#------------------------------------------------------------------------------
#$Date: 2021-10-06 15:49:43 +0200 (Wed 06 de Oct de 2021) $
#$Revision: 269625 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/89/7128948.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_7128948
loop_
_publ_author_name
'Li, Xiaohu'
'Huang, You'
_publ_section_title
;
 Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl
 allenoates: access to the synthesis of chromeno[4,3-b]pyrroles.
;
_journal_issue                   77
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9934
_journal_page_last               9937
_journal_paper_doi               10.1039/d1cc04199a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C27 H29 N O7'
_chemical_formula_sum            'C27 H29 N O7'
_chemical_formula_weight         479.51
_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
_audit_creation_date             2020-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                93.977(4)
_cell_angle_beta                 106.212(5)
_cell_angle_gamma                112.740(5)
_cell_formula_units_Z            2
_cell_length_a                   10.7992(6)
_cell_length_b                   10.9972(5)
_cell_length_c                   11.7181(7)
_cell_measurement_reflns_used    10540
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.9450
_cell_measurement_theta_min      1.8450
_cell_volume                     1207.49(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       CrystalClear(Rigaku,2008)
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0464043000
_diffrn_orient_matrix_UB_12      -0.0686620000
_diffrn_orient_matrix_UB_13      -0.0073271000
_diffrn_orient_matrix_UB_21      0.0262885000
_diffrn_orient_matrix_UB_22      -0.0177158000
_diffrn_orient_matrix_UB_23      -0.0445947000
_diffrn_orient_matrix_UB_31      0.0534617000
_diffrn_orient_matrix_UB_32      -0.0081632000
_diffrn_orient_matrix_UB_33      0.0457949000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18298
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.850
_diffrn_reflns_theta_min         1.847
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.018(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   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         8080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0472
_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)+(0.0487P)²+0.2101P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6225
_reflns_number_total             8080
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04199a2.cif
_cod_data_source_block           r20201022a
_cod_depositor_comments          'Adding full bibliography for 7128948.cif.'
_cod_original_cell_volume        1207.49(12)
_cod_database_code               7128948
_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_max   0.986
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 89.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.78
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B), C23(H23A,H23B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.648
_oxdiff_exptl_absorpt_empirical_full_min 0.564
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 0.90279(8) 0.45082(8) 0.11827(7) 0.02108(17) Uani 1 1 d . . . . .
O2 O 1.19942(9) 0.84657(8) 0.44945(8) 0.0277(2) Uani 1 1 d . . . . .
O3 O 1.14976(8) 0.75333(7) 0.60635(7) 0.01969(17) Uani 1 1 d . . . . .
O4 O 0.65635(10) 0.39119(9) 0.43496(8) 0.0290(2) Uani 1 1 d . . . . .
O5 O 0.43962(9) 0.22371(8) 0.33329(8) 0.02526(19) Uani 1 1 d . . . . .
O6 O 0.29002(9) 0.34469(9) 0.09707(8) 0.02561(19) Uani 1 1 d . . . . .
O7 O 0.37449(8) 0.47243(8) 0.28479(7) 0.02257(18) Uani 1 1 d . . . . .
N1 N 0.53854(10) 0.30466(9) 0.13718(9) 0.01786(19) Uani 1 1 d . . . . .
C1 C 0.57010(13) 0.21936(11) -0.11875(11) 0.0234(2) Uani 1 1 d . . . . .
H1A H 0.470735 0.195641 -0.144362 0.028 Uiso 1 1 calc R . . . .
C2 C 0.62369(14) 0.15522(12) -0.18534(11) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.561089 0.087474 -0.255439 0.033 Uiso 1 1 calc R . . . .
C3 C 0.76895(13) 0.19048(11) -0.14905(11) 0.0248(2) Uani 1 1 d . . . . .
H3 H 0.805651 0.146598 -0.194412 0.030 Uiso 1 1 calc R . . . .
C4 C 0.86049(12) 0.28918(11) -0.04720(11) 0.0212(2) Uani 1 1 d . . . . .
H4 H 0.960017 0.313952 -0.022950 0.025 Uiso 1 1 calc R . . . .
C5 C 0.80555(12) 0.35215(10) 0.01972(10) 0.0175(2) Uani 1 1 d . . . . .
C6 C 0.84805(11) 0.48652(10) 0.20825(10) 0.0164(2) Uani 1 1 d . . . . .
H6 H 0.819927 0.411374 0.252671 0.020 Uiso 1 1 calc R . . . .
C7 C 0.71894(11) 0.51501(10) 0.14902(9) 0.0161(2) Uani 1 1 d . . . . .
H7 H 0.746073 0.593770 0.108502 0.019 Uiso 1 1 calc R . . . .
C8 C 0.60350(11) 0.38854(10) 0.05773(10) 0.0168(2) Uani 1 1 d . . . . .
H8 H 0.531389 0.412131 0.001620 0.020 Uiso 1 1 calc R . . . .
C9 C 0.66018(12) 0.31805(10) -0.01488(10) 0.0173(2) Uani 1 1 d . . . . .
C10 C 0.97096(11) 0.60719(10) 0.29340(10) 0.0181(2) Uani 1 1 d . . . . .
H10 H 1.030177 0.671465 0.259183 0.022 Uiso 1 1 calc R . . . .
C11 C 1.00369(11) 0.63145(10) 0.41258(10) 0.0176(2) Uani 1 1 d . . . . .
H11 H 0.947352 0.569060 0.450084 0.021 Uiso 1 1 calc R . . . .
C12 C 1.12763(12) 0.75531(10) 0.48794(10) 0.0180(2) Uani 1 1 d . . . . .
C13 C 1.26504(12) 0.87022(11) 0.69374(10) 0.0222(2) Uani 1 1 d . . . . .
H13A H 1.324283 0.929943 0.651651 0.027 Uiso 1 1 calc R . . . .
H13B H 1.326281 0.840981 0.754432 0.027 Uiso 1 1 calc R . . . .
C14 C 1.20394(12) 0.94542(10) 0.75620(11) 0.0215(2) Uani 1 1 d . . . . .
C15 C 1.23528(13) 0.96335(11) 0.88112(11) 0.0242(2) Uani 1 1 d . . . . .
H15 H 1.295602 0.927706 0.927487 0.029 Uiso 1 1 calc R . . . .
C16 C 1.17891(15) 1.03320(12) 0.93889(12) 0.0311(3) Uani 1 1 d . . . . .
H16 H 1.201574 1.045841 1.024483 0.037 Uiso 1 1 calc R . . . .
C17 C 1.09011(17) 1.08408(13) 0.87183(14) 0.0382(3) Uani 1 1 d . . . . .
H17 H 1.051965 1.132061 0.911296 0.046 Uiso 1 1 calc R . . . .
C18 C 1.05664(18) 1.06516(14) 0.74701(14) 0.0404(4) Uani 1 1 d . . . . .
H18 H 0.994232 1.098858 0.700724 0.048 Uiso 1 1 calc R . . . .
C19 C 1.11414(15) 0.99708(13) 0.68954(12) 0.0317(3) Uani 1 1 d . . . . .
H19 H 1.092091 0.985606 0.604037 0.038 Uiso 1 1 calc R . . . .
C20 C 0.64640(12) 0.53561(10) 0.23983(10) 0.0177(2) Uani 1 1 d . . . . .
H20A H 0.604926 0.600508 0.218941 0.021 Uiso 1 1 calc R . . . .
H20B H 0.715570 0.569746 0.323309 0.021 Uiso 1 1 calc R . . . .
C21 C 0.52797(11) 0.39452(10) 0.22913(10) 0.0166(2) Uani 1 1 d . . . . .
C22 C 0.55173(12) 0.34024(11) 0.34652(10) 0.0191(2) Uani 1 1 d . . . . .
C23 C 0.44162(15) 0.15867(12) 0.43822(12) 0.0292(3) Uani 1 1 d . . . . .
H23A H 0.541033 0.178379 0.485890 0.035 Uiso 1 1 calc R . . . .
H23B H 0.387992 0.059947 0.410267 0.035 Uiso 1 1 calc R . . . .
C24 C 0.37568(16) 0.20915(14) 0.51683(13) 0.0333(3) Uani 1 1 d . . . . .
H24A H 0.277218 0.189314 0.469481 0.050 Uiso 1 1 calc GR . . . .
H24B H 0.430227 0.306585 0.545842 0.050 Uiso 1 1 calc GR . . . .
H24C H 0.376637 0.164425 0.586342 0.050 Uiso 1 1 calc GR . . . .
C25 C 0.38220(12) 0.39880(10) 0.19392(10) 0.0185(2) Uani 1 1 d . . . . .
C26 C 0.23765(12) 0.47902(12) 0.26790(11) 0.0242(2) Uani 1 1 d . . . . .
H26A H 0.195085 0.483456 0.182611 0.029 Uiso 1 1 calc R . . . .
H26B H 0.252646 0.561254 0.320707 0.029 Uiso 1 1 calc R . . . .
C27 C 0.13870(15) 0.35715(14) 0.29884(14) 0.0338(3) Uani 1 1 d . . . . .
H27A H 0.121206 0.276179 0.244323 0.051 Uiso 1 1 calc GR . . . .
H27B H 0.048361 0.363257 0.289520 0.051 Uiso 1 1 calc GR . . . .
H27C H 0.181835 0.352331 0.382911 0.051 Uiso 1 1 calc GR . . . .
H1 H 0.4516(17) 0.2401(16) 0.0947(14) 0.035(4) 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 0.0033 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
C5 O1 C6 116.44(8) . . ?
C12 O3 C13 117.70(9) . . ?
C22 O5 C23 117.07(9) . . ?
C25 O7 C26 116.63(9) . . ?
C8 N1 H1 111.3(10) . . ?
C21 N1 C8 107.24(8) . . ?
C21 N1 H1 109.9(10) . . ?
C2 C1 H1A 119.5 . . ?
C2 C1 C9 120.92(11) . . ?
C9 C1 H1A 119.5 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.78(11) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.32(10) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.49(11) . . ?
C5 C4 H4 120.3 . . ?
O1 C5 C4 116.31(10) . . ?
O1 C5 C9 122.55(9) . . ?
C9 C5 C4 121.12(10) . . ?
O1 C6 H6 109.5 . . ?
O1 C6 C7 110.91(8) . . ?
O1 C6 C10 104.49(8) . . ?
C7 C6 H6 109.5 . . ?
C10 C6 H6 109.5 . . ?
C10 C6 C7 112.72(8) . . ?
C6 C7 H7 110.9 . . ?
C6 C7 C20 112.21(9) . . ?
C8 C7 C6 108.50(8) . . ?
C8 C7 H7 110.9 . . ?
C8 C7 C20 103.09(8) . . ?
C20 C7 H7 110.9 . . ?
N1 C8 C7 102.12(8) . . ?
N1 C8 H8 109.6 . . ?
N1 C8 C9 111.82(8) . . ?
C7 C8 H8 109.6 . . ?
C9 C8 C7 113.76(9) . . ?
C9 C8 H8 109.6 . . ?
C1 C9 C8 121.42(10) . . ?
C5 C9 C1 118.36(10) . . ?
C5 C9 C8 120.21(9) . . ?
C6 C10 H10 117.4 . . ?
C11 C10 C6 125.10(10) . . ?
C11 C10 H10 117.4 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.36(10) . . ?
C12 C11 H11 119.8 . . ?
O2 C12 O3 124.23(10) . . ?
O2 C12 C11 125.35(10) . . ?
O3 C12 C11 110.42(9) . . ?
O3 C13 H13A 109.8 . . ?
O3 C13 H13B 109.8 . . ?
O3 C13 C14 109.51(9) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C15 C14 C13 120.50(10) . . ?
C15 C14 C19 118.99(11) . . ?
C19 C14 C13 120.51(11) . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.46(12) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.02(13) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.98(12) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.05(13) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.49(13) . . ?
C18 C19 H19 119.8 . . ?
C7 C20 H20A 110.7 . . ?
C7 C20 H20B 110.7 . . ?
C7 C20 C21 105.26(8) . . ?
H20A C20 H20B 108.8 . . ?
C21 C20 H20A 110.7 . . ?
C21 C20 H20B 110.7 . . ?
N1 C21 C20 105.17(8) . . ?
N1 C21 C22 106.93(8) . . ?
N1 C21 C25 112.74(9) . . ?
C22 C21 C20 112.95(9) . . ?
C25 C21 C20 110.29(8) . . ?
C25 C21 C22 108.75(9) . . ?
O4 C22 O5 125.16(11) . . ?
O4 C22 C21 125.46(10) . . ?
O5 C22 C21 109.33(9) . . ?
O5 C23 H23A 109.6 . . ?
O5 C23 H23B 109.6 . . ?
O5 C23 C24 110.07(10) . . ?
H23A C23 H23B 108.2 . . ?
C24 C23 H23A 109.6 . . ?
C24 C23 H23B 109.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O6 C25 O7 125.72(10) . . ?
O6 C25 C21 124.17(10) . . ?
O7 C25 C21 110.10(9) . . ?
O7 C26 H26A 109.7 . . ?
O7 C26 H26B 109.7 . . ?
O7 C26 C27 109.81(10) . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 C5 1.3718(13) . ?
O1 C6 1.4441(12) . ?
O2 C12 1.2117(13) . ?
O3 C12 1.3438(13) . ?
O3 C13 1.4558(13) . ?
O4 C22 1.2003(14) . ?
O5 C22 1.3417(14) . ?
O5 C23 1.4639(14) . ?
O6 C25 1.2045(13) . ?
O7 C25 1.3336(12) . ?
O7 C26 1.4662(14) . ?
N1 C8 1.4810(14) . ?
N1 C21 1.4693(13) . ?
N1 H1 0.899(16) . ?
C1 H1A 0.9500 . ?
C1 C2 1.3902(16) . ?
C1 C9 1.3947(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3879(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3827(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3959(15) . ?
C5 C9 1.3921(15) . ?
C6 H6 1.0000 . ?
C6 C7 1.5335(15) . ?
C6 C10 1.4944(14) . ?
C7 H7 1.0000 . ?
C7 C8 1.5301(14) . ?
C7 C20 1.5383(15) . ?
C8 H8 1.0000 . ?
C8 C9 1.5052(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3214(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.4799(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5042(16) . ?
C14 C15 1.3884(17) . ?
C14 C19 1.3921(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3923(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3867(19) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5519(14) . ?
C21 C22 1.5328(15) . ?
C21 C25 1.5322(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5048(18) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.4987(18) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
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
O1 C5 C9 C1 177.94(10) . . . . ?
O1 C5 C9 C8 -1.03(16) . . . . ?
O1 C6 C7 C8 59.46(11) . . . . ?
O1 C6 C7 C20 172.70(8) . . . . ?
O1 C6 C10 C11 -140.72(11) . . . . ?
O3 C13 C14 C15 119.89(11) . . . . ?
O3 C13 C14 C19 -59.55(14) . . . . ?
N1 C8 C9 C1 78.86(13) . . . . ?
N1 C8 C9 C5 -102.20(11) . . . . ?
N1 C21 C22 O4 107.66(12) . . . . ?
N1 C21 C22 O5 -69.84(10) . . . . ?
N1 C21 C25 O6 -6.39(15) . . . . ?
N1 C21 C25 O7 174.69(9) . . . . ?
C1 C2 C3 C4 -0.11(19) . . . . ?
C2 C1 C9 C5 0.84(17) . . . . ?
C2 C1 C9 C8 179.79(11) . . . . ?
C2 C3 C4 C5 0.70(18) . . . . ?
C3 C4 C5 O1 -178.81(10) . . . . ?
C3 C4 C5 C9 -0.53(17) . . . . ?
C4 C5 C9 C1 -0.24(16) . . . . ?
C4 C5 C9 C8 -179.20(10) . . . . ?
C5 O1 C6 C7 -50.37(11) . . . . ?
C5 O1 C6 C10 -172.09(9) . . . . ?
C6 O1 C5 C4 -161.23(9) . . . . ?
C6 O1 C5 C9 20.51(14) . . . . ?
C6 C7 C8 N1 80.19(10) . . . . ?
C6 C7 C8 C9 -40.46(12) . . . . ?
C6 C7 C20 C21 -92.63(10) . . . . ?
C6 C10 C11 C12 -179.48(9) . . . . ?
C7 C6 C10 C11 98.76(12) . . . . ?
C7 C8 C9 C1 -166.09(10) . . . . ?
C7 C8 C9 C5 12.84(14) . . . . ?
C7 C20 C21 N1 0.08(11) . . . . ?
C7 C20 C21 C22 116.34(9) . . . . ?
C7 C20 C21 C25 -121.74(9) . . . . ?
C8 N1 C21 C20 -25.42(11) . . . . ?
C8 N1 C21 C22 -145.74(9) . . . . ?
C8 N1 C21 C25 94.80(10) . . . . ?
C8 C7 C20 C21 23.91(10) . . . . ?
C9 C1 C2 C3 -0.68(19) . . . . ?
C10 C6 C7 C8 176.23(9) . . . . ?
C10 C6 C7 C20 -70.53(11) . . . . ?
C10 C11 C12 O2 6.41(17) . . . . ?
C10 C11 C12 O3 -173.91(10) . . . . ?
C12 O3 C13 C14 109.84(11) . . . . ?
C13 O3 C12 O2 1.80(15) . . . . ?
C13 O3 C12 C11 -177.88(8) . . . . ?
C13 C14 C15 C16 179.87(11) . . . . ?
C13 C14 C19 C18 179.32(12) . . . . ?
C14 C15 C16 C17 0.62(19) . . . . ?
C15 C14 C19 C18 -0.13(19) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C17 C18 C19 C14 1.0(2) . . . . ?
C19 C14 C15 C16 -0.68(18) . . . . ?
C20 C7 C8 N1 -38.96(10) . . . . ?
C20 C7 C8 C9 -159.61(9) . . . . ?
C20 C21 C22 O4 -7.55(15) . . . . ?
C20 C21 C22 O5 174.96(8) . . . . ?
C20 C21 C25 O6 110.84(12) . . . . ?
C20 C21 C25 O7 -68.08(11) . . . . ?
C21 N1 C8 C7 40.70(10) . . . . ?
C21 N1 C8 C9 162.70(9) . . . . ?
C22 O5 C23 C24 88.91(13) . . . . ?
C22 C21 C25 O6 -124.79(11) . . . . ?
C22 C21 C25 O7 56.29(11) . . . . ?
C23 O5 C22 O4 4.27(16) . . . . ?
C23 O5 C22 C21 -178.22(9) . . . . ?
C25 O7 C26 C27 82.56(13) . . . . ?
C25 C21 C22 O4 -130.33(11) . . . . ?
C25 C21 C22 O5 52.17(11) . . . . ?
C26 O7 C25 O6 4.91(16) . . . . ?
C26 O7 C25 C21 -176.20(9) . . . . ?
