#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011949.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_2011949
loop_
_publ_author_name
'Mora, Asilo\'e J.'
'Delgado, Gerzon'
'Delgado, Graciela D\'iaz de'
'Usubillaga, Alfredo'
'Khouri, Nancy'
'Bahsas, Ali'
_publ_section_title
;
 3\a-Hydroxytirucalla-7,24-dien-21-oic acid: a triterpene from
 <i>Protium crenatum</i> Sandwith
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              638
_journal_page_last               640
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C30 H48 O3'
_chemical_formula_sum            'C30 H48 O3'
_chemical_formula_weight         456.68
_chemical_name_systematic
;
3\a-hydroxytirucalla-7,24-diene-21-oic acid
;
_space_group_IT_number           152
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 31 2"'
_symmetry_space_group_name_H-M   'P 31 2 1'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   11.3717(6)
_cell_length_b                   11.3717(6)
_cell_length_c                   36.739(3)
_cell_measurement_reflns_used    3464
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.7
_cell_measurement_theta_min      3.0
_cell_volume                     4114.4(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'PLATON (Spek, 2000) and SHELXL97'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .088
_diffrn_reflns_av_sigmaI/netI    .055
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            22258
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    .069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .3
_refine_diff_density_max         .20
_refine_diff_density_min         -.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .901
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .901
_refine_ls_R_factor_all          .101
_refine_ls_R_factor_gt           .049
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0844P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         .140
_reflns_number_gt                1621
_reflns_number_total             2915
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    da1159.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 31 21'
_cod_original_cell_volume        4114.4(4)
_cod_database_code               2011949
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 .6514(3) .8987(4) .10730(10) .1170(10) Uani d . 1 . . O
O2 .1191(3) .0090(3) .12822(6) .0665(7) Uani d . 1 . . O
O3 -.1017(3) -.0722(3) .13326(6) .0682(8) Uani d . 1 . . O
C1 .4061(4) .7267(5) .14860(10) .0750(10) Uani d . 1 . . C
C2 .5009(5) .8781(5) .15560(10) .089(2) Uani d . 1 . . C
C3 .5726(5) .9507(5) .12100(10) .0790(10) Uani d . 1 . . C
C4 .4740(4) .9379(4) .09090(10) .0670(10) Uani d . 1 . . C
C5 .3720(4) .7848(4) .08495(9) .0570(10) Uani d . 1 . . C
C6 .2703(4) .7586(4) .05450(10) .0800(10) Uani d . 1 . . C
C7 .1735(4) .6115(5) .04890(10) .0750(10) Uani d . 1 . . C
C8 .1573(4) .5128(4) .07231(9) .0560(10) Uani d . 1 . . C
C9 .2395(4) .5477(4) .10661(9) .0590(10) Uani d . 1 . . C
C10 .2998(4) .6963(4) .11885(9) .0580(10) Uani d . 1 . . C
C11 .1717(5) .4400(4) .13608(9) .0680(10) Uani d . 1 . . C
C12 .1100(5) .2928(4) .12471(9) .0660(10) Uani d . 1 . . C
C13 .0957(3) .2698(4) .08331(8) .0511(9) Uani d . 1 . . C
C14 .0501(4) .3658(4) .06645(9) .0550(10) Uani d . 1 . . C
C15 .0194(5) .3142(4) .02720(10) .0770(10) Uani d . 1 . . C
C16 -.0398(4) .1597(4) .02985(9) .0710(10) Uani d . 1 . . C
C17 -.0186(4) .1288(4) .07000(8) .0550(10) Uani d . 1 . . C
C18 .2314(4) .2961(5) .06730(10) .0730(10) Uani d . 1 . . C
C19 .1862(5) .7187(5) .1339(2) .096(2) Uani d . 1 . . C
C20 .0000(4) .0049(4) .07446(9) .0558(9) Uani d . 1 . . C
C21 .0013(4) -.0240(4) .11470(10) .0540(9) Uani d . 1 . . C
C22 -.1113(4) -.1222(4) .0556(9) .0600(10) Uani d . 1 . . C
C23 -.0908(5) -.2444(5) .05810(10) .0810(10) Uani d . 1 . . C
C24 -.1921(5) -.3640(5) .03630(10) .0840(10) Uani d . 1 . . C
C25 -.3025(5) -.4710(5) .04770(10) .0870(10) Uani d . 1 . . C
C26 -.3459(7) -.4949(8) .0861(2) .158(3) Uani d . 1 . . C
C27 -.3944(4) -.5847(4) .02200(10) .138(2) Uani d . 1 . . C
C28 .4098(4) 1.0248(4) .10100(10) .108(2) Uani d R 1 . . C
C29 .5555(5) .9971(5) .05550(10) .098(2) Uani d . 1 . . C
C30 -.0832(4) .3475(5) .08330(10) .0850(10) Uani d . 1 . . C
H1 .7163 .9197 .1208 .175 Uiso calc R 1 . . H
H2 .1110 -.0100 .1499 .100 Uiso calc R 1 . . H
H1A .3595 .6841 .1711 .090 Uiso calc R 1 . . H
H1B .4603 .6861 .1417 .090 Uiso calc R 1 . . H
H2A .4488 .9178 .1650 .106 Uiso calc R 1 . . H
H2B .5677 .8898 .1738 .106 Uiso calc R 1 . . H
H3 .6321 1.0472 .1265 .095 Uiso calc R 1 . . H
H5 .4278 .7479 .0756 .069 Uiso calc R 1 . . H
H6A .2196 .8039 .0603 .096 Uiso calc R 1 . . H
H6B .3193 .7973 .0320 .096 Uiso calc R 1 . . H
H7 .1207 .5857 .0279 .090 Uiso calc R 1 . . H
H9 .3191 .5410 .0997 .071 Uiso calc R 1 . . H
H11A .2387 .4579 .1548 .082 Uiso calc R 1 . . H
H11B .1006 .4516 .1471 .082 Uiso calc R 1 . . H
H12A .0209 .2411 .1357 .079 Uiso calc R 1 . . H
H12B .1660 .2576 .1342 .079 Uiso calc R 1 . . H
H15A .1016 .3555 .0127 .092 Uiso calc R 1 . . H
H15B -.0457 .3350 .0163 .092 Uiso calc R 1 . . H
H16A .0067 .1305 .0132 .085 Uiso calc R 1 . . H
H16B -.1357 .1123 .0238 .085 Uiso calc R 1 . . H
H17 -.1010 .1089 .0834 .066 Uiso calc R 1 . . H
H18A .2566 .2352 .0782 .109 Uiso calc R 1 . . H
H18B .3003 .3881 .0722 .109 Uiso calc R 1 . . H
H18C .2222 .2815 .0415 .109 Uiso calc R 1 . . H
H19A .1196 .6987 .1152 .144 Uiso calc R 1 . . H
H19B .2240 .8115 .1414 .144 Uiso calc R 1 . . H
H19C .1440 .6599 .1543 .144 Uiso calc R 1 . . H
H20 .0879 .0266 .0640 .067 Uiso calc R 1 . . H
H22A -.1982 -.1457 .0664 .072 Uiso calc R 1 . . H
H22B -.1146 -.1016 .0301 .072 Uiso calc R 1 . . H
H23A -.0001 -.2181 .0497 .097 Uiso calc R 1 . . H
H23B -.0973 -.2712 .0834 .097 Uiso calc R 1 . . H
H24 -.1740 -.3616 .0115 .101 Uiso calc R 1 . . H
H26A -.4299 -.5793 .0881 .236 Uiso calc R 1 . . H
H26B -.3585 -.4221 .0946 .236 Uiso calc R 1 . . H
H26C -.2777 -.4989 .1005 .236 Uiso calc R 1 . . H
H27A -.4701 -.6537 .0353 .207 Uiso calc R 1 . . H
H27B -.3443 -.6230 .0111 .207 Uiso calc R 1 . . H
H27C -.4269 -.5492 .0033 .207 Uiso calc R 1 . . H
H28A .3479 1.0175 .0822 .162 Uiso calc R 1 . . H
H28B .4798 1.1179 .1035 .162 Uiso calc R 1 . . H
H28C .3615 .9931 .1236 .162 Uiso calc R 1 . . H
H29A .4952 .9906 .0363 .146 Uiso calc R 1 . . H
H29B .5995 .9469 .0488 .146 Uiso calc R 1 . . H
H29C .6227 1.0906 .0593 .146 Uiso calc R 1 . . H
H30A -.1546 .2553 .0800 .128 Uiso calc R 1 . . H
H30B -.1075 .4075 .0714 .128 Uiso calc R 1 . . H
H30C -.0699 .3684 .1088 .128 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 .065(2) .174(4) .110(3) .058(2) -.017(2) -.020(2)
O2 .060(2) .095(2) .0540(10) .046(2) -.0040(10) .0010(10)
O3 .052(2) .095(2) .0470(10) .029(2) -.0010(10) .0060(10)
C1 .075(3) .081(3) .055(2) .028(3) -.007(2) -.008(2)
C2 .087(3) .088(4) .064(3) .024(3) -.010(3) -.011(3)
C3 .055(3) .085(3) .075(3) .020(3) .001(2) -.013(3)
C4 .048(2) .067(3) .072(3) .019(2) .001(2) .000(2)
C5 .044(2) .062(2) .061(2) .023(2) -.007(2) .001(2)
C6 .061(3) .070(3) .090(3) .017(2) -.022(2) .014(2)
C7 .059(3) .074(3) .066(3) .014(2) -.025(2) .006(2)
C8 .042(2) .063(3) .053(2) .018(2) -.0055(17) .013(2)
C9 .064(2) .063(3) .047(2) .029(2) -.009(2) .007(2)
C10 .046(2) .065(3) .058(2) .026(2) -.002(2) -.004(2)
C11 .081(3) .070(3) .038(2) .026(2) -.002(2) .000(2)
C12 .081(3) .066(3) .043(2) .030(2) -.009(2) .001(2)
C13 .046(2) .066(2) .036(2) .024(2) .001(2) .003(2)
C14 .043(2) .063(3) .045(2) .017(2) -.007(2) .004(2)
C15 .083(3) .074(3) .052(2) .023(3) -.020(2) .008(2)
C16 .072(3) .077(3) .048(2) .025(2) -.014(2) -.002(2)
C17 .050(2) .062(3) .044(2) .022(2) .000(2) .004(2)
C18 .048(3) .077(3) .082(3) .023(2) .002(2) -.005(2)
C19 .071(3) .076(3) .136(4) .034(3) .029(3) .014(3)
C20 .052(2) .072(3) .042(2) .031(2) .003(2) .000(2)
C21 .053(3) .063(3) .052(2) .034(2) -.001(2) -.001(2)
C22 .067(3) .069(3) .042(2) .032(2) -.004(2) -.004(2)
C23 .079(3) .075(3) .088(3) .038(3) .000(3) -.004(3)
C24 .099(4) .075(3) .071(3) .038(3) .003(3) -.013(3)
C25 .088(4) .082(3) .087(3) .038(3) .003(3) .000(3)
C26 .127(5) .173(7) .107(5) .026(5) .044(4) .024(4)
C27 .125(5) .087(4) .178(6) .035(4) -.026(4) -.042(4)
C28 .085(4) .059(3) .167(5) .026(3) .009(3) .006(3)
C29 .066(3) .087(3) .087(3) -.001(3) -.004(3) .012(3)
C30 .052(3) .074(3) .123(4) .026(2) -.005(3) .006(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
O1 C3 . 1.392(6) ?
O2 C21 . 1.296(4) ?
O3 C21 . 1.223(4) ?
C1 C2 . 1.528(6) ?
C1 C10 . 1.536(5) ?
C2 C3 . 1.514(6) ?
C3 C4 . 1.529(6) ?
C4 C28 . 1.539(6) ?
C4 C29 . 1.542(6) ?
C4 C5 . 1.551(5) ?
C5 C6 . 1.529(5) ?
C5 C10 . 1.553(5) ?
C6 C7 . 1.486(6) ?
C7 C8 . 1.353(5) ?
C8 C9 . 1.499(5) ?
C8 C14 . 1.513(5) ?
C9 C11 . 1.523(5) ?
C9 C10 . 1.539(5) ?
C10 C19 . 1.539(6) ?
C11 C12 . 1.515(5) ?
C12 C13 . 1.538(5) ?
C13 C18 . 1.535(5) ?
C13 C14 . 1.552(5) ?
C13 C17 . 1.554(5) ?
C14 C15 . 1.530(5) ?
C14 C30 . 1.551(6) ?
C15 C16 . 1.539(6) ?
C16 C17 . 1.563(4) ?
C17 C20 . 1.535(5) ?
C20 C21 . 1.516(5) ?
C20 C22 . 1.53(2) ?
C22 C23 . 1.522(6) ?
C23 C24 . 1.502(6) ?
C24 C25 . 1.305(6) ?
C25 C26 . 1.474(6) ?
C25 C27 . 1.518(6) ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 '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
C2 C1 C10 113.9(4)
C3 C2 C1 111.0(3)
O1 C3 C2 111.0(4)
O1 C3 C4 107.2(3)
C2 C3 C4 112.7(4)
C3 C4 C28 109.0(3)
C3 C4 C29 108.4(3)
C28 C4 C29 107.4(4)
C3 C4 C5 108.0(3)
C28 C4 C5 115.2(3)
C29 C4 C5 108.7(3)
C6 C5 C4 112.9(3)
C6 C5 C10 111.0(3)
C4 C5 C10 118.1(3)
C7 C6 C5 112.5(3)
C8 C7 C6 124.2(3)
C7 C8 C9 120.5(3)
C7 C8 C14 121.8(3)
C9 C8 C14 117.6(3)
C8 C9 C11 112.8(3)
C8 C9 C10 114.4(3)
C11 C9 C10 116.3(3)
C1 C10 C19 109.8(3)
C1 C10 C9 108.9(3)
C19 C10 C9 109.6(3)
C1 C10 C5 108.9(3)
C19 C10 C5 113.3(4)
C9 C10 C5 106.2(3)
C12 C11 C9 117.4(3)
C11 C12 C13 114.3(3)
C18 C13 C12 109.6(3)
C18 C13 C14 111.5(3)
C12 C13 C14 108.6(3)
C18 C13 C17 108.7(3)
C12 C13 C17 116.7(3)
C14 C13 C17 101.5(3)
C8 C14 C15 117.5(3)
C8 C14 C30 106.5(3)
C15 C14 C30 107.6(3)
C8 C14 C13 110.7(3)
C15 C14 C13 101.5(3)
C30 C14 C13 113.2(3)
C14 C15 C16 105.3(3)
C15 C16 C17 106.7(3)
C20 C17 C13 119.1(3)
C20 C17 C16 114.5(3)
C13 C17 C16 102.1(3)
C21 C20 C22 109(3)
C21 C20 C17 108.9(3)
C22 C20 C17 112.9(3)
O3 C21 O2 122.4(3)
O3 C21 C20 122.0(3)
O2 C21 C20 115.6(3)
C23 C22 C20 114.0(10)
C24 C23 C22 113.4(9)
C25 C24 C23 128.1(4)
C24 C25 C26 123.8(5)
C24 C25 C27 121.7(4)
C26 C25 C27 114.4(5)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O3 1_665 .82 2.08 2.825(4) 151.4
O2 H2 O3 6 .82 1.91 2.666(3) 152.7
_journal_paper_doi 10.1107/S0108270101003316