#------------------------------------------------------------------------------
#$Date: 2022-09-28 18:08:17 +0300 (Wed, 28 Sep 2022) $
#$Revision: 278247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/14/2001471.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_2001471
loop_
_publ_author_name
'Lloyd, B. A.'
'Arif, A. M.'
'Allred, E. L.'
'Sharp, T. R.'
_publ_section_title
;
 A twisted pentacyclic diol derivative
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1534
_journal_page_last               1536
_journal_paper_doi               10.1107/S0108270193001222
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.29
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                85.53(3)
_cell_angle_beta                 99.70(3)
_cell_angle_gamma                117.54(3)
_cell_formula_units_Z            2
_cell_length_a                   6.421(2)
_cell_length_b                   6.658(4)
_cell_length_c                   13.758(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      15
_cell_measurement_theta_min      7.5
_cell_volume                     514.1(4)
_diffrn_measurement_device       'Syntex P-1'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0093
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1773
_diffrn_reflns_theta_max         23
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.0820
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       Prism
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   0.5522
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1256
_refine_ls_R_factor_obs          0.0531
_refine_ls_shift/esd_max         0.002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.0540
_reflns_number_observed          1256
_reflns_number_total             1605
_reflns_observed_criterion       I>3\sI
_cod_data_source_file            hh1010.cif
_cod_data_source_block           hh1010_structure_1_of_1
_cod_original_cell_volume        514.12
_cod_database_code               2001471
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1) .7182(3) .1336(3) .0469(2)
O(2) .9543(4) .8165(3) .0796(2)
C(1) .8189(5) .4428(5) .3316(2)
C(2) .8189(5) .3058(5) .2465(2)
C(3) .9337(5) .4640(5) .1593(2)
C(4) .9048(5) .6790(5) .1663(2)
C(5) .6390(5) .5638(4) .1748(2)
C(6) .5396(5) .3316(4) .1179(2)
C(7) .5431(5) .1809(4) .2068(2)
C(8) .4265(5) .2408(4) .2796(2)
C(9) .4565(6) .1479(5) .3830(2)
C(10) .7255(6) .2845(5) .4188(2)
C(11) .7456(5) .3526(4) .0700(2)
C(12) .6125(5) .4946(4) .2847(2)
C(13) .5682(6) .6527(5) .3429(3)
H1 .972(7) .578(7) .353(3)
H(O1) .849(7) .151(7) .022(3)
H(O2) 1.080(7) .819(7) .060(3)
H2 .896(7) .203(7) .269(3)
H3 1.098(7) .479(7) .152(3)
H4 1.007(7) .775(7) .229(3)
H5 .560(7) .664(7) .149(3)
H6 .375(7) .284(7) .074(3)
H7 .481(7) .024(7) .190(3)
H8 .257(7) .212(7) .251(3)
H9a .410(7) -.009(7) .384(3)
H9b .353(7) .179(7) .428(3)
H10b .816(7) .189(7) .437(3)
H10a .743(7) .373(7) .480(3)
H11 .780(7) .454(7) .006(3)
H13b .707(7) .794(7) .348(3)
H13a .566(7) .609(7) .419(3)
H13c .416(7) .661(7) .316(3)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) C(1) C(10) 109.8(4)
C(2) C(1) C(12) 98.8(3)
C(10) C(1) C(12) 104.7(4)
C(1) C(2) C(3) 111.5(3)
C(1) C(2) C(7) 99.8(3)
C(3) C(2) C(7) 104.8(3)
C(2) C(3) C(4) 106.4(3)
C(2) C(3) C(11) 102.5(3)
C(4) C(3) C(11) 99.3(3)
O(2) C(4) C(3) 112.3(4)
O(2) C(4) C(5) 111.8(4)
C(3) C(4) C(5) 98.1(3)
C(4) C(5) C(6) 103.2(3)
C(4) C(5) C(12) 108.0(3)
C(6) C(5) C(12) 104.9(3)
C(5) C(6) C(7) 98.2(3)
C(5) C(6) C(11) 104.8(3)
C(7) C(6) C(11) 102.7(3)
C(2) C(7) C(6) 98.5(3)
C(2) C(7) C(8) 105.3(3)
C(6) C(7) C(8) 104.2(3)
C(7) C(8) C(9) 113.6(4)
C(7) C(8) C(12) 93.8(3)
C(9) C(8) C(12) 105.4(4)
C(8) C(9) C(10) 103.0(4)
C(1) C(10) C(9) 103.7(4)
O(1) C(11) C(3) 113.3(3)
O(1) C(11) C(6) 111.4(3)
C(3) C(11) C(6) 94.9(3)
C(1) C(12) C(5) 108.9(3)
C(1) C(12) C(8) 93.3(3)
C(1) C(12) C(13) 116.0(4)
C(5) C(12) C(8) 104.2(3)
C(5) C(12) C(13) 114.6(4)
C(8) C(12) C(13) 117.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) H(O1) 0.92(8) no
O(2) H(O2) 0.88(7) no
C(1) H1 0.99(7) no
C(2) H2 1.02(7) no
C(3) H3 1.04(7) no
C(4) H4 1.04(7) no
C(5) H5 1.02(7) no
C(6) H6 1.04(6) no
C(7) H7 0.96(7) no
C(8) H8 1.03(6) no
C(9) H9a 0.94(7) no
C(9) H9b 1.07(7) no
C(10) H10a 1.02(7) no
C(10) H10b 1.04(7) no
C(11) H11 1.06(7) no
C(13) H13b 0.95(7) no
C(13) H13a 1.07(7) no
C(13) H13c 1.01(7) no
O(1) C(11) 1.441(5) yes
O(2) C(4) 1.432(5) yes
C(1) C(2) 1.539(6) yes
C(1) C(10) 1.540(6) yes
C(1) C(12) 1.547(6) yes
C(2) C(3) 1.573(6) yes
C(2) C(7) 1.584(6) yes
C(3) C(4) 1.538(6) yes
C(3) C(11) 1.527(6) yes
C(4) C(5) 1.536(6) yes
C(5) C(6) 1.587(5) yes
C(5) C(12) 1.560(6) yes
C(6) C(7) 1.525(6) yes
C(6) C(11) 1.520(6) yes
C(7) C(8) 1.520(6) yes
C(8) C(9) 1.525(6) yes
C(8) C(12) 1.553(5) yes
C(9) C(10) 1.544(7) yes
C(12) C(13) 1.522(6) yes
