# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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. 
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data_JF2892FMI
_database_code_depnum_ccdc_archive 'CCDC 2096009'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
Cis-N-(4-iodophenyl)-2-2-methyl-3-phenyl-2,3-dihydrobenzofuran-2-yl)acetamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 I N O2'
_chemical_formula_sum            'C23 H20 I N O2'
_chemical_formula_weight         469.30

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   14.3788(8)
_cell_length_b                   7.5241(5)
_cell_length_c                   35.493(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3839.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9791
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.50

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    1.686
_shelx_estimated_absorpt_T_min   0.629
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_T_max  0.7785
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32003
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.697
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4415
_reflns_number_gt                3980
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 (2017.3) (Bruker, 2017)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
JF2892 Kappa Mo

A yellow block with approximate orthogonal dimensions 0.104 x 0.182 x
0.303mm3 was placed and optically centered on the Bruker(1) Venture Dual
source Kappa Photon diffractometer system at --173°C(100K).  Indexing of the
unit cell used a random set of reflections collected from three series of
0.5° wide omega-scans, 10 seconds per frame, and 30 frames per series that
were well distributed in reciprocal space. Data were collected [MoKa] with
0.3° wide scans, variable time per frame dependent upon detector 2theta angle
and varying phi and omega angles such that nearly all unique reflections were
collected at least once.  The crystal to detector distance was 55.0mm, thus
providing a complete sphere of data to 2thetamax=54.97°.


Structural determination and Refinement:

All crystallographic calculations were performed on an Intel Xeon E5-1620v2
at 3.70GHz an eight core processor and 16GB of extended memory. Data
collected were corrected for Lorentz and polarization effects with Saint(1)
and absorption using Blessing?s method and merged as incorporated with the
program Sadabs(2,3). The SHELXTL(4) program package was implemented to
determine the probable space group and set up the initial files. System
symmetry, systematic absences and intensity statistics indicated the
centrosymmetric orthorhombic space group Pbca (no. 61). The structure was
determined by direct methods with the non-hydrogen atoms being located
directly for the molecule using the program XT(5).  The structure was refined
with XL(6). The 70519 data collected were initially merged based upon
identical indices to 32003 and then merged for least squares refinement to
4415 unique data [R(int)=0.0203]. All non-hydrogen atoms were refined
anisotropically. A large portion of the molecule suffered from disorder and
was refined as two parts thereafter with the final ratio 0.74:0.26.  This led
to two C-I bond lengths that should be equivalent but appear to not be with
C(15)-I(15) 2.155(3) and C(15b)-I(15b) = 1.925(6) and this could be due to
this half of the molecule being disordered with the iodine atom being the
furthest from the point where the disorder begins. Hydrogen atoms were
idealized throughout the final refinement stages. The final structure was
refined to convergence with R(F)=4.03%, wR(F2)=7.38%, GOF=1.155 for all 4415
unique reflections [R(F)=3.59, wR(F2)=7.15% for those 3980 data with Fo >
4sigma(Fo)]. The final difference-Fourier map was featureless indicating that
the structure is both correct and complete. An empirical correction for
extinction was also attempted and found to be 0.0056(2).


References:

1.	Bruker (2013) APEXII (Version 2017.3) and (2016) SAINT (Version 8.37a).
Bruker AXS Inc., Madison, Wisconsin, USA.

2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H.
(1995). Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, ?Siemens Area Detector
Absorption Correction? Universität Göttingen: Göttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison,
Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, Universität Göttingen: Göttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2018). SHELXL2018/3. Universität Göttingen: Göttingen,
Germany.


Acknowledgment:  We thank the National Science Foundation (Grant CHE-1531193)
for the Dual Source X-ray diffractometer.






;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0153P)²+6.6029P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00564(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4415
_refine_ls_number_parameters     334
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.47363(19) 0.4616(4) 0.35010(8) 0.0362(6) Uani 1 1 d D . . . .
O1 O 0.49778(13) 0.3739(3) 0.38570(5) 0.0386(4) Uani 1 1 d . . . . .
C2 C 0.5137(2) 0.3371(4) 0.31821(8) 0.0384(6) Uani 1 1 d . . . . .
H2 H 0.549534 0.411799 0.299989 0.040(8) Uiso 1 1 calc R . . . .
C3 C 0.58116(18) 0.2259(4) 0.34035(9) 0.0399(6) Uani 1 1 d . . . . .
C4 C 0.6474(2) 0.1035(4) 0.32869(11) 0.0528(9) Uani 1 1 d . . . . .
H4 H 0.657772 0.083372 0.302606 0.052(10) Uiso 1 1 calc R . . . .
C5 C 0.6983(2) 0.0106(4) 0.35548(12) 0.0586(10) Uani 1 1 d . . . . .
H5 H 0.744165 -0.072657 0.347739 0.064(11) Uiso 1 1 calc R . . . .
C6 C 0.6825(2) 0.0390(4) 0.39308(12) 0.0546(9) Uani 1 1 d . . . . .
H6 H 0.717324 -0.026126 0.411148 0.061(11) Uiso 1 1 calc R . . . .
C7 C 0.6163(2) 0.1615(4) 0.40540(10) 0.0463(7) Uani 1 1 d . . . . .
H7 H 0.605776 0.181873 0.431467 0.043(9) Uiso 1 1 calc R . . . .
C8 C 0.56677(17) 0.2518(4) 0.37820(9) 0.0374(6) Uani 1 1 d . . . . .
C9 C 0.5250(2) 0.6377(4) 0.34918(8) 0.0458(7) Uani 1 1 d . . . . .
H9A H 0.507155 0.709076 0.371115 0.056(10) Uiso 1 1 calc R . . . .
H9B H 0.508940 0.701935 0.326058 0.064(11) Uiso 1 1 calc R . . . .
H9C H 0.592219 0.615931 0.349771 0.059(11) Uiso 1 1 calc R . . . .
C10 C 0.3680(3) 0.4938(6) 0.34745(13) 0.0359(9) Uani 0.74 1 d D U P A 1
H10A H 0.353982 0.553239 0.323226 0.043 Uiso 0.74 1 calc R U P A 1
H10B H 0.335599 0.377765 0.347557 0.043 Uiso 0.74 1 calc R U P A 1
C11 C 0.3312(3) 0.6057(6) 0.37916(13) 0.0327(11) Uani 0.74 1 d D U P A 1
N11 N 0.2694(2) 0.5241(4) 0.40173(9) 0.0373(7) Uani 0.74 1 d D . P A 1
H11 H 0.254113 0.414129 0.395942 0.045 Uiso 0.74 1 calc R U P A 1
O11 O 0.35267(19) 0.7630(4) 0.38266(9) 0.0459(7) Uani 0.74 1 d D U P A 1
C12 C 0.2265(2) 0.5991(4) 0.43403(7) 0.0373(10) Uani 0.74 1 d DG . P A 1
C13 C 0.27994(18) 0.6861(4) 0.46097(9) 0.0389(10) Uani 0.74 1 d G . P A 1
H13 H 0.345175 0.697712 0.457517 0.047 Uiso 0.74 1 calc R U P A 1
C14 C 0.2379(2) 0.7560(5) 0.49296(8) 0.0402(11) Uani 0.74 1 d G . P A 1
H14 H 0.274390 0.815479 0.511377 0.048 Uiso 0.74 1 calc R U P A 1
C15 C 0.1424(2) 0.7390(5) 0.49802(8) 0.0414(14) Uani 0.74 1 d G . P A 1
C16 C 0.08905(17) 0.6521(5) 0.47108(11) 0.0433(13) Uani 0.74 1 d G . P A 1
H16 H 0.023811 0.640439 0.474530 0.052 Uiso 0.74 1 calc R U P A 1
C17 C 0.1311(2) 0.5821(4) 0.43908(9) 0.0431(12) Uani 0.74 1 d G . P A 1
H17 H 0.094594 0.522671 0.420669 0.052 Uiso 0.74 1 calc R U P A 1
I15 I 0.07892(6) 0.87616(18) 0.54470(2) 0.04160(16) Uani 0.74 1 d . . P A 1
C10B C 0.3669(6) 0.4276(17) 0.3559(4) 0.0324(17) Uani 0.26 1 d D U P A 2
H10C H 0.336734 0.431038 0.330816 0.039 Uiso 0.26 1 calc R U P A 2
H10D H 0.359215 0.305557 0.365815 0.039 Uiso 0.26 1 calc R U P A 2
C11B C 0.3138(10) 0.5541(16) 0.3818(3) 0.0313(19) Uani 0.26 1 d D U P A 2
N11B N 0.3231(6) 0.5274(11) 0.4188(2) 0.0304(17) Uani 0.26 1 d D . P A 2
H11B H 0.366230 0.453359 0.426743 0.036 Uiso 0.26 1 calc R U P A 2
O11B O 0.2721(5) 0.6826(10) 0.3689(2) 0.0411(16) Uani 0.26 1 d D U P A 2
C12B C 0.2657(6) 0.6144(10) 0.4463(2) 0.025(2) Uani 0.26 1 d DG . P A 2
C13B C 0.3079(4) 0.6803(11) 0.4786(2) 0.035(2) Uani 0.26 1 d G . P A 2
H13B H 0.373365 0.670997 0.481671 0.043 Uiso 0.26 1 calc R U P A 2
C14B C 0.2543(5) 0.7597(13) 0.50654(19) 0.029(3) Uani 0.26 1 d G . P A 2
H14B H 0.283138 0.804667 0.528655 0.035 Uiso 0.26 1 calc R U P A 2
C15B C 0.1585(5) 0.7733(13) 0.5021(2) 0.028(3) Uani 0.26 1 d G . P A 2
C16B C 0.1163(4) 0.7074(11) 0.4697(2) 0.025(2) Uani 0.26 1 d G . P A 2
H16B H 0.050875 0.716701 0.466701 0.030 Uiso 0.26 1 calc R U P A 2
C17B C 0.1699(6) 0.6280(10) 0.44183(18) 0.029(2) Uani 0.26 1 d G . P A 2
H17B H 0.141100 0.583030 0.419717 0.035 Uiso 0.26 1 calc R U P A 2
I15B I 0.0779(3) 0.8308(5) 0.54363(10) 0.0731(14) Uani 0.26 1 d . . P A 2
C18 C 0.4443(2) 0.2259(4) 0.29635(7) 0.0359(6) Uani 1 1 d . . . . .
C19 C 0.40575(19) 0.0722(4) 0.31154(7) 0.0357(6) Uani 1 1 d . . . . .
H19 H 0.423037 0.034896 0.336131 0.040(8) Uiso 1 1 calc R . . . .
C20 C 0.3422(2) -0.0269(4) 0.29097(8) 0.0390(6) Uani 1 1 d . . . . .
H20 H 0.315969 -0.131537 0.301533 0.039(8) Uiso 1 1 calc R . . . .
C21 C 0.3170(2) 0.0262(4) 0.25517(8) 0.0434(7) Uani 1 1 d . . . . .
H21 H 0.273599 -0.042052 0.241102 0.053(10) Uiso 1 1 calc R . . . .
C22 C 0.3548(2) 0.1783(4) 0.23981(8) 0.0490(8) Uani 1 1 d . . . . .
H22 H 0.337253 0.214949 0.215206 0.056(10) Uiso 1 1 calc R . . . .
C23 C 0.4182(2) 0.2775(4) 0.26020(8) 0.0456(7) Uani 1 1 d . . . . .
H23 H 0.444144 0.381858 0.249436 0.059(10) Uiso 1 1 calc R . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.467(3) . ?
C1 C9 1.518(4) . ?
C1 C10 1.540(4) . ?
C1 C10B 1.569(8) . ?
C1 C2 1.578(4) . ?
O1 C8 1.378(3) . ?
C2 C3 1.503(4) . ?
C2 C18 1.515(4) . ?
C2 H2 1.0000 . ?
C3 C8 1.373(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.389(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(4) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.502(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O11 1.229(5) . ?
C11 N11 1.346(5) . ?
N11 C12 1.418(4) . ?
N11 H11 0.8800 . ?
C12 C13 1.3900 . ?
C12 C17 1.3900 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 I15 2.155(3) . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C10B C11B 1.529(18) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B O11B 1.227(10) . ?
C11B N11B 1.335(9) . ?
N11B C12B 1.434(7) . ?
N11B H11B 0.8800 . ?
C12B C13B 1.3900 . ?
C12B C17B 1.3900 . ?
C13B C14B 1.3900 . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3900 . ?
C14B H14B 0.9500 . ?
C15B C16B 1.3900 . ?
C15B I15B 1.925(6) . ?
C16B C17B 1.3900 . ?
C16B H16B 0.9500 . ?
C17B H17B 0.9500 . ?
C18 C19 1.391(4) . ?
C18 C23 1.392(4) . ?
C19 C20 1.387(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.380(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.382(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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
O1 C1 C9 107.2(2) . . ?
O1 C1 C10 110.9(3) . . ?
C9 C1 C10 110.0(3) . . ?
O1 C1 C10B 92.6(5) . . ?
C9 C1 C10B 128.4(5) . . ?
O1 C1 C2 105.3(2) . . ?
C9 C1 C2 109.0(2) . . ?
C10 C1 C2 114.2(3) . . ?
C10B C1 C2 110.7(6) . . ?
C8 O1 C1 107.7(2) . . ?
C3 C2 C18 112.7(2) . . ?
C3 C2 C1 101.0(2) . . ?
C18 C2 C1 117.0(2) . . ?
C3 C2 H2 108.6 . . ?
C18 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C8 C3 C4 119.3(3) . . ?
C8 C3 C2 109.6(2) . . ?
C4 C3 C2 131.0(3) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 117.3(3) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
C3 C8 O1 113.1(3) . . ?
C3 C8 C7 122.5(3) . . ?
O1 C8 C7 124.4(3) . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 113.0(3) . . ?
C11 C10 H10A 109.0 . . ?
C1 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C1 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
O11 C11 N11 123.1(4) . . ?
O11 C11 C10 121.8(4) . . ?
N11 C11 C10 115.0(4) . . ?
C11 N11 C12 125.9(3) . . ?
C11 N11 H11 117.1 . . ?
C12 N11 H11 117.1 . . ?
C13 C12 C17 120.0 . . ?
C13 C12 N11 120.2(3) . . ?
C17 C12 N11 119.8(3) . . ?
C14 C13 C12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 I15 118.27(18) . . ?
C16 C15 I15 121.34(19) . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C12 120.0 . . ?
C16 C17 H17 120.0 . . ?
C12 C17 H17 120.0 . . ?
C11B C10B C1 117.8(10) . . ?
C11B C10B H10C 107.9 . . ?
C1 C10B H10C 107.9 . . ?
C11B C10B H10D 107.9 . . ?
C1 C10B H10D 107.9 . . ?
H10C C10B H10D 107.2 . . ?
O11B C11B N11B 122.4(12) . . ?
O11B C11B C10B 120.5(10) . . ?
N11B C11B C10B 116.7(9) . . ?
C11B N11B C12B 122.8(9) . . ?
C11B N11B H11B 118.6 . . ?
C12B N11B H11B 118.6 . . ?
C13B C12B C17B 120.0 . . ?
C13B C12B N11B 118.2(7) . . ?
C17B C12B N11B 121.8(7) . . ?
C12B C13B C14B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C13B C14B C15B 120.0 . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B I15B 116.7(5) . . ?
C14B C15B I15B 121.8(5) . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C16B C17B C12B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C12B C17B H17B 120.0 . . ?
C19 C18 C23 118.8(3) . . ?
C19 C18 C2 121.5(2) . . ?
C23 C18 C2 119.7(3) . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C18 120.7(3) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?

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
C9 C1 O1 C8 -98.7(3) . . . . ?
C10 C1 O1 C8 141.3(3) . . . . ?
C10B C1 O1 C8 129.6(5) . . . . ?
C2 C1 O1 C8 17.3(3) . . . . ?
O1 C1 C2 C3 -17.3(3) . . . . ?
C9 C1 C2 C3 97.5(3) . . . . ?
C10 C1 C2 C3 -139.2(3) . . . . ?
C10B C1 C2 C3 -116.2(5) . . . . ?
O1 C1 C2 C18 105.4(3) . . . . ?
C9 C1 C2 C18 -139.8(3) . . . . ?
C10 C1 C2 C18 -16.5(4) . . . . ?
C10B C1 C2 C18 6.5(6) . . . . ?
C18 C2 C3 C8 -113.8(3) . . . . ?
C1 C2 C3 C8 11.9(3) . . . . ?
C18 C2 C3 C4 62.6(4) . . . . ?
C1 C2 C3 C4 -171.7(3) . . . . ?
C8 C3 C4 C5 -0.5(4) . . . . ?
C2 C3 C4 C5 -176.6(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C4 C3 C8 O1 -178.6(2) . . . . ?
C2 C3 C8 O1 -1.7(3) . . . . ?
C4 C3 C8 C7 0.5(4) . . . . ?
C2 C3 C8 C7 177.4(3) . . . . ?
C1 O1 C8 C3 -10.3(3) . . . . ?
C1 O1 C8 C7 170.5(3) . . . . ?
C6 C7 C8 C3 -0.5(4) . . . . ?
C6 C7 C8 O1 178.5(3) . . . . ?
O1 C1 C10 C11 58.6(4) . . . . ?
C9 C1 C10 C11 -59.8(4) . . . . ?
C2 C1 C10 C11 177.3(3) . . . . ?
C1 C10 C11 O11 66.8(5) . . . . ?
C1 C10 C11 N11 -116.9(4) . . . . ?
O11 C11 N11 C12 -5.6(7) . . . . ?
C10 C11 N11 C12 178.2(3) . . . . ?
C11 N11 C12 C13 -48.3(5) . . . . ?
C11 N11 C12 C17 133.1(4) . . . . ?
C17 C12 C13 C14 0.0 . . . . ?
N11 C12 C13 C14 -178.6(3) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C13 C14 C15 I15 -172.9(3) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
I15 C15 C16 C17 172.7(3) . . . . ?
C15 C16 C17 C12 0.0 . . . . ?
C13 C12 C17 C16 0.0 . . . . ?
N11 C12 C17 C16 178.6(3) . . . . ?
O1 C1 C10B C11B 80.7(9) . . . . ?
C9 C1 C10B C11B -33.7(12) . . . . ?
C2 C1 C10B C11B -171.8(7) . . . . ?
C1 C10B C11B O11B 94.8(15) . . . . ?
C1 C10B C11B N11B -78.7(14) . . . . ?
O11B C11B N11B C12B 18(2) . . . . ?
C10B C11B N11B C12B -169.0(9) . . . . ?
C11B N11B C12B C13B -137.6(10) . . . . ?
C11B N11B C12B C17B 44.8(13) . . . . ?
C17B C12B C13B C14B 0.0 . . . . ?
N11B C12B C13B C14B -177.6(8) . . . . ?
C12B C13B C14B C15B 0.0 . . . . ?
C13B C14B C15B C16B 0.0 . . . . ?
C13B C14B C15B I15B 165.6(7) . . . . ?
C14B C15B C16B C17B 0.0 . . . . ?
I15B C15B C16B C17B -166.3(7) . . . . ?
C15B C16B C17B C12B 0.0 . . . . ?
C13B C12B C17B C16B 0.0 . . . . ?
N11B C12B C17B C16B 177.6(8) . . . . ?
C3 C2 C18 C19 39.2(4) . . . . ?
C1 C2 C18 C19 -77.2(4) . . . . ?
C3 C2 C18 C23 -140.7(3) . . . . ?
C1 C2 C18 C23 102.8(3) . . . . ?
C23 C18 C19 C20 -0.2(4) . . . . ?
C2 C18 C19 C20 179.8(3) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C21 C22 C23 0.2(5) . . . . ?
C21 C22 C23 C18 -0.2(5) . . . . ?
C19 C18 C23 C22 0.3(5) . . . . ?
C2 C18 C23 C22 -179.8(3) . . . . ?

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
C9 H9A O11 0.98 2.29 2.906(4) 120. . yes
C9 H9A I15 0.98 3.23 3.847(3) 123. 4_566 yes
C9 H9A I15B 0.98 3.21 3.887(5) 128. 4_566 yes
N11 H11 O11 0.88 1.97 2.719(4) 143. 8_655 yes
C17 H17 O11 0.95 2.49 3.135(4) 125. 8_655 yes
N11B H11B O1 0.88 2.46 3.005(7) 121. . yes
C13B H13B I15B 0.95 3.07 3.962(7) 156. 4_566 yes

_refine_diff_density_max         0.758
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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_JF2873FF
_database_code_depnum_ccdc_archive 'CCDC 2096010'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
Trans-N-(4-iodophenyl)-2-2-methyl-3-phenyl-2,3-dihydrobenzofuran-2-yl)acetamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 I N O2'
_chemical_formula_sum            'C23 H20 I N O2'
_chemical_formula_weight         469.30

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.7754(5)
_cell_length_b                   8.8984(6)
_cell_length_c                   12.8772(8)
_cell_angle_alpha                99.2233(18)
_cell_angle_beta                 96.0361(18)
_cell_angle_gamma                91.1970(17)
_cell_volume                     986.31(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9172
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.68

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    1.641
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7842
_exptl_absorpt_correction_T_max  0.8365
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49290
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.336
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11503
_reflns_number_gt                10996
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.997
_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       'Apex3 (2017.3) (Bruker, 2017)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
JF2873 Mo 

A colorless block with approximate orthogonal dimensions 0.308 x 0.096 x
0.038mm3 was placed and optically centered on the Bruker Venture Duo(l) source
Kappa Photon100 diffractometer system at --173°C(100K).  Indexing of the unit
cell used a random set of reflections collected from three series of 0.3° wide
omega-scans, 5 seconds per frame, and 30 frames per series that were well
distributed in reciprocal space. Data were collected [MoKa] with 0.3° wide
scans, variable time per frame dependent upon detector 2theta angle and
varying phi and omega angles such that nearly all unique reflections were
collected at least once.  The crystal to detector distance was 65.0mm, thus
providing a nearly complete, 99.9%, sphere of data to 2thetamax=61.26°.

Structural determination and Refinement:

All crystallographic calculations were performed on an Intel Xeon E5-1620v2 at
3.70GHz an eight core processor and 16GB of extended memory. Data collected
were corrected for Lorentz and polarization effects with Saint(1) and
absorption using Blessing?s method and merged as incorporated with the program
Sadabs(2,3). The SHELXTL(4) program package was implemented to determine the
probable space group and set up the initial files. System symmetry, lack of
systematic absences and intensity statistics indicated the non-centrosymmetric
triclinic space group P1 (no. 1). The structure was determined by direct
methods with a majority of the non-hydrogen atoms for the two unique molecules
being located directly using the program XT(5).  The structure was refined
with XL(6). The data collected were merged for least squares refinement to
11503 unique data [R(int)=0.0213]. Multiple least-squares difference-Fourier
maps were employed to determine the locations of the hydrogen atoms for the
two molecules and all were present. Hydrogen atoms were then idealized with
their thermal parameters allowed to refine. Overlaying the two molecules on
top of one another shows that they are indeed identical with slight group
rotations one to the other. All non-hydrogen atoms were refined
anisotropically. The final structure was refined to convergence with
R(F)=2.17%, wR(F2)=4.08%, GOF=1.059 for all 11503 unique reflections
[R(F)=1.94, wR(F2)=3.99% for those 10996 data with Fo > 4?(Fo)]. The final
difference-Fourier map was featureless indicating that the structure is both
correct and complete.  An empirical correction for extinction was also
attempted and found to be 0.0076(4). The absolute configuration structure
parameter, Flack(x)(7), was determined to be -0.034(4) while the Hooft(y(8)
parameter is -0.037(2) and the Parsons(z) parameter is -0.027(3) definitively
indicating that the structure is correct and complete.


1.	Bruker (2017) APEX3 (Version 2017.3) and (2017) SAINT (Version 8.38a).
Bruker AXS Inc., Madison, Wisconsin, USA.

2.	An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995).
Acta Cryst., A51, 33-38.

3.	Sheldrick, G.M., SADABS (2016) Version 2016/2, ?Siemens Area Detector
Absorption Correction? Universität Göttingen: Göttingen, Germany.

4.	Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc., Madison,
Wisconsin, USA.

5.	Sheldrick, G. M., (2014) SHELXT, Universität Göttingen: Göttingen,
Germany.  Structure determination program. Private communication.

6.	Sheldrick, G. M., (2018). SHELXL2018/3. Universität Göttingen: Göttingen,
Germany.

7.	On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta Cryst., A39,
876-881.

8.	Hooft, R.W., Straver, L.H. & Spek, A.L. (2008). J. Appl, Cryst. 41, 96-
103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron


Acknowledgment:  We thank the National Science Foundation (Grant 1531193) for
the Dual source X-ray diffractometer.
J.C.Fettinger 9.9.2019


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+0.3992P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0076(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 5250 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.034(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         11503
_refine_ls_number_parameters     530
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0194
_refine_ls_wR_factor_ref         0.0408
_refine_ls_wR_factor_gt          0.0399
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1510(3) 0.5924(3) 0.26687(19) 0.0145(5) Uani 1 1 d . . . . .
O1 O 0.2967(2) 0.5114(2) 0.27073(15) 0.0183(4) Uani 1 1 d . . . . .
C2 C 0.1912(3) 0.7429(3) 0.22483(19) 0.0157(5) Uani 1 1 d . . . . .
H2 H 0.227539 0.821056 0.287892 0.017(8) Uiso 1 1 calc R . . . .
C3 C 0.3287(3) 0.6975(3) 0.16869(19) 0.0155(5) Uani 1 1 d . . . . .
C4 C 0.4065(4) 0.7686(5) 0.1004(3) 0.0201(7) Uani 1 1 d . . . . .
H4 H 0.368768 0.858509 0.077475 0.032(10) Uiso 1 1 calc R . . . .
C5 C 0.5394(3) 0.7075(3) 0.0659(2) 0.0229(6) Uani 1 1 d . . . . .
H5 H 0.592222 0.754053 0.017924 0.044(11) Uiso 1 1 calc R . . . .
C6 C 0.5954(3) 0.5784(3) 0.1014(2) 0.0229(6) Uani 1 1 d . . . . .
H6 H 0.688496 0.539223 0.078891 0.022(8) Uiso 1 1 calc R . . . .
C7 C 0.5186(3) 0.5040(3) 0.1697(2) 0.0219(5) Uani 1 1 d . . . . .
H7 H 0.556702 0.414500 0.193039 0.023(8) Uiso 1 1 calc R . . . .
C8 C 0.3848(3) 0.5662(3) 0.2018(2) 0.0169(6) Uani 1 1 d . . . . .
C9 C 0.0340(3) 0.4871(3) 0.1932(2) 0.0211(5) Uani 1 1 d . . . . .
H9A H 0.065197 0.471393 0.121544 0.036(10) Uiso 1 1 calc R . . . .
H9B H -0.066577 0.533009 0.192512 0.022(9) Uiso 1 1 calc R . . . .
H9C H 0.027810 0.388925 0.218120 0.026(9) Uiso 1 1 calc R . . . .
C10 C 0.1088(3) 0.6307(3) 0.38066(19) 0.0157(5) Uani 1 1 d . . . . .
H10A H 0.202485 0.668745 0.428124 0.024(9) Uiso 1 1 calc R . . . .
H10B H 0.035550 0.713984 0.383994 0.013(7) Uiso 1 1 calc R . . . .
C11 C 0.0387(3) 0.4978(3) 0.4212(2) 0.0140(5) Uani 1 1 d . . . . .
N11 N 0.1384(2) 0.4185(2) 0.47702(17) 0.0157(4) Uani 1 1 d . . . . .
H11 H 0.234254 0.453452 0.489429 0.030(10) Uiso 1 1 calc R . . . .
O11 O -0.0992(3) 0.4649(3) 0.40241(18) 0.0183(5) Uani 1 1 d . . . . .
C12 C 0.1023(3) 0.2845(3) 0.51719(19) 0.0148(5) Uani 1 1 d . . . . .
C13 C 0.1935(3) 0.2525(3) 0.6055(2) 0.0159(5) Uani 1 1 d . . . . .
H13 H 0.276199 0.320726 0.637398 0.032(10) Uiso 1 1 calc R . . . .
C14 C 0.1649(3) 0.1218(3) 0.6475(2) 0.0177(5) Uani 1 1 d . . . . .
H14 H 0.226261 0.101181 0.708549 0.020(8) Uiso 1 1 calc R . . . .
C15 C 0.0453(3) 0.0213(3) 0.5992(2) 0.0174(5) Uani 1 1 d . . . . .
I15 I -0.00488(2) -0.17781(2) 0.65919(2) 0.02337(6) Uani 1 1 d . . . . .
C16 C -0.0441(4) 0.0507(4) 0.5105(3) 0.0196(7) Uani 1 1 d . . . . .
H16 H -0.124558 -0.019486 0.477561 0.030(9) Uiso 1 1 calc R . . . .
C17 C -0.0166(4) 0.1835(4) 0.4690(3) 0.0192(7) Uani 1 1 d . . . . .
H17 H -0.078849 0.204384 0.408442 0.028(9) Uiso 1 1 calc R . . . .
C18 C 0.0660(3) 0.8126(3) 0.1606(2) 0.0194(5) Uani 1 1 d . . . . .
C19 C -0.0053(4) 0.9413(3) 0.2065(3) 0.0285(6) Uani 1 1 d . . . . .
H19 H 0.019557 0.979970 0.279673 0.025(9) Uiso 1 1 calc R . . . .
C20 C -0.1126(4) 1.0135(4) 0.1462(4) 0.0408(10) Uani 1 1 d . . . . .
H20 H -0.160416 1.101250 0.178124 0.039(11) Uiso 1 1 calc R . . . .
C21 C -0.1497(4) 0.9578(5) 0.0395(4) 0.0429(10) Uani 1 1 d . . . . .
H21 H -0.222745 1.007478 -0.001659 0.064(15) Uiso 1 1 calc R . . . .
C22 C -0.0801(4) 0.8289(5) -0.0074(4) 0.0340(9) Uani 1 1 d . . . . .
H22 H -0.106062 0.789844 -0.080326 0.037(11) Uiso 1 1 calc R . . . .
C23 C 0.0276(3) 0.7579(4) 0.0532(2) 0.0258(6) Uani 1 1 d . . . . .
H23 H 0.075751 0.670573 0.020966 0.032(10) Uiso 1 1 calc R . . . .
C31 C 0.7309(3) 0.4118(3) 0.7091(2) 0.0157(5) Uani 1 1 d . . . . .
O31 O 0.8795(2) 0.4918(2) 0.70645(15) 0.0192(4) Uani 1 1 d . . . . .
C32 C 0.7792(3) 0.2611(3) 0.7501(2) 0.0154(5) Uani 1 1 d . U . . .
H32 H 0.805503 0.188694 0.687321 0.012(4) Uiso 1 1 calc R U . . .
C33 C 0.9282(3) 0.3137(3) 0.8163(2) 0.0182(5) Uani 1 1 d . . . . .
C34 C 1.0184(5) 0.2498(5) 0.8914(3) 0.0235(8) Uani 1 1 d . . . . .
H34 H 0.982947 0.161058 0.915316 0.041(11) Uiso 1 1 calc R . . . .
C35 C 1.1603(3) 0.3166(4) 0.9310(2) 0.0260(6) Uani 1 1 d . . . . .
H35 H 1.221782 0.275413 0.984073 0.026(9) Uiso 1 1 calc R . . . .
C36 C 1.2141(3) 0.4441(4) 0.8938(2) 0.0260(6) Uani 1 1 d . . . . .
H36 H 1.313190 0.487074 0.920554 0.042(11) Uiso 1 1 calc R . . . .
C37 C 1.1252(3) 0.5101(3) 0.8180(2) 0.0235(6) Uani 1 1 d . . . . .
H37 H 1.161598 0.596949 0.792357 0.027(9) Uiso 1 1 calc R . . . .
C38 C 0.9816(4) 0.4431(4) 0.7818(2) 0.0180(6) Uani 1 1 d . . . . .
C39 C 0.6427(3) 0.5170(3) 0.7845(2) 0.0203(5) Uani 1 1 d . . . . .
H39A H 0.699334 0.533631 0.855438 0.019(8) Uiso 1 1 calc R . . . .
H39B H 0.541391 0.470340 0.787313 0.030(10) Uiso 1 1 calc R . . . .
H39C H 0.630627 0.614907 0.759492 0.025(9) Uiso 1 1 calc R . . . .
C40 C 0.6509(3) 0.3755(3) 0.5956(2) 0.0160(5) Uani 1 1 d . . . . .
H40A H 0.728938 0.343993 0.547064 0.056(13) Uiso 1 1 calc R . . . .
H40B H 0.577710 0.287887 0.591013 0.029(9) Uiso 1 1 calc R . . . .
C41 C 0.5653(4) 0.5058(3) 0.5579(2) 0.0154(6) Uani 1 1 d . . . . .
N41 N 0.6416(2) 0.5887(2) 0.49870(17) 0.0156(4) Uani 1 1 d . . . . .
H41 H 0.731981 0.557057 0.482896 0.026(9) Uiso 1 1 calc R . . . .
O41 O 0.4355(3) 0.5332(3) 0.58111(18) 0.0192(5) Uani 1 1 d . . . . .
C42 C 0.5906(3) 0.7208(3) 0.45993(19) 0.0149(5) Uani 1 1 d . . . . .
C43 C 0.4791(4) 0.8123(4) 0.5039(3) 0.0178(7) Uani 1 1 d . . . . .
H43 H 0.431755 0.785189 0.561620 0.021(8) Uiso 1 1 calc R . . . .
C44 C 0.4372(4) 0.9424(4) 0.4638(3) 0.0208(7) Uani 1 1 d . . . . .
H44 H 0.361230 1.004398 0.494190 0.032(10) Uiso 1 1 calc R . . . .
C45 C 0.5056(3) 0.9829(3) 0.3793(2) 0.0183(5) Uani 1 1 d . . . . .
I45 I 0.43242(2) 1.17787(2) 0.31893(2) 0.02494(6) Uani 1 1 d . . . . .
C46 C 0.6176(3) 0.8933(3) 0.3349(2) 0.0178(5) Uani 1 1 d . . . . .
H46 H 0.664617 0.920905 0.277149 0.023(8) Uiso 1 1 calc R . . . .
C47 C 0.6603(3) 0.7628(3) 0.3758(2) 0.0158(5) Uani 1 1 d . . . . .
H47 H 0.737499 0.701888 0.346156 0.018(8) Uiso 1 1 calc R . . . .
C48 C 0.6630(3) 0.1788(3) 0.8012(2) 0.0177(5) Uani 1 1 d . . . . .
C49 C 0.6242(3) 0.2304(3) 0.9028(2) 0.0234(6) Uani 1 1 d . . . . .
H49 H 0.671571 0.321782 0.942505 0.033(10) Uiso 1 1 calc R . . . .
C50 C 0.5172(4) 0.1499(5) 0.9467(3) 0.0276(8) Uani 1 1 d . . . . .
H50 H 0.491655 0.186883 1.015815 0.037(13) Uiso 1 1 calc R . . . .
C51 C 0.4475(3) 0.0166(4) 0.8906(3) 0.0289(7) Uani 1 1 d . . . . .
H51 H 0.372389 -0.036820 0.920106 0.042(11) Uiso 1 1 calc R . . . .
C52 C 0.4880(4) -0.0386(4) 0.7913(3) 0.0282(7) Uani 1 1 d . . . . .
H52 H 0.442885 -0.131935 0.753167 0.023(9) Uiso 1 1 calc R . . . .
C53 C 0.5946(3) 0.0420(3) 0.7467(2) 0.0222(5) Uani 1 1 d . . . . .
H53 H 0.621104 0.003178 0.678080 0.027(9) Uiso 1 1 calc R . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.481(3) . ?
C1 C9 1.517(4) . ?
C1 C10 1.536(3) . ?
C1 C2 1.570(3) . ?
O1 C8 1.375(3) . ?
C2 C3 1.500(4) . ?
C2 C18 1.509(4) . ?
C2 H2 1.0000 . ?
C3 C8 1.389(4) . ?
C3 C4 1.389(5) . ?
C4 C5 1.382(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(4) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.511(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O11 1.229(4) . ?
C11 N11 1.355(4) . ?
N11 C12 1.416(3) . ?
N11 H11 0.8800 . ?
C12 C17 1.389(4) . ?
C12 C13 1.392(3) . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(5) . ?
C15 I15 2.100(2) . ?
C16 C17 1.399(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.393(4) . ?
C18 C19 1.395(4) . ?
C19 C20 1.391(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C31 O31 1.479(3) . ?
C31 C39 1.522(4) . ?
C31 C40 1.535(3) . ?
C31 C32 1.568(3) . ?
O31 C38 1.378(4) . ?
C32 C33 1.506(4) . ?
C32 C48 1.508(4) . ?
C32 H32 1.0000 . ?
C33 C34 1.386(5) . ?
C33 C38 1.388(4) . ?
C34 C35 1.380(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.392(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.396(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.384(4) . ?
C37 H37 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.511(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 O41 1.227(4) . ?
C41 N41 1.357(4) . ?
N41 C42 1.412(3) . ?
N41 H41 0.8800 . ?
C42 C43 1.393(4) . ?
C42 C47 1.396(3) . ?
C43 C44 1.383(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.389(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.390(4) . ?
C45 I45 2.098(3) . ?
C46 C47 1.392(4) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 C53 1.393(4) . ?
C48 C49 1.396(4) . ?
C49 C50 1.388(5) . ?
C49 H49 0.9500 . ?
C50 C51 1.380(5) . ?
C50 H50 0.9500 . ?
C51 C52 1.380(5) . ?
C51 H51 0.9500 . ?
C52 C53 1.391(4) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?

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
O1 C1 C9 106.7(2) . . ?
O1 C1 C10 107.63(19) . . ?
C9 C1 C10 113.7(2) . . ?
O1 C1 C2 104.29(19) . . ?
C9 C1 C2 114.0(2) . . ?
C10 C1 C2 109.9(2) . . ?
C8 O1 C1 107.1(2) . . ?
C3 C2 C18 115.2(2) . . ?
C3 C2 C1 101.29(19) . . ?
C18 C2 C1 118.1(2) . . ?
C3 C2 H2 107.2 . . ?
C18 C2 H2 107.2 . . ?
C1 C2 H2 107.2 . . ?
C8 C3 C4 119.9(3) . . ?
C8 C3 C2 108.7(2) . . ?
C4 C3 C2 131.3(3) . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 117.1(3) . . ?
C8 C7 H7 121.4 . . ?
C6 C7 H7 121.4 . . ?
O1 C8 C7 125.3(3) . . ?
O1 C8 C3 112.8(2) . . ?
C7 C8 C3 121.9(3) . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 114.1(2) . . ?
C11 C10 H10A 108.7 . . ?
C1 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C1 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
O11 C11 N11 123.5(3) . . ?
O11 C11 C10 121.1(3) . . ?
N11 C11 C10 115.4(2) . . ?
C11 N11 C12 125.9(2) . . ?
C11 N11 H11 117.0 . . ?
C12 N11 H11 117.0 . . ?
C17 C12 C13 119.9(3) . . ?
C17 C12 N11 122.0(3) . . ?
C13 C12 N11 118.1(2) . . ?
C14 C13 C12 120.6(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.2(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 I15 118.3(2) . . ?
C14 C15 I15 121.12(19) . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 119.4(3) . . ?
C12 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C23 C18 C19 118.7(3) . . ?
C23 C18 C2 121.2(2) . . ?
C19 C18 C2 119.9(3) . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 119.6(4) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C18 121.1(3) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?
O31 C31 C39 106.3(2) . . ?
O31 C31 C40 108.4(2) . . ?
C39 C31 C40 114.0(2) . . ?
O31 C31 C32 103.13(19) . . ?
C39 C31 C32 114.0(2) . . ?
C40 C31 C32 110.3(2) . . ?
C38 O31 C31 106.6(2) . . ?
C33 C32 C48 117.1(2) . . ?
C33 C32 C31 100.8(2) . . ?
C48 C32 C31 117.9(2) . . ?
C33 C32 H32 106.7 . . ?
C48 C32 H32 106.7 . . ?
C31 C32 H32 106.7 . . ?
C34 C33 C38 119.9(3) . . ?
C34 C33 C32 132.2(3) . . ?
C38 C33 C32 107.6(2) . . ?
C35 C34 C33 119.1(4) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 120.4(3) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C37 121.3(3) . . ?
C35 C36 H36 119.3 . . ?
C37 C36 H36 119.3 . . ?
C38 C37 C36 117.0(3) . . ?
C38 C37 H37 121.5 . . ?
C36 C37 H37 121.5 . . ?
O31 C38 C37 124.8(3) . . ?
O31 C38 C33 112.9(3) . . ?
C37 C38 C33 122.2(3) . . ?
C31 C39 H39A 109.5 . . ?
C31 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C31 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 C31 114.7(2) . . ?
C41 C40 H40A 108.6 . . ?
C31 C40 H40A 108.6 . . ?
C41 C40 H40B 108.6 . . ?
C31 C40 H40B 108.6 . . ?
H40A C40 H40B 107.6 . . ?
O41 C41 N41 123.3(3) . . ?
O41 C41 C40 120.9(3) . . ?
N41 C41 C40 115.8(2) . . ?
C41 N41 C42 126.5(2) . . ?
C41 N41 H41 116.7 . . ?
C42 N41 H41 116.7 . . ?
C43 C42 C47 119.2(3) . . ?
C43 C42 N41 123.2(3) . . ?
C47 C42 N41 117.5(2) . . ?
C44 C43 C42 120.3(3) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C43 C44 C45 120.3(3) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
C44 C45 C46 120.2(3) . . ?
C44 C45 I45 118.5(2) . . ?
C46 C45 I45 121.30(19) . . ?
C45 C46 C47 119.5(2) . . ?
C45 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
C46 C47 C42 120.6(2) . . ?
C46 C47 H47 119.7 . . ?
C42 C47 H47 119.7 . . ?
C53 C48 C49 118.0(3) . . ?
C53 C48 C32 119.0(2) . . ?
C49 C48 C32 123.0(2) . . ?
C50 C49 C48 120.8(3) . . ?
C50 C49 H49 119.6 . . ?
C48 C49 H49 119.6 . . ?
C51 C50 C49 120.5(3) . . ?
C51 C50 H50 119.7 . . ?
C49 C50 H50 119.7 . . ?
C52 C51 C50 119.4(3) . . ?
C52 C51 H51 120.3 . . ?
C50 C51 H51 120.3 . . ?
C51 C52 C53 120.3(3) . . ?
C51 C52 H52 119.9 . . ?
C53 C52 H52 119.9 . . ?
C52 C53 C48 121.0(3) . . ?
C52 C53 H53 119.5 . . ?
C48 C53 H53 119.5 . . ?

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
C9 C1 O1 C8 98.6(2) . . . . ?
C10 C1 O1 C8 -139.1(2) . . . . ?
C2 C1 O1 C8 -22.4(3) . . . . ?
O1 C1 C2 C3 23.0(2) . . . . ?
C9 C1 C2 C3 -93.0(2) . . . . ?
C10 C1 C2 C3 138.1(2) . . . . ?
O1 C1 C2 C18 149.7(2) . . . . ?
C9 C1 C2 C18 33.8(3) . . . . ?
C10 C1 C2 C18 -95.2(3) . . . . ?
C18 C2 C3 C8 -144.9(2) . . . . ?
C1 C2 C3 C8 -16.3(3) . . . . ?
C18 C2 C3 C4 40.0(4) . . . . ?
C1 C2 C3 C4 168.6(3) . . . . ?
C8 C3 C4 C5 0.0(5) . . . . ?
C2 C3 C4 C5 174.7(3) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C4 C5 C6 C7 1.9(4) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C1 O1 C8 C7 -169.3(3) . . . . ?
C1 O1 C8 C3 12.9(3) . . . . ?
C6 C7 C8 O1 -178.0(3) . . . . ?
C6 C7 C8 C3 -0.5(4) . . . . ?
C4 C3 C8 O1 178.8(3) . . . . ?
C2 C3 C8 O1 3.0(3) . . . . ?
C4 C3 C8 C7 0.9(4) . . . . ?
C2 C3 C8 C7 -174.8(3) . . . . ?
O1 C1 C10 C11 -78.3(3) . . . . ?
C9 C1 C10 C11 39.6(3) . . . . ?
C2 C1 C10 C11 168.7(2) . . . . ?
C1 C10 C11 O11 -84.5(3) . . . . ?
C1 C10 C11 N11 94.4(3) . . . . ?
O11 C11 N11 C12 3.2(4) . . . . ?
C10 C11 N11 C12 -175.7(2) . . . . ?
C11 N11 C12 C17 28.2(4) . . . . ?
C11 N11 C12 C13 -154.0(3) . . . . ?
C17 C12 C13 C14 -1.3(4) . . . . ?
N11 C12 C13 C14 -179.1(2) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C13 C14 C15 I15 -179.65(19) . . . . ?
C14 C15 C16 C17 -0.9(5) . . . . ?
I15 C15 C16 C17 178.8(3) . . . . ?
C13 C12 C17 C16 0.4(5) . . . . ?
N11 C12 C17 C16 178.2(3) . . . . ?
C15 C16 C17 C12 0.7(5) . . . . ?
C3 C2 C18 C23 38.7(4) . . . . ?
C1 C2 C18 C23 -81.0(3) . . . . ?
C3 C2 C18 C19 -136.4(3) . . . . ?
C1 C2 C18 C19 103.9(3) . . . . ?
C23 C18 C19 C20 -0.1(4) . . . . ?
C2 C18 C19 C20 175.1(3) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C22 0.2(5) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
C21 C22 C23 C18 0.6(5) . . . . ?
C19 C18 C23 C22 -0.3(4) . . . . ?
C2 C18 C23 C22 -175.4(3) . . . . ?
C39 C31 O31 C38 93.0(2) . . . . ?
C40 C31 O31 C38 -144.1(2) . . . . ?
C32 C31 O31 C38 -27.2(2) . . . . ?
O31 C31 C32 C33 28.9(2) . . . . ?
C39 C31 C32 C33 -85.9(2) . . . . ?
C40 C31 C32 C33 144.4(2) . . . . ?
O31 C31 C32 C48 157.6(2) . . . . ?
C39 C31 C32 C48 42.8(3) . . . . ?
C40 C31 C32 C48 -86.9(3) . . . . ?
C48 C32 C33 C34 36.4(4) . . . . ?
C31 C32 C33 C34 165.7(3) . . . . ?
C48 C32 C33 C38 -150.5(2) . . . . ?
C31 C32 C33 C38 -21.3(3) . . . . ?
C38 C33 C34 C35 0.2(5) . . . . ?
C32 C33 C34 C35 172.5(3) . . . . ?
C33 C34 C35 C36 -1.8(5) . . . . ?
C34 C35 C36 C37 1.7(5) . . . . ?
C35 C36 C37 C38 0.1(4) . . . . ?
C31 O31 C38 C37 -167.8(3) . . . . ?
C31 O31 C38 C33 14.6(3) . . . . ?
C36 C37 C38 O31 -179.2(3) . . . . ?
C36 C37 C38 C33 -1.8(4) . . . . ?
C34 C33 C38 O31 179.4(3) . . . . ?
C32 C33 C38 O31 5.3(3) . . . . ?
C34 C33 C38 C37 1.7(5) . . . . ?
C32 C33 C38 C37 -172.4(3) . . . . ?
O31 C31 C40 C41 -82.2(3) . . . . ?
C39 C31 C40 C41 35.9(3) . . . . ?
C32 C31 C40 C41 165.6(2) . . . . ?
C31 C40 C41 O41 -81.9(3) . . . . ?
C31 C40 C41 N41 97.5(3) . . . . ?
O41 C41 N41 C42 3.6(5) . . . . ?
C40 C41 N41 C42 -175.8(2) . . . . ?
C41 N41 C42 C43 21.4(4) . . . . ?
C41 N41 C42 C47 -160.9(3) . . . . ?
C47 C42 C43 C44 0.6(5) . . . . ?
N41 C42 C43 C44 178.3(3) . . . . ?
C42 C43 C44 C45 0.1(5) . . . . ?
C43 C44 C45 C46 -0.5(5) . . . . ?
C43 C44 C45 I45 178.2(3) . . . . ?
C44 C45 C46 C47 0.1(4) . . . . ?
I45 C45 C46 C47 -178.50(19) . . . . ?
C45 C46 C47 C42 0.6(4) . . . . ?
C43 C42 C47 C46 -1.0(4) . . . . ?
N41 C42 C47 C46 -178.8(2) . . . . ?
C33 C32 C48 C53 -131.4(3) . . . . ?
C31 C32 C48 C53 108.0(3) . . . . ?
C33 C32 C48 C49 46.2(3) . . . . ?
C31 C32 C48 C49 -74.4(3) . . . . ?
C53 C48 C49 C50 -1.9(4) . . . . ?
C32 C48 C49 C50 -179.6(3) . . . . ?
C48 C49 C50 C51 0.3(5) . . . . ?
C49 C50 C51 C52 1.6(5) . . . . ?
C50 C51 C52 C53 -2.0(5) . . . . ?
C51 C52 C53 C48 0.3(5) . . . . ?
C49 C48 C53 C52 1.6(4) . . . . ?
C32 C48 C53 C52 179.3(3) . . . . ?

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
N41 H41 O11 0.88 2.01 2.860(3) 162. 1_655 yes
N11 H11 O41 0.88 2.06 2.890(3) 156. . yes
C13 H13 O41 0.95 2.57 3.320(3) 136. . yes
C17 H17 O11 0.95 2.34 2.858(5) 114. . yes
N41 H41 O11 0.88 2.01 2.860(3) 162. 1_655 yes
C43 H43 O41 0.95 2.30 2.852(4) 117. . yes

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_JF2920F
_database_code_depnum_ccdc_archive 'CCDC 2096011'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1-hydroxy-N-(4-((2R,3S)-2-methyl-2-phenyl-2,3-dihydrobenzofurna-3-yl)benzyl)-2-napthamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 N O3'
_chemical_formula_sum            'C33 H27 N O3'
_chemical_formula_weight         485.55

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'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.3151(4)
_cell_length_b                   11.1980(7)
_cell_length_c                   17.7567(10)
_cell_angle_alpha                85.4422(16)
_cell_angle_beta                 85.4490(17)
_cell_angle_gamma                86.8128(17)
_cell_volume                     1246.24(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9992
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      69.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.491
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.653
_shelx_estimated_absorpt_T_min   0.740
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7714
_exptl_absorpt_correction_T_max  0.8692
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20993
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.503
_diffrn_reflns_theta_max         69.434
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 0.909
_reflns_number_total             8303
_reflns_number_gt                8280
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_max     0.834
_reflns_Friedel_fraction_full    0.862

_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       'Apex2 (2014.9-1) (Bruker, 2014)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.1182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3857 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(8)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         8303
_refine_ls_number_parameters     883
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9249(4) 0.29140(19) 0.92069(11) 0.0278(4) Uani 1 1 d . . . . .
O1 O 1.1134(3) 0.24106(14) 0.95709(9) 0.0354(4) Uani 1 1 d . . . . .
C2 C 0.8885(4) 0.20479(18) 0.85591(11) 0.0263(4) Uani 1 1 d . . . . .
H2 H 0.742(4) 0.176(2) 0.8672(14) 0.025(6) Uiso 1 1 d . . . . .
C3 C 1.0528(4) 0.10485(18) 0.87164(11) 0.0268(4) Uani 1 1 d . . . . .
C4 C 1.1002(4) -0.00181(19) 0.83742(12) 0.0329(5) Uani 1 1 d . . . . .
H4 H 1.016(4) -0.023(2) 0.7939(16) 0.031(6) Uiso 1 1 d . . . . .
C5 C 1.2670(4) -0.0776(2) 0.86246(13) 0.0367(5) Uani 1 1 d . . . . .
H5 H 1.305(5) -0.152(3) 0.839(2) 0.052(9) Uiso 1 1 d . . . . .
C6 C 1.3829(4) -0.0479(2) 0.92100(13) 0.0349(5) Uani 1 1 d . . . . .
H6 H 1.497(5) -0.106(3) 0.9396(16) 0.036(7) Uiso 1 1 d . . . . .
C7 C 1.3367(4) 0.05838(19) 0.95573(13) 0.0333(5) Uani 1 1 d . . . . .
H7 H 1.424(5) 0.082(3) 0.9955(18) 0.045(8) Uiso 1 1 d . . . . .
C8 C 1.1721(4) 0.13279(19) 0.92941(12) 0.0295(4) Uani 1 1 d . . . . .
C9 C 0.9747(4) 0.41753(19) 0.89002(11) 0.0302(5) Uani 1 1 d . . . . .
C10 C 1.1788(5) 0.4427(2) 0.86035(13) 0.0414(6) Uani 1 1 d . . . . .
H10 H 1.289(6) 0.377(3) 0.867(2) 0.051(9) Uiso 1 1 d . . . . .
C11 C 1.2211(7) 0.5542(3) 0.82450(16) 0.0625(10) Uani 1 1 d . . . . .
H11 H 1.375(8) 0.569(5) 0.802(3) 0.093(15) Uiso 1 1 d . . . . .
C12 C 1.0633(7) 0.6421(3) 0.81749(18) 0.0694(12) Uani 1 1 d . . . . .
H12 H 1.089(7) 0.722(4) 0.792(2) 0.071(11) Uiso 1 1 d . . . . .
C13 C 0.8599(7) 0.6204(3) 0.84861(18) 0.0633(10) Uani 1 1 d . . . . .
H13 H 0.735(7) 0.680(4) 0.845(2) 0.069(11) Uiso 1 1 d . . . . .
C14 C 0.8143(5) 0.5082(2) 0.88471(14) 0.0413(6) Uani 1 1 d . . . . .
H14 H 0.671(5) 0.489(3) 0.9062(17) 0.037(7) Uiso 1 1 d . . . . .
C15 C 0.7408(4) 0.2861(2) 0.98130(13) 0.0383(5) Uani 1 1 d . . . . .
H15A H 0.731(5) 0.202(3) 1.0030(19) 0.045(8) Uiso 1 1 d . . . . .
H15B H 0.604(6) 0.314(3) 0.957(2) 0.050(9) Uiso 1 1 d . . . . .
H15C H 0.765(5) 0.336(3) 1.024(2) 0.047(8) Uiso 1 1 d . . . . .
C16 C 0.9057(3) 0.26360(18) 0.77591(11) 0.0252(4) Uani 1 1 d . . . . .
C17 C 0.7281(4) 0.32513(19) 0.74679(12) 0.0289(4) Uani 1 1 d . . . . .
H17 H 0.586(5) 0.326(2) 0.7790(16) 0.034(7) Uiso 1 1 d . . . . .
C18 C 0.7417(4) 0.38819(18) 0.67614(12) 0.0296(4) Uani 1 1 d . . . . .
H18 H 0.616(5) 0.438(3) 0.6563(16) 0.035(7) Uiso 1 1 d . . . . .
C19 C 0.9333(3) 0.39098(17) 0.63206(11) 0.0255(4) Uani 1 1 d . . . . .
C20 C 1.1099(3) 0.32713(18) 0.66016(11) 0.0259(4) Uani 1 1 d . . . . .
H20 H 1.240(5) 0.325(2) 0.6274(16) 0.034(7) Uiso 1 1 d . . . . .
C21 C 1.0960(3) 0.26487(18) 0.73072(11) 0.0266(4) Uani 1 1 d . . . . .
H21 H 1.215(4) 0.219(2) 0.7491(15) 0.027(6) Uiso 1 1 d . . . . .
C22 C 0.9589(4) 0.46335(18) 0.55656(12) 0.0280(4) Uani 1 1 d . . . . .
H22A H 0.984(5) 0.550(3) 0.5650(16) 0.034(7) Uiso 1 1 d . . . . .
H22B H 1.087(4) 0.430(2) 0.5282(14) 0.023(6) Uiso 1 1 d . . . . .
N22 N 0.7764(3) 0.46432(15) 0.51099(9) 0.0255(4) Uani 1 1 d . . . . .
H22 H 0.703(5) 0.535(3) 0.5023(16) 0.035(7) Uiso 1 1 d . . . . .
C23 C 0.7299(3) 0.36516(16) 0.47966(10) 0.0225(4) Uani 1 1 d . . . . .
O23 O 0.8430(2) 0.27041(12) 0.49076(8) 0.0267(3) Uani 1 1 d . . . . .
C24 C 0.5454(3) 0.36676(17) 0.43354(10) 0.0231(4) Uani 1 1 d . . . . .
C25 C 0.4915(3) 0.25894(16) 0.40735(10) 0.0223(4) Uani 1 1 d . . . . .
O25 O 0.6097(2) 0.15635(12) 0.42089(8) 0.0266(3) Uani 1 1 d . . . . .
H25A H 0.723(6) 0.181(3) 0.4493(19) 0.047(8) Uiso 1 1 d . . . . .
C26 C 0.3082(3) 0.25406(18) 0.36596(11) 0.0240(4) Uani 1 1 d . . . . .
C27 C 0.2426(3) 0.14484(19) 0.34215(12) 0.0270(4) Uani 1 1 d . . . . .
H27 H 0.330(5) 0.075(3) 0.3533(17) 0.040(7) Uiso 1 1 d . . . . .
C28 C 0.0624(4) 0.14300(19) 0.30445(12) 0.0302(4) Uani 1 1 d . . . . .
H28 H 0.021(5) 0.069(3) 0.2883(17) 0.036(7) Uiso 1 1 d . . . . .
C29 C -0.0587(4) 0.2502(2) 0.28723(12) 0.0299(4) Uani 1 1 d . . . . .
H29 H -0.188(4) 0.250(2) 0.2611(15) 0.025(6) Uiso 1 1 d . . . . .
C30 C 0.0037(4) 0.35711(19) 0.30846(11) 0.0287(4) Uani 1 1 d . . . . .
H30 H -0.088(4) 0.432(2) 0.2956(15) 0.029(6) Uiso 1 1 d . . . . .
C31 C 0.1863(3) 0.36196(18) 0.34901(10) 0.0241(4) Uani 1 1 d . . . . .
C32 C 0.2494(4) 0.47175(18) 0.37336(11) 0.0274(4) Uani 1 1 d . . . . .
H32 H 0.169(5) 0.546(2) 0.3610(16) 0.032(6) Uiso 1 1 d . . . . .
C33 C 0.4210(3) 0.47344(17) 0.41471(11) 0.0255(4) Uani 1 1 d . . . . .
H33 H 0.461(5) 0.547(3) 0.4329(16) 0.033(7) Uiso 1 1 d . . . . .
C41 C 0.7684(3) 0.74824(18) 0.07096(11) 0.0252(4) Uani 1 1 d . . . . .
O41 O 0.6018(2) 0.70578(13) 0.02773(8) 0.0274(3) Uani 1 1 d . . . . .
C42 C 0.7997(3) 0.64681(18) 0.13803(11) 0.0249(4) Uani 1 1 d . . . . .
H42 H 0.942(4) 0.603(2) 0.1230(14) 0.022(6) Uiso 1 1 d . . . . .
C43 C 0.6206(3) 0.56709(17) 0.13018(11) 0.0248(4) Uani 1 1 d . . . . .
C44 C 0.5464(4) 0.46806(18) 0.17489(12) 0.0290(4) Uani 1 1 d . . . . .
H44 H 0.606(4) 0.446(2) 0.2253(15) 0.026(6) Uiso 1 1 d . . . . .
C45 C 0.3831(4) 0.40545(19) 0.15042(13) 0.0323(5) Uani 1 1 d . . . . .
H45 H 0.333(5) 0.338(3) 0.1813(16) 0.033(7) Uiso 1 1 d . . . . .
C46 C 0.2978(4) 0.4401(2) 0.08176(13) 0.0321(5) Uani 1 1 d . . . . .
H46 H 0.181(5) 0.393(3) 0.0636(18) 0.046(8) Uiso 1 1 d . . . . .
C47 C 0.3673(4) 0.54022(18) 0.03727(12) 0.0288(4) Uani 1 1 d . . . . .
H47 H 0.308(5) 0.565(3) -0.0107(17) 0.036(7) Uiso 1 1 d . . . . .
C48 C 0.5253(3) 0.60333(18) 0.06392(11) 0.0253(4) Uani 1 1 d . . . . .
C49 C 0.6903(3) 0.86746(17) 0.10006(10) 0.0250(4) Uani 1 1 d . . . . .
C50 C 0.4786(4) 0.88646(19) 0.12609(12) 0.0295(4) Uani 1 1 d . . . . .
H50 H 0.376(4) 0.827(2) 0.1202(14) 0.024(6) Uiso 1 1 d . . . . .
C51 C 0.4097(4) 0.9901(2) 0.16045(13) 0.0360(5) Uani 1 1 d . . . . .
H51 H 0.261(5) 0.998(3) 0.1779(17) 0.039(7) Uiso 1 1 d . . . . .
C52 C 0.5519(5) 1.0769(2) 0.16835(14) 0.0402(6) Uani 1 1 d . . . . .
H52 H 0.509(6) 1.148(4) 0.193(2) 0.066(11) Uiso 1 1 d . . . . .
C53 C 0.7612(4) 1.0608(2) 0.14070(13) 0.0383(5) Uani 1 1 d . . . . .
H53 H 0.870(5) 1.125(3) 0.1462(18) 0.046(8) Uiso 1 1 d . . . . .
C54 C 0.8309(4) 0.9567(2) 0.10720(12) 0.0316(5) Uani 1 1 d . . . . .
H54 H 0.984(5) 0.946(3) 0.0851(17) 0.039(7) Uiso 1 1 d . . . . .
C55 C 0.9642(4) 0.7565(2) 0.01609(12) 0.0325(5) Uani 1 1 d . . . . .
H55A H 0.987(4) 0.678(3) -0.0022(16) 0.031(6) Uiso 1 1 d . . . . .
H55B H 1.094(5) 0.772(3) 0.0445(18) 0.047(8) Uiso 1 1 d . . . . .
H55C H 0.940(4) 0.822(2) -0.0234(16) 0.032(6) Uiso 1 1 d . . . . .
C56 C 0.8128(3) 0.69309(16) 0.21556(11) 0.0231(4) Uani 1 1 d . . . . .
C57 C 0.6341(3) 0.70651(18) 0.26570(11) 0.0250(4) Uani 1 1 d . . . . .
H57 H 0.499(5) 0.680(2) 0.2517(16) 0.035(7) Uiso 1 1 d . . . . .
C58 C 0.6468(3) 0.75412(18) 0.33491(12) 0.0264(4) Uani 1 1 d . . . . .
H58 H 0.519(5) 0.767(2) 0.3685(16) 0.031(6) Uiso 1 1 d . . . . .
C59 C 0.8392(3) 0.78974(16) 0.35642(11) 0.0244(4) Uani 1 1 d . . . . .
C60 C 1.0192(3) 0.77628(17) 0.30632(12) 0.0259(4) Uani 1 1 d . . . . .
H60 H 1.156(5) 0.803(2) 0.3210(15) 0.033(7) Uiso 1 1 d . . . . .
C61 C 1.0061(3) 0.72751(17) 0.23737(11) 0.0257(4) Uani 1 1 d . . . . .
H61 H 1.135(5) 0.714(3) 0.2033(17) 0.037(7) Uiso 1 1 d . . . . .
C62 C 0.8598(4) 0.83663(19) 0.43318(12) 0.0276(4) Uani 1 1 d . . . . .
H62A H 0.909(4) 0.777(2) 0.4658(14) 0.017(5) Uiso 1 1 d . . . . .
H62B H 0.963(4) 0.902(2) 0.4287(14) 0.026(6) Uiso 1 1 d . . . . .
N62 N 0.6601(3) 0.88425(15) 0.46887(10) 0.0260(4) Uani 1 1 d . . . . .
H62 H 0.618(4) 0.959(3) 0.4581(15) 0.026(6) Uiso 1 1 d . . . . .
C63 C 0.5270(3) 0.81520(17) 0.51334(11) 0.0246(4) Uani 1 1 d . . . . .
O63 O 0.5682(3) 0.70398(12) 0.52362(8) 0.0289(3) Uani 1 1 d . . . . .
C64 C 0.3315(3) 0.87236(17) 0.54858(11) 0.0244(4) Uani 1 1 d . . . . .
C65 C 0.1884(3) 0.80180(17) 0.59327(11) 0.0252(4) Uani 1 1 d . . . . .
O65 O 0.2253(3) 0.68268(12) 0.60819(9) 0.0317(3) Uani 1 1 d . . . . .
H65A H 0.354(5) 0.669(3) 0.5803(19) 0.042(8) Uiso 1 1 d . . . . .
C66 C -0.0059(4) 0.85305(19) 0.62606(11) 0.0272(4) Uani 1 1 d . . . . .
C67 C -0.1594(4) 0.7820(2) 0.66807(12) 0.0327(5) Uani 1 1 d . . . . .
H67 H -0.127(5) 0.694(3) 0.6763(16) 0.037(7) Uiso 1 1 d . . . . .
C68 C -0.3440(4) 0.8348(2) 0.69833(13) 0.0378(5) Uani 1 1 d . . . . .
H68 H -0.447(5) 0.786(3) 0.7257(17) 0.039(7) Uiso 1 1 d . . . . .
C69 C -0.3835(4) 0.9599(2) 0.68888(13) 0.0374(5) Uani 1 1 d . . . . .
H69 H -0.525(5) 0.990(3) 0.7104(18) 0.044(8) Uiso 1 1 d . . . . .
C70 C -0.2393(4) 1.0305(2) 0.64799(12) 0.0333(5) Uani 1 1 d . . . . .
H70 H -0.268(4) 1.119(3) 0.6408(16) 0.032(6) Uiso 1 1 d . . . . .
C71 C -0.0475(4) 0.97935(18) 0.61464(11) 0.0282(4) Uani 1 1 d . . . . .
C72 C 0.1021(4) 1.05026(18) 0.57021(12) 0.0294(4) Uani 1 1 d . . . . .
H72 H 0.065(5) 1.136(3) 0.5649(17) 0.038(7) Uiso 1 1 d . . . . .
C73 C 0.2827(4) 0.99839(17) 0.53805(11) 0.0264(4) Uani 1 1 d . . . . .
H73 H 0.386(4) 1.048(2) 0.5077(15) 0.028(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
C1 O1 1.464(3) . ?
C1 C9 1.513(3) . ?
C1 C15 1.521(3) . ?
C1 C2 1.600(3) . ?
O1 C8 1.366(3) . ?
C2 C3 1.508(3) . ?
C2 C16 1.516(3) . ?
C2 H2 1.00(3) . ?
C3 C8 1.384(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.393(3) . ?
C4 H4 1.02(3) . ?
C5 C6 1.389(4) . ?
C5 H5 0.97(4) . ?
C6 C7 1.390(3) . ?
C6 H6 1.00(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.99(3) . ?
C9 C10 1.388(4) . ?
C9 C14 1.397(3) . ?
C10 C11 1.385(4) . ?
C10 H10 1.00(4) . ?
C11 C12 1.367(6) . ?
C11 H11 1.04(5) . ?
C12 C13 1.384(6) . ?
C12 H12 0.98(4) . ?
C13 C14 1.398(4) . ?
C13 H13 1.01(4) . ?
C14 H14 0.98(3) . ?
C15 H15A 0.99(3) . ?
C15 H15B 1.02(4) . ?
C15 H15C 1.00(3) . ?
C16 C21 1.391(3) . ?
C16 C17 1.396(3) . ?
C17 C18 1.389(3) . ?
C17 H17 1.03(3) . ?
C18 C19 1.389(3) . ?
C18 H18 1.02(3) . ?
C19 C20 1.395(3) . ?
C19 C22 1.512(3) . ?
C20 C21 1.383(3) . ?
C20 H20 0.97(3) . ?
C21 H21 0.95(3) . ?
C22 N22 1.459(3) . ?
C22 H22A 1.02(3) . ?
C22 H22B 0.99(3) . ?
N22 C23 1.338(3) . ?
N22 H22 0.90(3) . ?
C23 O23 1.257(2) . ?
C23 C24 1.475(3) . ?
C24 C25 1.396(3) . ?
C24 C33 1.425(3) . ?
C25 O25 1.351(2) . ?
C25 C26 1.425(3) . ?
O25 H25A 0.97(4) . ?
C26 C27 1.419(3) . ?
C26 C31 1.421(3) . ?
C27 C28 1.367(3) . ?
C27 H27 0.95(3) . ?
C28 C29 1.412(3) . ?
C28 H28 0.95(3) . ?
C29 C30 1.371(3) . ?
C29 H29 0.97(3) . ?
C30 C31 1.413(3) . ?
C30 H30 1.01(3) . ?
C31 C32 1.422(3) . ?
C32 C33 1.358(3) . ?
C32 H32 0.97(3) . ?
C33 H33 0.96(3) . ?
C41 O41 1.471(2) . ?
C41 C49 1.513(3) . ?
C41 C55 1.515(3) . ?
C41 C42 1.595(3) . ?
O41 C48 1.363(3) . ?
C42 C43 1.501(3) . ?
C42 C56 1.519(3) . ?
C42 H42 1.03(3) . ?
C43 C48 1.386(3) . ?
C43 C44 1.392(3) . ?
C44 C45 1.394(3) . ?
C44 H44 1.01(3) . ?
C45 C46 1.390(3) . ?
C45 H45 0.95(3) . ?
C46 C47 1.390(3) . ?
C46 H46 1.02(3) . ?
C47 C48 1.388(3) . ?
C47 H47 0.97(3) . ?
C49 C50 1.390(3) . ?
C49 C54 1.393(3) . ?
C50 C51 1.386(3) . ?
C50 H50 0.98(3) . ?
C51 C52 1.382(4) . ?
C51 H51 0.96(3) . ?
C52 C53 1.381(4) . ?
C52 H52 0.96(4) . ?
C53 C54 1.384(3) . ?
C53 H53 1.03(3) . ?
C54 H54 1.02(3) . ?
C55 H55A 0.96(3) . ?
C55 H55B 1.03(3) . ?
C55 H55C 0.99(3) . ?
C56 C57 1.390(3) . ?
C56 C61 1.393(3) . ?
C57 C58 1.388(3) . ?
C57 H57 0.98(3) . ?
C58 C59 1.390(3) . ?
C58 H58 0.97(3) . ?
C59 C60 1.396(3) . ?
C59 C62 1.517(3) . ?
C60 C61 1.390(3) . ?
C60 H60 0.99(3) . ?
C61 H61 0.99(3) . ?
C62 N62 1.459(3) . ?
C62 H62A 0.91(3) . ?
C62 H62B 1.00(3) . ?
N62 C63 1.341(3) . ?
N62 H62 0.88(3) . ?
C63 O63 1.260(2) . ?
C63 C64 1.476(3) . ?
C64 C65 1.391(3) . ?
C64 C73 1.428(3) . ?
C65 O65 1.350(2) . ?
C65 C66 1.427(3) . ?
O65 H65A 0.93(3) . ?
C66 C67 1.416(3) . ?
C66 C71 1.426(3) . ?
C67 C68 1.368(4) . ?
C67 H67 0.99(3) . ?
C68 C69 1.408(4) . ?
C68 H68 0.95(3) . ?
C69 C70 1.366(4) . ?
C69 H69 1.00(3) . ?
C70 C71 1.417(3) . ?
C70 H70 0.99(3) . ?
C71 C72 1.419(3) . ?
C72 C73 1.356(3) . ?
C72 H72 0.97(3) . ?
C73 H73 0.98(3) . ?

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
O1 C1 C9 106.48(17) . . ?
O1 C1 C15 106.49(18) . . ?
C9 C1 C15 113.79(19) . . ?
O1 C1 C2 106.00(16) . . ?
C9 C1 C2 113.26(16) . . ?
C15 C1 C2 110.21(18) . . ?
C8 O1 C1 108.90(16) . . ?
C3 C2 C16 114.95(17) . . ?
C3 C2 C1 101.12(16) . . ?
C16 C2 C1 114.90(16) . . ?
C3 C2 H2 110.9(15) . . ?
C16 C2 H2 108.5(15) . . ?
C1 C2 H2 106.1(15) . . ?
C8 C3 C4 119.3(2) . . ?
C8 C3 C2 109.76(18) . . ?
C4 C3 C2 131.0(2) . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 120.2(16) . . ?
C5 C4 H4 120.9(16) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 118(2) . . ?
C4 C5 H5 121(2) . . ?
C5 C6 C7 120.9(2) . . ?
C5 C6 H6 119.1(17) . . ?
C7 C6 H6 119.9(17) . . ?
C8 C7 C6 117.3(2) . . ?
C8 C7 H7 121.7(18) . . ?
C6 C7 H7 120.9(18) . . ?
O1 C8 C7 123.4(2) . . ?
O1 C8 C3 113.66(19) . . ?
C7 C8 C3 122.9(2) . . ?
C10 C9 C14 118.5(2) . . ?
C10 C9 C1 120.2(2) . . ?
C14 C9 C1 121.1(2) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 123(2) . . ?
C9 C10 H10 116(2) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 121(3) . . ?
C10 C11 H11 118(3) . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12 122(2) . . ?
C13 C12 H12 118(2) . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 124(2) . . ?
C14 C13 H13 116(2) . . ?
C9 C14 C13 120.0(3) . . ?
C9 C14 H14 117.5(17) . . ?
C13 C14 H14 122.4(17) . . ?
C1 C15 H15A 108.4(19) . . ?
C1 C15 H15B 108.7(19) . . ?
H15A C15 H15B 110(3) . . ?
C1 C15 H15C 111.2(19) . . ?
H15A C15 H15C 107(3) . . ?
H15B C15 H15C 111(3) . . ?
C21 C16 C17 117.61(19) . . ?
C21 C16 C2 122.64(19) . . ?
C17 C16 C2 119.66(18) . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.4(16) . . ?
C16 C17 H17 119.3(16) . . ?
C17 C18 C19 120.6(2) . . ?
C17 C18 H18 121.8(16) . . ?
C19 C18 H18 117.5(16) . . ?
C18 C19 C20 118.16(18) . . ?
C18 C19 C22 122.63(19) . . ?
C20 C19 C22 119.18(19) . . ?
C21 C20 C19 121.03(19) . . ?
C21 C20 H20 121.5(17) . . ?
C19 C20 H20 117.4(17) . . ?
C20 C21 C16 121.2(2) . . ?
C20 C21 H21 121.0(16) . . ?
C16 C21 H21 117.8(16) . . ?
N22 C22 C19 114.48(18) . . ?
N22 C22 H22A 107.4(16) . . ?
C19 C22 H22A 109.7(16) . . ?
N22 C22 H22B 109.6(15) . . ?
C19 C22 H22B 107.5(14) . . ?
H22A C22 H22B 108(2) . . ?
C23 N22 C22 120.43(17) . . ?
C23 N22 H22 121.8(19) . . ?
C22 N22 H22 117.6(19) . . ?
O23 C23 N22 119.40(19) . . ?
O23 C23 C24 120.42(17) . . ?
N22 C23 C24 120.17(17) . . ?
C25 C24 C33 118.97(18) . . ?
C25 C24 C23 118.30(17) . . ?
C33 C24 C23 122.72(17) . . ?
O25 C25 C24 121.24(18) . . ?
O25 C25 C26 118.08(16) . . ?
C24 C25 C26 120.68(17) . . ?
C25 O25 H25A 103.4(19) . . ?
C27 C26 C31 119.2(2) . . ?
C27 C26 C25 122.07(18) . . ?
C31 C26 C25 118.76(17) . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27 122.9(19) . . ?
C26 C27 H27 116.6(19) . . ?
C27 C28 C29 120.5(2) . . ?
C27 C28 H28 119.6(18) . . ?
C29 C28 H28 119.9(18) . . ?
C30 C29 C28 120.1(2) . . ?
C30 C29 H29 118.6(14) . . ?
C28 C29 H29 121.3(14) . . ?
C29 C30 C31 120.9(2) . . ?
C29 C30 H30 117.9(15) . . ?
C31 C30 H30 121.2(15) . . ?
C30 C31 C26 118.82(18) . . ?
C30 C31 C32 121.56(19) . . ?
C26 C31 C32 119.62(19) . . ?
C33 C32 C31 120.46(19) . . ?
C33 C32 H32 119.3(17) . . ?
C31 C32 H32 120.2(17) . . ?
C32 C33 C24 121.40(18) . . ?
C32 C33 H33 120.9(17) . . ?
C24 C33 H33 117.7(17) . . ?
O41 C41 C49 108.11(16) . . ?
O41 C41 C55 105.57(16) . . ?
C49 C41 C55 113.42(18) . . ?
O41 C41 C42 105.04(15) . . ?
C49 C41 C42 112.19(15) . . ?
C55 C41 C42 111.86(17) . . ?
C48 O41 C41 109.26(15) . . ?
C43 C42 C56 116.36(16) . . ?
C43 C42 C41 102.16(16) . . ?
C56 C42 C41 114.95(15) . . ?
C43 C42 H42 109.7(14) . . ?
C56 C42 H42 108.4(14) . . ?
C41 C42 H42 104.6(14) . . ?
C48 C43 C44 119.2(2) . . ?
C48 C43 C42 109.03(18) . . ?
C44 C43 C42 131.78(19) . . ?
C43 C44 C45 119.1(2) . . ?
C43 C44 H44 119.7(15) . . ?
C45 C44 H44 121.2(15) . . ?
C46 C45 C44 120.5(2) . . ?
C46 C45 H45 120.7(17) . . ?
C44 C45 H45 118.7(17) . . ?
C45 C46 C47 121.0(2) . . ?
C45 C46 H46 120.2(17) . . ?
C47 C46 H46 118.8(17) . . ?
C48 C47 C46 117.4(2) . . ?
C48 C47 H47 121.2(17) . . ?
C46 C47 H47 121.4(17) . . ?
O41 C48 C43 113.76(18) . . ?
O41 C48 C47 123.56(18) . . ?
C43 C48 C47 122.7(2) . . ?
C50 C49 C54 118.43(19) . . ?
C50 C49 C41 120.34(18) . . ?
C54 C49 C41 121.03(19) . . ?
C51 C50 C49 121.0(2) . . ?
C51 C50 H50 118.9(15) . . ?
C49 C50 H50 120.1(15) . . ?
C52 C51 C50 120.0(2) . . ?
C52 C51 H51 122.6(17) . . ?
C50 C51 H51 117.4(17) . . ?
C53 C52 C51 119.6(2) . . ?
C53 C52 H52 119(2) . . ?
C51 C52 H52 122(2) . . ?
C52 C53 C54 120.5(2) . . ?
C52 C53 H53 120.8(18) . . ?
C54 C53 H53 118.6(19) . . ?
C53 C54 C49 120.5(2) . . ?
C53 C54 H54 120.6(16) . . ?
C49 C54 H54 118.8(16) . . ?
C41 C55 H55A 105.0(16) . . ?
C41 C55 H55B 110.0(18) . . ?
H55A C55 H55B 107(2) . . ?
C41 C55 H55C 109.3(16) . . ?
H55A C55 H55C 115(2) . . ?
H55B C55 H55C 110(2) . . ?
C57 C56 C61 117.88(18) . . ?
C57 C56 C42 121.88(18) . . ?
C61 C56 C42 120.20(18) . . ?
C58 C57 C56 121.20(19) . . ?
C58 C57 H57 120.3(17) . . ?
C56 C57 H57 118.5(17) . . ?
C57 C58 C59 120.99(19) . . ?
C57 C58 H58 120.3(17) . . ?
C59 C58 H58 118.6(16) . . ?
C58 C59 C60 118.04(18) . . ?
C58 C59 C62 122.12(19) . . ?
C60 C59 C62 119.78(18) . . ?
C61 C60 C59 120.77(19) . . ?
C61 C60 H60 121.0(16) . . ?
C59 C60 H60 118.3(16) . . ?
C60 C61 C56 121.10(19) . . ?
C60 C61 H61 120.6(17) . . ?
C56 C61 H61 118.3(17) . . ?
N62 C62 C59 114.03(17) . . ?
N62 C62 H62A 106.5(15) . . ?
C59 C62 H62A 110.0(15) . . ?
N62 C62 H62B 107.2(15) . . ?
C59 C62 H62B 110.5(15) . . ?
H62A C62 H62B 108(2) . . ?
C63 N62 C62 122.49(17) . . ?
C63 N62 H62 117.5(17) . . ?
C62 N62 H62 119.8(17) . . ?
O63 C63 N62 120.22(19) . . ?
O63 C63 C64 121.32(18) . . ?
N62 C63 C64 118.45(17) . . ?
C65 C64 C73 118.49(19) . . ?
C65 C64 C63 119.36(17) . . ?
C73 C64 C63 122.15(18) . . ?
O65 C65 C64 122.35(19) . . ?
O65 C65 C66 116.63(18) . . ?
C64 C65 C66 121.02(18) . . ?
C65 O65 H65A 101.8(19) . . ?
C67 C66 C71 119.3(2) . . ?
C67 C66 C65 122.0(2) . . ?
C71 C66 C65 118.65(19) . . ?
C68 C67 C66 120.1(2) . . ?
C68 C67 H67 121.5(17) . . ?
C66 C67 H67 118.4(17) . . ?
C67 C68 C69 120.8(2) . . ?
C67 C68 H68 119.3(19) . . ?
C69 C68 H68 119.8(19) . . ?
C70 C69 C68 120.4(2) . . ?
C70 C69 H69 124.5(18) . . ?
C68 C69 H69 115.0(18) . . ?
C69 C70 C71 120.7(2) . . ?
C69 C70 H70 120.4(16) . . ?
C71 C70 H70 118.9(16) . . ?
C70 C71 C72 121.8(2) . . ?
C70 C71 C66 118.7(2) . . ?
C72 C71 C66 119.5(2) . . ?
C73 C72 C71 120.39(19) . . ?
C73 C72 H72 124.1(18) . . ?
C71 C72 H72 115.6(18) . . ?
C72 C73 C64 121.9(2) . . ?
C72 C73 H73 120.2(15) . . ?
C64 C73 H73 117.9(15) . . ?

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
C9 C1 O1 C8 -128.27(17) . . . . ?
C15 C1 O1 C8 110.0(2) . . . . ?
C2 C1 O1 C8 -7.4(2) . . . . ?
O1 C1 C2 C3 6.89(19) . . . . ?
C9 C1 C2 C3 123.28(19) . . . . ?
C15 C1 C2 C3 -108.0(2) . . . . ?
O1 C1 C2 C16 -117.53(19) . . . . ?
C9 C1 C2 C16 -1.1(3) . . . . ?
C15 C1 C2 C16 127.6(2) . . . . ?
C16 C2 C3 C8 120.11(19) . . . . ?
C1 C2 C3 C8 -4.3(2) . . . . ?
C16 C2 C3 C4 -58.2(3) . . . . ?
C1 C2 C3 C4 177.4(2) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C5 178.2(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C1 O1 C8 C7 -175.8(2) . . . . ?
C1 O1 C8 C3 5.0(2) . . . . ?
C6 C7 C8 O1 -178.3(2) . . . . ?
C6 C7 C8 C3 0.8(3) . . . . ?
C4 C3 C8 O1 178.49(19) . . . . ?
C2 C3 C8 O1 -0.1(2) . . . . ?
C4 C3 C8 C7 -0.7(3) . . . . ?
C2 C3 C8 C7 -179.31(19) . . . . ?
O1 C1 C9 C10 36.3(2) . . . . ?
C15 C1 C9 C10 153.3(2) . . . . ?
C2 C1 C9 C10 -79.8(2) . . . . ?
O1 C1 C9 C14 -149.40(19) . . . . ?
C15 C1 C9 C14 -32.4(3) . . . . ?
C2 C1 C9 C14 94.5(2) . . . . ?
C14 C9 C10 C11 -1.7(3) . . . . ?
C1 C9 C10 C11 172.7(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 1.9(4) . . . . ?
C11 C12 C13 C14 -2.2(4) . . . . ?
C10 C9 C14 C13 1.5(3) . . . . ?
C1 C9 C14 C13 -173.0(2) . . . . ?
C12 C13 C14 C9 0.5(4) . . . . ?
C3 C2 C16 C21 -25.8(3) . . . . ?
C1 C2 C16 C21 91.0(2) . . . . ?
C3 C2 C16 C17 157.83(18) . . . . ?
C1 C2 C16 C17 -85.4(2) . . . . ?
C21 C16 C17 C18 -1.7(3) . . . . ?
C2 C16 C17 C18 174.80(18) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 1.1(3) . . . . ?
C17 C18 C19 C22 -176.86(19) . . . . ?
C18 C19 C20 C21 -1.4(3) . . . . ?
C22 C19 C20 C21 176.62(18) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C17 C16 C21 C20 1.4(3) . . . . ?
C2 C16 C21 C20 -175.00(19) . . . . ?
C18 C19 C22 N22 -38.0(3) . . . . ?
C20 C19 C22 N22 144.08(18) . . . . ?
C19 C22 N22 C23 -70.0(2) . . . . ?
C22 N22 C23 O23 1.1(3) . . . . ?
C22 N22 C23 C24 -179.89(17) . . . . ?
O23 C23 C24 C25 4.5(3) . . . . ?
N22 C23 C24 C25 -174.53(17) . . . . ?
O23 C23 C24 C33 -175.43(17) . . . . ?
N22 C23 C24 C33 5.5(3) . . . . ?
C33 C24 C25 O25 177.12(17) . . . . ?
C23 C24 C25 O25 -2.8(3) . . . . ?
C33 C24 C25 C26 -3.4(3) . . . . ?
C23 C24 C25 C26 176.68(16) . . . . ?
O25 C25 C26 C27 3.0(3) . . . . ?
C24 C25 C26 C27 -176.50(18) . . . . ?
O25 C25 C26 C31 -177.87(16) . . . . ?
C24 C25 C26 C31 2.6(3) . . . . ?
C31 C26 C27 C28 -1.1(3) . . . . ?
C25 C26 C27 C28 178.08(18) . . . . ?
C26 C27 C28 C29 1.3(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C31 -1.3(3) . . . . ?
C29 C30 C31 C26 1.5(3) . . . . ?
C29 C30 C31 C32 -178.1(2) . . . . ?
C27 C26 C31 C30 -0.4(3) . . . . ?
C25 C26 C31 C30 -179.53(17) . . . . ?
C27 C26 C31 C32 179.29(18) . . . . ?
C25 C26 C31 C32 0.1(3) . . . . ?
C30 C31 C32 C33 177.52(19) . . . . ?
C26 C31 C32 C33 -2.1(3) . . . . ?
C31 C32 C33 C24 1.4(3) . . . . ?
C25 C24 C33 C32 1.4(3) . . . . ?
C23 C24 C33 C32 -178.69(18) . . . . ?
C49 C41 O41 C48 -114.88(17) . . . . ?
C55 C41 O41 C48 123.44(17) . . . . ?
C42 C41 O41 C48 5.1(2) . . . . ?
O41 C41 C42 C43 -7.96(19) . . . . ?
C49 C41 C42 C43 109.24(18) . . . . ?
C55 C41 C42 C43 -122.00(18) . . . . ?
O41 C41 C42 C56 -134.91(17) . . . . ?
C49 C41 C42 C56 -17.7(2) . . . . ?
C55 C41 C42 C56 111.1(2) . . . . ?
C56 C42 C43 C48 134.39(18) . . . . ?
C41 C42 C43 C48 8.3(2) . . . . ?
C56 C42 C43 C44 -47.6(3) . . . . ?
C41 C42 C43 C44 -173.7(2) . . . . ?
C48 C43 C44 C45 2.2(3) . . . . ?
C42 C43 C44 C45 -175.6(2) . . . . ?
C43 C44 C45 C46 1.1(3) . . . . ?
C44 C45 C46 C47 -2.4(3) . . . . ?
C45 C46 C47 C48 0.4(3) . . . . ?
C41 O41 C48 C43 0.3(2) . . . . ?
C41 O41 C48 C47 -179.53(18) . . . . ?
C44 C43 C48 O41 175.79(16) . . . . ?
C42 C43 C48 O41 -5.9(2) . . . . ?
C44 C43 C48 C47 -4.4(3) . . . . ?
C42 C43 C48 C47 173.85(18) . . . . ?
C46 C47 C48 O41 -177.16(18) . . . . ?
C46 C47 C48 C43 3.1(3) . . . . ?
O41 C41 C49 C50 38.8(2) . . . . ?
C55 C41 C49 C50 155.53(18) . . . . ?
C42 C41 C49 C50 -76.5(2) . . . . ?
O41 C41 C49 C54 -146.45(17) . . . . ?
C55 C41 C49 C54 -29.7(3) . . . . ?
C42 C41 C49 C54 98.2(2) . . . . ?
C54 C49 C50 C51 -1.9(3) . . . . ?
C41 C49 C50 C51 172.93(19) . . . . ?
C49 C50 C51 C52 0.8(3) . . . . ?
C50 C51 C52 C53 1.1(3) . . . . ?
C51 C52 C53 C54 -1.9(3) . . . . ?
C52 C53 C54 C49 0.8(3) . . . . ?
C50 C49 C54 C53 1.1(3) . . . . ?
C41 C49 C54 C53 -173.69(19) . . . . ?
C43 C42 C56 C57 -26.4(3) . . . . ?
C41 C42 C56 C57 92.9(2) . . . . ?
C43 C42 C56 C61 155.81(18) . . . . ?
C41 C42 C56 C61 -84.9(2) . . . . ?
C61 C56 C57 C58 0.8(3) . . . . ?
C42 C56 C57 C58 -176.97(18) . . . . ?
C56 C57 C58 C59 -0.2(3) . . . . ?
C57 C58 C59 C60 0.0(3) . . . . ?
C57 C58 C59 C62 -177.09(18) . . . . ?
C58 C59 C60 C61 -0.6(3) . . . . ?
C62 C59 C60 C61 176.55(18) . . . . ?
C59 C60 C61 C56 1.4(3) . . . . ?
C57 C56 C61 C60 -1.4(3) . . . . ?
C42 C56 C61 C60 176.41(17) . . . . ?
C58 C59 C62 N62 -22.5(3) . . . . ?
C60 C59 C62 N62 160.41(17) . . . . ?
C59 C62 N62 C63 88.3(2) . . . . ?
C62 N62 C63 O63 -2.5(3) . . . . ?
C62 N62 C63 C64 178.36(16) . . . . ?
O63 C63 C64 C65 -0.8(3) . . . . ?
N62 C63 C64 C65 178.27(17) . . . . ?
O63 C63 C64 C73 179.54(18) . . . . ?
N62 C63 C64 C73 -1.4(3) . . . . ?
C73 C64 C65 O65 -177.78(18) . . . . ?
C63 C64 C65 O65 2.6(3) . . . . ?
C73 C64 C65 C66 1.9(3) . . . . ?
C63 C64 C65 C66 -177.75(16) . . . . ?
O65 C65 C66 C67 -4.0(3) . . . . ?
C64 C65 C66 C67 176.28(18) . . . . ?
O65 C65 C66 C71 177.29(17) . . . . ?
C64 C65 C66 C71 -2.4(3) . . . . ?
C71 C66 C67 C68 -1.1(3) . . . . ?
C65 C66 C67 C68 -179.78(19) . . . . ?
C66 C67 C68 C69 -0.5(3) . . . . ?
C67 C68 C69 C70 1.2(4) . . . . ?
C68 C69 C70 C71 -0.2(4) . . . . ?
C69 C70 C71 C72 178.3(2) . . . . ?
C69 C70 C71 C66 -1.4(3) . . . . ?
C67 C66 C71 C70 2.1(3) . . . . ?
C65 C66 C71 C70 -179.22(18) . . . . ?
C67 C66 C71 C72 -177.64(19) . . . . ?
C65 C66 C71 C72 1.1(3) . . . . ?
C70 C71 C72 C73 -178.97(19) . . . . ?
C66 C71 C72 C73 0.7(3) . . . . ?
C71 C72 C73 C64 -1.3(3) . . . . ?
C65 C64 C73 C72 -0.1(3) . . . . ?
C63 C64 C73 C72 179.59(18) . . . . ?

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
C22 H22A O65 1.02(3) 2.39(3) 3.281(3) 145(2) 1_655 yes
N22 H22 O63 0.90(3) 2.08(3) 2.939(2) 158(3) . yes
O25 H25A O23 0.97(4) 1.55(3) 2.4680(19) 155(3) . yes
N62 H62 O25 0.88(3) 2.25(3) 3.104(2) 164(2) 1_565 yes
O65 H65A O63 0.93(3) 1.67(3) 2.547(2) 157(3) . yes

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.030



