#------------------------------------------------------------------------------
#$Date: 2017-03-06 13:43:49 +0200 (Mon, 06 Mar 2017) $
#$Revision: 193994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/23/4022393.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022393
loop_
_publ_author_name
'Amaury Patin'
'Alice Kanazawa'
'Christian Philouze'
'Andrew E. Greene'
'Estela Muri'
'Eliezer Barreiro'
'Paulo C. C. Costa'
_publ_section_title
;
 Highly Stereocontrolled Synthesis of Natural Barbacenic Acid,
 Novel Bisnorditerpene from Barbacenia flava
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3831
_journal_page_last               3837
_journal_paper_doi               10.1021/jo0340049
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C21 H36 O4'
_chemical_formula_weight         352.51
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2002-11-14
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                96.27(1)
_cell_angle_beta                 95.08(1)
_cell_angle_gamma                92.77(1)
_cell_formula_units_Z            4
_cell_length_a                   7.3176(7)
_cell_length_b                   12.220(2)
_cell_length_c                   21.946(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      20.9
_cell_measurement_theta_min      20.1
_cell_volume                     1939.7(4)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  CAD-4
_diffrn_measurement_method       ω
_diffrn_orient_matrix_UB_11      0.06436
_diffrn_orient_matrix_UB_12      0.06910
_diffrn_orient_matrix_UB_13      -0.00977
_diffrn_orient_matrix_UB_21      -0.04835
_diffrn_orient_matrix_UB_22      -0.01735
_diffrn_orient_matrix_UB_23      -0.04423
_diffrn_orient_matrix_UB_31      -0.11140
_diffrn_orient_matrix_UB_32      0.04154
_diffrn_orient_matrix_UB_33      0.00821
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.02935
_diffrn_reflns_av_sigmaI/netI    0.080
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5018
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        54.96
_diffrn_reflns_theta_max         54.96
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        12.67
_diffrn_standards_interval_count 0
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776.00
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.918
_refine_ls_goodness_of_fit_ref   1.918
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     451
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.0029
_refine_ls_shift/su_mean         0.0004
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00194|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.1114
_refine_ls_wR_factor_ref         0.1114
_reflns_number_gt                2948
_reflns_number_total             4866
_reflns_threshold_expression     I>2.00σ(I)
_cod_data_source_file            jo0340049si20030213_095327_2.cif
_cod_data_source_block           C21O4H36
_cod_depositor_comments
;
 Adding the '_geom_hbond_atom_site_label_A' data item. Values of the
 data item were determined from the geometry of the molecule.

 Antanas Vaitkus,
 2017-03-06

The following automatic conversions were performed:
data name '_geom_bond_atom_site_label_D' replaced with
'_geom_hbond_atom_site_label_D' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_atom_site_label_H' replaced with
'_geom_hbond_atom_site_label_H' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_distance_DH' replaced with '_geom_hbond_distance_DH'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_HA' replaced with
'_geom_hbond_distance_HA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_DA' replaced with
'_geom_hbond_distance_DA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_angle_DHA' replaced with '_geom_hbond_angle_DHA' as
specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_site_symmetry_A' replaced with
'_geom_hbond_site_symmetry_A' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_original_sg_symbol_H-M      'P -1       '
_cod_original_formula_sum        'C21 H36 O4 '
_cod_database_code               4022393
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   -y,   -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_calc_flag
O(1) 0.7630(6) 0.0093(3) 0.5443(2) 0.054(1) 1.000 Uani d
O(2) 0.5834(6) 0.1808(3) 0.5286(2) 0.066(1) 1.000 Uani d
O(3) 1.0478(6) 0.0331(3) 0.9205(2) 0.056(1) 1.000 Uani d
O(4) 1.1613(5) 0.1957(3) 0.8875(2) 0.048(1) 1.000 Uani d
O(5) 1.4309(6) -0.3641(3) 0.5451(2) 0.061(1) 1.000 Uani d
O(6) 1.7284(6) -0.2164(3) 0.5547(2) 0.061(1) 1.000 Uani d
O(7) 1.1161(6) -0.3404(4) 0.8977(2) 0.073(2) 1.000 Uani d
O(8) 1.4173(6) -0.3948(3) 0.9001(2) 0.056(1) 1.000 Uani d
C(1) 0.9919(7) 0.1029(4) 0.6247(2) 0.039(2) 1.000 Uani d
C(1') 1.0787(8) -0.0085(5) 0.6232(2) 0.048(2) 1.000 Uani d
C(2) 0.7861(8) 0.0870(4) 0.5987(2) 0.041(2) 1.000 Uani d
C(3) 0.6552(7) 0.0505(5) 0.6441(2) 0.045(2) 1.000 Uani d
C(4) 0.6912(7) 0.1156(5) 0.7077(2) 0.041(2) 1.000 Uani d
C(5) 0.8891(7) 0.1134(4) 0.7333(2) 0.034(1) 1.000 Uani d
C(6') 0.8441(8) 0.2617(4) 0.8234(2) 0.044(2) 1.000 Uani d
C(6) 0.9191(7) 0.1500(4) 0.8048(2) 0.036(1) 1.000 Uani d
C(7) 1.1251(8) 0.1501(4) 0.8245(2) 0.043(2) 1.000 Uani d
C(8) 1.2485(7) 0.2134(5) 0.7877(3) 0.051(2) 1.000 Uani d
C(9) 1.2158(8) 0.1669(5) 0.7194(2) 0.050(2) 1.000 Uani d
C(10') 0.9817(8) 0.2940(5) 0.6905(2) 0.045(2) 1.000 Uani d
C(10) 1.0165(7) 0.1714(4) 0.6922(2) 0.037(2) 1.000 Uani d
C(11) 1.0717(8) 0.1693(5) 0.5756(2) 0.051(2) 1.000 Uani d
C(12) 0.9137(9) 0.2301(5) 0.5445(3) 0.060(2) 1.000 Uani d
C(13) 0.7413(8) 0.1947(5) 0.5726(2) 0.049(2) 1.000 Uani d
C(14) 0.8191(8) 0.0613(5) 0.8366(2) 0.051(2) 1.000 Uani d
C(15) 0.8652(9) 0.0644(5) 0.9066(3) 0.060(2) 1.000 Uani d
C(16) 1.1864(9) 0.1213(5) 0.9320(2) 0.051(2) 1.000 Uani d
C(17) 1.173(1) 0.1881(6) 0.9936(3) 0.071(2) 1.000 Uani d
C(18) 1.364(1) 0.0664(6) 0.9298(3) 0.079(2) 1.000 Uani d
C(19) 1.5293(8) -0.4338(4) 0.6412(3) 0.046(2) 1.000 Uani d
C(19') 1.358(1) -0.5106(5) 0.6246(3) 0.073(2) 1.000 Uani d
C(20) 1.5131(8) -0.3294(5) 0.6070(2) 0.045(2) 1.000 Uani d
C(21) 1.3998(8) -0.2426(5) 0.6366(3) 0.053(2) 1.000 Uani d
C(22) 1.4437(9) -0.2172(5) 0.7049(3) 0.053(2) 1.000 Uani d
C(23) 1.4325(7) -0.3224(4) 0.7364(2) 0.039(2) 1.000 Uani d
C(24) 1.4216(8) -0.3003(4) 0.8081(2) 0.043(2) 1.000 Uani d
C(24') 1.585(1) -0.2269(5) 0.8422(3) 0.068(2) 1.000 Uani d
C(25) 1.4081(8) -0.4114(5) 0.8340(2) 0.049(2) 1.000 Uani d
C(26) 1.5546(9) -0.4883(5) 0.8160(3) 0.061(2) 1.000 Uani d
C(27) 1.5463(9) -0.5099(5) 0.7460(3) 0.061(2) 1.000 Uani d
C(28) 1.5742(8) -0.4046(4) 0.7142(2) 0.043(2) 1.000 Uani d
C(28') 1.7732(8) -0.3594(6) 0.7322(3) 0.062(2) 1.000 Uani d
C(29) 1.691(1) -0.4888(5) 0.6109(3) 0.062(2) 1.000 Uani d
C(30) 1.8054(9) -0.3994(6) 0.5856(3) 0.069(2) 1.000 Uani d
C(31) 1.7111(8) -0.2916(5) 0.5997(2) 0.049(2) 1.000 Uani d
C(32) 1.246(1) -0.2396(5) 0.8202(3) 0.063(2) 1.000 Uani d
C(33) 1.181(1) -0.2359(5) 0.8842(3) 0.071(2) 1.000 Uani d
C(34) 1.249(1) -0.4032(5) 0.9267(3) 0.062(2) 1.000 Uani d
C(35) 1.297(1) -0.3609(6) 0.9943(3) 0.087(3) 1.000 Uani d
C(36) 1.165(1) -0.5193(6) 0.9192(4) 0.102(3) 1.000 Uani d
H(1) 0.7600 -0.0595 0.5573 0.074 1.000 Uiso c
H(2) 0.5758 0.1054 0.5185 0.157 1.000 Uiso c
H(3) 1.0324 -0.0488 0.6538 0.057 1.000 Uiso c
H(4) 1.2084 0.0029 0.6312 0.057 1.000 Uiso c
H(5) 1.0494 -0.0490 0.5838 0.057 1.000 Uiso c
H(6) 0.5328 0.0602 0.6283 0.053 1.000 Uiso c
H(7) 0.6694 -0.0254 0.6481 0.053 1.000 Uiso c
H(8) 0.6627 0.1899 0.7048 0.049 1.000 Uiso c
H(9) 0.6146 0.0844 0.7349 0.049 1.000 Uiso c
H(10) 0.9165 0.0379 0.7283 0.040 1.000 Uiso c
H(11) 0.8632 0.2786 0.8668 0.053 1.000 Uiso c
H(12) 0.7163 0.2592 0.8107 0.053 1.000 Uiso c
H(13) 0.9061 0.3168 0.8042 0.053 1.000 Uiso c
H(14) 1.1590 0.0758 0.8213 0.052 1.000 Uiso c
H(15) 1.3732 0.2065 0.8021 0.061 1.000 Uiso c
H(16) 1.2219 0.2891 0.7922 0.061 1.000 Uiso c
H(17) 1.2475 0.0922 0.7155 0.060 1.000 Uiso c
H(18) 1.2929 0.2085 0.6967 0.060 1.000 Uiso c
H(19) 1.0017 0.3313 0.7311 0.054 1.000 Uiso c
H(20) 0.8585 0.3011 0.6745 0.054 1.000 Uiso c
H(21) 1.0635 0.3254 0.6650 0.054 1.000 Uiso c
H(22) 1.1654 0.2214 0.5948 0.061 1.000 Uiso c
H(23) 1.1215 0.1204 0.5455 0.061 1.000 Uiso c
H(24) 0.9375 0.3077 0.5526 0.072 1.000 Uiso c
H(25) 0.9008 0.2094 0.5012 0.072 1.000 Uiso c
H(26) 0.7197 0.2486 0.6053 0.059 1.000 Uiso c
H(27) 0.6908 0.0692 0.8293 0.061 1.000 Uiso c
H(28) 0.8485 -0.0088 0.8181 0.061 1.000 Uiso c
H(29) 0.8538 0.1371 0.9256 0.072 1.000 Uiso c
H(30) 0.7817 0.0149 0.9222 0.072 1.000 Uiso c
H(31) 1.0543 0.2152 0.9948 0.086 1.000 Uiso c
H(32) 1.2628 0.2482 0.9989 0.086 1.000 Uiso c
H(33) 1.1953 0.1426 1.0256 0.086 1.000 Uiso c
H(34) 1.4637 0.1205 0.9380 0.095 1.000 Uiso c
H(35) 1.3694 0.0275 0.8902 0.095 1.000 Uiso c
H(36) 1.3731 0.0161 0.9600 0.095 1.000 Uiso c
H(37) 1.4301 -0.2970 0.5292 0.149 1.000 Uiso c
H(38) 1.6701 -0.2548 0.5226 0.073 1.000 Uiso c
H(39) 1.3675 -0.5729 0.6468 0.087 1.000 Uiso c
H(40) 1.2527 -0.4726 0.6349 0.087 1.000 Uiso c
H(41) 1.3466 -0.5343 0.5817 0.087 1.000 Uiso c
H(42) 1.2740 -0.2673 0.6287 0.063 1.000 Uiso c
H(43) 1.4200 -0.1767 0.6183 0.063 1.000 Uiso c
H(44) 1.3582 -0.1680 0.7207 0.064 1.000 Uiso c
H(45) 1.5645 -0.1837 0.7132 0.064 1.000 Uiso c
H(46) 1.3164 -0.3575 0.7209 0.047 1.000 Uiso c
H(47) 1.5678 -0.2143 0.8847 0.082 1.000 Uiso c
H(48) 1.5914 -0.1583 0.8256 0.082 1.000 Uiso c
H(49) 1.6958 -0.2627 0.8372 0.082 1.000 Uiso c
H(50) 1.2918 -0.4469 0.8191 0.058 1.000 Uiso c
H(51) 1.5347 -0.5561 0.8326 0.074 1.000 Uiso c
H(52) 1.6720 -0.4556 0.8318 0.074 1.000 Uiso c
H(53) 1.4294 -0.5444 0.7310 0.073 1.000 Uiso c
H(54) 1.6396 -0.5581 0.7356 0.073 1.000 Uiso c
H(55) 1.7941 -0.3452 0.7757 0.074 1.000 Uiso c
H(56) 1.7938 -0.2929 0.7144 0.074 1.000 Uiso c
H(57) 1.8550 -0.4121 0.7175 0.074 1.000 Uiso c
H(58) 1.7652 -0.5219 0.6408 0.075 1.000 Uiso c
H(59) 1.6448 -0.5434 0.5784 0.075 1.000 Uiso c
H(60) 1.9272 -0.3935 0.6052 0.083 1.000 Uiso c
H(61) 1.8086 -0.4162 0.5425 0.083 1.000 Uiso c
H(62) 1.7646 -0.2563 0.6383 0.059 1.000 Uiso c
H(63) 1.1495 -0.2744 0.7919 0.076 1.000 Uiso c
H(64) 1.2677 -0.1656 0.8120 0.076 1.000 Uiso c
H(65) 1.0845 -0.1869 0.8870 0.085 1.000 Uiso c
H(66) 1.2809 -0.2094 0.9137 0.085 1.000 Uiso c
H(67) 1.1886 -0.3628 1.0153 0.104 1.000 Uiso c
H(68) 1.3475 -0.2872 0.9978 0.104 1.000 Uiso c
H(69) 1.3837 -0.4062 1.0121 0.104 1.000 Uiso c
H(70) 1.0521 -0.5206 0.9372 0.122 1.000 Uiso c
H(71) 1.1445 -0.5453 0.8766 0.122 1.000 Uiso c
H(72) 1.2472 -0.5653 0.9390 0.122 1.000 Uiso c
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 84 0.017 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O 0 16 0.047 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H 0 144 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 0 -3
-2 4 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
C(2) O(1) H(1) 106.6 no
C(13) O(2) H(2) 101.1 no
C(15) O(3) C(16) 115.8(5) yes
C(7) O(4) C(16) 117.5(4) yes
C(20) O(5) H(37) 100.3 no
C(31) O(6) H(38) 100.3 no
C(33) O(7) C(34) 115.6(5) yes
C(25) O(8) C(34) 116.7(5) yes
C(1') C(1) C(2) 110.3(4) yes
C(1') C(1) C(10) 112.6(4) yes
C(1') C(1) C(11) 109.2(4) yes
C(2) C(1) C(10) 111.7(4) yes
C(2) C(1) C(11) 100.6(4) yes
C(10) C(1) C(11) 111.9(4) yes
C(1) C(1') H(3) 109.5 no
C(1) C(1') H(4) 109.5 no
C(1) C(1') H(5) 109.5 no
H(3) C(1') H(4) 109.5 no
H(3) C(1') H(5) 109.5 no
H(4) C(1') H(5) 109.5 no
O(1) C(2) C(1) 110.9(4) yes
O(1) C(2) C(3) 108.4(4) yes
O(1) C(2) C(13) 101.7(4) yes
C(1) C(2) C(3) 114.7(4) yes
C(1) C(2) C(13) 105.4(4) yes
C(3) C(2) C(13) 114.8(5) yes
C(2) C(3) C(4) 112.8(4) yes
C(2) C(3) H(6) 108.6 no
C(2) C(3) H(7) 108.6 no
C(4) C(3) H(6) 108.6 no
C(4) C(3) H(7) 108.6 no
H(6) C(3) H(7) 109.5 no
C(3) C(4) C(5) 111.8(4) yes
C(3) C(4) H(8) 108.9 no
C(3) C(4) H(9) 108.9 no
C(5) C(4) H(8) 108.9 no
C(5) C(4) H(9) 108.9 no
H(8) C(4) H(9) 109.5 no
C(4) C(5) C(6) 112.8(4) yes
C(4) C(5) C(10) 109.9(4) yes
C(4) C(5) H(10) 105.3 no
C(6) C(5) C(10) 117.0(4) yes
C(6) C(5) H(10) 105.3 no
C(10) C(5) H(10) 105.3 no
C(6) C(6') H(11) 109.5 no
C(6) C(6') H(12) 109.5 no
C(6) C(6') H(13) 109.5 no
H(11) C(6') H(12) 109.5 no
H(11) C(6') H(13) 109.5 no
H(12) C(6') H(13) 109.5 no
C(5) C(6) C(6') 113.1(4) yes
C(5) C(6) C(7) 107.8(4) yes
C(5) C(6) C(14) 107.2(4) yes
C(6') C(6) C(7) 111.3(4) yes
C(6') C(6) C(14) 109.1(4) yes
C(7) C(6) C(14) 108.2(4) yes
O(4) C(7) C(6) 109.6(4) yes
O(4) C(7) C(8) 107.3(4) yes
O(4) C(7) H(14) 108.0 no
C(6) C(7) C(8) 115.6(5) yes
C(6) C(7) H(14) 108.0 no
C(8) C(7) H(14) 108.0 no
C(7) C(8) C(9) 109.4(5) yes
C(7) C(8) H(15) 109.5 no
C(7) C(8) H(16) 109.5 no
C(9) C(8) H(15) 109.5 no
C(9) C(8) H(16) 109.5 no
H(15) C(8) H(16) 109.5 no
C(8) C(9) C(10) 113.6(5) yes
C(8) C(9) H(17) 108.4 no
C(8) C(9) H(18) 108.4 no
C(10) C(9) H(17) 108.4 no
C(10) C(9) H(18) 108.4 no
H(17) C(9) H(18) 109.5 no
C(10) C(10') H(19) 109.5 no
C(10) C(10') H(20) 109.5 no
C(10) C(10') H(21) 109.5 no
H(19) C(10') H(20) 109.5 no
H(19) C(10') H(21) 109.5 no
H(20) C(10') H(21) 109.5 no
C(1) C(10) C(5) 107.7(4) yes
C(1) C(10) C(9) 108.9(4) yes
C(1) C(10) C(10') 112.5(4) yes
C(5) C(10) C(9) 108.3(4) yes
C(5) C(10) C(10') 113.0(4) yes
C(9) C(10) C(10') 106.3(4) yes
C(1) C(11) C(12) 108.4(5) yes
C(1) C(11) H(22) 109.7 no
C(1) C(11) H(23) 109.7 no
C(12) C(11) H(22) 109.7 no
C(12) C(11) H(23) 109.7 no
H(22) C(11) H(23) 109.5 no
C(11) C(12) C(13) 105.8(5) yes
C(11) C(12) H(24) 110.4 no
C(11) C(12) H(25) 110.4 no
C(13) C(12) H(24) 110.4 no
C(13) C(12) H(25) 110.4 no
H(24) C(12) H(25) 109.5 no
O(2) C(13) C(2) 112.0(4) yes
O(2) C(13) C(12) 112.3(5) yes
O(2) C(13) H(26) 109.2 no
C(2) C(13) C(12) 104.9(5) yes
C(2) C(13) H(26) 109.2 no
C(12) C(13) H(26) 109.2 no
C(6) C(14) C(15) 116.6(5) yes
C(6) C(14) H(27) 107.7 no
C(6) C(14) H(28) 107.7 no
C(15) C(14) H(27) 107.7 no
C(15) C(14) H(28) 107.7 no
H(27) C(14) H(28) 109.5 no
O(3) C(15) C(14) 110.8(5) yes
O(3) C(15) H(29) 109.1 no
O(3) C(15) H(30) 109.1 no
C(14) C(15) H(29) 109.1 no
C(14) C(15) H(30) 109.1 no
H(29) C(15) H(30) 109.5 no
O(3) C(16) O(4) 110.1(4) yes
O(3) C(16) C(17) 111.4(5) yes
O(3) C(16) C(18) 104.9(5) yes
O(4) C(16) C(17) 105.8(5) yes
O(4) C(16) C(18) 112.9(5) yes
C(17) C(16) C(18) 111.9(5) yes
C(16) C(17) H(31) 109.5 no
C(16) C(17) H(32) 109.5 no
C(16) C(17) H(33) 109.5 no
H(31) C(17) H(32) 109.5 no
H(31) C(17) H(33) 109.5 no
H(32) C(17) H(33) 109.5 no
C(16) C(18) H(34) 109.5 no
C(16) C(18) H(35) 109.5 no
C(16) C(18) H(36) 109.5 no
H(34) C(18) H(35) 109.5 no
H(34) C(18) H(36) 109.5 no
H(35) C(18) H(36) 109.5 no
C(19') C(19) C(20) 110.2(5) yes
C(19') C(19) C(28) 112.4(5) yes
C(19') C(19) C(29) 108.0(5) yes
C(20) C(19) C(28) 112.7(4) yes
C(20) C(19) C(29) 101.1(4) yes
C(28) C(19) C(29) 111.9(5) yes
C(19) C(19') H(39) 109.5 no
C(19) C(19') H(40) 109.5 no
C(19) C(19') H(41) 109.5 no
H(39) C(19') H(40) 109.5 no
H(39) C(19') H(41) 109.5 no
H(40) C(19') H(41) 109.5 no
O(5) C(20) C(19) 107.8(4) yes
O(5) C(20) C(21) 108.7(5) yes
O(5) C(20) C(31) 105.3(4) yes
C(19) C(20) C(21) 114.5(5) yes
C(19) C(20) C(31) 104.8(5) yes
C(21) C(20) C(31) 115.2(5) yes
C(20) C(21) C(22) 114.3(5) yes
C(20) C(21) H(42) 108.3 no
C(20) C(21) H(43) 108.3 no
C(22) C(21) H(42) 108.3 no
C(22) C(21) H(43) 108.3 no
H(42) C(21) H(43) 109.5 no
C(21) C(22) C(23) 110.8(5) yes
C(21) C(22) H(44) 109.2 no
C(21) C(22) H(45) 109.2 no
C(23) C(22) H(44) 109.1 no
C(23) C(22) H(45) 109.1 no
H(44) C(22) H(45) 109.5 no
C(22) C(23) C(24) 113.5(4) yes
C(22) C(23) C(28) 111.5(4) yes
C(22) C(23) H(46) 104.5 no
C(24) C(23) C(28) 116.8(4) yes
C(24) C(23) H(46) 104.5 no
C(28) C(23) H(46) 104.5 no
C(23) C(24) C(24') 113.6(5) yes
C(23) C(24) C(25) 108.5(4) yes
C(23) C(24) C(32) 108.8(5) yes
C(24') C(24) C(25) 110.5(5) yes
C(24') C(24) C(32) 106.7(5) yes
C(25) C(24) C(32) 108.5(5) yes
C(24) C(24') H(47) 109.5 no
C(24) C(24') H(48) 109.5 no
C(24) C(24') H(49) 109.5 no
H(47) C(24') H(48) 109.5 no
H(47) C(24') H(49) 109.5 no
H(48) C(24') H(49) 109.5 no
O(8) C(25) C(24) 110.2(4) yes
O(8) C(25) C(26) 108.2(5) yes
O(8) C(25) H(50) 108.0 no
C(24) C(25) C(26) 114.4(5) yes
C(24) C(25) H(50) 108.0 no
C(26) C(25) H(50) 108.0 no
C(25) C(26) C(27) 109.6(5) yes
C(25) C(26) H(51) 109.4 no
C(25) C(26) H(52) 109.4 no
C(27) C(26) H(51) 109.4 no
C(27) C(26) H(52) 109.4 no
H(51) C(26) H(52) 109.5 no
C(26) C(27) C(28) 113.7(5) yes
C(26) C(27) H(53) 108.4 no
C(26) C(27) H(54) 108.4 no
C(28) C(27) H(53) 108.4 no
C(28) C(27) H(54) 108.4 no
H(53) C(27) H(54) 109.5 no
C(19) C(28) C(23) 107.3(4) yes
C(19) C(28) C(27) 109.4(4) yes
C(19) C(28) C(28') 112.6(5) yes
C(23) C(28) C(27) 107.7(5) yes
C(23) C(28) C(28') 112.4(5) yes
C(27) C(28) C(28') 107.3(5) yes
C(28) C(28') H(55) 109.5 no
C(28) C(28') H(56) 109.5 no
C(28) C(28') H(57) 109.5 no
H(55) C(28') H(56) 109.5 no
H(55) C(28') H(57) 109.5 no
H(56) C(28') H(57) 109.5 no
C(19) C(29) C(30) 108.1(5) yes
C(19) C(29) H(58) 109.8 no
C(19) C(29) H(59) 109.8 no
C(30) C(29) H(58) 109.8 no
C(30) C(29) H(59) 109.8 no
H(58) C(29) H(59) 109.5 no
C(29) C(30) C(31) 106.5(5) yes
C(29) C(30) H(60) 110.2 no
C(29) C(30) H(61) 110.2 no
C(31) C(30) H(60) 110.2 no
C(31) C(30) H(61) 110.2 no
H(60) C(30) H(61) 109.5 no
O(6) C(31) C(20) 114.1(5) yes
O(6) C(31) C(30) 114.0(5) yes
O(6) C(31) H(62) 108.2 no
C(20) C(31) C(30) 103.8(5) yes
C(20) C(31) H(62) 108.2 no
C(30) C(31) H(62) 108.2 no
C(24) C(32) C(33) 117.8(5) yes
C(24) C(32) H(63) 107.4 no
C(24) C(32) H(64) 107.4 no
C(33) C(32) H(63) 107.3 no
C(33) C(32) H(64) 107.4 no
H(63) C(32) H(64) 109.5 no
O(7) C(33) C(32) 112.5(5) yes
O(7) C(33) H(65) 108.7 no
O(7) C(33) H(66) 108.7 no
C(32) C(33) H(65) 108.7 no
C(32) C(33) H(66) 108.7 no
H(65) C(33) H(66) 109.5 no
O(7) C(34) O(8) 110.8(5) yes
O(7) C(34) C(35) 112.3(6) yes
O(7) C(34) C(36) 105.5(6) yes
O(8) C(34) C(35) 104.5(5) yes
O(8) C(34) C(36) 112.6(6) yes
C(35) C(34) C(36) 111.2(6) yes
C(34) C(35) H(67) 109.5 no
C(34) C(35) H(68) 109.5 no
C(34) C(35) H(69) 109.5 no
H(67) C(35) H(68) 109.5 no
H(67) C(35) H(69) 109.5 no
H(68) C(35) H(69) 109.5 no
C(34) C(36) H(70) 109.5 no
C(34) C(36) H(71) 109.5 no
C(34) C(36) H(72) 109.5 no
H(70) C(36) H(71) 109.5 no
H(70) C(36) H(72) 109.5 no
H(71) C(36) H(72) 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(2) 1.433(6) yes
O(1) H(1) 0.92 no
O(2) C(13) 1.429(7) yes
O(2) H(2) 0.92 no
O(3) C(15) 1.424(7) yes
O(3) C(16) 1.430(7) yes
O(4) C(7) 1.430(6) yes
O(4) C(16) 1.412(7) yes
O(5) C(20) 1.446(6) yes
O(5) H(37) 0.93 no
O(6) C(31) 1.430(7) yes
O(6) H(38) 0.87 no
O(7) C(33) 1.411(8) yes
O(7) C(34) 1.416(8) yes
O(8) C(25) 1.439(6) yes
O(8) C(34) 1.414(7) yes
C(1) C(1') 1.529(8) yes
C(1) C(2) 1.558(7) yes
C(1) C(10) 1.611(7) yes
C(1) C(11) 1.555(7) yes
C(1') H(3) 0.95 no
C(1') H(4) 0.95 no
C(1') H(5) 0.95 no
C(2) C(3) 1.528(7) yes
C(2) C(13) 1.531(8) yes
C(3) C(4) 1.524(7) yes
C(3) H(6) 0.95 no
C(3) H(7) 0.95 no
C(4) C(5) 1.508(7) yes
C(4) H(8) 0.95 no
C(4) H(9) 0.95 no
C(5) C(6) 1.577(7) yes
C(5) C(10) 1.553(7) yes
C(5) H(10) 0.95 no
C(6') C(6) 1.523(7) yes
C(6') H(11) 0.95 no
C(6') H(12) 0.95 no
C(6') H(13) 0.95 no
C(6) C(7) 1.531(7) yes
C(6) C(14) 1.542(7) yes
C(7) C(8) 1.505(8) yes
C(7) H(14) 0.95 no
C(8) C(9) 1.536(8) yes
C(8) H(15) 0.95 no
C(8) H(16) 0.95 no
C(9) C(10) 1.532(8) yes
C(9) H(17) 0.95 no
C(9) H(18) 0.95 no
C(10') C(10) 1.535(7) yes
C(10') H(19) 0.95 no
C(10') H(20) 0.95 no
C(10') H(21) 0.95 no
C(11) C(12) 1.552(9) yes
C(11) H(22) 0.95 no
C(11) H(23) 0.95 no
C(12) C(13) 1.518(9) yes
C(12) H(24) 0.95 no
C(12) H(25) 0.95 no
C(13) H(26) 0.95 no
C(14) C(15) 1.539(8) yes
C(14) H(27) 0.95 no
C(14) H(28) 0.95 no
C(15) H(29) 0.95 no
C(15) H(30) 0.95 no
C(16) C(17) 1.512(8) yes
C(16) C(18) 1.496(9) yes
C(17) H(31) 0.95 no
C(17) H(32) 0.95 no
C(17) H(33) 0.95 no
C(18) H(34) 0.95 no
C(18) H(35) 0.95 no
C(18) H(36) 0.95 no
C(19) C(19') 1.522(8) yes
C(19) C(20) 1.553(8) yes
C(19) C(28) 1.603(7) yes
C(19) C(29) 1.555(9) yes
C(19') H(39) 0.95 no
C(19') H(40) 0.95 no
C(19') H(41) 0.95 no
C(20) C(21) 1.505(8) yes
C(20) C(31) 1.527(8) yes
C(21) C(22) 1.500(8) yes
C(21) H(42) 0.95 no
C(21) H(43) 0.95 no
C(22) C(23) 1.527(8) yes
C(22) H(44) 0.95 no
C(22) H(45) 0.95 no
C(23) C(24) 1.576(7) yes
C(23) C(28) 1.551(8) yes
C(23) H(46) 0.95 no
C(24) C(24') 1.544(8) yes
C(24) C(25) 1.531(8) yes
C(24) C(32) 1.542(9) yes
C(24') H(47) 0.95 no
C(24') H(48) 0.95 no
C(24') H(49) 0.95 no
C(25) C(26) 1.510(8) yes
C(25) H(50) 0.95 no
C(26) C(27) 1.526(8) yes
C(26) H(51) 0.95 no
C(26) H(52) 0.95 no
C(27) C(28) 1.544(8) yes
C(27) H(53) 0.95 no
C(27) H(54) 0.95 no
C(28) C(28') 1.534(8) yes
C(28') H(55) 0.95 no
C(28') H(56) 0.95 no
C(28') H(57) 0.95 no
C(29) C(30) 1.524(9) yes
C(29) H(58) 0.95 no
C(29) H(59) 0.95 no
C(30) C(31) 1.531(9) yes
C(30) H(60) 0.95 no
C(30) H(61) 0.95 no
C(31) H(62) 0.95 no
C(32) C(33) 1.521(9) yes
C(32) H(63) 0.95 no
C(32) H(64) 0.95 no
C(33) H(65) 0.95 no
C(33) H(66) 0.95 no
C(34) C(35) 1.521(9) yes
C(34) C(36) 1.503(9) yes
C(35) H(67) 0.95 no
C(35) H(68) 0.95 no
C(35) H(69) 0.95 no
C(36) H(70) 0.95 no
C(36) H(71) 0.95 no
C(36) H(72) 0.95 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O(1) O(6) 2.793(5) 1_455 no
O(1) O(2) 3.505(5) 2_656 no
O(1) C(11) 3.566(7) 2_756 no
O(2) O(6) 2.875(5) 2_756 no
O(2) O(5) 2.902(6) 2_756 no
O(3) C(33) 3.502(8) . no
O(4) C(36) 3.475(9) 1_565 no
O(6) C(11) 3.415(7) 2_856 no
O(6) C(12) 3.549(8) 2_856 no
C(4) C(9) 3.592(8) 1_455 no
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
O(1) H(1) O(6) 0.92 1.91 2.793(5) 160.0 1_455
O(2) H(2) O(1) 0.92 1.93 2.566(6) 124.0 .
O(5) H(37) O(2) 0.93 2.00 2.902(6) 163.2 2_756
O(6) H(38) O(5) 0.87 2.27 2.738(6) 113.7 .
O(6) H(38) O(2) 0.87 2.35 2.875(5) 118.9 2_756
