##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_General
_audit_creation_method     'by CrystalStructure 4.0'
_journal_date_recd_electronic     2014-05-28
_journal_date_accepted     2014-05-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      7
_journal_page_first     o743
_journal_page_last     o743
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814012483
_journal_coeditor_code     ZL2591
_publ_contact_author_name     'Yoshinobu Ishikawa'
_publ_contact_author_address
;
School of Pharmaceutical Sciences
University of Shizuoka
52-1 Yada, Suruga-ku, Shizuoka 422-8526
Japan
;
_publ_contact_author_email     'ishi206@u-shizuoka-ken.ac.jp'
_publ_contact_author_fax     '+81-542645645'
_publ_contact_author_phone     '+81-542645645'
_publ_section_title
;
8-Chloro-4-oxo-4H-chromene-3-carbaldehyde
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ishikawa, Yoshinobu' .
;
School of Pharmaceutical Sciences
University of Shizuoka
52-1 Yada, Suruga-ku, Shizuoka 422-8526
Japan
;
_publ_section_synopsis     .
data_I
_database_code_depnum_ccdc_archive     'CCDC '
_chemical_name_systematic
;
8-Chloro-4-oxo-4H-chromene-3-carbaldehyde
;
_chemical_formula_moiety     'C10 H5 Cl O3'
_chemical_formula_sum     'C10 H5 Cl O3'
_chemical_formula_iupac     'C10 H5 Cl O3'
_chemical_formula_weight     208.60
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 '+X,+Y,+Z'
    2 '-X,-Y,-Z'
_cell_length_a     6.9436(15)
_cell_length_b     7.1539(17)
_cell_length_c     9.165(2)
_cell_angle_alpha     102.049(19)
_cell_angle_beta     103.403(17)
_cell_angle_gamma     100.650(19)
_cell_volume     419.89(18)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     15.09
_cell_measurement_theta_max     17.48
_cell_measurement_temperature     100
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.380
_exptl_crystal_size_mid     0.250
_exptl_crystal_size_min     0.100
_exptl_crystal_density_diffrn     1.650
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     212.00
_exptl_absorpt_coefficient_mu     0.425
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.902
_exptl_absorpt_correction_T_max     0.958
_diffrn_ambient_temperature     100
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type     'Rigaku AFC-7R'
_diffrn_measurement_method     ω-2θ
_diffrn_reflns_number     2376
_diffrn_reflns_av_R_equivalents     0.0110
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_decay_%     -0.039
_refine_special_details
;
Refinement was performed using all reflections. The weighted R-factor
(wR) and goodness of fit (S) are based on F².
R-factor (gt) are based on F. The threshold expression of
F² > 2.0 σ(F²) is used only for calculating R-factor
(gt).
;
_reflns_number_total     1932
_reflns_number_gt     1750
_reflns_threshold_expression     F²>2σ(F²)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_gt     0.0275
_refine_ls_wR_factor_ref     0.0753
_refine_ls_goodness_of_fit_ref     1.088
_refine_ls_number_reflns     1932
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0344P)²+0.1939P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_diff_density_max     0.340
_refine_diff_density_min     -0.260
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'H' 'H' 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
    'Cl' 'Cl' 0.1484 0.1585
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'O' 'O' 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
_computing_data_collection
                  'WinAFC Diffractometer Control Software (Rigaku, 1999)'
_computing_cell_refinement
                  'WinAFC Diffractometer Control Software (Rigaku, 1999)'
_computing_data_reduction
                  'WinAFC Diffractometer Control Software (Rigaku, 1999)'
_computing_structure_solution     'SIR2008 (Burla et al., 2007)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'CrystalStructure (Rigaku, 2010)'
_computing_publication_material     'CrystalStructure (Rigaku, 2010)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.28721(5) 0.37563(5) 1.29528(4) 0.02580(11) Uani d . 1.0 2 . .
    O O1 0.21886(13) 0.15266(13) 0.97744(10) 0.0187(2) Uani d . 1.0 2 . .
    O O2 0.63950(15) 0.10011(16) 0.73295(11) 0.0279(3) Uani d . 1.0 2 . .
    O O3 0.04173(16) -0.20711(16) 0.52591(12) 0.0297(3) Uani d . 1.0 2 . .
    C C1 0.16551(19) 0.04262(19) 0.82917(14) 0.0189(3) Uani d . 1.0 2 . .
    C C2 0.29522(19) 0.01959(19) 0.74169(14) 0.0184(3) Uani d . 1.0 2 . .
    C C3 0.51287(19) 0.11867(19) 0.80487(14) 0.0184(3) Uani d . 1.0 2 . .
    C C4 0.76947(18) 0.35541(19) 1.04110(15) 0.0180(3) Uani d . 1.0 2 . .
    C C5 0.81834(19) 0.47543(19) 1.19027(15) 0.0189(3) Uani d . 1.0 2 . .
    C C6 0.66911(19) 0.48195(18) 1.26931(14) 0.0183(3) Uani d . 1.0 2 . .
    C C7 0.47153(19) 0.37036(19) 1.19772(14) 0.0176(3) Uani d . 1.0 2 . .
    C C8 0.56861(18) 0.24423(18) 0.96597(14) 0.0161(3) Uani d . 1.0 2 . .
    C C9 0.41997(18) 0.25375(17) 1.04458(14) 0.0157(3) Uani d . 1.0 2 . .
    C C10 0.2152(2) -0.1091(2) 0.58050(15) 0.0236(3) Uani d . 1.0 2 . .
    H H1 0.0257 -0.0238 0.7828 0.0227 Uiso calc R 1.0 2 . .
    H H2 0.8725 0.3481 0.9891 0.0216 Uiso calc R 1.0 2 . .
    H H3 0.3054 -0.1145 0.5169 0.0284 Uiso calc R 1.0 2 . .
    H H4 0.9536 0.5537 1.2392 0.0226 Uiso calc R 1.0 2 . .
    H H5 0.7035 0.5632 1.3724 0.0220 Uiso calc R 1.0 2 . .
_geom_special_details     .
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C7 . . 1.7243(16) no
    O1 C1 . . 1.3475(15) no
    O1 C9 . . 1.3763(14) no
    O2 C3 . . 1.2250(19) no
    O3 C10 . . 1.2061(16) no
    C1 C2 . . 1.347(2) no
    C2 C3 . . 1.4658(17) no
    C2 C10 . . 1.4836(17) no
    C3 C8 . . 1.4797(17) no
    C4 C5 . . 1.3815(18) no
    C4 C8 . . 1.4029(16) no
    C5 C6 . . 1.397(2) no
    C6 C7 . . 1.3817(17) no
    C7 C9 . . 1.4006(17) no
    C8 C9 . . 1.393(2) no
    C1 H1 . . 0.950 no
    C4 H2 . . 0.950 no
    C5 H4 . . 0.950 no
    C6 H5 . . 0.950 no
    C10 H3 . . 0.950 no
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    Cl1 O1 2.8973(12) . . no
    O1 C3 2.8719(19) . . no
    O2 C1 3.574(2) . . no
    O2 C4 2.8604(17) . . no
    O2 C10 2.9089(18) . . no
    O3 C1 2.8120(17) . . no
    C1 C7 3.5981(19) . . no
    C1 C8 2.7591(18) . . no
    C2 C9 2.7695(18) . . no
    C4 C7 2.783(2) . . no
    C5 C9 2.7806(18) . . no
    C6 C8 2.7921(18) . . no
    Cl1 O2 3.4989(15) . 2_657 no
    Cl1 O3 3.3012(15) . 2_557 no
    Cl1 C5 3.4247(16) . 1_455 no
    O1 O1 3.5617(16) . 2_557 no
    O1 O2 3.5683(17) . 2_657 no
    O1 C3 3.5282(19) . 2_657 no
    O1 C4 3.5456(19) . 2_667 no
    O1 C5 3.359(2) . 2_667 no
    O1 C8 3.5096(19) . 2_657 no
    O2 Cl1 3.4989(15) . 2_657 no
    O2 O1 3.5683(17) . 2_657 no
    O2 C7 3.534(2) . 2_657 no
    O2 C9 3.591(2) . 2_657 no
    O2 C10 3.267(2) . 2_656 no
    O3 Cl1 3.3012(15) . 2_557 no
    O3 O3 3.2307(19) . 2_556 no
    O3 C5 3.2551(18) . 1_444 no
    O3 C6 3.1687(17) . 1_444 no
    O3 C6 3.560(2) . 2_657 no
    O3 C10 3.295(2) . 2_556 no
    C1 C4 3.371(3) . 2_657 no
    C1 C5 3.472(3) . 2_667 no
    C1 C8 3.542(3) . 2_657 no
    C2 C6 3.553(3) . 2_667 no
    C2 C7 3.552(3) . 2_657 no
    C2 C9 3.578(2) . 2_657 no
    C3 O1 3.5282(19) . 2_657 no
    C3 C6 3.460(3) . 2_667 no
    C3 C7 3.515(3) . 2_657 no
    C3 C9 3.304(3) . 2_657 no
    C4 O1 3.5456(19) . 2_667 no
    C4 C1 3.371(3) . 2_657 no
    C4 C7 3.570(3) . 2_667 no
    C4 C9 3.459(3) . 2_667 no
    C5 Cl1 3.4247(16) . 1_655 no
    C5 O1 3.359(2) . 2_667 no
    C5 O3 3.2551(18) . 1_666 no
    C5 C1 3.472(3) . 2_667 no
    C5 C9 3.521(2) . 2_667 no
    C6 O3 3.1687(17) . 1_666 no
    C6 O3 3.560(2) . 2_657 no
    C6 C2 3.553(3) . 2_667 no
    C6 C3 3.460(3) . 2_667 no
    C6 C8 3.538(2) . 2_667 no
    C6 C10 3.387(3) . 2_657 no
    C7 O2 3.534(2) . 2_657 no
    C7 C2 3.552(3) . 2_657 no
    C7 C3 3.515(3) . 2_657 no
    C7 C4 3.570(3) . 2_667 no
    C7 C8 3.427(3) . 2_667 no
    C8 O1 3.5096(19) . 2_657 no
    C8 C1 3.542(3) . 2_657 no
    C8 C6 3.538(2) . 2_667 no
    C8 C7 3.427(3) . 2_667 no
    C8 C9 3.560(2) . 2_657 no
    C8 C9 3.600(2) . 2_667 no
    C9 O2 3.591(2) . 2_657 no
    C9 C2 3.578(2) . 2_657 no
    C9 C3 3.304(3) . 2_657 no
    C9 C4 3.459(3) . 2_667 no
    C9 C5 3.521(2) . 2_667 no
    C9 C8 3.560(2) . 2_657 no
    C9 C8 3.600(2) . 2_667 no
    C10 O2 3.267(2) . 2_656 no
    C10 O3 3.295(2) . 2_556 no
    C10 C6 3.387(3) . 2_657 no
    Cl1 H5 2.8072 . . no
    O2 H2 2.5915 . . no
    O2 H3 2.6355 . . no
    O3 H1 2.4818 . . no
    C1 H3 3.2782 . . no
    C3 H1 3.2929 . . no
    C3 H2 2.6746 . . no
    C3 H3 2.7084 . . no
    C4 H5 3.2636 . . no
    C6 H2 3.2648 . . no
    C7 H4 3.2634 . . no
    C8 H4 3.2730 . . no
    C9 H1 3.1860 . . no
    C9 H2 3.2689 . . no
    C9 H5 3.2672 . . no
    C10 H1 2.5482 . . no
    H1 H3 3.4825 . . no
    H2 H4 2.3282 . . no
    H4 H5 2.3459 . . no
    Cl1 H1 2.8415 . 2_557 no
    Cl1 H2 3.4669 . 1_455 no
    Cl1 H4 2.8395 . 1_455 no
    Cl1 H5 2.9688 . 2_668 no
    O1 H1 3.2499 . 2_557 no
    O1 H2 3.0086 . 1_455 no
    O1 H4 3.3704 . 2_667 no
    O2 H1 2.9439 . 1_655 no
    O2 H3 2.4269 . 2_656 no
    O2 H4 3.3161 . 2_767 no
    O3 H1 3.5460 . 2_556 no
    O3 H4 2.6830 . 1_444 no
    O3 H5 2.5041 . 1_444 no
    O3 H5 3.5184 . 2_657 no
    C1 H2 3.5714 . 1_455 no
    C1 H2 3.5400 . 2_657 no
    C1 H4 3.2889 . 2_667 no
    C2 H5 3.3614 . 2_667 no
    C3 H3 3.4629 . 2_656 no
    C3 H5 3.4282 . 2_667 no
    C4 H1 3.4694 . 2_657 no
    C4 H2 3.0614 . 2_767 no
    C5 H2 3.2259 . 2_767 no
    C6 H3 3.5976 . 2_657 no
    C10 H4 3.3912 . 1_444 no
    C10 H5 3.4945 . 2_657 no
    H1 Cl1 2.8415 . 2_557 no
    H1 O1 3.2499 . 2_557 no
    H1 O2 2.9439 . 1_455 no
    H1 O3 3.5460 . 2_556 no
    H1 C4 3.4694 . 2_657 no
    H1 H2 3.4159 . 1_455 no
    H1 H2 3.4928 . 2_657 no
    H1 H3 3.5853 . 2_556 no
    H1 H4 3.3899 . 2_667 no
    H2 Cl1 3.4669 . 1_655 no
    H2 O1 3.0086 . 1_655 no
    H2 C1 3.5714 . 1_655 no
    H2 C1 3.5400 . 2_657 no
    H2 C4 3.0614 . 2_767 no
    H2 C5 3.2259 . 2_767 no
    H2 H1 3.4159 . 1_655 no
    H2 H1 3.4928 . 2_657 no
    H2 H2 2.4762 . 2_767 no
    H2 H4 2.7931 . 2_767 no
    H3 O2 2.4269 . 2_656 no
    H3 C3 3.4629 . 2_656 no
    H3 C6 3.5976 . 2_657 no
    H3 H1 3.5853 . 2_556 no
    H3 H3 3.0081 . 2_656 no
    H3 H4 3.2450 . 1_444 no
    H3 H5 3.5572 . 2_657 no
    H4 Cl1 2.8395 . 1_655 no
    H4 O1 3.3704 . 2_667 no
    H4 O2 3.3161 . 2_767 no
    H4 O3 2.6830 . 1_666 no
    H4 C1 3.2889 . 2_667 no
    H4 C10 3.3912 . 1_666 no
    H4 H1 3.3899 . 2_667 no
    H4 H2 2.7931 . 2_767 no
    H4 H3 3.2450 . 1_666 no
    H5 Cl1 2.9688 . 2_668 no
    H5 O3 2.5041 . 1_666 no
    H5 O3 3.5184 . 2_657 no
    H5 C2 3.3614 . 2_667 no
    H5 C3 3.4282 . 2_667 no
    H5 C10 3.4945 . 2_657 no
    H5 H3 3.5572 . 2_657 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C1 O1 C9 . . . 118.02(11) no
    O1 C1 C2 . . . 125.01(11) no
    C1 C2 C3 . . . 120.64(11) no
    C1 C2 C10 . . . 119.09(11) no
    C3 C2 C10 . . . 120.26(13) no
    O2 C3 C2 . . . 123.90(11) no
    O2 C3 C8 . . . 122.20(11) no
    C2 C3 C8 . . . 113.90(12) no
    C5 C4 C8 . . . 120.37(13) no
    C4 C5 C6 . . . 120.11(11) no
    C5 C6 C7 . . . 120.09(11) no
    Cl1 C7 C6 . . . 120.35(10) no
    Cl1 C7 C9 . . . 119.75(10) no
    C6 C7 C9 . . . 119.90(13) no
    C3 C8 C4 . . . 121.00(13) no
    C3 C8 C9 . . . 119.81(10) no
    C4 C8 C9 . . . 119.19(11) no
    O1 C9 C7 . . . 117.14(12) no
    O1 C9 C8 . . . 122.57(10) no
    C7 C9 C8 . . . 120.29(11) no
    O3 C10 C2 . . . 123.51(15) no
    O1 C1 H1 . . . 117.494 no
    C2 C1 H1 . . . 117.497 no
    C5 C4 H2 . . . 119.817 no
    C8 C4 H2 . . . 119.815 no
    C4 C5 H4 . . . 119.941 no
    C6 C5 H4 . . . 119.944 no
    C5 C6 H5 . . . 119.956 no
    C7 C6 H5 . . . 119.956 no
    O3 C10 H3 . . . 118.246 no
    C2 C10 H3 . . . 118.242 no
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C1 O1 C9 C7 . . . . 178.77(11) no
    C1 O1 C9 C8 . . . . -0.80(18) no
    C9 O1 C1 C2 . . . . 1.7(2) no
    C9 O1 C1 H1 . . . . -178.3 no
    O1 C1 C2 C3 . . . . -0.5(3) no
    O1 C1 C2 C10 . . . . 179.02(12) no
    H1 C1 C2 C3 . . . . 179.5 no
    H1 C1 C2 C10 . . . . -1.0 no
    C1 C2 C3 O2 . . . . 178.13(14) no
    C1 C2 C3 C8 . . . . -1.5(2) no
    C1 C2 C10 O3 . . . . -5.7(3) no
    C1 C2 C10 H3 . . . . 174.3 no
    C3 C2 C10 O3 . . . . 173.77(13) no
    C3 C2 C10 H3 . . . . -6.2 no
    C10 C2 C3 O2 . . . . -1.3(3) no
    C10 C2 C3 C8 . . . . 179.06(12) no
    O2 C3 C8 C4 . . . . 3.0(3) no
    O2 C3 C8 C9 . . . . -177.39(13) no
    C2 C3 C8 C4 . . . . -177.42(12) no
    C2 C3 C8 C9 . . . . 2.21(19) no
    C5 C4 C8 C3 . . . . 178.54(12) no
    C5 C4 C8 C9 . . . . -1.1(2) no
    C8 C4 C5 C6 . . . . 2.1(3) no
    C8 C4 C5 H4 . . . . -177.9 no
    H2 C4 C5 C6 . . . . -177.9 no
    H2 C4 C5 H4 . . . . 2.1 no
    H2 C4 C8 C3 . . . . -1.5 no
    H2 C4 C8 C9 . . . . 178.9 no
    C4 C5 C6 C7 . . . . -0.9(2) no
    C4 C5 C6 H5 . . . . 179.1 no
    H4 C5 C6 C7 . . . . 179.1 no
    H4 C5 C6 H5 . . . . -0.9 no
    C5 C6 C7 Cl1 . . . . 179.30(12) no
    C5 C6 C7 C9 . . . . -1.3(2) no
    H5 C6 C7 Cl1 . . . . -0.7 no
    H5 C6 C7 C9 . . . . 178.7 no
    Cl1 C7 C9 O1 . . . . 2.11(18) no
    Cl1 C7 C9 C8 . . . . -178.31(9) no
    C6 C7 C9 O1 . . . . -177.27(12) no
    C6 C7 C9 C8 . . . . 2.3(2) no
    C3 C8 C9 O1 . . . . -1.2(2) no
    C3 C8 C9 C7 . . . . 179.27(11) no
    C4 C8 C9 O1 . . . . 178.46(12) no
    C4 C8 C9 C7 . . . . -1.1(2) no
