#------------------------------------------------------------------------------
#$Date: 2020-08-05 01:46:45 +0300 (Wed, 05 Aug 2020) $
#$Revision: 254800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/51/4135135.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_4135135
loop_
_publ_author_name
'Andres, Rémi'
'Wang, Qian'
'Zhu, Jieping'
_publ_section_title
;
 Asymmetric Total Synthesis of (-)-Arborisidine and
 (-)-19-epi-Arborisidine Enabled by a Catalytic Enantioselective
 Pictet-Spengler Reaction.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c05804
_journal_year                    2020
_chemical_formula_moiety         'C20 H25 I N2 O3'
_chemical_formula_sum            'C20 H25 I N2 O3'
_chemical_formula_weight         468.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                102.988(3)
_cell_angle_beta                 97.945(3)
_cell_angle_gamma                96.625(3)
_cell_formula_units_Z            4
_cell_length_a                   11.5067(4)
_cell_length_b                   11.7673(4)
_cell_length_c                   15.5305(5)
_cell_measurement_reflns_used    8495
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.4940
_cell_measurement_theta_min      3.8520
_cell_volume                     2005.91(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Mercury 4.3.0 (CCDC, 2019)'
_computing_publication_material  'CIFTab (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -68.00  30.00   1.00    1.00    --  -43.01  57.00 -60.00   98
  2  ω    -53.00  -6.00   1.00    1.00    --  -43.01 125.00  60.00   47
  3  ω   -108.00 -19.00   1.00    1.00    --  -43.01 -57.00 150.00   89
  4  ω    -21.00  72.00   1.00    1.00    --   43.01 -77.00  30.00   93
  5  ω     35.00 107.00   1.00    2.00    --  103.80 -94.00  30.00   72
  6  ω    131.00 177.00   1.00    2.00    --  103.80  77.00  60.00   46
  7  ω     44.00 129.00   1.00    2.00    --  103.80 -30.00 120.00   85
  8  ω     65.00 107.00   1.00    2.00    --  103.80-111.00 150.00   42
  9  ω    139.00 175.00   1.00    2.00    --  103.80 111.00  30.00   36
 10  ω     29.00 155.00   1.00    2.00    --  103.80 -15.00 -30.00  126
 11  ω    153.00 178.00   1.00    2.00    --  103.80 111.00   0.00   25
 12  ω     27.00  85.00   1.00    2.00    --  103.80 -94.00-180.00   58
 13  ω     59.00 106.00   1.00    2.00    --  103.80-111.00-120.00   47
 14  ω    119.00 175.00   1.00    2.00    --  103.80 111.00  90.00   56
 15  ω     84.00 174.00   1.00    2.00    --  103.80  45.00 150.00   90
 16  ω     59.00 131.00   1.00    2.00    --  103.80 -61.00   0.00   72
 17  ω     69.00 127.00   1.00    2.00    --  103.80-144.00  28.16   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.657
_diffrn_reflns_theta_min         3.900
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.717
_exptl_absorpt_correction_T_max  0.224
_exptl_absorpt_correction_T_min  0.049
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.258
_refine_diff_density_max         0.876
_refine_diff_density_min         -1.154
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.00071(7)
_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   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         7744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0315
_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)+(0.0576P)²+0.5918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7418
_reflns_number_total             7744
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c05804_si_012.cif
_cod_data_source_block           randres-6rat121-1-p2b
_cod_original_cell_volume        2005.90(12)
_cod_database_code               4135135
_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.
;
_shelx_estimated_absorpt_t_min   0.069
_shelx_estimated_absorpt_t_max   0.138
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
I1 I 0.73905(2) 0.42946(2) -0.13056(2) 0.03782(7) Uani 1 1 d . . . . .
O1 O 0.58262(15) 0.41857(17) 0.04543(14) 0.0353(4) Uani 1 1 d . . . . .
O2 O 0.79492(16) 0.39332(16) 0.19036(13) 0.0335(4) Uani 1 1 d . . . . .
O3 O 0.96884(15) 0.50306(15) 0.27061(12) 0.0315(4) Uani 1 1 d . . . . .
N1 N 0.65740(17) 0.68938(18) 0.01302(14) 0.0263(4) Uani 1 1 d . . . . .
N2 N 0.85910(16) 0.57270(17) 0.16892(14) 0.0260(4) Uani 1 1 d . . . . .
C1 C 0.7390(2) 0.5748(2) 0.12146(16) 0.0247(4) Uani 1 1 d . . . . .
C2 C 0.75229(19) 0.66204(19) 0.06475(15) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.7000(2) 0.7695(2) -0.03153(16) 0.0259(4) Uani 1 1 d . . . . .
C4 C 0.6388(2) 0.8268(2) -0.08866(17) 0.0322(5) Uani 1 1 d . . . . .
H4 H 0.554855 0.809991 -0.105091 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7052(2) 0.9092(2) -0.12053(18) 0.0360(5) Uani 1 1 d . . . . .
H5 H 0.666023 0.950785 -0.158769 0.043 Uiso 1 1 calc R U . . .
C6 C 0.8298(2) 0.9324(2) -0.09722(18) 0.0350(5) Uani 1 1 d . . . . .
H6 H 0.873266 0.988032 -0.121193 0.042 Uiso 1 1 calc R U . . .
C7 C 0.8898(2) 0.8761(2) -0.04038(17) 0.0295(5) Uani 1 1 d . . . . .
H7 H 0.973854 0.892843 -0.024754 0.035 Uiso 1 1 calc R U . . .
C8 C 0.8247(2) 0.7938(2) -0.00605(16) 0.0256(4) Uani 1 1 d . . . . .
C9 C 0.8556(2) 0.7246(2) 0.05614(16) 0.0258(4) Uani 1 1 d . . . . .
C10 C 0.9712(2) 0.7217(2) 0.11168(18) 0.0296(5) Uani 1 1 d . . . . .
H10A H 1.019863 0.800872 0.128973 0.035 Uiso 1 1 calc R U . . .
H10B H 1.015756 0.665542 0.077245 0.035 Uiso 1 1 calc R U . . .
C11 C 0.9448(2) 0.6827(2) 0.19514(17) 0.0291(5) Uani 1 1 d . . . . .
H11A H 1.019142 0.669850 0.229506 0.035 Uiso 1 1 calc R U . . .
H11B H 0.911618 0.745243 0.234026 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6548(2) 0.6082(2) 0.18735(18) 0.0325(5) Uani 1 1 d . . . . .
H12A H 0.647939 0.549774 0.223191 0.049 Uiso 1 1 calc R U . . .
H12B H 0.576444 0.610059 0.154190 0.049 Uiso 1 1 calc R U . . .
H12C H 0.685956 0.686240 0.227048 0.049 Uiso 1 1 calc R U . . .
C13 C 0.68768(19) 0.4540(2) 0.05600(16) 0.0259(4) Uani 1 1 d . . . . .
C14 C 0.7663(2) 0.3856(2) -0.00084(17) 0.0283(5) Uani 1 1 d . . . . .
H14 H 0.851395 0.410996 0.028156 0.034 Uiso 1 1 calc R U . . .
C15 C 0.7343(3) 0.2529(2) -0.0147(2) 0.0437(6) Uani 1 1 d . . . . .
H15A H 0.651679 0.227860 -0.044882 0.066 Uiso 1 1 calc R U . . .
H15B H 0.743907 0.232896 0.043527 0.066 Uiso 1 1 calc R U . . .
H15C H 0.786715 0.212461 -0.051798 0.066 Uiso 1 1 calc R U . . .
C16 C 0.8691(2) 0.4818(2) 0.20975(16) 0.0281(5) Uani 1 1 d . . . . .
C17 C 1.0159(2) 0.4067(2) 0.30460(17) 0.0294(5) Uani 1 1 d . . . . .
C18 C 1.1296(2) 0.4731(3) 0.36674(19) 0.0371(6) Uani 1 1 d . . . . .
H18A H 1.178265 0.515379 0.333439 0.056 Uiso 1 1 calc R U . . .
H18B H 1.174121 0.416837 0.389603 0.056 Uiso 1 1 calc R U . . .
H18C H 1.109363 0.529650 0.417069 0.056 Uiso 1 1 calc R U . . .
C19 C 0.9308(2) 0.3536(3) 0.35652(19) 0.0390(6) Uani 1 1 d . . . . .
H19A H 0.909130 0.416686 0.401547 0.059 Uiso 1 1 calc R U . . .
H19B H 0.969193 0.299274 0.386409 0.059 Uiso 1 1 calc R U . . .
H19C H 0.859184 0.310437 0.315141 0.059 Uiso 1 1 calc R U . . .
C20 C 1.0429(3) 0.3159(2) 0.2272(2) 0.0393(6) Uani 1 1 d . . . . .
H20A H 0.968528 0.275646 0.187943 0.059 Uiso 1 1 calc R U . . .
H20B H 1.084568 0.258051 0.250340 0.059 Uiso 1 1 calc R U . . .
H20C H 1.093083 0.355137 0.193064 0.059 Uiso 1 1 calc R U . . .
I2 I 0.77640(2) 1.16915(2) 0.53489(2) 0.04097(8) Uani 1 1 d . . . . .
O4 O 0.92568(14) 0.93604(16) 0.56662(13) 0.0323(4) Uani 1 1 d . . . . .
O5 O 0.70796(15) 0.78479(15) 0.61797(12) 0.0306(3) Uani 1 1 d . . . . .
O6 O 0.52663(14) 0.68104(15) 0.54917(11) 0.0281(3) Uani 1 1 d . . . . .
N3 N 0.83870(18) 0.93299(18) 0.35354(14) 0.0263(4) Uani 1 1 d . . . . .
N4 N 0.63487(16) 0.78352(18) 0.47439(13) 0.0256(4) Uani 1 1 d . . . . .
C21 C 0.75565(19) 0.8273(2) 0.46227(15) 0.0235(4) Uani 1 1 d . . . . .
C22 C 0.74200(19) 0.8830(2) 0.38387(16) 0.0247(4) Uani 1 1 d . . . . .
C23 C 0.7963(2) 0.9711(2) 0.27952(16) 0.0262(4) Uani 1 1 d . . . . .
C24 C 0.8578(2) 1.0259(2) 0.22459(19) 0.0343(5) Uani 1 1 d . . . . .
H24 H 0.941733 1.046381 0.237433 0.041 Uiso 1 1 calc R U . . .
C25 C 0.7919(3) 1.0491(2) 0.15100(19) 0.0378(6) Uani 1 1 d . . . . .
H25 H 0.831534 1.087323 0.113109 0.045 Uiso 1 1 calc R U . . .
C26 C 0.6679(3) 1.0177(2) 0.13053(18) 0.0384(6) Uani 1 1 d . . . . .
H26 H 0.625414 1.033867 0.078783 0.046 Uiso 1 1 calc R U . . .
C27 C 0.6070(2) 0.9636(2) 0.18478(17) 0.0325(5) Uani 1 1 d . . . . .
H27 H 0.523203 0.942193 0.170634 0.039 Uiso 1 1 calc R U . . .
C28 C 0.6709(2) 0.9407(2) 0.26103(16) 0.0267(4) Uani 1 1 d . . . . .
C29 C 0.63977(19) 0.8856(2) 0.32964(16) 0.0255(4) Uani 1 1 d . . . . .
C30 C 0.52232(19) 0.8298(2) 0.34274(16) 0.0286(5) Uani 1 1 d . . . . .
H30A H 0.471381 0.793632 0.283860 0.034 Uiso 1 1 calc R U . . .
H30B H 0.481802 0.890220 0.376917 0.034 Uiso 1 1 calc R U . . .
C31 C 0.54274(19) 0.7356(2) 0.39400(16) 0.0277(5) Uani 1 1 d . . . . .
H31A H 0.467649 0.707342 0.412182 0.033 Uiso 1 1 calc R U . . .
H31B H 0.567812 0.667601 0.354574 0.033 Uiso 1 1 calc R U . . .
C32 C 0.8304(2) 0.7274(2) 0.44548(17) 0.0295(5) Uani 1 1 d . . . . .
H32A H 0.836406 0.690994 0.496487 0.044 Uiso 1 1 calc R U . . .
H32B H 0.910077 0.759449 0.438419 0.044 Uiso 1 1 calc R U . . .
H32C H 0.792686 0.667954 0.390797 0.044 Uiso 1 1 calc R U . . .
C33 C 0.81934(19) 0.9263(2) 0.54491(16) 0.0254(4) Uani 1 1 d . . . . .
C34 C 0.7498(2) 1.0172(2) 0.59123(17) 0.0279(5) Uani 1 1 d . . . . .
H34 H 0.663452 0.983936 0.578989 0.034 Uiso 1 1 calc R U . . .
C35 C 0.7933(3) 1.0563(3) 0.69226(18) 0.0388(6) Uani 1 1 d . . . . .
H35A H 0.878268 1.087360 0.703977 0.058 Uiso 1 1 calc R U . . .
H35B H 0.780207 0.988719 0.718695 0.058 Uiso 1 1 calc R U . . .
H35C H 0.749482 1.118001 0.718960 0.058 Uiso 1 1 calc R U . . .
C36 C 0.62837(19) 0.7511(2) 0.55315(16) 0.0260(4) Uani 1 1 d . . . . .
C37 C 0.4842(2) 0.6620(2) 0.63147(16) 0.0276(5) Uani 1 1 d . . . . .
C38 C 0.4606(2) 0.7787(2) 0.68494(18) 0.0352(5) Uani 1 1 d . . . . .
H38A H 0.535887 0.832201 0.707846 0.053 Uiso 1 1 calc R U . . .
H38B H 0.422483 0.765978 0.735330 0.053 Uiso 1 1 calc R U . . .
H38C H 0.408292 0.813711 0.646316 0.053 Uiso 1 1 calc R U . . .
C39 C 0.5713(2) 0.6052(2) 0.68474(19) 0.0353(5) Uani 1 1 d . . . . .
H39A H 0.590499 0.535046 0.645060 0.053 Uiso 1 1 calc R U . . .
H39B H 0.535575 0.582247 0.733223 0.053 Uiso 1 1 calc R U . . .
H39C H 0.644082 0.661592 0.710281 0.053 Uiso 1 1 calc R U . . .
C40 C 0.3689(2) 0.5782(2) 0.59271(18) 0.0329(5) Uani 1 1 d . . . . .
H40A H 0.316038 0.615211 0.556053 0.049 Uiso 1 1 calc R U . . .
H40B H 0.330522 0.560375 0.641662 0.049 Uiso 1 1 calc R U . . .
H40C H 0.385751 0.505027 0.555410 0.049 Uiso 1 1 calc R U . . .
H1 H 0.587(3) 0.661(3) 0.004(2) 0.026(7) Uiso 1 1 d . . . . .
H3 H 0.907(3) 0.955(3) 0.384(2) 0.027(7) Uiso 1 1 d . . . . .
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'
I I -0.3257 6.8362 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 6 -7 0.1442
-2 1 -9 0.1524
-5 -5 0 0.1658
1 -3 10 0.2250
5 3 3 0.1407
0 4 -10 0.1780
5 4 3 0.1406
-4 -2 -5 0.1837
5 4 2 0.1418
4 -7 2 0.2478
7 0 -5 0.1032
-5 6 -1 0.1311
-7 4 2 0.1415
5 -1 -8 0.0978
0 -8 2 0.1754
-3 6 4 0.1173
-2 7 1 0.1285
2 -7 -1 0.1734
1 -2 -9 0.1214
-3 -6 0 0.1392
1 5 5 0.1228
-3 -7 3 0.1528
5 -4 6 0.2628
-5 4 -6 0.1647
7 2 -2 0.1275
-3 -6 6 0.1578
1 -4 -7 0.1230
-2 -7 1 0.1400
-1 5 5 0.1113
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
C16 O3 C17 121.19(19) . . ?
C3 N1 C2 108.34(19) . . ?
C16 N2 C11 122.66(19) . . ?
C16 N2 C1 115.50(18) . . ?
C11 N2 C1 118.39(18) . . ?
N2 C1 C2 106.95(17) . . ?
N2 C1 C12 111.2(2) . . ?
C2 C1 C12 111.41(19) . . ?
N2 C1 C13 111.02(18) . . ?
C2 C1 C13 106.40(19) . . ?
C12 C1 C13 109.71(19) . . ?
C9 C2 N1 110.3(2) . . ?
C9 C2 C1 126.7(2) . . ?
N1 C2 C1 123.01(19) . . ?
N1 C3 C4 129.9(2) . . ?
N1 C3 C8 107.9(2) . . ?
C4 C3 C8 122.1(2) . . ?
C5 C4 C3 117.4(2) . . ?
C4 C5 C6 121.1(2) . . ?
C7 C6 C5 121.3(2) . . ?
C6 C7 C8 118.8(2) . . ?
C7 C8 C3 119.3(2) . . ?
C7 C8 C9 133.9(2) . . ?
C3 C8 C9 106.72(19) . . ?
C2 C9 C8 106.7(2) . . ?
C2 C9 C10 121.8(2) . . ?
C8 C9 C10 131.3(2) . . ?
C9 C10 C11 107.83(19) . . ?
N2 C11 C10 109.8(2) . . ?
O1 C13 C14 120.1(2) . . ?
O1 C13 C1 119.3(2) . . ?
C14 C13 C1 120.35(19) . . ?
C15 C14 C13 112.2(2) . . ?
C15 C14 I1 109.08(18) . . ?
C13 C14 I1 106.59(15) . . ?
O2 C16 O3 126.1(2) . . ?
O2 C16 N2 122.2(2) . . ?
O3 C16 N2 111.7(2) . . ?
O3 C17 C20 109.3(2) . . ?
O3 C17 C19 111.04(19) . . ?
C20 C17 C19 112.5(2) . . ?
O3 C17 C18 101.24(19) . . ?
C20 C17 C18 111.3(2) . . ?
C19 C17 C18 111.0(2) . . ?
C36 O6 C37 121.53(18) . . ?
C23 N3 C22 107.81(19) . . ?
C36 N4 C31 121.95(18) . . ?
C36 N4 C21 115.14(18) . . ?
C31 N4 C21 118.54(18) . . ?
N4 C21 C22 107.02(18) . . ?
N4 C21 C32 111.52(18) . . ?
C22 C21 C32 110.77(19) . . ?
N4 C21 C33 110.93(18) . . ?
C22 C21 C33 106.60(17) . . ?
C32 C21 C33 109.85(19) . . ?
C29 C22 N3 110.2(2) . . ?
C29 C22 C21 127.3(2) . . ?
N3 C22 C21 122.4(2) . . ?
N3 C23 C24 129.9(2) . . ?
N3 C23 C28 108.43(19) . . ?
C24 C23 C28 121.6(2) . . ?
C25 C24 C23 117.5(2) . . ?
C24 C25 C26 121.8(2) . . ?
C27 C26 C25 120.7(2) . . ?
C26 C27 C28 118.9(2) . . ?
C27 C28 C23 119.4(2) . . ?
C27 C28 C29 134.4(2) . . ?
C23 C28 C29 106.1(2) . . ?
C22 C29 C28 107.42(19) . . ?
C22 C29 C30 121.7(2) . . ?
C28 C29 C30 130.8(2) . . ?
C29 C30 C31 108.64(18) . . ?
N4 C31 C30 110.58(19) . . ?
O4 C33 C34 120.7(2) . . ?
O4 C33 C21 119.2(2) . . ?
C34 C33 C21 119.74(19) . . ?
C33 C34 C35 112.1(2) . . ?
C33 C34 I2 106.90(14) . . ?
C35 C34 I2 108.69(17) . . ?
O5 C36 O6 125.9(2) . . ?
O5 C36 N4 122.1(2) . . ?
O6 C36 N4 112.0(2) . . ?
O6 C37 C38 108.41(19) . . ?
O6 C37 C40 101.69(19) . . ?
C38 C37 C40 110.8(2) . . ?
O6 C37 C39 111.31(18) . . ?
C38 C37 C39 113.0(2) . . ?
C40 C37 C39 111.0(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C14 2.180(2) . ?
O1 C13 1.208(3) . ?
O2 C16 1.219(3) . ?
O3 C16 1.342(3) . ?
O3 C17 1.480(3) . ?
N1 C3 1.374(3) . ?
N1 C2 1.377(3) . ?
N2 C16 1.368(3) . ?
N2 C11 1.474(3) . ?
N2 C1 1.479(3) . ?
C1 C2 1.504(3) . ?
C1 C12 1.523(3) . ?
C1 C13 1.547(3) . ?
C2 C9 1.364(3) . ?
C3 C4 1.394(3) . ?
C3 C8 1.413(3) . ?
C4 C5 1.385(4) . ?
C5 C6 1.408(4) . ?
C6 C7 1.377(4) . ?
C7 C8 1.399(3) . ?
C8 C9 1.431(3) . ?
C9 C10 1.490(3) . ?
C10 C11 1.525(3) . ?
C13 C14 1.522(3) . ?
C14 C15 1.521(3) . ?
C17 C20 1.512(4) . ?
C17 C19 1.518(3) . ?
C17 C18 1.526(4) . ?
I2 C34 2.170(2) . ?
O4 C33 1.208(3) . ?
O5 C36 1.221(3) . ?
O6 C36 1.338(3) . ?
O6 C37 1.482(3) . ?
N3 C23 1.374(3) . ?
N3 C22 1.387(3) . ?
N4 C36 1.369(3) . ?
N4 C31 1.477(3) . ?
N4 C21 1.477(3) . ?
C21 C22 1.505(3) . ?
C21 C32 1.532(3) . ?
C21 C33 1.553(3) . ?
C22 C29 1.357(3) . ?
C23 C24 1.397(3) . ?
C23 C28 1.418(3) . ?
C24 C25 1.380(4) . ?
C25 C26 1.405(4) . ?
C26 C27 1.381(4) . ?
C27 C28 1.401(3) . ?
C28 C29 1.431(3) . ?
C29 C30 1.493(3) . ?
C30 C31 1.524(3) . ?
C33 C34 1.521(3) . ?
C34 C35 1.526(4) . ?
C37 C38 1.512(3) . ?
C37 C40 1.518(3) . ?
C37 C39 1.520(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
N1 H1 O1 0.82(3) 2.03(3) 2.836(3) 168(3) 2_665 yes
N3 H3 O4 0.84(3) 2.13(3) 2.917(3) 157(3) 2_776 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
C16 N2 C1 C2 -167.3(2) . . . . ?
C11 N2 C1 C2 33.1(3) . . . . ?
C16 N2 C1 C12 70.8(3) . . . . ?
C11 N2 C1 C12 -88.8(2) . . . . ?
C16 N2 C1 C13 -51.6(3) . . . . ?
C11 N2 C1 C13 148.7(2) . . . . ?
C3 N1 C2 C9 1.2(3) . . . . ?
C3 N1 C2 C1 -178.8(2) . . . . ?
N2 C1 C2 C9 2.0(3) . . . . ?
C12 C1 C2 C9 123.7(3) . . . . ?
C13 C1 C2 C9 -116.7(3) . . . . ?
N2 C1 C2 N1 -178.1(2) . . . . ?
C12 C1 C2 N1 -56.3(3) . . . . ?
C13 C1 C2 N1 63.2(3) . . . . ?
C2 N1 C3 C4 -177.2(3) . . . . ?
C2 N1 C3 C8 -0.7(3) . . . . ?
N1 C3 C4 C5 176.4(3) . . . . ?
C8 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C7 -1.5(4) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C3 0.9(4) . . . . ?
C6 C7 C8 C9 -176.6(3) . . . . ?
N1 C3 C8 C7 -178.2(2) . . . . ?
C4 C3 C8 C7 -1.3(4) . . . . ?
N1 C3 C8 C9 -0.1(3) . . . . ?
C4 C3 C8 C9 176.8(2) . . . . ?
N1 C2 C9 C8 -1.2(3) . . . . ?
C1 C2 C9 C8 178.7(2) . . . . ?
N1 C2 C9 C10 173.7(2) . . . . ?
C1 C2 C9 C10 -6.3(4) . . . . ?
C7 C8 C9 C2 178.5(3) . . . . ?
C3 C8 C9 C2 0.8(3) . . . . ?
C7 C8 C9 C10 4.2(5) . . . . ?
C3 C8 C9 C10 -173.5(3) . . . . ?
C2 C9 C10 C11 -21.5(3) . . . . ?
C8 C9 C10 C11 152.1(3) . . . . ?
C16 N2 C11 C10 139.0(2) . . . . ?
C1 N2 C11 C10 -63.0(3) . . . . ?
C9 C10 C11 N2 52.0(3) . . . . ?
N2 C1 C13 O1 144.3(2) . . . . ?
C2 C1 C13 O1 -99.6(2) . . . . ?
C12 C1 C13 O1 21.0(3) . . . . ?
N2 C1 C13 C14 -41.2(3) . . . . ?
C2 C1 C13 C14 74.8(2) . . . . ?
C12 C1 C13 C14 -164.6(2) . . . . ?
O1 C13 C14 C15 -40.3(3) . . . . ?
C1 C13 C14 C15 145.3(2) . . . . ?
O1 C13 C14 I1 79.0(2) . . . . ?
C1 C13 C14 I1 -95.4(2) . . . . ?
C17 O3 C16 O2 16.5(4) . . . . ?
C17 O3 C16 N2 -162.7(2) . . . . ?
C11 N2 C16 O2 176.6(2) . . . . ?
C1 N2 C16 O2 18.0(3) . . . . ?
C11 N2 C16 O3 -4.2(3) . . . . ?
C1 N2 C16 O3 -162.8(2) . . . . ?
C16 O3 C17 C20 60.1(3) . . . . ?
C16 O3 C17 C19 -64.6(3) . . . . ?
C16 O3 C17 C18 177.5(2) . . . . ?
C36 N4 C21 C22 -167.6(2) . . . . ?
C31 N4 C21 C22 35.4(3) . . . . ?
C36 N4 C21 C32 71.1(3) . . . . ?
C31 N4 C21 C32 -85.9(2) . . . . ?
C36 N4 C21 C33 -51.7(3) . . . . ?
C31 N4 C21 C33 151.3(2) . . . . ?
C23 N3 C22 C29 1.6(3) . . . . ?
C23 N3 C22 C21 177.5(2) . . . . ?
N4 C21 C22 C29 -4.5(3) . . . . ?
C32 C21 C22 C29 117.3(3) . . . . ?
C33 C21 C22 C29 -123.3(2) . . . . ?
N4 C21 C22 N3 -179.7(2) . . . . ?
C32 C21 C22 N3 -57.9(3) . . . . ?
C33 C21 C22 N3 61.5(3) . . . . ?
C22 N3 C23 C24 -179.2(3) . . . . ?
C22 N3 C23 C28 -2.1(3) . . . . ?
N3 C23 C24 C25 176.5(2) . . . . ?
C28 C23 C24 C25 -0.3(4) . . . . ?
C23 C24 C25 C26 -0.9(4) . . . . ?
C24 C25 C26 C27 1.0(4) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C27 C28 C23 -1.4(4) . . . . ?
C26 C27 C28 C29 -178.4(3) . . . . ?
N3 C23 C28 C27 -175.9(2) . . . . ?
C24 C23 C28 C27 1.5(4) . . . . ?
N3 C23 C28 C29 1.8(3) . . . . ?
C24 C23 C28 C29 179.2(2) . . . . ?
N3 C22 C29 C28 -0.5(3) . . . . ?
C21 C22 C29 C28 -176.1(2) . . . . ?
N3 C22 C29 C30 175.6(2) . . . . ?
C21 C22 C29 C30 -0.1(4) . . . . ?
C27 C28 C29 C22 176.4(3) . . . . ?
C23 C28 C29 C22 -0.8(3) . . . . ?
C27 C28 C29 C30 0.8(5) . . . . ?
C23 C28 C29 C30 -176.4(2) . . . . ?
C22 C29 C30 C31 -22.7(3) . . . . ?
C28 C29 C30 C31 152.3(2) . . . . ?
C36 N4 C31 C30 143.5(2) . . . . ?
C21 N4 C31 C30 -61.1(3) . . . . ?
C29 C30 C31 N4 49.6(3) . . . . ?
N4 C21 C33 O4 147.4(2) . . . . ?
C22 C21 C33 O4 -96.4(2) . . . . ?
C32 C21 C33 O4 23.7(3) . . . . ?
N4 C21 C33 C34 -39.0(3) . . . . ?
C22 C21 C33 C34 77.2(2) . . . . ?
C32 C21 C33 C34 -162.75(19) . . . . ?
O4 C33 C34 C35 -40.7(3) . . . . ?
C21 C33 C34 C35 145.8(2) . . . . ?
O4 C33 C34 I2 78.3(2) . . . . ?
C21 C33 C34 I2 -95.21(19) . . . . ?
C37 O6 C36 O5 17.1(4) . . . . ?
C37 O6 C36 N4 -162.58(19) . . . . ?
C31 N4 C36 O5 175.3(2) . . . . ?
C21 N4 C36 O5 19.1(3) . . . . ?
C31 N4 C36 O6 -5.0(3) . . . . ?
C21 N4 C36 O6 -161.19(19) . . . . ?
C36 O6 C37 C38 63.3(3) . . . . ?
C36 O6 C37 C40 -179.9(2) . . . . ?
C36 O6 C37 C39 -61.6(3) . . . . ?
