# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_SA_C6I5COOH_a
_database_code_depnum_ccdc_archive 'CCDC 1919375'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H7 I5 O3'
_chemical_formula_weight         797.65

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   21.5195(7)
_cell_length_b                   8.8433(3)
_cell_length_c                   16.5517(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.697(3)
_cell_angle_gamma                90
_cell_volume                     3149.61(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5034
_cell_measurement_theta_min      3.8240
_cell_measurement_theta_max      28.7270

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.364
_exptl_crystal_F_000             2800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    9.869
_shelx_estimated_absorpt_T_min   0.319
_shelx_estimated_absorpt_T_max   0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            14326
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.372
_diffrn_reflns_theta_max         29.012
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7013
_reflns_number_gt                5704
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0154P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7013
_refine_ls_number_parameters     321
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0547
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4153(3) 0.8354(7) 0.4749(4) 0.0509(19) Uani 1 1 d . . . . .
H1A H 0.388961 0.789051 0.515909 0.076 Uiso 1 1 calc R U . . .
H1B H 0.398688 0.811723 0.420975 0.076 Uiso 1 1 calc R U . . .
H1C H 0.415929 0.945343 0.482479 0.076 Uiso 1 1 calc R U . . .
C2 C 0.3523(2) 0.3390(5) 0.4800(3) 0.0169(11) Uani 1 1 d . . . . .
C3 C 0.4797(3) 0.7750(8) 0.4829(4) 0.0459(17) Uani 1 1 d . . . . .
H3A H 0.480086 0.665925 0.469559 0.055 Uiso 1 1 calc R U . . .
H3B H 0.507434 0.828247 0.445077 0.055 Uiso 1 1 calc R U . . .
C4 C 0.2844(2) 0.3494(5) 0.5002(3) 0.0129(10) Uani 1 1 d . . . . .
C5 C 0.5316(4) 0.9354(11) 0.7660(6) 0.107(4) Uani 1 1 d . . . . .
H5A H 0.538576 0.840146 0.794889 0.161 Uiso 1 1 calc R U . . .
H5B H 0.544122 1.020303 0.800576 0.161 Uiso 1 1 calc R U . . .
H5C H 0.556180 0.936385 0.716551 0.161 Uiso 1 1 calc R U . . .
C6 C 0.4686(4) 0.9490(9) 0.7459(5) 0.078(3) Uani 1 1 d . . . . .
H6A H 0.445062 0.953199 0.796843 0.093 Uiso 1 1 calc R U . . .
H6B H 0.462629 1.047326 0.718288 0.093 Uiso 1 1 calc R U . . .
C7 C 0.2622(2) 0.2746(5) 0.5691(3) 0.0154(11) Uani 1 1 d . . . . .
C8 C 0.1988(2) 0.2772(5) 0.5865(3) 0.0153(10) Uani 1 1 d . . . . .
C9 C 0.1577(2) 0.3522(5) 0.5338(3) 0.0135(10) Uani 1 1 d . . . . .
C10 C 0.1800(2) 0.4276(5) 0.4656(2) 0.0130(10) Uani 1 1 d . . . . .
C11 C 0.2431(2) 0.4269(5) 0.4498(3) 0.0145(11) Uani 1 1 d . . . . .
C12 C 0.3078(3) 0.6625(5) 0.6809(3) 0.0173(7) Uani 1 1 d . U . . .
C13 C 0.2380(2) 0.6503(5) 0.6966(3) 0.0169(8) Uani 1 1 d . U . . .
C14 C 0.2155(2) 0.5724(5) 0.7644(3) 0.0147(10) Uani 1 1 d . . . . .
C15 C 0.1523(2) 0.5689(5) 0.7807(3) 0.0135(10) Uani 1 1 d . . . . .
C16 C 0.1107(2) 0.6462(5) 0.7301(3) 0.0147(10) Uani 1 1 d . . . . .
C17 C 0.1321(2) 0.7202(5) 0.6605(3) 0.0114(10) Uani 1 1 d . . . . .
C18 C 0.1952(2) 0.7206(5) 0.6443(3) 0.0143(11) Uani 1 1 d . . . . .
O1 O 0.4419(3) 0.8372(8) 0.6973(3) 0.084(2) Uani 1 1 d . . . . .
H1 H 0.459(4) 0.826(9) 0.651(5) 0.101 Uiso 1 1 d . U . . .
O2 O 0.5008(2) 0.7973(6) 0.5639(3) 0.0641(16) Uani 1 1 d . . . . .
H7 H 0.546(4) 0.787(8) 0.568(4) 0.077 Uiso 1 1 d . U . . .
O3 O 0.37180(17) 0.2464(4) 0.43371(19) 0.0223(8) Uani 1 1 d . . . . .
O4 O 0.38985(18) 0.4388(4) 0.5141(2) 0.0219(9) Uani 1 1 d . . . . .
H4 H 0.376(3) 0.483(6) 0.547(3) 0.026 Uiso 1 1 d . U . . .
O5 O 0.33308(17) 0.5771(4) 0.63565(18) 0.0216(7) Uani 1 1 d . U . . .
O6 O 0.33221(17) 0.7736(4) 0.7194(2) 0.0219(9) Uani 1 1 d . . . . .
H6 H 0.366(3) 0.795(6) 0.703(3) 0.026 Uiso 1 1 d . U . . .
I1 I 0.32798(2) 0.16350(4) 0.64205(2) 0.02065(8) Uani 1 1 d . . . . .
I2 I 0.16822(2) 0.17166(3) 0.69237(2) 0.01656(8) Uani 1 1 d . . . . .
I3 I 0.06206(2) 0.34797(4) 0.55662(2) 0.02042(8) Uani 1 1 d . . . . .
I4 I 0.11849(2) 0.53839(3) 0.38546(2) 0.01797(8) Uani 1 1 d . . . . .
I5 I 0.28129(2) 0.54709(3) 0.35310(2) 0.01652(8) Uani 1 1 d . . . . .
I6 I 0.28196(2) 0.46256(3) 0.83850(2) 0.01755(8) Uani 1 1 d . . . . .
I7 I 0.11990(2) 0.44393(4) 0.87918(2) 0.01867(8) Uani 1 1 d . . . . .
I8 I 0.01643(2) 0.65826(4) 0.76005(2) 0.02117(8) Uani 1 1 d . . . . .
I9 I 0.06960(2) 0.82926(4) 0.58256(2) 0.01946(8) Uani 1 1 d . . . . .
I10 I 0.23016(2) 0.82354(3) 0.53970(2) 0.01625(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.488(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O3 1.201(5) . ?
C2 O4 1.318(6) . ?
C2 C4 1.505(7) . ?
C3 O2 1.424(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C11 1.392(6) . ?
C4 C7 1.407(6) . ?
C5 C6 1.396(11) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 O1 1.395(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.398(7) . ?
C7 I1 2.095(5) . ?
C8 C9 1.401(6) . ?
C8 I2 2.099(4) . ?
C9 C10 1.400(6) . ?
C9 I3 2.098(5) . ?
C10 C11 1.387(7) . ?
C10 I4 2.104(4) . ?
C11 I5 2.097(4) . ?
C12 O5 1.198(5) . ?
C12 O6 1.280(6) . ?
C12 C13 1.531(7) . ?
C13 C18 1.402(6) . ?
C13 C14 1.408(6) . ?
C14 C15 1.390(7) . ?
C14 I6 2.109(5) . ?
C15 C16 1.398(6) . ?
C15 I7 2.096(4) . ?
C16 C17 1.407(6) . ?
C16 I8 2.097(5) . ?
C17 C18 1.387(6) . ?
C17 I9 2.089(4) . ?
C18 I10 2.103(4) . ?
O1 H1 0.86(8) . ?
O2 H7 0.99(8) . ?
O4 H4 0.73(5) . ?
O6 H6 0.79(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 O4 120.9(5) . . ?
O3 C2 C4 122.0(4) . . ?
O4 C2 C4 117.1(4) . . ?
O2 C3 C1 108.7(5) . . ?
O2 C3 H3A 109.9 . . ?
C1 C3 H3A 109.9 . . ?
O2 C3 H3B 109.9 . . ?
C1 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C11 C4 C7 119.7(5) . . ?
C11 C4 C2 120.8(4) . . ?
C7 C4 C2 119.5(4) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O1 C6 C5 118.0(8) . . ?
O1 C6 H6A 107.8 . . ?
C5 C6 H6A 107.8 . . ?
O1 C6 H6B 107.8 . . ?
C5 C6 H6B 107.8 . . ?
H6A C6 H6B 107.2 . . ?
C8 C7 C4 120.1(4) . . ?
C8 C7 I1 122.9(3) . . ?
C4 C7 I1 117.0(4) . . ?
C7 C8 C9 119.3(4) . . ?
C7 C8 I2 118.8(3) . . ?
C9 C8 I2 121.9(4) . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 I3 120.0(3) . . ?
C8 C9 I3 119.5(3) . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 I4 119.6(3) . . ?
C9 C10 I4 120.7(4) . . ?
C10 C11 C4 120.6(4) . . ?
C10 C11 I5 122.3(3) . . ?
C4 C11 I5 117.0(4) . . ?
O5 C12 O6 127.5(5) . . ?
O5 C12 C13 121.0(4) . . ?
O6 C12 C13 111.5(4) . . ?
C18 C13 C14 118.7(5) . . ?
C18 C13 C12 120.1(4) . . ?
C14 C13 C12 121.2(4) . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 I6 122.4(3) . . ?
C13 C14 I6 116.9(4) . . ?
C14 C15 C16 119.6(4) . . ?
C14 C15 I7 119.9(3) . . ?
C16 C15 I7 120.5(4) . . ?
C15 C16 C17 120.3(5) . . ?
C15 C16 I8 119.8(3) . . ?
C17 C16 I8 119.8(3) . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 I9 120.3(3) . . ?
C16 C17 I9 120.3(4) . . ?
C17 C18 C13 121.1(4) . . ?
C17 C18 I10 121.4(3) . . ?
C13 C18 I10 117.5(4) . . ?
C6 O1 H1 115(6) . . ?
C3 O2 H7 111(4) . . ?
C2 O4 H4 115(5) . . ?
C12 O6 H6 113(4) . . ?

_refine_diff_density_max         0.892
_refine_diff_density_min         -1.250
_refine_diff_density_rms         0.198

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
####################################################################### 
# 
# 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_K
_database_code_depnum_ccdc_archive 'CCDC 1919376'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;
#complex K[O2CC6I5]*2H2O
_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 I5 K O4'
_chemical_formula_weight         825.70

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

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

_cell_length_a                   37.861(3)
_cell_length_b                   9.2563(5)
_cell_length_c                   9.2740(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3250.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2597
_cell_measurement_theta_min      4.0840
_cell_measurement_theta_max      28.8110

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.375
_exptl_crystal_F_000             2896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    9.825
_shelx_estimated_absorpt_T_min   0.193
_shelx_estimated_absorpt_T_max   0.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            5040
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.504
_diffrn_reflns_theta_max         29.032
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1852
_reflns_number_gt                1683
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0467P)²+0.6426P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1852
_refine_ls_number_parameters     89
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5688(2) 0.500000 0.500000 0.0171(15) Uani 1 2 d S T P A .
C2 C 0.6088(2) 0.500000 0.500000 0.0151(15) Uani 1 2 d S T P . .
C3 C 0.62738(12) 0.5915(5) 0.5920(5) 0.0148(9) Uani 1 1 d . . . . .
C4 C 0.66406(12) 0.5928(5) 0.5925(5) 0.0136(9) Uani 1 1 d . . . . .
C5 C 0.68302(19) 0.500000 0.500000 0.0123(13) Uani 1 2 d S T P . .
O1 O 0.55020(18) 1.000000 0.500000 0.0410(16) Uani 1 2 d S T P . .
O2 O 0.55354(9) 0.5849(4) 0.4149(4) 0.0221(8) Uani 1 1 d . . . . .
I1 I 0.59775(2) 0.72791(4) 0.72816(4) 0.01987(14) Uani 1 1 d . . . . .
I2 I 0.69151(2) 0.73103(4) 0.73229(4) 0.02593(14) Uani 1 1 d . . . . .
I3 I 0.73792(2) 0.500000 0.500000 0.02399(16) Uani 1 2 d S T P . .
K1 K 0.500000 0.7800(4) 0.4780(4) 0.0324(9) Uani 0.5 2 d S T P A 1
O3 O 0.500000 0.9117(17) 0.2170(15) 0.055(4) Uiso 0.5 2 d S . P A 1
K2 K 0.500000 0.5218(5) 0.2196(4) 0.0345(9) Uani 0.5 2 d S T P A 2
O4 O 0.500000 0.7803(17) 0.0874(19) 0.064(4) Uiso 0.5 2 d S . P 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.254(5) 4_566 ?
C1 O2 1.254(5) . ?
C1 C2 1.516(10) . ?
C2 C3 1.393(6) . ?
C2 C3 1.393(6) 4_566 ?
C3 C4 1.389(7) . ?
C3 I1 2.109(5) . ?
C4 C5 1.410(6) . ?
C4 I2 2.098(4) . ?
C5 I3 2.079(7) . ?
O1 K1 2.793(5) 9_676 ?
O1 K1 2.793(5) . ?
O1 K2 2.793(6) 10_566 ?
O1 K2 2.793(6) 2_665 ?
O2 K1 2.777(4) . ?
O2 K2 2.780(4) . ?
K1 O3 2.710(15) . ?
K1 O3 2.839(16) 2_665 ?
K1 K1 4.093(7) 9_676 ?
K1 K1 4.6702(9) 2_664 ?
K1 K1 4.6702(9) 2_665 ?
K2 O4 2.689(16) . ?
K2 O4 2.863(17) 10_556 ?
K2 K2 4.094(7) 9_665 ?
K2 K2 4.6623(9) 10_556 ?
K2 K2 4.6623(10) 10_566 ?

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
O2 C1 O2 125.2(7) 4_566 . ?
O2 C1 C2 117.4(4) 4_566 . ?
O2 C1 C2 117.4(4) . . ?
C3 C2 C3 119.4(6) . 4_566 ?
C3 C2 C1 120.3(3) . . ?
C3 C2 C1 120.3(3) 4_566 . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 I1 121.7(3) . . ?
C2 C3 I1 117.5(4) . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 I2 120.2(3) . . ?
C5 C4 I2 119.7(4) . . ?
C4 C5 C4 118.8(6) 4_566 . ?
C4 C5 I3 120.6(3) 4_566 . ?
C4 C5 I3 120.6(3) . . ?
K1 O1 K1 94.2(2) 9_676 . ?
K1 O1 K2 62.46(16) 9_676 10_566 ?
K1 O1 K2 62.37(16) . 10_566 ?
K1 O1 K2 62.37(16) 9_676 2_665 ?
K1 O1 K2 62.46(16) . 2_665 ?
C1 O2 K1 127.6(3) . . ?
C1 O2 K2 127.8(3) . . ?
O3 K1 O2 96.0(3) . 12_655 ?
O3 K1 O2 96.0(3) . . ?
O2 K1 O2 93.75(19) 12_655 . ?
O3 K1 O1 74.8(3) . 9_676 ?
O2 K1 O1 89.59(13) 12_655 9_676 ?
O2 K1 O1 170.47(17) . 9_676 ?
O3 K1 O1 74.8(3) . . ?
O2 K1 O1 170.47(17) 12_655 . ?
O2 K1 O1 89.59(13) . . ?
O1 K1 O1 85.8(2) 9_676 . ?
O3 K1 O3 168.0(4) . 2_665 ?
O2 K1 O3 76.0(2) 12_655 2_665 ?
O2 K1 O3 76.0(2) . 2_665 ?
O1 K1 O3 113.5(2) 9_676 2_665 ?
O1 K1 O3 113.5(2) . 2_665 ?
O3 K1 K1 69.0(4) . 9_676 ?
O2 K1 K1 131.92(10) 12_655 9_676 ?
O2 K1 K1 131.92(10) . 9_676 ?
O1 K1 K1 42.89(12) 9_676 9_676 ?
O1 K1 K1 42.89(12) . 9_676 ?
O3 K1 K1 123.0(4) 2_665 9_676 ?
O3 K1 K1 33.6(3) . 2_664 ?
O2 K1 K1 73.34(12) 12_655 2_664 ?
O2 K1 K1 73.34(12) . 2_664 ?
O1 K1 K1 99.16(11) 9_676 2_664 ?
O1 K1 K1 99.16(11) . 2_664 ?
O3 K1 K1 134.5(3) 2_665 2_664 ?
K1 K1 K1 102.55(15) 9_676 2_664 ?
O3 K1 K1 160.1(4) . 2_665 ?
O2 K1 K1 97.58(13) 12_655 2_665 ?
O2 K1 K1 97.58(13) . 2_665 ?
O1 K1 K1 90.82(10) 9_676 2_665 ?
O1 K1 K1 90.82(10) . 2_665 ?
O3 K1 K1 31.9(3) 2_665 2_665 ?
K1 K1 K1 91.12(14) 9_676 2_665 ?
K1 K1 K1 166.33(18) 2_664 2_665 ?
K1 O3 K1 114.6(6) . 2_664 ?
O4 K2 O2 96.3(3) . . ?
O2 K2 O2 93.63(18) . 12_655 ?
O2 K2 O1 170.49(19) . 2_664 ?
O2 K2 O1 89.66(13) 12_655 2_664 ?
O2 K2 O1 89.66(13) . 10_556 ?
O2 K2 O1 170.49(19) 12_655 10_556 ?
O1 K2 O1 85.8(2) 2_664 10_556 ?
O4 K2 O4 168.4(4) . 10_556 ?
O2 K2 O4 75.9(2) . 10_556 ?
O2 K2 O4 75.9(2) 12_655 10_556 ?
O1 K2 O4 113.5(3) 2_664 10_556 ?
O1 K2 O4 113.5(3) 10_556 10_556 ?
O2 K2 K2 131.98(10) . 9_665 ?
O2 K2 K2 131.98(10) 12_655 9_665 ?
O1 K2 K2 42.88(12) 2_664 9_665 ?
O1 K2 K2 42.88(12) 10_556 9_665 ?
O2 K2 K2 97.47(14) . 10_556 ?
O2 K2 K2 97.47(14) 12_655 10_556 ?
O1 K2 K2 90.94(10) 2_664 10_556 ?
O1 K2 K2 90.94(10) 10_556 10_556 ?
O2 K2 K2 73.30(12) . 10_566 ?
O2 K2 K2 73.30(12) 12_655 10_566 ?
O1 K2 K2 99.19(11) 2_664 10_566 ?
O1 K2 K2 99.19(11) 10_556 10_566 ?

_refine_diff_density_max         1.327
_refine_diff_density_min         -1.180
_refine_diff_density_rms         0.253

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2

####################################################################### 
# 
# 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_SAC6I5COOHandEt3N_a
_database_code_depnum_ccdc_archive 'CCDC 1919377'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 I5 N O2'
_chemical_formula_weight         852.77

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   17.9973(6)
_cell_length_b                   11.0540(5)
_cell_length_c                   10.3194(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2052.96(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    6009
_cell_measurement_theta_min      3.8220
_cell_measurement_theta_max      28.8680

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.759
_exptl_crystal_F_000             1528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    7.578
_shelx_estimated_absorpt_T_min   0.342
_shelx_estimated_absorpt_T_max   0.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66536
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            14763
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.524
_diffrn_reflns_theta_max         29.007
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             4615
_reflns_number_gt                4352
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_max     0.764
_reflns_Friedel_fraction_full    0.959

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0342P)²+11.3404P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1709 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4615
_refine_ls_number_parameters     193
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5005(6) 0.2667(10) 0.5691(12) 0.0154(15) Uani 1 1 d . U . . .
C2 C 0.4443(6) 0.2281(12) 0.4875(11) 0.017(3) Uani 1 1 d . . . . .
C3 C 0.3763(6) 0.2949(11) 0.4843(11) 0.015(2) Uani 1 1 d . . . . .
C4 C 0.3678(6) 0.3999(11) 0.5569(12) 0.017(2) Uani 1 1 d . . . . .
C5 C 0.4261(6) 0.4368(11) 0.6371(12) 0.0153(15) Uani 1 1 d . U . . .
C6 C 0.4934(6) 0.3706(11) 0.6465(12) 0.0153(14) Uani 1 1 d . U . . .
C7 C 0.2982(7) 0.4738(11) 0.5433(10) 0.016(3) Uani 1 1 d . . . . .
C8 C 0.1761(11) 0.5471(16) 0.2172(18) 0.051(5) Uani 1 1 d . . . . .
H8A H 0.194893 0.602823 0.150913 0.076 Uiso 1 1 calc R U . . .
H8B H 0.144081 0.486419 0.176391 0.076 Uiso 1 1 calc R U . . .
H8C H 0.218047 0.506746 0.259667 0.076 Uiso 1 1 calc R U . . .
C9 C 0.1338(10) 0.6144(17) 0.3128(18) 0.047(4) Uani 1 1 d . . . . .
H9A H 0.102689 0.557325 0.363111 0.057 Uiso 1 1 calc R U . . .
H9B H 0.100067 0.671263 0.267612 0.057 Uiso 1 1 calc R U . . .
C10 C 0.2184(9) 0.7894(14) 0.3439(15) 0.037(4) Uani 1 1 d . . . . .
H10A H 0.179628 0.848384 0.318800 0.044 Uiso 1 1 calc R U . . .
H10B H 0.243579 0.762033 0.263823 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2750(11) 0.8524(17) 0.431(2) 0.056(5) Uani 1 1 d . . . . .
H11A H 0.249127 0.893498 0.501671 0.084 Uiso 1 1 calc R U . . .
H11B H 0.302900 0.911801 0.379726 0.084 Uiso 1 1 calc R U . . .
H11C H 0.309384 0.792240 0.466441 0.084 Uiso 1 1 calc R U . . .
C12 C 0.1404(9) 0.7028(16) 0.5275(17) 0.042(2) Uani 1 1 d . U . . .
H12A H 0.173934 0.737057 0.594102 0.050 Uiso 1 1 calc R U . . .
H12B H 0.123219 0.622941 0.558950 0.050 Uiso 1 1 calc R U . . .
C13 C 0.0745(9) 0.7844(16) 0.5128(18) 0.043(2) Uani 1 1 d . U . . .
H13A H 0.090774 0.863143 0.479761 0.064 Uiso 1 1 calc R U . . .
H13B H 0.050435 0.795177 0.597235 0.064 Uiso 1 1 calc R U . . .
H13C H 0.039137 0.748191 0.451878 0.064 Uiso 1 1 calc R U . . .
N1 N 0.1829(7) 0.6854(12) 0.4058(12) 0.041(2) Uani 1 1 d . U . . .
H1 H 0.224458 0.629255 0.428892 0.049 Uiso 1 1 calc R U . . .
O1 O 0.2441(5) 0.4554(8) 0.6157(8) 0.0205(19) Uani 1 1 d . . . . .
O2 O 0.3006(5) 0.5494(9) 0.4506(10) 0.031(2) Uani 1 1 d . . . . .
I1 I 0.28514(4) 0.23416(9) 0.37428(10) 0.0288(2) Uani 1 1 d . . . . .
I2 I 0.45483(5) 0.07678(8) 0.36724(9) 0.0264(2) Uani 1 1 d . . . . .
I3 I 0.60077(4) 0.16660(7) 0.58001(9) 0.02055(18) Uani 1 1 d . . . . .
I4 I 0.57758(4) 0.42471(8) 0.77426(8) 0.0254(2) Uani 1 1 d . . . . .
I5 I 0.40859(4) 0.59555(8) 0.74754(9) 0.0252(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(16) . ?
C1 C6 1.405(17) . ?
C1 I3 2.120(11) . ?
C2 C3 1.429(16) . ?
C2 I2 2.091(13) . ?
C3 C4 1.390(17) . ?
C3 I1 2.106(11) . ?
C4 C5 1.397(16) . ?
C4 C7 1.502(16) . ?
C5 C6 1.417(17) . ?
C5 I5 2.117(12) . ?
C6 I4 2.096(12) . ?
C7 O1 1.245(14) . ?
C7 O2 1.271(14) . ?
C8 C9 1.45(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N1 1.52(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N1 1.462(19) . ?
C10 C11 1.52(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N1 1.483(19) . ?
C12 C13 1.50(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 H1 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.2(11) . . ?
C2 C1 I3 119.6(9) . . ?
C6 C1 I3 118.3(8) . . ?
C1 C2 C3 118.7(11) . . ?
C1 C2 I2 122.8(9) . . ?
C3 C2 I2 118.5(8) . . ?
C4 C3 C2 120.9(11) . . ?
C4 C3 I1 118.1(8) . . ?
C2 C3 I1 121.0(8) . . ?
C3 C4 C5 118.7(11) . . ?
C3 C4 C7 119.7(11) . . ?
C5 C4 C7 121.5(11) . . ?
C4 C5 C6 122.1(11) . . ?
C4 C5 I5 116.7(8) . . ?
C6 C5 I5 121.2(8) . . ?
C1 C6 C5 117.4(11) . . ?
C1 C6 I4 121.7(9) . . ?
C5 C6 I4 120.9(9) . . ?
O1 C7 O2 125.8(11) . . ?
O1 C7 C4 120.5(10) . . ?
O2 C7 C4 113.6(10) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C8 C9 N1 112.8(15) . . ?
C8 C9 H9A 109.0 . . ?
N1 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
N1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N1 C10 C11 113.2(14) . . ?
N1 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 113.7(14) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 N1 C12 119.5(13) . . ?
C10 N1 C9 112.6(12) . . ?
C12 N1 C9 107.5(14) . . ?
C10 N1 H1 105.4 . . ?
C12 N1 H1 105.4 . . ?
C9 N1 H1 105.4 . . ?

_refine_diff_density_max         1.331
_refine_diff_density_min         -1.327
_refine_diff_density_rms         0.196

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
####################################################################### 
# 
# 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_SAC6I5COOHandPr3N_a
_database_code_depnum_ccdc_archive 'CCDC 1919378'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H29 I5 N2 O3'
_chemical_formula_weight         967.94

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.2333(4)
_cell_length_b                   15.4642(9)
_cell_length_c                   20.9533(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2667.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3379
_cell_measurement_theta_min      4.0290
_cell_measurement_theta_max      28.0040

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.410
_exptl_crystal_F_000             1784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    5.851
_shelx_estimated_absorpt_T_min   0.227
_shelx_estimated_absorpt_T_max   0.720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66355
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            9747
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.412
_diffrn_reflns_theta_max         29.017
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.773
_diffrn_reflns_point_group_measured_fraction_full 0.942
_reflns_number_total             5491
_reflns_number_gt                5001
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_max     0.668
_reflns_Friedel_fraction_full    0.870

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0206P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5491
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0614
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4054(10) 0.8944(5) 0.6553(4) 0.0129(18) Uani 1 1 d . . . . .
I1 I 0.50812(7) 0.78358(4) 0.77701(3) 0.01931(14) Uani 1 1 d . . . . .
N1 N -0.0010(8) 0.8931(4) 0.7265(3) 0.0161(16) Uani 1 1 d . . . . .
H1 H 0.114368 0.896327 0.711664 0.019 Uiso 1 1 calc R U . . .
O1 O 0.3613(11) 0.3049(4) 0.5572(5) 0.060(3) Uani 1 1 d . . . . .
C2 C 0.3781(9) 0.7982(5) 0.6430(4) 0.0110(17) Uani 1 1 d . . . . .
N2 N 0.4346(9) 0.1640(5) 0.5596(4) 0.0224(18) Uani 1 1 d . . . . .
I2 I 0.53530(7) 0.56008(3) 0.73779(3) 0.01663(13) Uani 1 1 d . . . . .
O2 O 0.5366(7) 0.9226(3) 0.6361(3) 0.0172(13) Uani 1 1 d . . . . .
C3 C 0.3085(10) 0.7687(5) 0.5864(4) 0.0128(17) Uani 1 1 d . . . . .
I3 I 0.20108(7) 0.86416(4) 0.52714(3) 0.01773(14) Uani 1 1 d . . . . .
O3 O 0.2965(7) 0.9339(3) 0.6852(3) 0.0155(13) Uani 1 1 d . . . . .
C4 C 0.3019(10) 0.6811(5) 0.5714(4) 0.0120(18) Uani 1 1 d . . . . .
I4 I 0.37913(8) 0.48864(3) 0.58862(3) 0.02263(15) Uani 1 1 d . . . . .
C5 C 0.3704(10) 0.6211(5) 0.6137(4) 0.0156(19) Uani 1 1 d . . . . .
I5 I 0.19137(7) 0.64033(3) 0.48536(3) 0.01512(13) Uani 1 1 d . . . . .
C6 C 0.4331(10) 0.6471(5) 0.6721(4) 0.0157(19) Uani 1 1 d . . . . .
C7 C 0.4323(9) 0.7368(5) 0.6862(4) 0.0131(18) Uani 1 1 d . . . . .
C8 C 0.1311(14) 0.8652(8) 0.8998(5) 0.043(3) Uani 1 1 d . . . . .
H8A1 H 0.029614 0.840620 0.916167 0.064 Uiso 1 1 calc R U . . .
H8A2 H 0.178749 0.903402 0.932052 0.064 Uiso 1 1 calc R U . . .
H8A3 H 0.207385 0.818356 0.890016 0.064 Uiso 1 1 calc R U . . .
C9 C 0.0963(12) 0.9167(6) 0.8393(4) 0.026(2) Uani 1 1 d . . . . .
H9A1 H 0.032608 0.969089 0.849934 0.031 Uiso 1 1 calc R U . . .
H9A2 H 0.199576 0.935163 0.819328 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0021(12) 0.8607(6) 0.7938(4) 0.024(2) Uani 1 1 d . . . . .
H10A H 0.049831 0.801956 0.794115 0.029 Uiso 1 1 calc R U . . .
H10B H -0.111069 0.855887 0.809371 0.029 Uiso 1 1 calc R U . . .
C11 C -0.0876(10) 0.8338(5) 0.6821(4) 0.018(2) Uani 1 1 d . . . . .
H11A H -0.061020 0.850683 0.637746 0.022 Uiso 1 1 calc R U . . .
H11B H -0.205993 0.841796 0.687969 0.022 Uiso 1 1 calc R U . . .
C12 C -0.0477(11) 0.7382(5) 0.6907(5) 0.022(2) Uani 1 1 d . . . . .
H12A H 0.071535 0.730367 0.693026 0.027 Uiso 1 1 calc R U . . .
H12B H -0.095691 0.716828 0.731041 0.027 Uiso 1 1 calc R U . . .
C13 C -0.1156(12) 0.6872(5) 0.6346(5) 0.026(2) Uani 1 1 d . . . . .
H13A H -0.233376 0.695931 0.632188 0.039 Uiso 1 1 calc R U . . .
H13B H -0.092385 0.625618 0.640626 0.039 Uiso 1 1 calc R U . . .
H13C H -0.064940 0.707323 0.595009 0.039 Uiso 1 1 calc R U . . .
C14 C -0.0692(11) 0.9833(6) 0.7228(5) 0.022(2) Uani 1 1 d . . . . .
H14A H -0.000858 1.022358 0.748883 0.027 Uiso 1 1 calc R U . . .
H14B H -0.179793 0.983409 0.741381 0.027 Uiso 1 1 calc R U . . .
C15 C -0.0776(11) 1.0181(5) 0.6553(5) 0.023(2) Uani 1 1 d . . . . .
H15A H -0.167823 0.989872 0.632047 0.027 Uiso 1 1 calc R U . . .
H15B H 0.024890 1.005035 0.632603 0.027 Uiso 1 1 calc R U . . .
C16 C -0.1051(12) 1.1169(6) 0.6570(5) 0.030(2) Uani 1 1 d . . . . .
H16A H -0.208783 1.129398 0.677991 0.045 Uiso 1 1 calc R U . . .
H16B H -0.107243 1.139393 0.613284 0.045 Uiso 1 1 calc R U . . .
H16C H -0.016605 1.144451 0.680745 0.045 Uiso 1 1 calc R U . . .
C17 C 0.4584(14) 0.2461(6) 0.5469(6) 0.036(3) Uani 1 1 d . . . . .
H17 H 0.559430 0.261475 0.528163 0.043 Uiso 1 1 calc R U . . .
C18 C 0.2808(12) 0.1344(8) 0.5863(6) 0.040(3) Uani 1 1 d . . . . .
H18A H 0.228190 0.182198 0.609022 0.060 Uiso 1 1 calc R U . . .
H18B H 0.300827 0.086675 0.615995 0.060 Uiso 1 1 calc R U . . .
H18C H 0.209849 0.114506 0.551703 0.060 Uiso 1 1 calc R U . . .
C19 C 0.5565(14) 0.0985(7) 0.5469(6) 0.043(3) Uani 1 1 d . . . . .
H19A H 0.650826 0.125262 0.526327 0.064 Uiso 1 1 calc R U . . .
H19B H 0.510808 0.054252 0.518594 0.064 Uiso 1 1 calc R U . . .
H19C H 0.590162 0.071604 0.587129 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.233(9) . ?
C1 O3 1.253(10) . ?
C1 C2 1.527(11) . ?
I1 C7 2.129(8) . ?
N1 C11 1.487(11) . ?
N1 C10 1.498(11) . ?
N1 C14 1.506(10) . ?
N1 H1 1.0000 . ?
O1 C17 1.231(12) . ?
C2 C7 1.387(11) . ?
C2 C3 1.393(11) . ?
N2 C17 1.312(12) . ?
N2 C19 1.451(12) . ?
N2 C18 1.458(12) . ?
I2 C6 2.101(8) . ?
C3 C4 1.392(11) . ?
C3 I3 2.122(8) . ?
C4 C5 1.401(12) . ?
C4 I5 2.115(9) . ?
I4 C5 2.116(8) . ?
C5 C6 1.388(12) . ?
C6 C7 1.418(11) . ?
C8 C9 1.524(13) . ?
C8 H8A1 0.9800 . ?
C8 H8A2 0.9800 . ?
C8 H8A3 0.9800 . ?
C9 C10 1.504(12) . ?
C9 H9A1 0.9900 . ?
C9 H9A2 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.525(11) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.522(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.514(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.544(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O3 128.1(8) . . ?
O2 C1 C2 114.8(7) . . ?
O3 C1 C2 117.1(7) . . ?
C11 N1 C10 113.0(7) . . ?
C11 N1 C14 111.1(7) . . ?
C10 N1 C14 111.3(7) . . ?
C11 N1 H1 107.0 . . ?
C10 N1 H1 107.0 . . ?
C14 N1 H1 107.0 . . ?
C7 C2 C3 117.7(7) . . ?
C7 C2 C1 120.6(7) . . ?
C3 C2 C1 121.6(7) . . ?
C17 N2 C19 122.4(9) . . ?
C17 N2 C18 120.7(9) . . ?
C19 N2 C18 116.9(8) . . ?
C4 C3 C2 121.8(8) . . ?
C4 C3 I3 121.9(6) . . ?
C2 C3 I3 116.2(6) . . ?
C3 C4 C5 119.0(8) . . ?
C3 C4 I5 120.0(6) . . ?
C5 C4 I5 121.0(6) . . ?
C6 C5 C4 121.1(7) . . ?
C6 C5 I4 119.1(6) . . ?
C4 C5 I4 119.8(6) . . ?
C5 C6 C7 117.8(8) . . ?
C5 C6 I2 122.8(6) . . ?
C7 C6 I2 119.4(6) . . ?
C2 C7 C6 122.3(8) . . ?
C2 C7 I1 116.5(6) . . ?
C6 C7 I1 121.2(6) . . ?
C9 C8 H8A1 109.5 . . ?
C9 C8 H8A2 109.5 . . ?
H8A1 C8 H8A2 109.5 . . ?
C9 C8 H8A3 109.5 . . ?
H8A1 C8 H8A3 109.5 . . ?
H8A2 C8 H8A3 109.5 . . ?
C10 C9 C8 108.8(8) . . ?
C10 C9 H9A1 109.9 . . ?
C8 C9 H9A1 109.9 . . ?
C10 C9 H9A2 109.9 . . ?
C8 C9 H9A2 109.9 . . ?
H9A1 C9 H9A2 108.3 . . ?
N1 C10 C9 114.4(7) . . ?
N1 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
N1 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N1 C11 C12 114.8(7) . . ?
N1 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
N1 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 109.4(8) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 113.2(7) . . ?
N1 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 109.7(8) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 N2 125.6(11) . . ?
O1 C17 H17 117.2 . . ?
N2 C17 H17 117.2 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.870
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.171

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
####################################################################### 
# 
# 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_SA2169_a
_database_code_depnum_ccdc_archive 'CCDC 1919379'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H28 I5 N O2'
_chemical_formula_weight         936.92

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   8.3240(4)
_cell_length_b                   16.4369(6)
_cell_length_c                   9.5423(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.004(4)
_cell_angle_gamma                90
_cell_volume                     1292.87(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3973
_cell_measurement_theta_min      4.2620
_cell_measurement_theta_max      28.5940

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.407
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    6.029
_shelx_estimated_absorpt_T_min   0.227
_shelx_estimated_absorpt_T_max   0.584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            9442
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.499
_diffrn_reflns_theta_max         28.834
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_point_group_measured_fraction_full 0.920
_reflns_number_total             5135
_reflns_number_gt                4930
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_max     0.636
_reflns_Friedel_fraction_full    0.838

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0314P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1899 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5135
_refine_ls_number_parameters     250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.19677(9) 0.39135(4) 0.77169(8) 0.03176(17) Uani 1 1 d . . . . .
O1 O 0.0081(8) 0.4648(4) 0.4246(7) 0.0249(14) Uani 1 1 d . . . . .
N1 N 0.5933(10) 0.4726(5) 0.4685(9) 0.0227(18) Uani 1 1 d . . . . .
H1 H 0.507(14) 0.481(7) 0.475(12) 0.027 Uiso 1 1 d . U . . .
C1 C 0.1353(11) 0.5152(6) 0.7511(10) 0.0192(19) Uani 1 1 d . . . . .
C2 C 0.1100(12) 0.5638(6) 0.8657(10) 0.020(2) Uani 1 1 d . . . . .
O2 O 0.2734(9) 0.4825(5) 0.4529(9) 0.036(2) Uani 1 1 d . . . . .
I2 I 0.14306(9) 0.51503(4) 1.07224(7) 0.03006(17) Uani 1 1 d . . . . .
C3 C 0.0614(11) 0.6455(5) 0.8419(10) 0.0181(19) Uani 1 1 d . . . . .
I3 I 0.00117(9) 0.71913(5) 1.00682(7) 0.03170(17) Uani 1 1 d . . . . .
C4 C 0.0494(10) 0.6783(6) 0.7059(10) 0.0182(18) Uani 1 1 d . . . . .
I4 I -0.00948(7) 0.80222(3) 0.66501(7) 0.02129(14) Uani 1 1 d . . . . .
C5 C 0.0828(10) 0.6291(6) 0.5936(10) 0.0170(19) Uani 1 1 d . . . . .
I5 I 0.08231(8) 0.67485(4) 0.38776(7) 0.02463(15) Uani 1 1 d . . . . .
C6 C 0.1187(11) 0.5480(6) 0.6128(10) 0.019(2) Uani 1 1 d . . . . .
C9 C 0.5484(13) 0.5988(7) 0.3156(12) 0.035(3) Uani 1 1 d . . . . .
H9A H 0.553822 0.567459 0.227821 0.042 Uiso 1 1 calc R U . . .
H9B H 0.434831 0.596639 0.335391 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5891(15) 0.6837(8) 0.2900(17) 0.056(4) Uani 1 1 d . . . . .
H8A H 0.705551 0.686435 0.279119 0.067 Uiso 1 1 calc R U . . .
H8B H 0.574011 0.715876 0.374856 0.067 Uiso 1 1 calc R U . . .
C7 C 0.4954(15) 0.7224(9) 0.1659(14) 0.055(4) Uani 1 1 d . . . . .
H7A H 0.454895 0.680619 0.096718 0.082 Uiso 1 1 calc R U . . .
H7B H 0.565170 0.760397 0.123068 0.082 Uiso 1 1 calc R U . . .
H7C H 0.403589 0.752127 0.195319 0.082 Uiso 1 1 calc R U . . .
C00C C 0.1379(12) 0.4928(5) 0.4835(10) 0.018(2) Uani 1 1 d . . . . .
C10 C 0.6549(13) 0.5573(6) 0.4355(13) 0.033(3) Uani 1 1 d . . . . .
H10A H 0.660573 0.591586 0.521337 0.040 Uiso 1 1 calc R U . . .
H10B H 0.766042 0.552402 0.410656 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4605(16) 0.1994(7) 0.2400(16) 0.049(3) Uani 1 1 d . . . . .
H11A H 0.550111 0.170354 0.296200 0.074 Uiso 1 1 calc R U . . .
H11B H 0.437364 0.174289 0.146143 0.074 Uiso 1 1 calc R U . . .
H11C H 0.363701 0.196304 0.287659 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5067(15) 0.2868(7) 0.2245(13) 0.042(3) Uani 1 1 d . . . . .
H12A H 0.419210 0.314546 0.161352 0.050 Uiso 1 1 calc R U . . .
H12B H 0.606430 0.289216 0.178951 0.050 Uiso 1 1 calc R U . . .
C13 C 0.5364(12) 0.3326(6) 0.3659(11) 0.027(2) Uani 1 1 d . . . . .
H13A H 0.433956 0.336318 0.407155 0.032 Uiso 1 1 calc R U . . .
H13B H 0.616535 0.302632 0.433181 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5993(12) 0.4170(6) 0.3422(11) 0.027(2) Uani 1 1 d . . . . .
H14A H 0.533642 0.441213 0.257993 0.032 Uiso 1 1 calc R U . . .
H14B H 0.712714 0.413061 0.322632 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6860(17) 0.4917(9) 0.9956(13) 0.051(4) Uani 1 1 d . . . . .
H15A H 0.744104 0.543588 0.997851 0.077 Uiso 1 1 calc R U . . .
H15B H 0.724668 0.460494 1.081269 0.077 Uiso 1 1 calc R U . . .
H15C H 0.569440 0.501947 0.991368 0.077 Uiso 1 1 calc R U . . .
C16 C 0.7165(14) 0.4437(8) 0.8666(12) 0.042(3) Uani 1 1 d . . . . .
H16A H 0.658126 0.391125 0.865192 0.050 Uiso 1 1 calc R U . . .
H16B H 0.833860 0.431793 0.873031 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6614(13) 0.4890(7) 0.7300(11) 0.030(2) Uani 1 1 d . . . . .
H17A H 0.723391 0.540349 0.729358 0.036 Uiso 1 1 calc R U . . .
H17B H 0.545161 0.503092 0.725536 0.036 Uiso 1 1 calc R U . . .
C18 C 0.6852(12) 0.4389(7) 0.6000(11) 0.030(2) Uani 1 1 d . . . . .
H18A H 0.802038 0.437521 0.590405 0.036 Uiso 1 1 calc R U . . .
H18B H 0.649278 0.382366 0.613077 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.101(9) . ?
O1 C00C 1.236(12) . ?
N1 C18 1.483(13) . ?
N1 C14 1.519(13) . ?
N1 C10 1.531(13) . ?
N1 H1 0.74(11) . ?
C1 C2 1.394(13) . ?
C1 C6 1.414(13) . ?
C2 C3 1.411(12) . ?
C2 I2 2.111(9) . ?
O2 C00C 1.215(11) . ?
C3 C4 1.396(13) . ?
C3 I3 2.100(9) . ?
C4 C5 1.400(12) . ?
C4 I4 2.119(9) . ?
C5 C6 1.372(13) . ?
C5 I5 2.103(9) . ?
C6 C00C 1.558(12) . ?
C9 C8 1.465(16) . ?
C9 C10 1.508(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 C7 1.469(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.500(16) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.534(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.511(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.513(17) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.516(15) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.524(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C18 N1 C14 112.1(8) . . ?
C18 N1 C10 111.4(8) . . ?
C14 N1 C10 109.6(8) . . ?
C18 N1 H1 113(9) . . ?
C14 N1 H1 109(9) . . ?
C10 N1 H1 102(10) . . ?
C2 C1 C6 120.5(8) . . ?
C2 C1 I1 122.9(7) . . ?
C6 C1 I1 116.6(7) . . ?
C1 C2 C3 119.4(9) . . ?
C1 C2 I2 120.0(7) . . ?
C3 C2 I2 120.6(7) . . ?
C4 C3 C2 119.9(9) . . ?
C4 C3 I3 118.7(7) . . ?
C2 C3 I3 121.4(7) . . ?
C3 C4 C5 119.5(8) . . ?
C3 C4 I4 121.8(7) . . ?
C5 C4 I4 118.7(7) . . ?
C6 C5 C4 121.4(9) . . ?
C6 C5 I5 116.3(7) . . ?
C4 C5 I5 122.2(7) . . ?
C5 C6 C1 119.1(8) . . ?
C5 C6 C00C 120.3(8) . . ?
C1 C6 C00C 120.6(8) . . ?
C8 C9 C10 115.6(10) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
C9 C8 C7 116.0(11) . . ?
C9 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C00C O1 128.4(9) . . ?
O2 C00C C6 118.2(9) . . ?
O1 C00C C6 113.4(7) . . ?
C9 C10 N1 112.9(9) . . ?
C9 C10 H10A 109.0 . . ?
N1 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
N1 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C11 C12 C13 113.3(11) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 109.6(9) . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 N1 112.6(8) . . ?
C13 C14 H14A 109.1 . . ?
N1 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
N1 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C15 C16 C17 112.3(10) . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 112.1(9) . . ?
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 . . ?
N1 C18 C17 112.2(8) . . ?
N1 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
N1 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?

_refine_diff_density_max         0.976
_refine_diff_density_min         -1.008
_refine_diff_density_rms         0.154

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2

