I14 . . 115.8(3) ?
C18 O25 H25 . . 109.5 ?
I14 O25 H25 . . 123.3 ?
C27 C26 C18 . . 172.4(5) ?
C26 C27 I28 . . 176.7(5) ?
C27 I28 N38 . 1_554 178.97(19) ?
C30 C29 C34 . . 116.7(4) ?
C30 C29 C35 . . 122.1(4) ?
C34 C29 C35 . . 121.1(5) ?
C31 C30 C29 . . 119.7(5) ?
C31 C30 H30 . . 120.2 ?
C29 C30 H30 . . 120.2 ?
N32 C31 C30 . . 123.3(5) ?
N32 C31 H31 . . 118.3 ?
C30 C31 H31 . . 118.3 ?
C33 N32 C31 . . 117.1(4) ?
N32 C33 C34 . . 123.8(5) ?
N32 C33 H33 . . 118.1 ?
C34 C33 H33 . . 118.1 ?
C33 C34 C29 . . 119.3(5) ?
C33 C34 H34 . . 120.3 ?
C29 C34 H34 . . 120.3 ?
C36 C35 C40 . . 117.2(5) ?
C36 C35 C29 . . 121.5(4) ?
C40 C35 C29 . . 121.2(5) ?
C35 C36 C37 . . 119.0(5) ?
C35 C36 H36 . . 120.5 ?
C37 C36 H36 . . 120.5 ?
N38 C37 C36 . . 124.1(5) ?
N38 C37 H37 . . 118.0 ?
C36 C37 H37 . . 118.0 ?
C39 N38 C37 . . 116.7(5) ?
N38 C39 C40 . . 124.7(5) ?
N38 C39 H39 . . 117.7 ?
C40 C39 H39 . . 117.7 ?
C39 C40 C35 . . 118.4(5) ?
C39 C40 H40 . . 120.8 ?
C35 C40 H40 . . 120.8 ?
C42 C41 C46 . . 118.9(5) ?
C42 C41 C47 . . 120.7(5) ?
C46 C41 C47 . . 120.4(5) ?
C41 C42 C43 . . 118.9(5) ?
C41 C42 H42 . . 120.5 ?
C43 C42 H42 . . 120.5 ?
N44 C43 C42 . . 122.9(5) ?
N44 C43 H43 . . 118.5 ?
C42 C43 H43 . . 118.5 ?
C43 N44 C45 . . 117.6(5) ?
N44 C45 C46 . . 122.9(5) ?
N44 C45 H45 . . 118.6 ?
C46 C45 H45 . . 118.6 ?
C45 C46 C41 . . 118.8(5) ?
C45 C46 H46 . . 120.6 ?
C41 C46 H46 . . 120.6 ?
C52 C47 C48 . . 117.9(5) ?
C52 C47 C41 . . 120.9(5) ?
C48 C47 C41 . . 121.2(5) ?
C49 C48 C47 . . 118.3(5) ?
C49 C48 H48 . . 120.9 ?
C47 C48 H48 . . 120.9 ?
N50 C49 C48 . . 123.8(6) ?
N50 C49 H49 . . 118.1 ?
C48 C49 H49 . . 118.1 ?
C49 N50 C51 . . 117.5(5) ?
N50 C51 C52 . . 122.8(6) ?
N50 C51 H51 . . 118.6 ?
C52 C51 H51 . . 118.6 ?
C51 C52 C47 . . 119.7(6) ?
C51 C52 H52 . . 120.2 ?
C47 C52 H52 . . 120.2 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O7 C1 C2 C3 . . . . -173.2(4) ?
C8 C1 C2 C3 . . . . 66.4(5) ?
C6 C1 C2 C3 . . . . -53.9(5) ?
C1 C2 C3 C4 . . . . 56.9(5) ?
C2 C3 C4 O11 . . . . -177.7(4) ?
C2 C3 C4 C12 . . . . 63.0(5) ?
C2 C3 C4 C5 . . . . -57.0(5) ?
O11 C4 C5 C6 . . . . 177.2(4) ?
C12 C4 C5 C6 . . . . -63.1(5) ?
C3 C4 C5 C6 . . . . 56.2(5) ?
C4 C5 C6 C1 . . . . -56.0(5) ?
O7 C1 C6 C5 . . . . 169.6(4) ?
C8 C1 C6 C5 . . . . -67.0(5) ?
C2 C1 C6 C5 . . . . 53.6(5) ?
O11 C4 C12 C13 . . . . -163.(3) ?
C5 C4 C12 C13 . . . . 76.(3) ?
C3 C4 C12 C13 . . . . -43.(3) ?
O21 C15 C16 C17 . . . . 177.2(4) ?
C22 C15 C16 C17 . . . . -63.8(5) ?
C20 C15 C16 C17 . . . . 55.9(5) ?
C15 C16 C17 C18 . . . . -55.4(5) ?
C16 C17 C18 O25 . . . . 170.7(4) ?
C16 C17 C18 C26 . . . . -67.6(5) ?
C16 C17 C18 C19 . . . . 52.6(5) ?
O25 C18 C19 C20 . . . . -169.0(4) ?
C26 C18 C19 C20 . . . . 67.6(5) ?
C17 C18 C19 C20 . . . . -53.0(5) ?
C18 C19 C20 C15 . . . . 55.9(5) ?
O21 C15 C20 C19 . . . . -177.7(4) ?
C22 C15 C20 C19 . . . . 63.7(5) ?
C16 C15 C20 C19 . . . . -56.0(5) ?
C26 C18 O25 I14 . . . . 170.2(3) ?
C17 C18 O25 I14 . . . . -70.1(4) ?
C19 C18 O25 I14 . . . . 48.9(4) ?
C34 C29 C30 C31 . . . . -0.7(7) ?
C35 C29 C30 C31 . . . . 178.2(5) ?
C29 C30 C31 N32 . . . . -0.7(8) ?
C30 C31 N32 C33 . . . . 1.4(8) ?
C31 N32 C33 C34 . . . . -0.6(8) ?
N32 C33 C34 C29 . . . . -0.8(8) ?
C30 C29 C34 C33 . . . . 1.5(7) ?
C35 C29 C34 C33 . . . . -177.5(5) ?
C30 C29 C35 C36 . . . . 23.6(8) ?
C34 C29 C35 C36 . . . . -157.5(5) ?
C30 C29 C35 C40 . . . . -156.6(5) ?
C34 C29 C35 C40 . . . . 22.2(8) ?
C40 C35 C36 C37 . . . . 0.0(9) ?
C29 C35 C36 C37 . . . . 179.8(5) ?
C35 C36 C37 N38 . . . . 0.9(10) ?
C36 C37 N38 C39 . . . . -0.7(10) ?
C37 N38 C39 C40 . . . . -0.5(10) ?
N38 C39 C40 C35 . . . . 1.4(10) ?
C36 C35 C40 C39 . . . . -1.0(8) ?
C29 C35 C40 C39 . . . . 179.2(5) ?
C46 C41 C42 C43 . . . . -0.1(8) ?
C47 C41 C42 C43 . . . . 179.5(5) ?
C41 C42 C43 N44 . . . . -0.3(8) ?
C42 C43 N44 C45 . . . . 0.8(8) ?
C43 N44 C45 C46 . . . . -1.0(8) ?
N44 C45 C46 C41 . . . . 0.6(9) ?
C42 C41 C46 C45 . . . . -0.1(8) ?
C47 C41 C46 C45 . . . . -179.7(5) ?
C42 C41 C47 C52 . . . . 150.3(5) ?
C46 C41 C47 C52 . . . . -30.1(8) ?
C42 C41 C47 C48 . . . . -30.3(8) ?
C46 C41 C47 C48 . . . . 149.3(6) ?
C52 C47 C48 C49 . . . . 1.6(9) ?
C41 C47 C48 C49 . . . . -177.8(5) ?
C47 C48 C49 N50 . . . . -0.8(10) ?
C48 C49 N50 C51 . . . . -0.6(10) ?
C49 N50 C51 C52 . . . . 1.1(10) ?
N50 C51 C52 C47 . . . . -0.2(10) ?
C48 C47 C52 C51 . . . . -1.2(9) ?
C41 C47 C52 C51 . . . . 178.2(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O7 H7 O11 1_455 0.85(4) 1.95(5) 2.758(5) 159.(9) ?
O11 H11 N32 . 0.86(4) 1.98(4) 2.809(5) 161.(7) ?
O21 H21 N44 1_554 0.89(4) 1.92(4) 2.786(6) 163.(7) ?
O25 H25 O21 1_455 0.83 1.89 2.717(5) 171.5 ?

####################################################################### 
# 
# 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_D1A4
_database_code_depnum_ccdc_archive 'CCDC 1820024'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H10 I2 O2, C12 H10 N2'
_chemical_formula_sum            'C22 H20 I2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         598.20

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8373(7)
_cell_length_b                   11.6273(11)
_cell_length_c                   12.6853(12)
_cell_angle_alpha                93.5792(12)
_cell_angle_beta                 96.5739(11)
_cell_angle_gamma                107.2327(11)
_cell_volume                     1091.15(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7080
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      33.11
_cell_measurement_temperature    228.(2)

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576

_exptl_absorpt_coefficient_mu    2.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_T_max  0.69

_exptl_special_details           
;
;

_diffrn_ambient_temperature      228.(2)

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            15152
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         33.33
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             7687
_reflns_number_gt                6045
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0659
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         7687
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+0.6710P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.070
_refine_diff_density_min         -1.031
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker SMART'
_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'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7732(3) 0.1228(2) 0.70196(17) 0.0211(4) Uani d . . . 1 . .
C C2 0.9225(3) 0.2441(2) 0.72503(18) 0.0226(4) Uani d . . . 1 . .
H H2A 0.9379 0.2826 0.6588 0.027 Uiso calc U . R 1 . .
H H2B 0.8872 0.2975 0.7752 0.027 Uiso calc U . R 1 . .
C C3 1.1013(3) 0.2280(2) 0.77209(17) 0.0231(4) Uani d . . . 1 . .
H H3A 1.0884 0.1962 0.8415 0.028 Uiso calc U . R 1 . .
H H3B 1.1943 0.3071 0.7837 0.028 Uiso calc U . R 1 . .
C C4 1.1618(3) 0.1418(2) 0.69925(17) 0.0209(4) Uani d . . . 1 . .
C C5 1.0121(3) 0.0211(2) 0.67204(18) 0.0233(4) Uani d . . . 1 . .
H H5A 1.0478 -0.0295 0.6194 0.028 Uiso calc U . R 1 . .
H H5B 0.9973 -0.0211 0.7365 0.028 Uiso calc U . R 1 . .
C C6 0.8323(3) 0.0369(2) 0.62753(17) 0.0226(4) Uani d . . . 1 . .
H H6A 0.7395 -0.0423 0.6164 0.027 Uiso calc U . R 1 . .
H H6B 0.8426 0.0688 0.5581 0.027 Uiso calc U . R 1 . .
H H7 0.624(4) 0.171(3) 0.597(3) 0.043(9) Uiso d . . . 1 . .
O O7 0.6085(2) 0.13918(17) 0.65397(14) 0.0283(4) Uani d . . . 1 . .
C C8 0.7387(3) 0.0699(2) 0.80391(18) 0.0244(4) Uani d . . . 1 . .
C C9 0.7353(3) 0.0320(3) 0.8892(2) 0.0312(5) Uani d . . . 1 . .
I I10 0.72878(2) -0.02968(2) 1.03349(2) 0.03274(5) Uani d . . . 1 . .
H H11 1.396(4) 0.124(3) 0.719(2) 0.036(8) Uiso d . . . 1 . .
O O11 1.3160(2) 0.12158(18) 0.75851(14) 0.0307(4) Uani d . . . 1 . .
C C12 1.2075(3) 0.1997(2) 0.60132(18) 0.0239(4) Uani d . . . 1 . .
C C13 1.2292(3) 0.2489(2) 0.52160(19) 0.0269(5) Uani d . . . 1 . .
I I14 1.25438(2) 0.32950(2) 0.38484(2) 0.02702(5) Uani d . . . 1 . .
C C15 0.2396(4) 0.5840(3) 0.8204(2) 0.0358(6) Uani d . . . 1 . .
H H15 0.165 0.5032 0.8112 0.043 Uiso calc U . R 1 . .
C C16 0.3140(4) 0.6291(3) 0.9182(2) 0.0371(6) Uani d . . . 1 . .
H H16 0.3847 0.7109 0.9278 0.044 Uiso calc U . R 1 . .
C C17 0.2620(4) 0.6480(2) 0.7240(2) 0.0294(5) Uani d . . . 1 . .
C C18 0.3288(4) 0.7740(2) 0.7259(2) 0.0313(5) Uani d . . . 1 . .
H H18 0.3584 0.8234 0.791 0.038 Uiso calc U . R 1 . .
C C19 0.3506(3) 0.8250(2) 0.6308(2) 0.0308(5) Uani d . . . 1 . .
H H19 0.3956 0.9097 0.6332 0.037 Uiso calc U . R 1 . .
N N20 0.3110(3) 0.7600(2) 0.53529(16) 0.0290(4) Uani d . . . 1 . .
C C21 0.2473(4) 0.6399(2) 0.5341(2) 0.0337(6) Uani d . . . 1 . .
H H21 0.22 0.5927 0.4679 0.04 Uiso calc U . R 1 . .
C C22 0.2196(4) 0.5815(2) 0.6245(2) 0.0327(5) Uani d . . . 1 . .
H H22 0.1721 0.4967 0.619 0.039 Uiso calc U . R 1 . .
C C23 0.2970(4) 0.5635(2) 1.0144(2) 0.0319(5) Uani d . . . 1 . .
C C24 0.3931(4) 0.6215(3) 1.1113(2) 0.0384(6) Uani d . . . 1 . .
H H24 0.4663 0.7024 1.1161 0.046 Uiso calc U . R 1 . .
C C25 0.3804(4) 0.5595(3) 1.2005(2) 0.0415(7) Uani d . . . 1 . .
H H25 0.4462 0.6008 1.2656 0.05 Uiso calc U . R 1 . .
N N26 0.2811(4) 0.4452(2) 1.20042(18) 0.0408(6) Uani d . . . 1 . .
C C27 0.1861(5) 0.3889(3) 1.1074(2) 0.0448(7) Uani d . . . 1 . .
H H27 0.1137 0.3081 1.1055 0.054 Uiso calc U . R 1 . .
C C28 0.1892(4) 0.4440(3) 1.0137(2) 0.0421(7) Uani d . . . 1 . .
H H28 0.1193 0.4013 0.9502 0.05 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O7 . 1.433(3) ?
C1 C8 . 1.485(3) ?
C1 C2 . 1.528(3) ?
C1 C6 . 1.536(3) ?
C2 C3 . 1.527(3) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C3 C4 . 1.533(3) ?
C3 H3A . 0.98 ?
C3 H3B . 0.98 ?
C4 O11 . 1.437(3) ?
C4 C12 . 1.479(3) ?
C4 C5 . 1.529(3) ?
C5 C6 . 1.524(3) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
O7 H7 . 0.84(3) ?
C8 C9 . 1.194(3) ?
C9 I10 . 2.007(2) ?
I10 O11 2_757 2.9273(17) ?
O11 H11 . 0.84(3) ?
C12 C13 . 1.197(3) ?
C13 I14 . 2.024(2) ?
I14 N26 1_654 2.768(2) ?
C15 C16 . 1.313(4) ?
C15 C17 . 1.472(3) ?
C15 H15 . 0.94 ?
C16 C23 . 1.478(3) ?
C16 H16 . 0.94 ?
C17 C22 . 1.390(4) ?
C17 C18 . 1.400(4) ?
C18 C19 . 1.383(3) ?
C18 H18 . 0.94 ?
C19 N20 . 1.340(3) ?
C19 H19 . 0.94 ?
N20 C21 . 1.334(3) ?
C21 C22 . 1.375(3) ?
C21 H21 . 0.94 ?
C22 H22 . 0.94 ?
C23 C24 . 1.384(4) ?
C23 C28 . 1.395(4) ?
C24 C25 . 1.377(4) ?
C24 H24 . 0.94 ?
C25 N26 . 1.327(4) ?
C25 H25 . 0.94 ?
N26 C27 . 1.338(4) ?
C27 C28 . 1.384(4) ?
C27 H27 . 0.94 ?
C28 H28 . 0.94 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O7 C1 C8 . . 107.57(17) ?
O7 C1 C2 . . 110.63(18) ?
C8 C1 C2 . . 109.18(19) ?
O7 C1 C6 . . 110.08(18) ?
C8 C1 C6 . . 110.01(18) ?
C2 C1 C6 . . 109.35(17) ?
C3 C2 C1 . . 111.47(18) ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2B . . 109.3 ?
C1 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108.0 ?
C2 C3 C4 . . 112.21(18) ?
C2 C3 H3A . . 109.2 ?
C4 C3 H3A . . 109.2 ?
C2 C3 H3B . . 109.2 ?
C4 C3 H3B . . 109.2 ?
H3A C3 H3B . . 107.9 ?
O11 C4 C12 . . 111.64(18) ?
O11 C4 C5 . . 109.03(18) ?
C12 C4 C5 . . 110.73(19) ?
O11 C4 C3 . . 106.55(18) ?
C12 C4 C3 . . 108.56(18) ?
C5 C4 C3 . . 110.24(18) ?
C6 C5 C4 . . 112.47(18) ?
C6 C5 H5A . . 109.1 ?
C4 C5 H5A . . 109.1 ?
C6 C5 H5B . . 109.1 ?
C4 C5 H5B . . 109.1 ?
H5A C5 H5B . . 107.8 ?
C5 C6 C1 . . 112.40(18) ?
C5 C6 H6A . . 109.1 ?
C1 C6 H6A . . 109.1 ?
C5 C6 H6B . . 109.1 ?
C1 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.9 ?
C1 O7 H7 . . 110.(2) ?
C9 C8 C1 . . 171.3(2) ?
C8 C9 I10 . . 179.2(2) ?
C9 I10 O11 . 2_757 174.73(8) ?
C4 O11 H11 . . 110.(2) ?
C13 C12 C4 . . 173.8(2) ?
C12 C13 I14 . . 177.5(2) ?
C13 I14 N26 . 1_654 177.81(9) ?
C16 C15 C17 . . 126.2(3) ?
C16 C15 H15 . . 116.9 ?
C17 C15 H15 . . 116.9 ?
C15 C16 C23 . . 126.2(3) ?
C15 C16 H16 . . 116.9 ?
C23 C16 H16 . . 116.9 ?
C22 C17 C18 . . 116.9(2) ?
C22 C17 C15 . . 119.3(2) ?
C18 C17 C15 . . 123.7(2) ?
C19 C18 C17 . . 119.2(2) ?
C19 C18 H18 . . 120.4 ?
C17 C18 H18 . . 120.4 ?
N20 C19 C18 . . 123.5(2) ?
N20 C19 H19 . . 118.3 ?
C18 C19 H19 . . 118.3 ?
C21 N20 C19 . . 117.0(2) ?
N20 C21 C22 . . 123.5(2) ?
N20 C21 H21 . . 118.2 ?
C22 C21 H21 . . 118.2 ?
C21 C22 C17 . . 119.9(2) ?
C21 C22 H22 . . 120.1 ?
C17 C22 H22 . . 120.1 ?
C24 C23 C28 . . 117.1(2) ?
C24 C23 C16 . . 119.4(2) ?
C28 C23 C16 . . 123.5(2) ?
C25 C24 C23 . . 119.4(3) ?
C25 C24 H24 . . 120.3 ?
C23 C24 H24 . . 120.3 ?
N26 C25 C24 . . 124.1(3) ?
N26 C25 H25 . . 118.0 ?
C24 C25 H25 . . 118.0 ?
C25 N26 C27 . . 116.9(2) ?
N26 C27 C28 . . 123.2(3) ?
N26 C27 H27 . . 118.4 ?
C28 C27 H27 . . 118.4 ?
C27 C28 C23 . . 119.4(3) ?
C27 C28 H28 . . 120.3 ?
C23 C28 H28 . . 120.3 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O7 C1 C2 C3 . . . . -177.70(17) ?
C8 C1 C2 C3 . . . . 64.1(2) ?
C6 C1 C2 C3 . . . . -56.3(2) ?
C1 C2 C3 C4 . . . . 57.1(2) ?
C2 C3 C4 O11 . . . . -172.21(18) ?
C2 C3 C4 C12 . . . . 67.4(2) ?
C2 C3 C4 C5 . . . . -54.0(2) ?
O11 C4 C5 C6 . . . . 169.34(17) ?
C12 C4 C5 C6 . . . . -67.4(2) ?
C3 C4 C5 C6 . . . . 52.7(2) ?
C4 C5 C6 C1 . . . . -54.7(2) ?
O7 C1 C6 C5 . . . . 177.09(18) ?
C8 C1 C6 C5 . . . . -64.5(2) ?
C2 C1 C6 C5 . . . . 55.4(2) ?
C17 C15 C16 C23 . . . . -177.5(3) ?
C16 C15 C17 C22 . . . . 161.6(3) ?
C16 C15 C17 C18 . . . . -16.7(5) ?
C22 C17 C18 C19 . . . . -0.7(4) ?
C15 C17 C18 C19 . . . . 177.7(3) ?
C17 C18 C19 N20 . . . . 0.0(4) ?
C18 C19 N20 C21 . . . . 0.0(4) ?
C19 N20 C21 C22 . . . . 0.6(4) ?
N20 C21 C22 C17 . . . . -1.3(4) ?
C18 C17 C22 C21 . . . . 1.3(4) ?
C15 C17 C22 C21 . . . . -177.2(3) ?
C15 C16 C23 C24 . . . . 175.9(3) ?
C15 C16 C23 C28 . . . . -3.6(5) ?
C28 C23 C24 C25 . . . . 0.9(4) ?
C16 C23 C24 C25 . . . . -178.6(3) ?
C23 C24 C25 N26 . . . . 0.4(5) ?
C24 C25 N26 C27 . . . . -1.2(5) ?
C25 N26 C27 C28 . . . . 0.7(5) ?
N26 C27 C28 C23 . . . . 0.6(5) ?
C24 C23 C28 C27 . . . . -1.4(4) ?
C16 C23 C28 C27 . . . . 178.1(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O7 H7 N20 2_666 0.84(3) 1.95(3) 2.792(3) 172.(3) ?
O11 H11 O7 1_655 0.84(3) 1.91(3) 2.740(2) 169.(3) ?

####################################################################### 
# 
# 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_D3A3
_database_code_depnum_ccdc_archive 'CCDC 1820027'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;

#_audit_creation_method            SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 O2, C10 H8 N2'
_chemical_formula_sum            'C20 H20 N2 O2'
_chemical_formula_weight         320.38

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

_space_group_crystal_system      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                   5.9239(5)
_cell_length_b                   12.3895(9)
_cell_length_c                   13.2181(8)
_cell_angle_alpha                110.998(6)
_cell_angle_beta                 96.684(6)
_cell_angle_gamma                99.359(6)
_cell_volume                     877.44(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1891
_cell_measurement_theta_min      4.9190
_cell_measurement_theta_max      31.4620

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.81675
_exptl_absorpt_correction_T_max  1.00000

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurment_method        '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7304
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.389
_diffrn_reflns_theta_max         26.991
_reflns_number_total             3841
_reflns_number_gt                2595
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies, Version 1.171.37.35 
;
_computing_structure_solution    
;
SHELXS-2014/7 (Sheldrick, 2014)
;
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
;
_computing_molecular_graphics    
;
Mercury (Bruno et al., 2002)
;
_computing_publication_material  
;
SHELXL-2014/7 (Sheldrick, 2013) and PLATON (Spek, 2003)
;

_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)+(0.0404P)²+0.1163P] 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     SHELXL
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3823
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
O1 O 0.5947(2) 0.71766(10) 0.31447(9) 0.0491(3) Uani 1 1 d . . . . .
O2 O 0.8917(2) 0.86823(11) 0.77009(9) 0.0573(3) Uani 1 1 d . . . . .
N1 N 0.8058(3) 0.91418(13) 0.09040(12) 0.0585(4) Uani 1 1 d . . . . .
N2 N -0.2023(3) 0.46159(13) -0.20029(12) 0.0584(4) Uani 1 1 d . . . . .
C1 C 0.8193(4) 0.51967(19) 0.39638(17) 0.0669(6) Uani 1 1 d . . . . .
C2 C 0.7627(3) 0.60884(14) 0.40699(13) 0.0455(4) Uani 1 1 d . . . . .
C3 C 0.6847(2) 0.72004(12) 0.42050(12) 0.0380(3) Uani 1 1 d . . . . .
C4 C 0.8888(3) 0.82743(14) 0.47230(13) 0.0420(4) Uani 1 1 d . . . . .
H4A H 1.0114 0.8148 0.4295 0.050 Uiso 1 1 calc R U . . .
H4B H 0.8375 0.8970 0.4695 0.050 Uiso 1 1 calc R U . . .
C5 C 0.9862(2) 0.85002(14) 0.59164(13) 0.0425(4) Uani 1 1 d . . . . .
H5A H 1.1090 0.9214 0.6219 0.051 Uiso 1 1 calc R U . . .
H5B H 1.0545 0.7845 0.5935 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8003(3) 0.86394(13) 0.66376(12) 0.0410(4) Uani 1 1 d . . . . .
C7 C 0.5980(3) 0.75521(14) 0.61182(13) 0.0450(4) Uani 1 1 d . . . . .
H7A H 0.6519 0.6859 0.6136 0.054 Uiso 1 1 calc R U . . .
H7B H 0.4758 0.7664 0.6550 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4990(2) 0.73393(14) 0.49310(13) 0.0435(4) Uani 1 1 d . . . . .
H8A H 0.4316 0.8000 0.4922 0.052 Uiso 1 1 calc R U . . .
H8B H 0.3754 0.6629 0.4626 0.052 Uiso 1 1 calc R U . . .
C9 C 0.7147(3) 0.97300(14) 0.67453(13) 0.0464(4) Uani 1 1 d . . . . .
C10 C 0.6439(3) 1.05801(18) 0.68131(16) 0.0612(5) Uani 1 1 d . . . . .
C11 C 0.7283(3) 0.82912(16) 0.12561(15) 0.0598(5) Uani 1 1 d . . . . .
H11 H 0.8083 0.8314 0.1914 0.072 Uiso 1 1 calc R U . . .
C12 C 0.5371(3) 0.73852(15) 0.07015(13) 0.0517(4) Uani 1 1 d . . . . .
H12 H 0.4920 0.6808 0.0979 0.062 Uiso 1 1 calc R U . . .
C13 C 0.4115(3) 0.73341(13) -0.02746(12) 0.0423(4) Uani 1 1 d . . . . .
C14 C 0.4917(3) 0.82097(14) -0.06474(13) 0.0514(4) Uani 1 1 d . . . . .
H14 H 0.4141 0.8214 -0.1299 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6878(3) 0.90751(15) -0.00436(14) 0.0563(5) Uani 1 1 d . . . . .
H15 H 0.7406 0.9646 -0.0316 0.068 Uiso 1 1 calc R U . . .
C16 C 0.1999(3) 0.63895(14) -0.08851(12) 0.0428(4) Uani 1 1 d . . . . .
C17 C 0.1884(3) 0.52271(15) -0.10011(14) 0.0536(4) Uani 1 1 d . . . . .
H17 H 0.3154 0.5017 -0.0696 0.064 Uiso 1 1 calc R U . . .
C18 C -0.0112(3) 0.43838(16) -0.15685(15) 0.0608(5) Uani 1 1 d . . . . .
H18 H -0.0129 0.3604 -0.1654 0.073 Uiso 1 1 calc R U . . .
C19 C -0.1902(3) 0.57358(17) -0.18947(15) 0.0606(5) Uani 1 1 d . . . . .
H19 H -0.3206 0.5920 -0.2203 0.073 Uiso 1 1 calc R U . . .
C20 C 0.0031(3) 0.66372(15) -0.13557(14) 0.0542(4) Uani 1 1 d . . . . .
H20 H 0.0020 0.7404 -0.1307 0.065 Uiso 1 1 calc R U . . .
H1O H 0.470(4) 0.6557(18) 0.2829(17) 0.079(7) Uiso 1 1 d . . . . .
H2O H 0.990(4) 0.943(2) 0.8099(19) 0.096(7) Uiso 1 1 d . . . . .
H10 H 0.588(4) 1.1255(19) 0.6878(17) 0.087(7) Uiso 1 1 d . . . . .
H1 H 0.868(4) 0.451(2) 0.3873(19) 0.098(8) Uiso 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
O1 C3 1.4286(17) . ?
O1 H1O 0.91(2) . ?
O2 C6 1.4252(17) . ?
O2 H2O 0.94(2) . ?
N1 C15 1.330(2) . ?
N1 C11 1.335(2) . ?
N2 C18 1.329(2) . ?
N2 C19 1.332(2) . ?
C1 C2 1.172(2) . ?
C1 H1 0.91(2) . ?
C2 C3 1.481(2) . ?
C3 C4 1.5270(19) . ?
C3 C8 1.533(2) . ?
C4 C5 1.523(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.530(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C9 1.485(2) . ?
C6 C7 1.531(2) . ?
C7 C8 1.522(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.174(2) . ?
C10 H10 0.93(2) . ?
C11 C12 1.372(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(2) . ?
C13 C16 1.484(2) . ?
C14 C15 1.379(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.382(2) . ?
C16 C20 1.387(2) . ?
C17 C18 1.372(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.375(2) . ?
C19 H19 0.9300 . ?
C20 H20 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
C3 O1 H1O 107.7(13) . . ?
C6 O2 H2O 107.9(14) . . ?
C15 N1 C11 116.39(15) . . ?
C18 N2 C19 116.23(15) . . ?
C2 C1 H1 178.1(15) . . ?
C1 C2 C3 178.44(19) . . ?
O1 C3 C2 109.39(12) . . ?
O1 C3 C4 106.17(12) . . ?
C2 C3 C4 111.11(12) . . ?
O1 C3 C8 110.77(12) . . ?
C2 C3 C8 109.72(13) . . ?
C4 C3 C8 109.64(12) . . ?
C5 C4 C3 112.28(12) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 112.60(12) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
O2 C6 C9 110.08(12) . . ?
O2 C6 C5 110.45(12) . . ?
C9 C6 C5 110.29(13) . . ?
O2 C6 C7 106.67(12) . . ?
C9 C6 C7 110.00(12) . . ?
C5 C6 C7 109.28(12) . . ?
C8 C7 C6 111.87(13) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C3 112.28(12) . . ?
C7 C8 H8A 109.1 . . ?
C3 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C3 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C6 178.75(18) . . ?
C9 C10 H10 179.1(14) . . ?
N1 C11 C12 123.70(16) . . ?
N1 C11 H11 118.1 . . ?
C12 C11 H11 118.1 . . ?
C11 C12 C13 119.69(16) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 116.90(15) . . ?
C14 C13 C16 121.59(14) . . ?
C12 C13 C16 121.51(15) . . ?
C15 C14 C13 119.35(15) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N1 C15 C14 123.95(17) . . ?
N1 C15 H15 118.0 . . ?
C14 C15 H15 118.0 . . ?
C17 C16 C20 116.89(15) . . ?
C17 C16 C13 121.72(14) . . ?
C20 C16 C13 121.39(15) . . ?
C18 C17 C16 119.73(16) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
N2 C18 C17 123.86(17) . . ?
N2 C18 H18 118.1 . . ?
C17 C18 H18 118.1 . . ?
N2 C19 C20 124.05(16) . . ?
N2 C19 H19 118.0 . . ?
C20 C19 H19 118.0 . . ?
C19 C20 C16 119.21(16) . . ?
C19 C20 H20 120.4 . . ?
C16 C20 H20 120.4 . . ?

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 C3 C4 C5 173.49(12) . . . . ?
C2 C3 C4 C5 -67.67(16) . . . . ?
C8 C3 C4 C5 53.78(16) . . . . ?
C3 C4 C5 C6 -55.56(17) . . . . ?
C4 C5 C6 O2 171.88(12) . . . . ?
C4 C5 C6 C9 -66.22(16) . . . . ?
C4 C5 C6 C7 54.83(17) . . . . ?
O2 C6 C7 C8 -174.70(12) . . . . ?
C9 C6 C7 C8 65.94(16) . . . . ?
C5 C6 C7 C8 -55.28(17) . . . . ?
C6 C7 C8 C3 56.80(17) . . . . ?
O1 C3 C8 C7 -171.50(12) . . . . ?
C2 C3 C8 C7 67.63(16) . . . . ?
C4 C3 C8 C7 -54.65(17) . . . . ?
C15 N1 C11 C12 -0.4(3) . . . . ?
N1 C11 C12 C13 -1.0(3) . . . . ?
C11 C12 C13 C14 1.2(2) . . . . ?
C11 C12 C13 C16 -178.28(16) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C16 C13 C14 C15 179.31(14) . . . . ?
C11 N1 C15 C14 1.6(3) . . . . ?
C13 C14 C15 N1 -1.2(3) . . . . ?
C14 C13 C16 C17 139.85(17) . . . . ?
C12 C13 C16 C17 -40.6(2) . . . . ?
C14 C13 C16 C20 -40.9(2) . . . . ?
C12 C13 C16 C20 138.60(17) . . . . ?
C20 C16 C17 C18 0.5(2) . . . . ?
C13 C16 C17 C18 179.73(16) . . . . ?
C19 N2 C18 C17 2.2(3) . . . . ?
C16 C17 C18 N2 -1.9(3) . . . . ?
C18 N2 C19 C20 -1.1(3) . . . . ?
N2 C19 C20 C16 -0.2(3) . . . . ?
C17 C16 C20 C19 0.5(2) . . . . ?
C13 C16 C20 C19 -178.74(16) . . . . ?

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
C20 H20 O2 0.93 2.51 3.321(2) 146.4 1_454
O1 H1O N2 0.91(2) 1.88(2) 2.7777(18) 170.5(19) 2_565
O2 H2O N1 0.94(2) 1.89(2) 2.8241(19) 170(2) 2_776
C20 H20 O2 0.93 2.51 3.321(2) 146.4 1_454
O1 H1O N2 0.91(2) 1.88(2) 2.7777(18) 170.5(19) 2_565
O2 H2O N1 0.94(2) 1.89(2) 2.8241(19) 170(2) 2_776

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.037

_shelxl_version_number           2014-7

