# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Y-14
_database_code_depnum_ccdc_archive 'CCDC 2337941'
loop_
_audit_author_name
_audit_author_address
'Khalil A. Abboud'
;Department of Chemistry, University of Florida
United States of America
;

_audit_update_record             
;
2024-03-05 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 N2 O6'
_chemical_formula_weight         444.51

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      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                   12.0273(3)
_cell_length_b                   13.1402(4)
_cell_length_c                   14.3337(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2265.31(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.73

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      .

_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             952

_exptl_transmission_factor_min   0.5132
_exptl_transmission_factor_max   0.5657

_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.176
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.984

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_absorpt_process_details   
'Sheldrick, G. M., sadabs (2015). Acta Cryst. C71, 3-8.'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro source 3.0'
_diffrn_measurement_device_type  'D8 Venture with PHOTON III'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            39670
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.103
_diffrn_reflns_theta_max         32.798
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7501
_reflns_number_gt                6384
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.847
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 (Bruker, 2019)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2019)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXL2015, Sheldrick G. M. 2019'
_computing_structure_refinement  'SHELXL2015, Sheldrick G. M. 2019'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2019'
_computing_publication_material  'SHELXL2015, Sheldrick, G. M. 2019'

_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.0905P] 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 2412 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7501
_refine_ls_number_parameters     297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.011
_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 0.49320(11) 0.41022(12) 0.70724(10) 0.0287(3) Uani 1 1 d . . . . .
O1' O 0.70352(10) 0.72792(11) 0.44431(9) 0.0240(3) Uani 1 1 d . . . . .
O2 O 0.52538(10) 0.57444(12) 0.91266(9) 0.0258(3) Uani 1 1 d . . . . .
O2' O 0.86148(10) 0.81771(10) 0.46704(9) 0.0240(3) Uani 1 1 d . . . . .
O3 O 0.43522(10) 0.62153(11) 0.78263(9) 0.0254(3) Uani 1 1 d . . . . .
O1'' O 0.65512(9) 0.76086(10) 0.83055(8) 0.0190(2) Uani 1 1 d . . . . .
N1 N 0.75367(12) 0.92354(11) 0.71770(10) 0.0187(3) Uani 1 1 d . . . . .
N4 N 0.84348(11) 0.66426(12) 0.53478(10) 0.0188(3) Uani 1 1 d . . . . .
C1' C 0.79550(13) 0.73594(15) 0.47898(11) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.79275(13) 0.82431(14) 0.71912(11) 0.0177(3) Uani 1 1 d . . . . .
C2' C 0.80951(16) 0.90357(17) 0.42345(14) 0.0294(4) Uani 1 1 d . . . . .
H2'A H 0.863509 0.959070 0.417710 0.044 Uiso 1 1 calc R U . . .
H2'B H 0.782976 0.884149 0.361303 0.044 Uiso 1 1 calc R U . . .
H2'C H 0.746506 0.926203 0.461516 0.044 Uiso 1 1 calc R U . . .
C3 C 0.72339(12) 0.73678(13) 0.75094(11) 0.0168(3) Uani 1 1 d . . . . .
H3A H 0.774802 0.680448 0.769371 0.020 Uiso 1 1 calc R U . . .
C5 C 0.95779(13) 0.67811(15) 0.56986(12) 0.0203(3) Uani 1 1 d . . . . .
H5A H 0.998892 0.721867 0.525455 0.024 Uiso 1 1 calc R U . . .
H5B H 0.995109 0.610965 0.570936 0.024 Uiso 1 1 calc R U . . .
C6 C 0.96610(13) 0.72568(14) 0.66783(12) 0.0188(3) Uani 1 1 d . . . . .
H6A H 0.942746 0.674118 0.714225 0.023 Uiso 1 1 calc R U . . .
H6B H 1.045013 0.742188 0.680342 0.023 Uiso 1 1 calc R U . . .
C7 C 0.89813(13) 0.81995(14) 0.68257(11) 0.0175(3) Uani 1 1 d . . . . .
C8 C 0.92673(13) 0.92305(15) 0.65764(11) 0.0188(3) Uani 1 1 d . . . . .
C9 C 1.02110(14) 0.96698(16) 0.61666(12) 0.0226(4) Uani 1 1 d . . . . .
H9A H 1.083066 0.926201 0.599579 0.027 Uiso 1 1 calc R U . . .
C10 C 1.02204(15) 1.07071(16) 0.60168(12) 0.0253(4) Uani 1 1 d . . . . .
H10A H 1.085641 1.101175 0.574025 0.030 Uiso 1 1 calc R U . . .
C11 C 0.93157(15) 1.13214(15) 0.62623(12) 0.0232(4) Uani 1 1 d . . . . .
H11A H 0.935241 1.203398 0.615459 0.028 Uiso 1 1 calc R U . . .
C12 C 0.83655(14) 1.09072(14) 0.66606(12) 0.0208(3) Uani 1 1 d . . . . .
H12A H 0.774928 1.132218 0.682558 0.025 Uiso 1 1 calc R U . . .
C13 C 0.83509(13) 0.98594(14) 0.68089(11) 0.0183(3) Uani 1 1 d . . . . .
C14 C 0.64440(13) 0.69541(13) 0.67616(11) 0.0164(3) Uani 1 1 d . . . . .
H14A H 0.568658 0.721925 0.687994 0.020 Uiso 1 1 calc R U . . .
H14B H 0.668551 0.720619 0.614307 0.020 Uiso 1 1 calc R U . . .
C15 C 0.64036(13) 0.57905(13) 0.67404(11) 0.0173(3) Uani 1 1 d . . . . .
H15A H 0.579314 0.558647 0.630521 0.021 Uiso 1 1 calc R U . . .
C16 C 0.61311(13) 0.53403(14) 0.77132(12) 0.0186(3) Uani 1 1 d . . . . .
H16A H 0.679784 0.543790 0.812028 0.022 Uiso 1 1 calc R U . . .
C17 C 0.59018(14) 0.41912(15) 0.76456(13) 0.0230(4) Uani 1 1 d . . . . .
H17A H 0.573935 0.391488 0.828121 0.028 Uiso 1 1 calc R U . . .
C18 C 0.69126(16) 0.36544(15) 0.72427(13) 0.0255(4) Uani 1 1 d . . . . .
H18A H 0.672828 0.292960 0.713500 0.031 Uiso 1 1 calc R U . . .
H18B H 0.752636 0.368211 0.770223 0.031 Uiso 1 1 calc R U . . .
C19 C 0.73051(15) 0.41279(14) 0.63260(13) 0.0233(3) Uani 1 1 d . . . . .
H19A H 0.674460 0.398942 0.583641 0.028 Uiso 1 1 calc R U . . .
H19B H 0.800873 0.379752 0.613425 0.028 Uiso 1 1 calc R U . . .
C20 C 0.74930(14) 0.52843(14) 0.63909(11) 0.0191(3) Uani 1 1 d . . . . .
H20A H 0.809386 0.541746 0.685739 0.023 Uiso 1 1 calc R U . . .
C21 C 0.78963(14) 0.56437(14) 0.54259(12) 0.0204(3) Uani 1 1 d . . . . .
H21A H 0.842455 0.512791 0.518714 0.025 Uiso 1 1 calc R U . . .
H21B H 0.724672 0.564263 0.500165 0.025 Uiso 1 1 calc R U . . .
C22 C 0.51511(13) 0.58304(14) 0.81921(12) 0.0200(3) Uani 1 1 d . . . . .
C23 C 0.43572(16) 0.6177(2) 0.96643(14) 0.0345(5) Uani 1 1 d . . . . .
H23A H 0.450458 0.607817 1.033060 0.052 Uiso 1 1 calc R U . . .
H23B H 0.429971 0.690632 0.953022 0.052 Uiso 1 1 calc R U . . .
H23C H 0.365790 0.584007 0.949744 0.052 Uiso 1 1 calc R U . . .
C1'' C 0.71768(16) 0.78348(18) 0.91240(12) 0.0286(4) Uani 1 1 d . . . . .
H1'A H 0.666787 0.799149 0.963831 0.043 Uiso 1 1 calc R U . . .
H1'B H 0.763501 0.724569 0.929113 0.043 Uiso 1 1 calc R U . . .
H1'C H 0.765764 0.842288 0.900554 0.043 Uiso 1 1 calc R U . . .
H1 H 0.471(3) 0.347(3) 0.695(3) 0.104(14) Uiso 1 1 d . . . . .
H1A H 0.6871(19) 0.942(2) 0.7354(16) 0.032(6) 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 C17 1.431(2) . ?
O1 H1 0.89(4) . ?
O1' C1' 1.217(2) . ?
O2 C22 1.350(2) . ?
O2 C23 1.442(2) . ?
O2' C1' 1.347(2) . ?
O2' C2' 1.433(2) . ?
O3 C22 1.206(2) . ?
O1'' C1'' 1.425(2) . ?
O1'' C3 1.4410(19) . ?
N1 C13 1.382(2) . ?
N1 C2 1.386(2) . ?
N1 H1A 0.87(2) . ?
N4 C1' 1.364(2) . ?
N4 C21 1.468(2) . ?
N4 C5 1.475(2) . ?
C2 C7 1.373(2) . ?
C2 C3 1.492(2) . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C3 C14 1.532(2) . ?
C3 H3A 1.0000 . ?
C5 C6 1.540(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.499(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.443(3) . ?
C8 C9 1.402(2) . ?
C8 C13 1.417(2) . ?
C9 C10 1.380(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.400(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.389(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12A 0.9500 . ?
C14 C15 1.530(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.550(2) . ?
C15 C20 1.552(2) . ?
C15 H15A 1.0000 . ?
C16 C22 1.508(2) . ?
C16 C17 1.538(3) . ?
C16 H16A 1.0000 . ?
C17 C18 1.520(3) . ?
C17 H17A 1.0000 . ?
C18 C19 1.529(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.539(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.540(2) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C1'' H1'A 0.9800 . ?
C1'' H1'B 0.9800 . ?
C1'' H1'C 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
C17 O1 H1 116(3) . . ?
C22 O2 C23 115.39(14) . . ?
C1' O2' C2' 115.24(14) . . ?
C1'' O1'' C3 113.39(12) . . ?
C13 N1 C2 108.86(14) . . ?
C13 N1 H1A 126.5(17) . . ?
C2 N1 H1A 124.6(17) . . ?
C1' N4 C21 118.39(14) . . ?
C1' N4 C5 120.60(15) . . ?
C21 N4 C5 119.71(14) . . ?
O1' C1' O2' 123.55(17) . . ?
O1' C1' N4 124.35(17) . . ?
O2' C1' N4 112.10(14) . . ?
C7 C2 N1 110.29(15) . . ?
C7 C2 C3 126.92(16) . . ?
N1 C2 C3 122.67(14) . . ?
O2' C2' H2'A 109.5 . . ?
O2' C2' H2'B 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
O2' C2' H2'C 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
O1'' C3 C2 113.04(14) . . ?
O1'' C3 C14 106.18(12) . . ?
C2 C3 C14 113.97(13) . . ?
O1'' C3 H3A 107.8 . . ?
C2 C3 H3A 107.8 . . ?
C14 C3 H3A 107.8 . . ?
N4 C5 C6 114.91(13) . . ?
N4 C5 H5A 108.5 . . ?
C6 C5 H5A 108.5 . . ?
N4 C5 H5B 108.5 . . ?
C6 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C7 C6 C5 115.37(14) . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C2 C7 C8 105.99(15) . . ?
C2 C7 C6 126.28(16) . . ?
C8 C7 C6 127.67(14) . . ?
C9 C8 C13 119.21(17) . . ?
C9 C8 C7 133.10(16) . . ?
C13 C8 C7 107.69(14) . . ?
C10 C9 C8 118.58(17) . . ?
C10 C9 H9A 120.7 . . ?
C8 C9 H9A 120.7 . . ?
C9 C10 C11 121.61(16) . . ?
C9 C10 H10A 119.2 . . ?
C11 C10 H10A 119.2 . . ?
C12 C11 C10 121.14(18) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C13 117.41(17) . . ?
C11 C12 H12A 121.3 . . ?
C13 C12 H12A 121.3 . . ?
N1 C13 C12 130.80(16) . . ?
N1 C13 C8 107.16(16) . . ?
C12 C13 C8 122.04(15) . . ?
C15 C14 C3 112.84(13) . . ?
C15 C14 H14A 109.0 . . ?
C3 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C3 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 111.73(14) . . ?
C14 C15 C20 114.06(13) . . ?
C16 C15 C20 107.78(13) . . ?
C14 C15 H15A 107.7 . . ?
C16 C15 H15A 107.7 . . ?
C20 C15 H15A 107.7 . . ?
C22 C16 C17 107.92(14) . . ?
C22 C16 C15 114.32(14) . . ?
C17 C16 C15 110.85(14) . . ?
C22 C16 H16A 107.8 . . ?
C17 C16 H16A 107.8 . . ?
C15 C16 H16A 107.8 . . ?
O1 C17 C18 113.32(15) . . ?
O1 C17 C16 105.22(15) . . ?
C18 C17 C16 109.65(14) . . ?
O1 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C17 C18 C19 112.64(15) . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 113.28(15) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 107.14(14) . . ?
C19 C20 C15 108.58(14) . . ?
C21 C20 C15 115.10(14) . . ?
C19 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C15 C20 H20A 108.6 . . ?
N4 C21 C20 118.79(14) . . ?
N4 C21 H21A 107.6 . . ?
C20 C21 H21A 107.6 . . ?
N4 C21 H21B 107.6 . . ?
C20 C21 H21B 107.6 . . ?
H21A C21 H21B 107.0 . . ?
O3 C22 O2 122.65(16) . . ?
O3 C22 C16 127.15(15) . . ?
O2 C22 C16 110.14(14) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1'' C1'' H1'A 109.5 . . ?
O1'' C1'' H1'B 109.5 . . ?
H1'A C1'' H1'B 109.5 . . ?
O1'' C1'' H1'C 109.5 . . ?
H1'A C1'' H1'C 109.5 . . ?
H1'B C1'' H1'C 109.5 . . ?

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
_geom_hbond_publ_flag
C5 H5A O1' 0.99 2.58 3.210(2) 121.1 4_566 yes
C6 H6B O1' 0.99 2.64 3.333(2) 127.0 4_566 yes
C12 H12A O3 0.95 2.58 3.375(2) 141.4 3_656 yes
C14 H14A O3 0.99 2.48 3.099(2) 120.1 . yes
C14 H14B O1' 0.99 2.47 3.425(2) 160.8 . yes
C14 H14B N4 0.99 2.50 3.163(2) 123.7 . yes
C18 H18A O3 0.99 2.60 3.549(2) 160.3 3_646 yes
C21 H21A O2 0.99 2.48 3.427(2) 160.0 2_664 yes
O1 H1 O1'' 0.89(4) 1.93(4) 2.7070(19) 145(4) 3_646 yes
N1 H1A O1 0.87(2) 2.36(2) 3.1629(19) 153(2) 3_656 yes

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_Y-18
_database_code_depnum_ccdc_archive 'CCDC 2338890'
loop_
_audit_author_name
_audit_author_address
'Khalil A. Abboud'
;Department of Chemistry, University of Florida
United States of America
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H37 I N2 O6'
_chemical_formula_weight         660.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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                   12.2862(2)
_cell_length_b                   9.7856(2)
_cell_length_c                   13.1560(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.0549(7)
_cell_angle_gamma                90
_cell_volume                     1476.12(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.0

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    8.899
_shelx_estimated_absorpt_T_min   0.169
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_type   Multi
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
'based on measured indexed crystal faces, Bruker APEX3 (Bruker, 2014)'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            18451
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.600
_diffrn_reflns_theta_max         71.083
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.795
_diffrn_reflns_point_group_measured_fraction_full 0.875
_reflns_number_total             4534
_reflns_number_gt                4485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.541
_reflns_Friedel_fraction_max     0.595
_reflns_Friedel_fraction_full    0.719

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'
_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+0.5883P] 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 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4534
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0639
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.006
_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 0.21664(2) 0.20882(4) 0.90745(2) 0.04747(11) Uani 1 1 d . . . . .
O1 O 0.6088(3) 0.8643(3) 0.7004(3) 0.0326(6) Uani 1 1 d . . . . .
O1" O 0.3763(2) 0.3606(2) 0.65294(18) 0.0210(5) Uani 1 1 d . . . . .
O1' O 0.2613(2) 0.6311(3) 0.2636(2) 0.0347(6) Uani 1 1 d . . . . .
O2 O 0.6445(2) 0.5361(3) 0.81385(19) 0.0267(5) Uani 1 1 d . . . . .
O2' O 0.0775(3) 0.5542(3) 0.2261(2) 0.0373(7) Uani 1 1 d . . . . .
O3 O 0.6554(2) 0.5713(3) 0.6491(2) 0.0266(5) Uani 1 1 d . . . . .
N1 N 0.2046(2) 0.2618(3) 0.4439(2) 0.0214(6) Uani 1 1 d . . . . .
H1A H 0.2677 0.2114 0.4584 0.026 Uiso 1 1 calc R U . . .
N4 N 0.1570(2) 0.6926(3) 0.3692(2) 0.0241(6) Uani 1 1 d . . . . .
C1" C 0.3264(3) 0.3184(4) 0.7291(3) 0.0255(7) Uani 1 1 d . . . . .
H1"A H 0.2596 0.2569 0.6931 0.031 Uiso 1 1 calc R U . . .
H1"B H 0.2969 0.3991 0.7566 0.031 Uiso 1 1 calc R U . . .
C1' C 0.1720(3) 0.6267(4) 0.2848(3) 0.0269(7) Uani 1 1 d . . . . .
C2" C 0.4155(3) 0.2448(3) 0.8229(3) 0.0210(7) Uani 1 1 d . . . . .
C2 C 0.1984(3) 0.3858(3) 0.4919(3) 0.0196(6) Uani 1 1 d . . . . .
C2' C 0.0893(6) 0.4604(7) 0.1461(4) 0.0666(16) Uani 1 1 d . . . . .
H2'A H 0.1710 0.4280 0.1696 0.080 Uiso 1 1 calc R U . . .
H2'B H 0.0386 0.3800 0.1407 0.080 Uiso 1 1 calc R U . . .
C3" C 0.3867(3) 0.1869(4) 0.9064(3) 0.0244(7) Uani 1 1 d . . . . .
C3 C 0.3029(3) 0.4539(3) 0.5734(3) 0.0186(6) Uani 1 1 d . . . . .
H3A H 0.2737 0.5236 0.6131 0.022 Uiso 1 1 calc R U . . .
C3' C 0.0584(6) 0.5232(11) 0.0433(6) 0.090(3) Uani 1 1 d . . . . .
H3'A H 0.0671 0.4574 -0.0095 0.135 Uiso 1 1 calc R U . . .
H3'B H -0.0228 0.5540 0.0195 0.135 Uiso 1 1 calc R U . . .
H3'C H 0.1094 0.6019 0.0483 0.135 Uiso 1 1 calc R U . . .
C4" C 0.4661(3) 0.1129(4) 0.9905(3) 0.0305(8) Uani 1 1 d . . . . .
H4"A H 0.4436 0.0735 1.0459 0.037 Uiso 1 1 calc R U . . .
C5 C 0.0472(3) 0.6837(4) 0.3902(3) 0.0284(8) Uani 1 1 d . . . . .
H5A H -0.0174 0.6662 0.3204 0.034 Uiso 1 1 calc R U . . .
H5B H 0.0323 0.7731 0.4179 0.034 Uiso 1 1 calc R U . . .
C5" C 0.5784(3) 0.0975(5) 0.9922(3) 0.0343(9) Uani 1 1 d . . . . .
H5"A H 0.6337 0.0458 1.0483 0.041 Uiso 1 1 calc R U . . .
C6 C 0.0456(3) 0.5716(4) 0.4726(3) 0.0239(7) Uani 1 1 d . . . . .
H6A H 0.0954 0.6013 0.5466 0.029 Uiso 1 1 calc R U . . .
H6B H -0.0350 0.5620 0.4715 0.029 Uiso 1 1 calc R U . . .
C6" C 0.6103(3) 0.1578(4) 0.9118(3) 0.0324(8) Uani 1 1 d . . . . .
H6"A H 0.6884 0.1497 0.9145 0.039 Uiso 1 1 calc R U . . .
C7" C 0.5302(3) 0.2292(4) 0.8280(3) 0.0269(7) Uani 1 1 d . . . . .
H7"A H 0.5534 0.2684 0.7728 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0869(3) 0.4351(3) 0.4502(3) 0.0200(6) Uani 1 1 d . . . . .
C8 C 0.0196(3) 0.3377(4) 0.3715(3) 0.0218(7) Uani 1 1 d . . . . .
C9 C -0.0976(3) 0.3317(4) 0.3026(3) 0.0282(8) Uani 1 1 d . . . . .
H9A H -0.1499 0.4032 0.3027 0.034 Uiso 1 1 calc R U . . .
C10 C -0.1361(3) 0.2207(6) 0.2348(3) 0.0347(8) Uani 1 1 d . . . . .
H10A H -0.2154 0.2166 0.1874 0.042 Uiso 1 1 calc R U . . .
C11 C -0.0604(4) 0.1137(4) 0.2345(3) 0.0331(8) Uani 1 1 d . . . . .
H11A H -0.0895 0.0372 0.1882 0.040 Uiso 1 1 calc R U . . .
C12 C 0.0573(3) 0.1179(4) 0.3014(3) 0.0282(8) Uani 1 1 d . . . . .
H12A H 0.1092 0.0464 0.3004 0.034 Uiso 1 1 calc R U . . .
C13 C 0.0955(3) 0.2299(4) 0.3691(2) 0.0227(7) Uani 1 1 d . . . . .
C14 C 0.3818(3) 0.5284(3) 0.5231(3) 0.0188(6) Uani 1 1 d . . . . .
H14A H 0.3404 0.5351 0.4433 0.023 Uiso 1 1 calc R U . . .
H14B H 0.4531 0.4733 0.5360 0.023 Uiso 1 1 calc R U . . .
C15 C 0.4177(3) 0.6735(3) 0.5696(3) 0.0193(6) Uani 1 1 d . . . . .
H15A H 0.4670 0.7132 0.5308 0.023 Uiso 1 1 calc R U . . .
C16 C 0.4941(3) 0.6668(3) 0.6918(3) 0.0184(6) Uani 1 1 d . . . . .
H16A H 0.4481 0.6188 0.7301 0.022 Uiso 1 1 calc R U . . .
C17 C 0.5288(3) 0.8076(4) 0.7456(3) 0.0245(7) Uani 1 1 d . . . . .
H17A H 0.5692 0.7955 0.8259 0.029 Uiso 1 1 calc R U . . .
C18 C 0.4217(3) 0.8961(4) 0.7243(3) 0.0289(8) Uani 1 1 d . . . . .
H18A H 0.4459 0.9877 0.7564 0.035 Uiso 1 1 calc R U . . .
H18B H 0.3711 0.8549 0.7600 0.035 Uiso 1 1 calc R U . . .
C19 C 0.3533(3) 0.9105(4) 0.6028(3) 0.0277(8) Uani 1 1 d . . . . .
H19A H 0.4027 0.9556 0.5676 0.033 Uiso 1 1 calc R U . . .
H19B H 0.2842 0.9690 0.5915 0.033 Uiso 1 1 calc R U . . .
C20 C 0.3136(3) 0.7702(3) 0.5498(3) 0.0221(7) Uani 1 1 d . . . . .
H20A H 0.2604 0.7286 0.5836 0.027 Uiso 1 1 calc R U . . .
C21 C 0.2429(3) 0.7956(4) 0.4284(3) 0.0290(8) Uani 1 1 d . . . . .
H21A H 0.2014 0.8837 0.4224 0.035 Uiso 1 1 calc R U . . .
H21B H 0.2988 0.8068 0.3904 0.035 Uiso 1 1 calc R U . . .
C22 C 0.6047(3) 0.5861(4) 0.7118(3) 0.0216(7) Uani 1 1 d . . . . .
C23 C 0.7553(3) 0.4663(4) 0.8476(3) 0.0332(8) Uani 1 1 d . . . . .
H23A H 0.7758 0.4343 0.9228 0.050 Uiso 1 1 calc R U . . .
H23B H 0.7499 0.3880 0.7996 0.050 Uiso 1 1 calc R U . . .
H23C H 0.8156 0.5293 0.8434 0.050 Uiso 1 1 calc R U . . .
H1 H 0.628(5) 0.943(7) 0.721(5) 0.050(16) 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 C3" 2.106(3) . ?
O1 C17 1.431(5) . ?
O1 H1 0.82(6) . ?
O1" C1" 1.412(4) . ?
O1" C3 1.437(4) . ?
O1' C1' 1.226(5) . ?
O2 C22 1.345(4) . ?
O2 C23 1.443(5) . ?
O2' C1' 1.343(5) . ?
O2' C2' 1.442(6) . ?
O3 C22 1.208(5) . ?
N1 C2 1.383(4) . ?
N1 C13 1.384(4) . ?
N1 H1A 0.8800 . ?
N4 C1' 1.352(5) . ?
N4 C21 1.465(5) . ?
N4 C5 1.474(4) . ?
C1" C2" 1.506(5) . ?
C1" H1"A 0.9900 . ?
C1" H1"B 0.9900 . ?
C2" C3" 1.389(5) . ?
C2" C7" 1.396(5) . ?
C2 C7 1.367(5) . ?
C2 C3 1.501(5) . ?
C2' C3' 1.408(10) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C3" C4" 1.387(5) . ?
C3 C14 1.540(4) . ?
C3 H3A 1.0000 . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C3' H3'C 0.9800 . ?
C4" C5" 1.380(6) . ?
C4" H4"A 0.9500 . ?
C5 C6 1.547(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5" C6" 1.385(6) . ?
C5" H5"A 0.9500 . ?
C6 C7 1.495(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6" C7" 1.375(5) . ?
C6" H6"A 0.9500 . ?
C7" H7"A 0.9500 . ?
C7 C8 1.432(5) . ?
C8 C9 1.400(5) . ?
C8 C13 1.415(5) . ?
C9 C10 1.377(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.401(7) . ?
C10 H10A 0.9500 . ?
C11 C12 1.397(6) . ?
C11 H11A 0.9500 . ?
C12 C13 1.385(5) . ?
C12 H12A 0.9500 . ?
C14 C15 1.546(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C20 1.536(5) . ?
C15 C16 1.545(4) . ?
C15 H15A 1.0000 . ?
C16 C22 1.510(5) . ?
C16 C17 1.537(5) . ?
C16 H16A 1.0000 . ?
C17 C18 1.515(5) . ?
C17 H17A 1.0000 . ?
C18 C19 1.522(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.539(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.540(5) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C17 O1 H1 113(4) . . ?
C1" O1" C3 112.5(2) . . ?
C22 O2 C23 116.4(3) . . ?
C1' O2' C2' 117.6(4) . . ?
C2 N1 C13 108.9(3) . . ?
C2 N1 H1A 125.6 . . ?
C13 N1 H1A 125.6 . . ?
C1' N4 C21 118.7(3) . . ?
C1' N4 C5 122.0(3) . . ?
C21 N4 C5 118.3(3) . . ?
O1" C1" C2" 110.3(3) . . ?
O1" C1" H1"A 109.6 . . ?
C2" C1" H1"A 109.6 . . ?
O1" C1" H1"B 109.6 . . ?
C2" C1" H1"B 109.6 . . ?
H1"A C1" H1"B 108.1 . . ?
O1' C1' O2' 123.1(4) . . ?
O1' C1' N4 124.6(3) . . ?
O2' C1' N4 112.3(3) . . ?
C3" C2" C7" 117.2(3) . . ?
C3" C2" C1" 121.7(3) . . ?
C7" C2" C1" 121.1(3) . . ?
C7 C2 N1 109.8(3) . . ?
C7 C2 C3 127.3(3) . . ?
N1 C2 C3 122.9(3) . . ?
C3' C2' O2' 111.1(6) . . ?
C3' C2' H2'A 109.4 . . ?
O2' C2' H2'A 109.4 . . ?
C3' C2' H2'B 109.4 . . ?
O2' C2' H2'B 109.4 . . ?
H2'A C2' H2'B 108.0 . . ?
C4" C3" C2" 122.5(3) . . ?
C4" C3" I1 117.6(3) . . ?
C2" C3" I1 119.9(2) . . ?
O1" C3 C2 113.0(3) . . ?
O1" C3 C14 106.6(3) . . ?
C2 C3 C14 114.4(3) . . ?
O1" C3 H3A 107.5 . . ?
C2 C3 H3A 107.5 . . ?
C14 C3 H3A 107.5 . . ?
C2' C3' H3'A 109.5 . . ?
C2' C3' H3'B 109.5 . . ?
H3'A C3' H3'B 109.5 . . ?
C2' C3' H3'C 109.5 . . ?
H3'A C3' H3'C 109.5 . . ?
H3'B C3' H3'C 109.5 . . ?
C5" C4" C3" 118.9(3) . . ?
C5" C4" H4"A 120.6 . . ?
C3" C4" H4"A 120.6 . . ?
N4 C5 C6 114.6(3) . . ?
N4 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
N4 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C4" C5" C6" 119.8(4) . . ?
C4" C5" H5"A 120.1 . . ?
C6" C5" H5"A 120.1 . . ?
C7 C6 C5 113.9(3) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7" C6" C5" 120.8(4) . . ?
C7" C6" H6"A 119.6 . . ?
C5" C6" H6"A 119.6 . . ?
C6" C7" C2" 120.9(3) . . ?
C6" C7" H7"A 119.5 . . ?
C2" C7" H7"A 119.6 . . ?
C2 C7 C8 106.9(3) . . ?
C2 C7 C6 126.8(3) . . ?
C8 C7 C6 126.0(3) . . ?
C9 C8 C13 119.1(3) . . ?
C9 C8 C7 133.5(3) . . ?
C13 C8 C7 107.3(3) . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 H10A 119.4 . . ?
C11 C10 H10A 119.4 . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C13 C12 C11 117.6(4) . . ?
C13 C12 H12A 121.2 . . ?
C11 C12 H12A 121.2 . . ?
N1 C13 C12 130.8(3) . . ?
N1 C13 C8 107.1(3) . . ?
C12 C13 C8 122.0(3) . . ?
C3 C14 C15 113.5(3) . . ?
C3 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C3 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C20 C15 C16 111.1(3) . . ?
C20 C15 C14 113.4(3) . . ?
C16 C15 C14 110.7(3) . . ?
C20 C15 H15A 107.1 . . ?
C16 C15 H15A 107.1 . . ?
C14 C15 H15A 107.1 . . ?
C22 C16 C17 107.8(3) . . ?
C22 C16 C15 112.1(3) . . ?
C17 C16 C15 113.9(3) . . ?
C22 C16 H16A 107.6 . . ?
C17 C16 H16A 107.6 . . ?
C15 C16 H16A 107.6 . . ?
O1 C17 C18 112.4(3) . . ?
O1 C17 C16 105.9(3) . . ?
C18 C17 C16 110.4(3) . . ?
O1 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C17 C18 C19 111.3(3) . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 C20 111.1(3) . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C15 C20 C19 111.4(3) . . ?
C15 C20 C21 113.6(3) . . ?
C19 C20 C21 107.2(3) . . ?
C15 C20 H20A 108.2 . . ?
C19 C20 H20A 108.2 . . ?
C21 C20 H20A 108.2 . . ?
N4 C21 C20 118.0(3) . . ?
N4 C21 H21A 107.8 . . ?
C20 C21 H21A 107.8 . . ?
N4 C21 H21B 107.8 . . ?
C20 C21 H21B 107.8 . . ?
H21A C21 H21B 107.1 . . ?
O3 C22 O2 123.1(3) . . ?
O3 C22 C16 126.6(3) . . ?
O2 C22 C16 110.2(3) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
N1 H1A O3 0.88 2.39 3.072(4) 134.1 2_646
C3' H3'B I1 0.98 3.25 4.088(8) 145.1 2_556
C4" H4"A O2 0.95 2.48 3.400(4) 163.2 2_647
C5 H5A I1 0.99 3.14 4.097(3) 162.2 2_556
C14 H14A O1' 0.99 2.40 3.350(4) 160.3 .
C14 H14A N4 0.99 2.61 3.208(4) 118.7 .
C14 H14B O3 0.99 2.58 3.197(4) 120.4 .
C23 H23B O1' 0.98 2.64 3.567(5) 158.9 2_646
O1 H1 O1' 0.82(6) 2.26(6) 3.007(4) 153(5) 2_656

_refine_diff_density_max         0.904
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_V-27
_database_code_depnum_ccdc_archive 'CCDC 2338889'
loop_
_audit_author_name
_audit_author_address
'Khalil A. Abboud'
;Department of Chemistry, University of Florida
United States of America
;

_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H30 N2 O5'
_chemical_formula_weight         426.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0192 0.0096 '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 0.0330 0.0189 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0517 0.0336 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.382(3)
_cell_length_b                   7.3133(13)
_cell_length_c                   16.086(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.69(2)
_cell_angle_gamma                90
_cell_volume                     1067.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9737
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      69.96

_exptl_crystal_description       needles
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   0.5500
_exptl_transmission_factor_max   0.6617
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.728
_shelx_estimated_absorpt_T_min   0.751
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8262
_exptl_absorpt_correction_T_max  0.9567
_exptl_absorpt_process_details   
'Sheldrick, G. M., sadabs (2015). Acta Cryst. C71, 3-8.'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro source 3.0'
_diffrn_measurement_device_type  'D8 Venture with PHOTON III'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            36941
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.840
_diffrn_reflns_theta_max         70.085
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             3872
_reflns_number_gt                3861
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_max     0.930
_reflns_Friedel_fraction_full    0.935

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2015, Sheldrick G. M. 2015'
_computing_structure_refinement  'SHELXL2015, Sheldrick G. M. 2015'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2015, Sheldrick, G. M. 2015'

_refine_special_details          
; 
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and 
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). 
Methyl ones were allowed to rotate around the corresponding C---C. 

The absolute configuration is established by anomalous dispersion giving a
 value of 0.13(14) for the Flack x parameter.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.2024P] 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 1712 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.13(14)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3872
_refine_ls_number_parameters     284
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.09978(14) 0.1773(2) 0.86232(9) 0.0195(3) Uani 1 1 d . . . . .
O2 O 0.00202(15) 0.4374(2) 0.89985(10) 0.0232(3) Uani 1 1 d . . . . .
O3 O 0.53890(14) 0.39789(18) 0.88333(8) 0.0160(3) Uani 1 1 d . . . . .
O4 O 0.66194(15) 0.9319(2) 0.69932(10) 0.0225(3) Uani 1 1 d . . . . .
O5 O 0.74461(14) 0.6648(2) 0.65793(9) 0.0180(3) Uani 1 1 d . . . . .
N1 N 0.23725(16) 0.3660(2) 0.75891(9) 0.0132(3) Uani 1 1 d . . . . .
N8 N 0.50200(16) 0.7186(2) 0.62266(10) 0.0145(3) Uani 1 1 d . . . . .
C2 C 0.37313(19) 0.4065(2) 0.74275(11) 0.0123(4) Uani 1 1 d . . . . .
C3 C 0.48079(19) 0.5118(3) 0.81016(11) 0.0131(4) Uani 1 1 d . . . . .
H3 H 0.562794 0.557750 0.786414 0.016 Uiso 1 1 calc R U . . .
C4 C 0.4040(2) 0.6742(3) 0.84270(11) 0.0145(4) Uani 1 1 d . . . . .
C5 C 0.3656(2) 0.8346(3) 0.77677(12) 0.0158(4) Uani 1 1 d . . . . .
H5A H 0.307540 0.924689 0.800351 0.019 Uiso 1 1 calc R U . . .
H5AB H 0.459573 0.894990 0.775663 0.019 Uiso 1 1 calc R U . . .
C6 C 0.28088(19) 0.7986(3) 0.68198(11) 0.0151(4) Uani 1 1 d . . . . .
H6A H 0.248192 0.669481 0.676186 0.018 Uiso 1 1 calc R U . . .
H6AB H 0.191735 0.876584 0.667625 0.018 Uiso 1 1 calc R U . . .
C7 C 0.3728(2) 0.8368(3) 0.61727(12) 0.0162(4) Uani 1 1 d . . . . .
H7A H 0.307284 0.825856 0.558624 0.019 Uiso 1 1 calc R U . . .
H7AB H 0.407211 0.965170 0.624794 0.019 Uiso 1 1 calc R U . . .
C9 C 0.48686(19) 0.5524(3) 0.56978(11) 0.0153(4) Uani 1 1 d . . . . .
H9A H 0.563771 0.553698 0.537521 0.018 Uiso 1 1 calc R U . . .
H9AB H 0.389905 0.555279 0.527264 0.018 Uiso 1 1 calc R U . . .
C10 C 0.4994(2) 0.3730(3) 0.62045(11) 0.0143(4) Uani 1 1 d . . . . .
H10A H 0.499974 0.269165 0.581043 0.017 Uiso 1 1 calc R U . . .
H10B H 0.594065 0.371602 0.665067 0.017 Uiso 1 1 calc R U . . .
C11 C 0.37518(19) 0.3486(2) 0.66253(11) 0.0128(4) Uani 1 1 d . . . . .
C12 C 0.23098(19) 0.2754(3) 0.62362(11) 0.0135(4) Uani 1 1 d . . . . .
C13 C 0.1659(2) 0.2020(3) 0.54223(11) 0.0158(4) Uani 1 1 d . . . . .
H13 H 0.220344 0.193010 0.500033 0.019 Uiso 1 1 calc R U . . .
C14 C 0.0211(2) 0.1431(3) 0.52432(12) 0.0190(4) Uani 1 1 d . . . . .
H14 H -0.023445 0.091408 0.469724 0.023 Uiso 1 1 calc R U . . .
C15 C -0.0607(2) 0.1588(3) 0.58594(13) 0.0197(4) Uani 1 1 d . . . . .
H15 H -0.160051 0.118052 0.571895 0.024 Uiso 1 1 calc R U . . .
C16 C -0.0004(2) 0.2320(3) 0.66676(12) 0.0167(4) Uani 1 1 d . . . . .
H16 H -0.056700 0.243071 0.707977 0.020 Uiso 1 1 calc R U . . .
C17 C 0.14671(19) 0.2890(3) 0.68507(11) 0.0137(4) Uani 1 1 d . . . . .
C18 C 0.19489(19) 0.4525(3) 0.82748(12) 0.0146(4) Uani 1 1 d . . . . .
C19 C 0.2676(2) 0.6001(3) 0.86498(12) 0.0160(4) Uani 1 1 d . . . . .
H19 H 0.231972 0.661523 0.907703 0.019 Uiso 1 1 calc R U . . .
C20 C 0.5071(2) 0.7525(3) 0.92621(12) 0.0193(4) Uani 1 1 d . . . . .
H20A H 0.465242 0.869453 0.940080 0.023 Uiso 1 1 calc R U . . .
H20B H 0.508210 0.666462 0.973899 0.023 Uiso 1 1 calc R U . . .
C21 C 0.6666(2) 0.7862(3) 0.92185(13) 0.0221(4) Uani 1 1 d . . . . .
H21A H 0.715483 0.668647 0.919317 0.033 Uiso 1 1 calc R U . . .
H21B H 0.719416 0.853527 0.973075 0.033 Uiso 1 1 calc R U . . .
H21C H 0.666561 0.857800 0.870361 0.033 Uiso 1 1 calc R U . . .
C22 C 0.6424(2) 0.2699(3) 0.86707(13) 0.0210(4) Uani 1 1 d . . . . .
H22A H 0.594320 0.191730 0.818547 0.031 Uiso 1 1 calc R U . . .
H22B H 0.679669 0.194099 0.918227 0.031 Uiso 1 1 calc R U . . .
H22C H 0.724515 0.335371 0.853222 0.031 Uiso 1 1 calc R U . . .
C23 C 0.0856(2) 0.3588(3) 0.86620(11) 0.0161(4) Uani 1 1 d . . . . .
C24 C 0.0039(2) 0.0692(3) 0.90074(15) 0.0273(5) Uani 1 1 d . . . . .
H24A H -0.095611 0.067463 0.862341 0.041 Uiso 1 1 calc R U . . .
H24B H 0.000648 0.122973 0.956029 0.041 Uiso 1 1 calc R U . . .
H24C H 0.041713 -0.056113 0.909838 0.041 Uiso 1 1 calc R U . . .
C25 C 0.6372(2) 0.7855(3) 0.66281(11) 0.0156(4) Uani 1 1 d . . . . .
C26 C 0.8914(2) 0.7172(3) 0.70466(14) 0.0230(4) Uani 1 1 d . . . . .
H26A H 0.962923 0.631153 0.691723 0.035 Uiso 1 1 calc R U . . .
H26B H 0.898324 0.715233 0.766476 0.035 Uiso 1 1 calc R U . . .
H26C H 0.912640 0.840773 0.687508 0.035 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
O1 C23 1.337(3) . ?
O1 C24 1.449(2) . ?
O2 C23 1.206(2) . ?
O3 C22 1.420(2) . ?
O3 C3 1.432(2) . ?
O4 C25 1.215(3) . ?
O5 C25 1.356(2) . ?
O5 C26 1.443(2) . ?
N1 C17 1.392(2) . ?
N1 C2 1.396(2) . ?
N1 C18 1.413(2) . ?
N8 C25 1.360(2) . ?
N8 C9 1.470(2) . ?
N8 C7 1.473(2) . ?
C2 C11 1.363(3) . ?
C2 C3 1.494(3) . ?
C3 C4 1.548(3) . ?
C3 H3 1.0000 . ?
C4 C19 1.514(3) . ?
C4 C20 1.552(2) . ?
C4 C5 1.561(3) . ?
C5 C6 1.553(3) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.537(2) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C9 C10 1.533(3) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C11 1.500(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.442(3) . ?
C12 C13 1.403(3) . ?
C12 C17 1.417(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.403(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.400(3) . ?
C16 H16 0.9500 . ?
C18 C19 1.336(3) . ?
C18 C23 1.494(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.536(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C23 O1 C24 116.23(16) . . ?
C22 O3 C3 111.57(14) . . ?
C25 O5 C26 114.95(16) . . ?
C17 N1 C2 108.38(14) . . ?
C17 N1 C18 127.99(15) . . ?
C2 N1 C18 120.10(15) . . ?
C25 N8 C9 120.91(15) . . ?
C25 N8 C7 118.12(16) . . ?
C9 N8 C7 119.60(15) . . ?
C11 C2 N1 110.08(16) . . ?
C11 C2 C3 132.67(17) . . ?
N1 C2 C3 117.08(15) . . ?
O3 C3 C2 110.07(15) . . ?
O3 C3 C4 106.33(14) . . ?
C2 C3 C4 110.74(15) . . ?
O3 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C19 C4 C3 107.40(16) . . ?
C19 C4 C20 107.79(15) . . ?
C3 C4 C20 109.56(15) . . ?
C19 C4 C5 111.50(15) . . ?
C3 C4 C5 113.20(14) . . ?
C20 C4 C5 107.26(16) . . ?
C6 C5 C4 120.82(16) . . ?
C6 C5 H5A 107.1 . . ?
C4 C5 H5A 107.1 . . ?
C6 C5 H5AB 107.1 . . ?
C4 C5 H5AB 107.1 . . ?
H5A C5 H5AB 106.8 . . ?
C7 C6 C5 113.50(15) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6AB 108.9 . . ?
C5 C6 H6AB 108.9 . . ?
H6A C6 H6AB 107.7 . . ?
N8 C7 C6 116.63(15) . . ?
N8 C7 H7A 108.1 . . ?
C6 C7 H7A 108.1 . . ?
N8 C7 H7AB 108.1 . . ?
C6 C7 H7AB 108.1 . . ?
H7A C7 H7AB 107.3 . . ?
N8 C9 C10 114.65(14) . . ?
N8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N8 C9 H9AB 108.6 . . ?
C10 C9 H9AB 108.6 . . ?
H9A C9 H9AB 107.6 . . ?
C11 C10 C9 112.21(15) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C2 C11 C12 106.82(16) . . ?
C2 C11 C10 126.12(17) . . ?
C12 C11 C10 126.83(16) . . ?
C13 C12 C17 119.32(17) . . ?
C13 C12 C11 133.27(17) . . ?
C17 C12 C11 107.40(16) . . ?
C14 C13 C12 119.03(17) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.72(18) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 121.87(18) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 117.24(17) . . ?
C15 C16 H16 121.4 . . ?
C17 C16 H16 121.4 . . ?
N1 C17 C16 130.98(16) . . ?
N1 C17 C12 107.22(15) . . ?
C16 C17 C12 121.80(17) . . ?
C19 C18 N1 120.08(17) . . ?
C19 C18 C23 120.52(17) . . ?
N1 C18 C23 118.62(17) . . ?
C18 C19 C4 123.21(17) . . ?
C18 C19 H19 118.4 . . ?
C4 C19 H19 118.4 . . ?
C21 C20 C4 114.83(16) . . ?
C21 C20 H20A 108.6 . . ?
C4 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C4 C20 H20B 108.6 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 O1 125.32(18) . . ?
O2 C23 C18 124.18(19) . . ?
O1 C23 C18 110.40(16) . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 O5 123.23(17) . . ?
O4 C25 N8 125.94(17) . . ?
O5 C25 N8 110.83(17) . . ?
O5 C26 H26A 109.5 . . ?
O5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N1 C2 C11 -3.3(2) . . . . ?
C18 N1 C2 C11 -163.80(16) . . . . ?
C17 N1 C2 C3 172.59(15) . . . . ?
C18 N1 C2 C3 12.1(2) . . . . ?
C22 O3 C3 C2 74.62(18) . . . . ?
C22 O3 C3 C4 -165.39(15) . . . . ?
C11 C2 C3 O3 -113.1(2) . . . . ?
N1 C2 C3 O3 72.1(2) . . . . ?
C11 C2 C3 C4 129.6(2) . . . . ?
N1 C2 C3 C4 -45.2(2) . . . . ?
O3 C3 C4 C19 -69.66(17) . . . . ?
C2 C3 C4 C19 49.89(19) . . . . ?
O3 C3 C4 C20 47.16(19) . . . . ?
C2 C3 C4 C20 166.71(15) . . . . ?
O3 C3 C4 C5 166.83(14) . . . . ?
C2 C3 C4 C5 -73.62(19) . . . . ?
C19 C4 C5 C6 -70.3(2) . . . . ?
C3 C4 C5 C6 50.9(2) . . . . ?
C20 C4 C5 C6 171.89(15) . . . . ?
C4 C5 C6 C7 -113.99(19) . . . . ?
C25 N8 C7 C6 -100.9(2) . . . . ?
C9 N8 C7 C6 92.3(2) . . . . ?
C5 C6 C7 N8 65.0(2) . . . . ?
C25 N8 C9 C10 82.9(2) . . . . ?
C7 N8 C9 C10 -110.64(18) . . . . ?
N8 C9 C10 C11 65.55(19) . . . . ?
N1 C2 C11 C12 2.9(2) . . . . ?
C3 C2 C11 C12 -172.18(19) . . . . ?
N1 C2 C11 C10 177.71(17) . . . . ?
C3 C2 C11 C10 2.6(3) . . . . ?
C9 C10 C11 C2 -89.8(2) . . . . ?
C9 C10 C11 C12 84.0(2) . . . . ?
C2 C11 C12 C13 177.6(2) . . . . ?
C10 C11 C12 C13 2.9(3) . . . . ?
C2 C11 C12 C17 -1.4(2) . . . . ?
C10 C11 C12 C17 -176.16(17) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
C11 C12 C13 C14 -179.6(2) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C2 N1 C17 C16 -177.1(2) . . . . ?
C18 N1 C17 C16 -18.7(3) . . . . ?
C2 N1 C17 C12 2.4(2) . . . . ?
C18 N1 C17 C12 160.80(18) . . . . ?
C15 C16 C17 N1 -179.75(19) . . . . ?
C15 C16 C17 C12 0.8(3) . . . . ?
C13 C12 C17 N1 -179.81(17) . . . . ?
C11 C12 C17 N1 -0.6(2) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C11 C12 C17 C16 178.93(18) . . . . ?
C17 N1 C18 C19 -141.62(19) . . . . ?
C2 N1 C18 C19 14.6(3) . . . . ?
C17 N1 C18 C23 48.4(3) . . . . ?
C2 N1 C18 C23 -155.37(16) . . . . ?
N1 C18 C19 C4 -5.1(3) . . . . ?
C23 C18 C19 C4 164.70(17) . . . . ?
C3 C4 C19 C18 -27.5(2) . . . . ?
C20 C4 C19 C18 -145.43(18) . . . . ?
C5 C4 C19 C18 97.1(2) . . . . ?
C19 C4 C20 C21 164.29(17) . . . . ?
C3 C4 C20 C21 47.7(2) . . . . ?
C5 C4 C20 C21 -75.5(2) . . . . ?
C24 O1 C23 O2 1.2(3) . . . . ?
C24 O1 C23 C18 177.72(15) . . . . ?
C19 C18 C23 O2 38.5(3) . . . . ?
N1 C18 C23 O2 -151.54(18) . . . . ?
C19 C18 C23 O1 -138.05(18) . . . . ?
N1 C18 C23 O1 31.9(2) . . . . ?
C26 O5 C25 O4 4.1(3) . . . . ?
C26 O5 C25 N8 -175.27(15) . . . . ?
C9 N8 C25 O4 170.84(17) . . . . ?
C7 N8 C25 O4 4.2(3) . . . . ?
C9 N8 C25 O5 -9.8(2) . . . . ?
C7 N8 C25 O5 -176.44(15) . . . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.064




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_Y-20
_database_code_depnum_ccdc_archive 'CCDC 2338892'
loop_
_audit_author_name
_audit_author_address
'Khalil A. Abboud'
;Department of Chemistry, University of Florida
United States of America
;

_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H35 I N2 O6'
_chemical_formula_weight         646.50

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                   12.0831(6)
_cell_length_b                   9.8234(5)
_cell_length_c                   13.0300(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.9770(10)
_cell_angle_gamma                90
_cell_volume                     1434.24(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9687
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      32.93

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             660
_exptl_transmission_factor_min   0.5264
_exptl_transmission_factor_max   0.5659
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    1.162
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8514
_exptl_absorpt_correction_T_max  0.9539
_exptl_absorpt_process_details   
'Sheldrick, G. M., sadabs (2014). Acta Cryst. C71, 3--8.'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS microsource 3.0'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            45405
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.672
_diffrn_reflns_theta_max         33.356
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             9830
_reflns_number_gt                9642
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_max     0.839
_reflns_Friedel_fraction_full    0.985

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'

_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.

The hydroxyl and amino protons were obtained from a difference Fourier map and
 refined freely.  The molecules also exhibit a network of hydrogen bonding
 involving bot of the protons.  The reported structure and stereochemistry
 reported here are supported by the value of the Flack x parameter of -0.017(2).
  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0226P)²+0.3774P] 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 4234 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.017(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9830
_refine_ls_number_parameters     362
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0198
_refine_ls_wR_factor_ref         0.0481
_refine_ls_wR_factor_gt          0.0477
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.21770(2) 0.20866(2) 0.90903(2) 0.03513(4) Uani 1 1 d . . . . .
O1 O 0.62115(15) 0.85903(16) 0.70757(14) 0.0272(3) Uani 1 1 d . . . . .
H1A H 0.639(3) 0.928(4) 0.727(3) 0.043(8) Uiso 1 1 d . . . . .
O2 O 0.65582(12) 0.53185(14) 0.82160(10) 0.0234(2) Uani 1 1 d . . . . .
O3 O 0.66596(12) 0.56719(14) 0.65514(11) 0.0232(2) Uani 1 1 d . . . . .
O1' O 0.25407(12) 0.62641(15) 0.25751(12) 0.0258(3) Uani 1 1 d . . . . .
O2' O 0.06550(12) 0.55587(16) 0.22276(11) 0.0271(3) Uani 1 1 d . . . . .
O1" O 0.38265(11) 0.35965(12) 0.65606(10) 0.0180(2) Uani 1 1 d . . . . .
N1 N 0.20355(13) 0.26307(15) 0.44211(12) 0.0190(2) Uani 1 1 d . . . . .
H1B H 0.266(3) 0.224(4) 0.445(2) 0.037(7) Uiso 1 1 d . . . . .
N4 N 0.15480(12) 0.69165(16) 0.36832(11) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.19911(14) 0.38624(16) 0.49224(13) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.30690(14) 0.45293(15) 0.57540(12) 0.0155(3) Uani 1 1 d . . . . .
H3A H 0.278166 0.522233 0.615923 0.019 Uiso 1 1 calc R U . . .
C5 C 0.04525(14) 0.68514(18) 0.39226(14) 0.0228(3) Uani 1 1 d . . . . .
H5A H -0.023388 0.670330 0.321914 0.027 Uiso 1 1 calc R U . . .
H5B H 0.033529 0.774201 0.422289 0.027 Uiso 1 1 calc R U . . .
C6 C 0.04460(15) 0.57251(18) 0.47484(14) 0.0203(3) Uani 1 1 d . . . . .
H6A H 0.097271 0.600616 0.550325 0.024 Uiso 1 1 calc R U . . .
H6B H -0.037314 0.563382 0.474054 0.024 Uiso 1 1 calc R U . . .
C7 C 0.08500(14) 0.43686(17) 0.44995(13) 0.0178(3) Uani 1 1 d . . . . .
C8 C 0.01479(15) 0.34167(17) 0.36792(14) 0.0191(3) Uani 1 1 d . . . . .
C9 C -0.10496(16) 0.3389(2) 0.29580(16) 0.0254(3) Uani 1 1 d . . . . .
H9A H -0.157666 0.410538 0.296004 0.030 Uiso 1 1 calc R U . . .
C1' C 0.16500(15) 0.62513(18) 0.28162(14) 0.0209(3) Uani 1 1 d . . . . .
C2' C 0.0752(2) 0.4648(3) 0.14049(18) 0.0365(5) Uani 1 1 d . . . . .
H2'A H 0.001523 0.411563 0.108728 0.055 Uiso 1 1 calc R U . . .
H2'B H 0.142793 0.403109 0.174651 0.055 Uiso 1 1 calc R U . . .
H2'C H 0.087768 0.517341 0.081874 0.055 Uiso 1 1 calc R U . . .
C1" C 0.33080(16) 0.31710(19) 0.73183(14) 0.0222(3) Uani 1 1 d . . . . .
H1"A H 0.261627 0.257250 0.693734 0.027 Uiso 1 1 calc R U . . .
H1"B H 0.301933 0.397457 0.760366 0.027 Uiso 1 1 calc R U . . .
C2" C 0.42161(14) 0.24126(15) 0.82672(13) 0.0181(3) Uani 1 1 d . . . . .
C3" C 0.39080(14) 0.18269(17) 0.90969(13) 0.0211(3) Uani 1 1 d . . . . .
C4" C 0.47075(17) 0.1048(2) 0.99417(15) 0.0253(3) Uani 1 1 d . . . . .
H4"A H 0.446823 0.064236 1.048761 0.030 Uiso 1 1 calc R U . . .
C5" C 0.58598(17) 0.0873(2) 0.99750(15) 0.0271(4) Uani 1 1 d . . . . .
H5"A H 0.641290 0.033339 1.054086 0.032 Uiso 1 1 calc R U . . .
C6" C 0.62055(16) 0.1487(2) 0.91809(15) 0.0252(3) Uani 1 1 d . . . . .
H6"A H 0.700177 0.138913 0.921795 0.030 Uiso 1 1 calc R U . . .
C7" C 0.53896(14) 0.22427(19) 0.83339(13) 0.0214(3) Uani 1 1 d . . . . .
H7"A H 0.563248 0.265076 0.779111 0.026 Uiso 1 1 calc R U . . .
C10 C -0.14515(16) 0.2298(2) 0.22424(16) 0.0307(4) Uani 1 1 d . . . . .
H10A H -0.226224 0.226977 0.174874 0.037 Uiso 1 1 calc R U . . .
C11 C -0.06819(18) 0.1236(2) 0.22343(17) 0.0305(4) Uani 1 1 d . . . . .
H11A H -0.098361 0.049553 0.173920 0.037 Uiso 1 1 calc R U . . .
C12 C 0.05118(17) 0.12412(19) 0.29331(16) 0.0242(3) Uani 1 1 d . . . . .
H12A H 0.103317 0.052092 0.292502 0.029 Uiso 1 1 calc R U . . .
C13 C 0.09140(14) 0.23468(16) 0.36471(13) 0.0190(3) Uani 1 1 d . . . . .
C14 C 0.38609(14) 0.52716(15) 0.52449(12) 0.0158(3) Uani 1 1 d . . . . .
H14A H 0.342159 0.534626 0.443562 0.019 Uiso 1 1 calc R U . . .
H14B H 0.458422 0.471775 0.536938 0.019 Uiso 1 1 calc R U . . .
C15 C 0.42455(14) 0.67090(15) 0.57231(12) 0.0157(3) Uani 1 1 d . . . . .
H15A H 0.475210 0.710013 0.534004 0.019 Uiso 1 1 calc R U . . .
C16 C 0.50224(14) 0.66350(15) 0.69690(13) 0.0157(3) Uani 1 1 d . . . . .
H16A H 0.454803 0.616368 0.734878 0.019 Uiso 1 1 calc R U . . .
C17 C 0.53954(15) 0.80334(17) 0.75171(14) 0.0200(3) Uani 1 1 d . . . . .
H17A H 0.580981 0.791054 0.833426 0.024 Uiso 1 1 calc R U . . .
C18 C 0.43032(17) 0.89233(18) 0.72894(15) 0.0236(3) Uani 1 1 d . . . . .
H18A H 0.455614 0.983477 0.761763 0.028 Uiso 1 1 calc R U . . .
H18B H 0.378646 0.851753 0.764511 0.028 Uiso 1 1 calc R U . . .
C19 C 0.35957(16) 0.90710(17) 0.60522(16) 0.0227(3) Uani 1 1 d . . . . .
H19A H 0.410066 0.951448 0.570121 0.027 Uiso 1 1 calc R U . . .
H19B H 0.289338 0.966031 0.593152 0.027 Uiso 1 1 calc R U . . .
C20 C 0.31769(15) 0.76816(16) 0.55085(13) 0.0179(3) Uani 1 1 d . . . . .
H20A H 0.263236 0.727189 0.584318 0.021 Uiso 1 1 calc R U . . .
C21 C 0.24565(17) 0.79283(18) 0.42713(15) 0.0235(3) Uani 1 1 d . . . . .
H21A H 0.205708 0.882339 0.419543 0.028 Uiso 1 1 calc R U . . .
H21B H 0.302668 0.799479 0.389093 0.028 Uiso 1 1 calc R U . . .
C22 C 0.61510(17) 0.58198(17) 0.71841(15) 0.0175(3) Uani 1 1 d . . . . .
C23 C 0.76890(18) 0.4614(2) 0.85741(16) 0.0290(4) Uani 1 1 d . . . . .
H23A H 0.783301 0.416452 0.928380 0.043 Uiso 1 1 calc R U . . .
H23B H 0.832935 0.526991 0.866120 0.043 Uiso 1 1 calc R U . . .
H23C H 0.767188 0.393133 0.802026 0.043 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 C3" 2.1039(17) . ?
O1 C17 1.424(2) . ?
O1 H1A 0.73(4) . ?
O2 C22 1.341(2) . ?
O2 C23 1.444(2) . ?
O3 C22 1.207(2) . ?
O1' C1' 1.229(2) . ?
O2' C1' 1.344(2) . ?
O2' C2' 1.434(3) . ?
O1" C1" 1.416(2) . ?
O1" C3 1.4361(18) . ?
N1 C13 1.381(2) . ?
N1 C2 1.386(2) . ?
N1 H1B 0.83(3) . ?
N4 C1' 1.350(2) . ?
N4 C21 1.467(2) . ?
N4 C5 1.471(2) . ?
C2 C7 1.372(2) . ?
C2 C3 1.498(2) . ?
C3 C14 1.537(2) . ?
C3 H3A 1.0000 . ?
C5 C6 1.545(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.496(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.435(2) . ?
C8 C9 1.400(2) . ?
C8 C13 1.411(2) . ?
C9 C10 1.383(3) . ?
C9 H9A 0.9500 . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C1" C2" 1.507(2) . ?
C1" H1"A 0.9900 . ?
C1" H1"B 0.9900 . ?
C2" C3" 1.393(2) . ?
C2" C7" 1.398(2) . ?
C3" C4" 1.391(2) . ?
C4" C5" 1.387(3) . ?
C4" H4"A 0.9500 . ?
C5" C6" 1.390(3) . ?
C5" H5"A 0.9500 . ?
C6" C7" 1.388(2) . ?
C6" H6"A 0.9500 . ?
C7" H7"A 0.9500 . ?
C10 C11 1.400(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.394(2) . ?
C12 H12A 0.9500 . ?
C14 C15 1.543(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.543(2) . ?
C15 C20 1.545(2) . ?
C15 H15A 1.0000 . ?
C16 C22 1.514(2) . ?
C16 C17 1.536(2) . ?
C16 H16A 1.0000 . ?
C17 C18 1.517(2) . ?
C17 H17A 1.0000 . ?
C18 C19 1.523(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.534(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.538(2) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C17 O1 H1A 112(3) . . ?
C22 O2 C23 116.60(15) . . ?
C1' O2' C2' 115.89(16) . . ?
C1" O1" C3 111.81(12) . . ?
C13 N1 C2 108.66(14) . . ?
C13 N1 H1B 124(2) . . ?
C2 N1 H1B 125(2) . . ?
C1' N4 C21 118.71(15) . . ?
C1' N4 C5 121.85(14) . . ?
C21 N4 C5 118.41(14) . . ?
C7 C2 N1 109.72(14) . . ?
C7 C2 C3 127.08(15) . . ?
N1 C2 C3 123.13(14) . . ?
O1" C3 C2 113.20(12) . . ?
O1" C3 C14 106.82(12) . . ?
C2 C3 C14 114.11(12) . . ?
O1" C3 H3A 107.5 . . ?
C2 C3 H3A 107.5 . . ?
C14 C3 H3A 107.5 . . ?
N4 C5 C6 114.73(13) . . ?
N4 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
N4 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C5 113.55(14) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C2 C7 C8 106.75(14) . . ?
C2 C7 C6 126.59(15) . . ?
C8 C7 C6 126.32(15) . . ?
C9 C8 C13 119.35(16) . . ?
C9 C8 C7 133.43(16) . . ?
C13 C8 C7 107.21(14) . . ?
C10 C9 C8 118.79(17) . . ?
C10 C9 H9A 120.6 . . ?
C8 C9 H9A 120.6 . . ?
O1' C1' O2' 122.78(17) . . ?
O1' C1' N4 124.88(16) . . ?
O2' C1' N4 112.34(15) . . ?
O2' C2' H2'A 109.5 . . ?
O2' C2' H2'B 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
O2' C2' H2'C 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
O1" C1" C2" 109.97(14) . . ?
O1" C1" H1"A 109.7 . . ?
C2" C1" H1"A 109.7 . . ?
O1" C1" H1"B 109.7 . . ?
C2" C1" H1"B 109.7 . . ?
H1"A C1" H1"B 108.2 . . ?
C3" C2" C7" 117.52(14) . . ?
C3" C2" C1" 121.12(15) . . ?
C7" C2" C1" 121.34(14) . . ?
C4" C3" C2" 122.23(16) . . ?
C4" C3" I1 117.71(12) . . ?
C2" C3" I1 120.06(12) . . ?
C5" C4" C3" 118.99(16) . . ?
C5" C4" H4"A 120.5 . . ?
C3" C4" H4"A 120.5 . . ?
C4" C5" C6" 120.03(17) . . ?
C4" C5" H5"A 120.0 . . ?
C6" C5" H5"A 120.0 . . ?
C7" C6" C5" 120.13(17) . . ?
C7" C6" H6"A 119.9 . . ?
C5" C6" H6"A 119.9 . . ?
C6" C7" C2" 121.03(15) . . ?
C6" C7" H7"A 119.5 . . ?
C2" C7" H7"A 119.5 . . ?
C9 C10 C11 121.02(16) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C12 C11 C10 121.50(17) . . ?
C12 C11 H11A 119.3 . . ?
C10 C11 H11A 119.3 . . ?
C11 C12 C13 117.24(17) . . ?
C11 C12 H12A 121.4 . . ?
C13 C12 H12A 121.4 . . ?
N1 C13 C12 130.26(16) . . ?
N1 C13 C8 107.65(14) . . ?
C12 C13 C8 122.09(15) . . ?
C3 C14 C15 113.70(12) . . ?
C3 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C3 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 110.75(12) . . ?
C16 C15 C20 110.95(12) . . ?
C14 C15 C20 112.81(12) . . ?
C16 C15 H15A 107.3 . . ?
C14 C15 H15A 107.3 . . ?
C20 C15 H15A 107.3 . . ?
C22 C16 C17 107.43(13) . . ?
C22 C16 C15 111.76(13) . . ?
C17 C16 C15 113.84(13) . . ?
C22 C16 H16A 107.9 . . ?
C17 C16 H16A 107.9 . . ?
C15 C16 H16A 107.9 . . ?
O1 C17 C18 112.52(15) . . ?
O1 C17 C16 106.44(13) . . ?
C18 C17 C16 110.00(13) . . ?
O1 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C17 C18 C19 111.38(14) . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
C19 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 C20 111.20(14) . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C21 107.66(13) . . ?
C19 C20 C15 110.96(13) . . ?
C21 C20 C15 113.20(14) . . ?
C19 C20 H20A 108.3 . . ?
C21 C20 H20A 108.3 . . ?
C15 C20 H20A 108.3 . . ?
N4 C21 C20 117.41(14) . . ?
N4 C21 H21A 107.9 . . ?
C20 C21 H21A 107.9 . . ?
N4 C21 H21B 107.9 . . ?
C20 C21 H21B 107.9 . . ?
H21A C21 H21B 107.2 . . ?
O3 C22 O2 123.44(17) . . ?
O3 C22 C16 126.19(16) . . ?
O2 C22 C16 110.30(15) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
_geom_hbond_publ_flag
O1 H1A O1' 0.73(4) 2.30(4) 2.978(2) 155(3) 2_656 yes
N1 H1B O3 0.83(3) 2.36(3) 3.048(2) 141(2) 2_646 yes
C5 H5A I1 0.99 3.07 4.0279(16) 163.3 2_556 yes

_refine_diff_density_max         0.734
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.045




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_Y-24
_database_code_depnum_ccdc_archive 'CCDC 2338909'
loop_
_audit_author_name
_audit_author_address
'Khalil A. Abboud'
;Department of Chemistry, University of Florida
United States of America
;

_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H36 N2 O5 S'
_chemical_formula_weight         536.67

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.7448(3)
_cell_length_b                   14.0034(5)
_cell_length_c                   19.6580(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2682.54(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      31.94

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   0.4909
_exptl_transmission_factor_max   0.5606
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_process_details   
'Sheldrick, G. M., sadabs (2014). Acta Cryst. C71, 3--8.'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro source 3.0'
_diffrn_measurement_device_type  'D8 Venture with PHOTON III'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            64890
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.072
_diffrn_reflns_theta_max         33.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9474
_reflns_number_gt                8697
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.884
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'

_refine_special_details          
;
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and   
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).
Methyl ones were allowed to rotate around the corresponding C---C.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0443P)²+0.2927P] 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 3555 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.013(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9474
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
S1 S 0.59804(3) 0.56239(2) 0.56726(2) 0.01481(7) Uani 1 1 d . . . . .
O1 O 0.05713(12) 0.71653(8) 0.62183(6) 0.0194(2) Uani 1 1 d . . . . .
O1' O 0.31691(11) 0.68967(8) 0.32433(6) 0.0186(2) Uani 1 1 d . . . . .
O2 O 0.36180(11) 0.66187(7) 0.69629(5) 0.0175(2) Uani 1 1 d . . . . .
O2' O 0.39501(11) 0.55637(7) 0.27201(5) 0.0181(2) Uani 1 1 d . . . . .
O3 O 0.36084(11) 0.77312(7) 0.61373(5) 0.0169(2) Uani 1 1 d . . . . .
N1 N 0.66920(12) 0.55452(9) 0.40965(6) 0.0137(2) Uani 1 1 d . . . . .
H1 H 0.7068(19) 0.6053(14) 0.4262(10) 0.015(4) Uiso 1 1 d . . . . .
N4 N 0.25054(13) 0.54094(9) 0.36042(6) 0.0157(2) Uani 1 1 d . . . . .
C1" C 0.66750(14) 0.44237(11) 0.57376(8) 0.0181(3) Uani 1 1 d . . . . .
H1"A H 0.725531 0.430190 0.533341 0.022 Uiso 1 1 calc R U . . .
H1"B H 0.727686 0.439427 0.614274 0.022 Uiso 1 1 calc R U . . .
C1' C 0.31964(15) 0.60227(10) 0.31949(7) 0.0155(2) Uani 1 1 d . . . . .
C2 C 0.54896(14) 0.51389(9) 0.43335(7) 0.0130(2) Uani 1 1 d . . . . .
C2" C 0.56237(15) 0.36327(11) 0.57903(8) 0.0187(3) Uani 1 1 d . . . . .
C2' C 0.49419(16) 0.61441(11) 0.23699(8) 0.0197(3) Uani 1 1 d . . . . .
H2'A H 0.560177 0.573148 0.213502 0.030 Uiso 1 1 calc R U . . .
H2'B H 0.542756 0.654651 0.269911 0.030 Uiso 1 1 calc R U . . .
H2'C H 0.447236 0.654961 0.203690 0.030 Uiso 1 1 calc R U . . .
C3 C 0.47835(14) 0.54716(10) 0.49651(6) 0.0129(2) Uani 1 1 d . . . . .
H3 H 0.411597 0.496304 0.509945 0.015 Uiso 1 1 calc R U . . .
C3" C 0.45335(16) 0.36776(12) 0.62499(8) 0.0228(3) Uani 1 1 d . . . . .
H3" H 0.442455 0.422518 0.653007 0.027 Uiso 1 1 calc R U . . .
C4" C 0.36049(17) 0.29255(14) 0.63005(10) 0.0289(4) Uani 1 1 d . . . . .
H4" H 0.286652 0.296282 0.661488 0.035 Uiso 1 1 calc R U . . .
C5 C 0.26046(15) 0.43704(11) 0.35143(7) 0.0169(2) Uani 1 1 d . . . . .
H5A H 0.276934 0.423291 0.302713 0.020 Uiso 1 1 calc R U . . .
H5AB H 0.171350 0.407972 0.363925 0.020 Uiso 1 1 calc R U . . .
C5" C 0.37517(18) 0.21221(13) 0.58945(10) 0.0314(4) Uani 1 1 d . . . . .
H5" H 0.312408 0.160596 0.593413 0.038 Uiso 1 1 calc R U . . .
C6 C 0.37493(14) 0.38893(10) 0.39384(7) 0.0159(3) Uani 1 1 d . . . . .
H6A H 0.345090 0.385244 0.441911 0.019 Uiso 1 1 calc R U . . .
H6AB H 0.388473 0.322863 0.377228 0.019 Uiso 1 1 calc R U . . .
C6" C 0.4816(2) 0.20779(13) 0.54324(11) 0.0316(4) Uani 1 1 d . . . . .
H6" H 0.491407 0.153216 0.514950 0.038 Uiso 1 1 calc R U . . .
C7 C 0.50909(14) 0.44129(10) 0.39033(7) 0.0138(2) Uani 1 1 d . . . . .
C7" C 0.57519(17) 0.28309(11) 0.53781(9) 0.0244(3) Uani 1 1 d . . . . .
H7" H 0.647959 0.279449 0.505751 0.029 Uiso 1 1 calc R U . . .
C8 C 0.60991(14) 0.43666(10) 0.33730(7) 0.0138(2) Uani 1 1 d . . . . .
C9 C 0.62650(15) 0.37880(10) 0.27943(7) 0.0156(3) Uani 1 1 d . . . . .
H9 H 0.561274 0.330553 0.269008 0.019 Uiso 1 1 calc R U . . .
C10 C 0.73948(16) 0.39323(11) 0.23781(7) 0.0179(3) Uani 1 1 d . . . . .
H10 H 0.752416 0.353689 0.199070 0.021 Uiso 1 1 calc R U . . .
C11 C 0.83512(16) 0.46559(11) 0.25219(7) 0.0177(3) Uani 1 1 d . . . . .
H11 H 0.911464 0.474278 0.222786 0.021 Uiso 1 1 calc R U . . .
C12 C 0.82047(15) 0.52451(10) 0.30830(7) 0.0152(2) Uani 1 1 d . . . . .
H12 H 0.884816 0.573752 0.317668 0.018 Uiso 1 1 calc R U . . .
C13 C 0.70756(14) 0.50884(10) 0.35061(7) 0.0134(2) Uani 1 1 d . . . . .
C14 C 0.39636(14) 0.64128(9) 0.48853(7) 0.0134(2) Uani 1 1 d . . . . .
H14A H 0.447346 0.693161 0.511590 0.016 Uiso 1 1 calc R U . . .
H14B H 0.391277 0.657491 0.439578 0.016 Uiso 1 1 calc R U . . .
C15 C 0.24964(14) 0.63801(9) 0.51743(7) 0.0126(2) Uani 1 1 d . . . . .
H15 H 0.208305 0.702516 0.509936 0.015 Uiso 1 1 calc R U . . .
C16 C 0.24925(14) 0.61987(9) 0.59489(7) 0.0128(2) Uani 1 1 d . . . . .
H16 H 0.291689 0.555986 0.603505 0.015 Uiso 1 1 calc R U . . .
C17 C 0.10382(15) 0.61996(10) 0.62606(7) 0.0153(2) Uani 1 1 d . . . . .
H17 H 0.109294 0.600412 0.674913 0.018 Uiso 1 1 calc R U . . .
C18 C 0.01043(14) 0.55139(11) 0.58799(7) 0.0169(3) Uani 1 1 d . . . . .
H18A H -0.084259 0.557743 0.605667 0.020 Uiso 1 1 calc R U . . .
H18B H 0.041173 0.485074 0.596476 0.020 Uiso 1 1 calc R U . . .
C19 C 0.01014(14) 0.57019(10) 0.51161(7) 0.0161(2) Uani 1 1 d . . . . .
H19A H -0.028779 0.634298 0.502758 0.019 Uiso 1 1 calc R U . . .
H19B H -0.049182 0.522527 0.488825 0.019 Uiso 1 1 calc R U . . .
C20 C 0.15546(14) 0.56474(10) 0.48150(7) 0.0142(2) Uani 1 1 d . . . . .
H20 H 0.192763 0.499265 0.489905 0.017 Uiso 1 1 calc R U . . .
C21 C 0.14139(15) 0.57929(11) 0.40419(7) 0.0173(3) Uani 1 1 d . . . . .
H21A H 0.053534 0.550223 0.389679 0.021 Uiso 1 1 calc R U . . .
H21B H 0.134491 0.648757 0.395474 0.021 Uiso 1 1 calc R U . . .
C22 C 0.33073(14) 0.69429(10) 0.63368(7) 0.0136(2) Uani 1 1 d . . . . .
C23 C 0.43234(18) 0.72877(11) 0.73991(8) 0.0218(3) Uani 1 1 d . . . . .
H23A H 0.513685 0.753375 0.716413 0.033 Uiso 1 1 calc R U . . .
H23B H 0.460415 0.696457 0.781881 0.033 Uiso 1 1 calc R U . . .
H23C H 0.370794 0.781866 0.751026 0.033 Uiso 1 1 calc R U . . .
H1A H -0.014(3) 0.7202(19) 0.6382(15) 0.048(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
S1 C1" 1.8164(15) . ?
S1 C3 1.8277(13) . ?
O1 C17 1.4292(18) . ?
O1 H1A 0.77(3) . ?
O1' C1' 1.2279(17) . ?
O2 C22 1.3463(17) . ?
O2 C23 1.4440(18) . ?
O2' C1' 1.3505(17) . ?
O2' C2' 1.4383(18) . ?
O3 C22 1.2077(17) . ?
N1 C13 1.3769(17) . ?
N1 C2 1.3834(18) . ?
N1 H1 0.86(2) . ?
N4 C1' 1.3558(19) . ?
N4 C5 1.4688(19) . ?
N4 C21 1.4697(19) . ?
C1" C2" 1.512(2) . ?
C1" H1"A 0.9900 . ?
C1" H1"B 0.9900 . ?
C2 C7 1.3783(18) . ?
C2 C3 1.4939(19) . ?
C2" C7" 1.390(2) . ?
C2" C3" 1.396(2) . ?
C2' H2'A 0.9800 . ?
C2' H2'B 0.9800 . ?
C2' H2'C 0.9800 . ?
C3 C14 1.5493(19) . ?
C3 H3 1.0000 . ?
C3" C4" 1.392(2) . ?
C3" H3" 0.9500 . ?
C4" C5" 1.387(3) . ?
C4" H4" 0.9500 . ?
C5 C6 1.547(2) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C5" C6" 1.380(3) . ?
C5" H5" 0.9500 . ?
C6 C7 1.5005(19) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C6" C7" 1.398(2) . ?
C6" H6" 0.9500 . ?
C7 C8 1.4341(18) . ?
C7" H7" 0.9500 . ?
C8 C9 1.4058(18) . ?
C8 C13 1.4126(19) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(2) . ?
C12 H12 0.9500 . ?
C14 C15 1.5391(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5438(19) . ?
C15 C20 1.5472(19) . ?
C15 H15 1.0000 . ?
C16 C22 1.5160(19) . ?
C16 C17 1.5440(19) . ?
C16 H16 1.0000 . ?
C17 C18 1.520(2) . ?
C17 H17 1.0000 . ?
C18 C19 1.524(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5367(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.540(2) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1" S1 C3 100.57(6) . . ?
C17 O1 H1A 109(2) . . ?
C22 O2 C23 115.54(11) . . ?
C1' O2' C2' 115.30(12) . . ?
C13 N1 C2 108.83(11) . . ?
C13 N1 H1 125.8(13) . . ?
C2 N1 H1 124.8(13) . . ?
C1' N4 C5 121.56(12) . . ?
C1' N4 C21 118.38(12) . . ?
C5 N4 C21 118.69(12) . . ?
C2" C1" S1 115.47(10) . . ?
C2" C1" H1"A 108.4 . . ?
S1 C1" H1"A 108.4 . . ?
C2" C1" H1"B 108.4 . . ?
S1 C1" H1"B 108.4 . . ?
H1"A C1" H1"B 107.5 . . ?
O1' C1' O2' 122.66(14) . . ?
O1' C1' N4 125.08(14) . . ?
O2' C1' N4 112.26(12) . . ?
C7 C2 N1 109.60(12) . . ?
C7 C2 C3 127.59(12) . . ?
N1 C2 C3 122.81(12) . . ?
C7" C2" C3" 118.82(15) . . ?
C7" C2" C1" 119.39(14) . . ?
C3" C2" C1" 121.79(14) . . ?
O2' C2' H2'A 109.5 . . ?
O2' C2' H2'B 109.5 . . ?
H2'A C2' H2'B 109.5 . . ?
O2' C2' H2'C 109.5 . . ?
H2'A C2' H2'C 109.5 . . ?
H2'B C2' H2'C 109.5 . . ?
C2 C3 C14 114.76(11) . . ?
C2 C3 S1 112.02(9) . . ?
C14 C3 S1 107.87(9) . . ?
C2 C3 H3 107.3 . . ?
C14 C3 H3 107.3 . . ?
S1 C3 H3 107.3 . . ?
C4" C3" C2" 120.44(17) . . ?
C4" C3" H3" 119.8 . . ?
C2" C3" H3" 119.8 . . ?
C5" C4" C3" 120.38(17) . . ?
C5" C4" H4" 119.8 . . ?
C3" C4" H4" 119.8 . . ?
N4 C5 C6 114.46(11) . . ?
N4 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
N4 C5 H5AB 108.6 . . ?
C6 C5 H5AB 108.6 . . ?
H5A C5 H5AB 107.6 . . ?
C6" C5" C4" 119.51(16) . . ?
C6" C5" H5" 120.2 . . ?
C4" C5" H5" 120.2 . . ?
C7 C6 C5 113.00(11) . . ?
C7 C6 H6A 109.0 . . ?
C5 C6 H6A 109.0 . . ?
C7 C6 H6AB 109.0 . . ?
C5 C6 H6AB 109.0 . . ?
H6A C6 H6AB 107.8 . . ?
C5" C6" C7" 120.44(18) . . ?
C5" C6" H6" 119.8 . . ?
C7" C6" H6" 119.8 . . ?
C2 C7 C8 106.63(12) . . ?
C2 C7 C6 125.30(12) . . ?
C8 C7 C6 127.47(12) . . ?
C2" C7" C6" 120.39(16) . . ?
C2" C7" H7" 119.8 . . ?
C6" C7" H7" 119.8 . . ?
C9 C8 C13 119.00(13) . . ?
C9 C8 C7 133.87(13) . . ?
C13 C8 C7 107.13(11) . . ?
C10 C9 C8 119.00(13) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.86(13) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 121.43(14) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 117.51(13) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
N1 C13 C12 129.99(13) . . ?
N1 C13 C8 107.80(12) . . ?
C12 C13 C8 122.20(12) . . ?
C15 C14 C3 114.61(11) . . ?
C15 C14 H14A 108.6 . . ?
C3 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C3 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 111.79(11) . . ?
C14 C15 C20 113.72(11) . . ?
C16 C15 C20 109.86(11) . . ?
C14 C15 H15 107.0 . . ?
C16 C15 H15 107.0 . . ?
C20 C15 H15 107.0 . . ?
C22 C16 C15 112.44(11) . . ?
C22 C16 C17 106.29(11) . . ?
C15 C16 C17 113.18(11) . . ?
C22 C16 H16 108.3 . . ?
C15 C16 H16 108.3 . . ?
C17 C16 H16 108.3 . . ?
O1 C17 C18 112.24(12) . . ?
O1 C17 C16 105.66(11) . . ?
C18 C17 C16 110.71(11) . . ?
O1 C17 H17 109.4 . . ?
C18 C17 H17 109.4 . . ?
C16 C17 H17 109.4 . . ?
C17 C18 C19 112.15(12) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 111.66(11) . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 C21 106.95(11) . . ?
C19 C20 C15 109.75(11) . . ?
C21 C20 C15 114.56(12) . . ?
C19 C20 H20 108.5 . . ?
C21 C20 H20 108.5 . . ?
C15 C20 H20 108.5 . . ?
N4 C21 C20 117.72(12) . . ?
N4 C21 H21A 107.9 . . ?
C20 C21 H21A 107.9 . . ?
N4 C21 H21B 107.9 . . ?
C20 C21 H21B 107.9 . . ?
H21A C21 H21B 107.2 . . ?
O3 C22 O2 123.40(13) . . ?
O3 C22 C16 126.32(13) . . ?
O2 C22 C16 110.23(11) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 S1 C1" C2" -52.15(12) . . . . ?
C2' O2' C1' O1' 12.78(19) . . . . ?
C2' O2' C1' N4 -166.57(12) . . . . ?
C5 N4 C1' O1' -179.48(13) . . . . ?
C21 N4 C1' O1' 14.1(2) . . . . ?
C5 N4 C1' O2' -0.15(18) . . . . ?
C21 N4 C1' O2' -166.60(11) . . . . ?
C13 N1 C2 C7 0.48(15) . . . . ?
C13 N1 C2 C3 -179.57(12) . . . . ?
S1 C1" C2" C7" 132.24(13) . . . . ?
S1 C1" C2" C3" -48.71(18) . . . . ?
C7 C2 C3 C14 -103.24(16) . . . . ?
N1 C2 C3 C14 76.82(16) . . . . ?
C7 C2 C3 S1 133.34(13) . . . . ?
N1 C2 C3 S1 -46.61(16) . . . . ?
C1" S1 C3 C2 -58.92(11) . . . . ?
C1" S1 C3 C14 173.86(9) . . . . ?
C7" C2" C3" C4" 0.9(2) . . . . ?
C1" C2" C3" C4" -178.11(14) . . . . ?
C2" C3" C4" C5" 0.0(2) . . . . ?
C1' N4 C5 C6 91.54(16) . . . . ?
C21 N4 C5 C6 -102.05(14) . . . . ?
C3" C4" C5" C6" -0.8(3) . . . . ?
N4 C5 C6 C7 -45.93(16) . . . . ?
C4" C5" C6" C7" 0.8(3) . . . . ?
N1 C2 C7 C8 0.05(15) . . . . ?
C3 C2 C7 C8 -179.90(13) . . . . ?
N1 C2 C7 C6 -171.58(12) . . . . ?
C3 C2 C7 C6 8.5(2) . . . . ?
C5 C6 C7 C2 89.00(17) . . . . ?
C5 C6 C7 C8 -80.88(17) . . . . ?
C3" C2" C7" C6" -1.0(2) . . . . ?
C1" C2" C7" C6" 178.05(15) . . . . ?
C5" C6" C7" C2" 0.2(3) . . . . ?
C2 C7 C8 C9 -179.96(15) . . . . ?
C6 C7 C8 C9 -8.6(3) . . . . ?
C2 C7 C8 C13 -0.55(15) . . . . ?
C6 C7 C8 C13 170.84(13) . . . . ?
C13 C8 C9 C10 1.1(2) . . . . ?
C7 C8 C9 C10 -179.53(15) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
C9 C10 C11 C12 0.3(2) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C2 N1 C13 C12 179.82(14) . . . . ?
C2 N1 C13 C8 -0.82(15) . . . . ?
C11 C12 C13 N1 178.65(14) . . . . ?
C11 C12 C13 C8 -0.6(2) . . . . ?
C9 C8 C13 N1 -179.64(12) . . . . ?
C7 C8 C13 N1 0.84(15) . . . . ?
C9 C8 C13 C12 -0.2(2) . . . . ?
C7 C8 C13 C12 -179.74(13) . . . . ?
C2 C3 C14 C15 131.86(12) . . . . ?
S1 C3 C14 C15 -102.53(11) . . . . ?
C3 C14 C15 C16 62.25(14) . . . . ?
C3 C14 C15 C20 -62.87(14) . . . . ?
C14 C15 C16 C22 57.34(14) . . . . ?
C20 C15 C16 C22 -175.43(11) . . . . ?
C14 C15 C16 C17 177.81(11) . . . . ?
C20 C15 C16 C17 -54.96(14) . . . . ?
C22 C16 C17 O1 54.99(13) . . . . ?
C15 C16 C17 O1 -68.91(14) . . . . ?
C22 C16 C17 C18 176.74(11) . . . . ?
C15 C16 C17 C18 52.84(15) . . . . ?
O1 C17 C18 C19 64.88(15) . . . . ?
C16 C17 C18 C19 -52.92(15) . . . . ?
C17 C18 C19 C20 56.92(16) . . . . ?
C18 C19 C20 C21 176.97(12) . . . . ?
C18 C19 C20 C15 -58.20(15) . . . . ?
C14 C15 C20 C19 -177.37(11) . . . . ?
C16 C15 C20 C19 56.48(14) . . . . ?
C14 C15 C20 C21 -57.06(15) . . . . ?
C16 C15 C20 C21 176.80(11) . . . . ?
C1' N4 C21 C20 -121.28(14) . . . . ?
C5 N4 C21 C20 71.88(17) . . . . ?
C19 C20 C21 N4 -156.22(12) . . . . ?
C15 C20 C21 N4 81.93(16) . . . . ?
C23 O2 C22 O3 1.3(2) . . . . ?
C23 O2 C22 C16 -176.34(12) . . . . ?
C15 C16 C22 O3 20.52(19) . . . . ?
C17 C16 C22 O3 -103.84(16) . . . . ?
C15 C16 C22 O2 -161.96(11) . . . . ?
C17 C16 C22 O2 73.68(13) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 O3 0.86(2) 2.40(2) 3.0861(16) 136.5(17) 2_566 yes
O1 H1A O1' 0.77(3) 2.20(3) 2.8853(16) 149(3) 2_466 yes

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.047




_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_Y-22
_database_code_depnum_ccdc_archive 'CCDC 2338891'
loop_
_audit_author_name
_audit_author_address
'Khalil A. Abboud'
;Department of Chemistry, University of Florida
United States of America
;
# end Validation Reply Form

_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_SHFSU01_riv1                
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.10
RESPONSE: Three way disorder of the Cl atoms of chloroform solvents.
;
_vrf_PLAT080_riv1                
;
PROBLEM: Maximum Shift/Error ............................ 0.11 Why ?
RESPONSE: Three way disorder of the Cl atoms of chloroform solvents.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H39 Cl6 I N2 O6'
_chemical_formula_weight         947.30

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'
Cl Cl 0.1484 0.1585 '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                   12.0982(7)
_cell_length_b                   9.7700(6)
_cell_length_c                   16.9810(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.2052(11)
_cell_angle_gamma                90
_cell_volume                     1986.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.0

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.097
_exptl_absorpt_coefficient_mu    1.257
_shelx_estimated_absorpt_T_min   0.679
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7697
_exptl_absorpt_correction_T_max  0.9202
_exptl_absorpt_process_details   
'based on measured indexed crystal faces, Bruker APEX3 (Bruker, 2014)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38673
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.212
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9134
_reflns_number_gt                8258
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.889
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2014/7, Sheldrick, G. M. 2014'
_refine_special_details          
; 
All H atoms were positioned geometrically ( C---H = 0.93/1.00 Å) and 
allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). 
Methyl ones were allowed to rotate around the corresponding C---C. 

 The asymmetric unit consists of the molecule and two chloroform solvent
 molecules.  Both solvents have their chlorine atoms disordered and refined in
 three parts for one and two parts for the second.  The correct stereochemistry
 is refined using this anomalous dispersion method as can be seen from the Flack
 x parameter of 0.008(6).  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0231P)²+0.2359P] 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 3574 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.008(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9134
_refine_ls_number_parameters     559
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0532
_refine_ls_wR_factor_gt          0.0513
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.108
_refine_ls_shift/su_mean         0.004

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 0.62367(2) -0.10700(3) 0.79719(2) 0.01977(6) Uani 1 1 d . . . . .
O1" O 0.83923(18) 0.0824(2) 0.61363(15) 0.0120(5) Uani 1 1 d . . . . .
O1' O 0.81603(18) 0.3730(3) 0.33271(14) 0.0163(6) Uani 1 1 d . . . . .
O1 O 1.0585(2) 0.5912(2) 0.64178(15) 0.0182(6) Uani 1 1 d . . . . .
H1E H 1.0762 0.6792 0.6658 0.027 Uiso 1 1 d R U . . .
O2' O 0.64083(19) 0.2930(3) 0.29585(14) 0.0171(5) Uani 1 1 d . . . . .
O2 O 1.07161(19) 0.2666(2) 0.73359(14) 0.0149(5) Uani 1 1 d . . . . .
O3 O 1.11744(19) 0.2871(2) 0.61027(15) 0.0155(5) Uani 1 1 d . . . . .
N1 N 0.7189(2) -0.0199(3) 0.46105(18) 0.0130(6) Uani 1 1 d . . . . .
H1 H 0.774(3) -0.057(4) 0.467(2) 0.010(10) Uiso 1 1 d . . . . .
N4 N 0.6784(2) 0.4186(3) 0.40812(16) 0.0125(7) Uani 1 1 d . . . . .
C1" C 0.7707(3) 0.0316(3) 0.6685(2) 0.0131(7) Uani 1 1 d . . . . .
H1"A H 0.7154 -0.0340 0.6416 0.016 Uiso 1 1 calc R U . . .
H1"B H 0.7296 0.1080 0.6894 0.016 Uiso 1 1 calc R U . . .
C1' C 0.7200(3) 0.3634(3) 0.3457(2) 0.0121(8) Uani 1 1 d . . . . .
C2" C 0.8436(3) -0.0385(3) 0.7358(2) 0.0109(7) Uani 1 1 d . . . . .
C2' C 0.6776(3) 0.2411(4) 0.2261(2) 0.0157(7) Uani 1 1 d . . . . .
C2 C 0.6978(3) 0.1040(3) 0.4957(2) 0.0117(7) Uani 1 1 d . . . . .
C3" C 0.7977(2) -0.1043(5) 0.79719(17) 0.0131(6) Uani 1 1 d . . . . .
C3 C 0.7811(3) 0.1745(4) 0.5562(2) 0.0113(8) Uani 1 1 d . . . . .
H3A H 0.7397 0.2419 0.5854 0.014 Uiso 1 1 calc R U . . .
C3' C 0.7168(3) 0.1094(4) 0.2261(2) 0.0219(8) Uani 1 1 d . . . . .
H3'A H 0.7207 0.0538 0.2723 0.026 Uiso 1 1 calc R U . . .
C4" C 0.8630(3) -0.1742(4) 0.8579(2) 0.0183(8) Uani 1 1 d . . . . .
H4"A H 0.8298 -0.2175 0.8988 0.022 Uiso 1 1 calc R U . . .
C4' C 0.7507(3) 0.0592(4) 0.1565(3) 0.0265(9) Uani 1 1 d . . . . .
H4'A H 0.7781 -0.0318 0.1552 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5614(2) 0.4008(5) 0.42045(18) 0.0145(6) Uani 1 1 d . . . . .
H5A H 0.5159 0.3802 0.3686 0.017 Uiso 1 1 calc R U . . .
H5B H 0.5340 0.4882 0.4400 0.017 Uiso 1 1 calc R U . . .
C5" C 0.9783(3) -0.1800(4) 0.8581(2) 0.0192(8) Uani 1 1 d . . . . .
H5"A H 1.0243 -0.2272 0.8993 0.023 Uiso 1 1 calc R U . . .
C5' C 0.7449(3) 0.1403(4) 0.0895(2) 0.0235(9) Uani 1 1 d . . . . .
H5'A H 0.7693 0.1055 0.0426 0.028 Uiso 1 1 calc R U . . .
C6" C 1.0253(2) -0.1166(5) 0.79800(19) 0.0161(7) Uani 1 1 d . . . . .
H6"A H 1.1038 -0.1212 0.7979 0.019 Uiso 1 1 calc R U . . .
C6 C 0.5433(3) 0.2863(3) 0.4798(2) 0.0129(7) Uani 1 1 d . . . . .
H6A H 0.5753 0.3159 0.5341 0.015 Uiso 1 1 calc R U . . .
H6B H 0.4621 0.2727 0.4792 0.015 Uiso 1 1 calc R U . . .
C6' C 0.7039(3) 0.2714(4) 0.0907(2) 0.0218(8) Uani 1 1 d . . . . .
H6'A H 0.6989 0.3267 0.0443 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5950(3) 0.1526(3) 0.4620(2) 0.0114(7) Uani 1 1 d . . . . .
C7" C 0.9588(3) -0.0466(3) 0.7380(2) 0.0119(7) Uani 1 1 d . . . . .
H7"A H 0.9926 -0.0031 0.6975 0.014 Uiso 1 1 calc R U . . .
C7' C 0.6696(3) 0.3233(4) 0.1599(2) 0.0181(8) Uani 1 1 d . . . . .
H7'A H 0.6413 0.4138 0.1611 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5503(3) 0.0550(3) 0.4033(2) 0.0109(7) Uani 1 1 d . . . . .
C9 C 0.4514(3) 0.0474(4) 0.3491(2) 0.0149(7) Uani 1 1 d . . . . .
H9A H 0.3975 0.1186 0.3467 0.018 Uiso 1 1 calc R U . . .
C10 C 0.4332(3) -0.0646(4) 0.2995(2) 0.0183(8) Uani 1 1 d . . . . .
H10A H 0.3660 -0.0702 0.2631 0.022 Uiso 1 1 calc R U . . .
C11 C 0.5114(3) -0.1697(4) 0.3017(2) 0.0183(8) Uani 1 1 d . . . . .
H11A H 0.4964 -0.2457 0.2669 0.022 Uiso 1 1 calc R U . . .
C12 C 0.6109(3) -0.1653(4) 0.3540(2) 0.0150(7) Uani 1 1 d . . . . .
H12A H 0.6642 -0.2370 0.3556 0.018 Uiso 1 1 calc R U . . .
C13 C 0.6297(3) -0.0523(3) 0.4038(2) 0.0110(7) Uani 1 1 d . . . . .
C14 C 0.8717(3) 0.2536(3) 0.5189(2) 0.0104(7) Uani 1 1 d . . . . .
H14A H 0.9416 0.1996 0.5267 0.013 Uiso 1 1 calc R U . . .
H14B H 0.8474 0.2618 0.4609 0.013 Uiso 1 1 calc R U . . .
C15 C 0.8964(2) 0.3978(5) 0.55360(17) 0.0110(6) Uani 1 1 d . . . . .
H15A H 0.9541 0.4399 0.5245 0.013 Uiso 1 1 calc R U . . .
C16 C 0.9464(2) 0.3905(5) 0.64225(17) 0.0116(5) Uani 1 1 d . . . . .
H16A H 0.8904 0.3447 0.6714 0.014 Uiso 1 1 calc R U . . .
C17 C 0.9719(3) 0.5331(4) 0.6803(2) 0.0137(7) Uani 1 1 d . . . . .
H17A H 0.9989 0.5224 0.7384 0.016 Uiso 1 1 calc R U . . .
C18 C 0.8668(3) 0.6198(4) 0.6687(2) 0.0163(7) Uani 1 1 d . . . . .
H18A H 0.8098 0.5774 0.6973 0.020 Uiso 1 1 calc R U . . .
H18B H 0.8839 0.7119 0.6916 0.020 Uiso 1 1 calc R U . . .
C19 C 0.8207(3) 0.6334(4) 0.5814(2) 0.0151(8) Uani 1 1 d . . . . .
H19A H 0.8763 0.6807 0.5535 0.018 Uiso 1 1 calc R U . . .
H19B H 0.7523 0.6903 0.5759 0.018 Uiso 1 1 calc R U . . .
C20 C 0.7929(3) 0.4937(3) 0.5423(2) 0.0121(7) Uani 1 1 d . . . . .
H20A H 0.7326 0.4502 0.5682 0.015 Uiso 1 1 calc R U . . .
C21 C 0.7465(3) 0.5236(3) 0.4552(2) 0.0162(8) Uani 1 1 d . . . . .
H21A H 0.7008 0.6078 0.4543 0.019 Uiso 1 1 calc R U . . .
H21B H 0.8107 0.5450 0.4271 0.019 Uiso 1 1 calc R U . . .
C22 C 1.0534(3) 0.3090(3) 0.6571(2) 0.0122(7) Uani 1 1 d . . . . .
C23 C 1.1753(3) 0.1936(4) 0.7577(2) 0.0179(8) Uani 1 1 d . . . . .
H23A H 1.1758 0.1569 0.8115 0.027 Uiso 1 1 calc R U . . .
H23B H 1.2384 0.2564 0.7574 0.027 Uiso 1 1 calc R U . . .
H23C H 1.1818 0.1181 0.7206 0.027 Uiso 1 1 calc R U . . .
C30 C 0.5718(4) -0.3307(5) -0.0120(3) 0.0361(12) Uani 1 1 d . . . . .
H1X H 0.5352 -0.2475 -0.0382 0.043 Uiso 0.56(3) 1 calc R U P A 1
H1Y H 0.5487 -0.2430 -0.0400 0.043 Uiso 0.32(3) 1 calc R U P A 2
H1Z H 0.5163 -0.2800 -0.0505 0.043 Uiso 0.123(14) 1 calc R U P A 3
Cl1 Cl 0.4953(14) -0.378(2) 0.0643(9) 0.049(3) Uani 0.56(3) 1 d . . P A 1
Cl2 Cl 0.5625(11) -0.4584(9) -0.0826(5) 0.051(2) Uani 0.56(3) 1 d . . P A 1
Cl3 Cl 0.7090(10) -0.287(3) 0.0248(6) 0.062(6) Uani 0.56(3) 1 d . . P A 1
Cl1' Cl 0.509(2) -0.349(4) 0.075(2) 0.069(9) Uani 0.32(3) 1 d . . P A 2
Cl2' Cl 0.5460(17) -0.472(2) -0.0768(13) 0.087(6) Uani 0.32(3) 1 d . . P A 2
Cl3' Cl 0.7183(18) -0.332(3) 0.0228(13) 0.060(5) Uani 0.32(3) 1 d . . P A 2
Cl1" Cl 0.497(5) -0.404(8) 0.058(4) 0.09(2) Uani 0.123(14) 1 d . . P A 3
Cl2" Cl 0.638(5) -0.4500(18) -0.0681(16) 0.085(13) Uani 0.123(14) 1 d . . P A 3
Cl3" Cl 0.673(4) -0.211(3) 0.0280(14) 0.085(10) Uani 0.123(14) 1 d . . P A 3
C31 C 0.0864(4) -0.2216(5) 0.1287(3) 0.0335(11) Uani 1 1 d . . . . .
H1U H 0.0670 -0.2394 0.1831 0.040 Uiso 0.71(4) 1 calc R U P B 1
H1V H 0.0636 -0.2315 0.1827 0.040 Uiso 0.29(4) 1 calc R U P B 2
Cl4 Cl 0.0124(6) -0.3433(7) 0.0612(4) 0.0363(12) Uani 0.71(4) 1 d . . P B 1
Cl5 Cl 0.0605(11) -0.0496(8) 0.1063(8) 0.076(3) Uani 0.71(4) 1 d . . P B 1
Cl6 Cl 0.2324(5) -0.2568(6) 0.1304(3) 0.0322(12) Uani 0.71(4) 1 d . . P B 1
Cl4' Cl 0.0102(17) -0.319(3) 0.0671(13) 0.074(6) Uani 0.29(4) 1 d . . P B 2
Cl5' Cl 0.035(2) -0.0657(18) 0.0863(12) 0.094(6) Uani 0.29(4) 1 d . . P B 2
Cl6' Cl 0.2222(17) -0.227(3) 0.1363(11) 0.073(5) Uani 0.29(4) 1 d . . P B 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
I1 C3" 2.106(3) . ?
O1" C1" 1.423(4) . ?
O1" C3 1.435(4) . ?
O1' C1' 1.216(4) . ?
O1 C17 1.429(4) . ?
O1 H1E 0.9622 . ?
O2' C1' 1.370(4) . ?
O2' C2' 1.416(4) . ?
O2 C22 1.350(4) . ?
O2 C23 1.450(4) . ?
O3 C22 1.207(4) . ?
N1 C13 1.382(5) . ?
N1 C2 1.385(4) . ?
N1 H1 0.75(4) . ?
N4 C1' 1.349(4) . ?
N4 C5 1.471(4) . ?
N4 C21 1.478(4) . ?
C1" C2" 1.505(5) . ?
C1" H1"A 0.9900 . ?
C1" H1"B 0.9900 . ?
C2" C7" 1.391(4) . ?
C2" C3" 1.405(5) . ?
C2' C3' 1.371(5) . ?
C2' C7' 1.374(5) . ?
C2 C7 1.377(5) . ?
C2 C3 1.500(5) . ?
C3" C4" 1.386(5) . ?
C3 C14 1.549(5) . ?
C3 H3A 1.0000 . ?
C3' C4' 1.395(6) . ?
C3' H3'A 0.9500 . ?
C4" C5" 1.395(5) . ?
C4" H4"A 0.9500 . ?
C4' C5' 1.380(6) . ?
C4' H4'A 0.9500 . ?
C5 C6 1.542(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5" C6" 1.384(5) . ?
C5" H5"A 0.9500 . ?
C5' C6' 1.375(6) . ?
C5' H5'A 0.9500 . ?
C6" C7" 1.386(5) . ?
C6" H6"A 0.9500 . ?
C6 C7 1.497(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6' C7' 1.396(5) . ?
C6' H6'A 0.9500 . ?
C7 C8 1.430(5) . ?
C7" H7"A 0.9500 . ?
C7' H7'A 0.9500 . ?
C8 C9 1.403(5) . ?
C8 C13 1.422(4) . ?
C9 C10 1.379(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.393(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.391(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.390(5) . ?
C12 H12A 0.9500 . ?
C14 C15 1.540(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.542(4) . ?
C15 C20 1.553(5) . ?
C15 H15A 1.0000 . ?
C16 C22 1.510(5) . ?
C16 C17 1.548(6) . ?
C16 H16A 1.0000 . ?
C17 C18 1.517(5) . ?
C17 H17A 1.0000 . ?
C18 C19 1.512(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.535(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.533(5) . ?
C20 H20A 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C30 Cl2 1.723(10) . ?
C30 Cl1" 1.75(4) . ?
C30 Cl3 1.742(12) . ?
C30 Cl3" 1.76(3) . ?
C30 Cl1 1.758(14) . ?
C30 Cl2" 1.766(19) . ?
C30 Cl2' 1.76(2) . ?
C30 Cl1' 1.76(3) . ?
C30 Cl3' 1.79(2) . ?
C30 H1X 1.0000 . ?
C30 H1Y 1.0000 . ?
C30 H1Z 1.0000 . ?
C31 Cl4' 1.60(3) . ?
C31 Cl6' 1.63(2) . ?
C31 Cl5 1.742(8) . ?
C31 Cl5' 1.759(17) . ?
C31 Cl6 1.796(7) . ?
C31 Cl4 1.799(10) . ?
C31 H1U 1.0000 . ?
C31 H1V 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
C1" O1" C3 112.9(2) . . ?
C17 O1 H1E 107.1 . . ?
C1' O2' C2' 114.9(2) . . ?
C22 O2 C23 116.0(3) . . ?
C13 N1 C2 109.0(3) . . ?
C13 N1 H1 125(3) . . ?
C2 N1 H1 125(3) . . ?
C1' N4 C5 122.7(3) . . ?
C1' N4 C21 117.4(3) . . ?
C5 N4 C21 118.6(3) . . ?
O1" C1" C2" 108.8(3) . . ?
O1" C1" H1"A 109.9 . . ?
C2" C1" H1"A 109.9 . . ?
O1" C1" H1"B 109.9 . . ?
C2" C1" H1"B 109.9 . . ?
H1"A C1" H1"B 108.3 . . ?
O1' C1' N4 125.8(3) . . ?
O1' C1' O2' 121.9(3) . . ?
N4 C1' O2' 112.3(3) . . ?
C7" C2" C3" 117.0(3) . . ?
C7" C2" C1" 121.5(3) . . ?
C3" C2" C1" 121.4(3) . . ?
C3' C2' C7' 122.1(3) . . ?
C3' C2' O2' 119.1(3) . . ?
C7' C2' O2' 118.8(3) . . ?
C7 C2 N1 109.6(3) . . ?
C7 C2 C3 127.2(3) . . ?
N1 C2 C3 123.0(3) . . ?
C4" C3" C2" 122.3(3) . . ?
C4" C3" I1 117.2(2) . . ?
C2" C3" I1 120.4(2) . . ?
O1" C3 C2 113.2(3) . . ?
O1" C3 C14 106.5(3) . . ?
C2 C3 C14 113.2(3) . . ?
O1" C3 H3A 107.9 . . ?
C2 C3 H3A 107.9 . . ?
C14 C3 H3A 107.9 . . ?
C2' C3' C4' 118.3(4) . . ?
C2' C3' H3'A 120.9 . . ?
C4' C3' H3'A 120.9 . . ?
C3" C4" C5" 119.0(3) . . ?
C3" C4" H4"A 120.5 . . ?
C5" C4" H4"A 120.5 . . ?
C5' C4' C3' 120.7(4) . . ?
C5' C4' H4'A 119.7 . . ?
C3' C4' H4'A 119.7 . . ?
N4 C5 C6 114.1(3) . . ?
N4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
N4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C6" C5" C4" 119.8(3) . . ?
C6" C5" H5"A 120.1 . . ?
C4" C5" H5"A 120.1 . . ?
C6' C5' C4' 120.0(4) . . ?
C6' C5' H5'A 120.0 . . ?
C4' C5' H5'A 120.0 . . ?
C5" C6" C7" 120.4(3) . . ?
C5" C6" H6"A 119.8 . . ?
C7" C6" H6"A 119.8 . . ?
C7 C6 C5 113.5(3) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C5' C6' C7' 120.1(4) . . ?
C5' C6' H6'A 120.0 . . ?
C7' C6' H6'A 120.0 . . ?
C2 C7 C8 106.8(3) . . ?
C2 C7 C6 126.5(3) . . ?
C8 C7 C6 126.6(3) . . ?
C6" C7" C2" 121.5(3) . . ?
C6" C7" H7"A 119.2 . . ?
C2" C7" H7"A 119.2 . . ?
C2' C7' C6' 118.9(4) . . ?
C2' C7' H7'A 120.6 . . ?
C6' C7' H7'A 120.6 . . ?
C9 C8 C13 118.6(3) . . ?
C9 C8 C7 134.0(3) . . ?
C13 C8 C7 107.4(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
C9 C10 C11 121.3(3) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C13 C12 C11 117.7(3) . . ?
C13 C12 H12A 121.2 . . ?
C11 C12 H12A 121.2 . . ?
N1 C13 C12 130.8(3) . . ?
N1 C13 C8 107.2(3) . . ?
C12 C13 C8 122.0(3) . . ?
C15 C14 C3 114.2(3) . . ?
C15 C14 H14A 108.7 . . ?
C3 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C3 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 111.0(3) . . ?
C14 C15 C20 113.3(2) . . ?
C16 C15 C20 110.2(3) . . ?
C14 C15 H15A 107.3 . . ?
C16 C15 H15A 107.3 . . ?
C20 C15 H15A 107.3 . . ?
C22 C16 C15 113.3(3) . . ?
C22 C16 C17 106.8(2) . . ?
C15 C16 C17 113.1(4) . . ?
C22 C16 H16A 107.8 . . ?
C15 C16 H16A 107.8 . . ?
C17 C16 H16A 107.8 . . ?
O1 C17 C18 111.9(3) . . ?
O1 C17 C16 106.4(2) . . ?
C18 C17 C16 109.6(3) . . ?
O1 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C19 C18 C17 111.2(3) . . ?
C19 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 C20 111.9(3) . . ?
C18 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 106.0(3) . . ?
C21 C20 C15 114.3(3) . . ?
C19 C20 C15 111.1(3) . . ?
C21 C20 H20A 108.4 . . ?
C19 C20 H20A 108.4 . . ?
C15 C20 H20A 108.4 . . ?
N4 C21 C20 119.3(3) . . ?
N4 C21 H21A 107.5 . . ?
C20 C21 H21A 107.5 . . ?
N4 C21 H21B 107.5 . . ?
C20 C21 H21B 107.5 . . ?
H21A C21 H21B 107.0 . . ?
O3 C22 O2 123.2(3) . . ?
O3 C22 C16 126.8(3) . . ?
O2 C22 C16 109.9(3) . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Cl2 C30 Cl3 113.1(7) . . ?
Cl1" C30 Cl3" 114(3) . . ?
Cl2 C30 Cl1 109.4(10) . . ?
Cl3 C30 Cl1 112.1(7) . . ?
Cl1" C30 Cl2" 114(3) . . ?
Cl3" C30 Cl2" 107.9(12) . . ?
Cl2' C30 Cl1' 112.6(14) . . ?
Cl2' C30 Cl3' 106.3(11) . . ?
Cl1' C30 Cl3' 104.5(12) . . ?
Cl2 C30 H1X 107.3 . . ?
Cl3 C30 H1X 107.3 . . ?
Cl1 C30 H1X 107.3 . . ?
Cl2' C30 H1Y 111.1 . . ?
Cl1' C30 H1Y 111.1 . . ?
Cl3' C30 H1Y 111.1 . . ?
Cl1" C30 H1Z 106.7 . . ?
Cl3" C30 H1Z 106.6 . . ?
Cl2" C30 H1Z 106.7 . . ?
Cl4' C31 Cl6' 120.8(18) . . ?
Cl4' C31 Cl5' 96.3(15) . . ?
Cl6' C31 Cl5' 110.6(10) . . ?
Cl5 C31 Cl6 109.5(4) . . ?
Cl5 C31 Cl4 116.1(7) . . ?
Cl6 C31 Cl4 106.4(4) . . ?
Cl5 C31 H1U 108.2 . . ?
Cl6 C31 H1U 108.2 . . ?
Cl4 C31 H1U 108.2 . . ?
Cl4' C31 H1V 109.4 . . ?
Cl6' C31 H1V 109.4 . . ?
Cl5' C31 H1V 109.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1E O1' 0.96 2.30 3.144(4) 146.4 2_756
N1 H1 O3 0.75(4) 2.51(4) 3.102(4) 138(4) 2_746
C4" H4"A Cl3 0.95 2.84 3.771(11) 166.8 1_556
C4" H4"A Cl3' 0.95 2.88 3.83(2) 175.8 1_556
C5 H5A I1 0.99 3.07 4.039(3) 165.9 2_656
C7' H7'A Cl1" 0.95 2.89 3.66(8) 138.3 1_565
C12 H12A O3 0.95 2.63 3.288(4) 126.6 2_746
C14 H14A O3 0.99 2.53 3.168(4) 122.0 .
C14 H14B O1' 0.99 2.41 3.347(4) 156.9 .
C14 H14B N4 0.99 2.61 3.217(4) 119.7 .
C17 H17A Cl5 1.00 2.92 3.788(12) 146.1 2_656
C21 H21B O3 0.99 2.63 3.331(4) 128.0 2_756
C23 H23A Cl3 0.98 2.98 3.762(10) 137.9 2_756
C23 H23A Cl3' 0.98 2.92 3.77(2) 145.8 2_756
C23 H23C O1' 0.98 2.56 3.496(5) 159.4 2_746
C30 H1Y I1 1.00 3.31 4.032(4) 130.6 1_554
C31 H1V O2 1.00 2.31 3.227(5) 151.2 2_646

_refine_diff_density_max         0.688
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.063

