#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:22:05 +0200 (Tue 05 de Sep de 2023) $
#$Revision: 286187 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/95/7159518.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_7159518
loop_
_publ_author_name
'Zhao, Jianbo'
'Wu, Min'
'Luo, Jiamin'
'Shi, Lei'
'Li, Hao'
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed enantioselective annulation of
 2-amino-1H-indoles and bromoenals for the synthesis of chiral
 2-aryl-2,3-dihydropyrimido[1,2-a]indol-4 (1H)-ones.
;
_journal_issue                   33
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6675
_journal_page_last               6680
_journal_paper_doi               10.1039/d3ob01006f
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C18 H13 N3 O'
_chemical_formula_weight         287.31
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-05-03 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.864(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4603(2)
_cell_length_b                   20.5881(9)
_cell_length_c                   12.9406(6)
_cell_measurement_reflns_used    5458
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      137.743
_cell_measurement_theta_min      8.083
_cell_volume                     1451.44(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19539
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.985
_diffrn_reflns_theta_min         4.041
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
; 
 Flack x determined using 1569 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         5271
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0644
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1010P)²+0.1783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1932
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4026
_reflns_number_total             5271
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01006f2.cif
_cod_data_source_block           d8v23073
_cod_depositor_comments          'Adding full bibliography for 7159518.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159518
_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   0.911
_shelx_estimated_absorpt_t_max   0.961
_shelxl_version_number           2013-4
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 0.2818(7) 0.2922(2) 0.4510(4) 0.0918(13) Uani 1 1 d . . . . .
N1 N 0.8661(9) 0.4093(2) 0.4194(4) 0.0730(12) Uani 1 1 d . . . . .
H1 H 0.9451 0.4444 0.4081 0.088 Uiso 1 1 calc R U . . .
N2 N 0.5974(7) 0.3527(2) 0.5233(4) 0.0713(11) Uani 1 1 d . . . . .
N3 N 1.2314(10) 0.4939(3) 0.6561(5) 0.0901(15) Uani 1 1 d . . . . .
C1 C 0.4572(9) 0.3275(2) 0.4383(5) 0.0750(15) Uani 1 1 d . . . . .
C2 C 0.5352(10) 0.3486(3) 0.3354(5) 0.0819(16) Uani 1 1 d . . . . .
H2A H 0.4448 0.3874 0.3138 0.098 Uiso 1 1 calc R U . . .
H2B H 0.4940 0.3148 0.2849 0.098 Uiso 1 1 calc R U . . .
C3 C 0.8079(10) 0.3626(2) 0.3366(4) 0.0716(13) Uani 1 1 d . . . . .
H3 H 0.8954 0.3222 0.3549 0.086 Uiso 1 1 calc R U . . .
C4 C 0.8905(11) 0.3851(3) 0.2343(5) 0.0782(15) Uani 1 1 d . . . . .
C5 C 0.9498(16) 0.3407(4) 0.1625(6) 0.107(2) Uani 1 1 d . . . . .
H5 H 0.9310 0.2968 0.1768 0.129 Uiso 1 1 calc R U . . .
C6 C 1.038(2) 0.3588(6) 0.0686(6) 0.133(3) Uani 1 1 d . . . . .
H6 H 1.0764 0.3270 0.0215 0.160 Uiso 1 1 calc R U . . .
C7 C 1.067(2) 0.4214(6) 0.0448(7) 0.141(4) Uani 1 1 d . . . . .
H7 H 1.1223 0.4339 -0.0186 0.169 Uiso 1 1 calc R U . . .
C8 C 1.012(3) 0.4666(5) 0.1188(8) 0.159(5) Uani 1 1 d . . . . .
H8 H 1.0372 0.5104 0.1056 0.191 Uiso 1 1 calc R U . . .
C9 C 0.9212(19) 0.4487(3) 0.2113(6) 0.117(3) Uani 1 1 d . . . . .
H9 H 0.8806 0.4805 0.2583 0.140 Uiso 1 1 calc R U . . .
C10 C 0.7926(8) 0.3956(2) 0.5136(5) 0.0670(13) Uani 1 1 d . . . . .
C11 C 0.8764(9) 0.4157(2) 0.6113(4) 0.0703(13) Uani 1 1 d . . . . .
C12 C 0.7281(9) 0.3841(3) 0.6854(5) 0.0733(14) Uani 1 1 d . . . . .
C13 C 0.5541(9) 0.3460(2) 0.6290(5) 0.0741(14) Uani 1 1 d . . . . .
C14 C 0.3809(11) 0.3094(3) 0.6767(7) 0.0882(19) Uani 1 1 d . . . . .
H14 H 0.2666 0.2841 0.6384 0.106 Uiso 1 1 calc R U . . .
C15 C 0.3855(13) 0.3121(4) 0.7845(7) 0.098(2) Uani 1 1 d . . . . .
H15 H 0.2702 0.2888 0.8191 0.118 Uiso 1 1 calc R U . . .
C16 C 0.5595(13) 0.3492(4) 0.8408(6) 0.0969(19) Uani 1 1 d . . . . .
H16 H 0.5611 0.3499 0.9127 0.116 Uiso 1 1 calc R U . . .
C17 C 0.7323(12) 0.3855(3) 0.7908(6) 0.0859(16) Uani 1 1 d . . . . .
H17 H 0.8487 0.4103 0.8289 0.103 Uiso 1 1 calc R U . . .
C18 C 1.0732(10) 0.4582(3) 0.6345(5) 0.0725(13) Uani 1 1 d . . . . .
O2 O 1.2357(8) 0.7077(2) 0.5991(4) 0.0958(14) Uani 1 1 d . . . . .
N4 N 0.6585(8) 0.5903(2) 0.6393(4) 0.0711(11) Uani 1 1 d . . . . .
H4 H 0.5201 0.5713 0.6459 0.085 Uiso 1 1 calc R U . . .
N5 N 0.9317(7) 0.64303(19) 0.5318(4) 0.0699(11) Uani 1 1 d . . . . .
N6 N 0.2913(10) 0.4998(3) 0.4108(5) 0.0925(15) Uani 1 1 d . . . . .
C19 C 1.0548(10) 0.6761(3) 0.6117(5) 0.0771(15) Uani 1 1 d . . . . .
C20 C 0.9330(12) 0.6725(3) 0.7101(5) 0.0891(17) Uani 1 1 d . . . . .
H20A H 0.8108 0.7067 0.7102 0.107 Uiso 1 1 calc R U . . .
H20B H 1.0545 0.6813 0.7666 0.107 Uiso 1 1 calc R U . . .
C21 C 0.8095(11) 0.6087(3) 0.7313(5) 0.0768(14) Uani 1 1 d . . . . .
H21 H 0.9373 0.5756 0.7437 0.092 Uiso 1 1 calc R U . . .
C22 C 0.6597(9) 0.6117(2) 0.8260(3) 0.0796(14) Uani 1 1 d G . . . .
C23 C 0.5542(13) 0.6690(2) 0.8585(5) 0.144(3) Uani 1 1 d G U . . .
H23 H 0.5736 0.7073 0.8217 0.172 Uiso 1 1 calc R U . . .
C24 C 0.4196(14) 0.6691(3) 0.9459(5) 0.151(3) Uani 1 1 d G U . . .
H24 H 0.3489 0.7074 0.9677 0.181 Uiso 1 1 calc R U . . .
C25 C 0.3905(14) 0.6119(4) 1.0008(5) 0.151(3) Uani 1 1 d G U . . .
H25 H 0.3005 0.6119 1.0593 0.181 Uiso 1 1 calc R U . . .
C26 C 0.4961(17) 0.5546(3) 0.9684(6) 0.167(3) Uani 1 1 d G U . . .
H26 H 0.4767 0.5163 1.0051 0.200 Uiso 1 1 calc R U . . .
C27 C 0.6307(14) 0.5545(2) 0.8809(5) 0.160(3) Uani 1 1 d G U . . .
H27 H 0.7013 0.5162 0.8592 0.191 Uiso 1 1 calc R U . . .
C28 C 0.7299(9) 0.6023(2) 0.5450(4) 0.0666(13) Uani 1 1 d . . . . .
C29 C 0.6346(9) 0.5827(2) 0.4485(4) 0.0665(12) Uani 1 1 d . . . . .
C30 C 0.7758(10) 0.6137(2) 0.3706(5) 0.0696(13) Uani 1 1 d . . . . .
C31 C 0.9616(10) 0.6498(2) 0.4239(5) 0.0706(14) Uani 1 1 d . . . . .
C32 C 1.1329(11) 0.6852(3) 0.3724(6) 0.0850(17) Uani 1 1 d . . . . .
H32 H 1.2582 0.7082 0.4081 0.102 Uiso 1 1 calc R U . . .
C33 C 1.1081(13) 0.6843(3) 0.2662(6) 0.0950(19) Uani 1 1 d . . . . .
H33 H 1.2193 0.7075 0.2293 0.114 Uiso 1 1 calc R U . . .
C34 C 0.9219(13) 0.6498(3) 0.2119(6) 0.0959(19) Uani 1 1 d . . . . .
H34 H 0.9099 0.6509 0.1399 0.115 Uiso 1 1 calc R U . . .
C35 C 0.7553(12) 0.6140(3) 0.2633(5) 0.0848(16) Uani 1 1 d . . . . .
H35 H 0.6320 0.5906 0.2269 0.102 Uiso 1 1 calc R U . . .
C36 C 0.4426(10) 0.5383(3) 0.4279(5) 0.0725(13) Uani 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'
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_
_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
C10 N1 C3 117.8(4) . . ?
C10 N1 H1 121.1 . . ?
C3 N1 H1 121.1 . . ?
C1 N2 C10 123.0(5) . . ?
C1 N2 C13 127.5(5) . . ?
C10 N2 C13 109.1(4) . . ?
O1 C1 N2 120.5(6) . . ?
O1 C1 C2 124.5(5) . . ?
N2 C1 C2 115.0(5) . . ?
C1 C2 C3 112.7(5) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 112.4(4) . . ?
N1 C3 C2 107.4(5) . . ?
C4 C3 C2 113.7(5) . . ?
N1 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C9 C4 C5 117.5(7) . . ?
C9 C4 C3 122.7(6) . . ?
C5 C4 C3 119.7(6) . . ?
C4 C5 C6 122.0(8) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 121.0(9) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 117.0(9) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
C9 C8 C7 122.0(9) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C4 C9 C8 120.4(8) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
N1 C10 C11 132.1(5) . . ?
N1 C10 N2 119.5(5) . . ?
C11 C10 N2 108.5(5) . . ?
C10 C11 C18 125.9(5) . . ?
C10 C11 C12 107.8(5) . . ?
C18 C11 C12 126.3(5) . . ?
C17 C12 C13 119.9(5) . . ?
C17 C12 C11 132.8(5) . . ?
C13 C12 C11 107.3(5) . . ?
C14 C13 C12 122.2(6) . . ?
C14 C13 N2 130.4(6) . . ?
C12 C13 N2 107.4(5) . . ?
C13 C14 C15 117.2(6) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C16 C15 C14 120.9(7) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.7(7) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C12 C17 C16 119.1(6) . . ?
C12 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
N3 C18 C11 177.9(7) . . ?
C28 N4 C21 121.3(5) . . ?
C28 N4 H4 119.4 . . ?
C21 N4 H4 119.4 . . ?
C19 N5 C28 123.5(5) . . ?
C19 N5 C31 127.3(5) . . ?
C28 N5 C31 108.7(4) . . ?
O2 C19 N5 122.0(6) . . ?
O2 C19 C20 124.4(6) . . ?
N5 C19 C20 113.5(5) . . ?
C19 C20 C21 115.5(5) . . ?
C19 C20 H20A 108.4 . . ?
C21 C20 H20A 108.4 . . ?
C19 C20 H20B 108.4 . . ?
C21 C20 H20B 108.4 . . ?
H20A C20 H20B 107.5 . . ?
N4 C21 C20 108.3(5) . . ?
N4 C21 C22 111.4(5) . . ?
C20 C21 C22 112.4(5) . . ?
N4 C21 H21 108.2 . . ?
C20 C21 H21 108.2 . . ?
C22 C21 H21 108.2 . . ?
C23 C22 C27 120.0 . . ?
C23 C22 C21 122.4(4) . . ?
C27 C22 C21 117.6(4) . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C22 120.0 . . ?
C26 C27 H27 120.0 . . ?
C22 C27 H27 120.0 . . ?
N4 C28 C29 131.4(5) . . ?
N4 C28 N5 120.2(5) . . ?
C29 C28 N5 108.4(5) . . ?
C28 C29 C36 126.4(5) . . ?
C28 C29 C30 108.3(5) . . ?
C36 C29 C30 125.3(5) . . ?
C35 C30 C31 119.9(5) . . ?
C35 C30 C29 133.2(5) . . ?
C31 C30 C29 106.9(5) . . ?
C32 C31 C30 122.0(6) . . ?
C32 C31 N5 130.3(5) . . ?
C30 C31 N5 107.7(4) . . ?
C33 C32 C31 116.7(6) . . ?
C33 C32 H32 121.7 . . ?
C31 C32 H32 121.7 . . ?
C32 C33 C34 122.2(6) . . ?
C32 C33 H33 118.9 . . ?
C34 C33 H33 118.9 . . ?
C35 C34 C33 120.9(7) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C34 C35 C30 118.4(7) . . ?
C34 C35 H35 120.8 . . ?
C30 C35 H35 120.8 . . ?
N6 C36 C29 177.3(6) . . ?
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 C1 1.222(7) . ?
N1 C10 1.339(8) . ?
N1 C3 1.458(7) . ?
N1 H1 0.8600 . ?
N2 C1 1.397(7) . ?
N2 C10 1.396(6) . ?
N2 C13 1.410(8) . ?
N3 C18 1.154(7) . ?
C1 C2 1.490(9) . ?
C2 C3 1.516(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.501(9) . ?
C3 H3 0.9800 . ?
C4 C9 1.356(9) . ?
C4 C5 1.358(9) . ?
C5 C6 1.388(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.336(14) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(15) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(13) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.379(8) . ?
C11 C18 1.401(8) . ?
C11 C12 1.450(8) . ?
C12 C17 1.363(9) . ?
C12 C13 1.399(8) . ?
C13 C14 1.386(8) . ?
C14 C15 1.395(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.397(10) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
O2 C19 1.203(7) . ?
N4 C28 1.329(7) . ?
N4 C21 1.452(7) . ?
N4 H4 0.8600 . ?
N5 C19 1.375(7) . ?
N5 C28 1.405(6) . ?
N5 C31 1.424(7) . ?
N6 C36 1.155(7) . ?
C19 C20 1.478(9) . ?
C20 C21 1.511(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.520(7) . ?
C21 H21 0.9800 . ?
C22 C23 1.3900 . ?
C22 C27 1.3900 . ?
C23 C24 1.3900 . ?
C23 H23 0.9300 . ?
C24 C25 1.3900 . ?
C24 H24 0.9300 . ?
C25 C26 1.3900 . ?
C25 H25 0.9300 . ?
C26 C27 1.3900 . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.381(8) . ?
C29 C36 1.403(7) . ?
C29 C30 1.457(8) . ?
C30 C35 1.385(9) . ?
C30 C31 1.401(8) . ?
C31 C32 1.390(8) . ?
C32 C33 1.372(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.392(10) . ?
C33 H33 0.9300 . ?
C34 C35 1.376(9) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
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
C32 H32 O2 0.93 2.48 2.986(9) 114.1 .
C21 H21 N3 0.98 2.63 3.484(8) 145.2 .
N4 H4 N3 0.86 2.25 3.081(7) 161.9 1_455
C14 H14 O1 0.93 2.44 2.956(10) 115.1 .
C3 H3 O2 0.98 2.55 3.309(7) 134.6 2_746
C3 H3 O1 0.98 2.45 3.236(7) 136.4 1_655
N1 H1 N6 0.86 2.21 2.986(7) 150.6 1_655
N1 H1 N6 0.86 2.21 2.986(7) 150.6 1_655
C3 H3 O1 0.98 2.45 3.236(7) 136.4 1_655
C3 H3 O2 0.98 2.55 3.309(7) 134.6 2_746
C14 H14 O1 0.93 2.44 2.956(10) 115.1 .
N4 H4 N3 0.86 2.25 3.081(7) 161.9 1_455
C21 H21 N3 0.98 2.63 3.484(8) 145.2 .
C32 H32 O2 0.93 2.48 2.986(9) 114.1 .
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 N2 C1 O1 -177.0(5) . . . . ?
C13 N2 C1 O1 -4.5(8) . . . . ?
C10 N2 C1 C2 1.5(7) . . . . ?
C13 N2 C1 C2 173.9(5) . . . . ?
O1 C1 C2 C3 -152.0(5) . . . . ?
N2 C1 C2 C3 29.6(6) . . . . ?
C10 N1 C3 C4 177.4(5) . . . . ?
C10 N1 C3 C2 51.6(6) . . . . ?
C1 C2 C3 N1 -53.9(6) . . . . ?
C1 C2 C3 C4 -178.9(5) . . . . ?
N1 C3 C4 C9 -24.9(9) . . . . ?
C2 C3 C4 C9 97.4(8) . . . . ?
N1 C3 C4 C5 151.7(6) . . . . ?
C2 C3 C4 C5 -86.0(7) . . . . ?
C9 C4 C5 C6 -0.3(11) . . . . ?
C3 C4 C5 C6 -177.1(7) . . . . ?
C4 C5 C6 C7 -0.1(15) . . . . ?
C5 C6 C7 C8 1.5(18) . . . . ?
C6 C7 C8 C9 -2.6(19) . . . . ?
C5 C4 C9 C8 -0.8(13) . . . . ?
C3 C4 C9 C8 175.9(9) . . . . ?
C7 C8 C9 C4 2.3(18) . . . . ?
C3 N1 C10 C11 156.4(5) . . . . ?
C3 N1 C10 N2 -22.7(7) . . . . ?
C1 N2 C10 N1 -6.3(7) . . . . ?
C13 N2 C10 N1 180.0(4) . . . . ?
C1 N2 C10 C11 174.4(4) . . . . ?
C13 N2 C10 C11 0.7(5) . . . . ?
N1 C10 C11 C18 -0.2(9) . . . . ?
N2 C10 C11 C18 178.9(5) . . . . ?
N1 C10 C11 C12 -179.1(5) . . . . ?
N2 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C17 178.9(6) . . . . ?
C18 C11 C12 C17 0.0(10) . . . . ?
C10 C11 C12 C13 -0.9(6) . . . . ?
C18 C11 C12 C13 -179.7(5) . . . . ?
C17 C12 C13 C14 0.7(8) . . . . ?
C11 C12 C13 C14 -179.5(5) . . . . ?
C17 C12 C13 N2 -178.5(5) . . . . ?
C11 C12 C13 N2 1.3(5) . . . . ?
C1 N2 C13 C14 6.3(9) . . . . ?
C10 N2 C13 C14 179.7(5) . . . . ?
C1 N2 C13 C12 -174.6(5) . . . . ?
C10 N2 C13 C12 -1.3(5) . . . . ?
C12 C13 C14 C15 0.3(8) . . . . ?
N2 C13 C14 C15 179.2(5) . . . . ?
C13 C14 C15 C16 -1.1(9) . . . . ?
C14 C15 C16 C17 1.0(11) . . . . ?
C13 C12 C17 C16 -0.8(8) . . . . ?
C11 C12 C17 C16 179.5(6) . . . . ?
C15 C16 C17 C12 0.0(10) . . . . ?
C28 N5 C19 O2 175.6(5) . . . . ?
C31 N5 C19 O2 -13.0(9) . . . . ?
C28 N5 C19 C20 -8.6(7) . . . . ?
C31 N5 C19 C20 162.8(5) . . . . ?
O2 C19 C20 C21 -148.1(6) . . . . ?
N5 C19 C20 C21 36.2(8) . . . . ?
C28 N4 C21 C20 36.5(7) . . . . ?
C28 N4 C21 C22 160.6(5) . . . . ?
C19 C20 C21 N4 -48.7(7) . . . . ?
C19 C20 C21 C22 -172.2(5) . . . . ?
N4 C21 C22 C23 -93.6(6) . . . . ?
C20 C21 C22 C23 28.2(7) . . . . ?
N4 C21 C22 C27 86.6(6) . . . . ?
C20 C21 C22 C27 -151.6(5) . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C21 C22 C23 C24 -179.8(5) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C22 0.0 . . . . ?
C23 C22 C27 C26 0.0 . . . . ?
C21 C22 C27 C26 179.8(5) . . . . ?
C21 N4 C28 C29 170.9(5) . . . . ?
C21 N4 C28 N5 -11.3(7) . . . . ?
C19 N5 C28 N4 -4.7(7) . . . . ?
C31 N5 C28 N4 -177.4(4) . . . . ?
C19 N5 C28 C29 173.5(5) . . . . ?
C31 N5 C28 C29 0.8(5) . . . . ?
N4 C28 C29 C36 -6.6(9) . . . . ?
N5 C28 C29 C36 175.4(5) . . . . ?
N4 C28 C29 C30 176.1(5) . . . . ?
N5 C28 C29 C30 -1.8(6) . . . . ?
C28 C29 C30 C35 -176.7(6) . . . . ?
C36 C29 C30 C35 6.0(9) . . . . ?
C28 C29 C30 C31 2.2(6) . . . . ?
C36 C29 C30 C31 -175.1(5) . . . . ?
C35 C30 C31 C32 -1.8(8) . . . . ?
C29 C30 C31 C32 179.2(5) . . . . ?
C35 C30 C31 N5 177.3(5) . . . . ?
C29 C30 C31 N5 -1.7(5) . . . . ?
C19 N5 C31 C32 7.2(9) . . . . ?
C28 N5 C31 C32 179.6(5) . . . . ?
C19 N5 C31 C30 -171.8(5) . . . . ?
C28 N5 C31 C30 0.7(5) . . . . ?
C30 C31 C32 C33 1.5(8) . . . . ?
N5 C31 C32 C33 -177.3(6) . . . . ?
C31 C32 C33 C34 -0.2(10) . . . . ?
C32 C33 C34 C35 -0.9(11) . . . . ?
C33 C34 C35 C30 0.7(10) . . . . ?
C31 C30 C35 C34 0.6(8) . . . . ?
C29 C30 C35 C34 179.4(6) . . . . ?
