#------------------------------------------------------------------------------
#$Date: 2020-04-08 02:31:42 +0300 (Wed, 08 Apr 2020) $
#$Revision: 250461 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038221.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_4038221
loop_
_publ_author_name
'Liu, Renzhi'
'Yang, Min'
'Xie, Wenlin'
'Dong, Wenbi'
'Zhou, Hongwei'
'Yadav, Sarita'
'Potkin, Vladimir Ivanovich'
'Qiu, Guanyinsheng'
_publ_section_title
;
 Synthesis of 3-Hydroxyisoindolin-1-ones Through 1, 4-Dioxane-Mediated
 Hydroxylhydrative aza-Cyclization of 2-Alkynylbenzamide in Water.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03466
_journal_year                    2020
_chemical_formula_moiety         'C20 H15 N O4'
_chemical_formula_sum            'C20 H15 N O4'
_chemical_formula_weight         333.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.518(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5395(16)
_cell_length_b                   7.0403(7)
_cell_length_c                   16.2326(18)
_cell_measurement_reflns_used    1909
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      26.0910
_cell_measurement_theta_min      3.8380
_cell_volume                     1640.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -64.00 -33.00   1.00    1.48    --  -16.05 131.00-101.00   31
  2  ω    -25.00   1.00   1.00    1.48    --  -16.05 -57.00 -30.00   26
  3  ω     11.00  73.00   1.00    1.48    --   16.20  57.00-120.00   62
  4  ω    -50.00  51.00   1.00    1.48    --   16.20   0.00  90.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0252228000
_diffrn_orient_matrix_UB_12      0.0649290000
_diffrn_orient_matrix_UB_13      -0.0342140000
_diffrn_orient_matrix_UB_21      0.0008011000
_diffrn_orient_matrix_UB_22      -0.0662064000
_diffrn_orient_matrix_UB_23      -0.0325883000
_diffrn_orient_matrix_UB_31      -0.0424694000
_diffrn_orient_matrix_UB_32      -0.0396416000
_diffrn_orient_matrix_UB_33      -0.0013623000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7449
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.388
_diffrn_reflns_theta_min         2.838
_diffrn_source                   'fine-focus sealed X-ray tube'
_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  0.81384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0091(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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0507
_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)+(0.0477P)²+0.3993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2293
_reflns_number_total             3824
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03466_si_002.cif
_cod_data_source_block           20190625-1
_cod_database_code               4038221
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O'
_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   0.991
_shelx_estimated_absorpt_t_min   0.989
_reflns_odcompleteness_completeness 99.75
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18),
  C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.773
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.84363(10) 0.8157(2) 0.65099(9) 0.0558(4) Uani 1 1 d . . . . .
O2 O 0.76886(9) 0.4761(2) 0.68286(9) 0.0536(4) Uani 1 1 d . . . . .
O3 O 0.86669(9) 0.1929(2) 0.59691(10) 0.0537(4) Uani 1 1 d . . . . .
H3 H 0.834721 0.103413 0.600855 0.081 Uiso 1 1 calc GR . . . .
O4 O 0.69017(10) 0.1214(2) 0.52498(12) 0.0741(5) Uani 1 1 d . . . . .
N1 N 0.82194(11) 0.4931(2) 0.63107(10) 0.0430(4) Uani 1 1 d . . . . .
C1 C 0.84451(12) 0.6705(3) 0.61112(12) 0.0410(4) Uani 1 1 d . . . . .
C2 C 0.86709(12) 0.6420(3) 0.53175(12) 0.0408(4) Uani 1 1 d . . . . .
C3 C 0.90700(13) 0.7725(3) 0.49187(15) 0.0530(5) Uani 1 1 d . . . . .
H3A H 0.923613 0.893805 0.515261 0.064 Uiso 1 1 calc R . . . .
C4 C 0.92063(14) 0.7162(4) 0.41810(16) 0.0595(6) Uani 1 1 d . . . . .
H4 H 0.948525 0.799571 0.391354 0.071 Uiso 1 1 calc R . . . .
C5 C 0.89343(14) 0.5334(3) 0.38055(14) 0.0540(6) Uani 1 1 d . . . . .
C6 C 0.90413(18) 0.4768(4) 0.30180(17) 0.0770(8) Uani 1 1 d . . . . .
H6 H 0.931683 0.559584 0.274499 0.092 Uiso 1 1 calc R . . . .
C7 C 0.8749(2) 0.3032(5) 0.26494(18) 0.0873(9) Uani 1 1 d . . . . .
H7 H 0.881977 0.269711 0.212482 0.105 Uiso 1 1 calc R . . . .
C8 C 0.83414(18) 0.1740(4) 0.30506(16) 0.0771(8) Uani 1 1 d . . . . .
H8 H 0.813864 0.056333 0.278782 0.092 Uiso 1 1 calc R . . . .
C9 C 0.82422(15) 0.2204(3) 0.38220(14) 0.0581(6) Uani 1 1 d . . . . .
H9 H 0.798442 0.133086 0.409193 0.070 Uiso 1 1 calc R . . . .
C10 C 0.85280(12) 0.4003(3) 0.42166(13) 0.0453(5) Uani 1 1 d . . . . .
C11 C 0.84291(11) 0.4626(3) 0.49990(12) 0.0392(4) Uani 1 1 d . . . . .
C12 C 0.80981(12) 0.3505(3) 0.56218(12) 0.0419(4) Uani 1 1 d . . . . .
C13 C 0.82218(19) 0.4029(4) 0.76889(15) 0.0829(8) Uani 1 1 d . . . . .
H13A H 0.829421 0.268156 0.765029 0.124 Uiso 1 1 calc GR . . . .
H13B H 0.790784 0.428756 0.808377 0.124 Uiso 1 1 calc GR . . . .
H13C H 0.882397 0.462207 0.791436 0.124 Uiso 1 1 calc GR . . . .
C14 C 0.70677(13) 0.2878(3) 0.51924(13) 0.0466(5) Uani 1 1 d . . . . .
C15 C 0.63303(12) 0.4226(3) 0.46695(13) 0.0465(5) Uani 1 1 d . . . . .
C16 C 0.62024(14) 0.6012(4) 0.49509(15) 0.0596(6) Uani 1 1 d . . . . .
H16 H 0.661546 0.647241 0.549600 0.072 Uiso 1 1 calc R . . . .
C17 C 0.54627(16) 0.7121(4) 0.44257(18) 0.0745(7) Uani 1 1 d . . . . .
H17 H 0.536677 0.830874 0.462653 0.089 Uiso 1 1 calc R . . . .
C18 C 0.48743(17) 0.6480(5) 0.36155(19) 0.0808(8) Uani 1 1 d . . . . .
H18 H 0.437727 0.723125 0.326371 0.097 Uiso 1 1 calc R . . . .
C19 C 0.50089(18) 0.4747(5) 0.33178(17) 0.0856(9) Uani 1 1 d . . . . .
H19 H 0.461825 0.433779 0.275346 0.103 Uiso 1 1 calc R . . . .
C20 C 0.57191(16) 0.3598(4) 0.38462(15) 0.0677(7) Uani 1 1 d . . . . .
H20 H 0.578959 0.238917 0.364933 0.081 Uiso 1 1 calc R . . . .
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
N1 O2 C13 111.60(16) . . ?
C12 O3 H3 109.5 . . ?
O2 N1 C12 118.13(14) . . ?
C1 N1 O2 119.12(15) . . ?
C1 N1 C12 114.56(15) . . ?
O1 C1 N1 125.90(18) . . ?
O1 C1 C2 129.53(18) . . ?
N1 C1 C2 104.56(16) . . ?
C3 C2 C1 127.74(19) . . ?
C11 C2 C1 109.56(16) . . ?
C11 C2 C3 122.70(19) . . ?
C2 C3 H3A 121.1 . . ?
C4 C3 C2 117.7(2) . . ?
C4 C3 H3A 121.1 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.6(2) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C10 120.42(19) . . ?
C6 C5 C4 121.9(2) . . ?
C6 C5 C10 117.7(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 119.63(19) . . ?
C11 C10 C5 115.95(19) . . ?
C11 C10 C9 124.41(19) . . ?
C2 C11 C10 121.49(17) . . ?
C2 C11 C12 110.10(16) . . ?
C10 C11 C12 128.37(18) . . ?
O3 C12 N1 111.17(15) . . ?
O3 C12 C11 111.00(14) . . ?
O3 C12 C14 109.98(16) . . ?
N1 C12 C11 100.07(15) . . ?
N1 C12 C14 110.44(15) . . ?
C11 C12 C14 113.86(15) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 C12 117.13(19) . . ?
O4 C14 C15 121.59(18) . . ?
C15 C14 C12 121.08(17) . . ?
C16 C15 C14 125.01(19) . . ?
C16 C15 C20 118.7(2) . . ?
C20 C15 C14 116.3(2) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
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 1.213(2) . ?
O2 N1 1.3901(19) . ?
O2 C13 1.420(3) . ?
O3 H3 0.8200 . ?
O3 C12 1.396(2) . ?
O4 C14 1.211(2) . ?
N1 C1 1.369(2) . ?
N1 C12 1.460(2) . ?
C1 C2 1.473(3) . ?
C2 C3 1.398(3) . ?
C2 C11 1.362(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.353(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.418(3) . ?
C5 C6 1.408(3) . ?
C5 C10 1.430(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.360(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.403(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.359(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.412(3) . ?
C10 C11 1.406(3) . ?
C11 C12 1.519(3) . ?
C12 C14 1.546(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.480(3) . ?
C15 C16 1.378(3) . ?
C15 C20 1.383(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.360(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.357(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(4) . ?
C20 H20 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
_geom_hbond_publ_flag
O3 H3 O1 0.82 2.17 2.862(2) 142.6 1_545 yes
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 11.0(3) . . . . ?
O1 C1 C2 C11 -168.98(19) . . . . ?
O2 N1 C1 O1 19.7(3) . . . . ?
O2 N1 C1 C2 -159.16(14) . . . . ?
O2 N1 C12 O3 -86.36(18) . . . . ?
O2 N1 C12 C11 156.31(14) . . . . ?
O2 N1 C12 C14 36.0(2) . . . . ?
O3 C12 C14 O4 3.1(3) . . . . ?
O3 C12 C14 C15 -171.83(17) . . . . ?
O4 C14 C15 C16 135.2(2) . . . . ?
O4 C14 C15 C20 -43.3(3) . . . . ?
N1 C1 C2 C3 -170.19(18) . . . . ?
N1 C1 C2 C11 9.85(19) . . . . ?
N1 C12 C14 O4 -119.9(2) . . . . ?
N1 C12 C14 C15 65.1(2) . . . . ?
C1 N1 C12 O3 125.32(16) . . . . ?
C1 N1 C12 C11 7.99(19) . . . . ?
C1 N1 C12 C14 -112.32(18) . . . . ?
C1 C2 C3 C4 -179.19(18) . . . . ?
C1 C2 C11 C10 176.91(15) . . . . ?
C1 C2 C11 C12 -5.2(2) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C2 C11 C12 O3 -118.67(17) . . . . ?
C2 C11 C12 N1 -1.21(18) . . . . ?
C2 C11 C12 C14 116.59(18) . . . . ?
C3 C2 C11 C10 -3.1(3) . . . . ?
C3 C2 C11 C12 174.82(16) . . . . ?
C3 C4 C5 C6 177.5(2) . . . . ?
C3 C4 C5 C10 -1.8(3) . . . . ?
C4 C5 C6 C7 -177.8(2) . . . . ?
C4 C5 C10 C9 178.58(18) . . . . ?
C4 C5 C10 C11 -0.4(3) . . . . ?
C5 C6 C7 C8 -0.8(4) . . . . ?
C5 C10 C11 C2 2.7(2) . . . . ?
C5 C10 C11 C12 -174.71(17) . . . . ?
C6 C5 C10 C9 -0.7(3) . . . . ?
C6 C5 C10 C11 -179.69(18) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C10 1.4(3) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C8 C9 C10 C11 178.16(19) . . . . ?
C9 C10 C11 C2 -176.20(18) . . . . ?
C9 C10 C11 C12 6.3(3) . . . . ?
C10 C5 C6 C7 1.5(3) . . . . ?
C10 C11 C12 O3 59.0(2) . . . . ?
C10 C11 C12 N1 176.47(17) . . . . ?
C10 C11 C12 C14 -65.7(2) . . . . ?
C11 C2 C3 C4 0.8(3) . . . . ?
C11 C12 C14 O4 128.4(2) . . . . ?
C11 C12 C14 C15 -46.5(2) . . . . ?
C12 N1 C1 O1 167.72(18) . . . . ?
C12 N1 C1 C2 -11.2(2) . . . . ?
C12 C14 C15 C16 -50.1(3) . . . . ?
C12 C14 C15 C20 131.4(2) . . . . ?
C13 O2 N1 C1 -110.1(2) . . . . ?
C13 O2 N1 C12 103.1(2) . . . . ?
C14 C15 C16 C17 -176.9(2) . . . . ?
C14 C15 C20 C19 179.5(2) . . . . ?
C15 C16 C17 C18 -2.1(4) . . . . ?
C16 C15 C20 C19 0.9(3) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 C20 2.5(4) . . . . ?
C18 C19 C20 C15 -3.0(4) . . . . ?
C20 C15 C16 C17 1.6(3) . . . . ?
