# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         177

loop_
_publ_author_name
'Peter Langer'
'Olumide Fatunsin'
'Christine Fischer'
'Ibrar Hussain'
'Mathias Lubbe'
'Stefanie Reim'
'Helmut Reinke'
'Abdolmajid Riahi'
'Mohanad Shkoor'
'Mirza A. Yawer'

_publ_contact_author_name        'Peter Langer'
_publ_contact_author_email       PETER.LANGER@UNI-ROSTOCK.DE

_publ_section_title              
;
Diversity-Oriented Synthesis of 1-Hydroxy-2,4-benzodioates
by Regioselective [3+3] Cyclocondensations of 1,3-Bis(silyloxy)-1,3-butadienes
with 3-Alkoxy- and 3-Silyloxy-2-alkoxycarbonyl-2-en-1-ones
;

# Attachment 'OBC090106.cif'

data_mr285c2(7b)
_database_code_depnum_ccdc_archive 'CCDC 718444'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Dimethyl 4-hydroxy-2,5-dimethylisophthalate
;
_chemical_name_common            ?
_chemical_melting_point          383
_chemical_formula_moiety         'C12 H14 O4'
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23

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 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4507(4)
_cell_length_b                   10.6081(6)
_cell_length_c                   14.7549(9)
_cell_angle_alpha                77.052(4)
_cell_angle_beta                 78.918(3)
_cell_angle_gamma                81.775(3)
_cell_volume                     1109.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5857
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      30.21

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9435
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_process_details   'SADABS, Bruker (2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29877
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         30.65
_reflns_number_total             6765
_reflns_number_gt                4253
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0662P)^2^+0.1306P] 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         6765
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1407
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.007
_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
O1A O 0.16816(16) 0.00936(10) 0.23000(8) 0.0415(3) Uani 1 1 d . . .
O2A O 0.11390(14) 0.15441(10) 0.10046(7) 0.0355(2) Uani 1 1 d . . .
O3A O -0.02910(16) 0.06161(11) 0.38342(8) 0.0397(3) Uani 1 1 d . . .
H3A H 0.048(3) 0.015(2) 0.3387(18) 0.093(8) Uiso 1 1 d . . .
O4A O -0.05036(17) 0.64562(11) 0.14344(9) 0.0493(3) Uani 1 1 d . . .
C1A C 0.05038(16) 0.22743(13) 0.24460(9) 0.0250(3) Uani 1 1 d . . .
C2A C -0.02730(17) 0.18840(14) 0.34048(10) 0.0272(3) Uani 1 1 d . . .
C3A C -0.10735(17) 0.27928(15) 0.39579(10) 0.0295(3) Uani 1 1 d . . .
C4A C -0.09869(17) 0.40867(14) 0.35436(10) 0.0289(3) Uani 1 1 d . . .
H4A H -0.1490 0.4719 0.3914 0.035 Uiso 1 1 calc R . .
C5A C -0.01899(17) 0.45187(14) 0.25984(10) 0.0269(3) Uani 1 1 d . . .
C6A C 0.05835(16) 0.36098(13) 0.20315(9) 0.0238(3) Uani 1 1 d . . .
C7A C 0.11896(17) 0.12118(14) 0.19200(10) 0.0289(3) Uani 1 1 d . . .
C8A C 0.1845(2) 0.05515(17) 0.04538(12) 0.0442(4) Uani 1 1 d . . .
H8A1 H 0.3165 0.0330 0.0464 0.066 Uiso 1 1 calc R . .
H8A2 H 0.1644 0.0880 -0.0198 0.066 Uiso 1 1 calc R . .
H8A3 H 0.1204 -0.0226 0.0724 0.066 Uiso 1 1 calc R . .
C9A C -0.1967(2) 0.23433(17) 0.49661(10) 0.0395(4) Uani 1 1 d . . .
H9A1 H -0.2602 0.3096 0.5221 0.059 Uiso 1 1 calc R . .
H9A2 H -0.1024 0.1907 0.5343 0.059 Uiso 1 1 calc R . .
H9A3 H -0.2857 0.1735 0.4989 0.059 Uiso 1 1 calc R . .
C10A C -0.02365(19) 0.59555(15) 0.22307(11) 0.0332(3) Uani 1 1 d . . .
C11A C 0.0011(2) 0.67879(16) 0.28921(13) 0.0461(4) Uani 1 1 d . . .
H11A H 0.0379 0.7630 0.2527 0.069 Uiso 1 1 calc R . .
H11B H 0.0965 0.6351 0.3262 0.069 Uiso 1 1 calc R . .
H11C H -0.1151 0.6925 0.3318 0.069 Uiso 1 1 calc R . .
C12A C 0.15963(18) 0.40470(14) 0.10413(10) 0.0296(3) Uani 1 1 d . . .
H12A H 0.0774 0.4098 0.0587 0.044 Uiso 1 1 calc R . .
H12B H 0.2669 0.3421 0.0915 0.044 Uiso 1 1 calc R . .
H12C H 0.2003 0.4905 0.0981 0.044 Uiso 1 1 calc R . .
O1B O 0.51216(16) 0.62820(10) 0.29360(8) 0.0401(3) Uani 1 1 d . . .
O2B O 0.46994(14) 0.60212(9) 0.15312(7) 0.0353(3) Uani 1 1 d . . .
O3B O 0.37649(15) 0.44669(12) 0.43018(8) 0.0386(3) Uani 1 1 d . . .
H3B H 0.422(3) 0.526(2) 0.3989(15) 0.068(7) Uiso 1 1 d . . .
O4B O 0.59552(16) 0.11525(11) 0.10249(7) 0.0411(3) Uani 1 1 d . . .
C1B C 0.49787(16) 0.41331(13) 0.27126(9) 0.0234(3) Uani 1 1 d . . .
C2B C 0.42553(17) 0.36706(14) 0.36682(10) 0.0264(3) Uani 1 1 d . . .
C3B C 0.39943(17) 0.23598(14) 0.40133(9) 0.0267(3) Uani 1 1 d . . .
C4B C 0.46002(17) 0.15226(13) 0.33957(9) 0.0260(3) Uani 1 1 d . . .
H4B H 0.4457 0.0625 0.3619 0.031 Uiso 1 1 calc R . .
C5B C 0.54177(16) 0.19365(13) 0.24536(9) 0.0229(3) Uani 1 1 d . . .
C6B C 0.56220(15) 0.32647(13) 0.20928(9) 0.0220(3) Uani 1 1 d . . .
C7B C 0.49839(18) 0.55660(14) 0.24124(10) 0.0288(3) Uani 1 1 d . . .
C8B C 0.4715(3) 0.74124(15) 0.11885(13) 0.0496(4) Uani 1 1 d . . .
H8B1 H 0.3855 0.7872 0.1627 0.074 Uiso 1 1 calc R . .
H8B2 H 0.4343 0.7654 0.0565 0.074 Uiso 1 1 calc R . .
H8B3 H 0.5957 0.7651 0.1141 0.074 Uiso 1 1 calc R . .
C9B C 0.3108(2) 0.19020(17) 0.50181(10) 0.0373(4) Uani 1 1 d . . .
H9B1 H 0.2915 0.0983 0.5119 0.056 Uiso 1 1 calc R . .
H9B2 H 0.1921 0.2418 0.5145 0.056 Uiso 1 1 calc R . .
H9B3 H 0.3909 0.2007 0.5445 0.056 Uiso 1 1 calc R . .
C10B C 0.60144(18) 0.09275(14) 0.18641(10) 0.0280(3) Uani 1 1 d . . .
C11B C 0.6695(2) -0.04173(15) 0.23495(12) 0.0410(4) Uani 1 1 d . . .
H11D H 0.5643 -0.0905 0.2654 0.061 Uiso 1 1 calc R . .
H11E H 0.7408 -0.0347 0.2826 0.061 Uiso 1 1 calc R . .
H11F H 0.7477 -0.0873 0.1883 0.061 Uiso 1 1 calc R . .
C12B C 0.66454(17) 0.37279(14) 0.11083(9) 0.0263(3) Uani 1 1 d . . .
H12D H 0.7541 0.3023 0.0921 0.039 Uiso 1 1 calc R . .
H12E H 0.7289 0.4474 0.1102 0.039 Uiso 1 1 calc R . .
H12F H 0.5769 0.3986 0.0666 0.039 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.0561(7) 0.0270(6) 0.0395(7) -0.0041(5) -0.0077(5) -0.0024(5)
O2A 0.0444(6) 0.0363(6) 0.0279(6) -0.0109(5) -0.0085(4) -0.0007(4)
O3A 0.0504(6) 0.0318(6) 0.0315(6) 0.0053(5) -0.0041(5) -0.0085(5)
O4A 0.0658(8) 0.0355(7) 0.0419(7) 0.0021(6) -0.0142(6) 0.0019(5)
C1A 0.0233(6) 0.0280(7) 0.0236(7) -0.0032(6) -0.0057(5) -0.0030(5)
C2A 0.0261(6) 0.0296(8) 0.0249(7) 0.0006(6) -0.0069(5) -0.0052(5)
C3A 0.0244(6) 0.0392(9) 0.0235(7) -0.0024(6) -0.0056(5) -0.0024(5)
C4A 0.0278(6) 0.0334(8) 0.0256(8) -0.0076(6) -0.0064(5) 0.0020(5)
C5A 0.0247(6) 0.0287(7) 0.0271(7) -0.0042(6) -0.0069(5) -0.0014(5)
C6A 0.0215(5) 0.0274(7) 0.0223(7) -0.0018(5) -0.0065(5) -0.0029(5)
C7A 0.0279(6) 0.0290(8) 0.0301(8) -0.0046(6) -0.0052(5) -0.0057(5)
C8A 0.0540(9) 0.0441(10) 0.0401(10) -0.0216(8) -0.0042(7) -0.0082(7)
C9A 0.0348(7) 0.0539(11) 0.0248(8) -0.0009(7) -0.0025(6) -0.0030(7)
C10A 0.0318(7) 0.0296(8) 0.0356(9) -0.0043(7) -0.0047(6) 0.0007(5)
C11A 0.0541(10) 0.0315(9) 0.0537(11) -0.0145(8) -0.0077(8) -0.0004(7)
C12A 0.0286(6) 0.0314(8) 0.0268(8) -0.0020(6) -0.0014(5) -0.0074(5)
O1B 0.0603(7) 0.0292(6) 0.0335(6) -0.0088(5) -0.0118(5) -0.0048(5)
O2B 0.0529(6) 0.0232(5) 0.0302(6) 0.0017(4) -0.0159(5) -0.0047(4)
O3B 0.0515(6) 0.0374(7) 0.0254(6) -0.0114(5) 0.0011(5) -0.0022(5)
O4B 0.0638(7) 0.0368(6) 0.0243(6) -0.0082(5) -0.0123(5) -0.0010(5)
C1B 0.0241(6) 0.0245(7) 0.0210(7) -0.0024(5) -0.0054(5) -0.0025(5)
C2B 0.0259(6) 0.0300(7) 0.0228(7) -0.0063(6) -0.0033(5) -0.0007(5)
C3B 0.0237(6) 0.0346(8) 0.0201(7) -0.0013(6) -0.0022(5) -0.0055(5)
C4B 0.0273(6) 0.0256(7) 0.0239(7) 0.0013(6) -0.0060(5) -0.0066(5)
C5B 0.0245(5) 0.0246(7) 0.0198(7) -0.0029(5) -0.0058(5) -0.0029(5)
C6B 0.0207(5) 0.0251(7) 0.0192(6) -0.0010(5) -0.0050(4) -0.0026(4)
C7B 0.0313(6) 0.0284(8) 0.0262(8) -0.0037(6) -0.0063(5) -0.0023(5)
C8B 0.0822(13) 0.0244(8) 0.0405(10) 0.0031(7) -0.0176(9) -0.0049(8)
C9B 0.0354(7) 0.0493(10) 0.0236(8) -0.0018(7) 0.0023(6) -0.0114(6)
C10B 0.0327(6) 0.0279(7) 0.0244(8) -0.0047(6) -0.0070(5) -0.0049(5)
C11B 0.0627(10) 0.0267(8) 0.0334(9) -0.0069(7) -0.0129(7) 0.0038(7)
C12B 0.0259(6) 0.0299(7) 0.0209(7) -0.0011(6) -0.0019(5) -0.0046(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
O1A C7A 1.2298(17) . ?
O2A C7A 1.3238(17) . ?
O2A C8A 1.4514(18) . ?
O3A C2A 1.3530(17) . ?
O3A H3A 0.96(3) . ?
O4A C10A 1.2174(18) . ?
C1A C2A 1.4139(19) . ?
C1A C6A 1.4164(19) . ?
C1A C7A 1.4861(19) . ?
C2A C3A 1.397(2) . ?
C3A C4A 1.377(2) . ?
C3A C9A 1.509(2) . ?
C4A C5A 1.407(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.4066(19) . ?
C5A C10A 1.497(2) . ?
C6A C12A 1.5139(19) . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
C10A C11A 1.506(2) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
O1B C7B 1.2248(17) . ?
O2B C7B 1.3282(17) . ?
O2B C8B 1.4498(18) . ?
O3B C2B 1.3621(17) . ?
O3B H3B 0.94(2) . ?
O4B C10B 1.2156(17) . ?
C1B C2B 1.4117(19) . ?
C1B C6B 1.4134(18) . ?
C1B C7B 1.4852(19) . ?
C2B C3B 1.397(2) . ?
C3B C4B 1.3831(19) . ?
C3B C9B 1.5043(19) . ?
C4B C5B 1.4048(18) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.4091(18) . ?
C5B C10B 1.4942(19) . ?
C6B C12B 1.5147(18) . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9B H9B1 0.9800 . ?
C9B H9B2 0.9800 . ?
C9B H9B3 0.9800 . ?
C10B C11B 1.510(2) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 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
C7A O2A C8A 116.68(12) . . ?
C2A O3A H3A 104.6(14) . . ?
C2A C1A C6A 120.52(12) . . ?
C2A C1A C7A 116.08(12) . . ?
C6A C1A C7A 123.39(12) . . ?
O3A C2A C3A 116.47(13) . . ?
O3A C2A C1A 122.01(13) . . ?
C3A C2A C1A 121.52(13) . . ?
C4A C3A C2A 117.11(13) . . ?
C4A C3A C9A 122.72(13) . . ?
C2A C3A C9A 120.17(14) . . ?
C3A C4A C5A 123.24(13) . . ?
C3A C4A H4A 118.4 . . ?
C5A C4A H4A 118.4 . . ?
C6A C5A C4A 119.94(13) . . ?
C6A C5A C10A 122.41(13) . . ?
C4A C5A C10A 117.64(12) . . ?
C5A C6A C1A 117.57(12) . . ?
C5A C6A C12A 120.77(12) . . ?
C1A C6A C12A 121.48(12) . . ?
O1A C7A O2A 121.90(13) . . ?
O1A C7A C1A 123.49(13) . . ?
O2A C7A C1A 114.52(12) . . ?
O2A C8A H8A1 109.5 . . ?
O2A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
O2A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C3A C9A H9A1 109.5 . . ?
C3A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C3A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
O4A C10A C5A 122.19(14) . . ?
O4A C10A C11A 120.14(14) . . ?
C5A C10A C11A 117.65(13) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C6A C12A H12A 109.5 . . ?
C6A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C6A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C7B O2B C8B 116.42(12) . . ?
C2B O3B H3B 105.1(13) . . ?
C2B C1B C6B 120.89(12) . . ?
C2B C1B C7B 115.85(12) . . ?
C6B C1B C7B 123.26(12) . . ?
O3B C2B C3B 116.32(12) . . ?
O3B C2B C1B 122.36(12) . . ?
C3B C2B C1B 121.31(12) . . ?
C4B C3B C2B 117.05(12) . . ?
C4B C3B C9B 122.47(13) . . ?
C2B C3B C9B 120.48(13) . . ?
C3B C4B C5B 123.14(13) . . ?
C3B C4B H4B 118.4 . . ?
C5B C4B H4B 118.4 . . ?
C4B C5B C6B 120.00(12) . . ?
C4B C5B C10B 117.57(12) . . ?
C6B C5B C10B 122.42(12) . . ?
C5B C6B C1B 117.39(11) . . ?
C5B C6B C12B 121.29(12) . . ?
C1B C6B C12B 121.09(12) . . ?
O1B C7B O2B 122.34(13) . . ?
O1B C7B C1B 123.92(13) . . ?
O2B C7B C1B 113.60(12) . . ?
O2B C8B H8B1 109.5 . . ?
O2B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
O2B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C3B C9B H9B1 109.5 . . ?
C3B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
C3B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
O4B C10B C5B 122.50(13) . . ?
O4B C10B C11B 119.94(13) . . ?
C5B C10B C11B 117.56(12) . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C6B C12B H12D 109.5 . . ?
C6B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C6B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 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
C6A C1A C2A O3A -176.77(11) . . . . ?
C7A C1A C2A O3A 3.87(18) . . . . ?
C6A C1A C2A C3A 3.57(18) . . . . ?
C7A C1A C2A C3A -175.78(11) . . . . ?
O3A C2A C3A C4A 176.96(11) . . . . ?
C1A C2A C3A C4A -3.36(18) . . . . ?
O3A C2A C3A C9A -2.47(18) . . . . ?
C1A C2A C3A C9A 177.20(12) . . . . ?
C2A C3A C4A C5A 1.90(19) . . . . ?
C9A C3A C4A C5A -178.68(12) . . . . ?
C3A C4A C5A C6A -0.59(19) . . . . ?
C3A C4A C5A C10A 178.31(12) . . . . ?
C4A C5A C6A C1A 0.65(17) . . . . ?
C10A C5A C6A C1A -178.19(11) . . . . ?
C4A C5A C6A C12A -174.52(11) . . . . ?
C10A C5A C6A C12A 6.64(18) . . . . ?
C2A C1A C6A C5A -2.11(17) . . . . ?
C7A C1A C6A C5A 177.20(11) . . . . ?
C2A C1A C6A C12A 173.02(11) . . . . ?
C7A C1A C6A C12A -7.67(18) . . . . ?
C8A O2A C7A O1A -5.21(19) . . . . ?
C8A O2A C7A C1A 178.22(11) . . . . ?
C2A C1A C7A O1A -25.06(18) . . . . ?
C6A C1A C7A O1A 155.60(13) . . . . ?
C2A C1A C7A O2A 151.44(11) . . . . ?
C6A C1A C7A O2A -27.90(17) . . . . ?
C6A C5A C10A O4A 37.4(2) . . . . ?
C4A C5A C10A O4A -141.49(14) . . . . ?
C6A C5A C10A C11A -144.22(14) . . . . ?
C4A C5A C10A C11A 36.91(17) . . . . ?
C6B C1B C2B O3B 174.46(11) . . . . ?
C7B C1B C2B O3B -6.48(17) . . . . ?
C6B C1B C2B C3B -5.91(18) . . . . ?
C7B C1B C2B C3B 173.14(11) . . . . ?
O3B C2B C3B C4B -175.72(11) . . . . ?
C1B C2B C3B C4B 4.63(18) . . . . ?
O3B C2B C3B C9B 3.65(18) . . . . ?
C1B C2B C3B C9B -176.00(12) . . . . ?
C2B C3B C4B C5B -1.14(18) . . . . ?
C9B C3B C4B C5B 179.50(12) . . . . ?
C3B C4B C5B C6B -1.17(18) . . . . ?
C3B C4B C5B C10B 179.84(11) . . . . ?
C4B C5B C6B C1B 0.03(17) . . . . ?
C10B C5B C6B C1B 178.96(11) . . . . ?
C4B C5B C6B C12B 174.56(11) . . . . ?
C10B C5B C6B C12B -6.50(17) . . . . ?
C2B C1B C6B C5B 3.41(17) . . . . ?
C7B C1B C6B C5B -175.58(11) . . . . ?
C2B C1B C6B C12B -171.14(11) . . . . ?
C7B C1B C6B C12B 9.87(18) . . . . ?
C8B O2B C7B O1B 5.1(2) . . . . ?
C8B O2B C7B C1B -179.11(12) . . . . ?
C2B C1B C7B O1B 29.94(18) . . . . ?
C6B C1B C7B O1B -151.03(13) . . . . ?
C2B C1B C7B O2B -145.76(12) . . . . ?
C6B C1B C7B O2B 33.27(17) . . . . ?
C4B C5B C10B O4B 146.37(14) . . . . ?
C6B C5B C10B O4B -32.59(19) . . . . ?
C4B C5B C10B C11B -33.09(17) . . . . ?
C6B C5B C10B C11B 147.95(13) . . . . ?

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
O3B H3B O1B 0.94(2) 1.76(2) 2.6124(16) 149.6(19) .
O3A H3A O1A 0.96(3) 1.69(3) 2.5772(16) 151(2) .

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        30.65
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046

#======================================================================

#_eof # next file follows

#======================================================================

data_of110(7k)
_database_code_depnum_ccdc_archive 'CCDC 718445'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Dimethyl 4'-chloro-2-hydroxy-4-methylbiphenyl-3,5-dicarboxylate
;
_chemical_name_common            ?
_chemical_melting_point          433
_chemical_formula_moiety         'C17 H15 Cl O5'
_chemical_formula_sum            'C17 H15 Cl O5'
_chemical_formula_weight         334.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n '
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.0186(2)
_cell_length_b                   33.9422(15)
_cell_length_c                   11.3074(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.435(3)
_cell_angle_gamma                90.00
_cell_volume                     1525.65(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1727
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      21.76

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8639
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   'SADABS, Bruker (2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8127
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_sigmaI/netI    0.0799
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         24.54
_reflns_number_total             2550
_reflns_number_gt                1535
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0462P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2550
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.899
_refine_ls_restrained_S_all      0.899
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.3808(2) 0.26095(2) 1.22315(7) 0.0631(3) Uani 1 1 d . . .
O1 O 0.5887(10) 0.50049(7) 0.8864(2) 0.1499(16) Uani 1 1 d D . .
O2 O 0.7454(6) 0.51329(6) 0.71950(17) 0.0673(6) Uani 1 1 d . . .
O3 O 0.5530(6) 0.43228(7) 0.96884(17) 0.0588(6) Uani 1 1 d . . .
H3O H 0.509(9) 0.4581(11) 0.967(3) 0.100(14) Uiso 1 1 d . . .
O4 O 0.8837(6) 0.38180(6) 0.44957(17) 0.0622(6) Uani 1 1 d . . .
O5 O 1.1145(5) 0.33637(5) 0.57846(15) 0.0470(5) Uani 1 1 d . . .
C1 C 0.7332(6) 0.44583(7) 0.7770(2) 0.0377(7) Uani 1 1 d . . .
C2 C 0.6601(7) 0.41957(8) 0.8679(2) 0.0386(7) Uani 1 1 d . . .
C3 C 0.6910(6) 0.37880(7) 0.8560(2) 0.0324(6) Uani 1 1 d . . .
C4 C 0.7905(6) 0.36520(8) 0.7521(2) 0.0351(7) Uani 1 1 d . . .
H4 H 0.8128 0.3382 0.7427 0.042 Uiso 1 1 calc R . .
C5 C 0.8598(6) 0.38985(8) 0.6601(2) 0.0340(6) Uani 1 1 d . . .
C6 C 0.8377(6) 0.43072(8) 0.6718(2) 0.0360(6) Uani 1 1 d . . .
C7 C 0.6870(8) 0.48822(9) 0.8002(3) 0.0507(8) Uani 1 1 d D . .
C8 C 0.7064(9) 0.55468(8) 0.7440(3) 0.0700(10) Uani 1 1 d . . .
H8A H 0.5743 0.5577 0.8076 0.105 Uiso 0.27(3) 1 calc PR A 1
H8B H 0.5953 0.5675 0.6734 0.105 Uiso 0.27(3) 1 calc PR A 1
H8C H 0.9239 0.5663 0.7671 0.105 Uiso 0.27(3) 1 calc PR A 1
H8D H 0.8135 0.5605 0.8236 0.105 Uiso 0.73(3) 1 calc PR A 2
H8E H 0.4715 0.5610 0.7368 0.105 Uiso 0.73(3) 1 calc PR A 2
H8F H 0.8085 0.5701 0.6877 0.105 Uiso 0.73(3) 1 calc PR A 2
C9 C 0.6139(6) 0.35041(7) 0.9488(2) 0.0331(6) Uani 1 1 d . . .
C10 C 0.7088(7) 0.35689(8) 1.0711(2) 0.0427(7) Uani 1 1 d . . .
H10 H 0.8215 0.3800 1.0965 0.051 Uiso 1 1 calc R . .
C11 C 0.6389(7) 0.32974(9) 1.1549(2) 0.0477(8) Uani 1 1 d . . .
H11 H 0.7042 0.3345 1.2360 0.057 Uiso 1 1 calc R . .
C12 C 0.4716(7) 0.29546(8) 1.1175(2) 0.0404(7) Uani 1 1 d . . .
C13 C 0.3750(6) 0.28814(8) 0.9979(2) 0.0395(7) Uani 1 1 d . . .
H13 H 0.2622 0.2650 0.9731 0.047 Uiso 1 1 calc R . .
C14 C 0.4472(6) 0.31549(7) 0.9150(2) 0.0367(7) Uani 1 1 d . . .
H14 H 0.3822 0.3104 0.8341 0.044 Uiso 1 1 calc R . .
C15 C 0.9507(7) 0.37058(8) 0.5509(2) 0.0396(7) Uani 1 1 d . . .
C16 C 1.2052(8) 0.31409(9) 0.4803(3) 0.0570(9) Uani 1 1 d . . .
H16A H 1.0052 0.3047 0.4316 0.085 Uiso 1 1 calc R . .
H16B H 1.3425 0.2921 0.5104 0.085 Uiso 1 1 calc R . .
H16C H 1.3286 0.3306 0.4331 0.085 Uiso 1 1 calc R . .
C17 C 0.9350(8) 0.45707(8) 0.5747(2) 0.0530(8) Uani 1 1 d . . .
H17A H 0.7356 0.4672 0.5274 0.080 Uiso 1 1 calc R . .
H17B H 1.0620 0.4422 0.5246 0.080 Uiso 1 1 calc R . .
H17C H 1.0693 0.4785 0.6104 0.080 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0878(6) 0.0531(5) 0.0524(5) 0.0210(4) 0.0233(4) 0.0024(5)
O1 0.343(5) 0.0356(15) 0.106(2) 0.0038(14) 0.148(3) 0.021(2)
O2 0.1170(19) 0.0297(12) 0.0619(14) 0.0039(11) 0.0356(13) 0.0012(12)
O3 0.1037(18) 0.0364(13) 0.0438(12) 0.0006(10) 0.0358(11) 0.0126(13)
O4 0.1037(18) 0.0511(14) 0.0340(12) 0.0027(10) 0.0168(11) 0.0112(12)
O5 0.0598(13) 0.0425(12) 0.0397(11) -0.0064(9) 0.0111(9) 0.0104(10)
C1 0.0465(18) 0.0297(16) 0.0386(15) 0.0029(13) 0.0118(13) 0.0006(13)
C2 0.0490(17) 0.0319(17) 0.0363(15) -0.0033(13) 0.0110(13) 0.0018(14)
C3 0.0373(15) 0.0309(16) 0.0290(14) 0.0003(12) 0.0046(12) 0.0016(13)
C4 0.0394(16) 0.0294(15) 0.0354(15) -0.0007(12) 0.0021(12) 0.0025(13)
C5 0.0364(16) 0.0359(16) 0.0300(14) 0.0004(12) 0.0057(12) 0.0005(13)
C6 0.0387(16) 0.0357(17) 0.0348(15) 0.0010(12) 0.0089(12) -0.0024(13)
C7 0.079(2) 0.0333(17) 0.0442(17) -0.0006(15) 0.0242(16) 0.0010(16)
C8 0.111(3) 0.0285(19) 0.077(2) 0.0024(16) 0.036(2) -0.0021(19)
C9 0.0387(16) 0.0280(16) 0.0325(15) 0.0015(12) 0.0050(12) 0.0053(12)
C10 0.0551(18) 0.0367(17) 0.0349(16) -0.0009(13) 0.0021(14) -0.0056(14)
C11 0.062(2) 0.051(2) 0.0289(15) 0.0025(14) 0.0032(14) 0.0054(16)
C12 0.0490(18) 0.0346(17) 0.0397(17) 0.0143(13) 0.0129(14) 0.0074(14)
C13 0.0467(17) 0.0298(16) 0.0426(17) 0.0005(13) 0.0083(14) -0.0027(13)
C14 0.0451(16) 0.0345(16) 0.0304(14) 0.0020(12) 0.0050(12) 0.0043(14)
C15 0.0432(17) 0.0376(18) 0.0397(17) -0.0004(14) 0.0114(14) -0.0029(14)
C16 0.067(2) 0.053(2) 0.0558(19) -0.0172(16) 0.0249(16) 0.0046(17)
C17 0.076(2) 0.0420(19) 0.0466(17) 0.0037(14) 0.0263(16) -0.0031(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
Cl1 C12 1.749(3) . ?
O1 C7 1.180(3) . ?
O2 C7 1.294(3) . ?
O2 C8 1.445(3) . ?
O3 C2 1.348(3) . ?
O3 H3O 0.89(4) . ?
O4 C15 1.200(3) . ?
O5 C15 1.349(3) . ?
O5 C16 1.434(3) . ?
C1 C6 1.414(3) . ?
C1 C2 1.424(3) . ?
C1 C7 1.479(4) . ?
C2 C3 1.398(3) . ?
C3 C4 1.375(3) . ?
C3 C9 1.491(3) . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(3) . ?
C5 C15 1.490(3) . ?
C6 C17 1.511(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8D 0.9600 . ?
C8 H8E 0.9600 . ?
C8 H8F 0.9600 . ?
C9 C14 1.387(3) . ?
C9 C10 1.397(3) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(3) . ?
C13 C14 1.380(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C7 O2 C8 117.9(2) . . ?
C2 O3 H3O 112(2) . . ?
C15 O5 C16 116.5(2) . . ?
C6 C1 C2 119.9(2) . . ?
C6 C1 C7 124.2(2) . . ?
C2 C1 C7 115.8(2) . . ?
O3 C2 C3 116.3(2) . . ?
O3 C2 C1 122.4(2) . . ?
C3 C2 C1 121.3(2) . . ?
C4 C3 C2 117.1(2) . . ?
C4 C3 C9 120.1(2) . . ?
C2 C3 C9 122.8(2) . . ?
C3 C4 C5 123.4(2) . . ?
C3 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 C15 117.1(2) . . ?
C6 C5 C15 122.7(2) . . ?
C5 C6 C1 118.0(2) . . ?
C5 C6 C17 119.5(2) . . ?
C1 C6 C17 122.5(2) . . ?
O1 C7 O2 117.9(3) . . ?
O1 C7 C1 123.8(3) . . ?
O2 C7 C1 118.3(2) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
O2 C8 H8D 109.5 . . ?
O2 C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
O2 C8 H8F 109.5 . . ?
H8D C8 H8F 109.5 . . ?
H8E C8 H8F 109.5 . . ?
C14 C9 C10 117.3(2) . . ?
C14 C9 C3 120.0(2) . . ?
C10 C9 C3 122.7(2) . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 Cl1 119.6(2) . . ?
C11 C12 Cl1 119.8(2) . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 121.9(2) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
O4 C15 O5 121.8(2) . . ?
O4 C15 C5 127.2(3) . . ?
O5 C15 C5 110.9(2) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O3 -178.6(3) . . . . ?
C7 C1 C2 O3 0.4(4) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C7 C1 C2 C3 179.4(3) . . . . ?
O3 C2 C3 C4 178.2(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
O3 C2 C3 C9 -0.5(4) . . . . ?
C1 C2 C3 C9 -179.5(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C9 C3 C4 C5 178.6(2) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C3 C4 C5 C15 -177.4(2) . . . . ?
C4 C5 C6 C1 -2.0(4) . . . . ?
C15 C5 C6 C1 176.9(2) . . . . ?
C4 C5 C6 C17 176.1(2) . . . . ?
C15 C5 C6 C17 -4.9(4) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C7 C1 C6 C5 -177.9(3) . . . . ?
C2 C1 C6 C17 -177.0(2) . . . . ?
C7 C1 C6 C17 4.0(4) . . . . ?
C8 O2 C7 O1 3.8(5) . . . . ?
C8 O2 C7 C1 -178.7(3) . . . . ?
C6 C1 C7 O1 177.3(4) . . . . ?
C2 C1 C7 O1 -1.7(5) . . . . ?
C6 C1 C7 O2 0.0(4) . . . . ?
C2 C1 C7 O2 -179.0(3) . . . . ?
C4 C3 C9 C14 -38.9(3) . . . . ?
C2 C3 C9 C14 139.7(3) . . . . ?
C4 C3 C9 C10 139.8(3) . . . . ?
C2 C3 C9 C10 -41.6(4) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C3 C9 C10 C11 -178.9(2) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C10 C11 C12 Cl1 -179.8(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
Cl1 C12 C13 C14 179.96(19) . . . . ?
C12 C13 C14 C9 -0.3(4) . . . . ?
C10 C9 C14 C13 0.3(4) . . . . ?
C3 C9 C14 C13 179.1(2) . . . . ?
C16 O5 C15 O4 0.1(4) . . . . ?
C16 O5 C15 C5 177.7(2) . . . . ?
C4 C5 C15 O4 145.7(3) . . . . ?
C6 C5 C15 O4 -33.3(4) . . . . ?
C4 C5 C15 O5 -31.7(3) . . . . ?
C6 C5 C15 O5 149.3(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
O3 H3O O1 0.89(4) 1.76(4) 2.508(3) 140(3) .
O3 H3O O1 0.89(4) 2.25(3) 2.913(3) 130(3) 3_667

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.54
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.059

#======================================================================

#_eof # End of Crystallographic Information File