#------------------------------------------------------------------------------
#$Date: 2022-11-07 07:26:04 +0200 (Mon, 07 Nov 2022) $
#$Revision: 278987 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/55/7245577.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_7245577
loop_
_publ_author_name
'González-Saiz, Beatriz'
'Pertejo, Pablo'
'Peña-Calleja, Pablo'
'Mielczarek, Marcin'
'Hermosilla, Tomás'
'Carreira-Barral, Israel'
'de Miguel, Olivia'
'Rodríguez-Vidal, Francisco'
'Quesada, Roberto'
'García-Valverde, María'
_publ_section_title
;
 Base-selective access to highly functionalized heterocycles from
 multicomponent Ugi adducts
;
_journal_issue                   20
_journal_name_full               'Green Chemistry'
_journal_page_first              7988
_journal_page_last               7995
_journal_paper_doi               10.1039/D2GC02896D
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C H Cl3, C30 H28 F N3 O5'
_chemical_formula_sum            'C31 H29 Cl3 F N3 O5'
_chemical_formula_weight         648.92
_chemical_name_systematic        7jdiast2
_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             2022-05-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-07-28 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                108.53(4)
_cell_angle_beta                 96.84(7)
_cell_angle_gamma                106.91(5)
_cell_formula_units_Z            2
_cell_length_a                   9.940(16)
_cell_length_b                   10.793(10)
_cell_length_c                   16.25(2)
_cell_measurement_reflns_used    6451
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      66.076
_cell_measurement_theta_min      2.953
_cell_volume                     1538(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      230(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29480
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.666
_diffrn_reflns_theta_max         66.666
_diffrn_reflns_theta_min         2.949
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.129
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0889 after correction.
The Ratio of minimum to maximum transmission is 0.6647.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform, hexane'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0657
_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)+(0.0915P)²+1.9055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.2160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3218
_reflns_number_total             5392
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc02896d2.cif
_cod_data_source_block           7jdiast2
_cod_depositor_comments
'Adding full bibliography for 7245575--7245579.cif.'
_cod_database_code               7245577
_shelx_shelxl_version_number     2016/6
_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   0.940
_shelx_estimated_absorpt_t_min   0.745
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C7(H7), C19(H19), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C23(H23A,H23B), C24(H24A,H24B), C22(H22A,H22B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C13(H13), C30(H30), C26(H26), C17(H17), C5(H5), C4(H4),
 C2(H2A), C14(H14), C29(H29), C27(H27), C3(H3A), C28(H28), C16(H16)
;
_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
Cl2 Cl -0.15516(17) 0.75651(16) 0.66092(9) 0.0931(5) Uani 1 1 d . . . . .
Cl1 Cl -0.36288(18) 0.64986(16) 0.49427(9) 0.0932(5) Uani 1 1 d . . . . .
Cl3 Cl -0.0782(2) 0.6312(2) 0.49665(15) 0.1286(8) Uani 1 1 d . . . . .
O5 O 0.4803(3) 0.6583(3) 0.08060(18) 0.0543(7) Uani 1 1 d . . . . .
O4 O 0.3900(3) 0.5053(3) 0.30591(18) 0.0561(7) Uani 1 1 d . . . . .
O3 O 0.0956(3) 0.3874(3) -0.04408(18) 0.0618(8) Uani 1 1 d . . . . .
N2 N 0.1391(3) 0.5325(3) 0.1014(2) 0.0493(8) Uani 1 1 d . . . . .
H2 H 0.072236 0.567445 0.093446 0.059 Uiso 1 1 calc R U . . .
N3 N 0.5802(4) 0.7345(3) 0.2284(2) 0.0555(9) Uani 1 1 d . . . . .
H3 H 0.574409 0.717316 0.276923 0.067 Uiso 1 1 calc R U . . .
O2 O 0.1335(4) 0.5920(4) 0.3591(2) 0.0787(10) Uani 1 1 d . . . . .
F1 F 0.8607(4) 0.2439(4) 0.2018(2) 0.1137(13) Uani 1 1 d . . . . .
O1 O 0.3314(5) 0.7208(4) 0.4604(2) 0.0916(12) Uani 1 1 d . . . . .
N1 N 0.2489(5) 0.6899(5) 0.3887(2) 0.0659(11) Uani 1 1 d . . . . .
C18 C 0.4820(4) 0.6454(4) 0.1529(3) 0.0456(9) Uani 1 1 d . . . . .
C11 C 0.4266(4) 0.4797(4) 0.2347(2) 0.0430(9) Uani 1 1 d . . . . .
C8 C 0.3629(4) 0.5237(4) 0.1630(2) 0.0410(8) Uani 1 1 d . . . . .
C25 C 0.2427(4) 0.2550(4) 0.0687(2) 0.0453(9) Uani 1 1 d . . . . .
C12 C 0.5393(4) 0.4127(4) 0.2209(3) 0.0447(9) Uani 1 1 d . . . . .
C9 C 0.2935(4) 0.4038(3) 0.0689(2) 0.0409(8) Uani 1 1 d . . . . .
H9 H 0.362682 0.411401 0.030117 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2311(4) 0.5716(4) 0.1886(2) 0.0432(9) Uani 1 1 d . . . . .
H7 H 0.179903 0.515360 0.220501 0.052 Uiso 1 1 calc R U . . .
C10 C 0.1648(4) 0.4387(4) 0.0342(3) 0.0480(9) Uani 1 1 d . . . . .
C6 C 0.2712(4) 0.7263(4) 0.2446(3) 0.0500(10) Uani 1 1 d . . . . .
C13 C 0.6114(5) 0.4097(4) 0.1524(3) 0.0537(10) Uani 1 1 d . . . . .
H13 H 0.586176 0.446657 0.110155 0.064 Uiso 1 1 calc R U . . .
C30 C 0.1389(5) 0.2129(4) 0.1138(3) 0.0569(11) Uani 1 1 d . . . . .
H30 H 0.098193 0.276436 0.145405 0.068 Uiso 1 1 calc R U . . .
C26 C 0.3025(5) 0.1608(4) 0.0220(3) 0.0563(11) Uani 1 1 d . . . . .
H26 H 0.372113 0.187988 -0.009323 0.068 Uiso 1 1 calc R U . . .
C1 C 0.2894(5) 0.7799(4) 0.3368(3) 0.0557(11) Uani 1 1 d . . . . .
C17 C 0.5779(5) 0.3597(5) 0.2838(3) 0.0581(11) Uani 1 1 d . . . . .
H17 H 0.530905 0.363044 0.330945 0.070 Uiso 1 1 calc R U . . .
C5 C 0.3008(5) 0.8240(4) 0.2033(3) 0.0573(11) Uani 1 1 d . . . . .
H5 H 0.288079 0.792248 0.140956 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3484(5) 0.9667(5) 0.2522(3) 0.0703(14) Uani 1 1 d . . . . .
H4 H 0.366133 1.029896 0.222726 0.084 Uiso 1 1 calc R U . . .
C2 C 0.3407(5) 0.9223(5) 0.3863(3) 0.0693(14) Uani 1 1 d . . . . .
H2A H 0.355752 0.955206 0.448757 0.083 Uiso 1 1 calc R U . . .
C19 C 0.6978(5) 0.8603(5) 0.2340(3) 0.0727(14) Uani 1 1 d . . . . .
H19 H 0.662373 0.898899 0.191711 0.087 Uiso 1 1 calc R U . . .
C14 C 0.7206(5) 0.3527(5) 0.1455(3) 0.0645(12) Uani 1 1 d . . . . .
H14 H 0.769255 0.350192 0.099203 0.077 Uiso 1 1 calc R U . . .
C29 C 0.0942(5) 0.0766(5) 0.1128(3) 0.0694(13) Uani 1 1 d . . . . .
H29 H 0.024242 0.048859 0.143660 0.083 Uiso 1 1 calc R U . . .
C27 C 0.2584(6) 0.0246(5) 0.0218(3) 0.0721(14) Uani 1 1 d . . . . .
H27 H 0.300277 -0.038723 -0.008542 0.086 Uiso 1 1 calc R U . . .
C3 C 0.3695(6) 1.0151(5) 0.3433(4) 0.0767(15) Uani 1 1 d . . . . .
H3A H 0.403588 1.111595 0.376425 0.092 Uiso 1 1 calc R U . . .
C28 C 0.1536(6) -0.0168(5) 0.0661(4) 0.0757(16) Uani 1 1 d . . . . .
H28 H 0.122797 -0.108741 0.064402 0.091 Uiso 1 1 calc R U . . .
C16 C 0.6859(6) 0.3014(6) 0.2772(4) 0.0773(15) Uani 1 1 d . . . . .
H16 H 0.711566 0.263543 0.318774 0.093 Uiso 1 1 calc R U . . .
C15 C 0.7545(6) 0.3007(6) 0.2082(4) 0.0750(15) Uani 1 1 d . . . . .
C20 C 0.7404(5) 0.9718(5) 0.3304(4) 0.091(2) Uani 1 1 d . . . . .
H20A H 0.801835 1.061628 0.331121 0.110 Uiso 1 1 calc R U . . .
H20B H 0.652971 0.983170 0.348792 0.110 Uiso 1 1 calc R U . . .
C31 C -0.2172(6) 0.6272(5) 0.5529(3) 0.0735(14) Uani 1 1 d . . . . .
H31 H -0.252373 0.535006 0.558277 0.088 Uiso 1 1 calc R U . . .
C23 C 0.8922(6) 0.7801(6) 0.2709(5) 0.100(2) Uani 1 1 d . . . . .
H23A H 0.978053 0.765367 0.251826 0.120 Uiso 1 1 calc R U . . .
H23B H 0.827608 0.690694 0.269046 0.120 Uiso 1 1 calc R U . . .
C24 C 0.8203(7) 0.8233(7) 0.2097(4) 0.0941(19) Uani 1 1 d . . . . .
H24A H 0.787072 0.747742 0.150882 0.113 Uiso 1 1 calc R U . . .
H24B H 0.890347 0.903928 0.204294 0.113 Uiso 1 1 calc R U . . .
C22 C 0.9376(7) 0.8840(8) 0.3656(4) 0.103(2) Uani 1 1 d . . . . .
H22A H 0.972216 0.842078 0.405263 0.124 Uiso 1 1 calc R U . . .
H22B H 1.018196 0.965894 0.370289 0.124 Uiso 1 1 calc R U . . .
C21 C 0.8207(8) 0.9287(7) 0.3956(4) 0.104(2) Uani 1 1 d . . . . .
H21A H 0.861022 1.007537 0.452856 0.125 Uiso 1 1 calc R U . . .
H21B H 0.751668 0.852239 0.405563 0.125 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C7 N2 H2 122.5 . . ?
C10 N2 H2 122.5 . . ?
C10 N2 C7 115.0(3) . . ?
C18 N3 H3 118.0 . . ?
C18 N3 C19 123.9(4) . . ?
C19 N3 H3 118.0 . . ?
O2 N1 O1 123.9(5) . . ?
O2 N1 C1 118.4(4) . . ?
O1 N1 C1 117.6(5) . . ?
O5 C18 N3 123.8(4) . . ?
O5 C18 C8 120.8(3) . . ?
N3 C18 C8 115.4(3) . . ?
O4 C11 C8 119.5(3) . . ?
O4 C11 C12 119.6(3) . . ?
C12 C11 C8 120.8(3) . . ?
C18 C8 C9 108.7(3) . . ?
C18 C8 C7 110.0(3) . . ?
C11 C8 C18 109.8(3) . . ?
C11 C8 C9 114.7(3) . . ?
C11 C8 C7 110.3(3) . . ?
C9 C8 C7 103.2(3) . . ?
C30 C25 C9 121.6(4) . . ?
C30 C25 C26 119.6(4) . . ?
C26 C25 C9 118.9(4) . . ?
C13 C12 C11 123.2(3) . . ?
C17 C12 C11 117.1(4) . . ?
C17 C12 C13 119.5(4) . . ?
C8 C9 H9 109.3 . . ?
C25 C9 C8 115.7(3) . . ?
C25 C9 H9 109.3 . . ?
C10 C9 C8 102.6(3) . . ?
C10 C9 C25 110.5(3) . . ?
C10 C9 H9 109.3 . . ?
N2 C7 C8 102.0(3) . . ?
N2 C7 H7 109.1 . . ?
N2 C7 C6 111.8(3) . . ?
C8 C7 H7 109.1 . . ?
C6 C7 C8 115.4(3) . . ?
C6 C7 H7 109.1 . . ?
O3 C10 N2 125.5(4) . . ?
O3 C10 C9 124.6(4) . . ?
N2 C10 C9 109.9(3) . . ?
C1 C6 C7 124.2(4) . . ?
C1 C6 C5 116.3(4) . . ?
C5 C6 C7 119.4(4) . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C25 C30 H30 119.7 . . ?
C25 C30 C29 120.6(4) . . ?
C29 C30 H30 119.7 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(5) . . ?
C27 C26 H26 120.2 . . ?
C6 C1 N1 122.6(4) . . ?
C2 C1 N1 115.1(4) . . ?
C2 C1 C6 122.2(4) . . ?
C12 C17 H17 119.9 . . ?
C12 C17 C16 120.1(4) . . ?
C16 C17 H17 119.9 . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.1 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2A 120.2 . . ?
N3 C19 H19 108.8 . . ?
N3 C19 C20 109.3(4) . . ?
C20 C19 H19 108.8 . . ?
C24 C19 N3 109.7(5) . . ?
C24 C19 H19 108.8 . . ?
C24 C19 C20 111.3(4) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 C13 117.9(5) . . ?
C15 C14 H14 121.1 . . ?
C30 C29 H29 120.2 . . ?
C28 C29 C30 119.7(5) . . ?
C28 C29 H29 120.2 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(5) . . ?
C28 C27 H27 119.8 . . ?
C4 C3 C2 120.0(5) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C29 C28 C27 120.2(5) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C17 C16 H16 120.8 . . ?
C15 C16 C17 118.3(4) . . ?
C15 C16 H16 120.8 . . ?
F1 C15 C16 118.4(5) . . ?
C14 C15 F1 118.3(5) . . ?
C14 C15 C16 123.3(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C21 C20 C19 110.8(4) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
Cl2 C31 H31 108.3 . . ?
Cl1 C31 Cl2 109.3(3) . . ?
Cl1 C31 H31 108.3 . . ?
Cl3 C31 Cl2 111.1(3) . . ?
Cl3 C31 Cl1 111.3(3) . . ?
Cl3 C31 H31 108.3 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C24 C23 C22 113.2(5) . . ?
C22 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C19 C24 H24A 108.6 . . ?
C19 C24 H24B 108.6 . . ?
C23 C24 C19 114.8(5) . . ?
C23 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
H24A C24 H24B 107.5 . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C21 C22 C23 113.0(5) . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22 C21 C20 113.8(5) . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
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
Cl2 C31 1.759(6) . ?
Cl1 C31 1.758(6) . ?
Cl3 C31 1.744(6) . ?
O5 C18 1.226(5) . ?
O4 C11 1.226(5) . ?
O3 C10 1.233(5) . ?
N2 H2 0.8700 . ?
N2 C7 1.452(5) . ?
N2 C10 1.341(5) . ?
N3 H3 0.8700 . ?
N3 C18 1.342(5) . ?
N3 C19 1.480(6) . ?
O2 N1 1.226(6) . ?
F1 C15 1.365(5) . ?
O1 N1 1.229(5) . ?
N1 C1 1.480(6) . ?
C18 C8 1.558(6) . ?
C11 C8 1.529(5) . ?
C11 C12 1.502(5) . ?
C8 C9 1.569(5) . ?
C8 C7 1.595(5) . ?
C25 C9 1.536(5) . ?
C25 C30 1.390(6) . ?
C25 C26 1.390(6) . ?
C12 C13 1.392(6) . ?
C12 C17 1.388(6) . ?
C9 H9 0.9900 . ?
C9 C10 1.529(5) . ?
C7 H7 0.9900 . ?
C7 C6 1.528(5) . ?
C6 C1 1.392(6) . ?
C6 C5 1.402(6) . ?
C13 H13 0.9400 . ?
C13 C14 1.394(6) . ?
C30 H30 0.9400 . ?
C30 C29 1.401(6) . ?
C26 H26 0.9400 . ?
C26 C27 1.405(7) . ?
C1 C2 1.389(6) . ?
C17 H17 0.9400 . ?
C17 C16 1.392(6) . ?
C5 H5 0.9400 . ?
C5 C4 1.391(6) . ?
C4 H4 0.9400 . ?
C4 C3 1.372(7) . ?
C2 H2A 0.9400 . ?
C2 C3 1.378(8) . ?
C19 H19 0.9900 . ?
C19 C20 1.557(8) . ?
C19 C24 1.448(8) . ?
C14 H14 0.9400 . ?
C14 C15 1.363(7) . ?
C29 H29 0.9400 . ?
C29 C28 1.381(8) . ?
C27 H27 0.9400 . ?
C27 C28 1.384(8) . ?
C3 H3A 0.9400 . ?
C28 H28 0.9400 . ?
C16 H16 0.9400 . ?
C16 C15 1.379(8) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 C21 1.518(9) . ?
C31 H31 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 C24 1.428(9) . ?
C23 C22 1.508(9) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 C21 1.460(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 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
O5 C18 C8 C11 148.3(3) . . . . ?
O5 C18 C8 C9 22.1(5) . . . . ?
O5 C18 C8 C7 -90.2(4) . . . . ?
O4 C11 C8 C18 109.9(4) . . . . ?
O4 C11 C8 C9 -127.4(4) . . . . ?
O4 C11 C8 C7 -11.4(5) . . . . ?
O4 C11 C12 C13 -164.4(4) . . . . ?
O4 C11 C12 C17 11.5(5) . . . . ?
N2 C7 C6 C1 145.5(4) . . . . ?
N2 C7 C6 C5 -38.6(5) . . . . ?
N3 C18 C8 C11 -33.9(4) . . . . ?
N3 C18 C8 C9 -160.1(3) . . . . ?
N3 C18 C8 C7 87.6(4) . . . . ?
N3 C19 C20 C21 71.7(6) . . . . ?
N3 C19 C24 C23 -67.4(6) . . . . ?
O2 N1 C1 C6 -43.4(6) . . . . ?
O2 N1 C1 C2 133.7(4) . . . . ?
O1 N1 C1 C6 138.8(4) . . . . ?
O1 N1 C1 C2 -44.1(5) . . . . ?
N1 C1 C2 C3 -174.4(4) . . . . ?
C18 N3 C19 C20 152.6(4) . . . . ?
C18 N3 C19 C24 -85.1(5) . . . . ?
C18 C8 C9 C25 147.2(3) . . . . ?
C18 C8 C9 C10 -92.4(3) . . . . ?
C18 C8 C7 N2 90.0(3) . . . . ?
C18 C8 C7 C6 -31.5(4) . . . . ?
C11 C8 C9 C25 23.9(5) . . . . ?
C11 C8 C9 C10 144.3(3) . . . . ?
C11 C8 C7 N2 -148.8(3) . . . . ?
C11 C8 C7 C6 89.7(4) . . . . ?
C11 C12 C13 C14 176.6(4) . . . . ?
C11 C12 C17 C16 -177.3(4) . . . . ?
C8 C11 C12 C13 12.2(5) . . . . ?
C8 C11 C12 C17 -171.9(4) . . . . ?
C8 C9 C10 O3 165.6(4) . . . . ?
C8 C9 C10 N2 -14.5(4) . . . . ?
C8 C7 C6 C1 -98.5(5) . . . . ?
C8 C7 C6 C5 77.4(4) . . . . ?
C25 C9 C10 O3 -70.5(5) . . . . ?
C25 C9 C10 N2 109.4(4) . . . . ?
C25 C30 C29 C28 -0.3(6) . . . . ?
C25 C26 C27 C28 1.5(6) . . . . ?
C12 C11 C8 C18 -66.7(4) . . . . ?
C12 C11 C8 C9 56.1(5) . . . . ?
C12 C11 C8 C7 172.0(3) . . . . ?
C12 C13 C14 C15 -0.3(7) . . . . ?
C12 C17 C16 C15 1.3(7) . . . . ?
C9 C8 C7 N2 -25.9(4) . . . . ?
C9 C8 C7 C6 -147.3(3) . . . . ?
C9 C25 C30 C29 -180.0(4) . . . . ?
C9 C25 C26 C27 179.4(4) . . . . ?
C7 N2 C10 O3 176.9(4) . . . . ?
C7 N2 C10 C9 -3.0(5) . . . . ?
C7 C8 C9 C25 -96.1(4) . . . . ?
C7 C8 C9 C10 24.3(4) . . . . ?
C7 C6 C1 N1 -10.1(6) . . . . ?
C7 C6 C1 C2 173.0(4) . . . . ?
C7 C6 C5 C4 -175.0(4) . . . . ?
C10 N2 C7 C8 18.8(4) . . . . ?
C10 N2 C7 C6 142.7(4) . . . . ?
C6 C1 C2 C3 2.8(7) . . . . ?
C6 C5 C4 C3 0.9(7) . . . . ?
C13 C12 C17 C16 -1.3(6) . . . . ?
C13 C14 C15 F1 179.6(4) . . . . ?
C13 C14 C15 C16 0.3(8) . . . . ?
C30 C25 C9 C8 59.8(5) . . . . ?
C30 C25 C9 C10 -56.3(5) . . . . ?
C30 C25 C26 C27 -0.7(6) . . . . ?
C30 C29 C28 C27 1.1(7) . . . . ?
C26 C25 C9 C8 -120.3(4) . . . . ?
C26 C25 C9 C10 123.7(4) . . . . ?
C26 C25 C30 C29 0.1(6) . . . . ?
C26 C27 C28 C29 -1.7(7) . . . . ?
C1 C6 C5 C4 1.3(6) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C17 C12 C13 C14 0.7(6) . . . . ?
C17 C16 C15 F1 179.9(5) . . . . ?
C17 C16 C15 C14 -0.8(8) . . . . ?
C5 C6 C1 N1 173.8(4) . . . . ?
C5 C6 C1 C2 -3.1(6) . . . . ?
C5 C4 C3 C2 -1.3(8) . . . . ?
C19 N3 C18 O5 0.7(6) . . . . ?
C19 N3 C18 C8 -177.1(4) . . . . ?
C19 C20 C21 C22 48.4(7) . . . . ?
C20 C19 C24 C23 53.7(7) . . . . ?
C23 C22 C21 C20 -48.4(8) . . . . ?
C24 C19 C20 C21 -49.6(7) . . . . ?
C24 C23 C22 C21 50.0(8) . . . . ?
C22 C23 C24 C19 -53.6(7) . . . . ?
