# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_cambridge 0177
#TrackingRef 'asc-is-fb204-fb232.cif'
#==============================================================================
_publ_contact_author_name 'Peter Langer'
_publ_contact_author_address
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
loop_
_publ_author_name
_publ_author_address
'Thomas Rahn'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
Leibniz-Institut f\"ur Katalyse an
der Universit\"at Rostock e.V.
Albert-Einstein-Strasse 29a
18059 Rostock
Bundesrepublik Deutschland
;
'Franziska Bendrath'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
'Wolfgang Baumann'
;
Leibniz-Institut f\"ur Katalyse an
der Universit\"at Rostock e.V.
Albert-Einstein-Strasse 29a
18059 Rostock
Bundesrepublik Deutschland
;
'Haijun Jiao'
;
Leibniz-Institut f\"ur Katalyse an
der Universit\"at Rostock e.V.
Albert-Einstein-Strasse 29a
18059 Rostock
Bundesrepublik Deutschland
;
'Armin B rner'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
Leibniz-Institut f\"ur Katalyse an
der Universit\"at Rostock e.V.
Albert-Einstein-Strasse 29a
18059 Rostock
Bundesrepublik Deutschland
;
'Alexander Villinger'
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Anorganische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
;
;
P.Langer
;
;
Universit\"at Rostock
Institut f\"ur Chemie
Abteilung f\"ur Organische Chemie
Albert-Einstein-Strasse 3a
18059 Rostock
Bundesrepublik Deutschland
Leibniz-Institut f\"ur Katalyse an
der Universit\"at Rostock e.V.
Albert-Einstein-Strasse 29a
18059 Rostock
Bundesrepublik Deutschland
;
_publ_contact_author_email peter.langer@uni-rostock.de
_publ_contact_author_fax '+49 (0)381/498-6410'
_publ_contact_author_phone '+49 (0)381/498-6412'
_publ_section_title
;
Synthesis and characterization of bis-cyclopropanated 1,3,5-tricarbonyl
compounds. A combined synthetic, spectroscopic and theoretical study
;
#=============================================================================
data_is_fb204
_database_code_depnum_ccdc_archive 'CCDC 818768'
#TrackingRef 'asc-is-fb204-fb232.cif'
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
Methyl 1-(3-(1-napththyl)-3-oxopropanoyl)cyclopropanecarboxylate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C18 H16 O4'
_chemical_formula_sum 'C18 H16 O4'
_chemical_formula_weight 296.31
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'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_Int_Tables_number 14
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 11.6786(3)
_cell_length_b 14.5262(4)
_cell_length_c 8.7114(2)
_cell_angle_alpha 90.00
_cell_angle_beta 103.8200(10)
_cell_angle_gamma 90.00
_cell_volume 1435.07(6)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 8944
_cell_measurement_theta_min 4.557
_cell_measurement_theta_max 62.055
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.44
_exptl_crystal_size_mid 0.42
_exptl_crystal_size_min 0.34
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.371
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 624
_exptl_absorpt_coefficient_mu 0.097
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9587
_exptl_absorpt_correction_T_max 0.9679
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 17162
_diffrn_reflns_av_R_equivalents 0.0157
_diffrn_reflns_av_sigmaI/netI 0.0143
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.28
_diffrn_reflns_theta_max 30.50
_reflns_number_total 4371
_reflns_number_gt 3718
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms (with exception of H1a) were positioned geometrically
and refined using a riding model , with C---H = 0.98 (methyl groups),
0.99\%A (methylene groups), 1.00\%A (methine groups) or 0.95 \%A (aryl CH)
and with U~iso~(H) = 1.5 times U~eq~(C) (methyl groups) or
with U~iso~(H) = 1.2 times U~eq~(C) (methylene groups,
aryl CH, methine groups). Torsion angles of all methyl groups were allowed
to refine.
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^ > 2\s(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^)+(0.0805P)^2^+0.2290P] 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 4371
_refine_ls_number_parameters 204
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0509
_refine_ls_R_factor_gt 0.0434
_refine_ls_wR_factor_ref 0.1322
_refine_ls_wR_factor_gt 0.1267
_refine_ls_goodness_of_fit_ref 1.058
_refine_ls_restrained_S_all 1.058
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 0.11402(7) 0.98131(5) 0.91445(11) 0.03638(19) Uani 1 1 d . . .
O2 O 0.00869(7) 0.83892(5) 0.94962(12) 0.0395(2) Uani 1 1 d . . .
O3 O 0.14032(7) 0.53839(5) 0.89323(12) 0.0393(2) Uani 1 1 d . . .
O4 O 0.26634(8) 0.64848(6) 0.86772(15) 0.0519(3) Uani 1 1 d . . .
H1A H 0.045(2) 0.9181(16) 0.938(3) 0.085(7) Uiso 1 1 d . . .
C1 C 0.30204(8) 0.97931(6) 0.84828(11) 0.02389(18) Uani 1 1 d . . .
C2 C 0.36498(9) 0.92964(7) 0.76001(12) 0.0290(2) Uani 1 1 d . . .
H2 H 0.3398 0.8691 0.7268 0.035 Uiso 1 1 calc R . .
C3 C 0.46493(10) 0.96609(7) 0.71807(13) 0.0329(2) Uani 1 1 d . . .
H3 H 0.5056 0.9307 0.6563 0.039 Uiso 1 1 calc R . .
C4 C 0.50335(9) 1.05261(7) 0.76648(13) 0.0304(2) Uani 1 1 d . . .
H4 H 0.5717 1.0767 0.7399 0.036 Uiso 1 1 calc R . .
C5 C 0.44195(8) 1.10659(6) 0.85603(11) 0.02466(18) Uani 1 1 d . . .
C6 C 0.33877(8) 1.07172(6) 0.89689(10) 0.02279(18) Uani 1 1 d . . .
C7 C 0.28139(9) 1.12963(7) 0.98718(12) 0.0280(2) Uani 1 1 d . . .
H7 H 0.2120 1.1086 1.0149 0.034 Uiso 1 1 calc R . .
C8 C 0.32504(10) 1.21542(7) 1.03471(13) 0.0336(2) Uani 1 1 d . . .
H8 H 0.2855 1.2527 1.0954 0.040 Uiso 1 1 calc R . .
C9 C 0.42738(10) 1.24924(7) 0.99509(13) 0.0345(2) Uani 1 1 d . . .
H9 H 0.4568 1.3086 1.0294 0.041 Uiso 1 1 calc R . .
C10 C 0.48401(9) 1.19603(7) 0.90692(12) 0.0307(2) Uani 1 1 d . . .
H10 H 0.5525 1.2191 0.8792 0.037 Uiso 1 1 calc R . .
C11 C 0.20031(8) 0.93266(7) 0.89071(11) 0.02598(19) Uani 1 1 d . . .
C12 C 0.19750(8) 0.83546(6) 0.90021(12) 0.02680(19) Uani 1 1 d . . .
H12 H 0.2638 0.8002 0.8897 0.032 Uiso 1 1 calc R . .
C13 C 0.09740(8) 0.79153(7) 0.92497(11) 0.02631(19) Uani 1 1 d . . .
C14 C 0.07946(8) 0.68972(6) 0.92044(11) 0.02421(18) Uani 1 1 d . . .
C15 C 0.00015(9) 0.65311(7) 1.02398(13) 0.0311(2) Uani 1 1 d . . .
H15A H 0.0177 0.5911 1.0708 0.037 Uiso 1 1 calc R . .
H15B H -0.0288 0.6978 1.0917 0.037 Uiso 1 1 calc R . .
C16 C -0.04908(9) 0.65895(7) 0.85148(13) 0.0314(2) Uani 1 1 d . . .
H16A H -0.1084 0.7074 0.8120 0.038 Uiso 1 1 calc R . .
H16B H -0.0619 0.6006 0.7911 0.038 Uiso 1 1 calc R . .
C17 C 0.17257(9) 0.62658(7) 0.89051(12) 0.0272(2) Uani 1 1 d . . .
C18 C 0.22222(11) 0.47120(8) 0.86116(18) 0.0430(3) Uani 1 1 d . . .
H18A H 0.2398 0.4847 0.7589 0.064 Uiso 1 1 calc R . .
H18B H 0.1874 0.4096 0.8581 0.064 Uiso 1 1 calc R . .
H18C H 0.2952 0.4735 0.9446 0.064 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 0.0285(4) 0.0240(3) 0.0603(5) 0.0020(3) 0.0178(3) 0.0014(3)
O2 0.0316(4) 0.0263(4) 0.0671(6) -0.0019(3) 0.0246(4) -0.0002(3)
O3 0.0321(4) 0.0215(3) 0.0703(6) -0.0022(3) 0.0243(4) -0.0029(3)
O4 0.0421(5) 0.0262(4) 0.1015(8) -0.0043(4) 0.0453(5) -0.0043(3)
C1 0.0229(4) 0.0215(4) 0.0266(4) 0.0031(3) 0.0047(3) -0.0011(3)
C2 0.0323(5) 0.0223(4) 0.0337(5) 0.0002(3) 0.0106(4) -0.0013(3)
C3 0.0348(5) 0.0300(5) 0.0385(5) 0.0004(4) 0.0180(4) 0.0020(4)
C4 0.0269(5) 0.0300(5) 0.0367(5) 0.0055(4) 0.0123(4) -0.0004(4)
C5 0.0227(4) 0.0239(4) 0.0263(4) 0.0049(3) 0.0040(3) -0.0009(3)
C6 0.0215(4) 0.0215(4) 0.0245(4) 0.0038(3) 0.0038(3) 0.0002(3)
C7 0.0278(4) 0.0259(4) 0.0307(4) 0.0004(3) 0.0080(3) 0.0010(3)
C8 0.0384(5) 0.0273(5) 0.0351(5) -0.0033(4) 0.0089(4) 0.0002(4)
C9 0.0411(6) 0.0252(4) 0.0352(5) -0.0013(4) 0.0051(4) -0.0060(4)
C10 0.0302(5) 0.0272(5) 0.0336(5) 0.0038(4) 0.0053(4) -0.0064(4)
C11 0.0229(4) 0.0238(4) 0.0305(4) 0.0021(3) 0.0050(3) -0.0009(3)
C12 0.0232(4) 0.0214(4) 0.0360(5) 0.0021(3) 0.0075(3) -0.0009(3)
C13 0.0242(4) 0.0242(4) 0.0314(4) 0.0006(3) 0.0083(3) -0.0007(3)
C14 0.0224(4) 0.0232(4) 0.0285(4) 0.0000(3) 0.0090(3) -0.0034(3)
C15 0.0328(5) 0.0304(5) 0.0347(5) -0.0001(4) 0.0172(4) -0.0063(4)
C16 0.0228(4) 0.0328(5) 0.0386(5) -0.0045(4) 0.0076(4) -0.0047(4)
C17 0.0276(4) 0.0226(4) 0.0339(5) -0.0001(3) 0.0119(4) -0.0026(3)
C18 0.0376(6) 0.0239(5) 0.0729(9) -0.0080(5) 0.0239(6) -0.0008(4)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 1.2873(12) . ?
O1 H1A 1.27(2) . ?
O2 C13 1.3037(12) . ?
O2 H1A 1.24(2) . ?
O3 C17 1.3370(12) . ?
O3 C18 1.4399(13) . ?
O4 C17 1.2015(12) . ?
C1 C2 1.3864(13) . ?
C1 C6 1.4416(13) . ?
C1 C11 1.4890(13) . ?
C2 C3 1.4072(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3668(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.4158(14) . ?
C4 H4 0.9500 . ?
C5 C10 1.4220(14) . ?
C5 C6 1.4284(12) . ?
C6 C7 1.4238(13) . ?
C7 C8 1.3724(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.4093(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3665(16) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.4153(13) . ?
C12 C13 1.3932(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.4929(13) . ?
C14 C17 1.4923(13) . ?
C14 C15 1.5341(12) . ?
C14 C16 1.5439(13) . ?
C15 C16 1.4775(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C11 O1 H1A 100.3(11) . . ?
C13 O2 H1A 100.0(11) . . ?
C17 O3 C18 116.30(8) . . ?
C2 C1 C6 119.17(8) . . ?
C2 C1 C11 117.45(8) . . ?
C6 C1 C11 123.36(8) . . ?
C1 C2 C3 122.06(9) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 119.82(9) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.47(9) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C10 119.68(9) . . ?
C4 C5 C6 120.61(9) . . ?
C10 C5 C6 119.70(9) . . ?
C7 C6 C5 117.68(8) . . ?
C7 C6 C1 124.48(8) . . ?
C5 C6 C1 117.81(8) . . ?
C8 C7 C6 120.88(9) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 121.22(10) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C10 C9 C8 119.54(10) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C5 120.97(9) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
O1 C11 C12 120.55(9) . . ?
O1 C11 C1 119.46(8) . . ?
C12 C11 C1 119.97(8) . . ?
C13 C12 C11 119.87(9) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O2 C13 C12 120.85(9) . . ?
O2 C13 C14 114.55(8) . . ?
C12 C13 C14 124.56(8) . . ?
C17 C14 C13 120.66(8) . . ?
C17 C14 C15 117.21(8) . . ?
C13 C14 C15 115.37(8) . . ?
C17 C14 C16 115.82(8) . . ?
C13 C14 C16 114.48(8) . . ?
C15 C14 C16 57.37(7) . . ?
C16 C15 C14 61.64(6) . . ?
C16 C15 H15A 117.6 . . ?
C14 C15 H15A 117.6 . . ?
C16 C15 H15B 117.6 . . ?
C14 C15 H15B 117.6 . . ?
H15A C15 H15B 114.7 . . ?
C15 C16 C14 60.98(6) . . ?
C15 C16 H16A 117.7 . . ?
C14 C16 H16A 117.7 . . ?
C15 C16 H16B 117.7 . . ?
C14 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
O4 C17 O3 121.89(9) . . ?
O4 C17 C14 126.66(9) . . ?
O3 C17 C14 111.45(8) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 0.94(15) . . . . ?
C11 C1 C2 C3 -177.85(9) . . . . ?
C1 C2 C3 C4 0.85(17) . . . . ?
C2 C3 C4 C5 -1.23(17) . . . . ?
C3 C4 C5 C10 179.27(10) . . . . ?
C3 C4 C5 C6 -0.17(15) . . . . ?
C4 C5 C6 C7 179.97(9) . . . . ?
C10 C5 C6 C7 0.53(13) . . . . ?
C4 C5 C6 C1 1.91(13) . . . . ?
C10 C5 C6 C1 -177.54(8) . . . . ?
C2 C1 C6 C7 179.82(9) . . . . ?
C11 C1 C6 C7 -1.47(14) . . . . ?
C2 C1 C6 C5 -2.26(13) . . . . ?
C11 C1 C6 C5 176.45(8) . . . . ?
C5 C6 C7 C8 -0.84(14) . . . . ?
C1 C6 C7 C8 177.09(9) . . . . ?
C6 C7 C8 C9 0.40(16) . . . . ?
C7 C8 C9 C10 0.40(17) . . . . ?
C8 C9 C10 C5 -0.71(16) . . . . ?
C4 C5 C10 C9 -179.21(10) . . . . ?
C6 C5 C10 C9 0.24(15) . . . . ?
C2 C1 C11 O1 -152.79(10) . . . . ?
C6 C1 C11 O1 28.48(14) . . . . ?
C2 C1 C11 C12 25.41(14) . . . . ?
C6 C1 C11 C12 -153.32(9) . . . . ?
O1 C11 C12 C13 4.31(15) . . . . ?
C1 C11 C12 C13 -173.87(9) . . . . ?
C11 C12 C13 O2 -4.39(15) . . . . ?
C11 C12 C13 C14 173.38(9) . . . . ?
O2 C13 C14 C17 178.96(9) . . . . ?
C12 C13 C14 C17 1.07(15) . . . . ?
O2 C13 C14 C15 -30.66(13) . . . . ?
C12 C13 C14 C15 151.45(10) . . . . ?
O2 C13 C14 C16 33.25(12) . . . . ?
C12 C13 C14 C16 -144.64(10) . . . . ?
C17 C14 C15 C16 -104.62(10) . . . . ?
C13 C14 C15 C16 103.94(9) . . . . ?
C17 C14 C16 C15 107.06(9) . . . . ?
C13 C14 C16 C15 -105.51(9) . . . . ?
C18 O3 C17 O4 -2.37(18) . . . . ?
C18 O3 C17 C14 178.26(10) . . . . ?
C13 C14 C17 O4 -0.17(17) . . . . ?
C15 C14 C17 O4 -150.03(12) . . . . ?
C16 C14 C17 O4 145.10(12) . . . . ?
C13 C14 C17 O3 179.16(9) . . . . ?
C15 C14 C17 O3 29.30(13) . . . . ?
C16 C14 C17 O3 -35.57(12) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 30.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.462
_refine_diff_density_min -0.264
_refine_diff_density_rms 0.047
#=============================================================================
data_is_fb232
_database_code_depnum_ccdc_archive 'CCDC 818769'
#TrackingRef 'asc-is-fb204-fb232.cif'
_audit_author_name 'Villinger, A.'
_audit_creation_method SHELXL-97
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic
;
Methyl 1-(1-(4-methoxybenzoyl)cyclopropanecarbonyl)cyclopropanecarboxylate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H18 O5'
_chemical_formula_sum 'C17 H18 O5'
_chemical_formula_weight 302.31
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'
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_Int_Tables_number 14
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 9.4464(3)
_cell_length_b 8.3079(3)
_cell_length_c 19.3443(7)
_cell_angle_alpha 90.00
_cell_angle_beta 94.272(2)
_cell_angle_gamma 90.00
_cell_volume 1513.92(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 6195
_cell_measurement_theta_min 5.338
_cell_measurement_theta_max 59.647
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.67
_exptl_crystal_size_mid 0.34
_exptl_crystal_size_min 0.12
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.326
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 0.098
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9375
_exptl_absorpt_correction_T_max 0.9884
_exptl_absorpt_process_details '(SADABS; Sheldrick, 2004)'
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method 'phi and psi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 16474
_diffrn_reflns_av_R_equivalents 0.0270
_diffrn_reflns_av_sigmaI/netI 0.0262
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_theta_min 2.67
_diffrn_reflns_theta_max 29.93
_reflns_number_total 4364
_reflns_number_gt 3408
_reflns_threshold_expression >2\s(I)
_computing_data_collection 'Bruker Apex v2.0-2'
_computing_cell_refinement 'Bruker Apex v2.0-2'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material SHELXL-97
#==============================================================================
# REFINEMENT DATA
_refine_special_details
;
All H atoms were positioned geometrically and refined using a
riding model , with C---H = 0.98 (methyl groups), 0.99\%A (methylene groups),
1.00\%A (methine groups) or 0.95 \%A (aryl CH) and with U~iso~(H) =
1.5 times U~eq~(C) (methyl groups) or with U~iso~(H) = 1.2 times
U~eq~(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.
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^ > 2\s(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^)+(0.0584P)^2^+0.2365P] 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 4364
_refine_ls_number_parameters 201
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0560
_refine_ls_R_factor_gt 0.0416
_refine_ls_wR_factor_ref 0.1133
_refine_ls_wR_factor_gt 0.1063
_refine_ls_goodness_of_fit_ref 1.033
_refine_ls_restrained_S_all 1.033
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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 -0.01875(10) 0.34596(11) 0.45301(5) 0.0408(2) Uani 1 1 d . . .
O2 O 0.11703(9) -0.32165(10) 0.31002(5) 0.0372(2) Uani 1 1 d . . .
O3 O 0.56390(9) -0.21190(10) 0.42645(4) 0.0337(2) Uani 1 1 d . . .
O4 O 0.33160(9) -0.08480(9) 0.24765(4) 0.03081(18) Uani 1 1 d . . .
O5 O 0.33991(8) 0.17612(9) 0.27926(4) 0.03021(19) Uani 1 1 d . . .
C1 C 0.13496(11) -0.08270(13) 0.37693(5) 0.0247(2) Uani 1 1 d . . .
C2 C 0.03434(11) 0.00558(13) 0.33596(6) 0.0264(2) Uani 1 1 d . . .
H2 H 0.0015 -0.0344 0.2916 0.032 Uiso 1 1 calc R . .
C3 C -0.01844(11) 0.15060(13) 0.35884(6) 0.0274(2) Uani 1 1 d . . .
H3 H -0.0848 0.2107 0.3300 0.033 Uiso 1 1 calc R . .
C4 C 0.02714(12) 0.20709(14) 0.42477(6) 0.0290(2) Uani 1 1 d . . .
C5 C 0.12714(13) 0.11947(15) 0.46673(6) 0.0330(3) Uani 1 1 d . . .
H5 H 0.1582 0.1582 0.5115 0.040 Uiso 1 1 calc R . .
C6 C 0.18042(12) -0.02321(14) 0.44278(6) 0.0291(2) Uani 1 1 d . . .
H6 H 0.2487 -0.0818 0.4712 0.035 Uiso 1 1 calc R . .
C7 C -0.11542(15) 0.44397(16) 0.41055(7) 0.0429(3) Uani 1 1 d . . .
H7A H -0.0716 0.4738 0.3680 0.064 Uiso 1 1 calc R . .
H7B H -0.1378 0.5415 0.4360 0.064 Uiso 1 1 calc R . .
H7C H -0.2029 0.3835 0.3986 0.064 Uiso 1 1 calc R . .
C8 C 0.19075(11) -0.23572(13) 0.34970(5) 0.0260(2) Uani 1 1 d . . .
C9 C 0.33802(11) -0.28711(12) 0.37614(5) 0.0247(2) Uani 1 1 d . . .
C10 C 0.38190(15) -0.45707(14) 0.35737(7) 0.0404(3) Uani 1 1 d . . .
H10A H 0.3167 -0.5187 0.3248 0.048 Uiso 1 1 calc R . .
H10B H 0.4840 -0.4773 0.3527 0.048 Uiso 1 1 calc R . .
C11 C 0.33648(15) -0.42702(15) 0.42784(7) 0.0401(3) Uani 1 1 d . . .
H11A H 0.4104 -0.4282 0.4669 0.048 Uiso 1 1 calc R . .
H11B H 0.2430 -0.4696 0.4390 0.048 Uiso 1 1 calc R . .
C12 C 0.46086(11) -0.17250(12) 0.38779(5) 0.0239(2) Uani 1 1 d . . .
C13 C 0.46036(11) -0.00904(12) 0.35399(5) 0.0234(2) Uani 1 1 d . . .
C14 C 0.49008(13) 0.13012(13) 0.40491(6) 0.0328(3) Uani 1 1 d . . .
H14A H 0.4399 0.2331 0.3948 0.039 Uiso 1 1 calc R . .
H14B H 0.5053 0.1034 0.4548 0.039 Uiso 1 1 calc R . .
C15 C 0.60191(12) 0.08328(14) 0.35939(7) 0.0343(3) Uani 1 1 d . . .
H15A H 0.6865 0.0272 0.3809 0.041 Uiso 1 1 calc R . .
H15B H 0.6211 0.1569 0.3210 0.041 Uiso 1 1 calc R . .
C16 C 0.36983(11) 0.01935(12) 0.28866(5) 0.0228(2) Uani 1 1 d . . .
C17 C 0.25118(13) 0.21690(14) 0.21763(6) 0.0340(3) Uani 1 1 d . . .
H17A H 0.2919 0.1708 0.1769 0.051 Uiso 1 1 calc R . .
H17B H 0.2459 0.3342 0.2128 0.051 Uiso 1 1 calc R . .
H17C H 0.1556 0.1734 0.2214 0.051 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 0.0486(5) 0.0371(5) 0.0351(5) -0.0052(4) -0.0083(4) 0.0159(4)
O2 0.0377(5) 0.0320(4) 0.0403(5) -0.0041(3) -0.0087(4) -0.0089(3)
O3 0.0308(4) 0.0313(4) 0.0372(4) 0.0026(3) -0.0089(3) 0.0036(3)
O4 0.0404(4) 0.0264(4) 0.0251(4) -0.0026(3) -0.0009(3) -0.0020(3)
O5 0.0317(4) 0.0216(4) 0.0358(4) 0.0031(3) -0.0075(3) 0.0002(3)
C1 0.0212(5) 0.0269(5) 0.0259(5) 0.0009(4) 0.0006(4) -0.0032(4)
C2 0.0222(5) 0.0308(5) 0.0258(5) 0.0000(4) -0.0018(4) -0.0040(4)
C3 0.0219(5) 0.0313(5) 0.0283(5) 0.0034(4) -0.0023(4) -0.0002(4)
C4 0.0281(5) 0.0299(6) 0.0288(5) 0.0005(4) 0.0009(4) 0.0030(4)
C5 0.0358(6) 0.0384(6) 0.0238(5) -0.0031(4) -0.0046(4) 0.0067(5)
C6 0.0271(5) 0.0341(6) 0.0254(5) 0.0016(4) -0.0022(4) 0.0047(4)
C7 0.0475(8) 0.0351(7) 0.0445(7) -0.0012(5) -0.0077(6) 0.0143(6)
C8 0.0280(5) 0.0239(5) 0.0258(5) 0.0026(4) -0.0003(4) -0.0046(4)
C9 0.0281(5) 0.0183(4) 0.0274(5) 0.0007(4) -0.0001(4) -0.0002(4)
C10 0.0445(7) 0.0189(5) 0.0577(8) -0.0051(5) 0.0031(6) 0.0011(5)
C11 0.0403(7) 0.0314(6) 0.0484(7) 0.0170(5) 0.0010(6) -0.0011(5)
C12 0.0259(5) 0.0216(5) 0.0238(5) -0.0025(4) -0.0001(4) 0.0026(4)
C13 0.0228(5) 0.0202(5) 0.0266(5) -0.0010(4) -0.0011(4) -0.0015(4)
C14 0.0430(7) 0.0227(5) 0.0313(6) -0.0046(4) -0.0068(5) -0.0032(5)
C15 0.0278(6) 0.0311(6) 0.0428(7) 0.0029(5) -0.0053(5) -0.0090(4)
C16 0.0219(5) 0.0216(5) 0.0251(5) 0.0009(4) 0.0024(4) -0.0014(4)
C17 0.0343(6) 0.0307(6) 0.0356(6) 0.0092(5) -0.0068(5) 0.0005(5)
#==============================================================================
# MOLECULAR GEOMETRY
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C4 1.3612(14) . ?
O1 C7 1.4352(14) . ?
O2 C8 1.2264(13) . ?
O3 C12 1.2270(12) . ?
O4 C16 1.2107(12) . ?
O5 C16 1.3422(12) . ?
O5 C17 1.4455(13) . ?
C1 C2 1.3990(14) . ?
C1 C6 1.4035(15) . ?
C1 C8 1.4875(15) . ?
C2 C3 1.3889(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3965(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.4025(15) . ?
C5 C6 1.3813(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5078(15) . ?
C9 C12 1.5050(14) . ?
C9 C10 1.5231(15) . ?
C9 C11 1.5341(15) . ?
C10 C11 1.480(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5070(14) . ?
C13 C16 1.4911(14) . ?
C13 C14 1.5311(14) . ?
C13 C15 1.5383(15) . ?
C14 C15 1.4769(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C4 O1 C7 117.33(9) . . ?
C16 O5 C17 116.26(9) . . ?
C2 C1 C6 118.59(10) . . ?
C2 C1 C8 119.41(9) . . ?
C6 C1 C8 122.00(9) . . ?
C3 C2 C1 121.28(10) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.27(10) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
O1 C4 C3 124.45(10) . . ?
O1 C4 C5 115.37(10) . . ?
C3 C4 C5 120.18(10) . . ?
C6 C5 C4 119.85(10) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.81(10) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C1 121.30(10) . . ?
O2 C8 C9 120.93(10) . . ?
C1 C8 C9 117.66(9) . . ?
C12 C9 C8 123.59(9) . . ?
C12 C9 C10 113.69(9) . . ?
C8 C9 C10 116.25(9) . . ?
C12 C9 C11 115.24(9) . . ?
C8 C9 C11 112.48(9) . . ?
C10 C9 C11 57.93(8) . . ?
C11 C10 C9 61.41(8) . . ?
C11 C10 H10A 117.6 . . ?
C9 C10 H10A 117.6 . . ?
C11 C10 H10B 117.6 . . ?
C9 C10 H10B 117.6 . . ?
H10A C10 H10B 114.7 . . ?
C10 C11 C9 60.66(8) . . ?
C10 C11 H11A 117.7 . . ?
C9 C11 H11A 117.7 . . ?
C10 C11 H11B 117.7 . . ?
C9 C11 H11B 117.7 . . ?
H11A C11 H11B 114.8 . . ?
O3 C12 C9 119.36(9) . . ?
O3 C12 C13 118.78(9) . . ?
C9 C12 C13 121.86(9) . . ?
C16 C13 C12 119.56(8) . . ?
C16 C13 C14 119.47(9) . . ?
C12 C13 C14 114.01(9) . . ?
C16 C13 C15 114.80(9) . . ?
C12 C13 C15 116.44(9) . . ?
C14 C13 C15 57.52(8) . . ?
C15 C14 C13 61.48(7) . . ?
C15 C14 H14A 117.6 . . ?
C13 C14 H14A 117.6 . . ?
C15 C14 H14B 117.6 . . ?
C13 C14 H14B 117.6 . . ?
H14A C14 H14B 114.7 . . ?
C14 C15 C13 61.00(7) . . ?
C14 C15 H15A 117.7 . . ?
C13 C15 H15A 117.7 . . ?
C14 C15 H15B 117.7 . . ?
C13 C15 H15B 117.7 . . ?
H15A C15 H15B 114.8 . . ?
O4 C16 O5 123.73(10) . . ?
O4 C16 C13 124.51(9) . . ?
O5 C16 C13 111.72(8) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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(16) . . . . ?
C8 C1 C2 C3 -178.73(10) . . . . ?
C1 C2 C3 C4 -1.70(16) . . . . ?
C7 O1 C4 C3 -3.07(17) . . . . ?
C7 O1 C4 C5 176.77(11) . . . . ?
C2 C3 C4 O1 -178.98(11) . . . . ?
C2 C3 C4 C5 1.19(17) . . . . ?
O1 C4 C5 C6 -179.96(11) . . . . ?
C3 C4 C5 C6 -0.12(18) . . . . ?
C4 C5 C6 C1 -0.47(18) . . . . ?
C2 C1 C6 C5 -0.02(17) . . . . ?
C8 C1 C6 C5 179.83(10) . . . . ?
C2 C1 C8 O2 -31.51(15) . . . . ?
C6 C1 C8 O2 148.64(11) . . . . ?
C2 C1 C8 C9 152.35(10) . . . . ?
C6 C1 C8 C9 -27.50(15) . . . . ?
O2 C8 C9 C12 143.33(11) . . . . ?
C1 C8 C9 C12 -40.51(14) . . . . ?
O2 C8 C9 C10 -6.58(15) . . . . ?
C1 C8 C9 C10 169.58(10) . . . . ?
O2 C8 C9 C11 -70.68(14) . . . . ?
C1 C8 C9 C11 105.47(11) . . . . ?
C12 C9 C10 C11 105.94(11) . . . . ?
C8 C9 C10 C11 -101.20(11) . . . . ?
C12 C9 C11 C10 -103.22(11) . . . . ?
C8 C9 C11 C10 107.79(11) . . . . ?
C8 C9 C12 O3 159.75(10) . . . . ?
C10 C9 C12 O3 -49.66(14) . . . . ?
C11 C9 C12 O3 14.60(15) . . . . ?
C8 C9 C12 C13 -19.42(15) . . . . ?
C10 C9 C12 C13 131.17(11) . . . . ?
C11 C9 C12 C13 -164.56(10) . . . . ?
O3 C12 C13 C16 156.69(10) . . . . ?
C9 C12 C13 C16 -24.14(14) . . . . ?
O3 C12 C13 C14 -52.65(14) . . . . ?
C9 C12 C13 C14 126.52(10) . . . . ?
O3 C12 C13 C15 11.56(14) . . . . ?
C9 C12 C13 C15 -169.27(10) . . . . ?
C16 C13 C14 C15 -102.20(11) . . . . ?
C12 C13 C14 C15 107.11(10) . . . . ?
C16 C13 C15 C14 110.38(10) . . . . ?
C12 C13 C15 C14 -102.84(10) . . . . ?
C17 O5 C16 O4 3.00(15) . . . . ?
C17 O5 C16 C13 -179.36(9) . . . . ?
C12 C13 C16 O4 -25.28(15) . . . . ?
C14 C13 C16 O4 -174.34(10) . . . . ?
C15 C13 C16 O4 120.40(12) . . . . ?
C12 C13 C16 O5 157.10(9) . . . . ?
C14 C13 C16 O5 8.04(13) . . . . ?
C15 C13 C16 O5 -57.22(12) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 29.93
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.271
_refine_diff_density_min -0.264
_refine_diff_density_rms 0.060
#===================== End of CIF submission =================================