#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/64/2006410.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006410
loop_
_publ_author_name
'Gable, Robert W.'
'Gan, Chee Yong'
'Lambert, John N.'
_publ_section_title
;
 Methyl 8-Hydroxy-1,2,3,4-tetrahydronaphthalene-5-carboxylate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1122
_journal_page_last               1124
_journal_paper_doi               10.1107/S0108270197002898
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C12 H14 O3'
_chemical_formula_weight         206.23
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.2699(9)
_cell_length_b                   6.833(2)
_cell_length_c                   19.9199(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293.0(10)
_cell_measurement_theta_max      45.3
_cell_measurement_theta_min      18.1
_cell_volume                     2078.4(6)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-96
_computing_structure_refinement  'SHELXL-96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.0(10)
_diffrn_measurement_device       'Enraf-Nonius CAD-4MachS diffractometer'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'CuK\a (nickel filtered)'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3067
_diffrn_reflns_theta_max         74.94
_diffrn_reflns_theta_min         3.65
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  160
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   'Gaussian integration (Sheldrick, 1976)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.122
_refine_ls_extinction_coef       0.00046(13)
_refine_ls_extinction_method     'SHELXL96 (Sheldrick, 1996)'
_refine_ls_goodness_of_fit_all   1.027
_refine_ls_goodness_of_fit_obs   1.151
_refine_ls_hydrogen_treatment
'H atoms refined geometrically, except for H13 and H13'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.011
_refine_ls_restrained_S_obs      1.116
_refine_ls_R_factor_all          0.095
_refine_ls_R_factor_obs          .050
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0720P)²+0.2200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.151
_refine_ls_wR_factor_obs         .121
_reflns_number_observed          1347
_reflns_number_total             2333
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            kh1143.cif
_cod_data_source_block           jl_2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.2200P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.2200P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2006410
_cod_database_fobs_code          2006410
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
'x-1/2, y, -z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 -.1028(2) .2500 .42503(17) .0516(10) Uani d SPD .895(4) 1 C
H1A -.1426 .3391 .4475 .034(11) Uiso calc PR .447(2) 1 H
H1B -.1128 .1199 .4429 .073(18) Uiso calc PR .447(2) 1 H
C2 -.0096(5) .3105(15) .4399(3) .063(2) Uani d PD .447(2) 1 C
H2A .0033 .2918 .4871 .055(12) Uiso calc PR .447(2) 1 H
H2B -.0012 .4476 .4290 .08(2) Uiso calc PR .447(2) 1 H
C3 .0508(3) .1825(10) .3968(2) .060(2) Uani d PD .447(2) 1 C
H3A .0354 .0455 .4017 .059(16) Uiso calc PR .447(2) 1 H
H3B .1114 .1996 .4103 .054(13) Uiso calc PR .447(2) 1 H
C4 .0378(2) .2500 .3224(2) .0486(14) Uani d SPD .895(4) 1 C
H4A .0614 .3810 .3172 .053(14) Uiso calc PR .447(2) 1 H
H4B .0706 .1636 .2931 .038(12) Uiso calc PR .447(2) 1 H
C4a -.0572(2) .2500 .30119(17) .0367(8) Uani d SPD .895(4) 1 C
C5 -.08085(19) .2500 .23319(19) .0344(7) Uani d SPD .895(4) 1 C
C6 -.16946(18) .2500 .21573(15) .0387(7) Uani d SPD .895(4) 1 C
H6 -.1849 .2500 .1706 .064(12) Uiso calc SPR .895(4) 1 H
C7 -.23386(18) .2500 .26314(16) .0410(8) Uani d SPD .895(4) 1 C
H7 -.2925 .2500 .2506 .057(11) Uiso calc SPR .895(4) 1 H
C8 -.21027(18) .2500 .33068(15) .0381(7) Uani d SPD .895(4) 1 C
C8a -.12232(18) .2500 .35023(15) .0376(7) Uani d SPD .895(4) 1 C
C9 -.0155(3) .2500 .17829(16) .0387(8) Uani d SPD .895(4) 1 C
O10 .06353(17) .2500 .18456(12) .0583(8) Uani d SPD .895(4) 1 O
O11 -.05293(14) .2500 .11765(10) .0542(7) Uani d SPD .895(4) 1 O
C12 .0063(3) .2500 .06126(17) .0597(12) Uani d SPD .895(4) 1 C
H12A -.0256 .2788 .0209 .057(13) Uiso calc PR .447(2) 1 H
H12B .0333 .1236 .0573 .054(18) Uiso calc PR .447(2) 1 H
H12C .0507 .3476 .0680 .09(3) Uiso calc PR .447(2) 1 H
O13 -.27245(14) .2500 .37979(11) .0504(7) Uani d SPD .895(4) 1 O
H13 -.329(2) .2500 .3577(19) .070(12) Uiso d SPD .895(4) 1 H
C1B .375(2) .2500 .4197(14) .108(16) Uiso d SPD .105(4) 2 C
H1A_b .3349 .3427 .4404 .141 Uiso calc PR .053(2) 2 H
H1B_b .3614 .1211 .4373 .141 Uiso calc PR .053(2) 2 H
C2B .467(3) .303(15) .438(3) .19(6) Uiso d PD .053(2) 2 C
H2A_b .4778 .2739 .4850 .244 Uiso calc PR .053(2) 2 H
H2B_b .4766 .4421 .4311 .244 Uiso calc PR .053(2) 2 H
C3B .530(3) .185(13) .394(2) .14(3) Uiso d PD .053(2) 2 C
H3A_b .5172 .0464 .3978 .187 Uiso calc PR .053(2) 2 H
H3B_b .5901 .2058 .4087 .187 Uiso calc PR .053(2) 2 H
C4B .521(2) .2500 .319(2) .08(3) Uiso d SPD .105(4) 2 C
H4A_b .5448 .3806 .3140 .100 Uiso calc PR .053(2) 2 H
H4B_b .5547 .1625 .2909 .100 Uiso calc PR .053(2) 2 H
C4aB .427(2) .2500 .2953(14) .077(17) Uiso d SPD .105(4) 2 C
C5B .403(2) .2500 .2278(13) .12(2) Uiso d SPD .105(4) 2 C
C6B .313(2) .2500 .2107(18) .20(3) Uiso d SPD .105(4) 2 C
H6B .2971 .2500 .1656 .222 Uiso calc SPR .105(4) 2 H
C7B .248(2) .2500 .2579(17) .20(3) Uiso d SPD .105(4) 2 C
H7B .1894 .2500 .2454 .222 Uiso calc SPR .105(4) 2 H
C8B .272(2) .2500 .3254(16) .121(19) Uiso d SPD .105(4) 2 C
C8aB .3601(19) .2500 .3445(14) .15(2) Uiso d SPD .105(4) 2 C
C9B .469(2) .2500 .1742(14) .067(13) Uiso d SPD .105(4) 2 C
O10B .547(2) .2500 .182(3) .13(2) Uiso d SPD .105(4) 2 O
O11B .436(2) .2500 .1118(16) .157(18) Uiso d SPD .105(4) 2 O
C12B .502(3) .2500 .060(2) .031(12) Uiso d SPD .105(4) 2 C
H12AB .4861 .3397 .0251 .047 Uiso calc PR .053(2) 2 H
H12B_b .5079 .1207 .0417 .047 Uiso calc PR .053(2) 2 H
H12C_b .5573 .2896 .0792 .047 Uiso calc PR .053(2) 2 H
O13B .210(2) .2500 .3753(17) .145(16) Uiso d SPD .105(4) 2 O
H13_b .154(3) .2500 .353(4) .160 Uiso d SPD .105(4) 2 H
C1' .1313(2) .2500 .91955(15) .0504(10) Uani d SPD .895(4) 1 C
H1A' .1218 .1195 .9373 .043(13) Uiso calc PR .447(2) 1 H
H1B' .0908 .3380 .9419 .079(19) Uiso calc PR .447(2) 1 H
C2' .2247(3) .3134(11) .9348(2) .060(2) Uani d PD .447(2) 1 C
H2A' .2324 .4507 .9239 .054(16) Uiso calc PR .447(2) 1 H
H2B' .2373 .2955 .9822 .056(13) Uiso calc PR .447(2) 1 H
C3' .2856(3) .1896(10) .8930(2) .061(2) Uani d PD .447(2) 1 C
H3A' .2719 .0521 .8988 .08(2) Uiso calc PR .447(2) 1 H
H3B' .3458 .2109 .9067 .051(12) Uiso calc PR .447(2) 1 H
C4' .2732(3) .2500 .81847(18) .0490(11) Uani d SPD .895(4) 1 C
H4A' .2973 .3799 .8119 .059(16) Uiso calc PR .447(2) 1 H
H4B' .3056 .1602 .7901 .036(12) Uiso calc PR .447(2) 1 H
C4a' .17850(18) .2500 .79720(17) .0341(7) Uani d SPD .895(4) 1 C
C5' .15428(17) .2500 .72760(15) .0339(7) Uani d SPD .895(4) 1 C
C6' .0663(2) .2500 .71036(16) .0397(8) Uani d SPD .895(4) 1 C
H6' .0509 .2500 .6652 .031(14) Uiso calc SPR .895(4) 1 H
C7' .0009(2) .2500 .7582(2) .0393(8) Uani d SPD .895(4) 1 C
H7' -.0577 .2500 .7456 .029(8) Uiso calc SPR .895(4) 1 H
C8' .02469(18) .2500 .82537(15) .0379(7) Uani d SPD .895(4) 1 C
C8a' .11238(18) .2500 .84486(14) .0352(7) Uani d SPD .895(4) 1 C
C9' .2214(2) .2500 .67384(16) .0390(8) Uani d SPD .895(4) 1 C
O10' .2991(3) .2500 .68109(19) .064(2) Uani d SPD .895(4) 1 O
O11' .18518(15) .2500 .61254(11) .0550(7) Uani d SPD .895(4) 1 O
C12' .2457(3) .2500 .5570(2) .0676(18) Uani d SPD .895(4) 1 C
H12A' .2158 .2895 .5169 .061(14) Uiso calc PR .447(2) 1 H
H12B' .2691 .1207 .5510 .08(2) Uiso calc PR .447(2) 1 H
H12C' .2926 .3397 .5661 .058(17) Uiso calc PR .447(2) 1 H
O13' -.03715(13) .2500 .87486(11) .0512(7) Uani d SPD .895(4) 1 O
H13' -.101(3) .2500 .856(2) .084(13) Uiso d SPD .895(4) 1 H
C1'B .646(3) .2500 .9244(15) .14(2) Uiso d SPD .105(4) 2 C
H1A'_b .6321 .1221 .9427 .183 Uiso calc PR .053(2) 2 H
H1B'_b .6083 .3452 .9462 .183 Uiso calc PR .053(2) 2 H
C2'B .741(3) .299(14) .940(3) .13(3) Uiso d PD .053(2) 2 C
H2A'_b .7523 .4366 .9322 .174 Uiso calc PR .053(2) 2 H
H2B'_b .7539 .2706 .9869 .174 Uiso calc PR .053(2) 2 H
C3'B .799(3) .175(11) .895(2) .13(3) Uiso d PD .053(2) 2 C
H3A'_b .7827 .0387 .8982 .174 Uiso calc PR .053(2) 2 H
H3B'_b .8601 .1876 .9089 .174 Uiso calc PR .053(2) 2 H
C4'B .788(2) .2500 .822(2) .06(3) Uiso d SPD .105(4) 2 C
H4A'_b .8111 .3817 .8183 .084 Uiso calc PR .053(2) 2 H
H4B'_b .8208 .1666 .7916 .084 Uiso calc PR .053(2) 2 H
C4a'B .6924(17) .2500 .8016(12) .049(10) Uiso d SPD .105(4) 2 C
C5'B .6694(17) .2500 .7320(12) .050(11) Uiso d SPD .105(4) 2 C
C6'B .5817(19) .2500 .7141(17) .19(3) Uiso d SPD .105(4) 2 C
H6'_b .5654 .2500 .6691 .211 Uiso calc SPR .105(4) 2 H
C7'B .519(2) .2500 .7637(16) .066(17) Uiso d SPD .105(4) 2 C
H7'_b .4601 .2500 .7512 .072 Uiso calc SPR .105(4) 2 H
C8'B .5393(19) .2500 .8309(16) .15(5) Uiso d SPD .105(4) 2 C
C8a'B .6274(18) .2500 .8499(14) .13(2) Uiso d SPD .105(4) 2 C
C9'B .7374(17) .2500 .6801(12) .056(13) Uiso d SPD .105(4) 2 C
O10'B .8148(17) .2500 .6871(17) .102(14) Uiso d SPD .105(4) 2 O
O11'B .702(2) .2500 .6185(13) .127(13) Uiso d SPD .105(4) 2 O
C12'B .758(4) .2500 .562(2) .11(3) Uiso d SPD .105(4) 2 C
H12A'_b .7352 .3351 .5282 .167 Uiso calc PR .053(2) 2 H
H12B'_b .7630 .1195 .5446 .167 Uiso calc PR .053(2) 2 H
H12C'_b .8153 .2954 .5755 .167 Uiso calc PR .053(2) 2 H
O13'B .479(2) .2500 .8815(16) .144(16) Uiso d SPD .105(4) 2 O
H13'_b .414(3) .2500 .863(4) .159 Uiso d SPD .105(4) 2 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8a 112.2(4) y
C2 C1 H1A 109.2(4) ?
C8a C1 H1A 109.17(13) ?
C2 C1 H1B 109.2(4) ?
C8a C1 H1B 109.17(4) ?
H1A C1 H1B 107.9 ?
C1 C2 C3 107.5(5) y
C1 C2 H2A 110.2(3) ?
C3 C2 H2A 110.2(3) ?
C1 C2 H2B 110.2(4) ?
C3 C2 H2B 110.2(4) ?
H2A C2 H2B 108.5 ?
C2 C3 C4 106.6(4) y
C2 C3 H3A 110.4(4) ?
C4 C3 H3A 110.4(2) ?
C2 C3 H3B 110.4(3) ?
C4 C3 H3B 110.4(2) ?
H3A C3 H3B 108.6 ?
C4a C4 C3 112.8(3) y
C4a C4 H4A 109.03(5) ?
C3 C4 H4A 109.0(2) ?
C4a C4 H4B 109.03(17) ?
C3 C4 H4B 109.0(2) ?
H4A C4 H4B 107.8 ?
C8a C4a C5 119.5(3) ?
C8a C4a C4 119.3(3) y
C5 C4a C4 121.2(3) ?
C6 C5 C4a 119.4(3) ?
C6 C5 C9 117.9(3) ?
C4a C5 C9 122.7(3) ?
C7 C6 C5 121.7(3) ?
C7 C6 H6 119.13(18) ?
C5 C6 H6 119.1(2) ?
C6 C7 C8 118.8(3) ?
C6 C7 H7 120.58(18) ?
C8 C7 H7 120.58(16) ?
O13 C8 C7 120.9(3) ?
O13 C8 C8a 118.0(3) ?
C7 C8 C8a 121.2(3) ?
C4a C8a C8 119.4(3) ?
C4a C8a C1 123.1(3) y
C8 C8a C1 117.5(3) ?
O10 C9 O11 121.2(3) y
O10 C9 C5 126.5(3) y
O11 C9 C5 112.3(3) y
C9 O11 C12 115.9(3) y
O11 C12 H12A 109.5(2) ?
O11 C12 H12B 109.47(7) ?
H12A C12 H12B 109.5 ?
O11 C12 H12C 109.47(15) ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C8 O13 H13 107(2) ?
C2_b C1_b C8a_b 112(2) ?
C2_b C1_b H1A_b 109(3) ?
C8a_b C1_b H1A_b 109.1(10) ?
C2_b C1_b H1B_b 109(4) ?
C8a_b C1_b H1B_b 109.1(4) ?
H1A_b C1_b H1B_b 107.9 ?
C1_b C2_b C3_b 109(3) ?
C1_b C2_b H2A_b 110(3) ?
C3_b C2_b H2A_b 110(3) ?
C1_b C2_b H2B_b 110(4) ?
C3_b C2_b H2B_b 110(3) ?
H2A_b C2_b H2B_b 108.3 ?
C2_b C3_b C4_b 110(3) ?
C2_b C3_b H3A_b 110(3) ?
C4_b C3_b H3A_b 110(3) ?
C2_b C3_b H3B_b 110(2) ?
C4_b C3_b H3B_b 110(2) ?
H3A_b C3_b H3B_b 108.2 ?
C4a_b C4_b C3_b 113(2) ?
C4a_b C4_b H4A_b 109.0(3) ?
C3_b C4_b H4A_b 109(3) ?
C4a_b C4_b H4B_b 109.0(11) ?
C3_b C4_b H4B_b 109(2) ?
H4A_b C4_b H4B_b 107.8 ?
C5_b C4a_b C8a_b 118.5(19) ?
C5_b C4a_b C4_b 124(2) ?
C8a_b C4a_b C4_b 117.9(19) ?
C4a_b C5_b C6_b 119(2) ?
C4a_b C5_b C9_b 121(2) ?
C6_b C5_b C9_b 120(2) ?
C7_b C6_b C5_b 122(2) ?
C7_b C6_b H6_b 118.8(17) ?
C5_b C6_b H6_b 118.8(14) ?
C6_b C7_b C8_b 118(2) ?
C6_b C7_b H7_b 120.8(17) ?
C8_b C7_b H7_b 120.8(15) ?
O13_b C8_b C7_b 121(2) ?
O13_b C8_b C8a_b 118(2) ?
C7_b C8_b C8a_b 121(2) ?
C8_b C8a_b C4a_b 120.3(19) ?
C8_b C8a_b C1_b 114.3(19) ?
C4a_b C8a_b C1_b 125.4(19) ?
O10_b C9_b O11_b 119(3) ?
O10_b C9_b C5_b 127(3) ?
O11_b C9_b C5_b 114(2) ?
C9_b O11_b C12_b 113(3) ?
O11_b C12_b H12A_b 109.5(18) ?
O11_b C12_b H12B_b 109.5(5) ?
H12A_b C12_b H12B_b 109.5 ?
O11_b C12_b H12C_b 109(2) ?
H12A_b C12_b H12C_b 109.5 ?
H12B_b C12_b H12C_b 109.5 ?
C8_b O13_b H13_b 106(3) ?
C2' C1' C8a' 112.0(3) y
C8a' C1' H1A' 109.21(4) ?
C2' C1' H1A' 109.2(3) ?
C8a' C1' H1B' 109.21(12) ?
C2' C1' H1B' 109.2(3) ?
H1A' C1' H1B' 107.9 ?
C1' C2' C3' 107.9(4) y
C3' C2' H2A' 110.1(3) ?
C1' C2' H2A' 110.1(3) ?
C3' C2' H2B' 110.1(3) ?
C1' C2' H2B' 110.1(2) ?
H2A' C2' H2B' 108.4 ?
C2' C3' C4' 107.7(4) y
C2' C3' H3A' 110.2(3) ?
C4' C3' H3A' 110.2(2) ?
C2' C3' H3B' 110.2(2) ?
C4' C3' H3B' 110.2(2) ?
H3A' C3' H3B' 108.5 ?
C4a' C4' C3' 112.7(3) y
C4a' C4' H4A' 109.05(5) ?
C3' C4' H4A' 109.1(3) ?
C4a' C4' H4B' 109.05(15) ?
C3' C4' H4B' 109.1(2) ?
H4A' C4' H4B' 107.8 ?
C8a' C4a' C5' 118.3(3) ?
C8a' C4a' C4' 120.4(3) y
C5' C4a' C4' 121.3(3) ?
C6' C5' C4a' 119.3(3) ?
C6' C5' C9' 119.4(3) ?
C4a' C5' C9' 121.3(2) ?
C7' C6' C5' 122.0(3) ?
C7' C6' H6' 119.00(17) ?
C5' C6' H6' 119.00(18) ?
C6' C7' C8' 118.5(3) ?
C6' C7' H7' 120.75(17) ?
C8' C7' H7' 120.75(19) ?
O13' C8' C7' 121.1(3) ?
O13' C8' C8a' 117.6(3) ?
C7' C8' C8a' 121.3(3) ?
C4a' C8a' C8' 120.6(3) ?
C4a' C8a' C1' 122.3(3) y
C8' C8a' C1' 117.1(3) ?
O10' C9' O11' 121.3(4) y
O10' C9' C5' 126.8(3) y
O11' C9' C5' 111.9(3) y
C9' O11' C12' 115.7(3) y
O11' C12' H12A' 109.5(2) ?
O11' C12' H12B' 109.47(5) ?
H12A' C12' H12B' 109.5 ?
O11' C12' H12C' 109.47(16) ?
H12A' C12' H12C' 109.5 ?
H12B' C12' H12C' 109.5 ?
C8' O13' H13' 112(2) ?
C8a'_b C1'_b C2'_b 112(2) ?
C8a'_b C1'_b H1A'_b 109.1(4) ?
C2'_b C1'_b H1A'_b 109(4) ?
C8a'_b C1'_b H1B'_b 109.1(10) ?
C2'_b C1'_b H1B'_b 109(3) ?
H1A'_b C1'_b H1B'_b 107.9 ?
C3'_b C2'_b C1'_b 108(3) ?
C3'_b C2'_b H2A'_b 110(3) ?
C1'_b C2'_b H2A'_b 110(4) ?
C3'_b C2'_b H2B'_b 110(3) ?
C1'_b C2'_b H2B'_b 110(3) ?
H2A'_b C2'_b H2B'_b 108.4 ?
C2'_b C3'_b C4'_b 108(3) ?
C2'_b C3'_b H3A'_b 110(3) ?
C4'_b C3'_b H3A'_b 110(3) ?
C2'_b C3'_b H3B'_b 110(2) ?
C4'_b C3'_b H3B'_b 110.1(19) ?
H3A'_b C3'_b H3B'_b 108.5 ?
C4a'_b C4'_b C3'_b 111(2) ?
C4a'_b C4'_b H4A'_b 109.4(3) ?
C3'_b C4'_b H4A'_b 109(3) ?
C4a'_b C4'_b H4B'_b 109.4(12) ?
C3'_b C4'_b H4B'_b 109(2) ?
H4A'_b C4'_b H4B'_b 108.0 ?
C8a'_b C4a'_b C5'_b 119.9(18) ?
C8a'_b C4a'_b C4'_b 120.4(19) ?
C5'_b C4a'_b C4'_b 119.7(19) ?
C6'_b C5'_b C4a'_b 119.1(19) ?
C6'_b C5'_b C9'_b 120.3(19) ?
C4a'_b C5'_b C9'_b 120.6(18) ?
C7'_b C6'_b C5'_b 119(2) ?
C7'_b C6'_b H6'_b 120.3(15) ?
C5'_b C6'_b H6'_b 120.3(14) ?
C8'_b C7'_b C6'_b 123(2) ?
C8'_b C7'_b H7'_b 118.7(14) ?
C6'_b C7'_b H7'_b 118.7(15) ?
O13'_b C8'_b C7'_b 124(2) ?
O13'_b C8'_b C8a'_b 117(2) ?
C7'_b C8'_b C8a'_b 119(2) ?
C4a'_b C8a'_b C8'_b 120.2(19) ?
C4a'_b C8a'_b C1'_b 123.3(19) ?
C8'_b C8a'_b C1'_b 116.5(19) ?
O10'_b C9'_b O11'_b 121(2) ?
O10'_b C9'_b C5'_b 128(2) ?
O11'_b C9'_b C5'_b 111(2) ?
C9'_b O11'_b C12'_b 118(3) ?
O11'_b C12'_b H12A'_b 109.5(19) ?
O11'_b C12'_b H12B'_b 109.5(5) ?
H12A'_b C12'_b H12B'_b 109.5 ?
O11'_b C12'_b H12C'_b 109(2) ?
H12A'_b C12'_b H12C'_b 109.5 ?
H12B'_b C12'_b H12C'_b 109.5 ?
C8'_b O13'_b H13'_b 112(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.510(7) y
C1 C8a . 1.520(4) y
C1 H1A . .9700 ?
C1 H1B . .9700 ?
C2 C3 . 1.535(9) y
C2 H2A . .9700 ?
C2 H2B . .9700 ?
C3 C4 . 1.564(6) y
C3 H3A . .9700 ?
C3 H3B . .9700 ?
C4 C4a . 1.510(5) y
C4 H4A . .9700 ?
C4 H4B . .9700 ?
C4a C8a . 1.394(4) y
C4a C5 . 1.402(5) ?
C5 C6 . 1.397(4) ?
C5 C9 . 1.480(5) y
C6 C7 . 1.364(4) ?
C6 H6 . .9300 ?
C7 C8 . 1.393(4) ?
C7 H7 . .9300 ?
C8 O13 . 1.363(3) y
C8 C8a . 1.398(4) ?
C9 O10 . 1.214(6) y
C9 O11 . 1.336(4) y
O11 C12 . 1.442(4) y
C12 H12A . .9600 ?
C12 H12B . .9600 ?
C12 H12C . .9600 ?
O13 H13 . .96(4) ?
C1_b C2_b . 1.50(2) ?
C1_b C8a_b . 1.514(18) ?
C1_b H1A_b . .9700 ?
C1_b H1B_b . .9700 ?
C2_b C3_b . 1.53(2) ?
C2_b H2A_b . .9700 ?
C2_b H2B_b . .9700 ?
C3_b C4_b . 1.56(2) ?
C3_b H3A_b . .9700 ?
C3_b H3B_b . .9700 ?
C4_b C4a_b . 1.512(19) ?
C4_b H4A_b . .9700 ?
C4_b H4B_b . .9700 ?
C4a_b C5_b . 1.395(18) ?
C4a_b C8a_b . 1.413(18) ?
C5_b C6_b . 1.414(19) ?
C5_b C9_b . 1.472(17) ?
C6_b C7_b . 1.363(19) ?
C6_b H6_b . .9300 ?
C7_b C8_b . 1.394(19) ?
C7_b H7_b . .9300 ?
C8_b O13_b . 1.372(18) ?
C8_b C8a_b . 1.396(18) ?
C9_b O10_b . 1.209(19) ?
C9_b O11_b . 1.344(19) ?
O11_b C12_b . 1.45(2) ?
C12_b H12A_b . .9600 ?
C12_b H12B_b . .9600 ?
C12_b H12C_b . .9600 ?
O13_b H13_b . .96(4) ?
C1' C2' . 1.522(5) y
C1' C8a' . 1.516(4) y
C1' H1A' . .9700 ?
C1' H1B' . .9700 ?
C2' C3' . 1.508(7) y
C2' H2A' . .9700 ?
C2' H2B' . .9700 ?
C3' C4' . 1.553(5) y
C3' H3A' . .9700 ?
C3' H3B' . .9700 ?
C4' C4a' . 1.507(5) y
C4' H4A' . .9700 ?
C4' H4B' . .9700 ?
C4a' C8a' . 1.386(4) y
C4a' C5' . 1.435(4) ?
C5' C6' . 1.387(4) ?
C5' C9' . 1.483(4) y
C6' C7' . 1.379(5) ?
C6' H6' . .9300 ?
C7' C8' . 1.387(4) ?
C7' H7' . .9300 ?
C8' O13' . 1.365(3) y
C8' C8a' . 1.394(4) ?
C9' O10' . 1.196(5) y
C9' O11' . 1.341(4) y
O11' C12' . 1.442(4) y
C12' H12A' . .9600 ?
C12' H12B' . .9600 ?
C12' H12C' . .9600 ?
O13' H13' . 1.05(4) ?
C1'_b C8a'_b . 1.511(19) ?
C1'_b C2'_b . 1.53(2) ?
C1'_b H1A'_b . .9700 ?
C1'_b H1B'_b . .9700 ?
C2'_b C3'_b . 1.52(2) ?
C2'_b H2A'_b . .9700 ?
C2'_b H2B'_b . .9700 ?
C3'_b C4'_b . 1.56(2) ?
C3'_b H3A'_b . .9700 ?
C3'_b H3B'_b . .9700 ?
C4'_b C4a'_b . 1.514(19) ?
C4'_b H4A'_b . .9700 ?
C4'_b H4B'_b . .9700 ?
C4a'_b C8a'_b . 1.382(17) ?
C4a'_b C5'_b . 1.429(17) ?
C5'_b C6'_b . 1.386(18) ?
C5'_b C9'_b . 1.465(17) ?
C6'_b C7'_b . 1.377(19) ?
C6'_b H6'_b . .9300 ?
C7'_b C8'_b . 1.375(19) ?
C7'_b H7'_b . .9300 ?
C8'_b O13'_b . 1.369(18) ?
C8'_b C8a'_b . 1.397(18) ?
C9'_b O10'_b . 1.190(18) ?
C9'_b O11'_b . 1.344(18) ?
O11'_b C12'_b . 1.42(2) ?
C12'_b H12A'_b . .9600 ?
C12'_b H12B'_b . .9600 ?
C12'_b H12C'_b . .960(3) ?
O13'_b H13'_b . 1.05(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_publ_flag
C8a C1 C2 C3 -52.0(6) y
C1 C2 C3 C4 70.2(6) y
C2 C3 C4 C4a -53.1(5) y
C3 C4 C4a C8a 18.7(3) y
C3 C4 C4a C5 -161.3(3) ?
C8a C4a C5 C6 0.0 ?
C4 C4a C5 C6 180.0 ?
C8a C4a C5 C9 180.0 ?
C4 C4a C5 C9 0.0 ?
C4a C5 C6 C7 0.0 ?
C9 C5 C6 C7 180.0 ?
C5 C6 C7 C8 0.0 ?
C6 C7 C8 O13 180.0 ?
C6 C7 C8 C8a 0.0 ?
C5 C4a C8a C8 0.0 ?
C4 C4a C8a C8 180.0 ?
C5 C4a C8a C1 180.0 ?
C4 C4a C8a C1 0.0 y
O13 C8 C8a C4a 180.0 ?
C7 C8 C8a C4a 0.0 ?
O13 C8 C8a C1 0.0 ?
C7 C8 C8a C1 180.0 ?
C2 C1 C8a C4a 17.2(4) y
C2 C1 C8a C8 -162.8(4) ?
C6 C5 C9 O10 180.0 ?
C4a C5 C9 O10 0.0 ?
C6 C5 C9 O11 0.0 ?
C4a C5 C9 O11 180.0 ?
O10 C9 O11 C12 0.0 ?
C5 C9 O11 C12 180.0 ?
C8a_b C1_b C2_b C3_b -47(6) ?
C1_b C2_b C3_b C4_b 66(5) ?
C2_b C3_b C4_b C4a_b -51(5) ?
C3_b C4_b C4a_b C5_b -162(3) ?
C3_b C4_b C4a_b C8a_b 18(3) ?
C8a_b C4a_b C5_b C6_b 0.0 ?
C4_b C4a_b C5_b C6_b 180.0 ?
C8a_b C4a_b C5_b C9_b 180.0 ?
C4_b C4a_b C5_b C9_b 0.0 ?
C4a_b C5_b C6_b C7_b 0.0 ?
C9_b C5_b C6_b C7_b 180.0 ?
C5_b C6_b C7_b C8_b 0.0 ?
C6_b C7_b C8_b O13_b 180.0 ?
C6_b C7_b C8_b C8a_b 0.0 ?
O13_b C8_b C8a_b C4a_b 180.0 ?
C7_b C8_b C8a_b C4a_b 0.0 ?
O13_b C8_b C8a_b C1_b 0.0 ?
C7_b C8_b C8a_b C1_b 180.0 ?
C5_b C4a_b C8a_b C8_b 0.0 ?
C4_b C4a_b C8a_b C8_b 180.0 ?
C5_b C4a_b C8a_b C1_b 180.0 ?
C4_b C4a_b C8a_b C1_b 0.0 ?
C2_b C1_b C8a_b C8_b -165(4) ?
C2_b C1_b C8a_b C4a_b 15(4) ?
C4a_b C5_b C9_b O10_b 0.0 ?
C6_b C5_b C9_b O10_b 180.0 ?
C4a_b C5_b C9_b O11_b 180.0 ?
C6_b C5_b C9_b O11_b 0.0 ?
O10_b C9_b O11_b C12_b 0.0 ?
C5_b C9_b O11_b C12_b 180.0 ?
C8a' C1' C2' C3' -52.2(5) y
C1' C2' C3' C4' 69.1(5) y
C2' C3' C4' C4a' -51.0(4) y
C3' C4' C4a' C8a' 16.7(3) y
C3' C4' C4a' C5' -163.3(3) ?
C8a' C4a' C5' C6' 0.0 ?
C4' C4a' C5' C6' 180.0 ?
C8a' C4a' C5' C9' 180.0 ?
C4' C4a' C5' C9' 0.0 ?
C4a' C5' C6' C7' 0.0 ?
C9' C5' C6' C7' 180.0 ?
C5' C6' C7' C8' 0.0 ?
C6' C7' C8' O13' 180.0 ?
C6' C7' C8' C8a' 0.0 ?
C5' C4a' C8a' C8' 0.0 ?
C4' C4a' C8a' C8' 180.0 ?
C5' C4a' C8a' C1' 180.0 ?
C4' C4a' C8a' C1' 0.0 y
O13' C8' C8a' C4a' 180.0 ?
C7' C8' C8a' C4a' 0.0 ?
O13' C8' C8a' C1' 0.0 ?
C7' C8' C8a' C1' 180.0 ?
C2' C1' C8a' C4a' 17.9(3) y
C2' C1' C8a' C8' -162.1(3) ?
C6' C5' C9' O10' 180.0 ?
C4a' C5' C9' O10' 0.0 ?
C6' C5' C9' O11' 0.0 ?
C4a' C5' C9' O11' 180.0 ?
O10' C9' O11' C12' 0.0 ?
C5' C9' O11' C12' 180.0 ?
C8a'_b C1'_b C2'_b C3'_b -48(6) ?
C1'_b C2'_b C3'_b C4'_b 69(5) ?
C2'_b C3'_b C4'_b C4a'_b -55(4) ?
C3'_b C4'_b C4a'_b C8a'_b 21(3) ?
C3'_b C4'_b C4a'_b C5'_b -159(3) ?
C8a'_b C4a'_b C5'_b C6'_b 0.0 ?
C4'_b C4a'_b C5'_b C6'_b 180.0 ?
C8a'_b C4a'_b C5'_b C9'_b 180.0 ?
C4'_b C4a'_b C5'_b C9'_b 0.0 ?
C4a'_b C5'_b C6'_b C7'_b 0.0 ?
C9'_b C5'_b C6'_b C7'_b 180.0 ?
C5'_b C6'_b C7'_b C8'_b 0.0 ?
C6'_b C7'_b C8'_b O13'_b 180.0 ?
C6'_b C7'_b C8'_b C8a'_b 0.0 ?
C5'_b C4a'_b C8a'_b C8'_b 0.0 ?
C4'_b C4a'_b C8a'_b C8'_b 180.0 ?
C5'_b C4a'_b C8a'_b C1'_b 180.0 ?
C4'_b C4a'_b C8a'_b C1'_b 0.0 ?
O13'_b C8'_b C8a'_b C4a'_b 180.0 ?
C7'_b C8'_b C8a'_b C4a'_b 0.0 ?
O13'_b C8'_b C8a'_b C1'_b 0.0 ?
C7'_b C8'_b C8a'_b C1'_b 180.0 ?
C2'_b C1'_b C8a'_b C4a'_b 14(4) ?
C2'_b C1'_b C8a'_b C8'_b -166(4) ?
C6'_b C5'_b C9'_b O10'_b 180.0 ?
C4a'_b C5'_b C9'_b O10'_b 0.0 ?
C6'_b C5'_b C9'_b O11'_b 0.0 ?
C4a'_b C5'_b C9'_b O11'_b 180.0 ?
O10'_b C9'_b O11'_b C12'_b 0.0 ?
C5'_b C9'_b O11'_b C12'_b 180.0 ?
