# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2009
data_global
_journal_coden_Cambridge 182
_journal_volume ?
_journal_page_first ?
_journal_year ?
loop_
_publ_author_name
'G. Mehta'
'Saikat Sen'
_publ_contact_author_name 'G. Mehta'
_publ_contact_author_email GM@ORGCHEM.IISC.ERNET.IN
_publ_section_title
;
Towards a temperature guided molecular switch:
An unusual reversible low temperature polymorphic phase transition
in a conformationally locked environment
;
# Attachment 'CIF.cif'
data_tetraacetate_alpha_form_RT
_database_code_depnum_ccdc_archive 'CCDC 724609'
#===============================================================================
_audit_creation_date 'Mar 02 19:52:37 2009'
_audit_creation_method 'PLATON
option'
# 5. CHEMICAL DATA
_chemical_name_systematic
;
(all trans)-3,6,7-tri(acetyloxy)-4a,8a-dihydroxyperhydro-2-naphthalenyl acetate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C18 H26 O10'
_chemical_formula_structural 'C18 H26 O10'
_chemical_formula_sum 'C18 H26 O10'
_chemical_formula_iupac 'C18 H26 O10'
_chemical_formula_weight 402.39
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_Int_Tables_number 15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
_cell_length_a 21.433(7)
_cell_length_b 5.7126(18)
_cell_length_c 16.720(5)
_cell_angle_alpha 90
_cell_angle_beta 105.664(5)
_cell_angle_gamma 90
_cell_volume 1971.1(11)
_cell_formula_units_Z 4
_cell_measurement_temperature 291(2)
_cell_measurement_reflns_used 698
_cell_measurement_theta_min 2.76
_cell_measurement_theta_max 23.43
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.24
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.356
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 856
_exptl_absorpt_coefficient_mu 0.111
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min 0.9439
_exptl_absorpt_correction_T_max 0.9738
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 291(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoKa
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
_diffrn_reflns_number 6929
_diffrn_reflns_av_R_equivalents 0.0176
_diffrn_reflns_av_sigmaI/netI 0.0162
_diffrn_reflns_limit_h_min -25
_diffrn_reflns_limit_h_max 25
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_theta_min 2.53
_diffrn_reflns_theta_max 25.35
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_reduction_process
;
;
_reflns_number_total 1800
_reflns_number_gt 1419
_reflns_threshold_expression I>2sigma(I)
_computing_data_collection 'SMART (Bruker, 1998)'
_computing_cell_refinement 'SMART (Bruker, 1998)'
_computing_data_reduction 'SAINT (Bruker, 1998)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_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. The carbonyl oxygen atom
O5 is diordered over two sites A and B, with occupancies 0.52 and 0.48
respectively.
;
_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^)+(0.0753P)^2^+1.3499P] 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 1800
_refine_ls_number_parameters 139
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0642
_refine_ls_R_factor_gt 0.0514
_refine_ls_wR_factor_ref 0.1518
_refine_ls_wR_factor_gt 0.1402
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_restrained_S_all 1.052
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.213
_refine_diff_density_min -0.182
_refine_diff_density_rms 0.041
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.59427(7) 0.2114(3) 0.38645(8) 0.0575(4) Uani 1 1 d . . .
O2 O 0.47146(7) 0.2187(2) 0.41996(8) 0.0524(4) Uani 1 1 d . . .
O3 O 0.34652(7) 0.1654(3) 0.43824(10) 0.0690(5) Uani 1 1 d . A .
O4 O 0.59879(11) 0.0372(3) 0.26928(11) 0.0888(6) Uani 1 1 d . . .
O5A O 0.2592(7) -0.0147(16) 0.3678(12) 0.144(8) Uani 0.52(3) 1 d P A 1
O5B O 0.2473(3) 0.051(2) 0.4283(15) 0.125(6) Uani 0.48(3) 1 d P A 2
C1 C 0.59745(10) -0.0126(4) 0.42889(13) 0.0535(5) Uani 1 1 d . . .
C2 C 0.53162(10) -0.1314(4) 0.41179(12) 0.0508(5) Uani 1 1 d . . .
C3 C 0.48438(9) -0.0135(3) 0.45299(11) 0.0447(5) Uani 1 1 d . . .
C4 C 0.42154(10) -0.1537(4) 0.43847(12) 0.0515(5) Uani 1 1 d . . .
C5 C 0.37290(10) -0.0502(4) 0.48012(13) 0.0554(6) Uani 1 1 d . . .
C6 C 0.59617(10) 0.2130(4) 0.30748(13) 0.0556(6) Uani 1 1 d . . .
C7 C 0.59517(13) 0.4542(4) 0.27488(15) 0.0713(7) Uani 1 1 d . . .
C8 C 0.28552(14) 0.1754(7) 0.3978(2) 0.0992(11) Uani 1 1 d . . .
C9 C 0.26633(14) 0.4011(7) 0.3563(2) 0.1094(12) Uani 1 1 d . A .
H2O H 0.4429 0.2138 0.3760 0.079 Uiso 1 1 calc R . .
H1 H 0.6273 -0.1159 0.4104 0.064 Uiso 1 1 calc R . .
H2A H 0.5380 -0.2922 0.4309 0.061 Uiso 1 1 calc R . .
H2B H 0.5123 -0.1348 0.3522 0.061 Uiso 1 1 calc R . .
H4A H 0.4015 -0.1637 0.3792 0.062 Uiso 1 1 calc R . .
H4B H 0.4320 -0.3117 0.4590 0.062 Uiso 1 1 calc R . .
H5 H 0.3376 -0.1623 0.4761 0.066 Uiso 1 1 calc R . .
H7A H 0.5930 0.5639 0.3175 0.107 Uiso 1 1 calc R . .
H7B H 0.5580 0.4735 0.2281 0.107 Uiso 1 1 calc R . .
H7C H 0.6339 0.4815 0.2578 0.107 Uiso 1 1 calc R . .
H9A H 0.3017 0.4635 0.3378 0.164 Uiso 1 1 calc R . .
H9B H 0.2553 0.5085 0.3945 0.164 Uiso 1 1 calc R . .
H9C H 0.2295 0.3788 0.3093 0.164 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 0.0684(9) 0.0643(10) 0.0449(8) -0.0027(7) 0.0241(7) -0.0019(7)
O2 0.0562(9) 0.0565(9) 0.0398(7) 0.0072(6) 0.0048(6) 0.0042(7)
O3 0.0460(9) 0.0798(11) 0.0741(11) 0.0112(9) 0.0043(7) 0.0069(8)
O4 0.1317(17) 0.0858(13) 0.0556(10) -0.0171(10) 0.0367(11) -0.0085(12)
O5A 0.096(7) 0.115(5) 0.164(11) 0.034(5) -0.065(7) -0.027(4)
O5B 0.050(3) 0.138(6) 0.182(14) 0.051(7) 0.021(4) -0.002(3)
C1 0.0549(12) 0.0599(13) 0.0473(11) -0.0015(10) 0.0167(9) 0.0038(10)
C2 0.0575(12) 0.0553(12) 0.0387(10) -0.0034(9) 0.0114(9) 0.0015(10)
C3 0.0483(10) 0.0478(11) 0.0360(10) 0.0024(8) 0.0078(8) 0.0034(9)
C4 0.0537(12) 0.0591(13) 0.0377(10) -0.0031(9) 0.0052(8) -0.0023(10)
C5 0.0479(11) 0.0648(14) 0.0505(12) 0.0034(10) 0.0083(9) -0.0007(10)
C6 0.0516(12) 0.0745(15) 0.0402(10) -0.0089(11) 0.0117(9) -0.0069(11)
C7 0.0829(17) 0.0786(17) 0.0539(13) 0.0019(12) 0.0211(12) -0.0130(14)
C8 0.0509(15) 0.106(3) 0.121(3) 0.030(2) -0.0106(17) -0.0012(16)
C9 0.0595(16) 0.122(3) 0.134(3) 0.042(2) 0.0035(17) 0.0165(17)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.456(3) . ?
O1 C6 1.332(2) . ?
O2 C3 1.434(2) . ?
O2 H2O 0.8200 . ?
O3 C5 1.454(3) . ?
O3 C8 1.301(3) . ?
O5A C8 1.264(9) . ?
O5B C8 1.286(7) . ?
C1 H1 0.9800 . ?
C2 C1 1.521(3) . ?
C2 C3 1.527(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C3 1.529(3) . ?
C4 C5 1.521(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5 0.9800 . ?
C6 O4 1.200(3) . ?
C6 C7 1.479(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.470(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O1 C1 C2 112.42(17) . . ?
O1 C6 C7 111.75(19) . . ?
O1 C1 H1 108.9 . . ?
O2 C3 C2 108.46(16) . . ?
O2 C3 C4 110.67(15) . . ?
O3 C5 C4 109.53(18) . . ?
O3 C5 H5 109.1 . . ?
O3 C8 C9 113.4(3) . . ?
O4 C6 O1 122.7(2) . . ?
O4 C6 C7 125.6(2) . . ?
O5A C8 O5B 54.6(5) . . ?
O5A C8 O3 116.5(7) . . ?
O5A C8 C9 121.9(4) . . ?
O5B C8 O3 115.3(7) . . ?
O5B C8 C9 122.9(4) . . ?
C1 C2 C3 114.38(18) . . ?
C1 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
C2 C3 C4 111.12(17) . . ?
C2 C1 H1 108.9 . . ?
C3 O2 H2O 109.5 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C4 C5 H5 109.1 . . ?
C5 C4 C3 114.01(17) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C6 O1 C1 118.64(17) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
C8 O3 C5 119.5(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H2A C2 H2B 107.6 . . ?
H4A C4 H4B 107.6 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
C1 O1 C6 O4 1.9(3) . . . . ?
C1 O1 C6 C7 -177.67(19) . . . . ?
C1 C2 C3 O2 62.6(2) . . . . ?
C1 C2 C3 C4 -175.55(16) . . . . ?
C3 C2 C1 O1 -71.0(2) . . . . ?
C3 C4 C5 O3 70.2(2) . . . . ?
C5 O3 C8 O5A -28.6(14) . . . . ?
C5 O3 C8 O5B 32.7(12) . . . . ?
C5 O3 C8 C9 -177.9(3) . . . . ?
C5 C4 C3 O2 -61.2(2) . . . . ?
C5 C4 C3 C2 178.21(16) . . . . ?
C6 O1 C1 C2 -83.6(2) . . . . ?
C8 O3 C5 C4 113.8(3) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
# D H A D - H H...A D...A D - H...A symm(A)
# - - - ----- ----- ----- --------- -------
O2 H2O O4 0.8200 2.5600 3.283(2) 148.00 2_655 yes
#===END
#===============================================================================
data_tetraacetate_beta_form_RT
_database_code_depnum_ccdc_archive 'CCDC 724610'
#===============================================================================
_audit_creation_date 'Mar 02 19:52:37 2009'
_audit_creation_method 'PLATON option'
# 5. CHEMICAL DATA
_chemical_name_systematic
;
(all trans)-3,6,7-tri(acetyloxy)-4a,8a-dihydroxyperhydro-2-naphthalenyl acetate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C18 H26 O10'
_chemical_formula_structural 'C18 H26 O10'
_chemical_formula_sum 'C18 H26 O10'
_chemical_formula_iupac 'C18 H26 O10'
_chemical_formula_weight 402.39
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_Int_Tables_number 15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
_cell_length_a 19.991(5)
_cell_length_b 6.0024(15)
_cell_length_c 16.225(4)
_cell_angle_alpha 90
_cell_angle_beta 91.130(4)
_cell_angle_gamma 90
_cell_volume 1946.6(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 291(2)
_cell_measurement_reflns_used 815
_cell_measurement_theta_min 3.20
_cell_measurement_theta_max 23.69
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.21
_exptl_crystal_size_min 0.12
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.373
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 856
_exptl_absorpt_coefficient_mu 0.113
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min 0.9467
_exptl_absorpt_correction_T_max 0.9866
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 291(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoKa
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
_diffrn_reflns_number 6976
_diffrn_reflns_av_R_equivalents 0.0170
_diffrn_reflns_av_sigmaI/netI 0.0151
_diffrn_reflns_limit_h_min -24
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.04
_diffrn_reflns_theta_max 25.49
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_reduction_process
;
;
_reflns_number_total 1807
_reflns_number_gt 1475
_reflns_threshold_expression I>2sigma(I)
_computing_data_collection 'SMART (Bruker, 1998)'
_computing_cell_refinement 'SMART (Bruker, 1998)'
_computing_data_reduction 'SAINT (Bruker, 1998)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_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^)+(0.0574P)^2^+1.1118P] 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 1807
_refine_ls_number_parameters 130
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0505
_refine_ls_R_factor_gt 0.0405
_refine_ls_wR_factor_ref 0.1114
_refine_ls_wR_factor_gt 0.1061
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_restrained_S_all 1.049
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.275
_refine_diff_density_min -0.188
_refine_diff_density_rms 0.039
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.03766(6) 1.17528(17) 1.07846(7) 0.0393(3) Uani 1 1 d . . .
H2O H 0.0667 1.1457 1.1132 0.059 Uiso 1 1 calc R . .
O3 O 0.09515(6) 0.73153(19) 0.85914(7) 0.0406(3) Uani 1 1 d . . .
O1 O 0.16588(6) 1.0086(2) 1.03415(7) 0.0436(3) Uani 1 1 d . . .
C2 C 0.06336(8) 0.7886(3) 1.04549(9) 0.0363(4) Uani 1 1 d . . .
H2A H 0.0778 0.7617 1.1020 0.044 Uiso 1 1 calc R . .
H2B H 0.0428 0.6526 1.0249 0.044 Uiso 1 1 calc R . .
O5 O 0.11257(9) 0.9225(2) 0.74297(8) 0.0710(5) Uani 1 1 d . . .
C3 C 0.01069(8) 0.9726(2) 1.04487(8) 0.0319(4) Uani 1 1 d . . .
C1 C 0.12447(8) 0.8388(3) 0.99461(10) 0.0382(4) Uani 1 1 d . . .
H1 H 0.1509 0.7022 0.9891 0.046 Uiso 1 1 calc R . .
C4 C -0.05026(8) 0.9040(3) 1.09395(9) 0.0375(4) Uani 1 1 d . . .
H4A H -0.0663 0.7620 1.0730 0.045 Uiso 1 1 calc R . .
H4B H -0.0363 0.8820 1.1510 0.045 Uiso 1 1 calc R . .
O4 O 0.22163(7) 0.7449(3) 1.10557(10) 0.0687(5) Uani 1 1 d . . .
C5 C 0.10809(8) 0.9306(3) 0.90848(9) 0.0376(4) Uani 1 1 d . . .
H5 H 0.1480 1.0047 0.8876 0.045 Uiso 1 1 calc R . .
C8 C 0.10206(10) 0.7493(3) 0.77760(10) 0.0466(5) Uani 1 1 d . . .
C6 C 0.21299(9) 0.9375(3) 1.08871(11) 0.0480(5) Uani 1 1 d . . .
C9 C 0.09482(12) 0.5305(3) 0.73531(11) 0.0604(6) Uani 1 1 d . . .
H9A H 0.0551 0.5316 0.7010 0.091 Uiso 1 1 calc R . .
H9B H 0.0915 0.4144 0.7757 0.091 Uiso 1 1 calc R . .
H9C H 0.1331 0.5044 0.7019 0.091 Uiso 1 1 calc R . .
C7 C 0.25180(10) 1.1282(4) 1.12330(14) 0.0675(6) Uani 1 1 d . . .
H7A H 0.2561 1.1121 1.1820 0.101 Uiso 1 1 calc R . .
H7B H 0.2289 1.2648 1.1105 0.101 Uiso 1 1 calc R . .
H7C H 0.2955 1.1307 1.0997 0.101 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
O2 0.0490(7) 0.0349(6) 0.0336(6) -0.0044(5) -0.0076(5) -0.0046(5)
O3 0.0538(7) 0.0393(7) 0.0289(6) -0.0034(5) 0.0034(5) -0.0033(5)
O1 0.0433(7) 0.0448(7) 0.0423(6) -0.0032(5) -0.0074(5) -0.0031(5)
C2 0.0476(9) 0.0332(8) 0.0281(7) 0.0035(6) -0.0043(7) -0.0010(7)
O5 0.1267(14) 0.0499(8) 0.0370(7) 0.0040(6) 0.0169(8) 0.0022(9)
C3 0.0433(9) 0.0281(8) 0.0243(7) -0.0003(6) -0.0021(6) -0.0044(6)
C1 0.0433(9) 0.0359(9) 0.0353(8) -0.0026(7) -0.0030(7) -0.0001(7)
C4 0.0505(10) 0.0349(9) 0.0271(7) 0.0036(6) 0.0013(7) -0.0044(7)
O4 0.0623(9) 0.0636(10) 0.0791(11) 0.0099(8) -0.0227(8) 0.0058(7)
C5 0.0443(9) 0.0381(9) 0.0306(8) -0.0024(7) 0.0026(7) -0.0067(7)
C8 0.0617(11) 0.0478(11) 0.0303(9) -0.0005(7) 0.0025(8) 0.0067(9)
C6 0.0381(9) 0.0624(13) 0.0433(9) -0.0006(9) -0.0022(7) 0.0019(9)
C9 0.0911(16) 0.0526(12) 0.0372(10) -0.0083(8) -0.0062(10) 0.0071(11)
C7 0.0487(12) 0.0820(16) 0.0711(14) -0.0089(12) -0.0172(10) -0.0091(11)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_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
O2 C3 1.4337(18) . ?
O2 H2O 0.8200 . ?
O3 C8 1.337(2) . ?
O3 C5 1.4586(19) . ?
O1 C6 1.349(2) . ?
O1 C1 1.455(2) . ?
C2 C1 1.518(2) . ?
C2 C3 1.526(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O5 C8 1.202(2) . ?
C3 C4 1.525(2) . ?
C1 C5 1.532(2) . ?
C1 H1 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O4 C6 1.200(2) . ?
C5 H5 0.9800 . ?
C8 C9 1.487(3) . ?
C6 C7 1.487(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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 O2 H2O 109.5 . . ?
C8 O3 C5 117.19(13) . . ?
C6 O1 C1 116.83(14) . . ?
C1 C2 C3 114.53(13) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
O2 C3 C4 109.19(12) . . ?
O2 C3 C2 110.94(12) . . ?
C4 C3 C2 111.05(13) . . ?
O1 C1 C2 110.88(13) . . ?
O1 C1 C5 105.05(13) . . ?
C2 C1 C5 114.07(13) . . ?
O1 C1 H1 108.9 . . ?
C2 C1 H1 108.9 . . ?
C5 C1 H1 108.9 . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
O3 C5 C1 103.78(13) . . ?
O3 C5 H5 108.6 . . ?
C1 C5 H5 108.6 . . ?
O5 C8 O3 123.64(16) . . ?
O5 C8 C9 124.34(16) . . ?
O3 C8 C9 112.02(15) . . ?
O4 C6 O1 123.39(18) . . ?
O4 C6 C7 125.73(18) . . ?
O1 C6 C7 110.88(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
C1 C2 C3 O2 -61.11(17) . . . . ?
C1 C2 C3 C4 177.25(13) . . . . ?
C6 O1 C1 C2 88.50(17) . . . . ?
C6 O1 C1 C5 -147.82(14) . . . . ?
C3 C2 C1 O1 71.78(17) . . . . ?
C3 C2 C1 C5 -46.57(19) . . . . ?
C8 O3 C5 C1 -157.51(15) . . . . ?
O1 C1 C5 O3 154.67(12) . . . . ?
C2 C1 C5 O3 -83.71(16) . . . . ?
C5 O3 C8 O5 -6.5(3) . . . . ?
C5 O3 C8 C9 173.78(15) . . . . ?
C1 O1 C6 O4 -0.2(3) . . . . ?
C1 O1 C6 C7 179.34(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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
# D H A D - H H...A D...A D - H...A symm(A)
# - - - ----- ----- ----- --------- -------
O2 H2O O5 0.8200 2.3200 3.091(2) 158.00 4_575 yes
#===END
#===============================================================================
data_tetraacetate_beta_form_100K
_database_code_depnum_ccdc_archive 'CCDC 724611'
#===============================================================================
_audit_creation_date 'Mar 02 19:52:37 2009'
_audit_creation_method 'PLATON option'
# 5. CHEMICAL DATA
_chemical_name_systematic
;
(all trans)-3,6,7-tri(acetyloxy)-4a,8a-dihydroxyperhydro-2-naphthalenyl acetate
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C18 H26 O10'
_chemical_formula_structural 'C18 H26 O10'
_chemical_formula_sum 'C18 H26 O10'
_chemical_formula_iupac 'C18 H26 O10'
_chemical_formula_weight 402.39
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_Hall '-C 2yc'
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_Int_Tables_number 15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
_cell_length_a 19.430(4)
_cell_length_b 6.0815(13)
_cell_length_c 15.994(3)
_cell_angle_alpha 90
_cell_angle_beta 91.849(4)
_cell_angle_gamma 90
_cell_volume 1889.0(7)
_cell_formula_units_Z 4
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 739
_cell_measurement_theta_min 2.55
_cell_measurement_theta_max 27.13
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.28
_exptl_crystal_size_mid 0.24
_exptl_crystal_size_min 0.20
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.415
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 856
_exptl_absorpt_coefficient_mu 0.116
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min 0.9374
_exptl_absorpt_correction_T_max 0.9772
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoKa
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
_diffrn_reflns_number 7047
_diffrn_reflns_av_R_equivalents 0.0245
_diffrn_reflns_av_sigmaI/netI 0.0231
_diffrn_reflns_limit_h_min -23
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.10
_diffrn_reflns_theta_max 25.99
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_reduction_process
;
;
_reflns_number_total 1853
_reflns_number_gt 1588
_reflns_threshold_expression I>2sigma(I)
_computing_data_collection 'SMART (Bruker, 1998)'
_computing_cell_refinement 'SMART (Bruker, 1998)'
_computing_data_reduction 'SAINT (Bruker, 1998)'
_computing_structure_solution 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'PLATON (Spek, 2003)'
#===============================================================================
# 8. REFINEMENT DATA
_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^)+(0.0396P)^2^+1.3854P] 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 refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 1853
_refine_ls_number_parameters 179
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0431
_refine_ls_R_factor_gt 0.0343
_refine_ls_wR_factor_ref 0.0827
_refine_ls_wR_factor_gt 0.0795
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_restrained_S_all 1.034
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.376
_refine_diff_density_min -0.209
_refine_diff_density_rms 0.042
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.90364(5) 0.27263(15) 0.14089(6) 0.0157(2) Uani 1 1 d . . .
O2 O 1.03980(5) 0.17678(15) 0.07805(6) 0.0156(2) Uani 1 1 d . . .
O3 O 0.82897(5) -0.01015(16) -0.03528(6) 0.0165(2) Uani 1 1 d . . .
O4 O 0.88816(5) 0.08462(16) 0.26038(6) 0.0208(3) Uani 1 1 d . . .
O5 O 0.77636(5) 0.24612(17) -0.11716(7) 0.0241(3) Uani 1 1 d . . .
C1 C 0.88928(7) 0.0727(2) 0.09210(8) 0.0149(3) Uani 1 1 d . . .
C2 C 0.94889(7) -0.0911(2) 0.09589(8) 0.0149(3) Uani 1 1 d . . .
C3 C 1.01131(7) -0.0250(2) 0.04558(8) 0.0132(3) Uani 1 1 d . . .
C4 C 0.93452(7) 0.2077(2) -0.04780(8) 0.0147(3) Uani 1 1 d . . .
C5 C 0.87167(7) 0.1600(2) 0.00410(8) 0.0148(3) Uani 1 1 d . . .
C6 C 0.89844(7) 0.2566(2) 0.22392(8) 0.0160(3) Uani 1 1 d . . .
C7 C 0.90691(8) 0.4738(2) 0.26687(9) 0.0194(3) Uani 1 1 d . . .
C8 C 0.78365(7) 0.0566(2) -0.09615(8) 0.0180(3) Uani 1 1 d . . .
C9 C 0.74413(8) -0.1344(3) -0.13197(10) 0.0241(4) Uani 1 1 d . . .
H2O H 1.0683(10) 0.144(3) 0.1182(13) 0.039(5) Uiso 1 1 d . . .
H1 H 0.8480(7) 0.009(2) 0.1146(9) 0.013(4) Uiso 1 1 d . . .
H2A H 0.9644(7) -0.115(2) 0.1530(9) 0.012(4) Uiso 1 1 d . . .
H2B H 0.9312(8) -0.231(3) 0.0755(10) 0.018(4) Uiso 1 1 d . . .
H4A H 0.9543(8) 0.347(3) -0.0287(9) 0.014(4) Uiso 1 1 d . . .
H4B H 0.9188(8) 0.233(2) -0.1050(10) 0.016(4) Uiso 1 1 d . . .
H5 H 0.8439(7) 0.292(2) 0.0083(9) 0.010(4) Uiso 1 1 d . . .
H7A H 0.9468(9) 0.468(3) 0.3057(11) 0.030(5) Uiso 1 1 d . . .
H7B H 0.8671(10) 0.501(3) 0.2999(12) 0.038(5) Uiso 1 1 d . . .
H7C H 0.9129(8) 0.593(3) 0.2292(11) 0.026(4) Uiso 1 1 d . . .
H9A H 0.6992(11) -0.122(3) -0.1147(12) 0.045(6) Uiso 1 1 d . . .
H9B H 0.7630(9) -0.275(3) -0.1137(11) 0.033(5) Uiso 1 1 d . . .
H9C H 0.7429(10) -0.126(3) -0.1934(13) 0.045(6) Uiso 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
O1 0.0202(5) 0.0154(5) 0.0115(5) -0.0011(4) 0.0014(4) -0.0015(4)
O2 0.0184(5) 0.0149(5) 0.0131(5) -0.0013(4) -0.0034(4) -0.0019(4)
O3 0.0159(5) 0.0185(5) 0.0150(5) -0.0006(4) -0.0023(4) -0.0011(4)
O4 0.0292(6) 0.0191(5) 0.0143(5) 0.0014(4) 0.0022(4) -0.0007(4)
O5 0.0220(6) 0.0233(6) 0.0265(6) 0.0038(4) -0.0050(4) 0.0016(4)
C1 0.0170(7) 0.0152(7) 0.0126(7) -0.0017(5) 0.0012(5) -0.0025(5)
C2 0.0188(7) 0.0140(7) 0.0118(7) 0.0016(5) -0.0004(5) -0.0013(6)
C3 0.0161(7) 0.0130(7) 0.0104(7) -0.0008(5) -0.0008(5) -0.0020(5)
C4 0.0185(7) 0.0139(7) 0.0117(6) 0.0010(5) -0.0011(5) -0.0010(5)
C5 0.0155(7) 0.0139(7) 0.0148(7) -0.0011(5) -0.0015(5) -0.0004(6)
C6 0.0138(7) 0.0213(8) 0.0129(6) 0.0006(6) -0.0005(5) 0.0017(5)
C7 0.0256(8) 0.0188(8) 0.0136(7) -0.0011(6) -0.0003(6) 0.0007(6)
C8 0.0133(7) 0.0252(8) 0.0155(7) 0.0006(6) 0.0020(5) 0.0013(6)
C9 0.0178(8) 0.0282(9) 0.0259(8) -0.0018(7) -0.0036(6) -0.0019(7)
#===============================================================================
# 10. MOLECULAR GEOMETRY
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4665(16) . ?
O1 C6 1.3387(17) . ?
O2 C3 1.4363(16) . ?
O2 H2O 0.86(2) . ?
O3 C5 1.4568(16) . ?
O3 C8 1.3538(16) . ?
O4 C6 1.2172(17) . ?
O5 C8 1.2078(18) . ?
C1 H1 0.970(15) . ?
C2 C1 1.527(2) . ?
C2 C3 1.5306(19) . ?
C2 H2A 0.964(15) . ?
C2 H2B 0.971(16) . ?
C4 H4A 0.975(15) . ?
C4 H4B 0.968(16) . ?
C5 C1 1.5326(18) . ?
C5 C4 1.526(2) . ?
C5 H5 0.973(15) . ?
C6 C7 1.495(2) . ?
C7 H7A 0.978(18) . ?
C7 H7B 0.97(2) . ?
C7 H7C 0.955(18) . ?
C8 C9 1.496(2) . ?
C9 H9A 0.93(2) . ?
C9 H9B 0.974(19) . ?
C9 H9C 0.98(2) . ?
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
O1 C1 C2 112.86(11) . . ?
O1 C1 C5 103.57(11) . . ?
O1 C1 H1 106.2(9) . . ?
O1 C6 C7 112.38(12) . . ?
O2 C3 C2 109.69(10) . . ?
O3 C5 C1 104.96(11) . . ?
O3 C5 C4 110.75(11) . . ?
O3 C5 H5 107.9(8) . . ?
O3 C8 C9 110.89(13) . . ?
O4 C6 O1 123.82(13) . . ?
O4 C6 C7 123.80(12) . . ?
O5 C8 O3 123.64(13) . . ?
O5 C8 C9 125.47(13) . . ?
C1 C2 C3 114.88(11) . . ?
C1 C2 H2A 110.4(9) . . ?
C1 C2 H2B 107.3(9) . . ?
C1 C5 H5 109.3(8) . . ?
C2 C1 C5 114.13(11) . . ?
C2 C1 H1 111.1(9) . . ?
C3 O2 H2O 107.7(13) . . ?
C3 C2 H2A 108.0(9) . . ?
C3 C2 H2B 109.4(9) . . ?
C4 C5 C1 113.98(11) . . ?
C4 C5 H5 109.7(8) . . ?
C5 C1 H1 108.5(9) . . ?
C5 C4 H4A 108.0(9) . . ?
C5 C4 H4B 108.1(9) . . ?
C6 O1 C1 116.64(10) . . ?
C6 C7 H7A 109.6(10) . . ?
C6 C7 H7B 109.1(11) . . ?
C6 C7 H7C 113.4(10) . . ?
C8 O3 C5 116.50(11) . . ?
C8 C9 H9A 107.2(12) . . ?
C8 C9 H9B 112.7(11) . . ?
C8 C9 H9C 109.6(11) . . ?
H2B C2 H2A 106.5(12) . . ?
H4B C4 H4A 105.5(12) . . ?
H7A C7 H7B 107.0(15) . . ?
H7A C7 H7C 108.5(14) . . ?
H7B C7 H7C 109.2(15) . . ?
H9B C9 H9A 109.4(16) . . ?
H9B C9 H9C 110.2(15) . . ?
H9C C9 H9A 107.5(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
O3 C5 C1 O1 -155.46(10) . . . . ?
O3 C5 C1 C2 81.45(13) . . . . ?
C1 O1 C6 O4 6.08(19) . . . . ?
C1 O1 C6 C7 -174.09(11) . . . . ?
C1 C2 C3 O2 61.96(14) . . . . ?
C3 C2 C1 O1 -73.19(14) . . . . ?
C3 C2 C1 C5 44.70(16) . . . . ?
C4 C5 C1 O1 83.19(13) . . . . ?
C4 C5 C1 C2 -39.90(16) . . . . ?
C5 O3 C8 O5 -1.65(19) . . . . ?
C5 O3 C8 C9 179.09(11) . . . . ?
C6 O1 C1 C2 -77.40(14) . . . . ?
C6 O1 C1 C5 158.67(11) . . . . ?
C8 O3 C5 C1 152.92(11) . . . . ?
C8 O3 C5 C4 -83.63(14) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# ======== ======= ======
#
# D H A D - H H...A D...A D - H...A symm(A)
# - - - ----- ----- ----- --------- -------
O2 H2O O4 0.86(2) 2.12(2) 2.9526(15) 162.3(18) 2_755 yes
#===END