#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/89/2008929.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_2008929
loop_
_publ_author_name
'Jan W. Bats'
'Öhlinger, Stefan H.'
_publ_section_title
;
 Absolute configuration of isocurcumenol
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1595
_journal_page_last               1598
_journal_paper_doi               10.1107/S0108270199006101
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_weight         234.33
_chemical_name_common            isocurcumenol
_chemical_name_systematic
;
3S-(3α,3aα,6α,8aβ)-Octahydro-3-methyl-8-methylene-5-(1-methylethylidene)-
6H-3a,6-epoxyazulen-6-ol
;
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   12.0864(15)
_cell_length_b                   12.0864(15)
_cell_length_c                   7.9291(11)
_cell_measurement_reflns_used    242
_cell_measurement_temperature    135(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     1003.1(2)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1996)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS96 (Sheldrick, 1990)'
_diffrn_ambient_temperature      135(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_sigmaI/netI    0.030
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18520
_diffrn_reflns_theta_full        31.70
_diffrn_reflns_theta_max         31.70
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  540
_diffrn_standards_number         367
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  1.0
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.184
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.038
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.095
_reflns_number_gt                3820
_reflns_number_total             4093
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ka1324.cif
_cod_data_source_block           I_at_135_K
_cod_database_code               2008929
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, 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 0.72077(6) 0.12567(6) 0.69016(8) 0.02080(14) Uani d . 1 . . O
O2 0.63842(7) 0.26046(7) 0.68508(9) 0.02438(15) Uani d . 1 . . O
C1 0.59938(10) -0.09855(9) 0.75963(14) 0.02592(19) Uani d . 1 . . C
C8 0.60599(9) 0.13223(9) 0.67082(12) 0.02037(17) Uani d . 1 . . C
C5 0.68656(9) 0.00017(9) 0.62800(12) 0.02324(18) Uani d . 1 . . C
C9 0.51856(9) 0.05742(10) 0.81820(12) 0.02408(19) Uani d . 1 . . C
C7 0.55368(9) 0.06856(9) 0.50046(12) 0.02261(18) Uani d . 1 . . C
C15 0.37392(11) -0.17742(12) 0.84636(15) 0.0342(2) Uani d . 1 . . C
C6 0.61931(11) -0.00774(10) 0.46163(13) 0.0270(2) Uani d . 1 . . C
C4 0.80721(10) -0.01033(10) 0.62901(15) 0.0294(2) Uani d . 1 . . C
C10 0.48961(10) -0.07987(9) 0.81184(12) 0.02497(19) Uani d . 1 . . C
C11 0.46484(10) 0.07535(11) 0.40879(12) 0.0278(2) Uani d . 1 . . C
C14 0.92359(12) 0.10125(12) 0.54763(19) 0.0360(3) Uani d . 1 . . C
C2 0.69277(11) -0.08517(12) 0.90204(16) 0.0331(2) Uani d . 1 . . C
C3 0.82570(11) -0.02689(11) 0.81835(17) 0.0344(2) Uani d . 1 . . C
C13 0.40021(11) 0.14886(14) 0.46026(16) 0.0372(3) Uani d . 1 . . C
C12 0.42184(12) 0.00993(14) 0.24111(14) 0.0396(3) Uani d . 1 . . C
H6B 0.5594(17) -0.0959(17) 0.430(2) 0.037(4) Uiso d . 1 . . H
H9B 0.5651(14) 0.1032(14) 0.9183(19) 0.023(3) Uiso d . 1 . . H
H13C 0.305(2) 0.0907(19) 0.457(2) 0.049(5) Uiso d . 1 . . H
H02 0.6707(19) 0.2941(18) 0.589(3) 0.042(4) Uiso d . 1 . . H
H2B 0.6951(17) -0.0199(18) 0.994(2) 0.041(4) Uiso d . 1 . . H
H6A 0.6790(14) 0.0303(15) 0.372(2) 0.031(4) Uiso d . 1 . . H
H9A 0.4428(16) 0.0642(15) 0.813(2) 0.034(4) Uiso d . 1 . . H
H13B 0.4262(18) 0.185(2) 0.569(3) 0.047(4) Uiso d . 1 . . H
H14B 0.9093(19) 0.1091(19) 0.431(3) 0.048(5) Uiso d . 1 . . H
H15A 0.3030(16) -0.1616(15) 0.878(2) 0.032(4) Uiso d . 1 . . H
H12C 0.4632(18) -0.0363(16) 0.210(2) 0.037(4) Uiso d . 1 . . H
H1 0.5608(17) -0.1862(17) 0.707(2) 0.042(4) Uiso d . 1 . . H
H12B 0.4283(19) 0.070(2) 0.156(3) 0.049(5) Uiso d . 1 . . H
H14A 1.0000(19) 0.0985(17) 0.558(2) 0.046(5) Uiso d . 1 . . H
H12A 0.334(2) -0.058(2) 0.246(3) 0.069(6) Uiso d . 1 . . H
H4 0.7861(17) -0.0889(16) 0.564(2) 0.036(4) Uiso d . 1 . . H
H3B 0.8661(19) -0.0812(18) 0.833(3) 0.050(5) Uiso d . 1 . . H
H2A 0.6702(17) -0.1613(19) 0.958(2) 0.041(4) Uiso d . 1 . . H
H3A 0.8861(18) 0.0606(18) 0.870(3) 0.043(4) Uiso d . 1 . . H
H13A 0.417(2) 0.213(2) 0.377(3) 0.055(5) Uiso d . 1 . . H
H15B 0.3609(18) -0.260(2) 0.834(3) 0.054(5) Uiso d . 1 . . H
H14C 0.9467(18) 0.1872(19) 0.603(2) 0.046(5) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 O1 C5 104.13(7)
C10 C1 C5 112.47(8)
C10 C1 C2 115.71(10)
C5 C1 C2 103.48(8)
O2 C8 O1 107.99(7)
O2 C8 C7 116.46(8)
O1 C8 C7 103.57(7)
O2 C8 C9 108.70(8)
O1 C8 C9 106.63(7)
C7 C8 C9 112.84(8)
O1 C5 C4 107.57(8)
O1 C5 C6 102.96(7)
C4 C5 C6 120.01(8)
O1 C5 C1 107.96(7)
C4 C5 C1 104.15(8)
C6 C5 C1 113.63(8)
C10 C9 C8 109.54(8)
C11 C7 C6 127.47(10)
C11 C7 C8 126.51(9)
C6 C7 C8 105.97(8)
C7 C6 C5 102.13(8)
C14 C4 C5 114.98(8)
C14 C4 C3 113.40(10)
C5 C4 C3 102.82(9)
C15 C10 C1 122.42(10)
C15 C10 C9 121.87(10)
C1 C10 C9 115.69(8)
C7 C11 C12 121.88(11)
C7 C11 C13 124.13(10)
C12 C11 C13 113.98(11)
C3 C2 C1 105.80(9)
C2 C3 C4 106.96(9)
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 C8 . 1.4368(11) ?
O1 C5 . 1.4448(11) ?
O2 C8 . 1.4003(11) ?
C1 C10 . 1.5106(14) ?
C1 C5 . 1.5382(14) ?
C1 C2 . 1.5468(16) ?
C8 C7 . 1.5264(13) ?
C8 C9 . 1.5311(13) ?
C5 C4 . 1.5257(14) ?
C5 C6 . 1.5272(14) ?
C9 C10 . 1.5159(14) ?
C7 C11 . 1.3327(14) ?
C7 C6 . 1.5186(14) ?
C15 C10 . 1.3310(15) ?
C4 C14 . 1.5220(16) ?
C4 C3 . 1.5455(17) ?
C11 C12 . 1.5007(16) ?
C11 C13 . 1.5033(18) ?
C2 C3 . 1.5447(16) ?
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
_geom_hbond_publ_flag
O2 H02 O2 2_654 0.860(10) 2.10(2) 2.9600(10) 176.0(10) yes
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
C5 O1 C8 O2 -164.52(7)
C5 O1 C8 C7 -40.44(8)
C5 O1 C8 C9 78.82(8)
C8 O1 C5 C4 174.90(8)
C8 O1 C5 C6 47.22(9)
C8 O1 C5 C1 -73.25(9)
C10 C1 C5 O1 50.72(11)
C2 C1 C5 O1 -74.87(9)
C10 C1 C5 C4 164.86(9)
C2 C1 C5 C4 39.28(10)
C10 C1 C5 C6 -62.82(11)
C2 C1 C5 C6 171.60(8)
O2 C8 C9 C10 -176.16(8)
O1 C8 C9 C10 -59.97(9)
C7 C8 C9 C10 53.07(10)
O2 C8 C7 C11 -45.88(13)
O1 C8 C7 C11 -164.24(9)
C9 C8 C7 C11 80.86(12)
O2 C8 C7 C6 136.45(8)
O1 C8 C7 C6 18.09(9)
C9 C8 C7 C6 -96.82(9)
C11 C7 C6 C5 -168.16(10)
C8 C7 C6 C5 9.49(9)
O1 C5 C6 C7 -33.80(9)
C4 C5 C6 C7 -153.20(9)
C1 C5 C6 C7 82.69(9)
O1 C5 C4 C14 -49.11(12)
C6 C5 C4 C14 67.94(13)
C1 C5 C4 C14 -163.53(10)
O1 C5 C4 C3 74.63(9)
C6 C5 C4 C3 -168.33(9)
C1 C5 C4 C3 -39.79(10)
C5 C1 C10 C15 143.94(10)
C2 C1 C10 C15 -97.44(12)
C5 C1 C10 C9 -34.55(12)
C2 C1 C10 C9 84.08(11)
C8 C9 C10 C15 -139.95(10)
C8 C9 C10 C1 38.55(12)
C6 C7 C11 C12 -3.67(16)
C8 C7 C11 C12 179.15(9)
C6 C7 C11 C13 177.15(10)
C8 C7 C11 C13 -0.04(16)
C10 C1 C2 C3 -146.43(9)
C5 C1 C2 C3 -22.96(11)
C1 C2 C3 C4 -1.30(12)
C14 C4 C3 C2 149.97(9)
C5 C4 C3 C2 25.19(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8574577
