#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:24:17 +0100 (Fri 05 de Mar de 2021) $
#$Revision: 262711 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/78/7157833.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_7157833
loop_
_publ_author_name
'Hsueh, Nai-Chen'
'Chen, Shin-Mei'
'Lin, Chun-Yi'
'Chang, Meng-Yang'
_publ_section_title
;
 HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids
 with arylaldehydes: one-pot synthesis of 1-arylisoquinolines.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1047
_journal_page_last               1059
_journal_paper_doi               10.1039/d0ob02431g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H18 N2 O6'
_chemical_formula_sum            'C19 H18 N2 O6'
_chemical_formula_weight         370.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2020-05-02 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.680(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5325(2)
_cell_length_b                   8.1523(2)
_cell_length_c                   19.8965(4)
_cell_measurement_reflns_used    7192
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.7850
_cell_measurement_theta_min      1.9380
_cell_volume                     1702.70(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_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(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     10.00  40.00   0.50   10.87    --   10.60  77.00 -90.00   60
  2  ω    -77.00  17.00   0.50   10.87    --   10.60 -38.00  60.00  188
  3  ω    -13.00  48.00   0.50   10.87    --   10.60 -38.00  90.00  122
  4  ω     60.00 100.00   0.50   10.87    --   10.60  77.00 -90.00   80
  5  ω    -86.00 -52.00   0.50   10.87    --  -10.90 -57.00 -30.00   68
  6  ω    -34.00   7.00   0.50   10.87    --  -10.90 -57.00 -30.00   82
  7  ω    -38.00  -5.00   0.50   10.87    --  -10.90  82.00  60.00   66
  8  ω    -24.00  10.00   0.50   10.87    --  -10.90  77.00 -30.00   68
  9  ω     42.00  67.00   0.50   10.87    --  -10.90  82.00  60.00   50
 10  ω    -17.00  78.00   0.50   10.87    --  -10.90  77.00   0.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0422832000
_diffrn_orient_matrix_UB_12      -0.0662012000
_diffrn_orient_matrix_UB_13      -0.0079700000
_diffrn_orient_matrix_UB_21      0.0215807000
_diffrn_orient_matrix_UB_22      -0.0392618000
_diffrn_orient_matrix_UB_23      0.0306354000
_diffrn_orient_matrix_UB_31      -0.0480777000
_diffrn_orient_matrix_UB_32      0.0405979000
_diffrn_orient_matrix_UB_33      0.0166485000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13633
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.014
_diffrn_reflns_theta_min         1.940
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0074(11)
_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   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3558
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0431P)²+0.5305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2987
_reflns_number_total             3558
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob02431g2.cif
_cod_data_source_block           sh0211-2
_cod_depositor_comments
'Adding full bibliography for 7157832--7157834.cif.'
_cod_database_code               7157833
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H19 N2 O6'
_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.
;
_diffrn_oxdiff_digest_frames
;
01093e50bc978df131db035efeec0c360400025243a
;
_diffrn_oxdiff_digest_hkl
;
01079d6a7905a75d102c6591f61e05c7e8a36f
;
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7), C15(H15), C16(H16), C18(H18)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.719
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.37067(8) 0.84399(11) 0.48449(5) 0.0218(2) Uani 1 1 d . . . . .
O2 O 0.97590(8) 0.54504(11) 0.62934(5) 0.0207(2) Uani 1 1 d . . . . .
O3 O 0.86645(8) 0.33620(11) 0.69803(5) 0.0222(2) Uani 1 1 d . . . . .
O4 O 0.47130(8) 0.51300(12) 0.75161(4) 0.0189(2) Uani 1 1 d . . . . .
O5 O 0.06475(9) 0.17911(13) 0.55139(5) 0.0297(3) Uani 1 1 d . . . . .
O6 O 0.02257(9) 0.05715(12) 0.64339(5) 0.0269(2) Uani 1 1 d . . . . .
N1 N 0.37577(9) 0.64012(13) 0.56657(5) 0.0160(2) Uani 1 1 d . . . . .
N2 N 0.08436(10) 0.15475(13) 0.61232(6) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.43811(11) 0.74250(16) 0.52817(6) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.56872(11) 0.75466(15) 0.53063(6) 0.0164(3) Uani 1 1 d . . . . .
H2 H 0.607409 0.831347 0.504354 0.020 Uiso 1 1 calc R . . . .
C3 C 0.64179(11) 0.64943(15) 0.57338(6) 0.0153(3) Uani 1 1 d . . . . .
C4 C 0.77771(11) 0.65504(16) 0.57831(6) 0.0161(3) Uani 1 1 d . . . . .
H4 H 0.819209 0.730702 0.552821 0.019 Uiso 1 1 calc R . . . .
C5 C 0.84675(11) 0.55054(16) 0.62000(6) 0.0166(3) Uani 1 1 d . . . . .
C6 C 0.78408(11) 0.43124(16) 0.65907(6) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.65453(11) 0.42333(16) 0.65521(6) 0.0166(3) Uani 1 1 d . . . . .
H7 H 0.614798 0.344636 0.680052 0.020 Uiso 1 1 calc R . . . .
C8 C 0.57908(11) 0.53464(15) 0.61340(6) 0.0150(3) Uani 1 1 d . . . . .
C9 C 0.44431(11) 0.53996(15) 0.60887(6) 0.0147(3) Uani 1 1 d . . . . .
C10 C 0.23442(11) 0.83695(18) 0.48218(7) 0.0232(3) Uani 1 1 d . . . . .
H10A H 0.198504 0.906396 0.446581 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.206825 0.873667 0.524458 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.206671 0.726062 0.473950 0.035 Uiso 1 1 calc GR . . . .
C11 C 1.04308(12) 0.65472(18) 0.58870(7) 0.0237(3) Uani 1 1 d . . . . .
H11A H 1.022207 0.630210 0.541906 0.036 Uiso 1 1 calc GR . . . .
H11B H 1.133101 0.641884 0.599251 0.036 Uiso 1 1 calc GR . . . .
H11C H 1.018991 0.765668 0.597667 0.036 Uiso 1 1 calc GR . . . .
C12 C 0.81247(13) 0.2088(2) 0.73553(8) 0.0321(4) Uani 1 1 d . . . . .
H12A H 0.762724 0.137614 0.705292 0.048 Uiso 1 1 calc GR . . . .
H12B H 0.758881 0.255922 0.767208 0.048 Uiso 1 1 calc GR . . . .
H12C H 0.879408 0.146939 0.759359 0.048 Uiso 1 1 calc GR . . . .
C13 C 0.36489(11) 0.43039(15) 0.64873(6) 0.0150(3) Uani 1 1 d . . . . .
C14 C 0.38046(11) 0.41633(15) 0.71945(6) 0.0156(3) Uani 1 1 d . . . . .
C15 C 0.30124(12) 0.31346(16) 0.75353(7) 0.0180(3) Uani 1 1 d . . . . .
H15 H 0.314089 0.302604 0.800114 0.022 Uiso 1 1 calc R . . . .
C16 C 0.20398(12) 0.22779(16) 0.71849(7) 0.0185(3) Uani 1 1 d . . . . .
H16 H 0.150694 0.159780 0.741044 0.022 Uiso 1 1 calc R . . . .
C17 C 0.18745(11) 0.24509(15) 0.64940(6) 0.0166(3) Uani 1 1 d . . . . .
C18 C 0.26558(11) 0.34490(15) 0.61451(6) 0.0157(3) Uani 1 1 d . . . . .
H18 H 0.251509 0.354752 0.567930 0.019 Uiso 1 1 calc R . . . .
C19 C 0.50553(13) 0.48210(18) 0.82177(6) 0.0240(3) Uani 1 1 d . . . . .
H19A H 0.526288 0.368172 0.828068 0.036 Uiso 1 1 calc GR . . . .
H19B H 0.435215 0.509548 0.847454 0.036 Uiso 1 1 calc GR . . . .
H19C H 0.577998 0.547897 0.836703 0.036 Uiso 1 1 calc GR . . . .
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
C1 O1 C10 117.80(10) . . ?
C5 O2 C11 115.97(10) . . ?
C6 O3 C12 116.83(10) . . ?
C14 O4 C19 117.88(10) . . ?
C1 N1 C9 118.28(10) . . ?
O5 N2 C17 118.34(10) . . ?
O6 N2 O5 123.27(11) . . ?
O6 N2 C17 118.39(11) . . ?
O1 C1 C2 116.62(11) . . ?
N1 C1 O1 119.32(11) . . ?
N1 C1 C2 124.05(11) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.53(11) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 121.50(11) . . ?
C2 C3 C8 119.13(11) . . ?
C8 C3 C4 119.37(11) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.38(12) . . ?
C5 C4 H4 119.8 . . ?
O2 C5 C6 113.72(11) . . ?
C4 C5 O2 125.77(11) . . ?
C4 C5 C6 120.52(11) . . ?
O3 C6 C5 113.22(10) . . ?
O3 C6 C7 126.56(12) . . ?
C7 C6 C5 120.21(11) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.68(12) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 118.78(11) . . ?
C9 C8 C3 116.88(11) . . ?
C9 C8 C7 124.34(11) . . ?
N1 C9 C8 123.00(11) . . ?
N1 C9 C13 113.64(10) . . ?
C8 C9 C13 123.33(11) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C9 123.66(11) . . ?
C18 C13 C9 118.14(11) . . ?
C18 C13 C14 118.10(11) . . ?
O4 C14 C13 116.33(11) . . ?
O4 C14 C15 123.04(11) . . ?
C15 C14 C13 120.56(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.43(12) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.67(12) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 N2 118.69(11) . . ?
C16 C17 C18 121.90(11) . . ?
C18 C17 N2 119.40(11) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.29(11) . . ?
C17 C18 H18 119.9 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 C1 1.3579(15) . ?
O1 C10 1.4331(14) . ?
O2 C5 1.3586(14) . ?
O2 C11 1.4309(15) . ?
O3 C6 1.3579(15) . ?
O3 C12 1.4241(16) . ?
O4 C14 1.3587(15) . ?
O4 C19 1.4351(15) . ?
O5 N2 1.2292(14) . ?
O6 N2 1.2265(14) . ?
N1 C1 1.3392(16) . ?
N1 C9 1.3405(16) . ?
N2 C17 1.4611(16) . ?
C1 C2 1.3761(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.3946(18) . ?
C3 C4 1.4276(16) . ?
C3 C8 1.4254(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.3580(18) . ?
C5 C6 1.4385(18) . ?
C6 C7 1.3619(17) . ?
C7 H7 0.9300 . ?
C7 C8 1.4279(17) . ?
C8 C9 1.4156(16) . ?
C9 C13 1.4950(17) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.4080(17) . ?
C13 C18 1.3882(17) . ?
C14 C15 1.3969(17) . ?
C15 H15 0.9300 . ?
C15 C16 1.3808(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.3786(18) . ?
C17 C18 1.3837(17) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O1 C1 C2 C3 -178.18(11) . . . . ?
O2 C5 C6 O3 0.19(15) . . . . ?
O2 C5 C6 C7 179.49(11) . . . . ?
O3 C6 C7 C8 178.11(12) . . . . ?
O4 C14 C15 C16 174.86(12) . . . . ?
O5 N2 C17 C16 175.20(11) . . . . ?
O5 N2 C17 C18 -4.91(17) . . . . ?
O6 N2 C17 C16 -5.55(17) . . . . ?
O6 N2 C17 C18 174.34(11) . . . . ?
N1 C1 C2 C3 2.97(19) . . . . ?
N1 C9 C13 C14 -127.82(12) . . . . ?
N1 C9 C13 C18 48.35(15) . . . . ?
N2 C17 C18 C13 -179.32(11) . . . . ?
C1 N1 C9 C8 -1.72(18) . . . . ?
C1 N1 C9 C13 -179.54(10) . . . . ?
C1 C2 C3 C4 179.85(12) . . . . ?
C1 C2 C3 C8 -0.64(18) . . . . ?
C2 C3 C4 C5 -179.58(12) . . . . ?
C2 C3 C8 C7 177.76(11) . . . . ?
C2 C3 C8 C9 -2.49(17) . . . . ?
C3 C4 C5 O2 -179.46(11) . . . . ?
C3 C4 C5 C6 0.87(19) . . . . ?
C3 C8 C9 N1 3.80(18) . . . . ?
C3 C8 C9 C13 -178.60(11) . . . . ?
C4 C3 C8 C7 -2.72(17) . . . . ?
C4 C3 C8 C9 177.03(11) . . . . ?
C4 C5 C6 O3 179.90(11) . . . . ?
C4 C5 C6 C7 -0.81(19) . . . . ?
C5 C6 C7 C8 -1.07(19) . . . . ?
C6 C7 C8 C3 2.82(18) . . . . ?
C6 C7 C8 C9 -176.92(12) . . . . ?
C7 C8 C9 N1 -176.46(12) . . . . ?
C7 C8 C9 C13 1.14(19) . . . . ?
C8 C3 C4 C5 0.91(18) . . . . ?
C8 C9 C13 C14 54.38(17) . . . . ?
C8 C9 C13 C18 -129.45(13) . . . . ?
C9 N1 C1 O1 179.38(11) . . . . ?
C9 N1 C1 C2 -1.81(19) . . . . ?
C9 C13 C14 O4 1.86(17) . . . . ?
C9 C13 C14 C15 178.89(11) . . . . ?
C9 C13 C18 C17 -178.41(11) . . . . ?
C10 O1 C1 N1 0.50(17) . . . . ?
C10 O1 C1 C2 -178.40(11) . . . . ?
C11 O2 C5 C4 -3.21(18) . . . . ?
C11 O2 C5 C6 176.48(11) . . . . ?
C12 O3 C6 C5 -176.63(12) . . . . ?
C12 O3 C6 C7 4.13(19) . . . . ?
C13 C14 C15 C16 -1.96(19) . . . . ?
C14 C13 C18 C17 -2.02(18) . . . . ?
C14 C15 C16 C17 0.44(19) . . . . ?
C15 C16 C17 N2 -179.86(11) . . . . ?
C15 C16 C17 C18 0.25(19) . . . . ?
C16 C17 C18 C13 0.57(19) . . . . ?
C18 C13 C14 O4 -174.31(11) . . . . ?
C18 C13 C14 C15 2.71(17) . . . . ?
C19 O4 C14 C13 -169.29(11) . . . . ?
C19 O4 C14 C15 13.77(17) . . . . ?
