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# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
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data_cpd1
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C17 H18 O6'
_chemical_formula_weight 318.31
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.2815(2)
_cell_length_b 8.4808(2)
_cell_length_c 13.3432(3)
_cell_angle_alpha 104.8350(10)
_cell_angle_beta 95.4060(10)
_cell_angle_gamma 114.0380(10)
_cell_volume 806.15(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description ?
_exptl_crystal_colour ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.311
_exptl_crystal_F_000 336
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.450
_exptl_crystal_size_mid 0.400
_exptl_crystal_size_min 0.200
_exptl_absorpt_coefficient_mu 0.100
_shelx_estimated_absorpt_T_min 0.957
_shelx_estimated_absorpt_T_max 0.980
_exptl_absorpt_correction_type ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source ?
_diffrn_measurement_device_type ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 18026
_diffrn_reflns_av_unetI/netI 0.0218
_diffrn_reflns_av_R_equivalents 0.0205
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_theta_min 2.764
_diffrn_reflns_theta_max 30.553
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total 4878
_reflns_number_gt 3744
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0984P)^2^+0.1276P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 4878
_refine_ls_number_parameters 212
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0698
_refine_ls_R_factor_gt 0.0536
_refine_ls_wR_factor_ref 0.1709
_refine_ls_wR_factor_gt 0.1568
_refine_ls_goodness_of_fit_ref 1.036
_refine_ls_restrained_S_all 1.036
_refine_ls_shift/su_max 0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.4797(2) 0.70152(19) 0.60215(11) 0.0418(3) Uani 1 1 d . . . . .
C3 C 0.33984(18) 0.54597(16) 0.59878(9) 0.0352(3) Uani 1 1 d . . . . .
C4 C 0.32304(16) 0.47712(15) 0.69302(9) 0.0308(2) Uani 1 1 d . . . . .
H4 H 0.2926 0.3472 0.6667 0.037 Uiso 1 1 calc R U . . .
C4A C 0.50279(16) 0.57275(15) 0.77304(9) 0.0322(2) Uani 1 1 d . . . . .
C5 C 0.53684(18) 0.50874(18) 0.85503(10) 0.0380(3) Uani 1 1 d . . . . .
H5 H 0.4477 0.4021 0.8601 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7006(2) 0.6006(2) 0.92899(11) 0.0454(3) Uani 1 1 d . . . . .
H6 H 0.7200 0.5565 0.9836 0.055 Uiso 1 1 calc R U . . .
C7 C 0.8354(2) 0.7580(2) 0.92176(12) 0.0504(4) Uani 1 1 d . . . . .
H7 H 0.9456 0.8195 0.9715 0.060 Uiso 1 1 calc R U . . .
C8 C 0.8067(2) 0.8241(2) 0.84079(13) 0.0497(3) Uani 1 1 d . . . . .
H8 H 0.8969 0.9297 0.8353 0.060 Uiso 1 1 calc R U . . .
C8A C 0.64130(18) 0.73028(17) 0.76785(11) 0.0394(3) Uani 1 1 d . . . . .
C9 C 0.1933(2) 0.43683(19) 0.50140(10) 0.0415(3) Uani 1 1 d . . . . .
C10 C -0.0566(3) 0.1484(3) 0.41434(14) 0.0666(5) Uani 1 1 d . . . . .
H103 H -0.0088 0.1392 0.3514 0.100 Uiso 1 1 calc R U . . .
H102 H -0.1440 0.1947 0.4083 0.100 Uiso 1 1 calc R U . . .
H101 H -0.1139 0.0299 0.4223 0.100 Uiso 1 1 calc R U . . .
C11 C 0.5093(3) 0.7933(3) 0.51882(15) 0.0615(5) Uani 1 1 d . . . . .
H111 H 0.4533 0.8738 0.5280 0.092 Uiso 1 1 calc R U . . .
H113 H 0.4564 0.7028 0.4496 0.092 Uiso 1 1 calc R U . . .
H112 H 0.6371 0.8622 0.5254 0.092 Uiso 1 1 calc R U . . .
C1' C 0.23004(17) 0.67134(16) 0.83216(10) 0.0358(3) Uani 1 1 d . . . . .
C2' C 0.16354(16) 0.49335(15) 0.74140(9) 0.0329(2) Uani 1 1 d . . . . .
H2' H 0.0799 0.4952 0.6852 0.040 Uiso 1 1 calc R U . . .
C3' C 0.05528(19) 0.33225(17) 0.77809(11) 0.0413(3) Uani 1 1 d . . . . .
C4' C -0.1211(3) 0.3158(3) 0.8012(2) 0.0825(7) Uani 1 1 d . . . . .
H4'1 H -0.1069 0.3650 0.8765 0.124 Uiso 1 1 calc R U . . .
H4'3 H -0.2084 0.1896 0.7764 0.124 Uiso 1 1 calc R U . . .
H4'2 H -0.1623 0.3822 0.7656 0.124 Uiso 1 1 calc R U . . .
C5' C 0.3590(3) 0.9903(2) 0.86986(17) 0.0761(6) Uani 1 1 d . . . . .
H5'1 H 0.4843 1.0282 0.8994 0.114 Uiso 1 1 calc R U . . .
H5'3 H 0.2939 0.9896 0.9257 0.114 Uiso 1 1 calc R U . . .
H5'2 H 0.3499 1.0736 0.8352 0.114 Uiso 1 1 calc R U . . .
O1 O 0.62302(15) 0.80309(13) 0.68791(9) 0.0517(3) Uani 1 1 d . . . . .
O2 O 0.16429(19) 0.48417(19) 0.42669(9) 0.0664(4) Uani 1 1 d . . . . .
O3 O 0.08910(15) 0.27062(14) 0.50593(8) 0.0500(3) Uani 1 1 d . . . . .
O4 O 0.28253(16) 0.81027(13) 0.79388(9) 0.0527(3) Uani 1 1 d . . . . .
O5 O 0.23806(18) 0.68523(15) 0.92416(8) 0.0576(3) Uani 1 1 d . . . . .
O6 O 0.10803(15) 0.22158(14) 0.78506(10) 0.0542(3) Uani 1 1 d . . . . .
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
C2 0.0518(8) 0.0426(6) 0.0426(7) 0.0242(5) 0.0156(6) 0.0251(6)
C3 0.0454(7) 0.0377(6) 0.0297(5) 0.0152(4) 0.0094(5) 0.0227(5)
C4 0.0364(6) 0.0293(5) 0.0282(5) 0.0116(4) 0.0067(4) 0.0149(4)
C4A 0.0342(6) 0.0325(5) 0.0315(5) 0.0112(4) 0.0068(4) 0.0162(5)
C5 0.0387(6) 0.0440(6) 0.0361(6) 0.0179(5) 0.0087(5) 0.0199(5)
C6 0.0473(8) 0.0584(8) 0.0359(6) 0.0164(6) 0.0057(5) 0.0288(7)
C7 0.0412(7) 0.0541(8) 0.0439(7) 0.0052(6) -0.0017(6) 0.0188(6)
C8 0.0410(7) 0.0402(7) 0.0543(8) 0.0116(6) 0.0061(6) 0.0085(6)
C8A 0.0420(7) 0.0344(6) 0.0408(6) 0.0141(5) 0.0085(5) 0.0152(5)
C9 0.0524(8) 0.0501(7) 0.0306(6) 0.0148(5) 0.0096(5) 0.0301(6)
C10 0.0654(11) 0.0609(10) 0.0479(9) 0.0018(7) -0.0124(8) 0.0189(8)
C11 0.0731(11) 0.0660(10) 0.0682(11) 0.0491(9) 0.0267(9) 0.0340(9)
C1' 0.0380(6) 0.0343(5) 0.0363(6) 0.0099(4) 0.0059(5) 0.0187(5)
C2' 0.0348(6) 0.0325(5) 0.0307(5) 0.0103(4) 0.0051(4) 0.0149(5)
C3' 0.0403(7) 0.0359(6) 0.0398(7) 0.0101(5) 0.0104(5) 0.0107(5)
C4' 0.0608(12) 0.0680(12) 0.1279(19) 0.0365(12) 0.0492(12) 0.0287(10)
C5' 0.0978(15) 0.0333(7) 0.0772(12) 0.0054(7) 0.0018(11) 0.0218(8)
O1 0.0521(6) 0.0397(5) 0.0575(6) 0.0275(5) 0.0060(5) 0.0097(4)
O2 0.0783(9) 0.0808(8) 0.0429(6) 0.0327(6) 0.0017(6) 0.0331(7)
O3 0.0565(6) 0.0458(5) 0.0371(5) 0.0091(4) -0.0043(4) 0.0186(5)
O4 0.0707(7) 0.0335(5) 0.0509(6) 0.0131(4) 0.0056(5) 0.0225(5)
O5 0.0814(8) 0.0501(6) 0.0354(5) 0.0081(4) 0.0126(5) 0.0274(6)
O6 0.0534(6) 0.0424(5) 0.0706(7) 0.0301(5) 0.0178(5) 0.0172(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
C2 C3 1.3415(19) . ?
C2 O1 1.3661(18) . ?
C2 C11 1.4971(18) . ?
C3 C9 1.4796(18) . ?
C3 C4 1.5113(15) . ?
C4 C4A 1.5124(16) . ?
C4 C2' 1.5633(17) . ?
C4 H4 0.9800 . ?
C4A C8A 1.3855(17) . ?
C4A C5 1.3933(16) . ?
C5 C6 1.3834(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(2) . ?
C7 H7 0.9300 . ?
C8 C8A 1.3863(19) . ?
C8 H8 0.9300 . ?
C8A O1 1.3874(16) . ?
C9 O2 1.2047(15) . ?
C9 O3 1.3409(18) . ?
C10 O3 1.4415(18) . ?
C10 H103 0.9600 . ?
C10 H102 0.9600 . ?
C10 H101 0.9600 . ?
C11 H111 0.9600 . ?
C11 H113 0.9600 . ?
C11 H112 0.9600 . ?
C1' O5 1.1956(16) . ?
C1' O4 1.3308(16) . ?
C1' C2' 1.5197(16) . ?
C2' C3' 1.5288(17) . ?
C2' H2' 0.9800 . ?
C3' O6 1.2049(17) . ?
C3' C4' 1.479(2) . ?
C4' H4'1 0.9600 . ?
C4' H4'3 0.9600 . ?
C4' H4'2 0.9600 . ?
C5' O4 1.4349(19) . ?
C5' H5'1 0.9600 . ?
C5' H5'3 0.9600 . ?
C5' H5'2 0.9600 . ?
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
C3 C2 O1 122.77(11) . . ?
C3 C2 C11 128.44(14) . . ?
O1 C2 C11 108.79(13) . . ?
C2 C3 C9 120.25(11) . . ?
C2 C3 C4 122.17(11) . . ?
C9 C3 C4 117.58(11) . . ?
C3 C4 C4A 110.44(10) . . ?
C3 C4 C2' 110.46(9) . . ?
C4A C4 C2' 113.47(9) . . ?
C3 C4 H4 107.4 . . ?
C4A C4 H4 107.4 . . ?
C2' C4 H4 107.4 . . ?
C8A C4A C5 117.04(11) . . ?
C8A C4A C4 120.75(10) . . ?
C5 C4A C4 122.21(11) . . ?
C6 C5 C4A 121.33(12) . . ?
C6 C5 H5 119.3 . . ?
C4A C5 H5 119.3 . . ?
C7 C6 C5 120.07(12) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 120.05(13) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C8A 118.91(13) . . ?
C7 C8 H8 120.5 . . ?
C8A C8 H8 120.5 . . ?
C4A C8A C8 122.59(12) . . ?
C4A C8A O1 121.67(12) . . ?
C8 C8A O1 115.74(12) . . ?
O2 C9 O3 122.21(13) . . ?
O2 C9 C3 127.18(14) . . ?
O3 C9 C3 110.60(10) . . ?
O3 C10 H103 109.5 . . ?
O3 C10 H102 109.5 . . ?
H103 C10 H102 109.5 . . ?
O3 C10 H101 109.5 . . ?
H103 C10 H101 109.5 . . ?
H102 C10 H101 109.5 . . ?
C2 C11 H111 109.5 . . ?
C2 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
C2 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
H113 C11 H112 109.5 . . ?
O5 C1' O4 125.07(12) . . ?
O5 C1' C2' 125.36(12) . . ?
O4 C1' C2' 109.55(10) . . ?
C1' C2' C3' 109.99(10) . . ?
C1' C2' C4 111.44(10) . . ?
C3' C2' C4 113.46(10) . . ?
C1' C2' H2' 107.2 . . ?
C3' C2' H2' 107.2 . . ?
C4 C2' H2' 107.2 . . ?
O6 C3' C4' 121.63(14) . . ?
O6 C3' C2' 121.94(12) . . ?
C4' C3' C2' 116.39(14) . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
H4'3 C4' H4'2 109.5 . . ?
O4 C5' H5'1 109.5 . . ?
O4 C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
O4 C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
H5'3 C5' H5'2 109.5 . . ?
C2 O1 C8A 119.18(10) . . ?
C9 O3 C10 116.22(12) . . ?
C1' O4 C5' 116.93(13) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C9 -176.74(12) . . . . ?
C11 C2 C3 C9 3.3(2) . . . . ?
O1 C2 C3 C4 4.4(2) . . . . ?
C11 C2 C3 C4 -175.62(14) . . . . ?
C2 C3 C4 C4A -16.34(16) . . . . ?
C9 C3 C4 C4A 164.75(10) . . . . ?
C2 C3 C4 C2' 110.02(13) . . . . ?
C9 C3 C4 C2' -68.90(13) . . . . ?
C3 C4 C4A C8A 14.89(15) . . . . ?
C2' C4 C4A C8A -109.76(13) . . . . ?
C3 C4 C4A C5 -165.55(11) . . . . ?
C2' C4 C4A C5 69.81(14) . . . . ?
C8A C4A C5 C6 1.18(19) . . . . ?
C4 C4A C5 C6 -178.40(12) . . . . ?
C4A C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C8A 0.2(2) . . . . ?
C5 C4A C8A C8 -0.9(2) . . . . ?
C4 C4A C8A C8 178.72(12) . . . . ?
C5 C4A C8A O1 178.45(12) . . . . ?
C4 C4A C8A O1 -1.96(19) . . . . ?
C7 C8 C8A C4A 0.2(2) . . . . ?
C7 C8 C8A O1 -179.15(13) . . . . ?
C2 C3 C9 O2 -13.9(2) . . . . ?
C4 C3 C9 O2 165.08(14) . . . . ?
C2 C3 C9 O3 166.84(12) . . . . ?
C4 C3 C9 O3 -14.22(16) . . . . ?
O5 C1' C2' C3' 17.33(18) . . . . ?
O4 C1' C2' C3' -164.26(11) . . . . ?
O5 C1' C2' C4 -109.40(15) . . . . ?
O4 C1' C2' C4 69.02(13) . . . . ?
C3 C4 C2' C1' -93.82(11) . . . . ?
C4A C4 C2' C1' 30.82(12) . . . . ?
C3 C4 C2' C3' 141.38(10) . . . . ?
C4A C4 C2' C3' -93.99(11) . . . . ?
C1' C2' C3' O6 -113.84(14) . . . . ?
C4 C2' C3' O6 11.75(17) . . . . ?
C1' C2' C3' C4' 68.15(18) . . . . ?
C4 C2' C3' C4' -166.26(15) . . . . ?
C3 C2 O1 C8A 10.7(2) . . . . ?
C11 C2 O1 C8A -169.29(13) . . . . ?
C4A C8A O1 C2 -11.8(2) . . . . ?
C8 C8A O1 C2 167.54(13) . . . . ?
O2 C9 O3 C10 2.2(2) . . . . ?
C3 C9 O3 C10 -178.46(13) . . . . ?
O5 C1' O4 C5' 1.8(2) . . . . ?
C2' C1' O4 C5' -176.65(15) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
C11 H113 O2 0.96 2.30 2.852(2) 115.6 .
C2' H2' O2 0.98 2.49 3.4542(16) 167.9 2_566
_refine_diff_density_max 0.304
_refine_diff_density_min -0.260
_refine_diff_density_rms 0.064
_shelxl_version_number 2013-3
_shelx_res_file
;
TITL AP12002TA_0m in P-1
CELL 0.71073 8.2815 8.4808 13.3432 104.835 95.406 114.038
ZERR 2.00 0.0002 0.0002 0.0003 0.001 0.001 0.001
LATT 1
SFAC C H O
UNIT 34 36 12
OMIT 0 -1 1
OMIT 0 0 1
OMIT -3 1 5
OMIT -2 1 0
L.S. 5
ACTA
BOND $H
FMAP 2
PLAN 5
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
EQIV $1 -x, -y+1, -z+1
CONF
HTAB
SIZE 0.200 0.400 0.450
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
HTAB C11 O2
HTAB C2' O2_$1
TEMP 23.000
WGHT 0.098400 0.127600
FVAR 0.46964
C2 1 0.479746 0.701524 0.602146 11.00000 0.05181 0.04262 =
0.04259 0.02415 0.01556 0.02506
C3 1 0.339836 0.545966 0.598780 11.00000 0.04542 0.03771 =
0.02967 0.01522 0.00942 0.02275
C4 1 0.323042 0.477118 0.693018 11.00000 0.03638 0.02925 =
0.02825 0.01161 0.00673 0.01491
AFIX 13
H4 2 0.292622 0.347161 0.666734 11.00000 -1.20000
AFIX 0
C4A 1 0.502785 0.572747 0.773045 11.00000 0.03425 0.03252 =
0.03148 0.01124 0.00678 0.01622
C5 1 0.536840 0.508743 0.855026 11.00000 0.03867 0.04397 =
0.03606 0.01788 0.00873 0.01987
AFIX 43
H5 2 0.447672 0.402086 0.860122 11.00000 -1.20000
AFIX 0
C6 1 0.700615 0.600649 0.928993 11.00000 0.04735 0.05842 =
0.03586 0.01639 0.00574 0.02885
AFIX 43
H6 2 0.720007 0.556466 0.983647 11.00000 -1.20000
AFIX 0
C7 1 0.835436 0.758043 0.921759 11.00000 0.04118 0.05412 =
0.04389 0.00521 -0.00173 0.01877
AFIX 43
H7 2 0.945562 0.819540 0.971454 11.00000 -1.20000
AFIX 0
C8 1 0.806748 0.824066 0.840795 11.00000 0.04102 0.04021 =
0.05434 0.01156 0.00610 0.00852
AFIX 43
H8 2 0.896942 0.929714 0.835292 11.00000 -1.20000
AFIX 0
C8A 1 0.641301 0.730285 0.767851 11.00000 0.04203 0.03436 =
0.04079 0.01410 0.00854 0.01523
C9 1 0.193340 0.436831 0.501404 11.00000 0.05242 0.05011 =
0.03061 0.01482 0.00958 0.03005
C10 1 -0.056569 0.148391 0.414345 11.00000 0.06540 0.06095 =
0.04789 0.00175 -0.01243 0.01889
AFIX 137
H103 2 -0.008805 0.139168 0.351424 11.00000 -1.50000
H102 2 -0.144005 0.194669 0.408297 11.00000 -1.50000
H101 2 -0.113907 0.029940 0.422321 11.00000 -1.50000
AFIX 0
C11 1 0.509275 0.793317 0.518821 11.00000 0.07307 0.06597 =
0.06819 0.04910 0.02666 0.03398
AFIX 137
H111 2 0.453303 0.873815 0.528022 11.00000 -1.50000
H113 2 0.456371 0.702798 0.449568 11.00000 -1.50000
H112 2 0.637084 0.862198 0.525441 11.00000 -1.50000
AFIX 0
C1' 1 0.230040 0.671344 0.832162 11.00000 0.03795 0.03428 =
0.03631 0.00993 0.00591 0.01874
C2' 1 0.163543 0.493353 0.741401 11.00000 0.03477 0.03254 =
0.03074 0.01030 0.00506 0.01488
AFIX 13
H2' 2 0.079860 0.495222 0.685178 11.00000 -1.20000
AFIX 0
C3' 1 0.055282 0.332255 0.778090 11.00000 0.04035 0.03587 =
0.03981 0.01008 0.01044 0.01068
C4' 1 -0.121071 0.315833 0.801176 11.00000 0.06076 0.06795 =
0.12790 0.03652 0.04922 0.02868
AFIX 137
H4'1 2 -0.106944 0.365019 0.876515 11.00000 -1.50000
H4'3 2 -0.208401 0.189580 0.776351 11.00000 -1.50000
H4'2 2 -0.162313 0.382243 0.765643 11.00000 -1.50000
AFIX 0
C5' 1 0.358986 0.990316 0.869858 11.00000 0.09785 0.03332 =
0.07724 0.00539 0.00180 0.02177
AFIX 137
H5'1 2 0.484266 1.028221 0.899423 11.00000 -1.50000
H5'3 2 0.293936 0.989583 0.925742 11.00000 -1.50000
H5'2 2 0.349905 1.073599 0.835245 11.00000 -1.50000
AFIX 0
O1 3 0.623018 0.803086 0.687911 11.00000 0.05206 0.03975 =
0.05752 0.02748 0.00597 0.00965
O2 3 0.164293 0.484167 0.426691 11.00000 0.07826 0.08080 =
0.04289 0.03273 0.00172 0.03313
O3 3 0.089099 0.270615 0.505929 11.00000 0.05652 0.04579 =
0.03712 0.00905 -0.00433 0.01864
O4 3 0.282533 0.810272 0.793876 11.00000 0.07067 0.03349 =
0.05092 0.01308 0.00562 0.02251
O5 3 0.238062 0.685230 0.924160 11.00000 0.08141 0.05013 =
0.03537 0.00810 0.01259 0.02739
O6 3 0.108035 0.221576 0.785063 11.00000 0.05340 0.04245 =
0.07061 0.03014 0.01780 0.01718
HKLF 4 1 1 0 0 0 1 0 0 0 1
REM AP12002TA_0m in P-1
REM R1 = 0.0536 for 3744 Fo > 4sig(Fo) and 0.0698 for all 4878 data
REM 212 parameters refined using 0 restraints
END
WGHT 0.0984 0.1276
REM Instructions for potential hydrogen bonds
HTAB C11 O2
HTAB C2' O2_$1
REM Highest difference peak 0.304, deepest hole -0.260, 1-sigma level 0.064
Q1 1 -0.2236 0.2267 0.8230 11.00000 0.05 0.30
Q2 1 0.3425 0.5148 0.6472 11.00000 0.05 0.30
Q3 1 0.4162 0.5236 0.7340 11.00000 0.05 0.29
Q4 1 0.1993 0.5776 0.7823 11.00000 0.05 0.28
Q5 1 0.5601 0.6653 0.7796 11.00000 0.05 0.28
;
_shelx_res_checksum 78636
_database_code_depnum_ccdc_archive 'CCDC 952576'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_cpd2
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C18 H20 O7'
_chemical_formula_sum 'C18 H20 O7'
_chemical_formula_weight 348.34
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'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.0528(4)
_cell_length_b 9.1110(4)
_cell_length_c 11.9970(5)
_cell_angle_alpha 80.134(2)
_cell_angle_beta 68.141(2)
_cell_angle_gamma 72.313(2)
_cell_volume 873.06(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description ?
_exptl_crystal_colour ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.325
_exptl_crystal_F_000 368
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.600
_exptl_crystal_size_mid 0.500
_exptl_crystal_size_min 0.500
_exptl_absorpt_coefficient_mu 0.102
_shelx_estimated_absorpt_T_min 0.941
_shelx_estimated_absorpt_T_max 0.951
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.941
_exptl_absorpt_correction_T_max 0.950
_exptl_absorpt_process_details '(SADABS; Bruker, 2008)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source ?
_diffrn_measurement_device_type ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 9751
_diffrn_reflns_av_unetI/netI 0.0257
_diffrn_reflns_av_R_equivalents 0.0159
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.885
_diffrn_reflns_theta_max 30.558
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total 5278
_reflns_number_gt 3784
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0967P)^2^+0.1324P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 5278
_refine_ls_number_parameters 231
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0746
_refine_ls_R_factor_gt 0.0540
_refine_ls_wR_factor_ref 0.1770
_refine_ls_wR_factor_gt 0.1559
_refine_ls_goodness_of_fit_ref 1.048
_refine_ls_restrained_S_all 1.048
_refine_ls_shift/su_max 0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.28456(16) 0.40001(15) 0.51476(11) 0.0374(3) Uani 1 1 d . . . . .
C3 C 0.26381(15) 0.27541(14) 0.48259(10) 0.0331(3) Uani 1 1 d . . . . .
C4 C 0.21945(16) 0.27832(13) 0.37226(11) 0.0334(3) Uani 1 1 d . . . . .
H4 H 0.1256 0.2332 0.3971 0.040 Uiso 1 1 calc R U . . .
C4A C 0.16509(16) 0.44237(14) 0.32399(11) 0.0356(3) Uani 1 1 d . . . . .
C5 C 0.09418(18) 0.47605(17) 0.23515(13) 0.0444(3) Uani 1 1 d . . . . .
H5 H 0.0753 0.3970 0.2069 0.053 Uiso 1 1 calc R U . . .
C6 C 0.0508(2) 0.62734(19) 0.18753(14) 0.0515(4) Uani 1 1 d . . . . .
C7 C 0.0783(2) 0.74582(17) 0.22883(15) 0.0553(4) Uani 1 1 d . . . . .
H7 H 0.0512 0.8465 0.1964 0.066 Uiso 1 1 calc R U . . .
C8 C 0.1461(2) 0.71323(16) 0.31808(15) 0.0506(4) Uani 1 1 d . . . . .
H8 H 0.1633 0.7925 0.3474 0.061 Uiso 1 1 calc R U . . .
C8A C 0.18914(17) 0.56289(15) 0.36480(12) 0.0388(3) Uani 1 1 d . . . . .
C9 C 0.28533(17) 0.12794(15) 0.55562(11) 0.0375(3) Uani 1 1 d . . . . .
C10 C 0.2390(3) -0.12070(18) 0.59065(17) 0.0610(4) Uani 1 1 d . . . . .
H101 H 0.3527 -0.1718 0.5795 0.091 Uiso 1 1 calc R U . . .
H102 H 0.1932 -0.1824 0.5618 0.091 Uiso 1 1 calc R U . . .
H103 H 0.1789 -0.1068 0.6747 0.091 Uiso 1 1 calc R U . . .
C11 C 0.3362(2) 0.41260(19) 0.61625(14) 0.0509(4) Uani 1 1 d . . . . .
H111 H 0.4539 0.3744 0.5939 0.076 Uiso 1 1 calc R U . . .
H112 H 0.2844 0.3528 0.6858 0.076 Uiso 1 1 calc R U . . .
H113 H 0.3036 0.5188 0.6345 0.076 Uiso 1 1 calc R U . . .
C12 C -0.0629(4) 0.7957(3) 0.0474(2) 0.1051(10) Uani 1 1 d . . . . .
H121 H 0.0347 0.8307 0.0046 0.158 Uiso 1 1 calc R U . . .
H122 H -0.1363 0.8648 0.1089 0.158 Uiso 1 1 calc R U . . .
H123 H -0.1167 0.7937 -0.0075 0.158 Uiso 1 1 calc R U . . .
C1' C 0.46579(19) 0.26724(15) 0.17603(12) 0.0421(3) Uani 1 1 d . . . . .
C2' C 0.36679(17) 0.17447(14) 0.27640(11) 0.0356(3) Uani 1 1 d . . . . .
H2' H 0.4409 0.1080 0.3178 0.043 Uiso 1 1 calc R U . . .
C3' C 0.3134(2) 0.06877(15) 0.22118(13) 0.0458(3) Uani 1 1 d . . . . .
C4' C 0.4458(3) -0.06990(19) 0.16577(17) 0.0622(5) Uani 1 1 d . . . . .
H4'1 H 0.4753 -0.1406 0.2279 0.093 Uiso 1 1 calc R U . . .
H4'2 H 0.5410 -0.0381 0.1112 0.093 Uiso 1 1 calc R U . . .
H4'3 H 0.4060 -0.1197 0.1227 0.093 Uiso 1 1 calc R U . . .
C5' C 0.6192(3) 0.4517(3) 0.13036(18) 0.0753(6) Uani 1 1 d . . . . .
H5'1 H 0.6785 0.4059 0.0544 0.113 Uiso 1 1 calc R U . . .
H5'2 H 0.6950 0.4747 0.1591 0.113 Uiso 1 1 calc R U . . .
H5'3 H 0.5390 0.5453 0.1204 0.113 Uiso 1 1 calc R U . . .
O1 O 0.25784(14) 0.54135(11) 0.45426(10) 0.0457(3) Uani 1 1 d . . . . .
O2 O 0.34680(16) 0.09508(13) 0.63344(10) 0.0556(3) Uani 1 1 d . . . . .
O3 O 0.22725(14) 0.02815(11) 0.52434(9) 0.0470(3) Uani 1 1 d . . . . .
O4 O 0.53658(14) 0.34511(13) 0.21649(9) 0.0486(3) Uani 1 1 d . . . . .
O5 O 0.4763(2) 0.27370(17) 0.07276(10) 0.0765(5) Uani 1 1 d . . . . .
O6 O 0.17337(18) 0.09384(14) 0.22441(13) 0.0677(4) Uani 1 1 d . . . . .
O7 O -0.01896(19) 0.64544(17) 0.10099(12) 0.0755(4) Uani 1 1 d . . . . .
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
C2 0.0397(6) 0.0371(6) 0.0346(6) -0.0020(5) -0.0116(5) -0.0105(5)
C3 0.0359(6) 0.0323(5) 0.0292(5) -0.0005(4) -0.0117(5) -0.0060(4)
C4 0.0381(6) 0.0300(5) 0.0337(6) 0.0001(4) -0.0160(5) -0.0075(4)
C4A 0.0345(6) 0.0322(6) 0.0356(6) 0.0014(4) -0.0127(5) -0.0035(5)
C5 0.0466(8) 0.0409(7) 0.0427(7) 0.0000(5) -0.0204(6) -0.0023(6)
C6 0.0478(8) 0.0520(8) 0.0407(7) 0.0062(6) -0.0169(6) 0.0037(6)
C7 0.0550(9) 0.0382(7) 0.0539(9) 0.0111(6) -0.0138(7) 0.0001(6)
C8 0.0540(9) 0.0322(6) 0.0562(8) 0.0031(6) -0.0134(7) -0.0082(6)
C8A 0.0386(6) 0.0330(6) 0.0401(6) 0.0011(5) -0.0118(5) -0.0068(5)
C9 0.0412(6) 0.0337(6) 0.0326(6) -0.0021(4) -0.0119(5) -0.0037(5)
C10 0.0796(12) 0.0359(7) 0.0673(11) 0.0115(7) -0.0300(9) -0.0168(7)
C11 0.0640(9) 0.0540(8) 0.0455(8) -0.0049(6) -0.0253(7) -0.0214(7)
C12 0.126(2) 0.0894(17) 0.0780(15) 0.0203(13) -0.0595(16) 0.0185(15)
C1' 0.0533(8) 0.0370(6) 0.0320(6) -0.0061(5) -0.0126(6) -0.0065(6)
C2' 0.0452(7) 0.0299(5) 0.0317(5) -0.0021(4) -0.0174(5) -0.0047(5)
C3' 0.0686(10) 0.0330(6) 0.0422(7) -0.0014(5) -0.0272(7) -0.0124(6)
C4' 0.0863(13) 0.0419(8) 0.0575(9) -0.0172(7) -0.0238(9) -0.0091(8)
C5' 0.0914(15) 0.0867(14) 0.0541(10) 0.0039(9) -0.0110(10) -0.0543(12)
O1 0.0590(6) 0.0345(5) 0.0515(6) 0.0015(4) -0.0259(5) -0.0168(4)
O2 0.0778(8) 0.0446(6) 0.0515(6) 0.0035(5) -0.0399(6) -0.0072(5)
O3 0.0632(7) 0.0341(5) 0.0480(6) 0.0055(4) -0.0252(5) -0.0154(4)
O4 0.0528(6) 0.0573(6) 0.0390(5) -0.0005(4) -0.0141(4) -0.0224(5)
O5 0.1364(13) 0.0726(8) 0.0318(5) 0.0006(5) -0.0237(7) -0.0517(9)
O6 0.0778(9) 0.0552(7) 0.0904(10) -0.0144(6) -0.0482(8) -0.0162(6)
O7 0.0856(10) 0.0748(9) 0.0605(7) 0.0120(6) -0.0451(7) 0.0032(7)
_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
C2 C3 1.3441(18) . ?
C2 O1 1.3655(15) . ?
C2 C11 1.4896(19) . ?
C3 C9 1.4750(16) . ?
C3 C4 1.5136(17) . ?
C4 C4A 1.5100(16) . ?
C4 C2' 1.5687(18) . ?
C4 H4 0.9800 . ?
C4A C8A 1.3791(19) . ?
C4A C5 1.3856(18) . ?
C5 C6 1.3960(19) . ?
C5 H5 0.9300 . ?
C6 O7 1.367(2) . ?
C6 C7 1.383(3) . ?
C7 C8 1.372(2) . ?
C7 H7 0.9300 . ?
C8 C8A 1.3846(18) . ?
C8 H8 0.9300 . ?
C8A O1 1.3884(17) . ?
C9 O2 1.2086(16) . ?
C9 O3 1.3409(17) . ?
C10 O3 1.4454(16) . ?
C10 H101 0.9600 . ?
C10 H102 0.9600 . ?
C10 H103 0.9600 . ?
C11 H111 0.9600 . ?
C11 H112 0.9600 . ?
C11 H113 0.9600 . ?
C12 O7 1.416(2) . ?
C12 H121 0.9600 . ?
C12 H122 0.9600 . ?
C12 H123 0.9600 . ?
C1' O5 1.1992(17) . ?
C1' O4 1.3325(18) . ?
C1' C2' 1.5084(19) . ?
C2' C3' 1.5295(18) . ?
C2' H2' 0.9800 . ?
C3' O6 1.205(2) . ?
C3' C4' 1.500(2) . ?
C4' H4'1 0.9600 . ?
C4' H4'2 0.9600 . ?
C4' H4'3 0.9600 . ?
C5' O4 1.447(2) . ?
C5' H5'1 0.9600 . ?
C5' H5'2 0.9600 . ?
C5' H5'3 0.9600 . ?
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
C3 C2 O1 122.45(11) . . ?
C3 C2 C11 128.73(12) . . ?
O1 C2 C11 108.82(11) . . ?
C2 C3 C9 119.93(11) . . ?
C2 C3 C4 122.70(11) . . ?
C9 C3 C4 117.37(10) . . ?
C4A C4 C3 110.62(10) . . ?
C4A C4 C2' 113.25(10) . . ?
C3 C4 C2' 109.99(10) . . ?
C4A C4 H4 107.6 . . ?
C3 C4 H4 107.6 . . ?
C2' C4 H4 107.6 . . ?
C8A C4A C5 117.99(12) . . ?
C8A C4A C4 120.76(11) . . ?
C5 C4A C4 121.23(12) . . ?
C4A C5 C6 120.77(14) . . ?
C4A C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
O7 C6 C7 124.80(14) . . ?
O7 C6 C5 115.09(16) . . ?
C7 C6 C5 120.11(14) . . ?
C8 C7 C6 119.27(13) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C8A 120.32(15) . . ?
C7 C8 H8 119.8 . . ?
C8A C8 H8 119.8 . . ?
C4A C8A C8 121.53(13) . . ?
C4A C8A O1 122.39(11) . . ?
C8 C8A O1 116.08(13) . . ?
O2 C9 O3 122.19(12) . . ?
O2 C9 C3 127.01(13) . . ?
O3 C9 C3 110.80(10) . . ?
O3 C10 H101 109.5 . . ?
O3 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
O3 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
C2 C11 H111 109.5 . . ?
C2 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
C2 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
O7 C12 H121 109.5 . . ?
O7 C12 H122 109.5 . . ?
H121 C12 H122 109.5 . . ?
O7 C12 H123 109.5 . . ?
H121 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
O5 C1' O4 123.88(14) . . ?
O5 C1' C2' 124.31(14) . . ?
O4 C1' C2' 111.78(11) . . ?
C1' C2' C3' 108.63(10) . . ?
C1' C2' C4 112.68(10) . . ?
C3' C2' C4 113.39(11) . . ?
C1' C2' H2' 107.3 . . ?
C3' C2' H2' 107.3 . . ?
C4 C2' H2' 107.3 . . ?
O6 C3' C4' 122.37(14) . . ?
O6 C3' C2' 122.04(13) . . ?
C4' C3' C2' 115.57(14) . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
H4'2 C4' H4'3 109.5 . . ?
O4 C5' H5'1 109.5 . . ?
O4 C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
O4 C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
H5'2 C5' H5'3 109.5 . . ?
C2 O1 C8A 119.30(10) . . ?
C9 O3 C10 116.30(11) . . ?
C1' O4 C5' 116.54(12) . . ?
C6 O7 C12 117.84(19) . . ?
_refine_diff_density_max 0.322
_refine_diff_density_min -0.212
_refine_diff_density_rms 0.054
_shelxl_version_number 2013-3
_shelx_res_file
;
TITL AP13003TA_04_0m in P-1
CELL 0.71073 9.0528 9.1110 11.9970 80.134 68.141 72.313
ZERR 2.00 0.0004 0.0004 0.0005 0.002 0.002 0.002
LATT 1
SFAC C H O
UNIT 36 40 14
OMIT 0 0 1
L.S. 5
ACTA
BOND $H
FMAP 2
PLAN 5
TEMP 23.000
WGHT 0.096700 0.132400
FVAR 0.42019
C2 1 0.284561 0.400010 0.514755 11.00000 0.03969 0.03714 =
0.03461 -0.00202 -0.01156 -0.01051
C3 1 0.263806 0.275413 0.482589 11.00000 0.03587 0.03226 =
0.02919 -0.00051 -0.01173 -0.00599
C4 1 0.219447 0.278318 0.372264 11.00000 0.03814 0.02997 =
0.03369 0.00008 -0.01603 -0.00746
AFIX 13
H4 2 0.125642 0.233226 0.397063 11.00000 -1.20000
AFIX 0
C4A 1 0.165087 0.442366 0.323991 11.00000 0.03448 0.03219 =
0.03556 0.00140 -0.01269 -0.00351
C5 1 0.094184 0.476053 0.235146 11.00000 0.04661 0.04093 =
0.04269 0.00005 -0.02041 -0.00234
AFIX 43
H5 2 0.075307 0.396959 0.206904 11.00000 -1.20000
AFIX 0
C6 1 0.050753 0.627338 0.187535 11.00000 0.04781 0.05204 =
0.04067 0.00618 -0.01695 0.00366
C7 1 0.078310 0.745823 0.228826 11.00000 0.05502 0.03825 =
0.05393 0.01110 -0.01381 0.00015
AFIX 43
H7 2 0.051156 0.846511 0.196440 11.00000 -1.20000
AFIX 0
C8 1 0.146138 0.713226 0.318081 11.00000 0.05404 0.03215 =
0.05618 0.00312 -0.01342 -0.00817
AFIX 43
H8 2 0.163323 0.792486 0.347356 11.00000 -1.20000
AFIX 0
C8A 1 0.189143 0.562890 0.364802 11.00000 0.03864 0.03295 =
0.04013 0.00113 -0.01179 -0.00681
C9 1 0.285325 0.127937 0.555622 11.00000 0.04117 0.03371 =
0.03264 -0.00205 -0.01189 -0.00369
C10 1 0.238996 -0.120704 0.590646 11.00000 0.07962 0.03587 =
0.06734 0.01151 -0.03003 -0.01684
AFIX 137
H101 2 0.352685 -0.171801 0.579503 11.00000 -1.50000
H102 2 0.193229 -0.182352 0.561806 11.00000 -1.50000
H103 2 0.178876 -0.106828 0.674667 11.00000 -1.50000
AFIX 0
C11 1 0.336209 0.412598 0.616255 11.00000 0.06404 0.05401 =
0.04554 -0.00491 -0.02533 -0.02144
AFIX 137
H111 2 0.453869 0.374359 0.593858 11.00000 -1.50000
H112 2 0.284436 0.352776 0.685841 11.00000 -1.50000
H113 2 0.303607 0.518771 0.634478 11.00000 -1.50000
AFIX 0
C12 1 -0.062861 0.795749 0.047443 11.00000 0.12645 0.08942 =
0.07799 0.02025 -0.05949 0.01854
AFIX 137
H121 2 0.034674 0.830656 0.004606 11.00000 -1.50000
H122 2 -0.136324 0.864791 0.108928 11.00000 -1.50000
H123 2 -0.116703 0.793732 -0.007518 11.00000 -1.50000
AFIX 0
C1' 1 0.465789 0.267237 0.176032 11.00000 0.05328 0.03700 =
0.03204 -0.00611 -0.01264 -0.00646
C2' 1 0.366794 0.174469 0.276403 11.00000 0.04521 0.02991 =
0.03172 -0.00210 -0.01737 -0.00470
AFIX 13
H2' 2 0.440867 0.108049 0.317764 11.00000 -1.20000
AFIX 0
C3' 1 0.313445 0.068768 0.221176 11.00000 0.06861 0.03304 =
0.04218 -0.00138 -0.02717 -0.01241
C4' 1 0.445837 -0.069899 0.165771 11.00000 0.08634 0.04193 =
0.05755 -0.01721 -0.02380 -0.00911
AFIX 137
H4'1 2 0.475275 -0.140650 0.227935 11.00000 -1.50000
H4'2 2 0.541007 -0.038094 0.111189 11.00000 -1.50000
H4'3 2 0.405981 -0.119722 0.122721 11.00000 -1.50000
AFIX 0
C5' 1 0.619232 0.451735 0.130357 11.00000 0.09145 0.08671 =
0.05413 0.00392 -0.01102 -0.05430
AFIX 137
H5'1 2 0.678518 0.405948 0.054448 11.00000 -1.50000
H5'2 2 0.694993 0.474741 0.159109 11.00000 -1.50000
H5'3 2 0.539026 0.545266 0.120364 11.00000 -1.50000
AFIX 0
O1 3 0.257840 0.541349 0.454258 11.00000 0.05902 0.03454 =
0.05154 0.00145 -0.02585 -0.01684
O2 3 0.346803 0.095076 0.633440 11.00000 0.07782 0.04464 =
0.05152 0.00349 -0.03993 -0.00716
O3 3 0.227249 0.028153 0.524343 11.00000 0.06320 0.03409 =
0.04797 0.00552 -0.02523 -0.01538
O4 3 0.536581 0.345107 0.216488 11.00000 0.05283 0.05726 =
0.03900 -0.00055 -0.01407 -0.02242
O5 3 0.476299 0.273700 0.072761 11.00000 0.13639 0.07261 =
0.03184 0.00058 -0.02372 -0.05171
O6 3 0.173368 0.093843 0.224407 11.00000 0.07780 0.05522 =
0.09037 -0.01443 -0.04820 -0.01624
O7 3 -0.018961 0.645442 0.100990 11.00000 0.08559 0.07478 =
0.06053 0.01201 -0.04509 0.00325
HKLF 4
REM AP13003TA_04_0m in P-1
REM R1 = 0.0540 for 3784 Fo > 4sig(Fo) and 0.0746 for all 5278 data
REM 231 parameters refined using 0 restraints
END
WGHT 0.0967 0.1324
REM Highest difference peak 0.322, deepest hole -0.212, 1-sigma level 0.054
Q1 1 0.5765 0.2043 0.0797 11.00000 0.05 0.32
Q2 1 0.2400 0.2794 0.4308 11.00000 0.05 0.29
Q3 1 0.0962 0.5436 0.1998 11.00000 0.05 0.29
Q4 1 0.2717 0.2073 0.5149 11.00000 0.05 0.27
Q5 1 0.3106 0.3205 0.4812 11.00000 0.05 0.26
;
_shelx_res_checksum 70361
_database_code_depnum_ccdc_archive 'CCDC 952577'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_cpd3
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H17 Br O6'
_chemical_formula_sum 'C17 H17 Br O6'
_chemical_formula_weight 397.21
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'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.5665(3)
_cell_length_b 9.1041(3)
_cell_length_c 12.5319(4)
_cell_angle_alpha 77.751(2)
_cell_angle_beta 74.492(2)
_cell_angle_gamma 66.840(2)
_cell_volume 859.55(5)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description ?
_exptl_crystal_colour ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.535
_exptl_crystal_F_000 404
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.350
_exptl_crystal_size_mid 0.250
_exptl_crystal_size_min 0.200
_exptl_absorpt_coefficient_mu 2.420
_shelx_estimated_absorpt_T_min 0.485
_shelx_estimated_absorpt_T_max 0.643
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.489
_exptl_absorpt_correction_T_max 0.616
_exptl_absorpt_process_details '(SADABS; Bruker, 2008)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source ?
_diffrn_measurement_device_type ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 8378
_diffrn_reflns_av_unetI/netI 0.0409
_diffrn_reflns_av_R_equivalents 0.0182
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.891
_diffrn_reflns_theta_max 30.639
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total 5224
_reflns_number_gt 2920
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.1340P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 5224
_refine_ls_number_parameters 221
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0908
_refine_ls_R_factor_gt 0.0433
_refine_ls_wR_factor_ref 0.1233
_refine_ls_wR_factor_gt 0.1059
_refine_ls_goodness_of_fit_ref 1.007
_refine_ls_restrained_S_all 1.007
_refine_ls_shift/su_max 0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.2678(3) 0.4248(3) 0.99227(18) 0.0447(5) Uani 1 1 d . . . . .
C3 C 0.2489(3) 0.3035(3) 0.95876(17) 0.0411(5) Uani 1 1 d . . . . .
C4 C 0.2034(3) 0.3154(2) 0.84868(17) 0.0401(5) Uani 1 1 d . . . . .
H4 H 0.1045 0.2801 0.8640 0.048 Uiso 1 1 calc R U . . .
C4A C 0.1451(3) 0.4887(2) 0.79504(18) 0.0423(5) Uani 1 1 d . . . . .
C5 C 0.0708(3) 0.5347(3) 0.70165(19) 0.0497(5) Uani 1 1 d . . . . .
H5 H 0.0537 0.4588 0.6713 0.060 Uiso 1 1 calc R U . . .
C6 C 0.0226(3) 0.6924(3) 0.6540(2) 0.0568(6) Uani 1 1 d . . . . .
C7 C 0.0481(4) 0.8076(3) 0.6959(2) 0.0652(7) Uani 1 1 d . . . . .
H7 H 0.0167 0.9135 0.6620 0.078 Uiso 1 1 calc R U . . .
C8 C 0.1202(4) 0.7637(3) 0.7881(2) 0.0602(6) Uani 1 1 d . . . . .
H8 H 0.1371 0.8403 0.8179 0.072 Uiso 1 1 calc R U . . .
C8A C 0.1683(3) 0.6052(3) 0.83739(19) 0.0478(5) Uani 1 1 d . . . . .
C9 C 0.2768(3) 0.1481(3) 1.03126(18) 0.0434(5) Uani 1 1 d . . . . .
C10 C 0.2280(4) -0.0976(3) 1.0633(2) 0.0632(7) Uani 1 1 d . . . . .
H101 H 0.1715 -0.1499 1.0356 0.095 Uiso 1 1 calc R U . . .
H102 H 0.1774 -0.0860 1.1407 0.095 Uiso 1 1 calc R U . . .
H103 H 0.3493 -0.1612 1.0553 0.095 Uiso 1 1 calc R U . . .
C11 C 0.3178(4) 0.4291(3) 1.0960(2) 0.0576(6) Uani 1 1 d . . . . .
H111 H 0.4411 0.4021 1.0825 0.086 Uiso 1 1 calc R U . . .
H112 H 0.2847 0.3529 1.1541 0.086 Uiso 1 1 calc R U . . .
H113 H 0.2600 0.5352 1.1185 0.086 Uiso 1 1 calc R U . . .
C1' C 0.4572(3) 0.2863(3) 0.6816(2) 0.0506(5) Uani 1 1 d . . . . .
C2' C 0.3555(3) 0.1991(2) 0.77143(17) 0.0430(5) Uani 1 1 d . . . . .
H2' H 0.4354 0.1232 0.8182 0.052 Uiso 1 1 calc R U . . .
C3' C 0.2966(4) 0.1000(3) 0.7168(2) 0.0544(6) Uani 1 1 d . . . . .
C4' C 0.4370(5) -0.0421(4) 0.6674(3) 0.0810(9) Uani 1 1 d . . . . .
H4'1 H 0.4744 -0.1260 0.7261 0.122 Uiso 1 1 calc R U . . .
H4'2 H 0.5331 -0.0116 0.6248 0.122 Uiso 1 1 calc R U . . .
H4'3 H 0.3939 -0.0801 0.6197 0.122 Uiso 1 1 calc R U . . .
C5' C 0.6183(5) 0.4566(5) 0.6487(3) 0.0957(12) Uani 1 1 d . . . . .
H5'1 H 0.7129 0.3930 0.5970 0.144 Uiso 1 1 calc R U . . .
H5'2 H 0.6616 0.5050 0.6896 0.144 Uiso 1 1 calc R U . . .
H5'3 H 0.5367 0.5393 0.6086 0.144 Uiso 1 1 calc R U . . .
O1 O 0.2380(2) 0.57312(19) 0.93043(14) 0.0543(4) Uani 1 1 d . . . . .
O2 O 0.3530(2) 0.1012(2) 1.10715(14) 0.0599(4) Uani 1 1 d . . . . .
O3 O 0.2062(2) 0.05937(18) 1.00064(13) 0.0526(4) Uani 1 1 d . . . . .
O4 O 0.5332(2) 0.3544(2) 0.72566(14) 0.0607(5) Uani 1 1 d . . . . .
O5 O 0.4658(3) 0.2955(3) 0.58379(16) 0.0815(6) Uani 1 1 d . . . . .
O6 O 0.1464(3) 0.1324(2) 0.71855(17) 0.0690(5) Uani 1 1 d . . . . .
Br1 Br -0.07911(4) 0.75336(4) 0.52692(3) 0.08619(16) Uani 1 1 d . . . . .
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
C2 0.0443(12) 0.0482(12) 0.0397(11) 0.0002(9) -0.0086(9) -0.0174(10)
C3 0.0419(11) 0.0424(11) 0.0345(10) 0.0037(8) -0.0090(8) -0.0139(9)
C4 0.0400(11) 0.0378(10) 0.0400(11) 0.0058(8) -0.0136(8) -0.0133(8)
C4A 0.0404(11) 0.0369(10) 0.0417(11) 0.0044(9) -0.0093(9) -0.0098(9)
C5 0.0485(13) 0.0452(12) 0.0457(13) 0.0027(10) -0.0142(10) -0.0078(10)
C6 0.0529(14) 0.0486(13) 0.0477(13) 0.0080(10) -0.0146(10) -0.0003(10)
C7 0.0761(17) 0.0398(12) 0.0594(16) 0.0104(11) -0.0147(13) -0.0072(12)
C8 0.0743(17) 0.0397(12) 0.0586(16) 0.0036(11) -0.0143(12) -0.0164(12)
C8A 0.0498(13) 0.0425(12) 0.0455(13) 0.0036(9) -0.0110(10) -0.0145(10)
C9 0.0459(12) 0.0439(11) 0.0358(11) 0.0027(9) -0.0091(9) -0.0144(9)
C10 0.0769(17) 0.0433(12) 0.0660(17) 0.0140(11) -0.0206(13) -0.0247(12)
C11 0.0685(16) 0.0646(15) 0.0458(14) -0.0053(11) -0.0156(11) -0.0282(13)
C1' 0.0542(13) 0.0496(13) 0.0404(13) 0.0011(10) -0.0101(10) -0.0137(10)
C2' 0.0489(12) 0.0381(10) 0.0369(11) 0.0040(8) -0.0161(9) -0.0098(9)
C3' 0.0792(18) 0.0425(12) 0.0396(12) 0.0048(9) -0.0208(11) -0.0191(12)
C4' 0.106(2) 0.0595(17) 0.071(2) -0.0180(14) -0.0161(17) -0.0186(17)
C5' 0.110(3) 0.124(3) 0.072(2) 0.001(2) 0.001(2) -0.082(3)
O1 0.0704(11) 0.0435(8) 0.0554(10) 0.0038(7) -0.0227(8) -0.0259(8)
O2 0.0756(11) 0.0541(10) 0.0493(10) 0.0106(7) -0.0310(8) -0.0190(9)
O3 0.0675(10) 0.0441(8) 0.0496(9) 0.0117(7) -0.0219(8) -0.0260(8)
O4 0.0586(10) 0.0791(12) 0.0482(10) 0.0023(9) -0.0088(8) -0.0351(9)
O5 0.1244(18) 0.0911(15) 0.0383(10) 0.0053(9) -0.0129(10) -0.0572(14)
O6 0.0820(14) 0.0566(11) 0.0808(14) -0.0026(9) -0.0388(11) -0.0264(10)
Br1 0.0946(3) 0.0709(2) 0.0656(2) 0.00877(14) -0.04236(17) 0.00734(16)
_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
C2 C3 1.340(3) . ?
C2 O1 1.371(3) . ?
C2 C11 1.486(3) . ?
C3 C9 1.480(3) . ?
C3 C4 1.502(3) . ?
C4 C4A 1.517(3) . ?
C4 C2' 1.559(3) . ?
C4 H4 0.9800 . ?
C4A C8A 1.380(3) . ?
C4A C5 1.390(3) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(4) . ?
C6 Br1 1.895(3) . ?
C7 C8 1.367(4) . ?
C7 H7 0.9300 . ?
C8 C8A 1.387(3) . ?
C8 H8 0.9300 . ?
C8A O1 1.375(3) . ?
C9 O2 1.206(3) . ?
C9 O3 1.343(3) . ?
C10 O3 1.444(3) . ?
C10 H101 0.9600 . ?
C10 H102 0.9600 . ?
C10 H103 0.9600 . ?
C11 H111 0.9600 . ?
C11 H112 0.9600 . ?
C11 H113 0.9600 . ?
C1' O5 1.194(3) . ?
C1' O4 1.331(3) . ?
C1' C2' 1.515(3) . ?
C2' C3' 1.531(3) . ?
C2' H2' 0.9800 . ?
C3' O6 1.196(3) . ?
C3' C4' 1.490(4) . ?
C4' H4'1 0.9600 . ?
C4' H4'2 0.9600 . ?
C4' H4'3 0.9600 . ?
C5' O4 1.450(3) . ?
C5' H5'1 0.9600 . ?
C5' H5'2 0.9600 . ?
C5' H5'3 0.9600 . ?
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
C3 C2 O1 122.1(2) . . ?
C3 C2 C11 129.3(2) . . ?
O1 C2 C11 108.7(2) . . ?
C2 C3 C9 119.5(2) . . ?
C2 C3 C4 123.21(18) . . ?
C9 C3 C4 117.32(19) . . ?
C3 C4 C4A 110.71(18) . . ?
C3 C4 C2' 111.00(16) . . ?
C4A C4 C2' 113.21(17) . . ?
C3 C4 H4 107.2 . . ?
C4A C4 H4 107.2 . . ?
C2' C4 H4 107.2 . . ?
C8A C4A C5 118.15(19) . . ?
C8A C4A C4 120.16(19) . . ?
C5 C4A C4 121.7(2) . . ?
C6 C5 C4A 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4A C5 H5 120.0 . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 Br1 119.5(2) . . ?
C7 C6 Br1 118.95(18) . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C8A 120.1(2) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
O1 C8A C4A 122.86(19) . . ?
O1 C8A C8 115.9(2) . . ?
C4A C8A C8 121.3(2) . . ?
O2 C9 O3 122.5(2) . . ?
O2 C9 C3 126.9(2) . . ?
O3 C9 C3 110.57(18) . . ?
O3 C10 H101 109.5 . . ?
O3 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
O3 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
C2 C11 H111 109.5 . . ?
C2 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
C2 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
O5 C1' O4 124.1(2) . . ?
O5 C1' C2' 124.6(2) . . ?
O4 C1' C2' 111.23(19) . . ?
C1' C2' C3' 109.08(19) . . ?
C1' C2' C4 112.41(17) . . ?
C3' C2' C4 113.20(19) . . ?
C1' C2' H2' 107.3 . . ?
C3' C2' H2' 107.3 . . ?
C4 C2' H2' 107.3 . . ?
O6 C3' C4' 123.1(3) . . ?
O6 C3' C2' 121.3(2) . . ?
C4' C3' C2' 115.5(3) . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
H4'2 C4' H4'3 109.5 . . ?
O4 C5' H5'1 109.5 . . ?
O4 C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
O4 C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
H5'2 C5' H5'3 109.5 . . ?
C2 O1 C8A 119.37(17) . . ?
C9 O3 C10 116.21(19) . . ?
C1' O4 C5' 116.4(2) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C9 -177.76(19) . . . . ?
C11 C2 C3 C9 1.0(4) . . . . ?
O1 C2 C3 C4 3.5(3) . . . . ?
C11 C2 C3 C4 -177.7(2) . . . . ?
C2 C3 C4 C4A -12.3(3) . . . . ?
C9 C3 C4 C4A 168.96(18) . . . . ?
C2 C3 C4 C2' 114.3(2) . . . . ?
C9 C3 C4 C2' -64.4(2) . . . . ?
C3 C4 C4A C8A 11.4(3) . . . . ?
C2' C4 C4A C8A -114.0(2) . . . . ?
C3 C4 C4A C5 -169.85(19) . . . . ?
C2' C4 C4A C5 64.8(3) . . . . ?
C8A C4A C5 C6 0.0(3) . . . . ?
C4 C4A C5 C6 -178.8(2) . . . . ?
C4A C5 C6 C7 0.8(4) . . . . ?
C4A C5 C6 Br1 -179.84(16) . . . . ?
C5 C6 C7 C8 -1.2(4) . . . . ?
Br1 C6 C7 C8 179.5(2) . . . . ?
C6 C7 C8 C8A 0.7(4) . . . . ?
C5 C4A C8A O1 178.9(2) . . . . ?
C4 C4A C8A O1 -2.3(3) . . . . ?
C5 C4A C8A C8 -0.4(3) . . . . ?
C4 C4A C8A C8 178.3(2) . . . . ?
C7 C8 C8A O1 -179.3(2) . . . . ?
C7 C8 C8A C4A 0.1(4) . . . . ?
C2 C3 C9 O2 -18.3(4) . . . . ?
C4 C3 C9 O2 160.5(2) . . . . ?
C2 C3 C9 O3 162.62(19) . . . . ?
C4 C3 C9 O3 -18.6(3) . . . . ?
O5 C1' C2' C3' 10.7(3) . . . . ?
O4 C1' C2' C3' -170.57(19) . . . . ?
O5 C1' C2' C4 -115.7(3) . . . . ?
O4 C1' C2' C4 63.0(2) . . . . ?
C3 C4 C2' C1' -103.0(2) . . . . ?
C4A C4 C2' C1' 22.2(3) . . . . ?
C3 C4 C2' C3' 132.82(18) . . . . ?
C4A C4 C2' C3' -102.0(2) . . . . ?
C1' C2' C3' O6 -113.2(2) . . . . ?
C4 C2' C3' O6 12.7(3) . . . . ?
C1' C2' C3' C4' 69.7(3) . . . . ?
C4 C2' C3' C4' -164.3(2) . . . . ?
C3 C2 O1 C8A 7.3(3) . . . . ?
C11 C2 O1 C8A -171.69(19) . . . . ?
C4A C8A O1 C2 -7.8(3) . . . . ?
C8 C8A O1 C2 171.6(2) . . . . ?
O2 C9 O3 C10 -0.6(3) . . . . ?
C3 C9 O3 C10 178.6(2) . . . . ?
O5 C1' O4 C5' 5.4(4) . . . . ?
C2' C1' O4 C5' -173.3(2) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5' H5'3 O5 0.96 2.56 3.341(4) 138.8 2_666
C5' H5'1 Br1 0.96 3.00 3.910(4) 158.2 2_666
C4' H4'2 O5 0.96 2.59 3.114(4) 114.8 .
C2' H2' O2 0.98 2.35 3.305(3) 164.9 2_657
C11 H112 O2 0.96 2.30 2.856(3) 116.5 .
_refine_diff_density_max 0.361
_refine_diff_density_min -0.771
_refine_diff_density_rms 0.058
_shelxl_version_number 2013-3
_shelx_res_file
;
TITL AP13003TA_01_0m in P-1
CELL 0.71073 8.5665 9.1041 12.5319 77.751 74.492 66.840
ZERR 2.00 0.0003 0.0003 0.0004 0.002 0.002 0.002
LATT 1
SFAC C H O Br
UNIT 34 34 12 2
OMIT 0 1 0
OMIT 1 0 1
OMIT 0 1 1
OMIT 0 0 1
L.S. 5
ACTA
BOND $H
FMAP 2
PLAN 5
HTAB C5' O5_$1
HTAB C5' Br1_$1
HTAB C4' O5
HTAB C2' O2_$2
HTAB C11 O2
EQIV $2 -x+1, -y, -z+2
EQIV $1 -x+1, -y+1, -z+1
CONF
HTAB
SIZE 0.200 0.250 0.350
TEMP 23.000
WGHT 0.057000 0.134000
FVAR 0.25052
C2 1 0.267836 0.424775 0.992270 11.00000 0.04432 0.04819 =
0.03968 0.00019 -0.00859 -0.01739
C3 1 0.248858 0.303540 0.958760 11.00000 0.04193 0.04243 =
0.03454 0.00371 -0.00899 -0.01393
C4 1 0.203413 0.315410 0.848679 11.00000 0.04004 0.03782 =
0.04004 0.00583 -0.01362 -0.01331
AFIX 13
H4 2 0.104452 0.280072 0.863974 11.00000 -1.20000
AFIX 0
C4A 1 0.145147 0.488742 0.795044 11.00000 0.04042 0.03688 =
0.04173 0.00438 -0.00926 -0.00981
C5 1 0.070827 0.534734 0.701647 11.00000 0.04852 0.04516 =
0.04572 0.00274 -0.01419 -0.00776
AFIX 43
H5 2 0.053697 0.458783 0.671343 11.00000 -1.20000
AFIX 0
C6 1 0.022623 0.692422 0.654037 11.00000 0.05291 0.04859 =
0.04774 0.00795 -0.01462 -0.00034
C7 1 0.048080 0.807622 0.695914 11.00000 0.07614 0.03976 =
0.05942 0.01041 -0.01473 -0.00724
AFIX 43
H7 2 0.016716 0.913471 0.662024 11.00000 -1.20000
AFIX 0
C8 1 0.120230 0.763725 0.788134 11.00000 0.07435 0.03972 =
0.05855 0.00358 -0.01431 -0.01642
AFIX 43
H8 2 0.137115 0.840311 0.817908 11.00000 -1.20000
AFIX 0
C8A 1 0.168310 0.605158 0.837391 11.00000 0.04981 0.04250 =
0.04554 0.00363 -0.01103 -0.01454
C9 1 0.276778 0.148093 1.031262 11.00000 0.04591 0.04386 =
0.03579 0.00268 -0.00914 -0.01445
C10 1 0.227965 -0.097611 1.063304 11.00000 0.07694 0.04330 =
0.06604 0.01396 -0.02064 -0.02472
AFIX 137
H101 2 0.171547 -0.149925 1.035622 11.00000 -1.50000
H102 2 0.177446 -0.086043 1.140675 11.00000 -1.50000
H103 2 0.349339 -0.161194 1.055261 11.00000 -1.50000
AFIX 0
C11 1 0.317817 0.429123 1.096020 11.00000 0.06846 0.06462 =
0.04578 -0.00528 -0.01565 -0.02817
AFIX 137
H111 2 0.441063 0.402075 1.082514 11.00000 -1.50000
H112 2 0.284714 0.352911 1.154092 11.00000 -1.50000
H113 2 0.259963 0.535190 1.118479 11.00000 -1.50000
AFIX 0
C1' 1 0.457154 0.286252 0.681555 11.00000 0.05421 0.04965 =
0.04043 0.00114 -0.01014 -0.01369
C2' 1 0.355477 0.199103 0.771435 11.00000 0.04888 0.03815 =
0.03689 0.00401 -0.01606 -0.00978
AFIX 13
H2' 2 0.435390 0.123229 0.818223 11.00000 -1.20000
AFIX 0
C3' 1 0.296594 0.099951 0.716806 11.00000 0.07920 0.04252 =
0.03961 0.00476 -0.02083 -0.01914
C4' 1 0.436993 -0.042091 0.667438 11.00000 0.10614 0.05954 =
0.07060 -0.01799 -0.01609 -0.01860
AFIX 137
H4'1 2 0.474446 -0.126023 0.726064 11.00000 -1.50000
H4'2 2 0.533080 -0.011624 0.624786 11.00000 -1.50000
H4'3 2 0.393917 -0.080149 0.619653 11.00000 -1.50000
AFIX 0
C5' 1 0.618279 0.456560 0.648736 11.00000 0.11038 0.12415 =
0.07247 0.00115 0.00074 -0.08178
AFIX 137
H5'1 2 0.712936 0.393019 0.596997 11.00000 -1.50000
H5'2 2 0.661601 0.505014 0.689644 11.00000 -1.50000
H5'3 2 0.536651 0.539267 0.608640 11.00000 -1.50000
AFIX 0
O1 3 0.237990 0.573116 0.930434 11.00000 0.07044 0.04350 =
0.05545 0.00378 -0.02267 -0.02585
O2 3 0.352998 0.101243 1.107153 11.00000 0.07560 0.05411 =
0.04925 0.01058 -0.03105 -0.01899
O3 3 0.206243 0.059368 1.000644 11.00000 0.06750 0.04410 =
0.04958 0.01170 -0.02189 -0.02598
O4 3 0.533161 0.354419 0.725662 11.00000 0.05863 0.07907 =
0.04821 0.00229 -0.00878 -0.03508
O5 3 0.465807 0.295459 0.583792 11.00000 0.12441 0.09110 =
0.03829 0.00534 -0.01292 -0.05723
O6 3 0.146440 0.132433 0.718549 11.00000 0.08202 0.05658 =
0.08083 -0.00264 -0.03882 -0.02637
BR1 4 -0.079107 0.753364 0.526916 11.00000 0.09465 0.07086 =
0.06556 0.00877 -0.04236 0.00734
HKLF 4
REM AP13003TA_01_0m in P-1
REM R1 = 0.0433 for 2920 Fo > 4sig(Fo) and 0.0908 for all 5224 data
REM 221 parameters refined using 0 restraints
END
WGHT 0.0570 0.1355
REM Instructions for potential hydrogen bonds
HTAB C11 O2
HTAB C2' O2_$2
HTAB C4' O5
HTAB C5' Br1_$1
HTAB C5' O5_$1
REM Highest difference peak 0.361, deepest hole -0.771, 1-sigma level 0.058
Q1 1 0.0094 0.7368 0.4998 11.00000 0.05 0.36
Q2 1 -0.1395 0.6920 0.5237 11.00000 0.05 0.32
Q3 1 -0.1247 0.8346 0.5565 11.00000 0.05 0.29
Q4 1 0.6181 0.4331 0.5689 11.00000 0.05 0.22
Q5 1 0.4129 0.2349 0.7323 11.00000 0.05 0.21
;
_shelx_res_checksum 97513
_database_code_depnum_ccdc_archive 'CCDC 952578'
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_cpd4
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C17 H17 Cl O6'
_chemical_formula_sum 'C17 H17 Cl O6'
_chemical_formula_weight 352.76
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'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.4753(3)
_cell_length_b 9.1065(3)
_cell_length_c 12.4545(4)
_cell_angle_alpha 78.551(2)
_cell_angle_beta 75.245(2)
_cell_angle_gamma 66.078(2)
_cell_volume 844.75(5)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used ?
_cell_measurement_theta_min ?
_cell_measurement_theta_max ?
_exptl_crystal_description ?
_exptl_crystal_colour ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.387
_exptl_crystal_F_000 368
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.400
_exptl_crystal_size_mid 0.200
_exptl_crystal_size_min 0.200
_exptl_absorpt_coefficient_mu 0.255
_shelx_estimated_absorpt_T_min 0.905
_shelx_estimated_absorpt_T_max 0.951
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.941
_exptl_absorpt_correction_T_max 0.950
_exptl_absorpt_process_details '(SADABS; Bruker, 2008)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source ?
_diffrn_measurement_device_type ?
_diffrn_measurement_method ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 8270
_diffrn_reflns_av_unetI/netI 0.0317
_diffrn_reflns_av_R_equivalents 0.0165
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 3.403
_diffrn_reflns_theta_max 30.543
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total 5120
_reflns_number_gt 3500
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection ?
_computing_cell_refinement ?
_computing_data_reduction ?
_computing_structure_solution ?
_computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0794P)^2^+0.1114P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 5120
_refine_ls_number_parameters 221
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0761
_refine_ls_R_factor_gt 0.0504
_refine_ls_wR_factor_ref 0.1585
_refine_ls_wR_factor_gt 0.1389
_refine_ls_goodness_of_fit_ref 1.040
_refine_ls_restrained_S_all 1.040
_refine_ls_shift/su_max 0.000
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.76685(19) 0.42721(18) 0.48826(12) 0.0403(3) Uani 1 1 d . . . . .
C3 C 0.74742(18) 0.30530(17) 0.45550(11) 0.0367(3) Uani 1 1 d . . . . .
C4 C 0.70131(18) 0.31512(16) 0.34414(11) 0.0360(3) Uani 1 1 d . . . . .
H4 H 0.6013 0.2811 0.3587 0.043 Uiso 1 1 calc R U . . .
C4A C 0.64207(18) 0.48756(17) 0.29021(12) 0.0385(3) Uani 1 1 d . . . . .
C5 C 0.5654(2) 0.53187(19) 0.19624(13) 0.0469(4) Uani 1 1 d . . . . .
H5 H 0.5472 0.4554 0.1664 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5162(2) 0.6905(2) 0.14737(14) 0.0563(5) Uani 1 1 d . . . . .
C7 C 0.5431(3) 0.8059(2) 0.18908(16) 0.0645(5) Uani 1 1 d . . . . .
H7 H 0.5111 0.9114 0.1547 0.077 Uiso 1 1 calc R U . . .
C8 C 0.6175(3) 0.7635(2) 0.28158(16) 0.0573(4) Uani 1 1 d . . . . .
H8 H 0.6357 0.8404 0.3109 0.069 Uiso 1 1 calc R U . . .
C8A C 0.6657(2) 0.60508(18) 0.33149(13) 0.0428(3) Uani 1 1 d . . . . .
C9 C 0.77501(19) 0.15149(18) 0.52852(12) 0.0395(3) Uani 1 1 d . . . . .
C10 C 0.7265(3) -0.0933(2) 0.56071(17) 0.0593(5) Uani 1 1 d . . . . .
H103 H 0.8494 -0.1602 0.5506 0.089 Uiso 1 1 calc R U . . .
H102 H 0.6648 -0.1436 0.5351 0.089 Uiso 1 1 calc R U . . .
H101 H 0.6803 -0.0798 0.6385 0.089 Uiso 1 1 calc R U . . .
C11 C 0.8172(2) 0.4336(2) 0.59321(14) 0.0532(4) Uani 1 1 d . . . . .
H113 H 0.7743 0.3664 0.6530 0.080 Uiso 1 1 calc R U . . .
H112 H 0.7666 0.5430 0.6115 0.080 Uiso 1 1 calc R U . . .
H111 H 0.9430 0.3954 0.5827 0.080 Uiso 1 1 calc R U . . .
C1' C 0.9595(2) 0.27831(19) 0.17872(13) 0.0460(4) Uani 1 1 d . . . . .
C2' C 0.85683(19) 0.19506(17) 0.26761(12) 0.0398(3) Uani 1 1 d . . . . .
H2' H 0.9378 0.1195 0.3153 0.048 Uiso 1 1 calc R U . . .
C3' C 0.7968(3) 0.09466(19) 0.21355(13) 0.0509(4) Uani 1 1 d . . . . .
C4' C 0.9400(3) -0.0503(3) 0.16412(19) 0.0777(6) Uani 1 1 d . . . . .
H4'1 H 0.9700 -0.1378 0.2221 0.117 Uiso 1 1 calc R U . . .
H4'2 H 1.0417 -0.0246 0.1287 0.117 Uiso 1 1 calc R U . . .
H4'3 H 0.9003 -0.0816 0.1099 0.117 Uiso 1 1 calc R U . . .
C5' C 1.1265(4) 0.4422(4) 0.1472(2) 0.0954(9) Uani 1 1 d . . . . .
H5'1 H 1.0437 0.5287 0.1083 0.143 Uiso 1 1 calc R U . . .
H5'2 H 1.2187 0.3759 0.0944 0.143 Uiso 1 1 calc R U . . .
H5'3 H 1.1760 0.4861 0.1882 0.143 Uiso 1 1 calc R U . . .
O1 O 0.73776(17) 0.57433(13) 0.42527(10) 0.0501(3) Uani 1 1 d . . . . .
O2 O 0.85203(17) 0.10569(15) 0.60569(10) 0.0557(3) Uani 1 1 d . . . . .
O3 O 0.70372(15) 0.06275(13) 0.49748(9) 0.0484(3) Uani 1 1 d . . . . .
O4 O 1.03786(16) 0.34544(17) 0.22384(10) 0.0577(3) Uani 1 1 d . . . . .
O5 O 0.9672(2) 0.2872(2) 0.08052(11) 0.0760(4) Uani 1 1 d . . . . .
O6 O 0.6435(2) 0.12798(16) 0.21538(12) 0.0665(4) Uani 1 1 d . . . . .
Cl1 Cl 0.41850(8) 0.74407(7) 0.03139(5) 0.0874(2) Uani 1 1 d . . . . .
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
C2 0.0399(7) 0.0439(7) 0.0354(7) -0.0005(6) -0.0069(6) -0.0159(6)
C3 0.0375(7) 0.0401(7) 0.0303(6) 0.0025(5) -0.0071(5) -0.0148(5)
C4 0.0386(7) 0.0363(6) 0.0330(6) 0.0032(5) -0.0112(5) -0.0144(5)
C4A 0.0352(7) 0.0375(7) 0.0365(7) 0.0044(5) -0.0082(5) -0.0101(5)
C5 0.0435(8) 0.0454(8) 0.0423(8) 0.0021(6) -0.0125(6) -0.0075(6)
C6 0.0527(9) 0.0514(9) 0.0410(8) 0.0068(7) -0.0124(7) 0.0010(7)
C7 0.0746(12) 0.0403(8) 0.0545(10) 0.0095(7) -0.0098(9) -0.0055(8)
C8 0.0695(11) 0.0375(8) 0.0553(10) 0.0028(7) -0.0092(9) -0.0155(7)
C8A 0.0432(8) 0.0398(7) 0.0401(8) 0.0019(6) -0.0072(6) -0.0135(6)
C9 0.0400(7) 0.0416(7) 0.0327(7) 0.0022(5) -0.0074(6) -0.0137(6)
C10 0.0702(11) 0.0425(8) 0.0650(11) 0.0111(8) -0.0192(9) -0.0250(8)
C11 0.0620(10) 0.0626(10) 0.0423(8) -0.0063(7) -0.0150(8) -0.0274(8)
C1' 0.0495(8) 0.0466(8) 0.0364(7) -0.0028(6) -0.0068(6) -0.0139(6)
C2' 0.0452(7) 0.0366(7) 0.0331(7) 0.0025(5) -0.0135(6) -0.0102(6)
C3' 0.0744(12) 0.0405(8) 0.0396(8) 0.0040(6) -0.0191(8) -0.0224(7)
C4' 0.1055(18) 0.0563(11) 0.0674(13) -0.0203(10) -0.0117(12) -0.0230(11)
C5' 0.106(2) 0.133(2) 0.0730(15) -0.0012(16) 0.0042(14) -0.0876(19)
O1 0.0663(7) 0.0424(6) 0.0487(6) 0.0028(5) -0.0188(5) -0.0264(5)
O2 0.0688(8) 0.0537(7) 0.0451(6) 0.0093(5) -0.0281(6) -0.0201(6)
O3 0.0594(7) 0.0426(6) 0.0468(6) 0.0100(5) -0.0191(5) -0.0240(5)
O4 0.0557(7) 0.0771(9) 0.0466(6) -0.0001(6) -0.0078(5) -0.0354(6)
O5 0.1155(12) 0.0886(10) 0.0345(6) 0.0027(6) -0.0095(7) -0.0562(9)
O6 0.0815(10) 0.0570(8) 0.0759(9) -0.0017(7) -0.0370(8) -0.0307(7)
Cl1 0.0922(4) 0.0776(4) 0.0571(3) 0.0072(2) -0.0378(3) 0.0109(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.337(2) . ?
C2 O1 1.3728(18) . ?
C2 C11 1.493(2) . ?
C3 C9 1.4767(19) . ?
C3 C4 1.5109(19) . ?
C4 C4A 1.5109(18) . ?
C4 C2' 1.564(2) . ?
C4 H4 0.9800 . ?
C4A C8A 1.376(2) . ?
C4A C5 1.394(2) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(3) . ?
C6 Cl1 1.7356(18) . ?
C7 C8 1.367(3) . ?
C7 H7 0.9300 . ?
C8 C8A 1.390(2) . ?
C8 H8 0.9300 . ?
C8A O1 1.382(2) . ?
C9 O2 1.2097(18) . ?
C9 O3 1.3441(19) . ?
C10 O3 1.4449(19) . ?
C10 H103 0.9600 . ?
C10 H102 0.9600 . ?
C10 H101 0.9600 . ?
C11 H113 0.9600 . ?
C11 H112 0.9600 . ?
C11 H111 0.9600 . ?
C1' O5 1.196(2) . ?
C1' O4 1.336(2) . ?
C1' C2' 1.506(2) . ?
C2' C3' 1.531(2) . ?
C2' H2' 0.9800 . ?
C3' O6 1.204(2) . ?
C3' C4' 1.496(3) . ?
C4' H4'1 0.9600 . ?
C4' H4'2 0.9600 . ?
C4' H4'3 0.9600 . ?
C5' O4 1.445(2) . ?
C5' H5'1 0.9600 . ?
C5' H5'2 0.9600 . ?
C5' H5'3 0.9600 . ?
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
C3 C2 O1 122.35(13) . . ?
C3 C2 C11 128.98(14) . . ?
O1 C2 C11 108.66(14) . . ?
C2 C3 C9 119.90(13) . . ?
C2 C3 C4 122.91(12) . . ?
C9 C3 C4 117.17(13) . . ?
C4A C4 C3 110.55(12) . . ?
C4A C4 C2' 113.21(11) . . ?
C3 C4 C2' 110.91(11) . . ?
C4A C4 H4 107.3 . . ?
C3 C4 H4 107.3 . . ?
C2' C4 H4 107.3 . . ?
C8A C4A C5 118.04(13) . . ?
C8A C4A C4 120.70(13) . . ?
C5 C4A C4 121.24(14) . . ?
C6 C5 C4A 119.71(17) . . ?
C6 C5 H5 120.1 . . ?
C4A C5 H5 120.1 . . ?
C7 C6 C5 121.37(16) . . ?
C7 C6 Cl1 119.53(13) . . ?
C5 C6 Cl1 119.10(16) . . ?
C8 C7 C6 119.26(16) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C8A 119.64(18) . . ?
C7 C8 H8 120.2 . . ?
C8A C8 H8 120.2 . . ?
C4A C8A O1 122.58(13) . . ?
C4A C8A C8 121.97(16) . . ?
O1 C8A C8 115.44(15) . . ?
O2 C9 O3 122.56(14) . . ?
O2 C9 C3 126.66(15) . . ?
O3 C9 C3 110.78(12) . . ?
O3 C10 H103 109.5 . . ?
O3 C10 H102 109.5 . . ?
H103 C10 H102 109.5 . . ?
O3 C10 H101 109.5 . . ?
H103 C10 H101 109.5 . . ?
H102 C10 H101 109.5 . . ?
C2 C11 H113 109.5 . . ?
C2 C11 H112 109.5 . . ?
H113 C11 H112 109.5 . . ?
C2 C11 H111 109.5 . . ?
H113 C11 H111 109.5 . . ?
H112 C11 H111 109.5 . . ?
O5 C1' O4 124.00(16) . . ?
O5 C1' C2' 124.82(16) . . ?
O4 C1' C2' 111.16(13) . . ?
C1' C2' C3' 109.67(13) . . ?
C1' C2' C4 112.64(12) . . ?
C3' C2' C4 112.69(13) . . ?
C1' C2' H2' 107.2 . . ?
C3' C2' H2' 107.2 . . ?
C4 C2' H2' 107.2 . . ?
O6 C3' C4' 122.96(18) . . ?
O6 C3' C2' 121.50(16) . . ?
C4' C3' C2' 115.48(17) . . ?
C3' C4' H4'1 109.5 . . ?
C3' C4' H4'2 109.5 . . ?
H4'1 C4' H4'2 109.5 . . ?
C3' C4' H4'3 109.5 . . ?
H4'1 C4' H4'3 109.5 . . ?
H4'2 C4' H4'3 109.5 . . ?
O4 C5' H5'1 109.5 . . ?
O4 C5' H5'2 109.5 . . ?
H5'1 C5' H5'2 109.5 . . ?
O4 C5' H5'3 109.5 . . ?
H5'1 C5' H5'3 109.5 . . ?
H5'2 C5' H5'3 109.5 . . ?
C2 O1 C8A 119.12(12) . . ?
C9 O3 C10 116.12(13) . . ?
C1' O4 C5' 116.22(16) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C9 -178.02(13) . . . . ?
C11 C2 C3 C9 0.8(2) . . . . ?
O1 C2 C3 C4 3.3(2) . . . . ?
C11 C2 C3 C4 -177.90(15) . . . . ?
C2 C3 C4 C4A -12.65(19) . . . . ?
C9 C3 C4 C4A 168.64(12) . . . . ?
C2 C3 C4 C2' 113.77(15) . . . . ?
C9 C3 C4 C2' -64.93(16) . . . . ?
C3 C4 C4A C8A 11.95(19) . . . . ?
C2' C4 C4A C8A -113.18(15) . . . . ?
C3 C4 C4A C5 -169.34(13) . . . . ?
C2' C4 C4A C5 65.53(18) . . . . ?
C8A C4A C5 C6 0.2(2) . . . . ?
C4 C4A C5 C6 -178.53(14) . . . . ?
C4A C5 C6 C7 0.7(3) . . . . ?
C4A C5 C6 Cl1 -179.25(12) . . . . ?
C5 C6 C7 C8 -1.0(3) . . . . ?
Cl1 C6 C7 C8 178.92(14) . . . . ?
C6 C7 C8 C8A 0.4(3) . . . . ?
C5 C4A C8A O1 178.89(14) . . . . ?
C4 C4A C8A O1 -2.4(2) . . . . ?
C5 C4A C8A C8 -0.8(2) . . . . ?
C4 C4A C8A C8 177.99(14) . . . . ?
C7 C8 C8A C4A 0.4(3) . . . . ?
C7 C8 C8A O1 -179.23(16) . . . . ?
C2 C3 C9 O2 -18.0(2) . . . . ?
C4 C3 C9 O2 160.77(15) . . . . ?
C2 C3 C9 O3 162.85(13) . . . . ?
C4 C3 C9 O3 -18.40(18) . . . . ?
O5 C1' C2' C3' 11.8(2) . . . . ?
O4 C1' C2' C3' -169.94(14) . . . . ?
O5 C1' C2' C4 -114.58(19) . . . . ?
O4 C1' C2' C4 63.70(17) . . . . ?
C4A C4 C2' C1' 22.09(17) . . . . ?
C3 C4 C2' C1' -102.84(14) . . . . ?
C4A C4 C2' C3' -102.63(14) . . . . ?
C3 C4 C2' C3' 132.43(12) . . . . ?
C1' C2' C3' O6 -113.98(18) . . . . ?
C4 C2' C3' O6 12.4(2) . . . . ?
C1' C2' C3' C4' 68.90(18) . . . . ?
C4 C2' C3' C4' -164.77(15) . . . . ?
C3 C2 O1 C8A 8.0(2) . . . . ?
C11 C2 O1 C8A -171.02(13) . . . . ?
C4A C8A O1 C2 -8.4(2) . . . . ?
C8 C8A O1 C2 171.26(14) . . . . ?
O2 C9 O3 C10 -1.0(2) . . . . ?
C3 C9 O3 C10 178.26(14) . . . . ?
O5 C1' O4 C5' 4.0(3) . . . . ?
C2' C1' O4 C5' -174.25(18) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5' H5'2 Cl1 0.96 2.93 3.811(3) 152.5 2_765
C5' H5'1 O5 0.96 2.60 3.396(3) 140.3 2_765
C4' H4'2 O5 0.96 2.62 3.125(3) 112.9 .
C2' H2' O2 0.98 2.34 3.2965(17) 165.1 2_756
C11 H113 O2 0.96 2.35 2.855(2) 112.5 .
_refine_diff_density_max 0.248
_refine_diff_density_min -0.378
_refine_diff_density_rms 0.044
_shelxl_version_number 2013-3
_shelx_res_file
;
TITL AP13003TA_02_0m in P-1
CELL 0.71073 8.4753 9.1065 12.4545 78.551 75.245 66.078
ZERR 2.00 0.0003 0.0003 0.0004 0.002 0.002 0.002
LATT 1
SFAC C H O Cl
UNIT 34 34 12 2
OMIT 0 1 0
OMIT 1 0 0
OMIT 0 1 1
OMIT 1 0 1
OMIT 0 0 1
OMIT 0 -1 1
L.S. 5
ACTA
BOND $H
FMAP 2
PLAN 5
HTAB C5' Cl1_$1
HTAB C5' O5_$1
HTAB C4' O5
HTAB C2' O2_$2
HTAB C11 O2
EQIV $2 -x+2, -y, -z+1
EQIV $1 -x+2, -y+1, -z
SIZE 0.200 0.200 0.400
HTAB
CONF
TEMP 23.000
WGHT 0.079400 0.111400
FVAR 0.28078
C2 1 0.766847 0.427212 0.488255 11.00000 0.03990 0.04394 =
0.03543 -0.00052 -0.00690 -0.01588
C3 1 0.747421 0.305296 0.455502 11.00000 0.03747 0.04014 =
0.03028 0.00246 -0.00706 -0.01483
C4 1 0.701306 0.315123 0.344141 11.00000 0.03864 0.03629 =
0.03296 0.00316 -0.01121 -0.01441
AFIX 13
H4 2 0.601258 0.281087 0.358725 11.00000 -1.20000
AFIX 0
C4A 1 0.642073 0.487561 0.290208 11.00000 0.03516 0.03747 =
0.03647 0.00444 -0.00818 -0.01015
C5 1 0.565358 0.531866 0.196236 11.00000 0.04346 0.04537 =
0.04226 0.00213 -0.01254 -0.00748
AFIX 43
H5 2 0.547218 0.455380 0.166449 11.00000 -1.20000
AFIX 0
C6 1 0.516213 0.690461 0.147366 11.00000 0.05266 0.05139 =
0.04100 0.00684 -0.01238 0.00099
C7 1 0.543136 0.805886 0.189082 11.00000 0.07462 0.04031 =
0.05453 0.00947 -0.00983 -0.00555
AFIX 43
H7 2 0.511084 0.911421 0.154704 11.00000 -1.20000
AFIX 0
C8 1 0.617501 0.763542 0.281583 11.00000 0.06951 0.03749 =
0.05529 0.00276 -0.00922 -0.01551
AFIX 43
H8 2 0.635712 0.840378 0.310934 11.00000 -1.20000
AFIX 0
C8A 1 0.665714 0.605082 0.331493 11.00000 0.04320 0.03982 =
0.04011 0.00188 -0.00721 -0.01352
C9 1 0.775015 0.151485 0.528520 11.00000 0.03998 0.04161 =
0.03267 0.00216 -0.00740 -0.01367
C10 1 0.726454 -0.093306 0.560714 11.00000 0.07015 0.04248 =
0.06503 0.01115 -0.01917 -0.02501
AFIX 137
H103 2 0.849400 -0.160216 0.550577 11.00000 -1.50000
H102 2 0.664817 -0.143618 0.535101 11.00000 -1.50000
H101 2 0.680251 -0.079764 0.638477 11.00000 -1.50000
AFIX 0
C11 1 0.817188 0.433580 0.593208 11.00000 0.06196 0.06262 =
0.04225 -0.00631 -0.01496 -0.02740
AFIX 137
H113 2 0.774288 0.366449 0.652963 11.00000 -1.50000
H112 2 0.766634 0.542955 0.611473 11.00000 -1.50000
H111 2 0.943018 0.395432 0.582685 11.00000 -1.50000
AFIX 0
C1' 1 0.959538 0.278305 0.178716 11.00000 0.04953 0.04656 =
0.03635 -0.00282 -0.00682 -0.01394
C2' 1 0.856834 0.195057 0.267605 11.00000 0.04519 0.03663 =
0.03305 0.00252 -0.01349 -0.01021
AFIX 13
H2' 2 0.937791 0.119458 0.315339 11.00000 -1.20000
AFIX 0
C3' 1 0.796763 0.094663 0.213549 11.00000 0.07439 0.04049 =
0.03955 0.00396 -0.01909 -0.02239
C4' 1 0.940021 -0.050316 0.164124 11.00000 0.10552 0.05631 =
0.06736 -0.02028 -0.01172 -0.02303
AFIX 137
H4'1 2 0.969977 -0.137780 0.222120 11.00000 -1.50000
H4'2 2 1.041749 -0.024631 0.128685 11.00000 -1.50000
H4'3 2 0.900264 -0.081570 0.109851 11.00000 -1.50000
AFIX 0
C5' 1 1.126518 0.442180 0.147247 11.00000 0.10584 0.13287 =
0.07298 -0.00115 0.00418 -0.08765
AFIX 137
H5'1 2 1.043708 0.528735 0.108342 11.00000 -1.50000
H5'2 2 1.218729 0.375931 0.094372 11.00000 -1.50000
H5'3 2 1.176007 0.486134 0.188151 11.00000 -1.50000
AFIX 0
O1 3 0.737757 0.574330 0.425268 11.00000 0.06630 0.04242 =
0.04873 0.00282 -0.01881 -0.02641
O2 3 0.852030 0.105685 0.605687 11.00000 0.06877 0.05370 =
0.04513 0.00930 -0.02808 -0.02007
O3 3 0.703717 0.062751 0.497481 11.00000 0.05940 0.04255 =
0.04675 0.01005 -0.01914 -0.02404
O4 3 1.037857 0.345437 0.223841 11.00000 0.05571 0.07708 =
0.04665 -0.00015 -0.00781 -0.03536
O5 3 0.967191 0.287192 0.080517 11.00000 0.11550 0.08864 =
0.03448 0.00271 -0.00951 -0.05619
O6 3 0.643462 0.127983 0.215382 11.00000 0.08153 0.05703 =
0.07594 -0.00171 -0.03698 -0.03071
CL1 4 0.418499 0.744074 0.031386 11.00000 0.09222 0.07765 =
0.05713 0.00717 -0.03785 0.01089
HKLF 4
REM AP13003TA_02_0m in P-1
REM R1 = 0.0504 for 3500 Fo > 4sig(Fo) and 0.0761 for all 5120 data
REM 221 parameters refined using 0 restraints
END
WGHT 0.0794 0.1114
REM Instructions for potential hydrogen bonds
HTAB C11 O2
HTAB C2' O2_$2
HTAB C4' O5
HTAB C5' O5_$1
HTAB C5' Cl1_$1
REM Highest difference peak 0.248, deepest hole -0.378, 1-sigma level 0.044
Q1 1 0.6818 0.4041 0.3144 11.00000 0.05 0.24
Q2 1 0.3793 0.7934 0.0828 11.00000 0.05 0.24
Q3 1 0.7815 0.2680 0.2956 11.00000 0.05 0.23
Q4 1 0.3738 0.6814 0.0410 11.00000 0.05 0.23
Q5 1 0.7237 0.3182 0.4007 11.00000 0.05 0.22
;
_shelx_res_checksum 61179
_database_code_depnum_ccdc_archive 'CCDC 952579'