# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012
data_global
_journal_name_full Chem.Commun.
_journal_coden_cambridge 0182
_publ_contact_author_name 'Prof. Fun, Hoong Kun'
_publ_contact_author_address
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
MALAYSIA
;
_publ_contact_author_email hkfun@usm.my
_publ_contact_author_fax '6 04 6579150'
_publ_contact_author_phone '6 04 6533652'
_publ_requested_category ?
_publ_requested_coeditor_name ?
_publ_contact_letter
;
Date : 18 October 2011
Manager
Cambridge Crystallographic Data Centre
12 Union Road
Cambridge CB2 1EZ
England
Ref: Deposition of Crystal Structure Data -
Paper to be submitted to Chem. Comm.
Dear Sir,
I herewith attach one of the three crystal structure data in
CIF format for a manuscript to be submitted to Chem. Comm..
I request you to kindly acknowledge receipt of this deposition and
send me the CCDC reference number so as to enable me to inform to the
Editor of Chem. Comm..
Yours Sincerely,
Hoong-Kun Fun
;
#============================================================================
# TITLE AND AUTHOR LIST
_publ_section_title
;
Facile and highly atom-economic method to build biaryl-containing medium-ring
lactones
;
loop_
_publ_author_name
_publ_author_address
'Dongdong Wu.'
;
School of Chemistry and Chemical Engineering
Key Lab of Analytical Chemistry for Life Science
Ministry of Education of China
Nanjing University, Nanjing
210093, P. R. China.
;
'Lei Wang.'
;
School of Chemistry and Chemical Engineering
Key Lab of Analytical Chemistry for Life Science
Ministry of Education of China
Nanjing University, Nanjing
210093, P. R. China.
;
'Kai Xu.'
;
School of Chemistry and Chemical Engineering
Key Lab of Analytical Chemistry for Life Science
Ministry of Education of China
Nanjing University, Nanjing
210093, P. R. China.
;
'Jia Song.'
;
School of Chemistry and Chemical Engineering
Key Lab of Analytical Chemistry for Life Science
Ministry of Education of China
Nanjing University, Nanjing
210093, P. R. China.
;
'Hong-Kun Fun.'
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM, Penang
Malaysia
;
'JianHua Xu.'
;
School of Chemistry and Chemical Engineering
Key Lab of Analytical Chemistry for Life Science
Ministry of Education of China
Nanjing University, Nanjing
210093, P. R. China.
;
;
Yan Zhang
;
;
School of Chemistry and Chemical Engineering
Key Lab of Analytical Chemistry for Life Science
Ministry of Education of China
Nanjing University, Nanjing
210093, P. R. China.
;
#=================================================================
data_wdd66_0m
_database_code_depnum_ccdc_archive 'CCDC 849063'
#TrackingRef 'deposition of wdd66, wdd71 & wdd73 cifs.txt'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C23 H16 O6'
_chemical_formula_sum 'C23 H16 O6'
_chemical_formula_weight 388.36
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 9.5616(3)
_cell_length_b 9.3551(3)
_cell_length_c 20.8303(6)
_cell_angle_alpha 90.00
_cell_angle_beta 100.119(1)
_cell_angle_gamma 90.00
_cell_volume 1834.28(10)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(1)
_cell_measurement_reflns_used 9894
_cell_measurement_theta_min 2.39
_cell_measurement_theta_max 33.57
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.63
_exptl_crystal_size_mid 0.37
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.406
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 808
_exptl_absorpt_coefficient_mu 0.102
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9387
_exptl_absorpt_correction_T_max 0.9897
_exptl_absorpt_process_details '(SADABS; Bruker, 2009)'
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0(1)K.
;
_diffrn_ambient_temperature 100.0(1)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 26957
_diffrn_reflns_av_R_equivalents 0.0229
_diffrn_reflns_av_sigmaI/netI 0.0263
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -32
_diffrn_reflns_limit_l_max 32
_diffrn_reflns_theta_min 1.99
_diffrn_reflns_theta_max 33.61
_reflns_number_total 7211
_reflns_number_gt 5848
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 (Bruker, 2009)'
_computing_cell_refinement 'SAINT (Bruker, 2009)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.4946P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7211
_refine_ls_number_parameters 262
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0540
_refine_ls_R_factor_gt 0.0418
_refine_ls_wR_factor_ref 0.1155
_refine_ls_wR_factor_gt 0.1066
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_restrained_S_all 1.040
#_refine_ls_shift/su_max <0.001
#_refine_ls_shift/su_mean <0.001
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28433(7) 0.77300(7) 0.17213(3) 0.01586(12) Uani 1 1 d . . .
O2 O 0.56805(7) 0.74423(8) 0.22567(3) 0.01790(13) Uani 1 1 d . . .
O3 O 0.22791(7) 0.77972(7) 0.27454(3) 0.01626(12) Uani 1 1 d . . .
O4 O 0.38689(7) 0.96741(8) 0.13393(3) 0.02030(14) Uani 1 1 d . . .
O5 O 0.52247(7) 0.54999(7) 0.16006(3) 0.01761(13) Uani 1 1 d . . .
O6 O 0.15084(8) 1.00591(8) 0.25431(4) 0.02501(16) Uani 1 1 d . . .
C1 C 0.33503(9) 0.85061(10) 0.12546(4) 0.01516(15) Uani 1 1 d . . .
C2 C 0.32006(9) 0.76520(10) 0.06404(4) 0.01538(15) Uani 1 1 d . . .
C3 C 0.18782(9) 0.70747(11) 0.03734(4) 0.01887(17) Uani 1 1 d . . .
H3A H 0.1084 0.7234 0.0581 0.023 Uiso 1 1 calc R . .
C4 C 0.17200(10) 0.62696(11) -0.01946(4) 0.02103(18) Uani 1 1 d . . .
H4A H 0.0819 0.5886 -0.0378 0.025 Uiso 1 1 calc R . .
C5 C 0.28905(10) 0.60291(11) -0.04925(4) 0.02124(18) Uani 1 1 d . . .
H5A H 0.2787 0.5481 -0.0882 0.025 Uiso 1 1 calc R . .
C6 C 0.42111(10) 0.65863(11) -0.02235(4) 0.01886(17) Uani 1 1 d . . .
H6A H 0.5001 0.6415 -0.0433 0.023 Uiso 1 1 calc R . .
C7 C 0.43994(9) 0.73944(10) 0.03501(4) 0.01561(15) Uani 1 1 d . . .
C8 C 0.58683(9) 0.78668(10) 0.06400(4) 0.01594(15) Uani 1 1 d . . .
C9 C 0.66463(10) 0.86739(11) 0.02597(5) 0.02084(18) Uani 1 1 d . . .
H9A H 0.6214 0.8955 -0.0168 0.025 Uiso 1 1 calc R . .
C10 C 0.80433(11) 0.90716(12) 0.04981(5) 0.0246(2) Uani 1 1 d . . .
H10A H 0.8558 0.9615 0.0233 0.029 Uiso 1 1 calc R . .
C11 C 0.86886(10) 0.86762(11) 0.11233(5) 0.02243(19) Uani 1 1 d . . .
H11A H 0.9650 0.8928 0.1281 0.027 Uiso 1 1 calc R . .
C12 C 0.79252(9) 0.79123(10) 0.15163(5) 0.01828(16) Uani 1 1 d . . .
H12A H 0.8352 0.7671 0.1950 0.022 Uiso 1 1 calc R . .
C13 C 0.65281(9) 0.74970(10) 0.12754(4) 0.01507(15) Uani 1 1 d . . .
C14 C 0.57434(8) 0.66669(10) 0.17140(4) 0.01476(15) Uani 1 1 d . . .
C15 C 0.46005(9) 0.70841(11) 0.26344(4) 0.01868(17) Uani 1 1 d . . .
H15A H 0.4957 0.7230 0.3106 0.022 Uiso 1 1 calc R . .
H15B H 0.4300 0.6076 0.2562 0.022 Uiso 1 1 calc R . .
C16 C 0.33753(9) 0.80920(10) 0.23927(4) 0.01578(15) Uani 1 1 d . . .
H16A H 0.3680 0.9115 0.2440 0.019 Uiso 1 1 calc R . .
C17 C 0.13629(9) 0.89115(10) 0.27828(4) 0.01576(15) Uani 1 1 d . . .
C18 C 0.02141(9) 0.85261(10) 0.31436(4) 0.01490(15) Uani 1 1 d . . .
C19 C 0.01407(9) 0.71859(10) 0.34252(4) 0.01776(16) Uani 1 1 d . . .
H19A H 0.0839 0.6482 0.3390 0.021 Uiso 1 1 calc R . .
C20 C -0.09626(10) 0.68857(11) 0.37584(5) 0.02136(18) Uani 1 1 d . . .
H20A H -0.1018 0.5973 0.3953 0.026 Uiso 1 1 calc R . .
C21 C -0.19839(10) 0.79140(11) 0.38084(5) 0.02151(18) Uani 1 1 d . . .
H21A H -0.2737 0.7700 0.4036 0.026 Uiso 1 1 calc R . .
C22 C -0.19132(10) 0.92533(12) 0.35283(5) 0.02148(18) Uani 1 1 d . . .
H22A H -0.2615 0.9954 0.3564 0.026 Uiso 1 1 calc R . .
C23 C -0.08113(9) 0.95647(11) 0.31956(5) 0.01941(17) Uani 1 1 d . . .
H23A H -0.0755 1.0480 0.3004 0.023 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0181(3) 0.0181(3) 0.0120(3) -0.0015(2) 0.0045(2) -0.0017(2)
O2 0.0157(3) 0.0240(3) 0.0149(3) -0.0026(2) 0.0052(2) -0.0021(2)
O3 0.0183(3) 0.0162(3) 0.0163(3) -0.0003(2) 0.0085(2) 0.0009(2)
O4 0.0262(3) 0.0161(3) 0.0197(3) -0.0002(2) 0.0073(2) 0.0002(3)
O5 0.0168(3) 0.0172(3) 0.0191(3) 0.0012(2) 0.0039(2) -0.0010(2)
O6 0.0266(3) 0.0218(4) 0.0290(4) 0.0093(3) 0.0114(3) 0.0050(3)
C1 0.0152(3) 0.0170(4) 0.0140(3) 0.0015(3) 0.0044(3) 0.0034(3)
C2 0.0171(3) 0.0164(4) 0.0128(3) 0.0009(3) 0.0028(3) 0.0026(3)
C3 0.0172(3) 0.0240(4) 0.0152(4) 0.0003(3) 0.0022(3) 0.0026(3)
C4 0.0201(4) 0.0263(5) 0.0154(4) -0.0013(3) -0.0006(3) 0.0007(3)
C5 0.0238(4) 0.0248(5) 0.0139(4) -0.0031(3) 0.0000(3) 0.0043(4)
C6 0.0209(4) 0.0222(4) 0.0136(4) -0.0002(3) 0.0036(3) 0.0048(3)
C7 0.0170(3) 0.0173(4) 0.0129(3) 0.0015(3) 0.0037(3) 0.0024(3)
C8 0.0172(3) 0.0157(4) 0.0161(4) 0.0000(3) 0.0061(3) 0.0011(3)
C9 0.0240(4) 0.0215(4) 0.0190(4) 0.0022(3) 0.0093(3) 0.0003(3)
C10 0.0261(4) 0.0228(5) 0.0284(5) 0.0012(4) 0.0145(4) -0.0039(4)
C11 0.0188(4) 0.0214(5) 0.0289(5) -0.0033(4) 0.0089(3) -0.0049(3)
C12 0.0167(3) 0.0183(4) 0.0204(4) -0.0024(3) 0.0046(3) -0.0019(3)
C13 0.0152(3) 0.0147(4) 0.0162(3) -0.0008(3) 0.0050(3) -0.0006(3)
C14 0.0125(3) 0.0186(4) 0.0131(3) 0.0013(3) 0.0019(2) 0.0017(3)
C15 0.0172(3) 0.0260(5) 0.0138(3) 0.0011(3) 0.0053(3) 0.0010(3)
C16 0.0169(3) 0.0190(4) 0.0123(3) -0.0019(3) 0.0052(3) -0.0015(3)
C17 0.0171(3) 0.0177(4) 0.0126(3) -0.0002(3) 0.0028(3) 0.0014(3)
C18 0.0153(3) 0.0173(4) 0.0123(3) -0.0013(3) 0.0028(3) 0.0005(3)
C19 0.0178(3) 0.0174(4) 0.0193(4) -0.0020(3) 0.0065(3) 0.0006(3)
C20 0.0218(4) 0.0190(4) 0.0255(4) -0.0003(3) 0.0104(3) -0.0023(3)
C21 0.0168(3) 0.0264(5) 0.0228(4) -0.0028(4) 0.0075(3) -0.0011(3)
C22 0.0166(3) 0.0256(5) 0.0226(4) -0.0012(4) 0.0046(3) 0.0044(3)
C23 0.0184(3) 0.0202(4) 0.0198(4) 0.0016(3) 0.0039(3) 0.0040(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.3684(10) . ?
O1 C16 1.4420(10) . ?
O2 C14 1.3534(11) . ?
O2 C15 1.4434(11) . ?
O3 C17 1.3727(11) . ?
O3 C16 1.4089(10) . ?
O4 C1 1.2001(11) . ?
O5 C14 1.2052(11) . ?
O6 C17 1.2023(12) . ?
C1 C2 1.4938(12) . ?
C2 C3 1.3974(12) . ?
C2 C7 1.4075(12) . ?
C3 C4 1.3881(13) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3902(13) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3898(13) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3987(13) . ?
C6 H6A 0.9500 . ?
C7 C8 1.4949(12) . ?
C8 C9 1.3993(13) . ?
C8 C13 1.4057(12) . ?
C9 C10 1.3915(14) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3897(15) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3869(13) . ?
C11 H11A 0.9500 . ?
C12 C13 1.3970(12) . ?
C12 H12A 0.9500 . ?
C13 C14 1.4972(12) . ?
C15 C16 1.5191(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 1.0000 . ?
C17 C18 1.4804(12) . ?
C18 C19 1.3911(13) . ?
C18 C23 1.3980(12) . ?
C19 C20 1.3896(12) . ?
C19 H19A 0.9500 . ?
C20 C21 1.3876(14) . ?
C20 H20A 0.9500 . ?
C21 C22 1.3887(15) . ?
C21 H21A 0.9500 . ?
C22 C23 1.3898(13) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
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 C16 117.11(7) . . ?
C14 O2 C15 118.16(7) . . ?
C17 O3 C16 114.93(7) . . ?
O4 C1 O1 124.58(8) . . ?
O4 C1 C2 126.00(8) . . ?
O1 C1 C2 109.40(7) . . ?
C3 C2 C7 120.73(8) . . ?
C3 C2 C1 119.44(8) . . ?
C7 C2 C1 119.79(7) . . ?
C4 C3 C2 120.30(8) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 119.51(9) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C6 C5 C4 120.33(9) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 121.24(8) . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
C6 C7 C2 117.86(8) . . ?
C6 C7 C8 118.40(8) . . ?
C2 C7 C8 123.65(8) . . ?
C9 C8 C13 118.07(8) . . ?
C9 C8 C7 119.08(8) . . ?
C13 C8 C7 122.82(8) . . ?
C10 C9 C8 120.98(9) . . ?
C10 C9 H9A 119.5 . . ?
C8 C9 H9A 119.5 . . ?
C11 C10 C9 120.24(9) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C12 C11 C10 119.82(9) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C13 120.03(9) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C12 C13 C8 120.83(8) . . ?
C12 C13 C14 118.37(8) . . ?
C8 C13 C14 120.80(7) . . ?
O5 C14 O2 124.89(8) . . ?
O5 C14 C13 125.69(8) . . ?
O2 C14 C13 109.41(7) . . ?
O2 C15 C16 105.01(7) . . ?
O2 C15 H15A 110.7 . . ?
C16 C15 H15A 110.7 . . ?
O2 C15 H15B 110.7 . . ?
C16 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
O3 C16 O1 106.96(7) . . ?
O3 C16 C15 107.85(7) . . ?
O1 C16 C15 107.21(7) . . ?
O3 C16 H16A 111.5 . . ?
O1 C16 H16A 111.5 . . ?
C15 C16 H16A 111.5 . . ?
O6 C17 O3 122.20(8) . . ?
O6 C17 C18 125.36(8) . . ?
O3 C17 C18 112.44(8) . . ?
C19 C18 C23 120.37(8) . . ?
C19 C18 C17 122.04(8) . . ?
C23 C18 C17 117.59(8) . . ?
C20 C19 C18 119.45(9) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C21 C20 C19 120.22(9) . . ?
C21 C20 H20A 119.9 . . ?
C19 C20 H20A 119.9 . . ?
C20 C21 C22 120.47(9) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 119.8 . . ?
C21 C22 C23 119.72(9) . . ?
C21 C22 H22A 120.1 . . ?
C23 C22 H22A 120.1 . . ?
C22 C23 C18 119.76(9) . . ?
C22 C23 H23A 120.1 . . ?
C18 C23 H23A 120.1 . . ?
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
C16 O1 C1 O4 -21.65(12) . . . . ?
C16 O1 C1 C2 156.39(7) . . . . ?
O4 C1 C2 C3 -128.97(10) . . . . ?
O1 C1 C2 C3 53.02(11) . . . . ?
O4 C1 C2 C7 53.29(13) . . . . ?
O1 C1 C2 C7 -124.71(8) . . . . ?
C7 C2 C3 C4 -1.84(14) . . . . ?
C1 C2 C3 C4 -179.55(9) . . . . ?
C2 C3 C4 C5 0.65(15) . . . . ?
C3 C4 C5 C6 0.19(15) . . . . ?
C4 C5 C6 C7 0.16(15) . . . . ?
C5 C6 C7 C2 -1.29(14) . . . . ?
C5 C6 C7 C8 175.42(9) . . . . ?
C3 C2 C7 C6 2.12(13) . . . . ?
C1 C2 C7 C6 179.82(8) . . . . ?
C3 C2 C7 C8 -174.40(9) . . . . ?
C1 C2 C7 C8 3.30(13) . . . . ?
C6 C7 C8 C9 56.73(12) . . . . ?
C2 C7 C8 C9 -126.77(10) . . . . ?
C6 C7 C8 C13 -121.18(10) . . . . ?
C2 C7 C8 C13 55.32(13) . . . . ?
C13 C8 C9 C10 1.43(14) . . . . ?
C7 C8 C9 C10 -176.58(9) . . . . ?
C8 C9 C10 C11 -0.34(16) . . . . ?
C9 C10 C11 C12 -1.57(16) . . . . ?
C10 C11 C12 C13 2.34(15) . . . . ?
C11 C12 C13 C8 -1.22(14) . . . . ?
C11 C12 C13 C14 179.67(9) . . . . ?
C9 C8 C13 C12 -0.65(13) . . . . ?
C7 C8 C13 C12 177.28(8) . . . . ?
C9 C8 C13 C14 178.43(8) . . . . ?
C7 C8 C13 C14 -3.64(13) . . . . ?
C15 O2 C14 O5 -19.24(12) . . . . ?
C15 O2 C14 C13 159.63(7) . . . . ?
C12 C13 C14 O5 -122.10(10) . . . . ?
C8 C13 C14 O5 58.79(13) . . . . ?
C12 C13 C14 O2 59.04(10) . . . . ?
C8 C13 C14 O2 -120.07(9) . . . . ?
C14 O2 C15 C16 -95.28(9) . . . . ?
C17 O3 C16 O1 -89.37(8) . . . . ?
C17 O3 C16 C15 155.59(7) . . . . ?
C1 O1 C16 O3 149.05(7) . . . . ?
C1 O1 C16 C15 -95.48(9) . . . . ?
O2 C15 C16 O3 -179.90(7) . . . . ?
O2 C15 C16 O1 65.23(9) . . . . ?
C16 O3 C17 O6 -1.47(12) . . . . ?
C16 O3 C17 C18 178.48(7) . . . . ?
O6 C17 C18 C19 -177.96(9) . . . . ?
O3 C17 C18 C19 2.09(11) . . . . ?
O6 C17 C18 C23 1.91(13) . . . . ?
O3 C17 C18 C23 -178.04(8) . . . . ?
C23 C18 C19 C20 0.10(13) . . . . ?
C17 C18 C19 C20 179.96(8) . . . . ?
C18 C19 C20 C21 0.14(14) . . . . ?
C19 C20 C21 C22 -0.20(15) . . . . ?
C20 C21 C22 C23 0.02(15) . . . . ?
C21 C22 C23 C18 0.22(14) . . . . ?
C19 C18 C23 C22 -0.28(13) . . . . ?
C17 C18 C23 C22 179.85(8) . . . . ?
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full 33.61
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.482
_refine_diff_density_min -0.239
_refine_diff_density_rms 0.053
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
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C16 H16A O5 1.0000 2.4600 3.2058(11) 131.00 2_655 yes
C22 H22A O5 0.9500 2.5100 3.3405(12) 146.00 2_555 yes
#==============================================================================
data_mo_wdd71_0m
_database_code_depnum_ccdc_archive 'CCDC 849064'
#TrackingRef 'deposition of wdd66, wdd71 & wdd73 cifs.txt'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C20 H14 N2 O4'
_chemical_formula_sum 'C20 H14 N2 O4'
_chemical_formula_weight 346.33
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'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 8.6883(4)
_cell_length_b 17.1238(7)
_cell_length_c 11.0471(4)
_cell_angle_alpha 90.00
_cell_angle_beta 95.9460(10)
_cell_angle_gamma 90.00
_cell_volume 1634.71(12)
_cell_formula_units_Z 4
_cell_measurement_temperature 297(2)
_cell_measurement_reflns_used 5956
_cell_measurement_theta_min 2.36
_cell_measurement_theta_max 30.55
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.29
_exptl_crystal_size_min 0.21
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.407
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 720
_exptl_absorpt_coefficient_mu 0.100
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9657
_exptl_absorpt_correction_T_max 0.9792
_exptl_absorpt_process_details '(SADABS; Bruker, 2009)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 297(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type
;
Bruker SMART APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 25268
_diffrn_reflns_av_R_equivalents 0.0300
_diffrn_reflns_av_sigmaI/netI 0.0301
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -26
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.20
_diffrn_reflns_theta_max 33.74
_reflns_number_total 6484
_reflns_number_gt 4244
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 (Bruker, 2009)'
_computing_cell_refinement 'SAINT (Bruker, 2009)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0874P)^2^+0.1527P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 6484
_refine_ls_number_parameters 235
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0823
_refine_ls_R_factor_gt 0.0500
_refine_ls_wR_factor_ref 0.1643
_refine_ls_wR_factor_gt 0.1419
_refine_ls_goodness_of_fit_ref 1.016
_refine_ls_restrained_S_all 1.016
#_refine_ls_shift/su_max <0.001
#_refine_ls_shift/su_mean <0.001
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.00964(10) -0.00296(5) 0.29754(8) 0.0419(2) Uani 1 1 d . . .
O2 O 0.77842(9) 0.05582(5) 0.30771(7) 0.03496(18) Uani 1 1 d . . .
O3 O 0.56956(10) -0.08582(6) 0.27607(9) 0.0490(2) Uani 1 1 d . . .
O4 O 0.77154(10) -0.08593(5) 0.42291(7) 0.03608(19) Uani 1 1 d . . .
N1 N 0.74346(17) -0.08387(7) -0.04358(10) 0.0520(3) Uani 1 1 d . . .
N2 N 0.92917(16) -0.19614(7) 0.08285(11) 0.0520(3) Uani 1 1 d . . .
C1 C 0.7029(2) -0.02142(10) -0.11125(13) 0.0593(4) Uani 1 1 d . . .
H1A H 0.6604 -0.0297 -0.1910 0.071 Uiso 1 1 calc R . .
C2 C 0.7194(2) 0.05420(9) -0.07161(13) 0.0579(4) Uani 1 1 d . . .
H2A H 0.6904 0.0958 -0.1231 0.069 Uiso 1 1 calc R . .
C3 C 0.78014(18) 0.06674(8) 0.04680(12) 0.0466(3) Uani 1 1 d . . .
H3A H 0.7921 0.1173 0.0770 0.056 Uiso 1 1 calc R . .
C4 C 0.82346(13) 0.00313(7) 0.12088(10) 0.0338(2) Uani 1 1 d . . .
C5 C 0.80407(15) -0.07188(7) 0.07191(10) 0.0368(2) Uani 1 1 d . . .
C6 C 0.84356(14) -0.14588(7) 0.14079(11) 0.0369(2) Uani 1 1 d . . .
C7 C 0.9609(2) -0.26557(9) 0.13521(16) 0.0599(4) Uani 1 1 d . . .
H7A H 1.0194 -0.3007 0.0950 0.072 Uiso 1 1 calc R . .
C8 C 0.9130(2) -0.28836(8) 0.24410(15) 0.0557(4) Uani 1 1 d . . .
H8A H 0.9370 -0.3377 0.2757 0.067 Uiso 1 1 calc R . .
C9 C 0.82865(16) -0.23647(7) 0.30552(12) 0.0440(3) Uani 1 1 d . . .
H9A H 0.7970 -0.2495 0.3808 0.053 Uiso 1 1 calc R . .
C10 C 0.79164(13) -0.16427(6) 0.25295(10) 0.0338(2) Uani 1 1 d . . .
C11 C 0.69510(13) -0.10862(6) 0.31558(10) 0.0339(2) Uani 1 1 d . . .
C12 C 0.71112(15) -0.01806(7) 0.47854(12) 0.0396(3) Uani 1 1 d . . .
H12A H 0.7264 -0.0232 0.5664 0.048 Uiso 1 1 calc R . .
H12B H 0.6009 -0.0138 0.4543 0.048 Uiso 1 1 calc R . .
C13 C 0.79287(13) 0.05509(7) 0.43983(10) 0.0330(2) Uani 1 1 d . . .
H13A H 0.9021 0.0545 0.4725 0.040 Uiso 1 1 calc R . .
C14 C 0.88520(12) 0.01706(6) 0.25020(10) 0.0312(2) Uani 1 1 d . . .
C15 C 0.71297(13) 0.12644(7) 0.48339(11) 0.0344(2) Uani 1 1 d . . .
C16 C 0.76161(16) 0.15780(8) 0.59647(13) 0.0454(3) Uani 1 1 d . . .
H16A H 0.8462 0.1363 0.6433 0.055 Uiso 1 1 calc R . .
C17 C 0.68466(18) 0.22113(9) 0.64008(15) 0.0544(4) Uani 1 1 d . . .
H17A H 0.7173 0.2416 0.7164 0.065 Uiso 1 1 calc R . .
C18 C 0.56019(18) 0.25378(8) 0.57099(16) 0.0547(4) Uani 1 1 d . . .
H18A H 0.5098 0.2968 0.5999 0.066 Uiso 1 1 calc R . .
C19 C 0.51068(18) 0.22260(9) 0.45907(16) 0.0583(4) Uani 1 1 d . . .
H19A H 0.4263 0.2445 0.4125 0.070 Uiso 1 1 calc R . .
C20 C 0.58550(17) 0.15872(8) 0.41499(13) 0.0486(3) Uani 1 1 d . . .
H20A H 0.5504 0.1375 0.3397 0.058 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0352(4) 0.0529(5) 0.0370(4) -0.0024(4) 0.0009(3) 0.0040(4)
O2 0.0385(4) 0.0370(4) 0.0291(4) 0.0001(3) 0.0026(3) 0.0053(3)
O3 0.0361(4) 0.0501(5) 0.0585(6) 0.0018(4) -0.0053(4) 0.0025(4)
O4 0.0414(4) 0.0332(4) 0.0332(4) 0.0008(3) 0.0017(3) 0.0036(3)
N1 0.0755(8) 0.0479(6) 0.0303(5) -0.0028(5) -0.0062(5) 0.0011(6)
N2 0.0702(8) 0.0426(6) 0.0436(6) -0.0064(5) 0.0074(5) 0.0127(5)
C1 0.0854(11) 0.0606(9) 0.0285(6) 0.0051(6) -0.0101(6) 0.0034(8)
C2 0.0821(11) 0.0525(8) 0.0362(7) 0.0139(6) -0.0069(7) 0.0072(7)
C3 0.0642(8) 0.0363(6) 0.0381(6) 0.0062(5) -0.0010(6) 0.0040(5)
C4 0.0391(5) 0.0344(5) 0.0277(5) 0.0029(4) 0.0028(4) 0.0009(4)
C5 0.0466(6) 0.0356(5) 0.0276(5) 0.0001(4) 0.0009(4) 0.0018(4)
C6 0.0469(6) 0.0312(5) 0.0313(5) -0.0028(4) -0.0026(4) 0.0019(4)
C7 0.0772(10) 0.0440(7) 0.0582(9) -0.0078(7) 0.0045(8) 0.0214(7)
C8 0.0703(9) 0.0356(6) 0.0589(9) 0.0029(6) -0.0049(7) 0.0146(6)
C9 0.0537(7) 0.0347(6) 0.0420(7) 0.0056(5) -0.0035(5) 0.0026(5)
C10 0.0381(5) 0.0287(5) 0.0330(5) 0.0003(4) -0.0043(4) -0.0003(4)
C11 0.0361(5) 0.0300(5) 0.0352(5) 0.0047(4) 0.0016(4) -0.0039(4)
C12 0.0464(6) 0.0379(6) 0.0362(6) -0.0012(5) 0.0114(5) 0.0029(5)
C13 0.0338(5) 0.0367(5) 0.0279(5) -0.0012(4) 0.0002(4) 0.0036(4)
C14 0.0352(5) 0.0285(5) 0.0301(5) 0.0018(4) 0.0036(4) -0.0019(4)
C15 0.0351(5) 0.0331(5) 0.0354(5) -0.0001(4) 0.0048(4) 0.0029(4)
C16 0.0440(6) 0.0471(7) 0.0439(7) -0.0093(5) -0.0013(5) 0.0068(5)
C17 0.0568(8) 0.0487(7) 0.0577(9) -0.0196(7) 0.0064(7) 0.0018(6)
C18 0.0561(8) 0.0359(6) 0.0747(11) -0.0065(6) 0.0188(7) 0.0077(6)
C19 0.0559(8) 0.0522(8) 0.0658(10) 0.0059(7) 0.0020(7) 0.0222(7)
C20 0.0516(7) 0.0501(7) 0.0424(7) -0.0014(6) -0.0031(6) 0.0140(6)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C14 1.2012(14) . ?
O2 C14 1.3516(13) . ?
O2 C13 1.4519(13) . ?
O3 C11 1.1975(14) . ?
O4 C11 1.3546(14) . ?
O4 C12 1.4390(14) . ?
N1 C1 1.3313(19) . ?
N1 C5 1.3447(16) . ?
N2 C7 1.338(2) . ?
N2 C6 1.3425(16) . ?
C1 C2 1.370(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.376(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.3907(17) . ?
C3 H3A 0.9300 . ?
C4 C5 1.3971(16) . ?
C4 C14 1.4923(16) . ?
C5 C6 1.4994(16) . ?
C6 C10 1.3977(17) . ?
C7 C8 1.370(2) . ?
C7 H7A 0.9300 . ?
C8 C9 1.375(2) . ?
C8 H8A 0.9300 . ?
C9 C10 1.3895(16) . ?
C9 H9A 0.9300 . ?
C10 C11 1.4868(16) . ?
C12 C13 1.5229(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C15 1.5085(15) . ?
C13 H13A 0.9800 . ?
C15 C16 1.3850(18) . ?
C15 C20 1.3891(17) . ?
C16 C17 1.3863(19) . ?
C16 H16A 0.9300 . ?
C17 C18 1.376(2) . ?
C17 H17A 0.9300 . ?
C18 C19 1.374(2) . ?
C18 H18A 0.9300 . ?
C19 C20 1.386(2) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
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
C14 O2 C13 118.44(8) . . ?
C11 O4 C12 115.98(9) . . ?
C1 N1 C5 117.72(12) . . ?
C7 N2 C6 117.58(13) . . ?
N1 C1 C2 124.55(13) . . ?
N1 C1 H1A 117.7 . . ?
C2 C1 H1A 117.7 . . ?
C1 C2 C3 117.95(13) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 C4 119.40(13) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 C5 118.55(11) . . ?
C3 C4 C14 119.12(10) . . ?
C5 C4 C14 122.32(10) . . ?
N1 C5 C4 121.83(11) . . ?
N1 C5 C6 113.52(10) . . ?
C4 C5 C6 124.64(10) . . ?
N2 C6 C10 121.59(11) . . ?
N2 C6 C5 114.12(11) . . ?
C10 C6 C5 124.22(10) . . ?
N2 C7 C8 124.39(14) . . ?
N2 C7 H7A 117.8 . . ?
C8 C7 H7A 117.8 . . ?
C7 C8 C9 118.39(13) . . ?
C7 C8 H8A 120.8 . . ?
C9 C8 H8A 120.8 . . ?
C8 C9 C10 118.75(13) . . ?
C8 C9 H9A 120.6 . . ?
C10 C9 H9A 120.6 . . ?
C9 C10 C6 119.27(11) . . ?
C9 C10 C11 119.55(11) . . ?
C6 C10 C11 121.17(10) . . ?
O3 C11 O4 124.82(11) . . ?
O3 C11 C10 125.16(11) . . ?
O4 C11 C10 110.00(9) . . ?
O4 C12 C13 110.06(9) . . ?
O4 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
O4 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
O2 C13 C15 108.60(9) . . ?
O2 C13 C12 107.16(9) . . ?
C15 C13 C12 109.46(9) . . ?
O2 C13 H13A 110.5 . . ?
C15 C13 H13A 110.5 . . ?
C12 C13 H13A 110.5 . . ?
O1 C14 O2 124.48(10) . . ?
O1 C14 C4 126.11(10) . . ?
O2 C14 C4 109.41(9) . . ?
C16 C15 C20 119.21(11) . . ?
C16 C15 C13 119.62(10) . . ?
C20 C15 C13 121.07(11) . . ?
C15 C16 C17 120.24(13) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C18 C17 C16 120.31(14) . . ?
C18 C17 H17A 119.8 . . ?
C16 C17 H17A 119.8 . . ?
C19 C18 C17 119.73(13) . . ?
C19 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C18 C19 C20 120.54(14) . . ?
C18 C19 H19A 119.7 . . ?
C20 C19 H19A 119.7 . . ?
C19 C20 C15 119.95(13) . . ?
C19 C20 H20A 120.0 . . ?
C15 C20 H20A 120.0 . . ?
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
C5 N1 C1 C2 0.4(3) . . . . ?
N1 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 C14 -178.32(13) . . . . ?
C1 N1 C5 C4 0.5(2) . . . . ?
C1 N1 C5 C6 179.10(14) . . . . ?
C3 C4 C5 N1 -0.77(19) . . . . ?
C14 C4 C5 N1 177.72(12) . . . . ?
C3 C4 C5 C6 -179.24(12) . . . . ?
C14 C4 C5 C6 -0.75(19) . . . . ?
C7 N2 C6 C10 1.3(2) . . . . ?
C7 N2 C6 C5 -175.94(13) . . . . ?
N1 C5 C6 N2 50.57(16) . . . . ?
C4 C5 C6 N2 -130.85(13) . . . . ?
N1 C5 C6 C10 -126.57(13) . . . . ?
C4 C5 C6 C10 52.01(18) . . . . ?
C6 N2 C7 C8 -0.6(3) . . . . ?
N2 C7 C8 C9 -1.1(3) . . . . ?
C7 C8 C9 C10 1.9(2) . . . . ?
C8 C9 C10 C6 -1.25(19) . . . . ?
C8 C9 C10 C11 177.53(12) . . . . ?
N2 C6 C10 C9 -0.40(18) . . . . ?
C5 C6 C10 C9 176.54(11) . . . . ?
N2 C6 C10 C11 -179.16(11) . . . . ?
C5 C6 C10 C11 -2.23(18) . . . . ?
C12 O4 C11 O3 -13.85(16) . . . . ?
C12 O4 C11 C10 164.72(9) . . . . ?
C9 C10 C11 O3 -116.83(14) . . . . ?
C6 C10 C11 O3 61.93(16) . . . . ?
C9 C10 C11 O4 64.61(13) . . . . ?
C6 C10 C11 O4 -116.63(11) . . . . ?
C11 O4 C12 C13 -92.75(12) . . . . ?
C14 O2 C13 C15 155.23(9) . . . . ?
C14 O2 C13 C12 -86.62(11) . . . . ?
O4 C12 C13 O2 54.11(12) . . . . ?
O4 C12 C13 C15 171.70(9) . . . . ?
C13 O2 C14 O1 -17.85(16) . . . . ?
C13 O2 C14 C4 161.78(9) . . . . ?
C3 C4 C14 O1 -121.57(14) . . . . ?
C5 C4 C14 O1 59.95(17) . . . . ?
C3 C4 C14 O2 58.80(14) . . . . ?
C5 C4 C14 O2 -119.68(12) . . . . ?
O2 C13 C15 C16 -152.72(11) . . . . ?
C12 C13 C15 C16 90.59(14) . . . . ?
O2 C13 C15 C20 30.99(15) . . . . ?
C12 C13 C15 C20 -85.69(14) . . . . ?
C20 C15 C16 C17 -0.6(2) . . . . ?
C13 C15 C16 C17 -176.98(13) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C19 1.0(2) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C15 -0.9(2) . . . . ?
C16 C15 C20 C19 1.4(2) . . . . ?
C13 C15 C20 C19 177.66(13) . . . . ?
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full 33.74
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max 0.287
_refine_diff_density_min -0.198
_refine_diff_density_rms 0.045
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
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C9 H9A N2 0.93 2.58 3.3055(18) 135.6 4_556 yes
#============================================================================
data_wdd73a_0m
_database_code_depnum_ccdc_archive 'CCDC 849065'
#TrackingRef 'deposition of wdd66, wdd71 & wdd73 cifs.txt'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C23 H18 O4'
_chemical_formula_weight 358.37
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting ?
_symmetry_space_group_name_H-M ?
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 8.51370(10)
_cell_length_b 17.0468(2)
_cell_length_c 12.05680(10)
_cell_angle_alpha 90.00
_cell_angle_beta 90.0340(10)
_cell_angle_gamma 90.00
_cell_volume 1749.82(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(1)
_cell_measurement_reflns_used 9925
_cell_measurement_theta_min 2.39
_cell_measurement_theta_max 33.62
_exptl_crystal_description block
_exptl_crystal_colour colourless
#_exptl_crystal_colour ?
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.19
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.360
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 752
_exptl_absorpt_coefficient_mu 0.093
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9744
_exptl_absorpt_correction_T_max 0.9825
_exptl_absorpt_process_details '(SADABS; Bruker, 2009)'
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0 (1) K.
;
_diffrn_ambient_temperature 100
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_diffrn_reflns_number 50813
_diffrn_reflns_av_R_equivalents 0.0506
_diffrn_reflns_av_sigmaI/netI 0.0364
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -26
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 2.07
_diffrn_reflns_theta_max 33.82
_reflns_number_total 7034
_reflns_number_gt 5390
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'APEX2 (Bruker, 2009)'
_computing_cell_refinement 'SAINT (Bruker, 2009)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement SHELXTL
_computing_molecular_graphics SHELXTL
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.7063P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 7034
_refine_ls_number_parameters 245
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0772
_refine_ls_R_factor_gt 0.0553
_refine_ls_wR_factor_ref 0.1424
_refine_ls_wR_factor_gt 0.1291
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_restrained_S_all 1.036
#_refine_ls_shift/su_max <0.001
#_refine_ls_shift/su_mean <0.001
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.52380(10) 0.50241(5) 0.84128(7) 0.02044(17) Uani 1 1 d . . .
O2 O 0.43683(10) 0.62841(5) 0.84080(7) 0.01710(16) Uani 1 1 d . . .
O3 O 0.76139(11) 0.71371(5) 0.81002(7) 0.02234(18) Uani 1 1 d . . .
O4 O 0.71113(10) 0.63070(5) 0.95359(7) 0.01822(16) Uani 1 1 d . . .
C1 C 0.72441(14) 0.58381(7) 0.52428(9) 0.0196(2) Uani 1 1 d . . .
H1A H 0.8285 0.5796 0.4965 0.024 Uiso 1 1 calc R . .
C2 C 0.60307(16) 0.60188(7) 0.45150(10) 0.0219(2) Uani 1 1 d . . .
H2A H 0.6245 0.6089 0.3748 0.026 Uiso 1 1 calc R . .
C3 C 0.45072(15) 0.60960(7) 0.49070(10) 0.0210(2) Uani 1 1 d . . .
H3A H 0.3674 0.6214 0.4410 0.025 Uiso 1 1 calc R . .
C4 C 0.42066(14) 0.60004(7) 0.60330(10) 0.0187(2) Uani 1 1 d . . .
H4A H 0.3172 0.6073 0.6309 0.022 Uiso 1 1 calc R . .
C5 C 0.54198(13) 0.57977(6) 0.67588(9) 0.01557(19) Uani 1 1 d . . .
C6 C 0.69707(13) 0.57165(6) 0.63750(9) 0.01592(19) Uani 1 1 d . . .
C7 C 0.83289(13) 0.54869(7) 0.70916(9) 0.0165(2) Uani 1 1 d . . .
C8 C 0.93103(14) 0.48786(7) 0.67256(10) 0.0205(2) Uani 1 1 d . . .
H8A H 0.9092 0.4631 0.6036 0.025 Uiso 1 1 calc R . .
C9 C 1.05930(15) 0.46281(8) 0.73452(11) 0.0230(2) Uani 1 1 d . . .
H9A H 1.1244 0.4219 0.7072 0.028 Uiso 1 1 calc R . .
C10 C 1.09263(14) 0.49729(8) 0.83607(11) 0.0227(2) Uani 1 1 d . . .
H10A H 1.1800 0.4801 0.8787 0.027 Uiso 1 1 calc R . .
C11 C 0.99663(14) 0.55729(7) 0.87467(10) 0.0202(2) Uani 1 1 d . . .
H11A H 1.0175 0.5805 0.9448 0.024 Uiso 1 1 calc R . .
C12 C 0.86952(13) 0.58388(7) 0.81130(9) 0.0170(2) Uani 1 1 d . . .
C13 C 0.77606(13) 0.65130(7) 0.85520(9) 0.0172(2) Uani 1 1 d . . .
C14 C 0.58139(14) 0.67815(7) 0.99506(10) 0.0188(2) Uani 1 1 d . . .
H14A H 0.5826 0.7311 0.9593 0.023 Uiso 1 1 calc R . .
C15 C 0.43175(13) 0.63287(7) 0.96111(9) 0.0168(2) Uani 1 1 d . . .
H15A H 0.4324 0.5790 0.9941 0.020 Uiso 1 1 calc R . .
C16 C 0.50144(13) 0.56383(7) 0.79434(9) 0.01599(19) Uani 1 1 d . . .
C17 C 0.28530(13) 0.67627(7) 0.99471(9) 0.0163(2) Uani 1 1 d . . .
C18 C 0.22055(14) 0.66276(7) 1.09937(10) 0.0201(2) Uani 1 1 d . . .
H18A H 0.2650 0.6241 1.1466 0.024 Uiso 1 1 calc R . .
C19 C 0.09114(15) 0.70584(8) 1.13453(10) 0.0223(2) Uani 1 1 d . . .
H19A H 0.0490 0.6972 1.2065 0.027 Uiso 1 1 calc R . .
C20 C 0.02291(14) 0.76138(7) 1.06520(11) 0.0221(2) Uani 1 1 d . . .
H20A H -0.0648 0.7911 1.0898 0.027 Uiso 1 1 calc R . .
C21 C 0.08385(14) 0.77317(7) 0.95962(11) 0.0213(2) Uani 1 1 d . . .
H21A H 0.0357 0.8099 0.9111 0.026 Uiso 1 1 calc R . .
C22 C 0.21533(14) 0.73130(7) 0.92470(10) 0.0185(2) Uani 1 1 d . . .
H22A H 0.2576 0.7402 0.8529 0.022 Uiso 1 1 calc R . .
C23 C 0.60226(15) 0.68598(8) 1.11932(10) 0.0227(2) Uani 1 1 d . . .
H23A H 0.7070 0.7070 1.1353 0.034 Uiso 1 1 calc R . .
H23B H 0.5911 0.6343 1.1541 0.034 Uiso 1 1 calc R . .
H23C H 0.5223 0.7216 1.1489 0.034 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0235(4) 0.0169(4) 0.0209(4) 0.0020(3) -0.0004(3) -0.0005(3)
O2 0.0198(4) 0.0180(4) 0.0135(3) -0.0012(3) -0.0017(3) 0.0024(3)
O3 0.0239(4) 0.0217(4) 0.0215(4) 0.0006(3) -0.0032(3) 0.0012(3)
O4 0.0179(4) 0.0195(4) 0.0172(4) 0.0005(3) -0.0003(3) 0.0017(3)
C1 0.0217(5) 0.0214(5) 0.0158(5) 0.0001(4) -0.0013(4) -0.0007(4)
C2 0.0278(6) 0.0220(6) 0.0160(5) 0.0008(4) -0.0039(4) 0.0007(4)
C3 0.0257(6) 0.0194(5) 0.0180(5) 0.0000(4) -0.0078(4) 0.0020(4)
C4 0.0189(5) 0.0181(5) 0.0191(5) -0.0006(4) -0.0036(4) 0.0012(4)
C5 0.0176(5) 0.0139(4) 0.0153(5) -0.0012(4) -0.0024(4) -0.0007(4)
C6 0.0181(5) 0.0150(5) 0.0146(4) -0.0009(4) -0.0033(4) -0.0006(4)
C7 0.0150(4) 0.0190(5) 0.0153(5) 0.0015(4) -0.0011(4) -0.0016(4)
C8 0.0190(5) 0.0231(5) 0.0195(5) 0.0008(4) -0.0004(4) 0.0015(4)
C9 0.0186(5) 0.0257(6) 0.0247(6) 0.0023(5) 0.0009(4) 0.0043(4)
C10 0.0163(5) 0.0283(6) 0.0236(6) 0.0047(5) -0.0025(4) 0.0022(4)
C11 0.0178(5) 0.0254(6) 0.0174(5) 0.0021(4) -0.0039(4) -0.0032(4)
C12 0.0162(5) 0.0189(5) 0.0159(5) 0.0017(4) -0.0015(4) -0.0024(4)
C13 0.0152(5) 0.0209(5) 0.0156(5) -0.0014(4) -0.0038(4) -0.0030(4)
C14 0.0180(5) 0.0191(5) 0.0193(5) -0.0023(4) -0.0010(4) 0.0019(4)
C15 0.0174(5) 0.0196(5) 0.0135(4) -0.0004(4) -0.0019(4) 0.0013(4)
C16 0.0138(4) 0.0173(5) 0.0168(5) -0.0010(4) -0.0027(3) -0.0014(4)
C17 0.0161(5) 0.0168(5) 0.0160(5) -0.0021(4) -0.0013(4) -0.0009(4)
C18 0.0204(5) 0.0221(5) 0.0178(5) 0.0013(4) -0.0017(4) 0.0007(4)
C19 0.0217(5) 0.0257(6) 0.0196(5) -0.0008(4) 0.0032(4) -0.0005(4)
C20 0.0189(5) 0.0219(6) 0.0256(6) -0.0022(4) 0.0025(4) 0.0012(4)
C21 0.0202(5) 0.0194(5) 0.0243(6) 0.0016(4) -0.0012(4) 0.0019(4)
C22 0.0189(5) 0.0184(5) 0.0182(5) 0.0006(4) -0.0006(4) 0.0005(4)
C23 0.0209(5) 0.0284(6) 0.0187(5) -0.0056(4) -0.0019(4) -0.0015(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C16 1.2053(14) . ?
O2 C16 1.3522(14) . ?
O2 C15 1.4532(13) . ?
O3 C13 1.2017(15) . ?
O4 C13 1.3553(14) . ?
O4 C14 1.4577(14) . ?
C1 C2 1.3896(17) . ?
C1 C6 1.4003(16) . ?
C1 H1A 0.9500 . ?
C2 C3 1.3870(18) . ?
C2 H2A 0.9500 . ?
C3 C4 1.3912(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3967(16) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4062(16) . ?
C5 C16 1.4945(16) . ?
C6 C7 1.4951(16) . ?
C7 C8 1.4031(17) . ?
C7 C12 1.4048(16) . ?
C8 C9 1.3900(17) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3872(19) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3897(18) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3998(16) . ?
C11 H11A 0.9500 . ?
C12 C13 1.4950(16) . ?
C14 C23 1.5144(17) . ?
C14 C15 1.5447(17) . ?
C14 H14A 1.0000 . ?
C15 C17 1.5056(16) . ?
C15 H15A 1.0000 . ?
C17 C22 1.3952(16) . ?
C17 C18 1.3964(16) . ?
C18 C19 1.3905(17) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3899(18) . ?
C19 H19A 0.9500 . ?
C20 C21 1.3896(18) . ?
C20 H20A 0.9500 . ?
C21 C22 1.3930(17) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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
C16 O2 C15 117.93(9) . . ?
C13 O4 C14 117.77(9) . . ?
C2 C1 C6 121.63(11) . . ?
C2 C1 H1A 119.2 . . ?
C6 C1 H1A 119.2 . . ?
C3 C2 C1 120.06(11) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C2 C3 C4 119.60(11) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 120.26(11) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.82(10) . . ?
C4 C5 C16 118.20(10) . . ?
C6 C5 C16 120.93(10) . . ?
C1 C6 C5 117.57(10) . . ?
C1 C6 C7 118.24(10) . . ?
C5 C6 C7 124.17(10) . . ?
C8 C7 C12 117.35(10) . . ?
C8 C7 C6 118.18(10) . . ?
C12 C7 C6 124.47(10) . . ?
C9 C8 C7 121.73(11) . . ?
C9 C8 H8A 119.1 . . ?
C7 C8 H8A 119.1 . . ?
C10 C9 C8 120.29(12) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 119.17(11) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
C10 C11 C12 120.67(11) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C11 C12 C7 120.76(11) . . ?
C11 C12 C13 117.85(10) . . ?
C7 C12 C13 121.39(10) . . ?
O3 C13 O4 125.73(11) . . ?
O3 C13 C12 125.12(11) . . ?
O4 C13 C12 109.15(10) . . ?
O4 C14 C23 107.44(9) . . ?
O4 C14 C15 104.88(9) . . ?
C23 C14 C15 113.73(10) . . ?
O4 C14 H14A 110.2 . . ?
C23 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O2 C15 C17 108.63(9) . . ?
O2 C15 C14 105.41(9) . . ?
C17 C15 C14 111.48(9) . . ?
O2 C15 H15A 110.4 . . ?
C17 C15 H15A 110.4 . . ?
C14 C15 H15A 110.4 . . ?
O1 C16 O2 125.23(10) . . ?
O1 C16 C5 124.77(10) . . ?
O2 C16 C5 110.00(9) . . ?
C22 C17 C18 119.27(11) . . ?
C22 C17 C15 121.39(10) . . ?
C18 C17 C15 119.31(10) . . ?
C19 C18 C17 120.11(11) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C20 C19 C18 120.49(11) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C21 C20 C19 119.55(11) . . ?
C21 C20 H20A 120.2 . . ?
C19 C20 H20A 120.2 . . ?
C20 C21 C22 120.22(11) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C21 C22 C17 120.30(11) . . ?
C21 C22 H22A 119.9 . . ?
C17 C22 H22A 119.9 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
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
C6 C1 C2 C3 1.12(19) . . . . ?
C1 C2 C3 C4 0.72(19) . . . . ?
C2 C3 C4 C5 -2.49(18) . . . . ?
C3 C4 C5 C6 2.46(17) . . . . ?
C3 C4 C5 C16 -175.12(11) . . . . ?
C2 C1 C6 C5 -1.14(17) . . . . ?
C2 C1 C6 C7 177.13(11) . . . . ?
C4 C5 C6 C1 -0.64(16) . . . . ?
C16 C5 C6 C1 176.88(10) . . . . ?
C4 C5 C6 C7 -178.80(11) . . . . ?
C16 C5 C6 C7 -1.28(17) . . . . ?
C1 C6 C7 C8 -47.97(15) . . . . ?
C5 C6 C7 C8 130.18(12) . . . . ?
C1 C6 C7 C12 132.07(12) . . . . ?
C5 C6 C7 C12 -49.78(17) . . . . ?
C12 C7 C8 C9 0.24(17) . . . . ?
C6 C7 C8 C9 -179.72(11) . . . . ?
C7 C8 C9 C10 0.75(19) . . . . ?
C8 C9 C10 C11 -0.27(19) . . . . ?
C9 C10 C11 C12 -1.22(19) . . . . ?
C10 C11 C12 C7 2.25(18) . . . . ?
C10 C11 C12 C13 -176.96(11) . . . . ?
C8 C7 C12 C11 -1.72(16) . . . . ?
C6 C7 C12 C11 178.24(11) . . . . ?
C8 C7 C12 C13 177.46(10) . . . . ?
C6 C7 C12 C13 -2.58(17) . . . . ?
C14 O4 C13 O3 17.16(16) . . . . ?
C14 O4 C13 C12 -162.87(9) . . . . ?
C11 C12 C13 O3 118.53(13) . . . . ?
C7 C12 C13 O3 -60.67(16) . . . . ?
C11 C12 C13 O4 -61.44(13) . . . . ?
C7 C12 C13 O4 119.36(11) . . . . ?
C13 O4 C14 C23 -140.96(10) . . . . ?
C13 O4 C14 C15 97.71(11) . . . . ?
C16 O2 C15 C17 -146.61(10) . . . . ?
C16 O2 C15 C14 93.81(11) . . . . ?
O4 C14 C15 O2 -60.24(11) . . . . ?
C23 C14 C15 O2 -177.34(9) . . . . ?
O4 C14 C15 C17 -177.91(9) . . . . ?
C23 C14 C15 C17 64.98(13) . . . . ?
C15 O2 C16 O1 17.39(16) . . . . ?
C15 O2 C16 C5 -162.37(9) . . . . ?
C4 C5 C16 O1 119.47(13) . . . . ?
C6 C5 C16 O1 -58.11(16) . . . . ?
C4 C5 C16 O2 -60.77(13) . . . . ?
C6 C5 C16 O2 121.65(11) . . . . ?
O2 C15 C17 C22 -26.77(14) . . . . ?
C14 C15 C17 C22 88.95(13) . . . . ?
O2 C15 C17 C18 155.01(10) . . . . ?
C14 C15 C17 C18 -89.27(13) . . . . ?
C22 C17 C18 C19 -2.28(18) . . . . ?
C15 C17 C18 C19 175.98(11) . . . . ?
C17 C18 C19 C20 1.44(19) . . . . ?
C18 C19 C20 C21 0.67(19) . . . . ?
C19 C20 C21 C22 -1.92(19) . . . . ?
C20 C21 C22 C17 1.07(18) . . . . ?
C18 C17 C22 C21 1.03(17) . . . . ?
C15 C17 C22 C21 -177.19(11) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 33.82
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.619
_refine_diff_density_min -0.245
_refine_diff_density_rms 0.063
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
#
#D H A D - H H...A D...A D - H...A symm(A)
#
C15 H15A O1 1.0000 2.4500 3.3372(14) 147.00 3_667 yes
C23 H23A O3 0.9800 2.5500 3.1689(15) 121.00 4_565 yes
C23 H23B O1 0.9800 2.5300 3.4193(16) 151.00 3_667 yes
#==============================================================================
#End of cif