#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/16/4101660.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_4101660
loop_
_publ_author_name
'Gao, Shuanhu'
'Wang, Qiaoling'
'Huang, Lily Jun-Shen'
'Lum, Lawrence'
'Chen, Chuo'
_publ_section_title
;
 Chemical and biological studies of nakiterpiosin and nakiterpiosinone.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              371
_journal_page_last               383
_journal_paper_doi               10.1021/ja908626k
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C11 H14 O3'
_chemical_formula_weight         194.22
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1261(3)
_cell_length_b                   10.5633(5)
_cell_length_c                   12.4640(9)
_cell_measurement_temperature    100(2)
_cell_volume                     938.23(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6461
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         7.11
_exptl_absorpt_coefficient_mu    0.814
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       0.0026(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          1.262
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+0.4694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                900
_reflns_number_total             956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja908626k_si_003.cif
_cod_data_source_block           26
_cod_database_code               4101660
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5384(3) 0.30459(15) 0.36903(13) 0.0266(5) Uani 1 1 d . . .
O2 O 0.4305(3) 0.39461(17) 0.15756(14) 0.0298(5) Uani 1 1 d . . .
O3 O 0.4288(3) 0.53818(17) 0.56667(12) 0.0316(5) Uani 1 1 d . . .
C1 C 0.4615(4) 0.4793(2) 0.24477(18) 0.0240(6) Uani 1 1 d . . .
C2 C 0.2832(4) 0.5134(2) 0.3036(2) 0.0252(6) Uani 1 1 d . . .
C3 C 0.3275(4) 0.6059(3) 0.3947(2) 0.0255(6) Uani 1 1 d . . .
C4 C 0.4646(4) 0.5466(2) 0.47126(18) 0.0239(6) Uani 1 1 d . . .
C5 C 0.6502(4) 0.4989(2) 0.42434(18) 0.0215(6) Uani 1 1 d . . .
C6 C 0.7387(4) 0.3947(2) 0.4955(2) 0.0263(6) Uani 1 1 d . . .
C7 C 0.7130(4) 0.2763(2) 0.4242(2) 0.0283(6) Uani 1 1 d . . .
C8 C 0.8539(4) 0.2880(2) 0.3343(2) 0.0286(6) Uani 1 1 d . . .
C9 C 0.7888(4) 0.3780(2) 0.2709(2) 0.0251(6) Uani 1 1 d . . .
C10 C 0.6048(4) 0.4202(2) 0.31892(18) 0.0233(6) Uani 1 1 d . . .
C11 C 0.7790(4) 0.6131(3) 0.4054(2) 0.0256(6) Uani 1 1 d . . .
H1 H 0.518(4) 0.555(2) 0.2201(18) 0.019(6) Uiso 1 1 d . . .
H2O H 0.333(6) 0.413(3) 0.129(3) 0.049(11) Uiso 1 1 d . . .
H2A H 0.196(4) 0.552(2) 0.253(2) 0.022(7) Uiso 1 1 d . . .
H2B H 0.221(4) 0.441(3) 0.332(2) 0.024(7) Uiso 1 1 d . . .
H3A H 0.386(4) 0.682(3) 0.366(2) 0.023(7) Uiso 1 1 d . . .
H3B H 0.217(5) 0.626(3) 0.435(2) 0.035(8) Uiso 1 1 d . . .
H6A H 0.877(5) 0.408(3) 0.508(2) 0.036(8) Uiso 1 1 d . . .
H6B H 0.666(4) 0.388(2) 0.5605(19) 0.010(6) Uiso 1 1 d . . .
H7 H 0.708(4) 0.196(2) 0.460(2) 0.027(7) Uiso 1 1 d . . .
H8 H 0.973(4) 0.247(2) 0.3299(19) 0.020(7) Uiso 1 1 d . . .
H9 H 0.848(4) 0.412(3) 0.213(2) 0.027(7) Uiso 1 1 d . . .
H11A H 0.715(5) 0.681(3) 0.361(2) 0.034(8) Uiso 1 1 d . . .
H11B H 0.895(4) 0.582(2) 0.3711(19) 0.022(7) Uiso 1 1 d . . .
H11C H 0.808(4) 0.653(3) 0.471(2) 0.037(8) Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C7 95.62(19) . . ?
C1 O2 H2O 109(2) . . ?
O2 C1 C2 112.9(2) . . ?
O2 C1 C10 108.1(2) . . ?
C2 C1 C10 111.7(2) . . ?
O2 C1 H1 110.4(14) . . ?
C2 C1 H1 108.4(16) . . ?
C10 C1 H1 105.0(17) . . ?
C1 C2 C3 109.8(2) . . ?
C1 C2 H2A 108.8(16) . . ?
C3 C2 H2A 110.3(15) . . ?
C1 C2 H2B 112.5(17) . . ?
C3 C2 H2B 109.3(16) . . ?
H2A C2 H2B 106(2) . . ?
C4 C3 C2 109.8(2) . . ?
C4 C3 H3A 107.5(17) . . ?
C2 C3 H3A 109.6(15) . . ?
C4 C3 H3B 107.2(18) . . ?
C2 C3 H3B 110.9(18) . . ?
H3A C3 H3B 112(2) . . ?
O3 C4 C3 120.9(3) . . ?
O3 C4 C5 121.9(2) . . ?
C3 C4 C5 117.15(19) . . ?
C4 C5 C11 108.50(19) . . ?
C4 C5 C6 111.53(19) . . ?
C11 C5 C6 113.8(2) . . ?
C4 C5 C10 108.2(2) . . ?
C11 C5 C10 114.0(2) . . ?
C6 C5 C10 100.62(18) . . ?
C7 C6 C5 101.43(19) . . ?
C7 C6 H6A 108.7(16) . . ?
C5 C6 H6A 112.9(16) . . ?
C7 C6 H6B 111.0(14) . . ?
C5 C6 H6B 108.2(15) . . ?
H6A C6 H6B 114(2) . . ?
O1 C7 C8 101.6(2) . . ?
O1 C7 C6 101.9(2) . . ?
C8 C7 C6 106.4(2) . . ?
O1 C7 H7 111.6(18) . . ?
C8 C7 H7 116.1(16) . . ?
C6 C7 H7 117.2(16) . . ?
C9 C8 C7 105.7(2) . . ?
C9 C8 H8 127.2(15) . . ?
C7 C8 H8 126.6(15) . . ?
C8 C9 C10 106.3(2) . . ?
C8 C9 H9 126.6(19) . . ?
C10 C9 H9 126.9(18) . . ?
O1 C10 C9 101.89(19) . . ?
O1 C10 C1 113.0(2) . . ?
C9 C10 C1 117.8(2) . . ?
O1 C10 C5 98.69(17) . . ?
C9 C10 C5 107.8(2) . . ?
C1 C10 C5 115.24(19) . . ?
C5 C11 H11A 111.6(18) . . ?
C5 C11 H11B 107.8(15) . . ?
H11A C11 H11B 112(2) . . ?
C5 C11 H11C 110.6(18) . . ?
H11A C11 H11C 105(2) . . ?
H11B C11 H11C 110(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.451(3) . ?
O1 C7 1.453(3) . ?
O2 C1 1.425(3) . ?
O2 H2O 0.81(4) . ?
O3 C4 1.219(3) . ?
C1 C2 1.511(4) . ?
C1 C10 1.512(4) . ?
C1 H1 0.95(3) . ?
C2 C3 1.531(3) . ?
C2 H2A 0.97(3) . ?
C2 H2B 0.95(3) . ?
C3 C4 1.502(4) . ?
C3 H3A 0.97(3) . ?
C3 H3B 0.96(3) . ?
C4 C5 1.531(4) . ?
C5 C11 1.534(4) . ?
C5 C6 1.548(3) . ?
C5 C10 1.589(3) . ?
C6 C7 1.546(4) . ?
C6 H6A 1.01(3) . ?
C6 H6B 0.97(2) . ?
C7 C8 1.510(4) . ?
C7 H7 0.95(3) . ?
C8 C9 1.321(4) . ?
C8 H8 0.95(3) . ?
C9 C10 1.508(4) . ?
C9 H9 0.92(3) . ?
C11 H11A 1.02(3) . ?
C11 H11B 0.99(3) . ?
C11 H11C 0.94(3) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 -179.2(2) . . . . ?
C10 C1 C2 C3 58.7(3) . . . . ?
C1 C2 C3 C4 -59.2(3) . . . . ?
C2 C3 C4 O3 -124.7(3) . . . . ?
C2 C3 C4 C5 55.8(3) . . . . ?
O3 C4 C5 C11 -101.8(3) . . . . ?
C3 C4 C5 C11 77.6(3) . . . . ?
O3 C4 C5 C6 24.3(3) . . . . ?
C3 C4 C5 C6 -156.3(2) . . . . ?
O3 C4 C5 C10 134.0(2) . . . . ?
C3 C4 C5 C10 -46.5(3) . . . . ?
C4 C5 C6 C7 109.9(2) . . . . ?
C11 C5 C6 C7 -126.9(2) . . . . ?
C10 C5 C6 C7 -4.6(3) . . . . ?
C10 O1 C7 C8 -50.1(2) . . . . ?
C10 O1 C7 C6 59.6(2) . . . . ?
C5 C6 C7 O1 -32.6(2) . . . . ?
C5 C6 C7 C8 73.4(3) . . . . ?
O1 C7 C8 C9 33.5(3) . . . . ?
C6 C7 C8 C9 -72.8(3) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C7 O1 C10 C9 49.1(2) . . . . ?
C7 O1 C10 C1 176.5(2) . . . . ?
C7 O1 C10 C5 -61.3(2) . . . . ?
C8 C9 C10 O1 -30.8(3) . . . . ?
C8 C9 C10 C1 -155.0(2) . . . . ?
C8 C9 C10 C5 72.5(2) . . . . ?
O2 C1 C10 O1 -64.8(3) . . . . ?
C2 C1 C10 O1 60.0(2) . . . . ?
O2 C1 C10 C9 53.6(3) . . . . ?
C2 C1 C10 C9 178.5(2) . . . . ?
O2 C1 C10 C5 -177.2(2) . . . . ?
C2 C1 C10 C5 -52.4(3) . . . . ?
C4 C5 C10 O1 -76.7(2) . . . . ?
C11 C5 C10 O1 162.6(2) . . . . ?
C6 C5 C10 O1 40.4(2) . . . . ?
C4 C5 C10 C9 177.79(19) . . . . ?
C11 C5 C10 C9 57.0(3) . . . . ?
C6 C5 C10 C9 -65.2(2) . . . . ?
C4 C5 C10 C1 43.9(3) . . . . ?
C11 C5 C10 C1 -76.8(3) . . . . ?
C6 C5 C10 C1 161.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660054
