# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full CrystEngComm
_journal_coden_cambridge 1350
_journal_year ?
_journal_volume ?
_journal_page_first ?
loop_
_publ_author_name
'Jiabin Gao'
'Mohan M. Bhadbhade'
'Roger Bishop'
data_jiabin36
_database_code_depnum_ccdc_archive 'CCDC 829074'
#TrackingRef 'FormIII_cyclohexanol.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C19 H23.50 O10.50'
_chemical_formula_weight 419.88
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 11.3769(5)
_cell_length_b 8.3198(4)
_cell_length_c 21.4511(10)
_cell_angle_alpha 90.00
_cell_angle_beta 98.021(3)
_cell_angle_gamma 90.00
_cell_volume 2010.56(16)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 4430
_cell_measurement_theta_min 2.813
_cell_measurement_theta_max 25.934
_exptl_crystal_description 'Long blocks'
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.10
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.387
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 886
_exptl_absorpt_coefficient_mu 0.114
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9508
_exptl_absorpt_correction_T_max 0.9889
_exptl_absorpt_process_details 'SADABS (Bruker, 2001)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Kappa APEXII CCD Diffractometer'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 14448
_diffrn_reflns_av_R_equivalents 0.0536
_diffrn_reflns_av_sigmaI/netI 0.0522
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 3.04
_diffrn_reflns_theta_max 25.00
_reflns_number_total 3522
_reflns_number_gt 2586
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2007)'
_computing_cell_refinement 'SAINT (Bruker, 2007)'
_computing_data_reduction 'SAINT '
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL-Plus (Sheldrick, 2008)'
_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^)+(0.0963P)^2^+1.7795P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3522
_refine_ls_number_parameters 289
_refine_ls_number_restraints 52
_refine_ls_R_factor_all 0.0830
_refine_ls_R_factor_gt 0.0588
_refine_ls_wR_factor_ref 0.1808
_refine_ls_wR_factor_gt 0.1606
_refine_ls_goodness_of_fit_ref 1.031
_refine_ls_restrained_S_all 1.046
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2570(2) 0.4694(3) 0.41273(10) 0.0443(6) Uani 1 1 d . . .
H1O1 H 0.3220 0.5042 0.4039 0.067 Uiso 1 1 calc R . .
O2 O -0.05606(18) 0.1782(3) 0.17423(9) 0.0360(5) Uani 1 1 d . . .
H1O2 H -0.1260 0.1628 0.1813 0.054 Uiso 1 1 calc R . .
O3 O 0.44095(19) 0.4548(3) 0.34212(10) 0.0410(6) Uani 1 1 d . . .
O4 O 0.41927(18) 0.2744(2) 0.26276(10) 0.0368(5) Uani 1 1 d . . .
O5 O 0.1504(2) 0.1247(3) 0.47624(10) 0.0456(6) Uani 1 1 d . . .
O6 O 0.00279(19) 0.3042(3) 0.46832(9) 0.0375(5) Uani 1 1 d . . .
O7 O -0.21566(18) 0.1049(2) 0.25474(10) 0.0365(5) Uani 1 1 d . . .
O8 O -0.13706(18) 0.0761(2) 0.35685(9) 0.0349(5) Uani 1 1 d . . .
O9 O 0.1896(2) -0.0705(3) 0.18234(11) 0.0442(6) Uani 1 1 d . . .
O10 O 0.23380(19) 0.1518(2) 0.13250(9) 0.0366(5) Uani 1 1 d . . .
C1 C 0.2035(2) 0.1477(3) 0.29528(13) 0.0268(6) Uani 1 1 d . . .
H1 H 0.2520 0.0472 0.2970 0.032 Uiso 1 1 calc R . .
C2 C 0.2746(2) 0.2830(3) 0.32878(13) 0.0298(7) Uani 1 1 d . . .
C3 C 0.2203(3) 0.3469(3) 0.37446(13) 0.0300(7) Uani 1 1 d . . .
C4 C 0.1020(3) 0.2732(3) 0.37999(13) 0.0284(6) Uani 1 1 d . . .
H4 H 0.0375 0.3509 0.3642 0.034 Uiso 1 1 calc R . .
C5 C 0.0978(2) 0.1272(3) 0.33416(13) 0.0263(6) Uani 1 1 d . . .
H5 H 0.1045 0.0236 0.3580 0.032 Uiso 1 1 calc R . .
C6 C -0.0089(2) 0.1269(3) 0.28489(13) 0.0275(6) Uani 1 1 d . . .
C7 C 0.0187(2) 0.1614(3) 0.22789(13) 0.0270(6) Uani 1 1 d . . .
C8 C 0.1487(2) 0.1853(3) 0.22625(13) 0.0269(6) Uani 1 1 d . . .
H8 H 0.1648 0.2995 0.2157 0.032 Uiso 1 1 calc R . .
C9 C 0.3851(3) 0.3468(4) 0.31297(14) 0.0332(7) Uani 1 1 d . . .
C10 C 0.5265(3) 0.3327(5) 0.24197(18) 0.0492(9) Uani 1 1 d . . .
H10A H 0.5197 0.4486 0.2342 0.074 Uiso 1 1 calc R . .
H10B H 0.5387 0.2775 0.2030 0.074 Uiso 1 1 calc R . .
H10C H 0.5941 0.3115 0.2745 0.074 Uiso 1 1 calc R . .
C11 C 0.0898(3) 0.2242(4) 0.44697(14) 0.0316(7) Uani 1 1 d . . .
C12 C -0.0229(3) 0.2611(4) 0.53037(14) 0.0453(9) Uani 1 1 d . . .
H12A H -0.0610 0.1552 0.5287 0.068 Uiso 1 1 calc R . .
H12C H -0.0763 0.3413 0.5447 0.068 Uiso 1 1 calc R . .
H12B H 0.0512 0.2576 0.5598 0.068 Uiso 1 1 calc R . .
C13 C -0.1302(3) 0.1033(3) 0.29620(14) 0.0304(7) Uani 1 1 d . . .
C14 C -0.2543(3) 0.0601(4) 0.37419(17) 0.0438(8) Uani 1 1 d . . .
H14A H -0.2958 0.1633 0.3684 0.066 Uiso 1 1 calc R . .
H14B H -0.2482 0.0274 0.4184 0.066 Uiso 1 1 calc R . .
H14C H -0.2986 -0.0215 0.3476 0.066 Uiso 1 1 calc R . .
C15 C 0.1927(2) 0.0731(3) 0.17873(13) 0.0289(7) Uani 1 1 d . . .
C16 C 0.2727(3) 0.0508(5) 0.08410(15) 0.0473(9) Uani 1 1 d . . .
H16A H 0.3433 -0.0098 0.1019 0.071 Uiso 1 1 calc R . .
H16B H 0.2919 0.1182 0.0494 0.071 Uiso 1 1 calc R . .
H16C H 0.2091 -0.0243 0.0682 0.071 Uiso 1 1 calc R . .
C1H C 0.5769(8) 0.1377(9) 0.5285(3) 0.0984(12) Uani 0.65 1 d PDU . 1
H1H H 0.6590 0.1222 0.5179 0.118 Uiso 0.65 1 calc PR . 1
C1H' C 0.5010(15) 0.1456(15) 0.5405(3) 0.0987(13) Uani 0.35 1 d PDU . 2
H1H' H 0.4193 0.1626 0.5514 0.118 Uiso 0.35 1 calc PR . 2
C2H C 0.4910(5) 0.1567(6) 0.4700(2) 0.0954(11) Uani 1 1 d DU . .
H2H1 H 0.5245 0.2349 0.4424 0.115 Uiso 1 1 calc R . 1
H2H2 H 0.4172 0.2041 0.4815 0.115 Uiso 1 1 calc R . 1
C3H C 0.4587(5) 0.0059(6) 0.4324(2) 0.0901(12) Uani 1 1 d DU . .
H3H1 H 0.5273 -0.0264 0.4115 0.108 Uiso 1 1 calc R . .
H3H2 H 0.3919 0.0305 0.3991 0.108 Uiso 1 1 calc R . .
O1H O 0.5724(8) 0.2787(8) 0.5679(4) 0.1043(13) Uani 0.50 1 d PDU . .
H1OH H 0.581(6) 0.246(5) 0.6063(6) 0.060 Uiso 0.50 1 d PD . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0521(14) 0.0395(13) 0.0391(13) -0.0083(10) -0.0017(11) -0.0108(11)
O2 0.0370(12) 0.0418(12) 0.0275(11) -0.0035(9) -0.0013(9) 0.0039(10)
O3 0.0382(12) 0.0415(13) 0.0416(13) -0.0009(10) -0.0008(10) -0.0101(10)
O4 0.0322(11) 0.0396(12) 0.0397(12) -0.0003(10) 0.0091(9) -0.0043(9)
O5 0.0528(14) 0.0535(14) 0.0300(12) 0.0105(11) 0.0044(10) 0.0101(11)
O6 0.0457(13) 0.0434(12) 0.0249(11) -0.0016(9) 0.0105(9) 0.0021(10)
O7 0.0308(11) 0.0384(12) 0.0393(12) -0.0113(10) 0.0015(10) -0.0017(9)
O8 0.0361(11) 0.0360(12) 0.0350(12) 0.0003(9) 0.0130(9) -0.0041(9)
O9 0.0593(15) 0.0279(12) 0.0501(14) -0.0029(10) 0.0239(12) 0.0000(10)
O10 0.0444(12) 0.0405(12) 0.0271(11) 0.0043(9) 0.0128(9) 0.0019(10)
C1 0.0294(15) 0.0254(14) 0.0262(15) 0.0022(11) 0.0065(12) 0.0008(11)
C2 0.0295(15) 0.0315(15) 0.0270(15) 0.0034(12) -0.0005(12) -0.0023(12)
C3 0.0363(16) 0.0260(15) 0.0257(15) 0.0022(12) -0.0021(13) -0.0025(12)
C4 0.0339(15) 0.0281(15) 0.0229(14) 0.0002(12) 0.0029(12) 0.0010(12)
C5 0.0314(15) 0.0230(14) 0.0250(15) 0.0016(11) 0.0058(12) 0.0016(11)
C6 0.0298(15) 0.0238(14) 0.0289(16) -0.0020(12) 0.0039(12) -0.0007(11)
C7 0.0322(15) 0.0216(14) 0.0265(15) -0.0029(11) 0.0015(12) 0.0037(11)
C8 0.0328(15) 0.0231(14) 0.0253(15) 0.0011(11) 0.0057(12) -0.0004(11)
C9 0.0319(16) 0.0349(16) 0.0318(16) 0.0077(14) 0.0005(13) -0.0007(13)
C10 0.0370(18) 0.053(2) 0.061(2) 0.0029(18) 0.0188(16) -0.0039(16)
C11 0.0349(16) 0.0327(16) 0.0268(15) -0.0021(13) 0.0027(13) -0.0043(13)
C12 0.053(2) 0.059(2) 0.0265(17) 0.0005(15) 0.0137(15) -0.0038(17)
C13 0.0356(16) 0.0216(14) 0.0345(17) -0.0060(12) 0.0065(13) -0.0033(12)
C14 0.0398(18) 0.0464(19) 0.050(2) 0.0005(16) 0.0218(16) -0.0017(15)
C15 0.0282(15) 0.0309(17) 0.0279(16) 0.0019(12) 0.0053(12) -0.0001(12)
C16 0.053(2) 0.062(2) 0.0297(17) -0.0005(16) 0.0150(16) 0.0105(17)
C1H 0.112(3) 0.099(3) 0.084(2) 0.0043(19) 0.011(2) 0.011(2)
C1H' 0.114(3) 0.099(3) 0.083(2) 0.005(2) 0.011(2) 0.011(2)
C2H 0.111(3) 0.096(2) 0.080(2) 0.0104(18) 0.014(2) 0.013(2)
C3H 0.103(3) 0.094(2) 0.073(2) 0.0137(18) 0.013(2) 0.015(2)
O1H 0.118(3) 0.103(3) 0.090(2) 0.001(2) 0.010(2) 0.010(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.338(3) . ?
O1 H1O1 0.8400 . ?
O2 C7 1.339(3) . ?
O2 H1O2 0.8400 . ?
O3 C9 1.221(4) . ?
O4 C9 1.338(4) . ?
O4 C10 1.440(4) . ?
O5 C11 1.198(4) . ?
O6 C11 1.327(4) . ?
O6 C12 1.447(4) . ?
O7 C13 1.222(3) . ?
O8 C13 1.333(4) . ?
O8 C14 1.440(4) . ?
O9 C15 1.198(3) . ?
O10 C15 1.327(3) . ?
O10 C16 1.452(4) . ?
C1 C2 1.508(4) . ?
C1 C8 1.556(4) . ?
C1 C5 1.565(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.339(4) . ?
C2 C9 1.448(4) . ?
C3 C4 1.499(4) . ?
C4 C11 1.518(4) . ?
C4 C5 1.559(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.495(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.335(4) . ?
C6 C13 1.448(4) . ?
C7 C8 1.498(4) . ?
C8 C15 1.518(4) . ?
C8 H8 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12B 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C1H O1H 1.450(4) . ?
C1H C2H 1.487(4) . ?
C1H C3H 1.546(10) 3_656 ?
C1H H1H 1.0000 . ?
C1H' C3H 1.435(15) 3_656 ?
C1H' O1H 1.449(4) . ?
C1H' C2H 1.503(4) . ?
C1H' H1H' 1.0000 . ?
C2H C3H 1.509(4) . ?
C2H H2H1 0.9900 . ?
C2H H2H2 0.9900 . ?
C3H C1H' 1.435(15) 3_656 ?
C3H C1H 1.546(10) 3_656 ?
C3H H3H1 0.9900 . ?
C3H H3H2 0.9900 . ?
O1H H1OH 0.860(4) . ?
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 O1 H1O1 109.5 . . ?
C7 O2 H1O2 109.5 . . ?
C9 O4 C10 116.8(2) . . ?
C11 O6 C12 116.7(2) . . ?
C13 O8 C14 116.7(2) . . ?
C15 O10 C16 115.0(2) . . ?
C2 C1 C8 114.9(2) . . ?
C2 C1 C5 103.2(2) . . ?
C8 C1 C5 107.0(2) . . ?
C2 C1 H1 110.5 . . ?
C8 C1 H1 110.5 . . ?
C5 C1 H1 110.5 . . ?
C3 C2 C9 122.0(3) . . ?
C3 C2 C1 112.0(3) . . ?
C9 C2 C1 126.0(3) . . ?
O1 C3 C2 128.0(3) . . ?
O1 C3 C4 118.0(3) . . ?
C2 C3 C4 114.0(2) . . ?
C3 C4 C11 112.7(2) . . ?
C3 C4 C5 102.5(2) . . ?
C11 C4 C5 112.9(2) . . ?
C3 C4 H4 109.5 . . ?
C11 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C6 C5 C4 113.4(2) . . ?
C6 C5 C1 103.4(2) . . ?
C4 C5 C1 107.0(2) . . ?
C6 C5 H5 110.9 . . ?
C4 C5 H5 110.9 . . ?
C1 C5 H5 110.9 . . ?
C7 C6 C13 122.3(3) . . ?
C7 C6 C5 112.1(3) . . ?
C13 C6 C5 125.5(3) . . ?
C6 C7 O2 127.4(3) . . ?
C6 C7 C8 114.2(2) . . ?
O2 C7 C8 118.5(2) . . ?
C7 C8 C15 110.7(2) . . ?
C7 C8 C1 102.5(2) . . ?
C15 C8 C1 112.9(2) . . ?
C7 C8 H8 110.1 . . ?
C15 C8 H8 110.1 . . ?
C1 C8 H8 110.1 . . ?
O3 C9 O4 123.7(3) . . ?
O3 C9 C2 123.8(3) . . ?
O4 C9 C2 112.5(3) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 O6 124.7(3) . . ?
O5 C11 C4 124.1(3) . . ?
O6 C11 C4 111.3(2) . . ?
O6 C12 H12A 109.5 . . ?
O6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
O6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
O7 C13 O8 124.3(3) . . ?
O7 C13 C6 123.8(3) . . ?
O8 C13 C6 111.9(2) . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 O10 123.9(3) . . ?
O9 C15 C8 123.7(3) . . ?
O10 C15 C8 112.5(2) . . ?
O10 C16 H16A 109.5 . . ?
O10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1H C1H C2H 109.5(5) . . ?
O1H C1H C3H 106.0(6) . 3_656 ?
C2H C1H C3H 110.4(6) . 3_656 ?
O1H C1H H1H 110.3 . . ?
C2H C1H H1H 110.3 . . ?
C3H C1H H1H 110.3 3_656 . ?
C3H C1H' O1H 112.2(9) 3_656 . ?
C3H C1H' C2H 115.9(10) 3_656 . ?
O1H C1H' C2H 108.7(6) . . ?
C3H C1H' H1H' 106.5 3_656 . ?
O1H C1H' H1H' 106.5 . . ?
C2H C1H' H1H' 106.5 . . ?
C1H C2H C1H' 36.5(7) . . ?
C1H C2H C3H 116.4(5) . . ?
C1H' C2H C3H 117.7(5) . . ?
C1H C2H H2H1 108.2 . . ?
C1H' C2H H2H1 131.3 . . ?
C3H C2H H2H1 108.2 . . ?
C1H C2H H2H2 108.2 . . ?
C1H' C2H H2H2 73.8 . . ?
C3H C2H H2H2 108.2 . . ?
H2H1 C2H H2H2 107.3 . . ?
C1H' C3H C2H 118.3(4) 3_656 . ?
C1H' C3H C1H 36.4(6) 3_656 3_656 ?
C2H C3H C1H 114.6(4) . 3_656 ?
C1H' C3H H3H1 73.7 3_656 . ?
C2H C3H H3H1 108.6 . . ?
C1H C3H H3H1 108.6 3_656 . ?
C1H' C3H H3H2 130.1 3_656 . ?
C2H C3H H3H2 108.6 . . ?
C1H C3H H3H2 108.6 3_656 . ?
H3H1 C3H H3H2 107.6 . . ?
C1H' O1H C1H 37.7(7) . . ?
C1H' O1H H1OH 97.5(5) . . ?
C1H O1H H1OH 107(3) . . ?
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 C1 C2 C3 110.5(3) . . . . ?
C5 C1 C2 C3 -5.6(3) . . . . ?
C8 C1 C2 C9 -66.1(4) . . . . ?
C5 C1 C2 C9 177.8(3) . . . . ?
C9 C2 C3 O1 -2.2(5) . . . . ?
C1 C2 C3 O1 -179.0(3) . . . . ?
C9 C2 C3 C4 175.0(2) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
O1 C3 C4 C11 -52.6(3) . . . . ?
C2 C3 C4 C11 130.0(3) . . . . ?
O1 C3 C4 C5 -174.2(2) . . . . ?
C2 C3 C4 C5 8.3(3) . . . . ?
C3 C4 C5 C6 -124.6(2) . . . . ?
C11 C4 C5 C6 113.9(3) . . . . ?
C3 C4 C5 C1 -11.2(3) . . . . ?
C11 C4 C5 C1 -132.7(2) . . . . ?
C2 C1 C5 C6 130.4(2) . . . . ?
C8 C1 C5 C6 8.8(3) . . . . ?
C2 C1 C5 C4 10.4(3) . . . . ?
C8 C1 C5 C4 -111.2(2) . . . . ?
C4 C5 C6 C7 108.6(3) . . . . ?
C1 C5 C6 C7 -7.0(3) . . . . ?
C4 C5 C6 C13 -67.6(3) . . . . ?
C1 C5 C6 C13 176.8(2) . . . . ?
C13 C6 C7 O2 -0.5(4) . . . . ?
C5 C6 C7 O2 -176.7(2) . . . . ?
C13 C6 C7 C8 178.6(2) . . . . ?
C5 C6 C7 C8 2.3(3) . . . . ?
C6 C7 C8 C15 124.2(3) . . . . ?
O2 C7 C8 C15 -56.6(3) . . . . ?
C6 C7 C8 C1 3.5(3) . . . . ?
O2 C7 C8 C1 -177.3(2) . . . . ?
C2 C1 C8 C7 -121.4(2) . . . . ?
C5 C1 C8 C7 -7.5(3) . . . . ?
C2 C1 C8 C15 119.4(3) . . . . ?
C5 C1 C8 C15 -126.7(2) . . . . ?
C10 O4 C9 O3 -1.8(4) . . . . ?
C10 O4 C9 C2 178.1(2) . . . . ?
C3 C2 C9 O3 5.1(5) . . . . ?
C1 C2 C9 O3 -178.6(3) . . . . ?
C3 C2 C9 O4 -174.9(3) . . . . ?
C1 C2 C9 O4 1.5(4) . . . . ?
C12 O6 C11 O5 -3.0(4) . . . . ?
C12 O6 C11 C4 176.2(2) . . . . ?
C3 C4 C11 O5 -62.8(4) . . . . ?
C5 C4 C11 O5 52.8(4) . . . . ?
C3 C4 C11 O6 118.1(3) . . . . ?
C5 C4 C11 O6 -126.4(3) . . . . ?
C14 O8 C13 O7 -4.8(4) . . . . ?
C14 O8 C13 C6 176.5(2) . . . . ?
C7 C6 C13 O7 3.7(4) . . . . ?
C5 C6 C13 O7 179.5(3) . . . . ?
C7 C6 C13 O8 -177.6(3) . . . . ?
C5 C6 C13 O8 -1.9(4) . . . . ?
C16 O10 C15 O9 1.8(4) . . . . ?
C16 O10 C15 C8 -177.5(2) . . . . ?
C7 C8 C15 O9 -61.8(3) . . . . ?
C1 C8 C15 O9 52.6(4) . . . . ?
C7 C8 C15 O10 117.6(3) . . . . ?
C1 C8 C15 O10 -128.1(2) . . . . ?
O1H C1H C2H C1H' -61.9(7) . . . . ?
C3H C1H C2H C1H' 54.5(11) 3_656 . . . ?
O1H C1H C2H C3H -163.5(7) . . . . ?
C3H C1H C2H C3H -47.1(9) 3_656 . . . ?
C3H C1H' C2H C1H -65.9(14) 3_656 . . . ?
O1H C1H' C2H C1H 61.5(7) . . . . ?
C3H C1H' C2H C3H 31.9(14) 3_656 . . . ?
O1H C1H' C2H C3H 159.3(9) . . . . ?
C1H C2H C3H C1H' 8.4(11) . . . 3_656 ?
C1H' C2H C3H C1H' -32.7(16) . . . 3_656 ?
C1H C2H C3H C1H 49.1(10) . . . 3_656 ?
C1H' C2H C3H C1H 7.9(11) . . . 3_656 ?
C3H C1H' O1H C1H 68.2(14) 3_656 . . . ?
C2H C1H' O1H C1H -61.2(7) . . . . ?
C2H C1H O1H C1H' 62.9(7) . . . . ?
C3H C1H O1H C1H' -56.2(11) 3_656 . . . ?
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
O1 H1O1 O3 0.84 2.06 2.752(3) 138.8 .
O2 H1O2 O7 0.84 2.05 2.743(3) 139.4 .
O1 H1O1 O1H 0.84 2.21 2.848(8) 133.1 3_666
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.552
_refine_diff_density_min -0.955
_refine_diff_density_rms 0.061
# Attachment 'FormIII_p-xylene.cif'
data_jaibin18
_database_code_depnum_ccdc_archive 'CCDC 829075'
#TrackingRef 'FormIII_p-xylene.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C20 H23 O10'
_chemical_formula_weight 423.38
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 11.0883(5)
_cell_length_b 8.5689(3)
_cell_length_c 21.5332(9)
_cell_angle_alpha 90.00
_cell_angle_beta 93.1040(10)
_cell_angle_gamma 90.00
_cell_volume 2042.97(14)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 9898
_cell_measurement_theta_min 2.559
_cell_measurement_theta_max 30.577
_exptl_crystal_description Blocks
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.46
_exptl_crystal_size_mid 0.44
_exptl_crystal_size_min 0.37
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.377
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 892
_exptl_absorpt_coefficient_mu 0.111
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.9509
_exptl_absorpt_correction_T_max 0.9596
_exptl_absorpt_process_details 'SADABS (Bruker, 2001)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Kappa APEXII CCD Diffractometer'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 14126
_diffrn_reflns_av_R_equivalents 0.0452
_diffrn_reflns_av_sigmaI/netI 0.0326
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_reflns_theta_min 2.57
_diffrn_reflns_theta_max 25.00
_reflns_number_total 3587
_reflns_number_gt 3242
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2007)'
_computing_cell_refinement 'SAINT (Bruker, 2007)'
_computing_data_reduction 'SAINT '
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL-Plus (Sheldrick, 2008)'
_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^)+(0.0494P)^2^+0.7618P] 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 3587
_refine_ls_number_parameters 276
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0393
_refine_ls_R_factor_gt 0.0355
_refine_ls_wR_factor_ref 0.1003
_refine_ls_wR_factor_gt 0.0953
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_restrained_S_all 1.046
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56662(9) 0.62450(12) 0.31701(4) 0.0336(3) Uani 1 1 d . . .
H1O1 H 0.6381 0.6084 0.3076 0.050 Uiso 1 1 calc R . .
O2 O 0.25661(9) 0.92947(11) 0.09351(4) 0.0302(2) Uani 1 1 d . . .
H1O2 H 0.1887 0.9590 0.1045 0.045 Uiso 1 1 calc R . .
O3 O 0.73140(9) 0.55520(12) 0.23335(5) 0.0331(3) Uani 1 1 d . . .
O4 O 0.66192(9) 0.54565(12) 0.13293(5) 0.0316(2) Uani 1 1 d . . .
O5 O 0.30429(10) 0.40027(12) 0.31600(5) 0.0389(3) Uani 1 1 d . . .
O6 O 0.27121(10) 0.62035(14) 0.36771(5) 0.0388(3) Uani 1 1 d . . .
O7 O 0.06818(9) 0.90993(12) 0.16409(5) 0.0322(2) Uani 1 1 d . . .
O8 O 0.08032(8) 0.73433(12) 0.24223(5) 0.0311(2) Uani 1 1 d . . .
O9 O 0.37722(10) 0.59923(13) 0.02310(5) 0.0373(3) Uani 1 1 d . . .
O10 O 0.50682(9) 0.80023(12) 0.02604(4) 0.0325(2) Uani 1 1 d . . .
C1 C 0.41694(11) 0.59322(15) 0.16195(6) 0.0212(3) Uani 1 1 d . . .
H1 H 0.4100 0.4953 0.1367 0.025 Uiso 1 1 calc R . .
C2 C 0.52336(12) 0.58550(15) 0.20774(6) 0.0231(3) Uani 1 1 d . . .
C3 C 0.49290(12) 0.61518(15) 0.26583(6) 0.0235(3) Uani 1 1 d . . .
C4 C 0.36037(12) 0.64486(15) 0.27144(6) 0.0229(3) Uani 1 1 d . . .
H4 H 0.3466 0.7568 0.2822 0.027 Uiso 1 1 calc R . .
C5 C 0.30718(11) 0.61023(15) 0.20438(6) 0.0213(3) Uani 1 1 d . . .
H5 H 0.2583 0.5121 0.2037 0.026 Uiso 1 1 calc R . .
C6 C 0.23582(12) 0.74158(15) 0.17448(6) 0.0225(3) Uani 1 1 d . . .
C7 C 0.29440(12) 0.80859(15) 0.12860(6) 0.0227(3) Uani 1 1 d . . .
C8 C 0.41622(12) 0.73915(15) 0.11909(6) 0.0223(3) Uani 1 1 d . . .
H8 H 0.4809 0.8134 0.1342 0.027 Uiso 1 1 calc R . .
C9 C 0.64828(12) 0.56185(15) 0.19342(6) 0.0255(3) Uani 1 1 d . . .
C10 C 0.78441(15) 0.5273(2) 0.11390(9) 0.0466(4) Uani 1 1 d . . .
H10A H 0.8312 0.6211 0.1251 0.070 Uiso 1 1 calc R . .
H10B H 0.7833 0.5117 0.0688 0.070 Uiso 1 1 calc R . .
H10C H 0.8216 0.4365 0.1350 0.070 Uiso 1 1 calc R . .
C11 C 0.30887(12) 0.53960(16) 0.32005(6) 0.0262(3) Uani 1 1 d . . .
C12 C 0.22391(19) 0.5274(3) 0.41735(8) 0.0556(5) Uani 1 1 d . . .
H12A H 0.1500 0.4743 0.4019 0.083 Uiso 1 1 calc R . .
H12B H 0.2057 0.5955 0.4522 0.083 Uiso 1 1 calc R . .
H12C H 0.2841 0.4496 0.4314 0.083 Uiso 1 1 calc R . .
C13 C 0.12111(12) 0.80389(16) 0.19237(6) 0.0251(3) Uani 1 1 d . . .
C14 C -0.03116(14) 0.7957(2) 0.26479(8) 0.0425(4) Uani 1 1 d . . .
H14A H -0.0194 0.9050 0.2771 0.064 Uiso 1 1 calc R . .
H14B H -0.0541 0.7346 0.3008 0.064 Uiso 1 1 calc R . .
H14C H -0.0953 0.7889 0.2318 0.064 Uiso 1 1 calc R . .
C15 C 0.43047(12) 0.70188(16) 0.05090(6) 0.0248(3) Uani 1 1 d . . .
C16 C 0.52742(16) 0.7771(2) -0.03927(7) 0.0415(4) Uani 1 1 d . . .
H16A H 0.5791 0.6856 -0.0440 0.062 Uiso 1 1 calc R . .
H16B H 0.5671 0.8695 -0.0555 0.062 Uiso 1 1 calc R . .
H16C H 0.4499 0.7606 -0.0624 0.062 Uiso 1 1 calc R . .
C1X C 0.08286(14) 0.5010(2) 0.04952(7) 0.0383(4) Uani 1 1 d . . .
H1X H 0.1405 0.5032 0.0838 0.046 Uiso 1 1 calc R . .
C2X C 0.04701(14) 0.35945(18) 0.02405(7) 0.0343(3) Uani 1 1 d . . .
C3X C 0.0990(2) 0.2083(2) 0.04924(10) 0.0631(6) Uani 1 1 d . . .
H3X1 H 0.0617 0.1821 0.0881 0.095 Uiso 1 1 calc R . .
H3X2 H 0.1864 0.2197 0.0572 0.095 Uiso 1 1 calc R . .
H3X3 H 0.0828 0.1249 0.0188 0.095 Uiso 1 1 calc R . .
C4X C -0.03636(15) 0.36105(18) -0.02596(8) 0.0395(4) Uani 1 1 d . . .
H4X H -0.0621 0.2651 -0.0444 0.047 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0305(5) 0.0435(6) 0.0258(5) 0.0044(4) -0.0068(4) -0.0024(4)
O2 0.0312(5) 0.0267(5) 0.0323(5) 0.0087(4) -0.0017(4) 0.0058(4)
O3 0.0234(5) 0.0353(6) 0.0398(6) 0.0104(5) -0.0044(4) 0.0009(4)
O4 0.0246(5) 0.0375(6) 0.0333(5) -0.0010(4) 0.0059(4) 0.0030(4)
O5 0.0463(7) 0.0282(6) 0.0432(6) 0.0104(5) 0.0111(5) 0.0006(5)
O6 0.0429(6) 0.0479(7) 0.0264(5) -0.0002(5) 0.0106(4) 0.0020(5)
O7 0.0271(5) 0.0329(5) 0.0360(6) 0.0020(4) -0.0032(4) 0.0090(4)
O8 0.0231(5) 0.0350(5) 0.0355(5) 0.0039(4) 0.0062(4) 0.0034(4)
O9 0.0379(6) 0.0456(6) 0.0283(5) -0.0080(5) 0.0004(4) -0.0103(5)
O10 0.0419(6) 0.0321(5) 0.0239(5) 0.0034(4) 0.0069(4) -0.0045(4)
C1 0.0225(6) 0.0189(6) 0.0220(6) -0.0008(5) 0.0003(5) 0.0004(5)
C2 0.0227(7) 0.0196(6) 0.0267(7) 0.0046(5) -0.0009(5) -0.0002(5)
C3 0.0250(7) 0.0199(6) 0.0250(7) 0.0047(5) -0.0035(5) -0.0026(5)
C4 0.0258(7) 0.0197(6) 0.0230(6) 0.0008(5) 0.0002(5) 0.0012(5)
C5 0.0210(6) 0.0193(6) 0.0234(6) 0.0008(5) 0.0002(5) 0.0002(5)
C6 0.0220(6) 0.0217(6) 0.0234(6) -0.0008(5) -0.0027(5) 0.0005(5)
C7 0.0252(7) 0.0192(6) 0.0231(6) -0.0007(5) -0.0046(5) 0.0006(5)
C8 0.0223(6) 0.0220(6) 0.0224(6) 0.0009(5) -0.0013(5) -0.0006(5)
C9 0.0255(7) 0.0191(6) 0.0318(7) 0.0052(5) 0.0005(6) 0.0003(5)
C10 0.0292(8) 0.0626(11) 0.0494(10) -0.0042(9) 0.0144(7) 0.0012(8)
C11 0.0226(7) 0.0305(8) 0.0255(7) 0.0037(6) 0.0008(5) 0.0039(5)
C12 0.0539(11) 0.0830(15) 0.0316(9) 0.0108(9) 0.0175(8) -0.0025(10)
C13 0.0223(7) 0.0249(7) 0.0274(7) -0.0025(5) -0.0037(5) -0.0002(5)
C14 0.0280(8) 0.0503(10) 0.0503(10) 0.0021(8) 0.0136(7) 0.0057(7)
C15 0.0224(7) 0.0281(7) 0.0237(7) 0.0028(5) -0.0014(5) 0.0030(5)
C16 0.0561(10) 0.0438(9) 0.0257(8) 0.0036(7) 0.0124(7) -0.0008(8)
C1X 0.0322(8) 0.0477(9) 0.0342(8) 0.0024(7) -0.0068(6) -0.0022(7)
C2X 0.0330(8) 0.0326(8) 0.0383(8) 0.0066(6) 0.0097(6) 0.0075(6)
C3X 0.0737(14) 0.0473(11) 0.0693(13) 0.0193(10) 0.0130(11) 0.0249(10)
C4X 0.0473(9) 0.0287(8) 0.0425(9) -0.0062(7) 0.0014(7) -0.0074(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
O1 C3 1.3385(16) . ?
O1 H1O1 0.8400 . ?
O2 C7 1.3361(16) . ?
O2 H1O2 0.8400 . ?
O3 C9 1.2273(17) . ?
O4 C9 1.3268(17) . ?
O4 C10 1.4483(18) . ?
O5 C11 1.1980(18) . ?
O6 C11 1.3240(17) . ?
O6 C12 1.454(2) . ?
O7 C13 1.2257(17) . ?
O8 C13 1.3285(17) . ?
O8 C14 1.4510(18) . ?
O9 C15 1.2011(17) . ?
O10 C15 1.3277(17) . ?
O10 C16 1.4504(17) . ?
C1 C2 1.4978(17) . ?
C1 C8 1.5539(17) . ?
C1 C5 1.5677(17) . ?
C1 H1 1.0000 . ?
C2 C3 1.3375(19) . ?
C2 C9 1.4495(19) . ?
C3 C4 1.5027(18) . ?
C4 C11 1.5165(18) . ?
C4 C5 1.5586(17) . ?
C4 H4 1.0000 . ?
C5 C6 1.5007(17) . ?
C5 H5 1.0000 . ?
C6 C7 1.3406(19) . ?
C6 C13 1.4507(19) . ?
C7 C8 1.5002(18) . ?
C8 C15 1.5192(18) . ?
C8 H8 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C1X C4X 1.375(2) 3_565 ?
C1X C2X 1.381(2) . ?
C1X H1X 0.9500 . ?
C2X C4X 1.381(2) . ?
C2X C3X 1.506(2) . ?
C3X H3X1 0.9800 . ?
C3X H3X2 0.9800 . ?
C3X H3X3 0.9800 . ?
C4X C1X 1.375(2) 3_565 ?
C4X H4X 0.9500 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1O1 109.5 . . ?
C7 O2 H1O2 109.5 . . ?
C9 O4 C10 116.59(12) . . ?
C11 O6 C12 115.16(13) . . ?
C13 O8 C14 116.20(12) . . ?
C15 O10 C16 116.20(12) . . ?
C2 C1 C8 113.90(10) . . ?
C2 C1 C5 103.25(10) . . ?
C8 C1 C5 106.99(10) . . ?
C2 C1 H1 110.8 . . ?
C8 C1 H1 110.8 . . ?
C5 C1 H1 110.8 . . ?
C3 C2 C9 121.21(12) . . ?
C3 C2 C1 112.18(12) . . ?
C9 C2 C1 126.44(12) . . ?
C2 C3 O1 127.40(13) . . ?
C2 C3 C4 113.89(11) . . ?
O1 C3 C4 118.69(11) . . ?
C3 C4 C11 111.18(10) . . ?
C3 C4 C5 102.47(10) . . ?
C11 C4 C5 112.86(11) . . ?
C3 C4 H4 110.0 . . ?
C11 C4 H4 110.0 . . ?
C5 C4 H4 110.0 . . ?
C6 C5 C4 114.77(10) . . ?
C6 C5 C1 103.16(10) . . ?
C4 C5 C1 106.91(10) . . ?
C6 C5 H5 110.6 . . ?
C4 C5 H5 110.6 . . ?
C1 C5 H5 110.6 . . ?
C7 C6 C13 120.32(12) . . ?
C7 C6 C5 111.85(12) . . ?
C13 C6 C5 127.71(12) . . ?
O2 C7 C6 126.81(12) . . ?
O2 C7 C8 119.17(11) . . ?
C6 C7 C8 113.98(11) . . ?
C7 C8 C15 110.91(10) . . ?
C7 C8 C1 102.35(10) . . ?
C15 C8 C1 114.04(11) . . ?
C7 C8 H8 109.8 . . ?
C15 C8 H8 109.8 . . ?
C1 C8 H8 109.8 . . ?
O3 C9 O4 124.18(13) . . ?
O3 C9 C2 123.20(13) . . ?
O4 C9 C2 112.62(11) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 O6 124.29(13) . . ?
O5 C11 C4 123.96(13) . . ?
O6 C11 C4 111.75(12) . . ?
O6 C12 H12A 109.5 . . ?
O6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O7 C13 O8 124.00(13) . . ?
O7 C13 C6 122.97(13) . . ?
O8 C13 C6 113.03(11) . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 O10 124.82(13) . . ?
O9 C15 C8 124.16(12) . . ?
O10 C15 C8 111.00(11) . . ?
O10 C16 H16A 109.5 . . ?
O10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4X C1X C2X 120.95(14) 3_565 . ?
C4X C1X H1X 119.5 3_565 . ?
C2X C1X H1X 119.5 . . ?
C4X C2X C1X 117.85(14) . . ?
C4X C2X C3X 121.10(16) . . ?
C1X C2X C3X 121.04(16) . . ?
C2X C3X H3X1 109.5 . . ?
C2X C3X H3X2 109.5 . . ?
H3X1 C3X H3X2 109.5 . . ?
C2X C3X H3X3 109.5 . . ?
H3X1 C3X H3X3 109.5 . . ?
H3X2 C3X H3X3 109.5 . . ?
C1X C4X C2X 121.20(14) 3_565 . ?
C1X C4X H4X 119.4 3_565 . ?
C2X C4X H4X 119.4 . . ?
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 C1 C2 C3 107.60(13) . . . . ?
C5 C1 C2 C3 -8.03(14) . . . . ?
C8 C1 C2 C9 -67.60(16) . . . . ?
C5 C1 C2 C9 176.76(12) . . . . ?
C9 C2 C3 O1 -1.3(2) . . . . ?
C1 C2 C3 O1 -176.78(12) . . . . ?
C9 C2 C3 C4 176.92(11) . . . . ?
C1 C2 C3 C4 1.43(16) . . . . ?
C2 C3 C4 C11 126.71(12) . . . . ?
O1 C3 C4 C11 -54.92(15) . . . . ?
C2 C3 C4 C5 5.88(14) . . . . ?
O1 C3 C4 C5 -175.74(11) . . . . ?
C3 C4 C5 C6 -124.11(11) . . . . ?
C11 C4 C5 C6 116.24(12) . . . . ?
C3 C4 C5 C1 -10.38(12) . . . . ?
C11 C4 C5 C1 -130.04(11) . . . . ?
C2 C1 C5 C6 132.61(10) . . . . ?
C8 C1 C5 C6 12.14(13) . . . . ?
C2 C1 C5 C4 11.22(12) . . . . ?
C8 C1 C5 C4 -109.25(11) . . . . ?
C4 C5 C6 C7 108.77(13) . . . . ?
C1 C5 C6 C7 -7.13(14) . . . . ?
C4 C5 C6 C13 -67.14(17) . . . . ?
C1 C5 C6 C13 176.96(12) . . . . ?
C13 C6 C7 O2 -2.7(2) . . . . ?
C5 C6 C7 O2 -178.97(12) . . . . ?
C13 C6 C7 C8 175.23(11) . . . . ?
C5 C6 C7 C8 -1.03(16) . . . . ?
O2 C7 C8 C15 -51.14(15) . . . . ?
C6 C7 C8 C15 130.75(12) . . . . ?
O2 C7 C8 C1 -173.15(11) . . . . ?
C6 C7 C8 C1 8.73(14) . . . . ?
C2 C1 C8 C7 -125.93(11) . . . . ?
C5 C1 C8 C7 -12.51(12) . . . . ?
C2 C1 C8 C15 114.22(12) . . . . ?
C5 C1 C8 C15 -132.36(11) . . . . ?
C10 O4 C9 O3 -3.4(2) . . . . ?
C10 O4 C9 C2 177.76(13) . . . . ?
C3 C2 C9 O3 5.9(2) . . . . ?
C1 C2 C9 O3 -179.28(12) . . . . ?
C3 C2 C9 O4 -175.20(12) . . . . ?
C1 C2 C9 O4 -0.39(19) . . . . ?
C12 O6 C11 O5 1.0(2) . . . . ?
C12 O6 C11 C4 -178.18(13) . . . . ?
C3 C4 C11 O5 -64.04(17) . . . . ?
C5 C4 C11 O5 50.46(18) . . . . ?
C3 C4 C11 O6 115.13(12) . . . . ?
C5 C4 C11 O6 -130.37(12) . . . . ?
C14 O8 C13 O7 -2.9(2) . . . . ?
C14 O8 C13 C6 177.03(12) . . . . ?
C7 C6 C13 O7 6.0(2) . . . . ?
C5 C6 C13 O7 -178.39(12) . . . . ?
C7 C6 C13 O8 -173.92(12) . . . . ?
C5 C6 C13 O8 1.69(19) . . . . ?
C16 O10 C15 O9 -1.3(2) . . . . ?
C16 O10 C15 C8 -179.62(12) . . . . ?
C7 C8 C15 O9 -70.04(17) . . . . ?
C1 C8 C15 O9 44.87(18) . . . . ?
C7 C8 C15 O10 108.30(12) . . . . ?
C1 C8 C15 O10 -136.79(11) . . . . ?
C4X C1X C2X C4X 0.3(3) 3_565 . . . ?
C4X C1X C2X C3X 179.19(17) 3_565 . . . ?
C1X C2X C4X C1X -0.3(3) . . . 3_565 ?
C3X C2X C4X C1X -179.19(17) . . . 3_565 ?
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
O2 H1O2 O7 0.84 1.95 2.6547(14) 141.0 .
O1 H1O1 O3 0.84 2.00 2.7004(15) 139.9 .
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.299
_refine_diff_density_min -0.218
_refine_diff_density_rms 0.047
# Attachment 'FormII_Deposition.cif'
data_jiabin135
_database_code_depnum_ccdc_archive 'CCDC 829076'
#TrackingRef 'FormII_Deposition.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C16 H18 O10'
_chemical_formula_weight 370.30
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M 'P -1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.2550(2)
_cell_length_b 9.2807(3)
_cell_length_c 13.0344(4)
_cell_angle_alpha 77.3590(10)
_cell_angle_beta 78.8160(10)
_cell_angle_gamma 88.8110(10)
_cell_volume 839.87(4)
_cell_formula_units_Z 2
_cell_measurement_temperature 150(2)
_cell_measurement_reflns_used 9807
_cell_measurement_theta_min 2.249
_cell_measurement_theta_max 30.479
_exptl_crystal_description Blocks
_exptl_crystal_colour Colourless
_exptl_crystal_size_max 0.23
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.19
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.464
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 388
_exptl_absorpt_coefficient_mu 0.124
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.9725
_exptl_absorpt_correction_T_max 0.9772
_exptl_absorpt_process_details 'SADABS (Bruker, 2001)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker Kappa APEXII CCD Diffractometer'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 11935
_diffrn_reflns_av_R_equivalents 0.0414
_diffrn_reflns_av_sigmaI/netI 0.0295
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.47
_diffrn_reflns_theta_max 25.00
_reflns_number_total 2945
_reflns_number_gt 2743
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2007)'
_computing_cell_refinement 'SAINT (Bruker, 2007)'
_computing_data_reduction 'SAINT '
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL-Plus (Sheldrick, 2008)'
_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^)+(0.0399P)^2^+0.3630P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2945
_refine_ls_number_parameters 247
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0355
_refine_ls_R_factor_gt 0.0329
_refine_ls_wR_factor_ref 0.0888
_refine_ls_wR_factor_gt 0.0859
_refine_ls_goodness_of_fit_ref 1.046
_refine_ls_restrained_S_all 1.046
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19542(14) 0.42586(11) 0.72199(8) 0.0257(2) Uani 1 1 d . . .
H1O1 H 0.234(3) 0.487(2) 0.7572(17) 0.055(6) Uiso 1 1 d . . .
O2 O 0.43456(15) -0.21651(11) 0.89024(8) 0.0278(2) Uani 1 1 d . . .
H1O2 H 0.374(3) -0.278(2) 0.8610(17) 0.061(6) Uiso 1 1 d . . .
O3 O 0.42223(15) 0.48733(10) 0.85484(8) 0.0288(2) Uani 1 1 d . . .
O4 O 0.69498(14) 0.36492(10) 0.84831(7) 0.0244(2) Uani 1 1 d . . .
O5 O 0.48888(15) 0.33181(12) 0.47458(8) 0.0348(3) Uani 1 1 d . . .
O6 O 0.17730(13) 0.35977(10) 0.50323(7) 0.0255(2) Uani 1 1 d . . .
O7 O 0.22031(14) -0.26971(10) 0.74829(8) 0.0272(2) Uani 1 1 d . . .
O8 O 0.22830(14) -0.08923(10) 0.59953(8) 0.0242(2) Uani 1 1 d . . .
O9 O 0.90358(15) -0.01821(12) 0.77522(8) 0.0356(3) Uani 1 1 d . . .
O10 O 0.77564(14) -0.09256(11) 0.94963(8) 0.0298(3) Uani 1 1 d . . .
C1 C 0.57564(18) 0.15908(13) 0.73902(10) 0.0180(3) Uani 1 1 d . . .
H3 H 0.7064 0.1898 0.7001 0.022 Uiso 1 1 calc R . .
C2 C 0.46688(19) 0.28925(13) 0.76718(10) 0.0193(3) Uani 1 1 d . . .
C3 C 0.31820(19) 0.31714(14) 0.71854(10) 0.0196(3) Uani 1 1 d . . .
C4 C 0.30196(18) 0.21455(14) 0.64566(10) 0.0188(3) Uani 1 1 d . . .
H4 H 0.1760 0.1635 0.6651 0.023 Uiso 1 1 calc R . .
C5 C 0.46065(18) 0.10325(13) 0.66436(10) 0.0182(3) Uani 1 1 d . . .
H5 H 0.5439 0.0978 0.5946 0.022 Uiso 1 1 calc R . .
C6 C 0.39353(19) -0.04877(14) 0.72665(10) 0.0203(3) Uani 1 1 d . . .
C7 C 0.45907(18) -0.08780(14) 0.81800(10) 0.0204(3) Uani 1 1 d . . .
C8 C 0.57765(18) 0.03092(14) 0.83770(10) 0.0189(3) Uani 1 1 d . . .
H8 H 0.5167 0.0624 0.9047 0.023 Uiso 1 1 calc R . .
C9 C 0.5210(2) 0.38843(14) 0.82853(10) 0.0210(3) Uani 1 1 d . . .
C10 C 0.7677(2) 0.47260(16) 0.89628(12) 0.0300(3) Uani 1 1 d . . .
H10A H 0.7703 0.5707 0.8489 0.045 Uiso 1 1 calc R . .
H10B H 0.8954 0.4465 0.9068 0.045 Uiso 1 1 calc R . .
H10C H 0.6867 0.4735 0.9657 0.045 Uiso 1 1 calc R . .
C11 C 0.33672(19) 0.30623(14) 0.53132(10) 0.0204(3) Uani 1 1 d . . .
C12 C 0.2022(2) 0.46142(17) 0.39960(12) 0.0318(3) Uani 1 1 d . . .
H12C H 0.2777 0.5473 0.4004 0.048 Uiso 1 1 calc R . .
H12B H 0.0790 0.4939 0.3843 0.048 Uiso 1 1 calc R . .
H12A H 0.2665 0.4117 0.3441 0.048 Uiso 1 1 calc R . .
C13 C 0.27381(19) -0.14764(14) 0.69444(11) 0.0215(3) Uani 1 1 d . . .
C14 C 0.1020(2) -0.17863(17) 0.56451(13) 0.0309(3) Uani 1 1 d . . .
H14A H 0.1544 -0.2769 0.5649 0.046 Uiso 1 1 calc R . .
H14B H 0.0867 -0.1315 0.4918 0.046 Uiso 1 1 calc R . .
H14C H -0.0205 -0.1880 0.6132 0.046 Uiso 1 1 calc R . .
C15 C 0.77167(19) -0.02662(14) 0.84798(11) 0.0216(3) Uani 1 1 d . . .
C16 C 0.9466(2) -0.16868(19) 0.96782(14) 0.0397(4) Uani 1 1 d . . .
H16C H 0.9670 -0.2468 0.9272 0.060 Uiso 1 1 calc R . .
H16B H 0.9352 -0.2124 1.0444 0.060 Uiso 1 1 calc R . .
H16A H 1.0532 -0.0983 0.9441 0.060 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0268(5) 0.0219(5) 0.0312(5) -0.0092(4) -0.0096(4) 0.0101(4)
O2 0.0338(6) 0.0178(5) 0.0293(5) 0.0037(4) -0.0102(5) -0.0015(4)
O3 0.0391(6) 0.0222(5) 0.0290(5) -0.0100(4) -0.0124(5) 0.0115(4)
O4 0.0274(5) 0.0228(5) 0.0258(5) -0.0080(4) -0.0094(4) 0.0030(4)
O5 0.0262(6) 0.0385(6) 0.0293(6) 0.0077(5) 0.0021(5) 0.0059(5)
O6 0.0229(5) 0.0264(5) 0.0242(5) 0.0047(4) -0.0092(4) -0.0011(4)
O7 0.0274(5) 0.0156(5) 0.0374(6) -0.0031(4) -0.0065(4) 0.0003(4)
O8 0.0261(5) 0.0214(5) 0.0279(5) -0.0073(4) -0.0098(4) 0.0003(4)
O9 0.0248(6) 0.0416(6) 0.0331(6) 0.0005(5) 0.0008(5) 0.0111(5)
O10 0.0269(6) 0.0376(6) 0.0255(5) -0.0045(4) -0.0108(4) 0.0128(4)
C1 0.0179(6) 0.0165(6) 0.0185(6) -0.0025(5) -0.0028(5) 0.0020(5)
C2 0.0220(7) 0.0159(6) 0.0183(6) -0.0014(5) -0.0024(5) 0.0020(5)
C3 0.0215(7) 0.0161(6) 0.0184(6) -0.0011(5) -0.0005(5) 0.0023(5)
C4 0.0187(6) 0.0168(6) 0.0196(6) -0.0017(5) -0.0035(5) 0.0008(5)
C5 0.0189(6) 0.0164(6) 0.0185(6) -0.0033(5) -0.0029(5) 0.0019(5)
C6 0.0204(7) 0.0163(6) 0.0236(7) -0.0042(5) -0.0036(5) 0.0034(5)
C7 0.0190(7) 0.0161(6) 0.0233(7) -0.0013(5) -0.0016(5) 0.0038(5)
C8 0.0197(7) 0.0177(6) 0.0183(6) -0.0032(5) -0.0028(5) 0.0041(5)
C9 0.0277(7) 0.0171(6) 0.0170(6) -0.0005(5) -0.0052(5) 0.0034(5)
C10 0.0370(9) 0.0291(8) 0.0286(7) -0.0101(6) -0.0132(6) -0.0007(6)
C11 0.0232(7) 0.0168(6) 0.0216(7) -0.0037(5) -0.0055(6) 0.0009(5)
C12 0.0343(8) 0.0304(8) 0.0266(7) 0.0079(6) -0.0120(6) -0.0014(6)
C13 0.0193(7) 0.0174(6) 0.0279(7) -0.0061(5) -0.0042(5) 0.0056(5)
C14 0.0275(8) 0.0317(8) 0.0399(8) -0.0160(7) -0.0127(7) 0.0006(6)
C15 0.0231(7) 0.0179(6) 0.0248(7) -0.0051(5) -0.0068(6) 0.0033(5)
C16 0.0364(9) 0.0476(10) 0.0398(9) -0.0097(8) -0.0207(8) 0.0217(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
O1 C3 1.3344(16) . ?
O1 H1O1 0.88(2) . ?
O2 C7 1.3404(16) . ?
O2 H1O2 0.92(2) . ?
O3 C9 1.2202(16) . ?
O4 C9 1.3407(17) . ?
O4 C10 1.4462(16) . ?
O5 C11 1.1997(17) . ?
O6 C11 1.3339(16) . ?
O6 C12 1.4498(16) . ?
O7 C13 1.2212(16) . ?
O8 C13 1.3383(17) . ?
O8 C14 1.4476(16) . ?
O9 C15 1.2000(17) . ?
O10 C15 1.3379(16) . ?
O10 C16 1.4484(18) . ?
C1 C2 1.5030(17) . ?
C1 C8 1.5512(17) . ?
C1 C5 1.5701(18) . ?
C1 H3 1.0000 . ?
C2 C3 1.3470(19) . ?
C2 C9 1.4491(19) . ?
C3 C4 1.5056(18) . ?
C4 C11 1.5221(17) . ?
C4 C5 1.5495(17) . ?
C4 H4 1.0000 . ?
C5 C6 1.5035(17) . ?
C5 H5 1.0000 . ?
C6 C7 1.3412(19) . ?
C6 C13 1.4546(19) . ?
C7 C8 1.5063(18) . ?
C8 C15 1.5150(18) . ?
C8 H8 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12A 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16A 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
C3 O1 H1O1 108.1(14) . . ?
C7 O2 H1O2 105.7(14) . . ?
C9 O4 C10 115.64(11) . . ?
C11 O6 C12 114.49(11) . . ?
C13 O8 C14 115.45(11) . . ?
C15 O10 C16 116.00(11) . . ?
C2 C1 C8 112.91(10) . . ?
C2 C1 C5 103.39(10) . . ?
C8 C1 C5 107.46(10) . . ?
C2 C1 H3 110.9 . . ?
C8 C1 H3 110.9 . . ?
C5 C1 H3 110.9 . . ?
C3 C2 C9 121.12(12) . . ?
C3 C2 C1 112.46(11) . . ?
C9 C2 C1 126.04(12) . . ?
O1 C3 C2 128.91(12) . . ?
O1 C3 C4 117.88(12) . . ?
C2 C3 C4 113.08(11) . . ?
C3 C4 C11 107.53(10) . . ?
C3 C4 C5 103.44(10) . . ?
C11 C4 C5 111.79(10) . . ?
C3 C4 H4 111.3 . . ?
C11 C4 H4 111.3 . . ?
C5 C4 H4 111.3 . . ?
C6 C5 C4 114.63(11) . . ?
C6 C5 C1 103.37(10) . . ?
C4 C5 C1 107.25(10) . . ?
C6 C5 H5 110.4 . . ?
C4 C5 H5 110.4 . . ?
C1 C5 H5 110.4 . . ?
C7 C6 C13 121.80(12) . . ?
C7 C6 C5 112.34(11) . . ?
C13 C6 C5 125.85(12) . . ?
O2 C7 C6 128.49(13) . . ?
O2 C7 C8 117.89(12) . . ?
C6 C7 C8 113.61(11) . . ?
C7 C8 C15 109.84(10) . . ?
C7 C8 C1 103.11(10) . . ?
C15 C8 C1 114.10(10) . . ?
C7 C8 H8 109.9 . . ?
C15 C8 H8 109.9 . . ?
C1 C8 H8 109.9 . . ?
O3 C9 O4 123.61(12) . . ?
O3 C9 C2 123.51(13) . . ?
O4 C9 C2 112.79(11) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 O6 123.97(12) . . ?
O5 C11 C4 124.44(12) . . ?
O6 C11 C4 111.53(11) . . ?
O6 C12 H12C 109.5 . . ?
O6 C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
O6 C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
O7 C13 O8 123.95(12) . . ?
O7 C13 C6 123.73(13) . . ?
O8 C13 C6 112.32(11) . . ?
O8 C14 H14A 109.5 . . ?
O8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 O10 124.04(13) . . ?
O9 C15 C8 125.24(12) . . ?
O10 C15 C8 110.70(11) . . ?
O10 C16 H16C 109.5 . . ?
O10 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
O10 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16B C16 H16A 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 C1 C2 C3 -117.98(12) . . . . ?
C5 C1 C2 C3 -2.17(14) . . . . ?
C8 C1 C2 C9 69.14(16) . . . . ?
C5 C1 C2 C9 -175.04(12) . . . . ?
C9 C2 C3 O1 -4.2(2) . . . . ?
C1 C2 C3 O1 -177.51(12) . . . . ?
C9 C2 C3 C4 171.38(11) . . . . ?
C1 C2 C3 C4 -1.89(16) . . . . ?
O1 C3 C4 C11 62.84(15) . . . . ?
C2 C3 C4 C11 -113.31(12) . . . . ?
O1 C3 C4 C5 -178.76(10) . . . . ?
C2 C3 C4 C5 5.10(14) . . . . ?
C3 C4 C5 C6 108.00(12) . . . . ?
C11 C4 C5 C6 -136.59(11) . . . . ?
C3 C4 C5 C1 -6.12(12) . . . . ?
C11 C4 C5 C1 109.29(11) . . . . ?
C2 C1 C5 C6 -116.31(11) . . . . ?
C8 C1 C5 C6 3.32(12) . . . . ?
C2 C1 C5 C4 5.17(12) . . . . ?
C8 C1 C5 C4 124.81(10) . . . . ?
C4 C5 C6 C7 -119.62(12) . . . . ?
C1 C5 C6 C7 -3.25(14) . . . . ?
C4 C5 C6 C13 61.33(16) . . . . ?
C1 C5 C6 C13 177.70(12) . . . . ?
C13 C6 C7 O2 2.2(2) . . . . ?
C5 C6 C7 O2 -176.93(12) . . . . ?
C13 C6 C7 C8 -179.00(11) . . . . ?
C5 C6 C7 C8 1.91(16) . . . . ?
O2 C7 C8 C15 57.36(15) . . . . ?
C6 C7 C8 C15 -121.61(12) . . . . ?
O2 C7 C8 C1 179.34(11) . . . . ?
C6 C7 C8 C1 0.37(15) . . . . ?
C2 C1 C8 C7 111.02(12) . . . . ?
C5 C1 C8 C7 -2.34(13) . . . . ?
C2 C1 C8 C15 -129.91(12) . . . . ?
C5 C1 C8 C15 116.73(11) . . . . ?
C10 O4 C9 O3 -4.79(18) . . . . ?
C10 O4 C9 C2 171.88(11) . . . . ?
C3 C2 C9 O3 12.3(2) . . . . ?
C1 C2 C9 O3 -175.39(12) . . . . ?
C3 C2 C9 O4 -164.36(12) . . . . ?
C1 C2 C9 O4 7.94(18) . . . . ?
C12 O6 C11 O5 -3.97(19) . . . . ?
C12 O6 C11 C4 173.56(11) . . . . ?
C3 C4 C11 O5 87.36(16) . . . . ?
C5 C4 C11 O5 -25.52(18) . . . . ?
C3 C4 C11 O6 -90.16(13) . . . . ?
C5 C4 C11 O6 156.96(10) . . . . ?
C14 O8 C13 O7 2.42(19) . . . . ?
C14 O8 C13 C6 -177.23(11) . . . . ?
C7 C6 C13 O7 2.1(2) . . . . ?
C5 C6 C13 O7 -178.93(12) . . . . ?
C7 C6 C13 O8 -178.25(12) . . . . ?
C5 C6 C13 O8 0.72(18) . . . . ?
C16 O10 C15 O9 -5.8(2) . . . . ?
C16 O10 C15 C8 172.46(12) . . . . ?
C7 C8 C15 O9 90.01(16) . . . . ?
C1 C8 C15 O9 -25.17(19) . . . . ?
C7 C8 C15 O10 -88.26(13) . . . . ?
C1 C8 C15 O10 156.56(11) . . . . ?
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
O1 H1O1 O3 0.88(2) 2.04(2) 2.7583(14) 137.9(19) .
O1 H1O1 O7 0.88(2) 2.24(2) 2.9329(13) 135.4(18) 1_565
O2 H1O2 O7 0.92(2) 2.00(2) 2.7624(15) 140.0(19) .
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.234
_refine_diff_density_min -0.225
_refine_diff_density_rms 0.045