#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:27:29 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257831 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/97/7059797.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_7059797
loop_
_publ_author_name
'Sviripa, Vitaliy M.'
'Fiandalo, Michael V.'
'Begley, Kristin L.'
'Wyrebek, Przemyslaw'
'Kril, Liliia M.'
'Balia, Andrii G.'
'Parkin, Sean R.'
'Subramanian, Vivekanandan'
'Chen, Xi'
'Williams, Alexander H.'
'Zhan, Chang-Guo'
'Liu, Chunming'
'Mohler, James L.'
'Watt, David S.'
_publ_section_title
;
 Pictet--Spengler condensations using 4-(2-aminoethyl)coumarins
;
_journal_issue                   31
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13415
_journal_page_last               13429
_journal_paper_doi               10.1039/D0NJ02664F
_journal_volume                  44
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C37 H48 N2 O2'
_chemical_formula_sum            'C37 H48 N2 O2'
_chemical_formula_weight         552.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-01-02 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.801(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3920(6)
_cell_length_b                   10.2078(6)
_cell_length_c                   14.5078(9)
_cell_measurement_reflns_used    5113
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.47
_cell_volume                     1480.83(15)
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38404
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         2.810
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       'roughly triangular plate'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
Flack 'x' determined using 2053 quotients [(I+)-(I-)]/[(I+)+(I-)] 
[Parsons, Flack and Wagner (2013)]. 
;
_refine_ls_abs_structure_Flack   -0.4(7)
_refine_ls_extinction_coef       0.008(2)
_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   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         6776
_refine_ls_number_restraints     65
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0532P)²+0.2810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5260
_reflns_number_total             6776
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj02664f2.cif
_cod_data_source_block           m18253
_cod_depositor_comments
;Adding full bibliography for 7059797.cif.

 Adding full bibliography for 7059797.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7059797
_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   0.982
_shelx_estimated_absorpt_t_max   0.998
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O1 O 0.72157(18) 0.50526(18) 0.58592(15) 0.0277(4) Uani 1 1 d . . . . .
O2 O 0.51318(19) 0.5641(2) 0.52511(16) 0.0348(5) Uani 1 1 d . . . . .
N2 N 1.1855(2) 0.4327(2) 0.72755(19) 0.0328(6) Uani 1 1 d . . . . .
C1 C 0.2162(3) 0.3792(3) 0.3161(3) 0.0443(9) Uani 1 1 d . . . . .
H1A H 0.211346 0.319071 0.261735 0.053 Uiso 1 1 calc R U . . .
H1B H 0.145292 0.353661 0.346335 0.053 Uiso 1 1 calc R U . . .
C2 C 0.3536(3) 0.3641(3) 0.3898(3) 0.0462(10) Uani 1 1 d . . . . .
H2A H 0.354797 0.417406 0.446995 0.055 Uiso 1 1 calc R U . A 1
H2B H 0.366117 0.271327 0.410104 0.055 Uiso 1 1 calc DR U . A 1
C3 C 0.4701(3) 0.4061(3) 0.3508(2) 0.0359(8) Uani 0.506(4) 1 d D . P B 1
N1 N 0.4945(5) 0.3354(5) 0.2627(4) 0.0250(8) Uani 0.506(4) 1 d D . P B 1
H1 H 0.525(4) 0.3812(13) 0.220(2) 0.030 Uiso 0.506(4) 1 d D U P B 1
C21 C 0.5748(6) 0.2186(6) 0.2909(5) 0.0287(11) Uani 0.506(4) 1 d D . P B 1
H21A H 0.578303 0.168570 0.233197 0.034 Uiso 0.506(4) 1 calc R U P B 1
H21B H 0.533789 0.162123 0.330625 0.034 Uiso 0.506(4) 1 calc R U P B 1
C22 C 0.7144(3) 0.2563(3) 0.3471(2) 0.0278(6) Uani 0.506(4) 1 d D . P B 1
H22A H 0.761091 0.296995 0.303275 0.033 Uiso 0.506(4) 1 calc R U P B 1
H22B H 0.764305 0.176295 0.374271 0.033 Uiso 0.506(4) 1 calc R U P B 1
C3' C 0.4701(3) 0.4061(3) 0.3508(2) 0.0359(8) Uani 0.494(4) 1 d D . P B 2
N1' N 0.4640(5) 0.2836(5) 0.2958(4) 0.0250(8) Uani 0.494(4) 1 d D . P B 2
H1' H 0.453(4) 0.2020(13) 0.316(3) 0.030 Uiso 0.494(4) 1 d D U P B 2
C21' C 0.5855(6) 0.2754(7) 0.2627(5) 0.0287(11) Uani 0.494(4) 1 d D . P B 2
H21C H 0.594297 0.356668 0.227636 0.034 Uiso 0.494(4) 1 calc R U P B 2
H21D H 0.576732 0.201122 0.217522 0.034 Uiso 0.494(4) 1 calc R U P B 2
C22' C 0.7144(3) 0.2563(3) 0.3471(2) 0.0278(6) Uani 0.494(4) 1 d D . P B 2
H22C H 0.717929 0.165243 0.371144 0.033 Uiso 0.494(4) 1 calc R U P B 2
H22D H 0.794433 0.271333 0.323954 0.033 Uiso 0.494(4) 1 calc R U P B 2
C4 C 0.4410(3) 0.5408(3) 0.3022(2) 0.0341(7) Uani 1 1 d . . . . .
H4A H 0.448408 0.608628 0.352124 0.041 Uiso 1 1 calc R U . B 1
H4B H 0.509763 0.559652 0.268331 0.041 Uiso 1 1 calc DR U . B 1
C5 C 0.3023(3) 0.5504(3) 0.2305(2) 0.0327(7) Uani 1 1 d . . . . .
H5 H 0.298176 0.481197 0.180943 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2827(3) 0.6818(4) 0.1784(3) 0.050(1) Uani 1 1 d . . . . .
H6A H 0.356620 0.696506 0.148593 0.060 Uiso 1 1 calc R U . . .
H6B H 0.284728 0.753251 0.224890 0.060 Uiso 1 1 calc R U . . .
C7 C 0.1492(3) 0.6843(4) 0.1011(3) 0.0449(9) Uani 1 1 d . . . . .
H7A H 0.136376 0.770999 0.069309 0.054 Uiso 1 1 calc R U . . .
H7B H 0.149470 0.617011 0.051973 0.054 Uiso 1 1 calc R U . . .
C8 C 0.0351(3) 0.6576(3) 0.1456(2) 0.0269(6) Uani 1 1 d . . . . .
H8 H 0.037264 0.728554 0.193460 0.032 Uiso 1 1 calc R U . . .
C9 C 0.0543(3) 0.5271(3) 0.2006(2) 0.0283(6) Uani 1 1 d . . . . .
H9 H 0.054898 0.456364 0.152989 0.034 Uiso 1 1 calc R U . . .
C10 C 0.1904(3) 0.5199(3) 0.2781(2) 0.0256(6) Uani 1 1 d . . . . .
C11 C -0.0680(3) 0.5036(4) 0.2374(3) 0.0426(9) Uani 1 1 d . . . . .
H11A H -0.079474 0.578792 0.277587 0.051 Uiso 1 1 calc R U . . .
H11B H -0.053416 0.424168 0.278077 0.051 Uiso 1 1 calc R U . . .
C12 C -0.1956(3) 0.4864(4) 0.1552(3) 0.0484(10) Uani 1 1 d . . . . .
H12A H -0.196613 0.397741 0.127402 0.058 Uiso 1 1 calc R U . . .
H12B H -0.274743 0.494617 0.180351 0.058 Uiso 1 1 calc R U . . .
C13 C -0.2034(3) 0.5862(3) 0.0793(2) 0.0328(7) Uani 1 1 d . . . . .
C14 C -0.1011(3) 0.6620(3) 0.0747(2) 0.0285(6) Uani 1 1 d . . . . .
C15 C -0.1379(3) 0.7515(3) -0.0116(2) 0.0346(7) Uani 1 1 d . . . . .
H15A H -0.098993 0.720169 -0.062743 0.041 Uiso 1 1 calc R U . . .
H15B H -0.107579 0.842360 0.005890 0.041 Uiso 1 1 calc R U . . .
C16 C -0.2914(3) 0.7428(3) -0.0429(2) 0.0390(8) Uani 1 1 d . . . . .
H16A H -0.325378 0.746446 -0.113598 0.047 Uiso 1 1 calc R U . . .
H16B H -0.331384 0.815763 -0.015207 0.047 Uiso 1 1 calc R U . . .
C17 C -0.3259(3) 0.6092(3) -0.0046(2) 0.0355(7) Uani 1 1 d . . . . .
C18' C -0.4562(3) 0.6169(4) 0.0236(3) 0.0494(9) Uani 1 1 d . . . . .
H18A H -0.527961 0.646514 -0.031434 0.074 Uiso 1 1 calc R U . . .
H18B H -0.446252 0.678985 0.076560 0.074 Uiso 1 1 calc R U . . .
H18C H -0.478365 0.530106 0.043745 0.074 Uiso 1 1 calc R U . . .
C19 C 0.1898(3) 0.6114(3) 0.3607(2) 0.0354(7) Uani 1 1 d . . . . .
H19A H 0.167756 0.700407 0.336138 0.053 Uiso 1 1 calc R U . . .
H19B H 0.278338 0.611225 0.406914 0.053 Uiso 1 1 calc R U . . .
H19C H 0.122852 0.581503 0.392269 0.053 Uiso 1 1 calc R U . . .
C20 C -0.3348(4) 0.5022(4) -0.0804(3) 0.0553(10) Uani 1 1 d . . . . .
H20A H -0.406502 0.523735 -0.137870 0.083 Uiso 1 1 calc R U . . .
H20B H -0.353876 0.417794 -0.054832 0.083 Uiso 1 1 calc R U . . .
H20C H -0.249537 0.496872 -0.096935 0.083 Uiso 1 1 calc R U . . .
C23 C 0.7149(3) 0.3507(3) 0.4273(2) 0.0236(6) Uani 1 1 d . . . . .
C24 C 0.6019(3) 0.4144(3) 0.4309(2) 0.0264(6) Uani 1 1 d . . . . .
C25 C 0.6046(3) 0.4987(3) 0.5125(2) 0.0263(6) Uani 1 1 d . . . . .
C26 C 0.8381(3) 0.4463(3) 0.5802(2) 0.0248(6) Uani 1 1 d . . . . .
C27 C 0.8385(3) 0.3688(3) 0.5013(2) 0.0237(6) Uani 1 1 d . . . . .
C28 C 0.9609(3) 0.3101(3) 0.5017(2) 0.0265(6) Uani 1 1 d . . . . .
H28 H 0.965140 0.256505 0.449112 0.032 Uiso 1 1 calc R U . . .
C29 C 1.0749(3) 0.3275(3) 0.5758(2) 0.0297(7) Uani 1 1 d . . . . .
C30 C 1.2033(3) 0.2591(3) 0.5745(3) 0.0384(8) Uani 1 1 d . . . . .
H30A H 1.208788 0.251530 0.507604 0.046 Uiso 1 1 calc R U . . .
H30B H 1.203982 0.169590 0.600858 0.046 Uiso 1 1 calc R U . . .
C31 C 1.3235(3) 0.3351(3) 0.6336(3) 0.0417(8) Uani 1 1 d . . . . .
H31A H 1.406712 0.285228 0.638061 0.050 Uiso 1 1 calc R U . . .
H31B H 1.330218 0.420516 0.602846 0.050 Uiso 1 1 calc R U . . .
C32 C 1.3055(3) 0.3564(3) 0.7326(3) 0.0415(8) Uani 1 1 d . . . . .
H32A H 1.298790 0.270552 0.762698 0.050 Uiso 1 1 calc R U . . .
H32B H 1.384397 0.402948 0.772964 0.050 Uiso 1 1 calc R U . . .
C33 C 1.0700(3) 0.4082(3) 0.6549(2) 0.0271(6) Uani 1 1 d . . . . .
C34 C 0.9488(3) 0.4656(3) 0.6578(2) 0.0261(6) Uani 1 1 d . . . . .
C35 C 0.9367(3) 0.5419(3) 0.7437(2) 0.0332(7) Uani 0.914(6) 1 d D . P C 1
H35A H 0.898453 0.484848 0.784708 0.040 Uiso 0.914(6) 1 calc R U P C 1
H35B H 0.874788 0.616438 0.722216 0.040 Uiso 0.914(6) 1 calc R U P C 1
C36 C 1.0704(3) 0.5929(4) 0.8012(3) 0.0365(9) Uani 0.914(6) 1 d D . P C 1
H36A H 1.097279 0.667491 0.766925 0.044 Uiso 0.914(6) 1 calc R U P C 1
H36B H 1.062834 0.625203 0.863844 0.044 Uiso 0.914(6) 1 calc R U P C 1
C37 C 1.1751(3) 0.4890(4) 0.8171(2) 0.0396(8) Uani 0.914(6) 1 d D . P C 1
H37A H 1.262484 0.526905 0.851919 0.047 Uiso 0.914(6) 1 calc R U P C 1
H37B H 1.153136 0.418921 0.857560 0.047 Uiso 0.914(6) 1 calc R U P C 1
C35' C 0.9367(3) 0.5419(3) 0.7437(2) 0.0332(7) Uani 0.086(6) 1 d D . P C 2
H35C H 0.940292 0.636643 0.729952 0.040 Uiso 0.086(6) 1 calc R U P C 2
H35D H 0.848313 0.523584 0.754403 0.040 Uiso 0.086(6) 1 calc R U P C 2
C36' C 1.040(2) 0.512(4) 0.8301(19) 0.0365(9) Uani 0.086(6) 1 d D . P C 2
H36C H 1.012301 0.432714 0.859447 0.044 Uiso 0.086(6) 1 calc R U P C 2
H36D H 1.045224 0.585122 0.875775 0.044 Uiso 0.086(6) 1 calc R U P C 2
C37' C 1.1751(3) 0.4890(4) 0.8171(2) 0.0396(8) Uani 0.086(6) 1 d D . P C 2
H37C H 1.222654 0.574013 0.825709 0.047 Uiso 0.086(6) 1 calc R U P C 2
H37D H 1.224128 0.430880 0.869632 0.047 Uiso 0.086(6) 1 calc R U P C 2
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'
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
C26 O1 C25 122.4(2) . . ?
C33 N2 C37' 119.5(2) . . ?
C33 N2 C37 119.5(2) . . ?
C33 N2 C32 119.6(3) . . ?
C37' N2 C32 116.0(3) . . ?
C37 N2 C32 116.0(3) . . ?
C10 C1 C2 112.4(2) . . ?
C10 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
C10 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C3' C2 C1 113.1(3) . . ?
C3 C2 C1 113.1(3) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 110.1(2) . . ?
C2 C3 C24 111.6(3) . . ?
C4 C3 C24 108.7(2) . . ?
C2 C3 N1 119.9(3) . . ?
C4 C3 N1 95.4(3) . . ?
C24 C3 N1 109.7(3) . . ?
C21 N1 C3 111.2(4) . . ?
C21 N1 H1 110(2) . . ?
C3 N1 H1 119.6(11) . . ?
N1 C21 C22 109.8(4) . . ?
N1 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
N1 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
C21 C22 C23 112.4(3) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
N1' C3' C2 92.3(3) . . ?
N1' C3' C4 122.4(3) . . ?
C2 C3' C4 110.1(2) . . ?
N1' C3' C24 110.7(3) . . ?
C2 C3' C24 111.6(3) . . ?
C4 C3' C24 108.7(2) . . ?
C21' N1' C3' 108.1(4) . . ?
C21' N1' H1' 104.8(17) . . ?
C3' N1' H1' 126.4(16) . . ?
N1' C21' C22' 112.4(5) . . ?
N1' C21' H21C 109.1 . . ?
C22' C21' H21C 109.1 . . ?
N1' C21' H21D 109.1 . . ?
C22' C21' H21D 109.1 . . ?
H21C C21' H21D 107.9 . . ?
C23 C22' C21' 110.3(3) . . ?
C23 C22' H22C 109.6 . . ?
C21' C22' H22C 109.6 . . ?
C23 C22' H22D 109.6 . . ?
C21' C22' H22D 109.6 . . ?
H22C C22' H22D 108.1 . . ?
C5 C4 C3 113.5(3) . . ?
C5 C4 C3' 113.5(3) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 111.5(3) . . ?
C6 C5 C10 112.6(2) . . ?
C4 C5 C10 111.6(2) . . ?
C6 C5 H5 106.9 . . ?
C4 C5 H5 106.9 . . ?
C10 C5 H5 106.9 . . ?
C5 C6 C7 110.5(3) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 110.0(3) . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C14 C8 C7 113.7(2) . . ?
C14 C8 C9 110.2(2) . . ?
C7 C8 C9 111.7(2) . . ?
C14 C8 H8 107.0 . . ?
C7 C8 H8 107.0 . . ?
C9 C8 H8 107.0 . . ?
C11 C9 C8 108.3(2) . . ?
C11 C9 C10 114.9(3) . . ?
C8 C9 C10 112.4(2) . . ?
C11 C9 H9 106.9 . . ?
C8 C9 H9 106.9 . . ?
C10 C9 H9 106.9 . . ?
C19 C10 C1 109.2(3) . . ?
C19 C10 C5 113.3(2) . . ?
C1 C10 C5 105.7(2) . . ?
C19 C10 C9 110.1(2) . . ?
C1 C10 C9 109.9(2) . . ?
C5 C10 C9 108.5(2) . . ?
C9 C11 C12 111.8(3) . . ?
C9 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C9 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 111.1(3) . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 123.5(3) . . ?
C14 C13 C17 112.1(3) . . ?
C12 C13 C17 124.3(3) . . ?
C13 C14 C8 124.3(3) . . ?
C13 C14 C15 111.5(3) . . ?
C8 C14 C15 124.2(3) . . ?
C14 C15 C16 102.6(2) . . ?
C14 C15 H15A 111.3 . . ?
C16 C15 H15A 111.3 . . ?
C14 C15 H15B 111.3 . . ?
C16 C15 H15B 111.3 . . ?
H15A C15 H15B 109.2 . . ?
C15 C16 C17 105.5(2) . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
C18' C17 C13 114.0(3) . . ?
C18' C17 C20 110.2(3) . . ?
C13 C17 C20 109.7(3) . . ?
C18' C17 C16 111.2(3) . . ?
C13 C17 C16 101.4(2) . . ?
C20 C17 C16 110.1(3) . . ?
C17 C18' H18A 109.5 . . ?
C17 C18' H18B 109.5 . . ?
H18A C18' H18B 109.5 . . ?
C17 C18' H18C 109.5 . . ?
H18A C18' H18C 109.5 . . ?
H18B C18' H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24 C23 C27 121.0(3) . . ?
C24 C23 C22' 120.9(2) . . ?
C27 C23 C22' 118.1(2) . . ?
C24 C23 C22 120.9(2) . . ?
C27 C23 C22 118.1(2) . . ?
C23 C24 C25 119.3(3) . . ?
C23 C24 C3' 123.2(3) . . ?
C25 C24 C3' 117.5(2) . . ?
C23 C24 C3 123.2(3) . . ?
C25 C24 C3 117.5(2) . . ?
O2 C25 O1 114.6(2) . . ?
O2 C25 C24 127.2(3) . . ?
O1 C25 C24 118.2(2) . . ?
O1 C26 C34 115.9(3) . . ?
O1 C26 C27 119.9(2) . . ?
C34 C26 C27 124.1(2) . . ?
C26 C27 C28 116.3(2) . . ?
C26 C27 C23 118.9(2) . . ?
C28 C27 C23 124.8(3) . . ?
C29 C28 C27 122.3(3) . . ?
C29 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C28 C29 C33 119.4(3) . . ?
C28 C29 C30 120.4(3) . . ?
C33 C29 C30 120.2(3) . . ?
C29 C30 C31 110.5(3) . . ?
C29 C30 H30A 109.6 . . ?
C31 C30 H30A 109.6 . . ?
C29 C30 H30B 109.6 . . ?
C31 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
C32 C31 C30 108.2(3) . . ?
C32 C31 H31A 110.1 . . ?
C30 C31 H31A 110.1 . . ?
C32 C31 H31B 110.1 . . ?
C30 C31 H31B 110.1 . . ?
H31A C31 H31B 108.4 . . ?
N2 C32 C31 110.8(3) . . ?
N2 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N2 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
N2 C33 C34 120.0(3) . . ?
N2 C33 C29 120.2(2) . . ?
C34 C33 C29 119.8(2) . . ?
C26 C34 C33 118.0(3) . . ?
C26 C34 C35' 120.6(2) . . ?
C33 C34 C35' 121.4(2) . . ?
C26 C34 C35 120.6(2) . . ?
C33 C34 C35 121.4(2) . . ?
C34 C35 C36 111.4(3) . . ?
C34 C35 H35A 109.3 . . ?
C36 C35 H35A 109.3 . . ?
C34 C35 H35B 109.3 . . ?
C36 C35 H35B 109.3 . . ?
H35A C35 H35B 108.0 . . ?
C37 C36 C35 111.3(3) . . ?
C37 C36 H36A 109.4 . . ?
C35 C36 H36A 109.4 . . ?
C37 C36 H36B 109.4 . . ?
C35 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?
N2 C37 C36 111.8(3) . . ?
N2 C37 H37A 109.3 . . ?
C36 C37 H37A 109.3 . . ?
N2 C37 H37B 109.3 . . ?
C36 C37 H37B 109.3 . . ?
H37A C37 H37B 107.9 . . ?
C36' C35' C34 113.6(13) . . ?
C36' C35' H35C 108.8 . . ?
C34 C35' H35C 108.8 . . ?
C36' C35' H35D 108.8 . . ?
C34 C35' H35D 108.8 . . ?
H35C C35' H35D 107.7 . . ?
C35' C36' C37' 115.2(18) . . ?
C35' C36' H36C 108.5 . . ?
C37' C36' H36C 108.5 . . ?
C35' C36' H36D 108.5 . . ?
C37' C36' H36D 108.5 . . ?
H36C C36' H36D 107.5 . . ?
N2 C37' C36' 118.6(11) . . ?
N2 C37' H37C 107.7 . . ?
C36' C37' H37C 107.7 . . ?
N2 C37' H37D 107.7 . . ?
C36' C37' H37D 107.7 . . ?
H37C C37' H37D 107.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C26 1.376(3) . ?
O1 C25 1.383(3) . ?
O2 C25 1.215(3) . ?
N2 C33 1.388(3) . ?
N2 C37' 1.452(4) . ?
N2 C37 1.452(4) . ?
N2 C32 1.455(4) . ?
C1 C10 1.536(4) . ?
C1 C2 1.540(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3' 1.530(5) . ?
C2 C3 1.530(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.537(5) . ?
C3 C24 1.539(4) . ?
C3 N1 1.547(6) . ?
N1 C21 1.449(7) . ?
N1 H1 0.900(13) . ?
C21 C22 1.508(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.510(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C3' N1' 1.475(5) . ?
C3' C4 1.537(5) . ?
C3' C24 1.539(4) . ?
N1' C21' 1.470(8) . ?
N1' H1' 0.904(13) . ?
C21' C22' 1.562(7) . ?
C21' H21C 0.9900 . ?
C21' H21D 0.9900 . ?
C22' C23 1.510(4) . ?
C22' H22C 0.9900 . ?
C22' H22D 0.9900 . ?
C4 C5 1.534(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.526(5) . ?
C5 C10 1.536(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.528(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C14 1.506(4) . ?
C8 C9 1.538(4) . ?
C8 H8 1.0000 . ?
C9 C11 1.526(4) . ?
C9 C10 1.550(4) . ?
C9 H9 1.0000 . ?
C10 C19 1.521(4) . ?
C11 C12 1.533(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.486(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.330(4) . ?
C13 C17 1.521(4) . ?
C14 C15 1.513(4) . ?
C15 C16 1.538(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.551(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18' 1.519(5) . ?
C17 C20 1.535(5) . ?
C18' H18A 0.9800 . ?
C18' H18B 0.9800 . ?
C18' H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C23 C24 1.356(4) . ?
C23 C27 1.443(4) . ?
C24 C25 1.457(4) . ?
C26 C34 1.387(4) . ?
C26 C27 1.392(4) . ?
C27 C28 1.404(4) . ?
C28 C29 1.377(4) . ?
C28 H28 0.9500 . ?
C29 C33 1.425(4) . ?
C29 C30 1.511(4) . ?
C30 C31 1.521(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.514(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.400(4) . ?
C34 C35' 1.503(4) . ?
C34 C35 1.503(4) . ?
C35 C36 1.506(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.492(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C35' C36' 1.44(2) . ?
C35' H35C 0.9900 . ?
C35' H35D 0.9900 . ?
C36' C37' 1.49(2) . ?
C36' H36C 0.9900 . ?
C36' H36D 0.9900 . ?
C37' H37C 0.9900 . ?
C37' H37D 0.9900 . ?
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
C10 C1 C2 C3' -56.7(4) . . . . ?
C10 C1 C2 C3 -56.7(4) . . . . ?
C1 C2 C3 C4 48.5(4) . . . . ?
C1 C2 C3 C24 169.3(3) . . . . ?
C1 C2 C3 N1 -60.5(4) . . . . ?
C2 C3 N1 C21 -85.6(5) . . . . ?
C4 C3 N1 C21 157.5(4) . . . . ?
C24 C3 N1 C21 45.4(5) . . . . ?
C3 N1 C21 C22 -67.3(6) . . . . ?
N1 C21 C22 C23 50.3(6) . . . . ?
C1 C2 C3' N1' -77.3(3) . . . . ?
C1 C2 C3' C4 48.5(4) . . . . ?
C1 C2 C3' C24 169.3(3) . . . . ?
C2 C3' N1' C21' -167.8(4) . . . . ?
C4 C3' N1' C21' 76.6(5) . . . . ?
C24 C3' N1' C21' -53.6(5) . . . . ?
C3' N1' C21' C22' 67.4(6) . . . . ?
N1' C21' C22' C23 -46.5(6) . . . . ?
C2 C3 C4 C5 -49.3(4) . . . . ?
C24 C3 C4 C5 -171.9(2) . . . . ?
N1 C3 C4 C5 75.2(3) . . . . ?
N1' C3' C4 C5 57.1(4) . . . . ?
C2 C3' C4 C5 -49.3(4) . . . . ?
C24 C3' C4 C5 -171.9(2) . . . . ?
C3 C4 C5 C6 -175.4(3) . . . . ?
C3' C4 C5 C6 -175.4(3) . . . . ?
C3 C4 C5 C10 57.7(3) . . . . ?
C3' C4 C5 C10 57.7(3) . . . . ?
C4 C5 C6 C7 174.9(3) . . . . ?
C10 C5 C6 C7 -58.8(4) . . . . ?
C5 C6 C7 C8 57.5(4) . . . . ?
C6 C7 C8 C14 178.3(3) . . . . ?
C6 C7 C8 C9 -56.2(4) . . . . ?
C14 C8 C9 C11 -49.1(3) . . . . ?
C7 C8 C9 C11 -176.5(3) . . . . ?
C14 C8 C9 C10 -177.2(2) . . . . ?
C7 C8 C9 C10 55.4(3) . . . . ?
C2 C1 C10 C19 -62.1(4) . . . . ?
C2 C1 C10 C5 60.2(4) . . . . ?
C2 C1 C10 C9 177.1(3) . . . . ?
C6 C5 C10 C19 -67.1(3) . . . . ?
C4 C5 C10 C19 59.2(3) . . . . ?
C6 C5 C10 C1 173.4(3) . . . . ?
C4 C5 C10 C1 -60.3(3) . . . . ?
C6 C5 C10 C9 55.6(3) . . . . ?
C4 C5 C10 C9 -178.1(2) . . . . ?
C11 C9 C10 C19 -53.4(3) . . . . ?
C8 C9 C10 C19 71.1(3) . . . . ?
C11 C9 C10 C1 66.9(3) . . . . ?
C8 C9 C10 C1 -168.6(3) . . . . ?
C11 C9 C10 C5 -178.0(3) . . . . ?
C8 C9 C10 C5 -53.5(3) . . . . ?
C8 C9 C11 C12 64.1(4) . . . . ?
C10 C9 C11 C12 -169.2(3) . . . . ?
C9 C11 C12 C13 -44.5(4) . . . . ?
C11 C12 C13 C14 12.5(5) . . . . ?
C11 C12 C13 C17 -170.6(3) . . . . ?
C12 C13 C14 C8 -0.3(5) . . . . ?
C17 C13 C14 C8 -177.5(3) . . . . ?
C12 C13 C14 C15 178.6(3) . . . . ?
C17 C13 C14 C15 1.4(4) . . . . ?
C7 C8 C14 C13 145.6(3) . . . . ?
C9 C8 C14 C13 19.4(4) . . . . ?
C7 C8 C14 C15 -33.2(4) . . . . ?
C9 C8 C14 C15 -159.4(3) . . . . ?
C13 C14 C15 C16 14.9(3) . . . . ?
C8 C14 C15 C16 -166.1(3) . . . . ?
C14 C15 C16 C17 -24.6(3) . . . . ?
C14 C13 C17 C18' -136.4(3) . . . . ?
C12 C13 C17 C18' 46.4(4) . . . . ?
C14 C13 C17 C20 99.5(3) . . . . ?
C12 C13 C17 C20 -77.7(4) . . . . ?
C14 C13 C17 C16 -16.9(3) . . . . ?
C12 C13 C17 C16 166.0(3) . . . . ?
C15 C16 C17 C18' 146.6(3) . . . . ?
C15 C16 C17 C13 25.1(3) . . . . ?
C15 C16 C17 C20 -91.0(3) . . . . ?
C21' C22' C23 C24 15.4(4) . . . . ?
C21' C22' C23 C27 -166.0(3) . . . . ?
C21 C22 C23 C24 -14.3(5) . . . . ?
C21 C22 C23 C27 164.3(4) . . . . ?
C27 C23 C24 C25 -2.2(4) . . . . ?
C22' C23 C24 C25 176.4(3) . . . . ?
C22 C23 C24 C25 176.4(3) . . . . ?
C27 C23 C24 C3' 175.7(3) . . . . ?
C22' C23 C24 C3' -5.7(4) . . . . ?
C27 C23 C24 C3 175.7(3) . . . . ?
C22 C23 C24 C3 -5.7(4) . . . . ?
N1' C3' C24 C23 24.8(5) . . . . ?
C2 C3' C24 C23 126.1(3) . . . . ?
C4 C3' C24 C23 -112.3(3) . . . . ?
N1' C3' C24 C25 -157.2(3) . . . . ?
C2 C3' C24 C25 -55.9(3) . . . . ?
C4 C3' C24 C25 65.7(4) . . . . ?
C2 C3 C24 C23 126.1(3) . . . . ?
C4 C3 C24 C23 -112.3(3) . . . . ?
N1 C3 C24 C23 -9.1(4) . . . . ?
C2 C3 C24 C25 -55.9(3) . . . . ?
C4 C3 C24 C25 65.7(4) . . . . ?
N1 C3 C24 C25 168.8(3) . . . . ?
C26 O1 C25 O2 -174.5(2) . . . . ?
C26 O1 C25 C24 6.8(4) . . . . ?
C23 C24 C25 O2 178.3(3) . . . . ?
C3' C24 C25 O2 0.3(5) . . . . ?
C3 C24 C25 O2 0.3(5) . . . . ?
C23 C24 C25 O1 -3.2(4) . . . . ?
C3' C24 C25 O1 178.8(2) . . . . ?
C3 C24 C25 O1 178.8(2) . . . . ?
C25 O1 C26 C34 177.5(2) . . . . ?
C25 O1 C26 C27 -4.8(4) . . . . ?
O1 C26 C27 C28 -178.8(2) . . . . ?
C34 C26 C27 C28 -1.3(4) . . . . ?
O1 C26 C27 C23 -0.8(4) . . . . ?
C34 C26 C27 C23 176.7(3) . . . . ?
C24 C23 C27 C26 4.3(4) . . . . ?
C22' C23 C27 C26 -174.3(2) . . . . ?
C22 C23 C27 C26 -174.3(2) . . . . ?
C24 C23 C27 C28 -177.9(3) . . . . ?
C22' C23 C27 C28 3.5(4) . . . . ?
C22 C23 C27 C28 3.5(4) . . . . ?
C26 C27 C28 C29 0.0(4) . . . . ?
C23 C27 C28 C29 -177.9(3) . . . . ?
C27 C28 C29 C33 -0.3(4) . . . . ?
C27 C28 C29 C30 178.2(3) . . . . ?
C28 C29 C30 C31 154.4(3) . . . . ?
C33 C29 C30 C31 -27.1(4) . . . . ?
C29 C30 C31 C32 53.8(4) . . . . ?
C33 N2 C32 C31 40.6(4) . . . . ?
C37' N2 C32 C31 -164.4(3) . . . . ?
C37 N2 C32 C31 -164.4(3) . . . . ?
C30 C31 C32 N2 -61.2(3) . . . . ?
C37' N2 C33 C34 15.7(4) . . . . ?
C37 N2 C33 C34 15.7(4) . . . . ?
C32 N2 C33 C34 169.8(3) . . . . ?
C37' N2 C33 C29 -166.0(3) . . . . ?
C37 N2 C33 C29 -166.0(3) . . . . ?
C32 N2 C33 C29 -11.9(4) . . . . ?
C28 C29 C33 N2 -176.4(3) . . . . ?
C30 C29 C33 N2 5.0(4) . . . . ?
C28 C29 C33 C34 1.8(4) . . . . ?
C30 C29 C33 C34 -176.7(3) . . . . ?
O1 C26 C34 C33 -179.6(2) . . . . ?
C27 C26 C34 C33 2.8(4) . . . . ?
O1 C26 C34 C35' 2.6(4) . . . . ?
C27 C26 C34 C35' -174.9(3) . . . . ?
O1 C26 C34 C35 2.6(4) . . . . ?
C27 C26 C34 C35 -174.9(3) . . . . ?
N2 C33 C34 C26 175.3(3) . . . . ?
C29 C33 C34 C26 -3.0(4) . . . . ?
N2 C33 C34 C35' -6.9(4) . . . . ?
C29 C33 C34 C35' 174.8(3) . . . . ?
N2 C33 C34 C35 -6.9(4) . . . . ?
C29 C33 C34 C35 174.8(3) . . . . ?
C26 C34 C35 C36 -159.2(3) . . . . ?
C33 C34 C35 C36 23.1(4) . . . . ?
C34 C35 C36 C37 -46.7(4) . . . . ?
C33 N2 C37 C36 -40.4(4) . . . . ?
C32 N2 C37 C36 164.5(3) . . . . ?
C35 C36 C37 N2 55.8(4) . . . . ?
C26 C34 C35' C36' 157.0(16) . . . . ?
C33 C34 C35' C36' -20.7(16) . . . . ?
C34 C35' C36' C37' 38(3) . . . . ?
C33 N2 C37' C36' 3.4(17) . . . . ?
C32 N2 C37' C36' -151.7(17) . . . . ?
C35' C36' C37' N2 -31(3) . . . . ?
