#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:16:06 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289364 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/24/7132487.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_7132487
loop_
_publ_author_name
'Zhang, Xuan'
'Song, Xiaoxiao'
'Ni, Qijian'
_publ_section_title
;
 Organocatalytic regio- and enantioselective C1-arylation of
 β,γ-alkynyl-α-imino esters with
 pyrrolo[2,1-a]isoquinolines.
;
_journal_issue                   7
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              831
_journal_page_last               834
_journal_paper_doi               10.1039/d3cc04946a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C31 H30 N2 O6'
_chemical_formula_sum            'C31 H30 N2 O6'
_chemical_formula_weight         526.57
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-09 deposited with the CCDC.	2023-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                105.430(3)
_cell_angle_beta                 99.759(3)
_cell_angle_gamma                108.874(4)
_cell_formula_units_Z            2
_cell_length_a                   10.1018(8)
_cell_length_b                   11.4504(7)
_cell_length_c                   13.7104(12)
_cell_measurement_reflns_used    3536
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      29.684
_cell_measurement_theta_min      3.083
_cell_volume                     1388.58(19)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.735
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.924
_diffrn_reflns_Laue_measured_fraction_max 0.735
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12577
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.134
_diffrn_reflns_theta_min         2.802
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0511 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.9223.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         7152
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0490
_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)+(0.0607P)²+0.1134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1398
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4171
_reflns_number_total             7152
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04946a2.cif
_cod_data_source_block           20220530c
_cod_depositor_comments
'Adding full bibliography for 7132486--7132487.cif.'
_cod_database_code               7132487
_shelx_shelxl_version_number     2019/2
_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_max   0.989
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
O6A \\sim O6 \\sim C30 \\sim C30A \\sim C31 \\sim C31A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 C29, O6, C30, C31
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C29, O6A, C30A, C31A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 Sof(O6A)=Sof(C30A)=Sof(H30C)=Sof(H30D)=Sof(C31A)=Sof(H31D)=Sof(H31E)=
 Sof(H31F)=1-FVAR(1)
 Sof(O6)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C30A(H30C,H30D)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C), C31(H31A,H31B,H31C), C31A(H31D,H31E,H31F)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.78021(13) 0.42084(12) 0.87454(9) 0.0508(3) Uani 1 1 d . . . . .
O2 O 0.74337(12) 0.59764(11) 0.96303(8) 0.0455(3) Uani 1 1 d . . . . .
O3 O 0.36397(13) 0.51327(12) 0.66909(9) 0.0502(3) Uani 1 1 d . . . . .
O4 O 0.30521(13) 0.59381(13) 0.81914(9) 0.0507(3) Uani 1 1 d . . . . .
O5 O 0.50398(14) 0.34957(12) 0.94314(9) 0.0526(3) Uani 1 1 d . . . . .
O6 O 0.3701(10) 0.1410(9) 0.8853(8) 0.0587(16) Uani 0.597(13) 1 d . U P A 1
N1 N 0.47895(13) 0.27274(12) 0.61606(9) 0.0347(3) Uani 1 1 d . . . . .
N2 N 0.48935(14) 0.53113(12) 0.82940(10) 0.0372(3) Uani 1 1 d . . . . .
H2 H 0.498680 0.556643 0.896025 0.045 Uiso 1 1 calc R U . . .
C1 C 0.50765(16) 0.33052(14) 0.72309(11) 0.0340(3) Uani 1 1 d . . . . .
C2 C 0.44386(16) 0.23057(15) 0.76059(12) 0.0376(3) Uani 1 1 d . . . . .
C3 C 0.37766(17) 0.11105(15) 0.67503(13) 0.0418(4) Uani 1 1 d . . . . .
H3 H 0.327956 0.028987 0.678590 0.050 Uiso 1 1 calc R U . . .
C4 C 0.39916(16) 0.13669(15) 0.58600(12) 0.0376(3) Uani 1 1 d . . . . .
C5 C 0.35858(16) 0.05454(15) 0.47736(13) 0.0407(4) Uani 1 1 d . . . . .
C6 C 0.28195(19) -0.08177(17) 0.44367(15) 0.0518(4) Uani 1 1 d . . . . .
H6 H 0.254393 -0.121573 0.491975 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2473(2) -0.15707(19) 0.33892(16) 0.0607(5) Uani 1 1 d . . . . .
H7 H 0.196993 -0.247583 0.317274 0.073 Uiso 1 1 calc R U . . .
C8 C 0.2863(2) -0.0997(2) 0.26569(15) 0.0625(6) Uani 1 1 d . . . . .
H8 H 0.261818 -0.151424 0.195226 0.075 Uiso 1 1 calc R U . . .
C9 C 0.3614(2) 0.03375(19) 0.29725(14) 0.0551(5) Uani 1 1 d . . . . .
H9 H 0.387459 0.072057 0.247818 0.066 Uiso 1 1 calc R U . . .
C10 C 0.39929(17) 0.11310(16) 0.40348(12) 0.0429(4) Uani 1 1 d . . . . .
C11 C 0.47680(18) 0.25298(17) 0.43946(13) 0.0441(4) Uani 1 1 d . . . . .
H11 H 0.502558 0.292339 0.390538 0.053 Uiso 1 1 calc R U . . .
C12 C 0.51331(17) 0.32865(16) 0.53986(12) 0.0401(4) Uani 1 1 d . . . . .
H12 H 0.561907 0.419154 0.559504 0.048 Uiso 1 1 calc R U . . .
C13 C 0.58925(16) 0.47556(14) 0.78876(11) 0.0331(3) Uani 1 1 d . . . . .
C14 C 0.71348(16) 0.49007(15) 0.88139(12) 0.0370(3) Uani 1 1 d . . . . .
C15 C 0.8601(2) 0.6255(2) 1.05348(15) 0.0667(6) Uani 1 1 d . . . . .
H15A H 0.943157 0.618836 1.030975 0.100 Uiso 1 1 calc R U . . .
H15B H 0.828723 0.563363 1.088348 0.100 Uiso 1 1 calc R U . . .
H15C H 0.886105 0.712817 1.101312 0.100 Uiso 1 1 calc R U . . .
C16 C 0.67365(16) 0.56048(15) 0.73769(12) 0.0366(3) Uani 1 1 d . . . . .
C17 C 0.75210(17) 0.64114(15) 0.71118(12) 0.0394(4) Uani 1 1 d . . . . .
C18 C 0.84040(16) 0.73629(15) 0.67358(12) 0.0380(3) Uani 1 1 d . . . . .
C19 C 0.92509(18) 0.86369(17) 0.74232(14) 0.0486(4) Uani 1 1 d . . . . .
H19 H 0.926515 0.887210 0.812971 0.058 Uiso 1 1 calc R U . . .
C20 C 1.0070(2) 0.95499(18) 0.70507(17) 0.0591(5) Uani 1 1 d . . . . .
H20 H 1.064095 1.040005 0.751086 0.071 Uiso 1 1 calc R U . . .
C21 C 1.0050(2) 0.9218(2) 0.60156(18) 0.0623(5) Uani 1 1 d . . . . .
H21 H 1.060535 0.984205 0.577350 0.075 Uiso 1 1 calc R U . . .
C22 C 0.9215(2) 0.7969(2) 0.53306(16) 0.0609(5) Uani 1 1 d . . . . .
H22 H 0.920005 0.774784 0.462411 0.073 Uiso 1 1 calc R U . . .
C23 C 0.83966(19) 0.70380(18) 0.56850(14) 0.0504(4) Uani 1 1 d . . . . .
H23 H 0.783721 0.618904 0.521816 0.061 Uiso 1 1 calc R U . . .
C24 C 0.38301(16) 0.54259(15) 0.76323(12) 0.0375(3) Uani 1 1 d . . . . .
C25 C 0.18564(19) 0.62459(19) 0.76918(15) 0.0526(5) Uani 1 1 d . . . . .
C26 C 0.0676(2) 0.5018(3) 0.6896(2) 0.0896(8) Uani 1 1 d . . . . .
H26A H 0.101762 0.471538 0.630370 0.134 Uiso 1 1 calc R U . . .
H26B H -0.016321 0.520049 0.666382 0.134 Uiso 1 1 calc R U . . .
H26C H 0.041616 0.435134 0.721075 0.134 Uiso 1 1 calc R U . . .
C27 C 0.2445(3) 0.7296(2) 0.7237(2) 0.0780(7) Uani 1 1 d . . . . .
H27A H 0.329337 0.799741 0.774760 0.117 Uiso 1 1 calc R U . . .
H27B H 0.171611 0.762995 0.705536 0.117 Uiso 1 1 calc R U . . .
H27C H 0.270324 0.693229 0.661648 0.117 Uiso 1 1 calc R U . . .
C28 C 0.1320(3) 0.6750(3) 0.86221(19) 0.0820(7) Uani 1 1 d . . . . .
H28A H 0.092577 0.605379 0.888558 0.123 Uiso 1 1 calc R U . . .
H28B H 0.057694 0.705240 0.840141 0.123 Uiso 1 1 calc R U . . .
H28C H 0.211783 0.746368 0.916827 0.123 Uiso 1 1 calc R U . . .
C29 C 0.44830(18) 0.24698(17) 0.87032(13) 0.0434(4) Uani 1 1 d . . . . .
C30 C 0.3981(10) 0.1194(9) 0.9842(6) 0.0709(18) Uani 0.597(13) 1 d . U P A 1
H30A H 0.469429 0.197930 1.039976 0.085 Uiso 0.597(13) 1 calc R U P A 1
H30B H 0.430168 0.047313 0.978743 0.085 Uiso 0.597(13) 1 calc R U P A 1
C31 C 0.2478(7) 0.0856(9) 1.0005(4) 0.0864(18) Uani 0.597(13) 1 d . U P A 1
H31A H 0.181658 0.004407 0.946694 0.130 Uiso 0.597(13) 1 calc R U P A 1
H31B H 0.214693 0.154439 0.996729 0.130 Uiso 0.597(13) 1 calc R U P A 1
H31C H 0.251679 0.076623 1.068453 0.130 Uiso 0.597(13) 1 calc R U P A 1
O6A O 0.4005(16) 0.1193(14) 0.8779(12) 0.059(2) Uani 0.403(13) 1 d . U P A 2
C30A C 0.3676(12) 0.1519(10) 0.9952(8) 0.0515(17) Uani 0.403(13) 1 d . U P A 2
H30C H 0.457045 0.190709 1.052236 0.062 Uiso 0.403(13) 1 calc R U P A 2
H30D H 0.315357 0.209966 1.003350 0.062 Uiso 0.403(13) 1 calc R U P A 2
C31A C 0.2771(15) 0.0201(11) 0.9907(6) 0.103(4) Uani 0.403(13) 1 d . U P A 2
H31D H 0.309560 -0.043232 0.952094 0.155 Uiso 0.403(13) 1 calc R U P A 2
H31E H 0.177228 -0.000749 0.955989 0.155 Uiso 0.403(13) 1 calc R U P A 2
H31F H 0.285222 0.018026 1.060917 0.155 Uiso 0.403(13) 1 calc R U P A 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
C14 O2 C15 116.18(14) . . ?
C24 O4 C25 121.93(13) . . ?
C29 O6 C30 123.1(9) . . ?
C1 N1 C4 109.60(12) . . ?
C1 N1 C12 130.31(13) . . ?
C12 N1 C4 120.07(13) . . ?
C13 N2 H2 119.7 . . ?
C24 N2 H2 119.7 . . ?
C24 N2 C13 120.58(12) . . ?
N1 C1 C2 106.61(12) . . ?
N1 C1 C13 127.40(13) . . ?
C2 C1 C13 125.97(13) . . ?
C1 C2 C3 108.48(14) . . ?
C1 C2 C29 125.52(14) . . ?
C3 C2 C29 125.99(14) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 C2 108.08(14) . . ?
C4 C3 H3 126.0 . . ?
N1 C4 C5 119.77(14) . . ?
C3 C4 N1 107.23(13) . . ?
C3 C4 C5 133.00(15) . . ?
C6 C5 C4 122.05(16) . . ?
C6 C5 C10 119.25(15) . . ?
C10 C5 C4 118.70(15) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.10(19) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.86(19) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.85(17) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.69(19) . . ?
C10 C9 H9 119.7 . . ?
C5 C10 C9 119.25(17) . . ?
C5 C10 C11 118.38(14) . . ?
C9 C10 C11 122.37(17) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 C10 122.72(16) . . ?
C12 C11 H11 118.6 . . ?
N1 C12 H12 119.9 . . ?
C11 C12 N1 120.29(15) . . ?
C11 C12 H12 119.9 . . ?
N2 C13 C1 110.36(12) . . ?
N2 C13 C14 110.44(12) . . ?
N2 C13 C16 109.25(12) . . ?
C1 C13 C14 108.84(12) . . ?
C16 C13 C1 116.76(12) . . ?
C16 C13 C14 100.76(12) . . ?
O1 C14 O2 125.69(15) . . ?
O1 C14 C13 123.61(14) . . ?
O2 C14 C13 110.31(13) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C13 170.45(16) . . ?
C16 C17 C18 176.69(17) . . ?
C19 C18 C17 120.04(15) . . ?
C23 C18 C17 120.86(15) . . ?
C23 C18 C19 119.08(15) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.63(17) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.68(18) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.18(18) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.21(19) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.21(17) . . ?
C22 C23 H23 119.9 . . ?
O3 C24 O4 126.23(14) . . ?
O3 C24 N2 124.58(14) . . ?
O4 C24 N2 109.17(13) . . ?
O4 C25 C26 110.19(16) . . ?
O4 C25 C27 109.90(15) . . ?
O4 C25 C28 101.76(15) . . ?
C26 C25 C27 113.2(2) . . ?
C26 C25 C28 110.03(19) . . ?
C27 C25 C28 111.19(18) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O5 C29 O6 119.4(4) . . ?
O5 C29 C2 125.77(15) . . ?
O5 C29 O6A 126.0(6) . . ?
O6 C29 C2 114.4(4) . . ?
O6A C29 C2 107.2(6) . . ?
O6 C30 H30A 111.8 . . ?
O6 C30 H30B 111.8 . . ?
O6 C30 C31 99.9(9) . . ?
H30A C30 H30B 109.5 . . ?
C31 C30 H30A 111.8 . . ?
C31 C30 H30B 111.8 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 O6A C30A 100.6(9) . . ?
O6A C30A H30C 111.5 . . ?
O6A C30A H30D 111.5 . . ?
H30C C30A H30D 109.3 . . ?
C31A C30A O6A 101.5(10) . . ?
C31A C30A H30C 111.5 . . ?
C31A C30A H30D 111.5 . . ?
C30A C31A H31D 109.5 . . ?
C30A C31A H31E 109.5 . . ?
C30A C31A H31F 109.5 . . ?
H31D C31A H31E 109.5 . . ?
H31D C31A H31F 109.5 . . ?
H31E C31A H31F 109.5 . . ?
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
O1 C14 1.1912(18) . ?
O2 C14 1.3313(18) . ?
O2 C15 1.442(2) . ?
O3 C24 1.2078(18) . ?
O4 C24 1.3463(18) . ?
O4 C25 1.4751(19) . ?
O5 C29 1.205(2) . ?
O6 C29 1.307(11) . ?
O6 C30 1.439(16) . ?
N1 C1 1.3748(18) . ?
N1 C4 1.4071(19) . ?
N1 C12 1.399(2) . ?
N2 H2 0.8600 . ?
N2 C13 1.4667(18) . ?
N2 C24 1.3485(19) . ?
C1 C2 1.392(2) . ?
C1 C13 1.522(2) . ?
C2 C3 1.408(2) . ?
C2 C29 1.457(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(2) . ?
C4 C5 1.439(2) . ?
C5 C6 1.401(2) . ?
C5 C10 1.403(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.405(2) . ?
C10 C11 1.435(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.330(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.558(2) . ?
C13 C16 1.480(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.190(2) . ?
C17 C18 1.440(2) . ?
C18 C19 1.391(2) . ?
C18 C23 1.387(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.363(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.377(3) . ?
C23 H23 0.9300 . ?
C25 C26 1.499(3) . ?
C25 C27 1.500(3) . ?
C25 C28 1.516(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 O6A 1.422(16) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.512(11) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
O6A C30A 1.666(19) . ?
C30A H30C 0.9700 . ?
C30A H30D 0.9700 . ?
C30A C31A 1.468(15) . ?
C31A H31D 0.9600 . ?
C31A H31E 0.9600 . ?
C31A H31F 0.9600 . ?
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
O5 C29 O6A C30A 26.0(12) . . . . ?
N1 C1 C2 C3 0.74(17) . . . . ?
N1 C1 C2 C29 179.38(14) . . . . ?
N1 C1 C13 N2 111.62(16) . . . . ?
N1 C1 C13 C14 -127.04(15) . . . . ?
N1 C1 C13 C16 -13.9(2) . . . . ?
N1 C4 C5 C6 178.59(14) . . . . ?
N1 C4 C5 C10 -0.4(2) . . . . ?
N2 C13 C14 O1 155.74(15) . . . . ?
N2 C13 C14 O2 -31.04(17) . . . . ?
C1 N1 C4 C3 0.55(17) . . . . ?
C1 N1 C4 C5 -178.83(13) . . . . ?
C1 N1 C12 C11 178.76(15) . . . . ?
C1 C2 C3 C4 -0.42(18) . . . . ?
C1 C2 C29 O5 2.3(3) . . . . ?
C1 C2 C29 O6 174.4(5) . . . . ?
C1 C2 C29 O6A -166.9(6) . . . . ?
C1 C13 C14 O1 34.4(2) . . . . ?
C1 C13 C14 O2 -152.34(12) . . . . ?
C2 C1 C13 N2 -66.56(18) . . . . ?
C2 C1 C13 C14 54.78(19) . . . . ?
C2 C1 C13 C16 167.91(14) . . . . ?
C2 C3 C4 N1 -0.07(18) . . . . ?
C2 C3 C4 C5 179.19(16) . . . . ?
C2 C29 O6A C30A -164.8(7) . . . . ?
C3 C2 C29 O5 -179.33(17) . . . . ?
C3 C2 C29 O6 -7.2(5) . . . . ?
C3 C2 C29 O6A 11.5(6) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C3 C4 C5 C10 -179.59(17) . . . . ?
C4 N1 C1 C2 -0.79(16) . . . . ?
C4 N1 C1 C13 -179.26(13) . . . . ?
C4 N1 C12 C11 -3.1(2) . . . . ?
C4 C5 C6 C7 -178.96(16) . . . . ?
C4 C5 C10 C9 179.44(14) . . . . ?
C4 C5 C10 C11 -1.4(2) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C5 C10 C11 C12 1.1(2) . . . . ?
C6 C5 C10 C9 0.4(2) . . . . ?
C6 C5 C10 C11 179.56(14) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C5 -0.5(3) . . . . ?
C8 C9 C10 C11 -179.56(16) . . . . ?
C9 C10 C11 C12 -179.84(16) . . . . ?
C10 C5 C6 C7 0.0(2) . . . . ?
C10 C11 C12 N1 1.2(2) . . . . ?
C12 N1 C1 C2 177.48(15) . . . . ?
C12 N1 C1 C13 -1.0(2) . . . . ?
C12 N1 C4 C3 -177.93(13) . . . . ?
C12 N1 C4 C5 2.7(2) . . . . ?
C13 N2 C24 O3 -2.3(2) . . . . ?
C13 N2 C24 O4 178.94(12) . . . . ?
C13 C1 C2 C3 179.24(14) . . . . ?
C13 C1 C2 C29 -2.1(2) . . . . ?
C15 O2 C14 O1 -5.0(2) . . . . ?
C15 O2 C14 C13 -178.08(14) . . . . ?
C16 C13 C14 O1 -88.87(17) . . . . ?
C16 C13 C14 O2 84.36(14) . . . . ?
C17 C18 C19 C20 -178.63(16) . . . . ?
C17 C18 C23 C22 178.16(16) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C18 C23 C22 -0.2(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C18 0.5(3) . . . . ?
C23 C18 C19 C20 -0.3(3) . . . . ?
C24 O4 C25 C26 61.9(2) . . . . ?
C24 O4 C25 C27 -63.5(2) . . . . ?
C24 O4 C25 C28 178.62(17) . . . . ?
C24 N2 C13 C1 -67.05(17) . . . . ?
C24 N2 C13 C14 172.56(13) . . . . ?
C24 N2 C13 C16 62.62(17) . . . . ?
C25 O4 C24 O3 -2.0(3) . . . . ?
C25 O4 C24 N2 176.76(14) . . . . ?
C29 O6 C30 C31 128.3(6) . . . . ?
C29 C2 C3 C4 -179.05(15) . . . . ?
C29 O6A C30A C31A 163.2(10) . . . . ?
C30 O6 C29 O5 -30.8(12) . . . . ?
C30 O6 C29 C2 156.5(9) . . . . ?
