#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:12:39 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272579 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/58/1565822.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1565822
loop_
_publ_author_name
'Dishman, Sarah N.'
'Laconsay, Croix J.'
'Fettinger, James C.'
'Tantillo, Dean J.'
'Shaw, Jared T.'
_publ_section_title
;
 Divergent stereochemical outcomes in the insertion of donor/donor
 carbenes into the C--H bonds of stereogenic centers
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1030
_journal_page_last               1036
_journal_paper_doi               10.1039/D1SC04622E
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H20 I N O2'
_chemical_formula_sum            'C23 H20 I N O2'
_chemical_formula_weight         469.30
_chemical_name_systematic
Trans-N-(4-iodophenyl)-2-2-methyl-3-phenyl-2,3-dihydrobenzofuran-2-yl)acetamide
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-12 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                99.2233(18)
_cell_angle_beta                 96.0361(18)
_cell_angle_gamma                91.1970(17)
_cell_formula_units_Z            2
_cell_length_a                   8.7754(5)
_cell_length_b                   8.8984(6)
_cell_length_c                   12.8772(8)
_cell_measurement_reflns_used    9172
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.68
_cell_measurement_theta_min      2.34
_cell_volume                     986.31(11)
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_collection       'Apex3 (2017.3) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Photon100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49290
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         2.336
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  0.8365
_exptl_absorpt_correction_T_min  0.7842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       Plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.056
_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)
_refine_ls_extinction_coef       0.0076(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         11503
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0194
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0165P)²+0.3992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0399
_refine_ls_wR_factor_ref         0.0408
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                10996
_reflns_number_total             11503
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04622e2.cif
_cod_data_source_block           JF2873FF
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1565821--1565823.cif.
;
_cod_database_code               1565822
_shelx_shelxl_version_number     2018/3
_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'
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 . . . .
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'
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_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_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
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) . . . . ?
