# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full Org.Biomol.Chem.
_journal_coden_Cambridge 0177
#TrackingRef 'OBC-Synthesis-of-piperitone-derived-halogenated-lactones.cif.cif'
_audit_creation_method SHELXL-97
_publ_contact_author_name 'Czeslaw Wawrzenczyk'
_publ_contact_author_address
;
Czes\/law Wawrze\'nczyk
Department of Chemistry
Wroclaw University of Environmental and Life Sciences
Norwida 25
50-375 Wroc\/law
Poland
;
_publ_contact_author_email czeslaw.wawrzenczyk@up.wroc.pl
_publ_requested_category ?
_publ_requested_coeditor_name ?
_journal_date_recd_electronic ?
_journal_date_to_coeditor ?
_journal_date_from_coeditor ?
_journal_date_accepted ?
_journal_date_printers_first ?
_journal_date_printers_final ?
_journal_date_proofs_out ?
_journal_date_proofs_in ?
_journal_coeditor_name ?
_journal_coeditor_code ?
_journal_coeditor_notes
; ?
;
_journal_techeditor_code ?
_journal_techeditor_notes
; ?
;
_journal_coden_ASTM ?
_journal_year ?
_journal_volume ?
_journal_issue ?
_journal_page_first ?
_journal_page_last ?
_journal_suppl_publ_number ?
_journal_suppl_publ_pages ?
_publ_section_title
;
Synthesis of piperitone-derived halogenated lactones
and their effect on aphid probing, feeding,
and settling behavior
;
loop_
_publ_author_name
_publ_author_address
'Aleksandra Grudniewska'
;
Department of Chemistry
Wroclaw University of Environmental and Life Sciences
Norwida 25
50-375 Wroc\/law
Poland
;
'Katarzyna Dancewicz'
;
Department of Biology and Ecology
University of Zielona G\'ora
Szafrana 1
5-516 Zielona G\'ora
Poland
;
A.Bialonska
;
Faculty of Chemistry
University of Wroc\/law
F. Joliot-Curie 14
50-383 Wroc\/law
Poland
;
'Zbigniew Ciunik'
;
Faculty of Chemistry
University of Wroc\/law
F. Joliot-Curie 14
50-383 Wroc\/law
Poland
;
B.Gabrys
;
Department of Biology and Ecology
University of Zielona G\'ora
Szafrana 1
5-516 Zielona G\'ora
Poland
;
;
C.Wawrzenczyk
;
;
Department of Chemistry
Wroclaw University of Environmental and Life Sciences
Norwida 25
50-375 Wroc\/law
Poland
;
data_(+)-4a
_database_code_depnum_ccdc_archive 'CCDC 825643'
#TrackingRef 'OBC-Synthesis-of-piperitone-derived-halogenated-lactones.cif.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(+)-(1S,4R,5R,6R)-5-iodo-4-isopropyl
-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H19 I O2'
_chemical_formula_sum 'C12 H19 I O2'
_chemical_formula_weight 322.17
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 8.140(2)
_cell_length_b 8.211(2)
_cell_length_c 18.950(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1266.6(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 8347
_cell_measurement_theta_min 3.22
_cell_measurement_theta_max 28.67
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.21
_exptl_crystal_size_min 0.18
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.690
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 2.509
_exptl_absorpt_correction_T_min 0.603
_exptl_absorpt_correction_T_max 0.713
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8427
_diffrn_reflns_av_R_equivalents 0.0279
_diffrn_reflns_av_sigmaI/netI 0.0180
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 3.28
_diffrn_reflns_theta_max 26.99
_reflns_number_total 2764
_reflns_number_gt 2716
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0242P)^2^+0.4203P] 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 ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.003(17)
_refine_ls_number_reflns 2764
_refine_ls_number_parameters 136
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0171
_refine_ls_R_factor_gt 0.0166
_refine_ls_wR_factor_ref 0.0420
_refine_ls_wR_factor_gt 0.0419
_refine_ls_goodness_of_fit_ref 1.089
_refine_ls_restrained_S_all 1.089
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
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
I I 0.428415(17) 0.474231(17) 0.863748(8) 0.02368(5) Uani 1 1 d . . .
C1 C 0.3996(2) -0.0198(3) 0.96527(9) 0.0129(3) Uani 1 1 d . . .
C2 C 0.2298(2) -0.0759(3) 0.94002(10) 0.0142(4) Uani 1 1 d . . .
H2E H 0.2270 -0.1964 0.9398 0.017 Uiso 1 1 calc R . .
H2A H 0.1461 -0.0377 0.9741 0.017 Uiso 1 1 calc R . .
C3 C 0.1842(2) -0.0144(2) 0.86682(11) 0.0142(3) Uani 1 1 d . . .
H3E H 0.0717 -0.0510 0.8548 0.017 Uiso 1 1 calc R . .
H3A H 0.2608 -0.0607 0.8315 0.017 Uiso 1 1 calc R . .
C4 C 0.1921(2) 0.1738(2) 0.86405(12) 0.0135(3) Uani 1 1 d . . .
H4A H 0.1297 0.2163 0.9056 0.016 Uiso 1 1 calc R . .
C5 C 0.3737(2) 0.2152(2) 0.87547(10) 0.0142(4) Uani 1 1 d . . .
H5A H 0.4390 0.1547 0.8393 0.017 Uiso 1 1 calc R . .
C6 C 0.4343(3) 0.1621(2) 0.94831(10) 0.0143(4) Uani 1 1 d . . .
H6A H 0.3856 0.2333 0.9857 0.017 Uiso 1 1 calc R . .
O7 O 0.61405(17) 0.17266(19) 0.95017(8) 0.0163(3) Uani 1 1 d . . .
C8 C 0.6808(2) 0.0228(3) 0.93831(10) 0.0164(4) Uani 1 1 d . . .
O8 O 0.82692(16) 0.0030(2) 0.93803(8) 0.0223(4) Uani 1 1 d . . .
C9 C 0.5462(2) -0.1006(3) 0.92845(10) 0.0153(4) Uani 1 1 d . . .
H9A H 0.5747 -0.2056 0.9510 0.018 Uiso 1 1 calc R . .
H9B H 0.5234 -0.1193 0.8778 0.018 Uiso 1 1 calc R . .
C10 C 0.4141(3) -0.0477(3) 1.04521(10) 0.0184(4) Uani 1 1 d . . .
H10A H 0.3934 -0.1626 1.0559 0.028 Uiso 1 1 calc R . .
H10B H 0.3332 0.0201 1.0698 0.028 Uiso 1 1 calc R . .
H10C H 0.5248 -0.0182 1.0609 0.028 Uiso 1 1 calc R . .
C11 C 0.1137(3) 0.2474(3) 0.79722(10) 0.0165(4) Uani 1 1 d . . .
H11A H 0.1237 0.3684 0.8013 0.020 Uiso 1 1 calc R . .
C12 C -0.0701(3) 0.2083(3) 0.79292(11) 0.0217(4) Uani 1 1 d . . .
H12A H -0.1240 0.2413 0.8369 0.033 Uiso 1 1 calc R . .
H12B H -0.0849 0.0909 0.7859 0.033 Uiso 1 1 calc R . .
H12C H -0.1190 0.2675 0.7532 0.033 Uiso 1 1 calc R . .
C13 C 0.2009(3) 0.1978(3) 0.72904(12) 0.0260(5) Uani 1 1 d . . .
H13A H 0.3182 0.2232 0.7329 0.039 Uiso 1 1 calc R . .
H13B H 0.1535 0.2578 0.6893 0.039 Uiso 1 1 calc R . .
H13C H 0.1869 0.0806 0.7213 0.039 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
I 0.02410(7) 0.01369(7) 0.03326(8) 0.00516(5) -0.00400(6) -0.00520(5)
C1 0.0113(8) 0.0125(9) 0.0149(8) 0.0006(7) -0.0004(6) 0.0013(8)
C2 0.0118(8) 0.0116(9) 0.0193(9) 0.0015(7) -0.0007(7) -0.0019(7)
C3 0.0120(7) 0.0140(9) 0.0166(8) -0.0011(9) -0.0013(7) -0.0008(7)
C4 0.0142(9) 0.0128(9) 0.0136(8) 0.0003(8) 0.0004(9) 0.0011(7)
C5 0.0147(9) 0.0099(9) 0.0181(10) 0.0002(7) 0.0002(7) -0.0018(7)
C6 0.0093(9) 0.0169(10) 0.0168(8) -0.0019(7) -0.0006(9) -0.0006(8)
O7 0.0110(7) 0.0155(8) 0.0225(7) -0.0009(6) -0.0018(6) -0.0024(5)
C8 0.0160(8) 0.0198(10) 0.0135(8) 0.0009(8) 0.0000(7) 0.0008(9)
O8 0.0106(6) 0.0288(10) 0.0275(7) 0.0006(7) 0.0004(5) 0.0010(6)
C9 0.0129(10) 0.0144(10) 0.0187(9) 0.0001(7) -0.0005(8) 0.0029(8)
C10 0.0174(9) 0.0215(11) 0.0164(8) 0.0024(8) -0.0018(8) -0.0009(9)
C11 0.0187(10) 0.0156(10) 0.0153(9) 0.0028(8) -0.0012(7) 0.0023(8)
C12 0.0202(10) 0.0230(11) 0.0219(9) 0.0033(8) -0.0060(10) 0.0016(10)
C13 0.0304(13) 0.0310(13) 0.0166(10) 0.0029(9) 0.0011(9) 0.0055(11)
_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
I C5 2.184(2) . ?
C1 C9 1.533(3) . ?
C1 C2 1.534(3) . ?
C1 C10 1.537(2) . ?
C1 C6 1.554(3) . ?
C2 C3 1.522(3) . ?
C2 H2E 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C4 1.547(3) . ?
C3 H3E 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C5 1.532(3) . ?
C4 C11 1.541(3) . ?
C4 H4A 1.0000 . ?
C5 C6 1.529(3) . ?
C5 H5A 1.0000 . ?
C6 O7 1.466(2) . ?
C6 H6A 1.0000 . ?
O7 C8 1.364(3) . ?
C8 O8 1.201(2) . ?
C8 C9 1.504(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.529(3) . ?
C11 C12 1.533(3) . ?
C11 H11A 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C9 C1 C2 115.45(17) . . ?
C9 C1 C10 108.96(15) . . ?
C2 C1 C10 109.38(16) . . ?
C9 C1 C6 100.40(15) . . ?
C2 C1 C6 112.80(17) . . ?
C10 C1 C6 109.46(17) . . ?
C3 C2 C1 113.88(16) . . ?
C3 C2 H2E 108.8 . . ?
C1 C2 H2E 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
H2E C2 H2A 107.7 . . ?
C2 C3 C4 110.61(17) . . ?
C2 C3 H3E 109.5 . . ?
C4 C3 H3E 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
H3E C3 H3A 108.1 . . ?
C5 C4 C11 115.36(17) . . ?
C5 C4 C3 104.89(15) . . ?
C11 C4 C3 113.71(18) . . ?
C5 C4 H4A 107.5 . . ?
C11 C4 H4A 107.5 . . ?
C3 C4 H4A 107.5 . . ?
C6 C5 C4 112.04(17) . . ?
C6 C5 I 107.68(13) . . ?
C4 C5 I 113.49(13) . . ?
C6 C5 H5A 107.8 . . ?
C4 C5 H5A 107.8 . . ?
I C5 H5A 107.8 . . ?
O7 C6 C5 109.07(16) . . ?
O7 C6 C1 103.47(16) . . ?
C5 C6 C1 113.73(16) . . ?
O7 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
C1 C6 H6A 110.1 . . ?
C8 O7 C6 109.89(16) . . ?
O8 C8 O7 121.2(2) . . ?
O8 C8 C9 129.0(2) . . ?
O7 C8 C9 109.77(16) . . ?
C8 C9 C1 102.64(17) . . ?
C8 C9 H9A 111.2 . . ?
C1 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C1 C9 H9B 111.2 . . ?
H9A C9 H9B 109.2 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C12 110.64(18) . . ?
C13 C11 C4 113.43(18) . . ?
C12 C11 C4 111.44(17) . . ?
C13 C11 H11A 107.0 . . ?
C12 C11 H11A 107.0 . . ?
C4 C11 H11A 107.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C9 C1 C2 C3 -72.0(2) . . . . ?
C10 C1 C2 C3 164.72(17) . . . . ?
C6 C1 C2 C3 42.7(2) . . . . ?
C1 C2 C3 C4 -56.8(2) . . . . ?
C2 C3 C4 C5 65.1(2) . . . . ?
C2 C3 C4 C11 -167.98(16) . . . . ?
C11 C4 C5 C6 170.50(17) . . . . ?
C3 C4 C5 C6 -63.6(2) . . . . ?
C11 C4 C5 I 48.3(2) . . . . ?
C3 C4 C5 I 174.19(13) . . . . ?
C4 C5 C6 O7 167.93(15) . . . . ?
I C5 C6 O7 -66.58(17) . . . . ?
C4 C5 C6 C1 53.0(2) . . . . ?
I C5 C6 C1 178.51(13) . . . . ?
C9 C1 C6 O7 -35.13(17) . . . . ?
C2 C1 C6 O7 -158.58(16) . . . . ?
C10 C1 C6 O7 79.39(17) . . . . ?
C9 C1 C6 C5 83.04(19) . . . . ?
C2 C1 C6 C5 -40.4(2) . . . . ?
C10 C1 C6 C5 -162.43(16) . . . . ?
C5 C6 O7 C8 -98.15(18) . . . . ?
C1 C6 O7 C8 23.22(19) . . . . ?
C6 O7 C8 O8 -179.45(18) . . . . ?
C6 O7 C8 C9 -0.7(2) . . . . ?
O8 C8 C9 C1 156.3(2) . . . . ?
O7 C8 C9 C1 -22.3(2) . . . . ?
C2 C1 C9 C8 155.79(17) . . . . ?
C10 C1 C9 C8 -80.70(19) . . . . ?
C6 C1 C9 C8 34.21(18) . . . . ?
C5 C4 C11 C13 58.0(2) . . . . ?
C3 C4 C11 C13 -63.3(2) . . . . ?
C5 C4 C11 C12 -176.37(17) . . . . ?
C3 C4 C11 C12 62.4(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 26.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.932
_refine_diff_density_min -0.310
_refine_diff_density_rms 0.075
#===== end
data_(-)-4b
_database_code_depnum_ccdc_archive 'CCDC 825644'
#TrackingRef 'OBC-Synthesis-of-piperitone-derived-halogenated-lactones.cif.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(-)-(1R,4S,5S,6S)-5-iodo-4-isopropyl
-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H19 I O2'
_chemical_formula_sum 'C12 H19 I O2'
_chemical_formula_weight 322.17
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 8.140(2)
_cell_length_b 8.210(2)
_cell_length_c 18.954(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1266.7(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 10489
_cell_measurement_theta_min 3.22
_cell_measurement_theta_max 28.73
_exptl_crystal_description needle
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.48
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_min 0.06
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.689
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 2.509
_exptl_absorpt_correction_T_min 0.374
_exptl_absorpt_correction_T_max 0.859
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 10807
_diffrn_reflns_av_R_equivalents 0.0288
_diffrn_reflns_av_sigmaI/netI 0.0171
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 3.28
_diffrn_reflns_theta_max 26.99
_reflns_number_total 2774
_reflns_number_gt 2726
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0203P)^2^+0.3864P] 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 ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.001(15)
_refine_ls_number_reflns 2774
_refine_ls_number_parameters 136
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0157
_refine_ls_R_factor_gt 0.0154
_refine_ls_wR_factor_ref 0.0381
_refine_ls_wR_factor_gt 0.0380
_refine_ls_goodness_of_fit_ref 1.090
_refine_ls_restrained_S_all 1.090
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
I I 0.428381(15) 0.974259(16) 0.136239(7) 0.02389(5) Uani 1 1 d . . .
C1 C 0.39925(19) 0.4804(2) 0.03478(9) 0.0131(3) Uani 1 1 d . . .
C2 C 0.2298(2) 0.4245(2) 0.06008(10) 0.0149(4) Uani 1 1 d . . .
H2A H 0.1460 0.4626 0.0260 0.018 Uiso 1 1 calc R . .
H2E H 0.2270 0.3039 0.0603 0.018 Uiso 1 1 calc R . .
C3 C 0.18413(19) 0.4858(2) 0.13323(10) 0.0140(3) Uani 1 1 d . . .
H3A H 0.2608 0.4397 0.1685 0.017 Uiso 1 1 calc R . .
H3E H 0.0717 0.4492 0.1452 0.017 Uiso 1 1 calc R . .
C4 C 0.1919(2) 0.6733(2) 0.13586(11) 0.0133(3) Uani 1 1 d . . .
H4A H 0.1295 0.7157 0.0943 0.016 Uiso 1 1 calc R . .
C5 C 0.3734(2) 0.7153(2) 0.12450(10) 0.0143(4) Uani 1 1 d . . .
H5A H 0.4388 0.6548 0.1607 0.017 Uiso 1 1 calc R . .
C6 C 0.4341(2) 0.6619(2) 0.05180(9) 0.0140(3) Uani 1 1 d . . .
H6A H 0.3853 0.7332 0.0145 0.017 Uiso 1 1 calc R . .
O7 O 0.61424(15) 0.67273(18) 0.04983(7) 0.0170(3) Uani 1 1 d . . .
C8 C 0.6808(2) 0.5225(3) 0.06170(9) 0.0164(3) Uani 1 1 d . . .
O8 O 0.82679(15) 0.50310(19) 0.06191(7) 0.0217(3) Uani 1 1 d . . .
C9 C 0.5462(2) 0.3992(2) 0.07169(10) 0.0160(4) Uani 1 1 d . . .
H9A H 0.5234 0.3806 0.1224 0.019 Uiso 1 1 calc R . .
H9B H 0.5745 0.2941 0.0491 0.019 Uiso 1 1 calc R . .
C10 C 0.4138(2) 0.4526(3) -0.04529(9) 0.0186(4) Uani 1 1 d . . .
H10A H 0.5221 0.4888 -0.0615 0.028 Uiso 1 1 calc R . .
H10B H 0.3282 0.5148 -0.0697 0.028 Uiso 1 1 calc R . .
H10C H 0.4003 0.3364 -0.0556 0.028 Uiso 1 1 calc R . .
C11 C 0.1139(2) 0.7470(3) 0.20282(10) 0.0169(4) Uani 1 1 d . . .
H11A H 0.1241 0.8681 0.1987 0.020 Uiso 1 1 calc R . .
C12 C -0.0700(3) 0.7081(3) 0.20706(10) 0.0213(4) Uani 1 1 d . . .
H12A H -0.1236 0.7406 0.1630 0.032 Uiso 1 1 calc R . .
H12B H -0.1191 0.7679 0.2465 0.032 Uiso 1 1 calc R . .
H12C H -0.0850 0.5909 0.2144 0.032 Uiso 1 1 calc R . .
C13 C 0.2008(3) 0.6974(3) 0.27080(11) 0.0257(5) Uani 1 1 d . . .
H13A H 0.3179 0.7239 0.2672 0.038 Uiso 1 1 calc R . .
H13B H 0.1878 0.5800 0.2782 0.038 Uiso 1 1 calc R . .
H13C H 0.1526 0.7565 0.3107 0.038 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
I 0.02517(7) 0.01356(7) 0.03294(7) -0.00515(5) 0.00397(6) -0.00518(5)
C1 0.0130(7) 0.0117(8) 0.0145(7) -0.0011(7) -0.0002(6) 0.0004(7)
C2 0.0132(8) 0.0119(8) 0.0196(9) -0.0012(7) -0.0004(7) -0.0009(7)
C3 0.0132(7) 0.0118(8) 0.0170(8) 0.0017(8) 0.0005(6) -0.0007(6)
C4 0.0141(8) 0.0120(8) 0.0139(8) -0.0004(8) -0.0010(8) 0.0006(6)
C5 0.0151(8) 0.0098(9) 0.0180(9) -0.0003(7) -0.0006(6) -0.0018(6)
C6 0.0110(8) 0.0142(9) 0.0169(8) 0.0012(6) 0.0010(8) -0.0006(8)
O7 0.0124(6) 0.0158(7) 0.0230(7) 0.0015(6) 0.0014(5) -0.0020(5)
C8 0.0175(8) 0.0187(9) 0.0131(7) -0.0012(8) -0.0003(6) 0.0008(8)
O8 0.0116(5) 0.0271(9) 0.0265(7) -0.0003(6) -0.0008(5) 0.0006(6)
C9 0.0152(9) 0.0148(9) 0.0182(8) 0.0009(7) 0.0004(7) 0.0011(7)
C10 0.0184(8) 0.0215(10) 0.0160(8) -0.0037(7) 0.0015(7) -0.0023(9)
C11 0.0189(9) 0.0172(10) 0.0148(9) -0.0031(7) 0.0017(7) 0.0013(7)
C12 0.0211(9) 0.0208(10) 0.0221(9) -0.0033(7) 0.0068(9) 0.0016(10)
C13 0.0310(11) 0.0294(12) 0.0166(10) -0.0035(9) -0.0018(8) 0.0057(10)
_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
I C5 2.184(2) . ?
C1 C2 1.531(2) . ?
C1 C9 1.538(2) . ?
C1 C10 1.539(2) . ?
C1 C6 1.551(3) . ?
C2 C3 1.521(3) . ?
C2 H2A 0.9900 . ?
C2 H2E 0.9900 . ?
C3 C4 1.541(2) . ?
C3 H3A 0.9900 . ?
C3 H3E 0.9900 . ?
C4 C5 1.532(2) . ?
C4 C11 1.543(3) . ?
C4 H4A 1.0000 . ?
C5 C6 1.528(2) . ?
C5 H5A 1.0000 . ?
C6 O7 1.470(2) . ?
C6 H6A 1.0000 . ?
O7 C8 1.366(3) . ?
C8 O8 1.199(2) . ?
C8 C9 1.503(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C13 1.525(3) . ?
C11 C12 1.533(3) . ?
C11 H11A 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C2 C1 C9 115.35(16) . . ?
C2 C1 C10 109.49(14) . . ?
C9 C1 C10 108.92(14) . . ?
C2 C1 C6 112.81(15) . . ?
C9 C1 C6 100.38(14) . . ?
C10 C1 C6 109.49(16) . . ?
C3 C2 C1 113.97(15) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2E 108.8 . . ?
C1 C2 H2E 108.8 . . ?
H2A C2 H2E 107.7 . . ?
C2 C3 C4 110.49(16) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3E 109.6 . . ?
C4 C3 H3E 109.6 . . ?
H3A C3 H3E 108.1 . . ?
C5 C4 C3 105.08(14) . . ?
C5 C4 C11 115.09(16) . . ?
C3 C4 C11 113.67(17) . . ?
C5 C4 H4A 107.5 . . ?
C3 C4 H4A 107.5 . . ?
C11 C4 H4A 107.5 . . ?
C6 C5 C4 111.94(15) . . ?
C6 C5 I 107.74(12) . . ?
C4 C5 I 113.72(12) . . ?
C6 C5 H5A 107.7 . . ?
C4 C5 H5A 107.7 . . ?
I C5 H5A 107.7 . . ?
O7 C6 C5 109.14(14) . . ?
O7 C6 C1 103.59(14) . . ?
C5 C6 C1 113.83(15) . . ?
O7 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C1 C6 H6A 110.0 . . ?
C8 O7 C6 109.69(14) . . ?
O8 C8 O7 120.88(19) . . ?
O8 C8 C9 129.2(2) . . ?
O7 C8 C9 109.87(15) . . ?
C8 C9 C1 102.56(15) . . ?
C8 C9 H9A 111.3 . . ?
C1 C9 H9A 111.3 . . ?
C8 C9 H9B 111.3 . . ?
C1 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C12 110.67(17) . . ?
C13 C11 C4 113.51(16) . . ?
C12 C11 C4 111.30(16) . . ?
C13 C11 H11A 107.0 . . ?
C12 C11 H11A 107.0 . . ?
C4 C11 H11A 107.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C9 C1 C2 C3 72.0(2) . . . . ?
C10 C1 C2 C3 -164.74(16) . . . . ?
C6 C1 C2 C3 -42.5(2) . . . . ?
C1 C2 C3 C4 56.8(2) . . . . ?
C2 C3 C4 C5 -65.16(19) . . . . ?
C2 C3 C4 C11 168.14(14) . . . . ?
C3 C4 C5 C6 63.5(2) . . . . ?
C11 C4 C5 C6 -170.64(16) . . . . ?
C3 C4 C5 I -174.07(12) . . . . ?
C11 C4 C5 I -48.25(19) . . . . ?
C4 C5 C6 O7 -167.87(14) . . . . ?
I C5 C6 O7 66.39(15) . . . . ?
C4 C5 C6 C1 -52.7(2) . . . . ?
I C5 C6 C1 -178.45(12) . . . . ?
C2 C1 C6 O7 158.58(14) . . . . ?
C9 C1 C6 O7 35.27(16) . . . . ?
C10 C1 C6 O7 -79.22(16) . . . . ?
C2 C1 C6 C5 40.2(2) . . . . ?
C9 C1 C6 C5 -83.13(17) . . . . ?
C10 C1 C6 C5 162.38(14) . . . . ?
C5 C6 O7 C8 98.27(17) . . . . ?
C1 C6 O7 C8 -23.33(18) . . . . ?
C6 O7 C8 O8 179.49(16) . . . . ?
C6 O7 C8 C9 0.7(2) . . . . ?
O8 C8 C9 C1 -156.33(19) . . . . ?
O7 C8 C9 C1 22.37(19) . . . . ?
C2 C1 C9 C8 -155.85(16) . . . . ?
C10 C1 C9 C8 80.60(18) . . . . ?
C6 C1 C9 C8 -34.32(16) . . . . ?
C5 C4 C11 C13 -58.2(2) . . . . ?
C3 C4 C11 C13 63.1(2) . . . . ?
C5 C4 C11 C12 176.15(16) . . . . ?
C3 C4 C11 C12 -62.6(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 26.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.641
_refine_diff_density_min -0.224
_refine_diff_density_rms 0.069
#===== end
data_(+/-)4c
_database_code_depnum_ccdc_archive 'CCDC 825645'
#TrackingRef 'OBC-Synthesis-of-piperitone-derived-halogenated-lactones.cif.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(+/-)-c-5-iodo-t-4-isopropyl-r
-1-methyl-7-oxa-cis-bicyclo[4.3.0]nonan-8-one
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H19 I O2'
_chemical_formula_sum 'C12 H19 I O2'
_chemical_formula_weight 322.17
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting TRICLINIC
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.690(2)
_cell_length_b 11.404(2)
_cell_length_c 12.212(3)
_cell_angle_alpha 79.09(4)
_cell_angle_beta 84.20(3)
_cell_angle_gamma 86.93(3)
_cell_volume 1317.5(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 3260
_cell_measurement_theta_min 3.38
_cell_measurement_theta_max 26.99
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.624
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 2.412
_exptl_absorpt_correction_type refdelf
_exptl_absorpt_factor_muR 0.000
loop_
_exptl_absorpt_process_details
'Sheldrick, G.M. (anon) SHELX97 Release 97-2 (1998)'
'I/sigma threshold for reflections = 5.000'
'Delta(U)/lambda**2 = 0.000'
'Highest even order spherical harmonic = 6'
'Highest odd order spherical harmonic = 3'
_exptl_absorpt_correction_T_min 0.7122
_exptl_absorpt_correction_T_max 0.9187
_exptl_absorpt_Rmerge_before 0.0273
_exptl_absorpt_Rmerge_after 0.0223
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 7513
_diffrn_reflns_av_R_equivalents 0.0196
_diffrn_reflns_av_sigmaI/netI 0.0226
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 3.38
_diffrn_reflns_theta_max 25.00
_reflns_number_total 4520
_reflns_number_gt 3931
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0281P)^2^+0.5078P] 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 4520
_refine_ls_number_parameters 271
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0272
_refine_ls_R_factor_gt 0.0218
_refine_ls_wR_factor_ref 0.0526
_refine_ls_wR_factor_gt 0.0514
_refine_ls_goodness_of_fit_ref 1.091
_refine_ls_restrained_S_all 1.091
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
I01 I 0.078829(19) -0.374424(16) -0.415119(15) 0.02773(7) Uani 1 1 d . . .
C06 C 0.3369(3) -0.3949(2) -0.2911(2) 0.0167(5) Uani 1 1 d . . .
H06A H 0.2700 -0.3978 -0.2227 0.020 Uiso 1 1 calc R . .
C05 C 0.2799(3) -0.3110(2) -0.3898(2) 0.0161(5) Uani 1 1 d . . .
H05A H 0.3441 -0.3181 -0.4579 0.019 Uiso 1 1 calc R . .
C04 C 0.2786(3) -0.1812(2) -0.3748(2) 0.0168(5) Uani 1 1 d . . .
H04A H 0.2320 -0.1769 -0.2987 0.020 Uiso 1 1 calc R . .
C03 C 0.4317(3) -0.1529(2) -0.3753(2) 0.0195(6) Uani 1 1 d . . .
H03A H 0.4832 -0.1685 -0.4456 0.023 Uiso 1 1 calc R . .
H03E H 0.4389 -0.0672 -0.3729 0.023 Uiso 1 1 calc R . .
C02 C 0.4971(3) -0.2282(2) -0.2757(2) 0.0227(6) Uani 1 1 d . . .
H02A H 0.4535 -0.2040 -0.2061 0.027 Uiso 1 1 calc R . .
H02E H 0.5970 -0.2113 -0.2820 0.027 Uiso 1 1 calc R . .
C01 C 0.4820(3) -0.3627(2) -0.2662(2) 0.0177(5) Uani 1 1 d . . .
C09 C 0.5733(3) -0.4214(2) -0.3528(2) 0.0221(6) Uani 1 1 d . . .
H09B H 0.5834 -0.3673 -0.4266 0.027 Uiso 1 1 calc R . .
H09A H 0.6665 -0.4447 -0.3276 0.027 Uiso 1 1 calc R . .
C08 C 0.4929(3) -0.5298(2) -0.3578(2) 0.0231(6) Uani 1 1 d . . .
O08 O 0.5335(2) -0.62069(17) -0.38939(15) 0.0332(5) Uani 1 1 d . . .
O07 O 0.35935(19) -0.51416(15) -0.31837(14) 0.0211(4) Uani 1 1 d . . .
C011 C 0.2012(3) -0.0920(2) -0.4612(2) 0.0245(6) Uani 1 1 d . . .
H011 H 0.1037 -0.1186 -0.4552 0.029 Uiso 1 1 calc R . .
C012 C 0.2626(4) -0.0918(3) -0.5820(2) 0.0353(7) Uani 1 1 d . . .
H12F H 0.2103 -0.0338 -0.6334 0.053 Uiso 1 1 calc R . .
H12E H 0.2568 -0.1716 -0.5995 0.053 Uiso 1 1 calc R . .
H12D H 0.3600 -0.0697 -0.5902 0.053 Uiso 1 1 calc R . .
C013 C 0.1940(3) 0.0339(3) -0.4347(3) 0.0318(7) Uani 1 1 d . . .
H13F H 0.1538 0.0315 -0.3574 0.048 Uiso 1 1 calc R . .
H13E H 0.1359 0.0862 -0.4861 0.048 Uiso 1 1 calc R . .
H13D H 0.2877 0.0648 -0.4436 0.048 Uiso 1 1 calc R . .
C010 C 0.5119(3) -0.4263(2) -0.1482(2) 0.0237(6) Uani 1 1 d . . .
H10F H 0.4538 -0.3896 -0.0924 0.035 Uiso 1 1 calc R . .
H10E H 0.6100 -0.4188 -0.1383 0.035 Uiso 1 1 calc R . .
H10D H 0.4911 -0.5110 -0.1384 0.035 Uiso 1 1 calc R . .
I1 I 0.088496(19) 0.121257(16) 0.161992(14) 0.02570(6) Uani 1 1 d . . .
C6 C -0.0694(3) 0.2309(2) -0.0355(2) 0.0160(5) Uani 1 1 d . . .
H6A H -0.1146 0.1518 -0.0187 0.019 Uiso 1 1 calc R . .
C5 C 0.0830(3) 0.2145(2) -0.01173(19) 0.0159(5) Uani 1 1 d . . .
H5A H 0.1204 0.2957 -0.0175 0.019 Uiso 1 1 calc R . .
C4 C 0.1702(3) 0.1523(2) -0.0965(2) 0.0174(5) Uani 1 1 d . . .
H4A H 0.1223 0.0782 -0.1014 0.021 Uiso 1 1 calc R . .
C3 C 0.1637(3) 0.2387(2) -0.2092(2) 0.0194(5) Uani 1 1 d . . .
H3A H 0.1963 0.3177 -0.2027 0.023 Uiso 1 1 calc R . .
H3E H 0.2259 0.2079 -0.2675 0.023 Uiso 1 1 calc R . .
C2 C 0.0158(3) 0.2527(2) -0.2437(2) 0.0202(6) Uani 1 1 d . . .
H2A H -0.0122 0.1751 -0.2579 0.024 Uiso 1 1 calc R . .
H2E H 0.0144 0.3112 -0.3148 0.024 Uiso 1 1 calc R . .
C1 C -0.0902(3) 0.2941(2) -0.1563(2) 0.0167(5) Uani 1 1 d . . .
C9 C -0.0809(3) 0.4247(2) -0.1435(2) 0.0174(5) Uani 1 1 d . . .
H9B H 0.0166 0.4497 -0.1551 0.021 Uiso 1 1 calc R . .
H9A H -0.1360 0.4788 -0.1974 0.021 Uiso 1 1 calc R . .
C8 C -0.1407(3) 0.4244(2) -0.0246(2) 0.0168(5) Uani 1 1 d . . .
O8 O -0.18458(18) 0.50664(16) 0.01851(15) 0.0217(4) Uani 1 1 d . . .
O7 O -0.13948(18) 0.31101(15) 0.03426(14) 0.0183(4) Uani 1 1 d . . .
C11 C 0.3195(3) 0.1153(2) -0.0670(2) 0.0222(6) Uani 1 1 d . . .
H11 H 0.3123 0.0593 0.0068 0.027 Uiso 1 1 calc R . .
C12 C 0.3963(3) 0.0472(3) -0.1531(3) 0.0393(8) Uani 1 1 d . . .
H12A H 0.4904 0.0245 -0.1323 0.059 Uiso 1 1 calc R . .
H12B H 0.4012 0.0984 -0.2274 0.059 Uiso 1 1 calc R . .
H12C H 0.3462 -0.0249 -0.1546 0.059 Uiso 1 1 calc R . .
C13 C 0.4029(3) 0.2211(3) -0.0537(3) 0.0300(7) Uani 1 1 d . . .
H13A H 0.4964 0.1926 -0.0348 0.045 Uiso 1 1 calc R . .
H13B H 0.3564 0.2590 0.0063 0.045 Uiso 1 1 calc R . .
H13C H 0.4095 0.2792 -0.1241 0.045 Uiso 1 1 calc R . .
C10 C -0.2372(3) 0.2729(2) -0.1829(2) 0.0246(6) Uani 1 1 d . . .
H10A H -0.3052 0.2997 -0.1270 0.037 Uiso 1 1 calc R . .
H10B H -0.2471 0.1874 -0.1811 0.037 Uiso 1 1 calc R . .
H10C H -0.2531 0.3178 -0.2575 0.037 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
I01 0.02814(11) 0.03091(11) 0.02399(11) 0.00306(8) -0.01051(8) -0.01374(8)
C06 0.0222(14) 0.0157(12) 0.0125(12) -0.0038(10) -0.0013(10) -0.0006(10)
C05 0.0163(13) 0.0189(13) 0.0128(12) -0.0012(10) -0.0017(10) -0.0043(10)
C04 0.0182(13) 0.0192(13) 0.0135(12) -0.0035(10) -0.0022(10) -0.0026(10)
C03 0.0202(14) 0.0146(13) 0.0241(14) -0.0037(11) -0.0042(11) -0.0008(10)
C02 0.0213(14) 0.0208(14) 0.0279(16) -0.0062(12) -0.0098(11) 0.0013(11)
C01 0.0215(14) 0.0165(13) 0.0159(13) -0.0040(10) -0.0050(10) 0.0022(10)
C09 0.0222(14) 0.0248(14) 0.0188(13) -0.0038(11) -0.0031(11) 0.0057(11)
C08 0.0409(18) 0.0202(14) 0.0075(12) 0.0000(10) -0.0076(11) 0.0058(12)
O08 0.0598(15) 0.0224(11) 0.0186(10) -0.0078(8) -0.0089(9) 0.0128(10)
O07 0.0330(11) 0.0131(9) 0.0180(9) -0.0030(7) -0.0053(8) -0.0017(8)
C011 0.0235(15) 0.0207(14) 0.0280(15) 0.0023(11) -0.0099(12) 0.0001(11)
C012 0.056(2) 0.0266(15) 0.0228(16) 0.0052(12) -0.0177(14) -0.0025(14)
C013 0.0276(17) 0.0252(15) 0.0423(18) -0.0039(13) -0.0103(14) 0.0063(12)
C010 0.0289(15) 0.0259(15) 0.0176(14) -0.0063(11) -0.0075(11) 0.0039(12)
I1 0.03208(12) 0.02716(11) 0.01549(10) 0.00455(7) -0.00619(7) -0.00248(8)
C6 0.0185(13) 0.0137(12) 0.0163(13) -0.0046(10) -0.0002(10) -0.0006(10)
C5 0.0217(14) 0.0135(12) 0.0112(12) 0.0018(9) -0.0034(10) -0.0002(10)
C4 0.0191(14) 0.0136(12) 0.0207(13) -0.0042(10) -0.0052(10) -0.0007(10)
C3 0.0211(14) 0.0197(13) 0.0178(14) -0.0058(11) 0.0002(10) 0.0008(11)
C2 0.0285(15) 0.0197(13) 0.0134(12) -0.0052(10) -0.0059(11) 0.0041(11)
C1 0.0186(13) 0.0150(12) 0.0171(13) -0.0041(10) -0.0041(10) 0.0023(10)
C9 0.0220(14) 0.0146(12) 0.0150(13) -0.0008(10) -0.0030(10) 0.0002(10)
C8 0.0150(13) 0.0181(13) 0.0184(13) -0.0039(11) -0.0043(10) -0.0028(10)
O8 0.0224(10) 0.0218(10) 0.0230(10) -0.0108(8) -0.0003(8) 0.0013(8)
O7 0.0204(9) 0.0184(9) 0.0151(9) -0.0025(7) 0.0016(7) 0.0002(7)
C11 0.0243(15) 0.0183(13) 0.0250(15) -0.0064(11) -0.0062(11) 0.0044(11)
C12 0.0307(17) 0.046(2) 0.047(2) -0.0237(16) -0.0115(15) 0.0229(15)
C13 0.0187(15) 0.0354(17) 0.0375(17) -0.0077(14) -0.0087(12) -0.0007(12)
C10 0.0236(15) 0.0252(14) 0.0285(15) -0.0108(12) -0.0096(12) 0.0012(12)
_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
I01 C05 2.184(2) . ?
C06 O07 1.461(3) . ?
C06 C05 1.522(3) . ?
C06 C01 1.545(4) . ?
C06 H06A 1.0000 . ?
C05 C04 1.525(3) . ?
C05 H05A 1.0000 . ?
C04 C03 1.533(3) . ?
C04 C011 1.544(3) . ?
C04 H04A 1.0000 . ?
C03 C02 1.523(4) . ?
C03 H03A 0.9900 . ?
C03 H03E 0.9900 . ?
C02 C01 1.530(3) . ?
C02 H02A 0.9900 . ?
C02 H02E 0.9900 . ?
C01 C010 1.534(3) . ?
C01 C09 1.538(3) . ?
C09 C08 1.510(4) . ?
C09 H09B 0.9900 . ?
C09 H09A 0.9900 . ?
C08 O08 1.207(3) . ?
C08 O07 1.349(3) . ?
C011 C013 1.527(4) . ?
C011 C012 1.533(4) . ?
C011 H011 1.0000 . ?
C012 H12F 0.9800 . ?
C012 H12E 0.9800 . ?
C012 H12D 0.9800 . ?
C013 H13F 0.9800 . ?
C013 H13E 0.9800 . ?
C013 H13D 0.9800 . ?
C010 H10F 0.9800 . ?
C010 H10E 0.9800 . ?
C010 H10D 0.9800 . ?
I1 C5 2.190(2) . ?
C6 O7 1.460(3) . ?
C6 C5 1.528(3) . ?
C6 C1 1.543(3) . ?
C6 H6A 1.0000 . ?
C5 C4 1.526(3) . ?
C5 H5A 1.0000 . ?
C4 C3 1.539(3) . ?
C4 C11 1.543(4) . ?
C4 H4A 1.0000 . ?
C3 C2 1.526(4) . ?
C3 H3A 0.9900 . ?
C3 H3E 0.9900 . ?
C2 C1 1.528(3) . ?
C2 H2A 0.9900 . ?
C2 H2E 0.9900 . ?
C1 C10 1.533(4) . ?
C1 C9 1.534(3) . ?
C9 C8 1.507(3) . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C8 O8 1.199(3) . ?
C8 O7 1.356(3) . ?
C11 C13 1.530(4) . ?
C11 C12 1.533(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
O07 C06 C05 109.08(19) . . ?
O07 C06 C01 103.71(19) . . ?
C05 C06 C01 113.7(2) . . ?
O07 C06 H06A 110.0 . . ?
C05 C06 H06A 110.0 . . ?
C01 C06 H06A 110.0 . . ?
C06 C05 C04 111.31(19) . . ?
C06 C05 I01 108.24(16) . . ?
C04 C05 I01 114.97(16) . . ?
C06 C05 H05A 107.3 . . ?
C04 C05 H05A 107.3 . . ?
I01 C05 H05A 107.3 . . ?
C05 C04 C03 105.2(2) . . ?
C05 C04 C011 114.8(2) . . ?
C03 C04 C011 113.2(2) . . ?
C05 C04 H04A 107.8 . . ?
C03 C04 H04A 107.8 . . ?
C011 C04 H04A 107.8 . . ?
C02 C03 C04 111.5(2) . . ?
C02 C03 H03A 109.3 . . ?
C04 C03 H03A 109.3 . . ?
C02 C03 H03E 109.3 . . ?
C04 C03 H03E 109.3 . . ?
H03A C03 H03E 108.0 . . ?
C03 C02 C01 113.7(2) . . ?
C03 C02 H02A 108.8 . . ?
C01 C02 H02A 108.8 . . ?
C03 C02 H02E 108.8 . . ?
C01 C02 H02E 108.8 . . ?
H02A C02 H02E 107.7 . . ?
C02 C01 C010 109.1(2) . . ?
C02 C01 C09 115.8(2) . . ?
C010 C01 C09 108.9(2) . . ?
C02 C01 C06 112.9(2) . . ?
C010 C01 C06 109.8(2) . . ?
C09 C01 C06 99.91(19) . . ?
C08 C09 C01 102.5(2) . . ?
C08 C09 H09B 111.3 . . ?
C01 C09 H09B 111.3 . . ?
C08 C09 H09A 111.3 . . ?
C01 C09 H09A 111.3 . . ?
H09B C09 H09A 109.2 . . ?
O08 C08 O07 121.2(3) . . ?
O08 C08 C09 129.0(3) . . ?
O07 C08 C09 109.9(2) . . ?
C08 O07 C06 109.9(2) . . ?
C013 C011 C012 111.0(2) . . ?
C013 C011 C04 111.6(2) . . ?
C012 C011 C04 112.6(2) . . ?
C013 C011 H011 107.1 . . ?
C012 C011 H011 107.1 . . ?
C04 C011 H011 107.1 . . ?
C011 C012 H12F 109.5 . . ?
C011 C012 H12E 109.5 . . ?
H12F C012 H12E 109.5 . . ?
C011 C012 H12D 109.5 . . ?
H12F C012 H12D 109.5 . . ?
H12E C012 H12D 109.5 . . ?
C011 C013 H13F 109.5 . . ?
C011 C013 H13E 109.5 . . ?
H13F C013 H13E 109.5 . . ?
C011 C013 H13D 109.5 . . ?
H13F C013 H13D 109.5 . . ?
H13E C013 H13D 109.5 . . ?
C01 C010 H10F 109.5 . . ?
C01 C010 H10E 109.5 . . ?
H10F C010 H10E 109.5 . . ?
C01 C010 H10D 109.5 . . ?
H10F C010 H10D 109.5 . . ?
H10E C010 H10D 109.5 . . ?
O7 C6 C5 108.83(19) . . ?
O7 C6 C1 104.15(18) . . ?
C5 C6 C1 113.4(2) . . ?
O7 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
C1 C6 H6A 110.1 . . ?
C4 C5 C6 112.3(2) . . ?
C4 C5 I1 113.78(15) . . ?
C6 C5 I1 107.25(16) . . ?
C4 C5 H5A 107.8 . . ?
C6 C5 H5A 107.8 . . ?
I1 C5 H5A 107.8 . . ?
C5 C4 C3 104.79(19) . . ?
C5 C4 C11 114.8(2) . . ?
C3 C4 C11 113.6(2) . . ?
C5 C4 H4A 107.8 . . ?
C3 C4 H4A 107.8 . . ?
C11 C4 H4A 107.8 . . ?
C2 C3 C4 110.8(2) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3E 109.5 . . ?
C4 C3 H3E 109.5 . . ?
H3A C3 H3E 108.1 . . ?
C3 C2 C1 113.7(2) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2E 108.8 . . ?
C1 C2 H2E 108.8 . . ?
H2A C2 H2E 107.7 . . ?
C2 C1 C10 109.5(2) . . ?
C2 C1 C9 115.4(2) . . ?
C10 C1 C9 109.3(2) . . ?
C2 C1 C6 113.1(2) . . ?
C10 C1 C6 109.3(2) . . ?
C9 C1 C6 99.78(19) . . ?
C8 C9 C1 103.4(2) . . ?
C8 C9 H9B 111.1 . . ?
C1 C9 H9B 111.1 . . ?
C8 C9 H9A 111.1 . . ?
C1 C9 H9A 111.1 . . ?
H9B C9 H9A 109.0 . . ?
O8 C8 O7 121.1(2) . . ?
O8 C8 C9 129.3(2) . . ?
O7 C8 C9 109.6(2) . . ?
C8 O7 C6 109.54(18) . . ?
C13 C11 C12 110.7(2) . . ?
C13 C11 C4 112.9(2) . . ?
C12 C11 C4 111.1(2) . . ?
C13 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C4 C11 H11 107.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O07 C06 C05 C04 -169.87(19) . . . . ?
C01 C06 C05 C04 -54.6(3) . . . . ?
O07 C06 C05 I01 62.9(2) . . . . ?
C01 C06 C05 I01 178.08(16) . . . . ?
C06 C05 C04 C03 64.2(2) . . . . ?
I01 C05 C04 C03 -172.29(15) . . . . ?
C06 C05 C04 C011 -170.7(2) . . . . ?
I01 C05 C04 C011 -47.2(3) . . . . ?
C05 C04 C03 C02 -64.3(3) . . . . ?
C011 C04 C03 C02 169.6(2) . . . . ?
C04 C03 C02 C01 54.7(3) . . . . ?
C03 C02 C01 C010 -163.7(2) . . . . ?
C03 C02 C01 C09 73.0(3) . . . . ?
C03 C02 C01 C06 -41.4(3) . . . . ?
O07 C06 C01 C02 159.8(2) . . . . ?
C05 C06 C01 C02 41.4(3) . . . . ?
O07 C06 C01 C010 -78.3(2) . . . . ?
C05 C06 C01 C010 163.4(2) . . . . ?
O07 C06 C01 C09 36.1(2) . . . . ?
C05 C06 C01 C09 -82.2(2) . . . . ?
C02 C01 C09 C08 -155.1(2) . . . . ?
C010 C01 C09 C08 81.6(2) . . . . ?
C06 C01 C09 C08 -33.5(2) . . . . ?
C01 C09 C08 O08 -158.9(3) . . . . ?
C01 C09 C08 O07 20.2(3) . . . . ?
O08 C08 O07 C06 -177.3(2) . . . . ?
C09 C08 O07 C06 3.5(3) . . . . ?
C05 C06 O07 C08 95.7(2) . . . . ?
C01 C06 O07 C08 -25.8(2) . . . . ?
C05 C04 C011 C013 175.2(2) . . . . ?
C03 C04 C011 C013 -64.0(3) . . . . ?
C05 C04 C011 C012 -59.1(3) . . . . ?
C03 C04 C011 C012 61.6(3) . . . . ?
O7 C6 C5 C4 -168.82(18) . . . . ?
C1 C6 C5 C4 -53.4(3) . . . . ?
O7 C6 C5 I1 65.5(2) . . . . ?
C1 C6 C5 I1 -179.12(16) . . . . ?
C6 C5 C4 C3 63.8(2) . . . . ?
I1 C5 C4 C3 -174.19(15) . . . . ?
C6 C5 C4 C11 -170.9(2) . . . . ?
I1 C5 C4 C11 -48.8(3) . . . . ?
C5 C4 C3 C2 -64.7(2) . . . . ?
C11 C4 C3 C2 169.2(2) . . . . ?
C4 C3 C2 C1 56.3(3) . . . . ?
C3 C2 C1 C10 -164.7(2) . . . . ?
C3 C2 C1 C9 71.5(3) . . . . ?
C3 C2 C1 C6 -42.5(3) . . . . ?
O7 C6 C1 C2 158.8(2) . . . . ?
C5 C6 C1 C2 40.7(3) . . . . ?
O7 C6 C1 C10 -78.9(2) . . . . ?
C5 C6 C1 C10 162.9(2) . . . . ?
O7 C6 C1 C9 35.7(2) . . . . ?
C5 C6 C1 C9 -82.5(2) . . . . ?
C2 C1 C9 C8 -153.8(2) . . . . ?
C10 C1 C9 C8 82.3(2) . . . . ?
C6 C1 C9 C8 -32.2(2) . . . . ?
C1 C9 C8 O8 -161.6(3) . . . . ?
C1 C9 C8 O7 18.4(3) . . . . ?
O8 C8 O7 C6 -174.8(2) . . . . ?
C9 C8 O7 C6 5.1(3) . . . . ?
C5 C6 O7 C8 94.7(2) . . . . ?
C1 C6 O7 C8 -26.5(2) . . . . ?
C5 C4 C11 C13 -58.2(3) . . . . ?
C3 C4 C11 C13 62.4(3) . . . . ?
C5 C4 C11 C12 176.7(2) . . . . ?
C3 C4 C11 C12 -62.7(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max 0.788
_refine_diff_density_min -0.403
_refine_diff_density_rms 0.072
#===== end
data_(+)-5a
_database_code_depnum_ccdc_archive 'CCDC 825646'
#TrackingRef 'OBC-Synthesis-of-piperitone-derived-halogenated-lactones.cif.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(+)-(1S,4R,5R,6R)-5-bromo-4-isopropyl
-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H19 Br O2'
_chemical_formula_sum 'C12 H19 Br O2'
_chemical_formula_weight 275.18
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 7.951(2)
_cell_length_b 8.165(2)
_cell_length_c 19.191(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1245.9(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 8317
_cell_measurement_theta_min 2.77
_cell_measurement_theta_max 28.73
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.52
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.467
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 568
_exptl_absorpt_coefficient_mu 3.280
_exptl_absorpt_correction_T_min 0.368
_exptl_absorpt_correction_T_max 0.789
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 10539
_diffrn_reflns_av_R_equivalents 0.0511
_diffrn_reflns_av_sigmaI/netI 0.0323
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 24
_diffrn_reflns_theta_min 2.77
_diffrn_reflns_theta_max 26.99
_reflns_number_total 2721
_reflns_number_gt 2518
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0356P)^2^+0.0000P] 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 ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack -0.008(8)
_refine_ls_number_reflns 2721
_refine_ls_number_parameters 136
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0270
_refine_ls_R_factor_gt 0.0239
_refine_ls_wR_factor_ref 0.0573
_refine_ls_wR_factor_gt 0.0565
_refine_ls_goodness_of_fit_ref 1.024
_refine_ls_restrained_S_all 1.024
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
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
Br Br 0.77949(3) 0.68518(3) 0.122250(12) 0.02647(8) Uani 1 1 d . . .
C1 C 1.2699(3) 0.6643(2) 0.21594(9) 0.0141(4) Uani 1 1 d . . .
C2 C 1.3261(3) 0.4958(2) 0.19014(11) 0.0155(4) Uani 1 1 d . . .
H2A H 1.2868 0.4118 0.2236 0.019 Uiso 1 1 calc R . .
H2E H 1.4506 0.4924 0.1896 0.019 Uiso 1 1 calc R . .
C3 C 1.2611(2) 0.4517(2) 0.11743(10) 0.0154(4) Uani 1 1 d . . .
H3E H 1.2981 0.3396 0.1051 0.019 Uiso 1 1 calc R . .
H3A H 1.3088 0.5285 0.0827 0.019 Uiso 1 1 calc R . .
C4 C 1.0672(2) 0.4609(2) 0.11548(11) 0.0163(4) Uani 1 1 d . . .
H4A H 1.0237 0.3964 0.1559 0.020 Uiso 1 1 calc R . .
C5 C 1.0235(2) 0.6411(2) 0.12847(11) 0.0173(4) Uani 1 1 d . . .
H5A H 1.0813 0.7083 0.0921 0.021 Uiso 1 1 calc R . .
C6 C 1.0828(3) 0.7011(3) 0.19993(10) 0.0150(4) Uani 1 1 d . . .
H6A H 1.0098 0.6540 0.2373 0.018 Uiso 1 1 calc R . .
O7 O 1.07347(19) 0.88061(17) 0.20135(8) 0.0175(3) Uani 1 1 d . . .
O8 O 1.2490(2) 1.09146(17) 0.18604(8) 0.0232(3) Uani 1 1 d . . .
C8 C 1.2281(3) 0.9457(2) 0.18815(10) 0.0175(4) Uani 1 1 d . . .
C9 C 1.3546(2) 0.8096(3) 0.17942(10) 0.0165(4) Uani 1 1 d . . .
H9A H 1.4629 0.8376 0.2020 0.020 Uiso 1 1 calc R . .
H9B H 1.3749 0.7857 0.1295 0.020 Uiso 1 1 calc R . .
C10 C 1.3000(3) 0.6774(3) 0.29515(9) 0.0189(4) Uani 1 1 d . . .
H10A H 1.4184 0.6543 0.3054 0.028 Uiso 1 1 calc R . .
H10B H 1.2286 0.5981 0.3195 0.028 Uiso 1 1 calc R . .
H10C H 1.2722 0.7884 0.3109 0.028 Uiso 1 1 calc R . .
C11 C 0.9890(3) 0.3874(3) 0.04862(11) 0.0209(5) Uani 1 1 d . . .
H11A H 0.8641 0.3970 0.0533 0.025 Uiso 1 1 calc R . .
C12 C 1.0298(3) 0.2049(3) 0.04204(11) 0.0251(5) Uani 1 1 d . . .
H12A H 0.9785 0.1614 -0.0006 0.038 Uiso 1 1 calc R . .
H12B H 0.9850 0.1462 0.0825 0.038 Uiso 1 1 calc R . .
H12C H 1.1520 0.1901 0.0399 0.038 Uiso 1 1 calc R . .
C13 C 1.0390(3) 0.4797(3) -0.01819(12) 0.0304(5) Uani 1 1 d . . .
H13A H 0.9847 0.4282 -0.0585 0.046 Uiso 1 1 calc R . .
H13B H 1.1614 0.4755 -0.0240 0.046 Uiso 1 1 calc R . .
H13C H 1.0027 0.5941 -0.0147 0.046 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
Br 0.01183(11) 0.03137(11) 0.03622(12) -0.00445(10) -0.00545(9) 0.00550(9)
C1 0.0106(9) 0.0149(9) 0.0168(8) 0.0000(7) -0.0002(7) -0.0020(8)
C2 0.0131(10) 0.0142(10) 0.0193(10) 0.0003(7) -0.0011(8) 0.0003(8)
C3 0.0124(9) 0.0151(8) 0.0188(9) -0.0019(7) 0.0006(8) 0.0008(7)
C4 0.0112(9) 0.0202(10) 0.0175(10) 0.0003(8) 0.0009(8) -0.0018(7)
C5 0.0100(9) 0.0208(10) 0.0212(10) 0.0014(8) -0.0019(9) 0.0004(7)
C6 0.0136(10) 0.0129(10) 0.0185(9) -0.0002(8) 0.0009(7) 0.0003(8)
O7 0.0141(8) 0.0144(7) 0.0241(8) -0.0009(6) 0.0017(6) 0.0023(6)
O8 0.0243(10) 0.0157(7) 0.0296(8) 0.0013(6) 0.0012(7) -0.0002(6)
C8 0.0169(10) 0.0183(10) 0.0172(9) 0.0015(7) -0.0006(8) -0.0004(9)
C9 0.0120(9) 0.0178(9) 0.0198(9) -0.0011(9) 0.0021(7) -0.0004(9)
C10 0.0176(11) 0.0205(9) 0.0187(9) 0.0003(8) -0.0013(7) 0.0011(10)
C11 0.0189(12) 0.0247(11) 0.0191(11) -0.0008(9) -0.0037(8) -0.0015(9)
C12 0.0239(12) 0.0273(11) 0.0239(11) -0.0075(10) -0.0042(9) -0.0026(10)
C13 0.0331(14) 0.0385(13) 0.0196(12) 0.0019(9) -0.0055(10) -0.0054(11)
_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
Br C5 1.977(2) . ?
C1 C2 1.529(3) . ?
C1 C9 1.534(3) . ?
C1 C10 1.543(3) . ?
C1 C6 1.548(3) . ?
C2 C3 1.531(3) . ?
C2 H2A 0.9900 . ?
C2 H2E 0.9900 . ?
C3 C4 1.544(3) . ?
C3 H3E 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C5 1.532(3) . ?
C4 C11 1.547(3) . ?
C4 H4A 1.0000 . ?
C5 C6 1.531(3) . ?
C5 H5A 1.0000 . ?
C6 O7 1.468(3) . ?
C6 H6A 1.0000 . ?
O7 C8 1.363(3) . ?
O8 C8 1.202(2) . ?
C8 C9 1.509(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.531(3) . ?
C11 C13 1.539(3) . ?
C11 H11A 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C2 C1 C9 114.79(17) . . ?
C2 C1 C10 109.65(16) . . ?
C9 C1 C10 109.16(15) . . ?
C2 C1 C6 113.03(16) . . ?
C9 C1 C6 100.46(15) . . ?
C10 C1 C6 109.35(16) . . ?
C1 C2 C3 114.07(16) . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2E 108.7 . . ?
C3 C2 H2E 108.7 . . ?
H2A C2 H2E 107.6 . . ?
C2 C3 C4 110.35(16) . . ?
C2 C3 H3E 109.6 . . ?
C4 C3 H3E 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
H3E C3 H3A 108.1 . . ?
C5 C4 C3 105.61(16) . . ?
C5 C4 C11 114.61(18) . . ?
C3 C4 C11 113.74(17) . . ?
C5 C4 H4A 107.5 . . ?
C3 C4 H4A 107.5 . . ?
C11 C4 H4A 107.5 . . ?
C6 C5 C4 112.53(17) . . ?
C6 C5 Br 107.35(14) . . ?
C4 C5 Br 112.81(13) . . ?
C6 C5 H5A 108.0 . . ?
C4 C5 H5A 108.0 . . ?
Br C5 H5A 108.0 . . ?
O7 C6 C5 108.69(16) . . ?
O7 C6 C1 103.80(16) . . ?
C5 C6 C1 114.31(16) . . ?
O7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C1 C6 H6A 109.9 . . ?
C8 O7 C6 109.89(16) . . ?
O8 C8 O7 121.1(2) . . ?
O8 C8 C9 129.3(2) . . ?
O7 C8 C9 109.57(16) . . ?
C8 C9 C1 103.06(15) . . ?
C8 C9 H9A 111.2 . . ?
C1 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C1 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C13 110.68(19) . . ?
C12 C11 C4 111.17(18) . . ?
C13 C11 C4 113.41(19) . . ?
C12 C11 H11A 107.1 . . ?
C13 C11 H11A 107.1 . . ?
C4 C11 H11A 107.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C9 C1 C2 C3 -71.9(2) . . . . ?
C10 C1 C2 C3 164.82(17) . . . . ?
C6 C1 C2 C3 42.5(2) . . . . ?
C1 C2 C3 C4 -56.7(2) . . . . ?
C2 C3 C4 C5 64.3(2) . . . . ?
C2 C3 C4 C11 -169.13(16) . . . . ?
C3 C4 C5 C6 -62.0(2) . . . . ?
C11 C4 C5 C6 171.96(17) . . . . ?
C3 C4 C5 Br 176.31(13) . . . . ?
C11 C4 C5 Br 50.3(2) . . . . ?
C4 C5 C6 O7 166.43(16) . . . . ?
Br C5 C6 O7 -68.86(18) . . . . ?
C4 C5 C6 C1 51.0(2) . . . . ?
Br C5 C6 C1 175.71(13) . . . . ?
C2 C1 C6 O7 -157.54(16) . . . . ?
C9 C1 C6 O7 -34.73(18) . . . . ?
C10 C1 C6 O7 80.01(18) . . . . ?
C2 C1 C6 C5 -39.3(2) . . . . ?
C9 C1 C6 C5 83.51(19) . . . . ?
C10 C1 C6 C5 -161.75(16) . . . . ?
C5 C6 O7 C8 -98.20(19) . . . . ?
C1 C6 O7 C8 23.9(2) . . . . ?
C6 O7 C8 O8 179.18(18) . . . . ?
C6 O7 C8 C9 -2.1(2) . . . . ?
O8 C8 C9 C1 157.9(2) . . . . ?
O7 C8 C9 C1 -20.7(2) . . . . ?
C2 C1 C9 C8 154.65(16) . . . . ?
C10 C1 C9 C8 -81.80(19) . . . . ?
C6 C1 C9 C8 33.09(18) . . . . ?
C5 C4 C11 C12 -176.45(18) . . . . ?
C3 C4 C11 C12 61.9(2) . . . . ?
C5 C4 C11 C13 58.1(2) . . . . ?
C3 C4 C11 C13 -63.6(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 26.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.711
_refine_diff_density_min -0.221
_refine_diff_density_rms 0.071
#==== end
data_(-)-5b
_database_code_depnum_ccdc_archive 'CCDC 825647'
#TrackingRef 'OBC-Synthesis-of-piperitone-derived-halogenated-lactones.cif.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(-)-(1R,4S,5S,6S)-5-bromo-4-isopropyl
-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H19 Br O2'
_chemical_formula_sum 'C12 H19 Br O2'
_chemical_formula_weight 275.18
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
_cell_length_a 7.954(2)
_cell_length_b 8.158(2)
_cell_length_c 19.177(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 1244.4(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 3733
_cell_measurement_theta_min 3.18
_cell_measurement_theta_max 28.63
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.17
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.05
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.469
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 568
_exptl_absorpt_coefficient_mu 3.284
_exptl_absorpt_correction_type analytical
_exptl_absorpt_correction_T_min 0.655
_exptl_absorpt_correction_T_max 0.879
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May 8 2007,13:10:02)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8483
_diffrn_reflns_av_R_equivalents 0.0682
_diffrn_reflns_av_sigmaI/netI 0.0931
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 3.28
_diffrn_reflns_theta_max 26.99
_reflns_number_total 2715
_reflns_number_gt 2136
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0182P)^2^+0.0000P] 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 ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.015(13)
_refine_ls_number_reflns 2715
_refine_ls_number_parameters 136
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0758
_refine_ls_R_factor_gt 0.0489
_refine_ls_wR_factor_ref 0.0627
_refine_ls_wR_factor_gt 0.0583
_refine_ls_goodness_of_fit_ref 1.011
_refine_ls_restrained_S_all 1.011
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
Br Br 0.22030(5) 0.81481(6) 0.87786(2) 0.02491(12) Uani 1 1 d . . .
O7 O -0.0733(3) 0.6194(3) 0.79874(15) 0.0142(7) Uani 1 1 d . . .
C6 C -0.0828(4) 0.8008(6) 0.7998(2) 0.0135(9) Uani 1 1 d . . .
H6A H -0.0100 0.8480 0.7623 0.016 Uiso 1 1 calc R . .
C5 C -0.0230(4) 0.8595(4) 0.8715(2) 0.0139(9) Uani 1 1 d . . .
H5A H -0.0810 0.7918 0.9077 0.017 Uiso 1 1 calc R . .
C4 C -0.0675(4) 1.0389(4) 0.8846(2) 0.0122(9) Uani 1 1 d . . .
H4A H -0.0242 1.1038 0.8442 0.015 Uiso 1 1 calc R . .
C3 C -0.2614(4) 1.0477(4) 0.8826(2) 0.0131(8) Uani 1 1 d . . .
H3A H -0.3090 0.9703 0.9171 0.016 Uiso 1 1 calc R . .
H3E H -0.2986 1.1597 0.8952 0.016 Uiso 1 1 calc R . .
C2 C -0.3259(5) 1.0045(5) 0.8097(2) 0.0130(10) Uani 1 1 d . . .
H2A H -0.2857 1.0885 0.7764 0.016 Uiso 1 1 calc R . .
H2E H -0.4502 1.0085 0.8100 0.016 Uiso 1 1 calc R . .
C1 C -0.2701(5) 0.8354(5) 0.78384(18) 0.0103(8) Uani 1 1 d . . .
C9 C -0.3537(4) 0.6905(6) 0.82067(19) 0.0133(9) Uani 1 1 d . . .
H9A H -0.3726 0.7145 0.8707 0.016 Uiso 1 1 calc R . .
H9B H -0.4625 0.6626 0.7986 0.016 Uiso 1 1 calc R . .
O8 O -0.2488(3) 0.4094(3) 0.81408(13) 0.0214(7) Uani 1 1 d . . .
C8 C -0.2289(5) 0.5554(5) 0.81149(18) 0.0136(9) Uani 1 1 d . . .
C11 C 0.0113(5) 1.1119(5) 0.9516(2) 0.0148(10) Uani 1 1 d . . .
H11 H 0.1361 1.1026 0.9467 0.018 Uiso 1 1 calc R . .
C12 C -0.0378(6) 1.0200(5) 1.0179(2) 0.0272(12) Uani 1 1 d . . .
H12A H 0.0159 1.0719 1.0582 0.041 Uiso 1 1 calc R . .
H12B H -0.0006 0.9058 1.0144 0.041 Uiso 1 1 calc R . .
H12C H -0.1602 1.0233 1.0236 0.041 Uiso 1 1 calc R . .
C13 C -0.0303(5) 1.2953(5) 0.9581(2) 0.0221(11) Uani 1 1 d . . .
H13A H 0.0024 1.3519 0.9151 0.033 Uiso 1 1 calc R . .
H13B H 0.0316 1.3420 0.9976 0.033 Uiso 1 1 calc R . .
H13C H -0.1513 1.3089 0.9657 0.033 Uiso 1 1 calc R . .
C10 C -0.3006(4) 0.8233(5) 0.70473(17) 0.0158(9) Uani 1 1 d . . .
H10A H -0.4194 0.8449 0.6947 0.024 Uiso 1 1 calc R . .
H10B H -0.2712 0.7131 0.6885 0.024 Uiso 1 1 calc R . .
H10C H -0.2308 0.9044 0.6806 0.024 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
Br 0.01358(17) 0.0283(2) 0.0328(2) -0.0044(3) -0.0056(2) 0.0059(2)
O7 0.0129(16) 0.0107(16) 0.0190(18) -0.0019(13) 0.0015(12) 0.0025(12)
C6 0.014(2) 0.008(2) 0.018(2) 0.004(2) 0.0002(17) 0.003(2)
C5 0.0099(18) 0.015(2) 0.017(2) 0.004(2) 0.0048(19) 0.0033(15)
C4 0.017(2) 0.010(2) 0.010(2) 0.002(2) 0.000(2) -0.0004(16)
C3 0.014(2) 0.0106(18) 0.015(2) -0.001(2) -0.003(2) -0.0023(17)
C2 0.011(2) 0.014(2) 0.014(3) 0.0007(19) -0.0006(17) 0.0015(18)
C1 0.0072(18) 0.008(2) 0.0155(19) 0.0013(17) 0.0021(16) -0.003(2)
C9 0.0105(19) 0.013(2) 0.017(2) -0.009(3) 0.0011(16) 0.001(2)
O8 0.026(2) 0.0110(15) 0.0271(17) 0.0017(13) -0.0031(14) -0.0008(14)
C8 0.015(2) 0.019(2) 0.007(2) 0.0018(19) -0.0030(19) -0.002(2)
C11 0.015(2) 0.017(2) 0.013(2) -0.002(2) -0.0048(18) -0.0022(19)
C12 0.038(3) 0.029(3) 0.015(3) 0.004(2) -0.006(2) 0.001(2)
C13 0.024(2) 0.020(3) 0.023(3) -0.005(3) 0.0001(19) -0.003(2)
C10 0.017(2) 0.015(2) 0.015(2) -0.004(2) 0.0026(17) 0.000(2)
_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
Br C5 1.973(3) . ?
O7 C8 1.366(5) . ?
O7 C6 1.482(5) . ?
C6 C5 1.531(6) . ?
C6 C1 1.547(5) . ?
C6 H6A 1.0000 . ?
C5 C4 1.527(5) . ?
C5 H5A 1.0000 . ?
C4 C3 1.544(5) . ?
C4 C11 1.548(5) . ?
C4 H4A 1.0000 . ?
C3 C2 1.531(5) . ?
C3 H3A 0.9900 . ?
C3 H3E 0.9900 . ?
C2 C1 1.531(5) . ?
C2 H2A 0.9900 . ?
C2 H2E 0.9900 . ?
C1 C9 1.529(5) . ?
C1 C10 1.540(5) . ?
C9 C8 1.493(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O8 C8 1.203(4) . ?
C11 C12 1.527(6) . ?
C11 C13 1.537(5) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C8 O7 C6 109.4(3) . . ?
O7 C6 C5 108.0(3) . . ?
O7 C6 C1 103.2(3) . . ?
C5 C6 C1 114.8(3) . . ?
O7 C6 H6A 110.2 . . ?
C5 C6 H6A 110.2 . . ?
C1 C6 H6A 110.2 . . ?
C4 C5 C6 112.1(3) . . ?
C4 C5 Br 113.2(2) . . ?
C6 C5 Br 107.6(2) . . ?
C4 C5 H5A 107.9 . . ?
C6 C5 H5A 107.9 . . ?
Br C5 H5A 107.9 . . ?
C5 C4 C3 105.8(3) . . ?
C5 C4 C11 114.3(3) . . ?
C3 C4 C11 114.1(3) . . ?
C5 C4 H4A 107.4 . . ?
C3 C4 H4A 107.4 . . ?
C11 C4 H4A 107.4 . . ?
C2 C3 C4 110.3(3) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3E 109.6 . . ?
C4 C3 H3E 109.6 . . ?
H3A C3 H3E 108.1 . . ?
C3 C2 C1 114.0(3) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2E 108.8 . . ?
C1 C2 H2E 108.8 . . ?
H2A C2 H2E 107.7 . . ?
C9 C1 C2 114.9(3) . . ?
C9 C1 C10 109.7(3) . . ?
C2 C1 C10 109.3(3) . . ?
C9 C1 C6 100.7(3) . . ?
C2 C1 C6 112.3(3) . . ?
C10 C1 C6 109.6(3) . . ?
C8 C9 C1 103.1(3) . . ?
C8 C9 H9A 111.1 . . ?
C1 C9 H9A 111.1 . . ?
C8 C9 H9B 111.1 . . ?
C1 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
O8 C8 O7 120.3(4) . . ?
O8 C8 C9 129.7(4) . . ?
O7 C8 C9 110.0(3) . . ?
C12 C11 C13 110.8(4) . . ?
C12 C11 C4 113.5(3) . . ?
C13 C11 C4 110.8(3) . . ?
C12 C11 H11 107.2 . . ?
C13 C11 H11 107.2 . . ?
C4 C11 H11 107.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C8 O7 C6 C5 98.8(3) . . . . ?
C8 O7 C6 C1 -23.1(4) . . . . ?
O7 C6 C5 C4 -166.1(3) . . . . ?
C1 C6 C5 C4 -51.5(5) . . . . ?
O7 C6 C5 Br 68.8(3) . . . . ?
C1 C6 C5 Br -176.6(3) . . . . ?
C6 C5 C4 C3 61.9(4) . . . . ?
Br C5 C4 C3 -176.2(3) . . . . ?
C6 C5 C4 C11 -171.8(3) . . . . ?
Br C5 C4 C11 -49.8(4) . . . . ?
C5 C4 C3 C2 -64.5(4) . . . . ?
C11 C4 C3 C2 169.0(3) . . . . ?
C4 C3 C2 C1 57.2(4) . . . . ?
C3 C2 C1 C9 71.1(4) . . . . ?
C3 C2 C1 C10 -165.1(3) . . . . ?
C3 C2 C1 C6 -43.3(4) . . . . ?
O7 C6 C1 C9 34.7(4) . . . . ?
C5 C6 C1 C9 -82.5(4) . . . . ?
O7 C6 C1 C2 157.4(3) . . . . ?
C5 C6 C1 C2 40.2(5) . . . . ?
O7 C6 C1 C10 -80.8(4) . . . . ?
C5 C6 C1 C10 161.9(3) . . . . ?
C2 C1 C9 C8 -154.8(3) . . . . ?
C10 C1 C9 C8 81.5(3) . . . . ?
C6 C1 C9 C8 -33.9(4) . . . . ?
C6 O7 C8 O8 -178.8(3) . . . . ?
C6 O7 C8 C9 1.0(4) . . . . ?
C1 C9 C8 O8 -158.4(4) . . . . ?
C1 C9 C8 O7 21.8(4) . . . . ?
C5 C4 C11 C12 -58.4(5) . . . . ?
C3 C4 C11 C12 63.5(4) . . . . ?
C5 C4 C11 C13 176.2(3) . . . . ?
C3 C4 C11 C13 -61.9(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 26.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.601
_refine_diff_density_min -0.452
_refine_diff_density_rms 0.085
#===== end
data_(+/-)-9c
_database_code_depnum_ccdc_archive 'CCDC 825648'
#TrackingRef 'OBC-Synthesis-of-piperitone-derived-halogenated-lactones.cif.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(+/-)-c-5-iodo-c-4-isopropyl-r
-1-methyl-7-oxa-cis-bicyclo[4.3.0]nonan-8-one
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H19 I O2'
_chemical_formula_sum 'C12 H19 I O2'
_chemical_formula_weight 322.17
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
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 17.517(3)
_cell_length_b 10.774(2)
_cell_length_c 6.906(2)
_cell_angle_alpha 90.00
_cell_angle_beta 97.60(3)
_cell_angle_gamma 90.00
_cell_volume 1291.9(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 1264
_cell_measurement_theta_min 3.01
_cell_measurement_theta_max 27
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_min 0.30
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.656
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 640
_exptl_absorpt_coefficient_mu 2.460
_exptl_absorpt_correction_type NONE
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 8922
_diffrn_reflns_av_R_equivalents 0.1144
_diffrn_reflns_av_sigmaI/netI 0.0659
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_theta_min 3.01
_diffrn_reflns_theta_max 27.00
_reflns_number_total 2801
_reflns_number_gt 2465
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0695P)^2^+0.0000P] 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 2801
_refine_ls_number_parameters 136
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0435
_refine_ls_R_factor_gt 0.0390
_refine_ls_wR_factor_ref 0.1058
_refine_ls_wR_factor_gt 0.1035
_refine_ls_goodness_of_fit_ref 1.012
_refine_ls_restrained_S_all 1.012
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
I I 0.326636(12) 0.429463(19) 0.18624(3) 0.02130(12) Uani 1 1 d . . .
C6 C 0.19732(18) 0.3964(3) -0.1448(5) 0.0150(6) Uani 1 1 d . . .
H6E H 0.1866 0.3340 -0.0448 0.018 Uiso 1 1 calc R . .
C5 C 0.2834(2) 0.4200(3) -0.1270(5) 0.0139(7) Uani 1 1 d . . .
H5E H 0.3075 0.3458 -0.1815 0.017 Uiso 1 1 calc R . .
C4 C 0.30642(17) 0.5337(3) -0.2376(5) 0.0137(6) Uani 1 1 d . . .
H4A H 0.2910 0.5154 -0.3793 0.016 Uiso 1 1 calc R . .
C3 C 0.25793(18) 0.6459(3) -0.1905(5) 0.0168(6) Uani 1 1 d . . .
H3A H 0.2680 0.6640 -0.0489 0.020 Uiso 1 1 calc R . .
H3E H 0.2731 0.7196 -0.2620 0.020 Uiso 1 1 calc R . .
C2 C 0.17195(18) 0.6205(3) -0.2482(6) 0.0178(6) Uani 1 1 d . . .
H2A H 0.1621 0.6044 -0.3905 0.021 Uiso 1 1 calc R . .
H2E H 0.1424 0.6954 -0.2209 0.021 Uiso 1 1 calc R . .
C1 C 0.14259(18) 0.5088(3) -0.1385(5) 0.0164(7) Uani 1 1 d . . .
C9 C 0.06962(19) 0.4553(3) -0.2574(6) 0.0198(7) Uani 1 1 d . . .
H9A H 0.0387 0.4079 -0.1727 0.024 Uiso 1 1 calc R . .
H9B H 0.0373 0.5221 -0.3238 0.024 Uiso 1 1 calc R . .
C8 C 0.10037(18) 0.3714(3) -0.4036(5) 0.0190(7) Uani 1 1 d . . .
O8 O 0.06829(14) 0.3299(2) -0.5549(4) 0.0259(6) Uani 1 1 d . . .
O7 O 0.17549(12) 0.3447(2) -0.3413(3) 0.0175(5) Uani 1 1 d . . .
C11 C 0.39419(19) 0.5583(3) -0.2131(5) 0.0159(7) Uani 1 1 d . . .
H11 H 0.4105 0.5854 -0.0753 0.019 Uiso 1 1 calc R . .
C12 C 0.4151(2) 0.6617(3) -0.3488(5) 0.0231(7) Uani 1 1 d . . .
H12A H 0.4710 0.6747 -0.3289 0.035 Uiso 1 1 calc R . .
H12B H 0.3890 0.7386 -0.3196 0.035 Uiso 1 1 calc R . .
H12C H 0.3987 0.6378 -0.4849 0.035 Uiso 1 1 calc R . .
C13 C 0.4395(2) 0.4404(3) -0.2491(6) 0.0221(8) Uani 1 1 d . . .
H13A H 0.4947 0.4592 -0.2320 0.033 Uiso 1 1 calc R . .
H13B H 0.4236 0.4108 -0.3825 0.033 Uiso 1 1 calc R . .
H13C H 0.4290 0.3761 -0.1558 0.033 Uiso 1 1 calc R . .
C10 C 0.1284(2) 0.5443(4) 0.0688(6) 0.0254(8) Uani 1 1 d . . .
H10A H 0.1102 0.4714 0.1342 0.038 Uiso 1 1 calc R . .
H10B H 0.0894 0.6100 0.0621 0.038 Uiso 1 1 calc R . .
H10C H 0.1765 0.5741 0.1427 0.038 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
I 0.02812(17) 0.02004(17) 0.01404(18) 0.00494(7) -0.00356(11) -0.00707(8)
C6 0.0192(15) 0.0124(14) 0.0127(16) -0.0013(12) -0.0005(13) 0.0001(13)
C5 0.0188(15) 0.0129(15) 0.0088(16) -0.0017(11) -0.0022(12) -0.0003(11)
C4 0.0184(15) 0.0133(14) 0.0093(15) 0.0019(12) 0.0011(12) 0.0011(12)
C3 0.0204(15) 0.0106(14) 0.0198(17) 0.0014(12) 0.0044(13) -0.0016(12)
C2 0.0188(15) 0.0115(15) 0.0235(17) 0.0037(14) 0.0045(13) 0.0030(12)
C1 0.0179(15) 0.0135(15) 0.0185(18) -0.0011(12) 0.0044(13) -0.0003(12)
C9 0.0176(16) 0.0187(15) 0.023(2) -0.0011(15) 0.0024(14) 0.0047(13)
C8 0.0194(15) 0.0129(15) 0.0239(19) 0.0005(13) -0.0002(14) 0.0017(12)
O8 0.0259(12) 0.0236(13) 0.0254(14) -0.0059(11) -0.0073(11) 0.0011(10)
O7 0.0178(11) 0.0149(11) 0.0185(12) -0.0059(9) -0.0017(9) 0.0033(9)
C11 0.0174(15) 0.0155(15) 0.0153(17) -0.0020(12) 0.0033(13) -0.0008(12)
C12 0.0257(17) 0.0234(17) 0.0213(18) 0.0001(14) 0.0069(14) -0.0033(14)
C13 0.0164(15) 0.0221(18) 0.027(2) -0.0036(14) 0.0009(14) 0.0021(13)
C10 0.0272(18) 0.0253(18) 0.026(2) -0.0081(16) 0.0118(16) -0.0024(15)
_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
I C5 2.198(4) . ?
C6 O7 1.470(4) . ?
C6 C5 1.517(5) . ?
C6 C1 1.549(4) . ?
C6 H6E 1.0000 . ?
C5 C4 1.526(4) . ?
C5 H5E 1.0000 . ?
C4 C3 1.537(4) . ?
C4 C11 1.547(4) . ?
C4 H4A 1.0000 . ?
C3 C2 1.531(4) . ?
C3 H3A 0.9900 . ?
C3 H3E 0.9900 . ?
C2 C1 1.546(5) . ?
C2 H2A 0.9900 . ?
C2 H2E 0.9900 . ?
C1 C10 1.533(5) . ?
C1 C9 1.537(5) . ?
C9 C8 1.507(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 O8 1.205(4) . ?
C8 O7 1.360(4) . ?
C11 C12 1.531(5) . ?
C11 C13 1.535(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
O7 C6 C5 105.8(3) . . ?
O7 C6 C1 103.7(2) . . ?
C5 C6 C1 118.6(3) . . ?
O7 C6 H6E 109.4 . . ?
C5 C6 H6E 109.4 . . ?
C1 C6 H6E 109.4 . . ?
C6 C5 C4 114.8(3) . . ?
C6 C5 I 107.3(2) . . ?
C4 C5 I 112.1(2) . . ?
C6 C5 H5E 107.5 . . ?
C4 C5 H5E 107.5 . . ?
I C5 H5E 107.5 . . ?
C5 C4 C3 109.6(3) . . ?
C5 C4 C11 114.1(3) . . ?
C3 C4 C11 114.3(3) . . ?
C5 C4 H4A 106.1 . . ?
C3 C4 H4A 106.1 . . ?
C11 C4 H4A 106.1 . . ?
C2 C3 C4 110.9(3) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3E 109.5 . . ?
C4 C3 H3E 109.5 . . ?
H3A C3 H3E 108.0 . . ?
C3 C2 C1 113.0(3) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2E 109.0 . . ?
C1 C2 H2E 109.0 . . ?
H2A C2 H2E 107.8 . . ?
C10 C1 C9 111.5(3) . . ?
C10 C1 C2 111.7(3) . . ?
C9 C1 C2 109.7(3) . . ?
C10 C1 C6 113.5(3) . . ?
C9 C1 C6 99.5(3) . . ?
C2 C1 C6 110.3(3) . . ?
C8 C9 C1 103.7(3) . . ?
C8 C9 H9A 111.0 . . ?
C1 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C1 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
O8 C8 O7 121.1(3) . . ?
O8 C8 C9 129.6(3) . . ?
O7 C8 C9 109.4(3) . . ?
C8 O7 C6 109.5(2) . . ?
C12 C11 C13 109.4(3) . . ?
C12 C11 C4 111.9(3) . . ?
C13 C11 C4 111.6(3) . . ?
C12 C11 H11 108.0 . . ?
C13 C11 H11 108.0 . . ?
C4 C11 H11 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O7 C6 C5 C4 75.5(3) . . . . ?
C1 C6 C5 C4 -40.2(4) . . . . ?
O7 C6 C5 I -159.20(18) . . . . ?
C1 C6 C5 I 85.0(3) . . . . ?
C6 C5 C4 C3 48.8(4) . . . . ?
I C5 C4 C3 -73.9(3) . . . . ?
C6 C5 C4 C11 178.4(3) . . . . ?
I C5 C4 C11 55.7(3) . . . . ?
C5 C4 C3 C2 -59.3(4) . . . . ?
C11 C4 C3 C2 171.2(3) . . . . ?
C4 C3 C2 C1 60.8(4) . . . . ?
C3 C2 C1 C10 79.4(4) . . . . ?
C3 C2 C1 C9 -156.4(3) . . . . ?
C3 C2 C1 C6 -47.8(4) . . . . ?
O7 C6 C1 C10 155.0(3) . . . . ?
C5 C6 C1 C10 -88.1(4) . . . . ?
O7 C6 C1 C9 36.4(3) . . . . ?
C5 C6 C1 C9 153.3(3) . . . . ?
O7 C6 C1 C2 -78.8(3) . . . . ?
C5 C6 C1 C2 38.1(4) . . . . ?
C10 C1 C9 C8 -152.9(3) . . . . ?
C2 C1 C9 C8 82.9(3) . . . . ?
C6 C1 C9 C8 -32.9(3) . . . . ?
C1 C9 C8 O8 -161.6(4) . . . . ?
C1 C9 C8 O7 18.4(4) . . . . ?
O8 C8 O7 C6 -174.2(3) . . . . ?
C9 C8 O7 C6 5.8(3) . . . . ?
C5 C6 O7 C8 -153.0(3) . . . . ?
C1 C6 O7 C8 -27.5(3) . . . . ?
C5 C4 C11 C12 172.0(3) . . . . ?
C3 C4 C11 C12 -60.8(4) . . . . ?
C5 C4 C11 C13 49.1(4) . . . . ?
C3 C4 C11 C13 176.3(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full 27.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max 2.281
_refine_diff_density_min -1.585
_refine_diff_density_rms 0.165
#==== end
data_(+/-)-10c
_database_code_depnum_ccdc_archive 'CCDC 825649'
#TrackingRef 'OBC-Synthesis-of-piperitone-derived-halogenated-lactones.cif.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(+/-)-c-5-bromo-c-4-isopropyl-r
-1-methyl-7-oxa-cis-bicyclo[4.3.0]nonan-8-one
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H19 Br O2'
_chemical_formula_sum 'C12 H19 Br O2'
_chemical_formula_weight 275.18
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
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 17.359(3)
_cell_length_b 10.889(2)
_cell_length_c 6.611(2)
_cell_angle_alpha 90.00
_cell_angle_beta 99.36(3)
_cell_angle_gamma 90.00
_cell_volume 1233.0(5)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 11370
_cell_measurement_theta_min 3.02
_cell_measurement_theta_max 36.83
_exptl_crystal_description colorless
_exptl_crystal_colour block
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.482
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 568
_exptl_absorpt_coefficient_mu 3.314
_exptl_absorpt_correction_T_min 0.51543
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 18725
_diffrn_reflns_av_R_equivalents 0.0284
_diffrn_reflns_av_sigmaI/netI 0.0241
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_theta_min 3.03
_diffrn_reflns_theta_max 32.00
_reflns_number_total 4232
_reflns_number_gt 3373
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0369P)^2^+0.0000P] 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 4232
_refine_ls_number_parameters 136
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0338
_refine_ls_R_factor_gt 0.0234
_refine_ls_wR_factor_ref 0.0577
_refine_ls_wR_factor_gt 0.0557
_refine_ls_goodness_of_fit_ref 0.964
_refine_ls_restrained_S_all 0.964
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
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
Br Br 0.335508(7) 0.080805(11) 0.178511(17) 0.02388(5) Uani 1 1 d . . .
C1 C 0.14712(7) -0.00468(10) -0.09233(18) 0.0176(2) Uani 1 1 d . . .
C2 C 0.17271(7) -0.11379(11) -0.2142(2) 0.0211(2) Uani 1 1 d . . .
H2A H 0.1457 -0.1889 -0.1788 0.025 Uiso 1 1 calc R . .
H2E H 0.1564 -0.0982 -0.3625 0.025 Uiso 1 1 calc R . .
C3 C 0.26077(7) -0.13594(10) -0.17181(19) 0.0198(2) Uani 1 1 d . . .
H3E H 0.2735 -0.2085 -0.2505 0.024 Uiso 1 1 calc R . .
H3A H 0.2772 -0.1537 -0.0242 0.024 Uiso 1 1 calc R . .
C4 C 0.30595(6) -0.02425(10) -0.23138(17) 0.0159(2) Uani 1 1 d . . .
H4A H 0.2858 -0.0076 -0.3793 0.019 Uiso 1 1 calc R . .
C5 C 0.28554(7) 0.08827(10) -0.11303(17) 0.0162(2) Uani 1 1 d . . .
H5E H 0.3061 0.1624 -0.1758 0.019 Uiso 1 1 calc R . .
C6 C 0.19867(7) 0.10792(10) -0.11334(17) 0.0161(2) Uani 1 1 d . . .
H6E H 0.1916 0.1694 -0.0055 0.019 Uiso 1 1 calc R . .
O7 O 0.16730(5) 0.15823(7) -0.31549(13) 0.02074(17) Uani 1 1 d . . .
C8 C 0.09030(7) 0.12871(11) -0.3637(2) 0.0215(2) Uani 1 1 d . . .
O8 O 0.05128(6) 0.16794(9) -0.51667(15) 0.0299(2) Uani 1 1 d . . .
C9 C 0.06839(7) 0.04488(11) -0.2006(2) 0.0218(2) Uani 1 1 d . . .
H9A H 0.0343 -0.0227 -0.2623 0.026 Uiso 1 1 calc R . .
H9B H 0.0412 0.0908 -0.1038 0.026 Uiso 1 1 calc R . .
C10 C 0.14467(8) -0.03970(13) 0.1304(2) 0.0265(3) Uani 1 1 d . . .
H10A H 0.1959 -0.0708 0.1938 0.040 Uiso 1 1 calc R . .
H10B H 0.1052 -0.1035 0.1346 0.040 Uiso 1 1 calc R . .
H10C H 0.1314 0.0328 0.2056 0.040 Uiso 1 1 calc R . .
C11 C 0.39432(7) -0.04606(11) -0.21502(18) 0.0187(2) Uani 1 1 d . . .
H11A H 0.4147 -0.0722 -0.0712 0.022 Uiso 1 1 calc R . .
C12 C 0.41250(8) -0.14867(12) -0.3585(2) 0.0246(3) Uani 1 1 d . . .
H12A H 0.4691 -0.1601 -0.3433 0.037 Uiso 1 1 calc R . .
H12B H 0.3919 -0.1264 -0.5006 0.037 Uiso 1 1 calc R . .
H12C H 0.3881 -0.2252 -0.3234 0.037 Uiso 1 1 calc R . .
C13 C 0.43794(8) 0.07104(11) -0.2582(2) 0.0245(3) Uani 1 1 d . . .
H13A H 0.4939 0.0533 -0.2461 0.037 Uiso 1 1 calc R . .
H13B H 0.4298 0.1346 -0.1590 0.037 Uiso 1 1 calc R . .
H13C H 0.4181 0.1000 -0.3973 0.037 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
Br 0.02435(7) 0.02858(7) 0.01675(6) -0.00646(5) -0.00253(4) 0.00568(5)
C1 0.0178(5) 0.0147(5) 0.0215(6) 0.0011(4) 0.0063(4) 0.0007(4)
C2 0.0202(6) 0.0145(5) 0.0300(6) -0.0033(4) 0.0081(5) -0.0025(4)
C3 0.0207(6) 0.0137(5) 0.0264(6) -0.0023(4) 0.0081(4) -0.0001(4)
C4 0.0167(5) 0.0170(5) 0.0144(5) -0.0003(4) 0.0035(4) -0.0007(4)
C5 0.0175(5) 0.0151(5) 0.0151(5) 0.0004(4) 0.0003(4) -0.0007(4)
C6 0.0173(5) 0.0143(5) 0.0164(5) 0.0000(4) 0.0016(4) 0.0013(4)
O7 0.0200(4) 0.0186(4) 0.0221(4) 0.0060(3) -0.0010(3) -0.0017(3)
C8 0.0205(6) 0.0170(5) 0.0255(6) -0.0007(4) 0.0000(4) -0.0005(4)
O8 0.0277(5) 0.0288(5) 0.0290(5) 0.0041(4) -0.0079(4) 0.0006(4)
C9 0.0169(5) 0.0183(5) 0.0302(6) 0.0011(5) 0.0045(5) -0.0006(4)
C10 0.0261(6) 0.0289(6) 0.0273(7) 0.0091(5) 0.0123(5) 0.0071(5)
C11 0.0168(5) 0.0224(5) 0.0169(5) -0.0005(4) 0.0031(4) 0.0001(4)
C12 0.0223(6) 0.0285(6) 0.0245(6) -0.0028(5) 0.0088(5) 0.0028(5)
C13 0.0182(6) 0.0300(7) 0.0255(6) 0.0008(5) 0.0039(4) -0.0043(5)
_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
Br C5 1.9824(13) . ?
C1 C10 1.5282(18) . ?
C1 C9 1.5338(17) . ?
C1 C6 1.5375(16) . ?
C1 C2 1.5410(17) . ?
C2 C3 1.5277(17) . ?
C2 H2A 0.9900 . ?
C2 H2E 0.9900 . ?
C3 C4 1.5329(16) . ?
C3 H3E 0.9900 . ?
C3 H3A 0.9900 . ?
C4 C5 1.5261(15) . ?
C4 C11 1.5386(16) . ?
C4 H4A 1.0000 . ?
C5 C6 1.5228(16) . ?
C5 H5E 1.0000 . ?
C6 O7 1.4649(14) . ?
C6 H6E 1.0000 . ?
O7 C8 1.3613(15) . ?
C8 O8 1.2003(15) . ?
C8 C9 1.5083(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5313(17) . ?
C11 C13 1.5333(17) . ?
C11 H11A 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C10 C1 C9 112.03(10) . . ?
C10 C1 C6 113.19(11) . . ?
C9 C1 C6 99.49(9) . . ?
C10 C1 C2 111.52(10) . . ?
C9 C1 C2 109.76(10) . . ?
C6 C1 C2 110.25(10) . . ?
C3 C2 C1 113.00(10) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2E 109.0 . . ?
C1 C2 H2E 109.0 . . ?
H2A C2 H2E 107.8 . . ?
C2 C3 C4 111.48(10) . . ?
C2 C3 H3E 109.3 . . ?
C4 C3 H3E 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
H3E C3 H3A 108.0 . . ?
C5 C4 C3 109.52(9) . . ?
C5 C4 C11 113.57(9) . . ?
C3 C4 C11 113.92(9) . . ?
C5 C4 H4A 106.4 . . ?
C3 C4 H4A 106.4 . . ?
C11 C4 H4A 106.4 . . ?
C6 C5 C4 115.13(9) . . ?
C6 C5 Br 106.48(8) . . ?
C4 C5 Br 111.36(7) . . ?
C6 C5 H5E 107.9 . . ?
C4 C5 H5E 107.9 . . ?
Br C5 H5E 107.9 . . ?
O7 C6 C5 105.95(9) . . ?
O7 C6 C1 104.19(9) . . ?
C5 C6 C1 118.60(9) . . ?
O7 C6 H6E 109.2 . . ?
C5 C6 H6E 109.2 . . ?
C1 C6 H6E 109.2 . . ?
C8 O7 C6 109.30(9) . . ?
O8 C8 O7 120.75(12) . . ?
O8 C8 C9 130.13(12) . . ?
O7 C8 C9 109.12(10) . . ?
C8 C9 C1 103.73(10) . . ?
C8 C9 H9A 111.0 . . ?
C1 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C1 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C13 109.49(10) . . ?
C12 C11 C4 111.88(10) . . ?
C13 C11 C4 112.05(10) . . ?
C12 C11 H11A 107.7 . . ?
C13 C11 H11A 107.7 . . ?
C4 C11 H11A 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C10 C1 C2 C3 -78.15(13) . . . . ?
C9 C1 C2 C3 157.09(10) . . . . ?
C6 C1 C2 C3 48.48(14) . . . . ?
C1 C2 C3 C4 -60.84(13) . . . . ?
C2 C3 C4 C5 58.07(13) . . . . ?
C2 C3 C4 C11 -173.52(10) . . . . ?
C3 C4 C5 C6 -47.37(13) . . . . ?
C11 C4 C5 C6 -175.97(9) . . . . ?
C3 C4 C5 Br 73.95(10) . . . . ?
C11 C4 C5 Br -54.65(11) . . . . ?
C4 C5 C6 O7 -76.63(11) . . . . ?
Br C5 C6 O7 159.44(7) . . . . ?
C4 C5 C6 C1 39.88(14) . . . . ?
Br C5 C6 C1 -84.05(10) . . . . ?
C10 C1 C6 O7 -155.56(9) . . . . ?
C9 C1 C6 O7 -36.53(11) . . . . ?
C2 C1 C6 O7 78.75(11) . . . . ?
C10 C1 C6 C5 87.00(13) . . . . ?
C9 C1 C6 C5 -153.97(10) . . . . ?
C2 C1 C6 C5 -38.69(14) . . . . ?
C5 C6 O7 C8 153.30(9) . . . . ?
C1 C6 O7 C8 27.44(11) . . . . ?
C6 O7 C8 O8 174.72(11) . . . . ?
C6 O7 C8 C9 -5.56(13) . . . . ?
O8 C8 C9 C1 161.18(14) . . . . ?
O7 C8 C9 C1 -18.51(13) . . . . ?
C10 C1 C9 C8 152.78(11) . . . . ?
C6 C1 C9 C8 32.89(11) . . . . ?
C2 C1 C9 C8 -82.76(12) . . . . ?
C5 C4 C11 C12 -172.22(10) . . . . ?
C3 C4 C11 C12 61.46(13) . . . . ?
C5 C4 C11 C13 -48.81(13) . . . . ?
C3 C4 C11 C13 -175.13(10) . . . . ?
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full 32.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max 0.713
_refine_diff_density_min -0.212
_refine_diff_density_rms 0.074
#===== end
data_(+/-)-11c
_database_code_depnum_ccdc_archive 'CCDC 825650'
#TrackingRef 'OBC-Synthesis-of-piperitone-derived-halogenated-lactones.cif.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(+/-)-c-5-chloro-c-4-isopropyl-r-1-methyl-7
-oxa-cis-bicyclo[4.3.0]nonan-8-one
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C12 H19 Cl O2'
_chemical_formula_sum 'C12 H19 Cl O2'
_chemical_formula_weight 230.72
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
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 6.566(2)
_cell_length_b 10.890(3)
_cell_length_c 33.558(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.60(3)
_cell_angle_gamma 90.00
_cell_volume 2399.4(10)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 1886
_cell_measurement_theta_min 3.07
_cell_measurement_theta_max 27.00
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.40
_exptl_crystal_size_min 0.40
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.277
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 992
_exptl_absorpt_coefficient_mu 0.298
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 100(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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 12324
_diffrn_reflns_av_R_equivalents 0.0261
_diffrn_reflns_av_sigmaI/netI 0.0266
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -39
_diffrn_reflns_limit_l_max 38
_diffrn_reflns_theta_min 3.07
_diffrn_reflns_theta_max 25.00
_reflns_number_total 4049
_reflns_number_gt 3362
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_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^)+(0.0489P)^2^+0.6980P] 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 4049
_refine_ls_number_parameters 271
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0467
_refine_ls_R_factor_gt 0.0368
_refine_ls_wR_factor_ref 0.0944
_refine_ls_wR_factor_gt 0.0912
_refine_ls_goodness_of_fit_ref 1.083
_refine_ls_restrained_S_all 1.083
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
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
Cl1 Cl 1.51106(7) 0.54875(4) 0.170554(14) 0.02630(14) Uani 1 1 d . . .
C6 C 1.3123(3) 0.58855(16) 0.10160(5) 0.0189(4) Uani 1 1 d . . .
H6E H 1.4276 0.6482 0.0996 0.023 Uiso 1 1 calc R . .
C5 C 1.2667(3) 0.56610(16) 0.14531(5) 0.0188(4) Uani 1 1 d . . .
H5E H 1.1989 0.6411 0.1561 0.023 Uiso 1 1 calc R . .
C4 C 1.1290(3) 0.45608(16) 0.15329(5) 0.0180(4) Uani 1 1 d . . .
H4A H 0.9921 0.4773 0.1419 0.022 Uiso 1 1 calc R . .
C3 C 1.2049(3) 0.34434(16) 0.12993(5) 0.0220(4) Uani 1 1 d . . .
H3A H 1.3425 0.3215 0.1397 0.026 Uiso 1 1 calc R . .
H3E H 1.1129 0.2739 0.1347 0.026 Uiso 1 1 calc R . .
C2 C 1.2134(3) 0.37056(16) 0.08524(5) 0.0231(4) Uani 1 1 d . . .
H2A H 1.0741 0.3894 0.0754 0.028 Uiso 1 1 calc R . .
H2E H 1.2602 0.2957 0.0713 0.028 Uiso 1 1 calc R . .
C1 C 1.3550(3) 0.47780(16) 0.07446(5) 0.0197(4) Uani 1 1 d . . .
C9 C 1.2901(3) 0.53313(17) 0.03431(5) 0.0231(4) Uani 1 1 d . . .
H9A H 1.4035 0.5793 0.0222 0.028 Uiso 1 1 calc R . .
H9B H 1.2443 0.4683 0.0156 0.028 Uiso 1 1 calc R . .
C8 C 1.1184(3) 0.61695(17) 0.04469(6) 0.0236(4) Uani 1 1 d . . .
O8 O 0.9835(2) 0.65865(12) 0.02416(4) 0.0307(3) Uani 1 1 d . . .
O7 O 1.12881(18) 0.64393(11) 0.08436(4) 0.0223(3) Uani 1 1 d . . .
C11 C 1.0975(3) 0.43196(17) 0.19806(5) 0.0210(4) Uani 1 1 d . . .
H11 H 1.2310 0.4047 0.2097 0.025 Uiso 1 1 calc R . .
C12 C 0.9424(3) 0.32971(18) 0.20538(6) 0.0271(4) Uani 1 1 d . . .
H12A H 0.9279 0.3169 0.2341 0.041 Uiso 1 1 calc R . .
H12B H 0.9895 0.2536 0.1929 0.041 Uiso 1 1 calc R . .
H12C H 0.8104 0.3532 0.1938 0.041 Uiso 1 1 calc R . .
C13 C 1.0332(3) 0.54816(17) 0.22007(6) 0.0248(4) Uani 1 1 d . . .
H13A H 1.1331 0.6133 0.2154 0.037 Uiso 1 1 calc R . .
H13B H 1.0259 0.5311 0.2487 0.037 Uiso 1 1 calc R . .
H13C H 0.8992 0.5747 0.2102 0.037 Uiso 1 1 calc R . .
C10 C 1.5783(3) 0.43850(18) 0.07500(6) 0.0275(5) Uani 1 1 d . . .
H10A H 1.6643 0.5089 0.0683 0.041 Uiso 1 1 calc R . .
H10B H 1.5986 0.3730 0.0554 0.041 Uiso 1 1 calc R . .
H10C H 1.6153 0.4084 0.1016 0.041 Uiso 1 1 calc R . .
cl2 Cl 0.02378(7) 0.37798(4) 0.331914(14) 0.02634(14) Uani 1 1 d . . .
C06 C 0.2112(3) 0.36471(16) 0.40323(5) 0.0181(4) Uani 1 1 d . . .
H06E H 0.1012 0.3019 0.4061 0.022 Uiso 1 1 calc R . .
C05 C 0.2646(3) 0.37661(16) 0.35938(5) 0.0190(4) Uani 1 1 d . . .
H05E H 0.3422 0.3017 0.3514 0.023 Uiso 1 1 calc R . .
C04 C 0.3914(3) 0.48914(16) 0.34891(5) 0.0184(4) Uani 1 1 d . . .
H04A H 0.5282 0.4768 0.3617 0.022 Uiso 1 1 calc R . .
C03 C 0.2993(3) 0.60315(16) 0.36836(5) 0.0221(4) Uani 1 1 d . . .
H03E H 0.3843 0.6756 0.3621 0.027 Uiso 1 1 calc R . .
H03A H 0.1614 0.6176 0.3571 0.027 Uiso 1 1 calc R . .
C02 C 0.2849(3) 0.58931(17) 0.41351(5) 0.0229(4) Uani 1 1 d . . .
H02E H 0.2283 0.6659 0.4248 0.027 Uiso 1 1 calc R . .
H02A H 0.4237 0.5782 0.4248 0.027 Uiso 1 1 calc R . .
C01 C 0.1517(3) 0.48084(16) 0.42632(5) 0.0194(4) Uani 1 1 d . . .
C09 C 0.2125(3) 0.44006(17) 0.46874(5) 0.0216(4) Uani 1 1 d . . .
H09A H 0.2504 0.5116 0.4855 0.026 Uiso 1 1 calc R . .
H09B H 0.0997 0.3952 0.4816 0.026 Uiso 1 1 calc R . .
C08 C 0.3917(3) 0.35761(17) 0.46247(6) 0.0238(4) Uani 1 1 d . . .
O08 O 0.5204(2) 0.32373(13) 0.48575(4) 0.0331(4) Uani 1 1 d . . .
O07 O 0.39560(18) 0.32091(11) 0.42363(4) 0.0226(3) Uani 1 1 d . . .
C011 C 0.4283(3) 0.50334(17) 0.30389(5) 0.0222(4) Uani 1 1 d . . .
H011 H 0.2955 0.5263 0.2911 0.027 Uiso 1 1 calc R . .
C012 C 0.5802(3) 0.60623(19) 0.29523(6) 0.0296(5) Uani 1 1 d . . .
H12F H 0.5991 0.6131 0.2664 0.044 Uiso 1 1 calc R . .
H12E H 0.7111 0.5874 0.3082 0.044 Uiso 1 1 calc R . .
H12D H 0.5277 0.6840 0.3056 0.044 Uiso 1 1 calc R . .
C013 C 0.5002(3) 0.38408(18) 0.28464(6) 0.0267(4) Uani 1 1 d . . .
H13F H 0.5205 0.3975 0.2561 0.040 Uiso 1 1 calc R . .
H13E H 0.3972 0.3201 0.2884 0.040 Uiso 1 1 calc R . .
H13D H 0.6289 0.3582 0.2971 0.040 Uiso 1 1 calc R . .
C010 C -0.0751(3) 0.51117(18) 0.42264(6) 0.0263(4) Uani 1 1 d . . .
H10F H -0.1068 0.5364 0.3952 0.039 Uiso 1 1 calc R . .
H10E H -0.1083 0.5782 0.4409 0.039 Uiso 1 1 calc R . .
H10D H -0.1555 0.4384 0.4294 0.039 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
Cl1 0.0215(2) 0.0299(3) 0.0274(3) 0.0029(2) -0.00596(18) -0.00517(19)
C6 0.0174(9) 0.0159(9) 0.0234(10) 0.0016(8) -0.0023(7) 0.0010(7)
C5 0.0170(9) 0.0176(9) 0.0217(10) -0.0012(8) -0.0044(7) 0.0016(7)
C4 0.0155(9) 0.0198(9) 0.0187(10) 0.0004(8) -0.0013(7) 0.0003(7)
C3 0.0256(10) 0.0163(9) 0.0241(10) 0.0006(8) 0.0056(8) -0.0027(8)
C2 0.0286(10) 0.0174(10) 0.0234(10) -0.0028(8) 0.0026(8) -0.0008(8)
C1 0.0208(9) 0.0182(9) 0.0202(10) 0.0023(8) 0.0024(7) 0.0019(7)
C9 0.0254(10) 0.0219(10) 0.0219(10) 0.0002(8) 0.0022(8) 0.0013(8)
C8 0.0282(10) 0.0189(10) 0.0236(11) 0.0020(8) -0.0019(8) -0.0022(8)
O8 0.0332(8) 0.0286(8) 0.0300(8) 0.0022(6) -0.0099(6) 0.0064(6)
O7 0.0254(7) 0.0190(7) 0.0225(7) 0.0003(5) -0.0026(5) 0.0081(5)
C11 0.0195(9) 0.0227(10) 0.0207(10) 0.0002(8) 0.0000(7) 0.0020(8)
C12 0.0288(11) 0.0278(11) 0.0248(11) 0.0028(9) 0.0046(8) -0.0004(9)
C13 0.0251(10) 0.0283(11) 0.0209(10) -0.0026(8) 0.0009(8) 0.0011(8)
C10 0.0257(10) 0.0287(11) 0.0284(11) 0.0063(9) 0.0071(8) 0.0072(8)
cl2 0.0228(2) 0.0311(3) 0.0250(3) 0.0013(2) -0.00538(18) -0.0089(2)
C06 0.0163(9) 0.0170(9) 0.0208(10) 0.0003(7) -0.0030(7) -0.0004(7)
C05 0.0171(9) 0.0177(9) 0.0222(10) -0.0014(8) -0.0030(7) 0.0002(7)
C04 0.0163(9) 0.0198(9) 0.0192(10) -0.0010(8) -0.0019(7) -0.0012(7)
C03 0.0246(10) 0.0152(9) 0.0267(10) 0.0001(8) 0.0041(8) -0.0028(8)
C02 0.0269(10) 0.0172(9) 0.0246(10) -0.0029(8) 0.0032(8) -0.0016(8)
C01 0.0223(10) 0.0165(9) 0.0194(10) -0.0006(8) 0.0028(7) 0.0003(7)
C09 0.0256(10) 0.0189(10) 0.0204(10) -0.0008(8) 0.0008(8) -0.0009(8)
C08 0.0293(11) 0.0200(10) 0.0218(10) 0.0015(8) -0.0041(8) -0.0038(8)
O08 0.0364(8) 0.0317(8) 0.0311(8) 0.0013(6) -0.0121(7) 0.0037(7)
O07 0.0242(7) 0.0202(7) 0.0234(7) -0.0001(6) -0.0032(5) 0.0065(5)
C011 0.0202(9) 0.0265(10) 0.0198(10) 0.0009(8) -0.0006(7) -0.0004(8)
C012 0.0312(11) 0.0326(12) 0.0251(11) 0.0021(9) 0.0059(8) -0.0061(9)
C013 0.0272(10) 0.0321(11) 0.0207(10) -0.0045(9) 0.0014(8) -0.0009(9)
C010 0.0230(10) 0.0286(11) 0.0273(11) 0.0042(9) 0.0058(8) 0.0045(8)
_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
Cl1 C5 1.8163(18) . ?
C6 O7 1.461(2) . ?
C6 C5 1.520(2) . ?
C6 C1 1.539(3) . ?
C6 H6E 1.0000 . ?
C5 C4 1.526(2) . ?
C5 H5E 1.0000 . ?
C4 C3 1.533(2) . ?
C4 C11 1.542(2) . ?
C4 H4A 1.0000 . ?
C3 C2 1.528(2) . ?
C3 H3A 0.9900 . ?
C3 H3E 0.9900 . ?
C2 C1 1.538(2) . ?
C2 H2A 0.9900 . ?
C2 H2E 0.9900 . ?
C1 C10 1.527(2) . ?
C1 C9 1.532(2) . ?
C9 C8 1.495(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C8 O8 1.205(2) . ?
C8 O7 1.364(2) . ?
C11 C13 1.527(3) . ?
C11 C12 1.531(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
cl2 C05 1.8217(18) . ?
C06 O07 1.465(2) . ?
C06 C05 1.522(2) . ?
C06 C01 1.536(2) . ?
C06 H06E 1.0000 . ?
C05 C04 1.525(2) . ?
C05 H05E 1.0000 . ?
C04 C03 1.530(2) . ?
C04 C011 1.540(2) . ?
C04 H04A 1.0000 . ?
C03 C02 1.527(2) . ?
C03 H03E 0.9900 . ?
C03 H03A 0.9900 . ?
C02 C01 1.534(2) . ?
C02 H02E 0.9900 . ?
C02 H02A 0.9900 . ?
C01 C010 1.529(2) . ?
C01 C09 1.540(2) . ?
C09 C08 1.497(3) . ?
C09 H09A 0.9900 . ?
C09 H09B 0.9900 . ?
C08 O08 1.203(2) . ?
C08 O07 1.364(2) . ?
C011 C013 1.528(3) . ?
C011 C012 1.530(3) . ?
C011 H011 1.0000 . ?
C012 H12F 0.9800 . ?
C012 H12E 0.9800 . ?
C012 H12D 0.9800 . ?
C013 H13F 0.9800 . ?
C013 H13E 0.9800 . ?
C013 H13D 0.9800 . ?
C010 H10F 0.9800 . ?
C010 H10E 0.9800 . ?
C010 H10D 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
O7 C6 C5 106.16(14) . . ?
O7 C6 C1 104.10(13) . . ?
C5 C6 C1 118.94(15) . . ?
O7 C6 H6E 109.1 . . ?
C5 C6 H6E 109.1 . . ?
C1 C6 H6E 109.1 . . ?
C6 C5 C4 114.75(15) . . ?
C6 C5 Cl1 106.55(12) . . ?
C4 C5 Cl1 111.02(12) . . ?
C6 C5 H5E 108.1 . . ?
C4 C5 H5E 108.1 . . ?
Cl1 C5 H5E 108.1 . . ?
C5 C4 C3 109.68(14) . . ?
C5 C4 C11 112.98(14) . . ?
C3 C4 C11 114.25(15) . . ?
C5 C4 H4A 106.5 . . ?
C3 C4 H4A 106.5 . . ?
C11 C4 H4A 106.5 . . ?
C2 C3 C4 111.64(15) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3E 109.3 . . ?
C4 C3 H3E 109.3 . . ?
H3A C3 H3E 108.0 . . ?
C3 C2 C1 113.63(15) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2E 108.8 . . ?
C1 C2 H2E 108.8 . . ?
H2A C2 H2E 107.7 . . ?
C10 C1 C9 112.25(15) . . ?
C10 C1 C2 111.53(15) . . ?
C9 C1 C2 110.01(15) . . ?
C10 C1 C6 113.15(15) . . ?
C9 C1 C6 99.30(14) . . ?
C2 C1 C6 109.99(15) . . ?
C8 C9 C1 103.81(15) . . ?
C8 C9 H9A 111.0 . . ?
C1 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C1 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
O8 C8 O7 120.39(17) . . ?
O8 C8 C9 130.42(18) . . ?
O7 C8 C9 109.18(15) . . ?
C8 O7 C6 109.28(13) . . ?
C13 C11 C12 109.72(15) . . ?
C13 C11 C4 111.77(15) . . ?
C12 C11 C4 112.12(15) . . ?
C13 C11 H11 107.7 . . ?
C12 C11 H11 107.7 . . ?
C4 C11 H11 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O07 C06 C05 106.38(14) . . ?
O07 C06 C01 104.21(13) . . ?
C05 C06 C01 118.70(15) . . ?
O07 C06 H06E 109.0 . . ?
C05 C06 H06E 109.0 . . ?
C01 C06 H06E 109.0 . . ?
C06 C05 C04 115.03(14) . . ?
C06 C05 cl2 106.41(12) . . ?
C04 C05 cl2 110.49(12) . . ?
C06 C05 H05E 108.2 . . ?
C04 C05 H05E 108.2 . . ?
cl2 C05 H05E 108.2 . . ?
C05 C04 C03 109.56(14) . . ?
C05 C04 C011 113.49(14) . . ?
C03 C04 C011 113.81(15) . . ?
C05 C04 H04A 106.5 . . ?
C03 C04 H04A 106.5 . . ?
C011 C04 H04A 106.5 . . ?
C02 C03 C04 111.83(15) . . ?
C02 C03 H03E 109.2 . . ?
C04 C03 H03E 109.2 . . ?
C02 C03 H03A 109.2 . . ?
C04 C03 H03A 109.2 . . ?
H03E C03 H03A 107.9 . . ?
C03 C02 C01 113.30(15) . . ?
C03 C02 H02E 108.9 . . ?
C01 C02 H02E 108.9 . . ?
C03 C02 H02A 108.9 . . ?
C01 C02 H02A 108.9 . . ?
H02E C02 H02A 107.7 . . ?
C010 C01 C02 111.63(15) . . ?
C010 C01 C06 112.92(15) . . ?
C02 C01 C06 110.13(15) . . ?
C010 C01 C09 112.31(15) . . ?
C02 C01 C09 109.78(15) . . ?
C06 C01 C09 99.46(14) . . ?
C08 C09 C01 103.86(15) . . ?
C08 C09 H09A 111.0 . . ?
C01 C09 H09A 111.0 . . ?
C08 C09 H09B 111.0 . . ?
C01 C09 H09B 111.0 . . ?
H09A C09 H09B 109.0 . . ?
O08 C08 O07 120.72(18) . . ?
O08 C08 C09 129.85(18) . . ?
O07 C08 C09 109.43(15) . . ?
C08 O07 C06 109.13(13) . . ?
C013 C011 C012 109.71(15) . . ?
C013 C011 C04 112.46(15) . . ?
C012 C011 C04 111.69(15) . . ?
C013 C011 H011 107.6 . . ?
C012 C011 H011 107.6 . . ?
C04 C011 H011 107.6 . . ?
C011 C012 H12F 109.5 . . ?
C011 C012 H12E 109.5 . . ?
H12F C012 H12E 109.5 . . ?
C011 C012 H12D 109.5 . . ?
H12F C012 H12D 109.5 . . ?
H12E C012 H12D 109.5 . . ?
C011 C013 H13F 109.5 . . ?
C011 C013 H13E 109.5 . . ?
H13F C013 H13E 109.5 . . ?
C011 C013 H13D 109.5 . . ?
H13F C013 H13D 109.5 . . ?
H13E C013 H13D 109.5 . . ?
C01 C010 H10F 109.5 . . ?
C01 C010 H10E 109.5 . . ?
H10F C010 H10E 109.5 . . ?
C01 C010 H10D 109.5 . . ?
H10F C010 H10D 109.5 . . ?
H10E C010 H10D 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
O7 C6 C5 C4 76.02(17) . . . . ?
C1 C6 C5 C4 -40.7(2) . . . . ?
O7 C6 C5 Cl1 -160.69(11) . . . . ?
C1 C6 C5 Cl1 82.56(16) . . . . ?
C6 C5 C4 C3 47.74(19) . . . . ?
Cl1 C5 C4 C3 -73.13(16) . . . . ?
C6 C5 C4 C11 176.46(14) . . . . ?
Cl1 C5 C4 C11 55.60(17) . . . . ?
C5 C4 C3 C2 -57.47(19) . . . . ?
C11 C4 C3 C2 174.51(14) . . . . ?
C4 C3 C2 C1 59.7(2) . . . . ?
C3 C2 C1 C10 78.7(2) . . . . ?
C3 C2 C1 C9 -156.03(15) . . . . ?
C3 C2 C1 C6 -47.6(2) . . . . ?
O7 C6 C1 C10 155.59(14) . . . . ?
C5 C6 C1 C10 -86.58(19) . . . . ?
O7 C6 C1 C9 36.42(16) . . . . ?
C5 C6 C1 C9 154.25(15) . . . . ?
O7 C6 C1 C2 -78.94(17) . . . . ?
C5 C6 C1 C2 38.9(2) . . . . ?
C10 C1 C9 C8 -153.51(16) . . . . ?
C2 C1 C9 C8 81.67(18) . . . . ?
C6 C1 C9 C8 -33.68(17) . . . . ?
C1 C9 C8 O8 -159.4(2) . . . . ?
C1 C9 C8 O7 19.90(19) . . . . ?
O8 C8 O7 C6 -176.43(17) . . . . ?
C9 C8 O7 C6 4.17(19) . . . . ?
C5 C6 O7 C8 -152.84(14) . . . . ?
C1 C6 O7 C8 -26.52(18) . . . . ?
C5 C4 C11 C13 50.6(2) . . . . ?
C3 C4 C11 C13 176.89(15) . . . . ?
C5 C4 C11 C12 174.25(14) . . . . ?
C3 C4 C11 C12 -59.4(2) . . . . ?
O07 C06 C05 C04 -76.65(17) . . . . ?
C01 C06 C05 C04 40.3(2) . . . . ?
O07 C06 C05 cl2 160.66(11) . . . . ?
C01 C06 C05 cl2 -82.44(16) . . . . ?
C06 C05 C04 C03 -47.13(19) . . . . ?
cl2 C05 C04 C03 73.35(16) . . . . ?
C06 C05 C04 C011 -175.55(14) . . . . ?
cl2 C05 C04 C011 -55.07(17) . . . . ?
C05 C04 C03 C02 57.34(19) . . . . ?
C011 C04 C03 C02 -174.41(14) . . . . ?
C04 C03 C02 C01 -60.2(2) . . . . ?
C03 C02 C01 C010 -78.0(2) . . . . ?
C03 C02 C01 C06 48.2(2) . . . . ?
C03 C02 C01 C09 156.76(15) . . . . ?
O07 C06 C01 C010 -155.46(14) . . . . ?
C05 C06 C01 C010 86.50(19) . . . . ?
O07 C06 C01 C02 79.01(17) . . . . ?
C05 C06 C01 C02 -39.0(2) . . . . ?
O07 C06 C01 C09 -36.23(16) . . . . ?
C05 C06 C01 C09 -154.28(15) . . . . ?
C010 C01 C09 C08 152.09(15) . . . . ?
C02 C01 C09 C08 -83.10(17) . . . . ?
C06 C01 C09 C08 32.41(17) . . . . ?
C01 C09 C08 O08 162.0(2) . . . . ?
C01 C09 C08 O07 -17.86(19) . . . . ?
O08 C08 O07 C06 174.10(17) . . . . ?
C09 C08 O07 C06 -6.03(19) . . . . ?
C05 C06 O07 C08 153.84(14) . . . . ?
C01 C06 O07 C08 27.63(18) . . . . ?
C05 C04 C011 C013 -48.1(2) . . . . ?
C03 C04 C011 C013 -174.28(15) . . . . ?
C05 C04 C011 C012 -171.94(15) . . . . ?
C03 C04 C011 C012 61.9(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max 0.263
_refine_diff_density_min -0.258
_refine_diff_density_rms 0.046
#==== end of cif