#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/16/4101657.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_4101657
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            'C14 H16 Cl2 O3'
_chemical_formula_weight         303.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_space_group_name_H-M   'P c a b'
_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            8
_cell_length_a                   9.0904(3)
_cell_length_b                   10.3490(3)
_cell_length_c                   30.9898(14)
_cell_measurement_reflns_used    188
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      0.2
_cell_measurement_theta_min      0.02
_cell_volume                     2915.41(18)
_computing_cell_refinement       'HKL2000 v095.373'
_computing_data_collection       'collect, Nonius 1999'
_computing_data_reduction        'HKL2000 v095.373'
_computing_publication_material  'XCIF (Sheldrick and Bruker 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Kappa CCD'
_diffrn_measurement_method       Collect
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2434
_diffrn_reflns_theta_full        25.13
_diffrn_reflns_theta_max         25.13
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    0.446
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0057(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0640P)²+1.6806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1350
_reflns_number_gt                1607
_reflns_number_total             2434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja908626k_si_003.cif
_cod_data_source_block           11
_cod_original_sg_symbol_H-M      'P cab'
_cod_original_formula_sum        'C14 H16 Cl2 O3 '
_cod_database_code               4101657
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'
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
Cl1 Cl 0.05212(11) 0.27482(9) 0.59733(3) 0.0810(4) Uani 1 1 d . . .
Cl2 Cl 0.24253(9) 0.46342(10) 0.63786(3) 0.0703(4) Uani 1 1 d . . .
O1 O -0.0918(2) 0.5306(2) 0.53629(6) 0.0483(6) Uani 1 1 d . . .
H1 H -0.1246 0.4786 0.5188 0.072 Uiso 1 1 calc R . .
O2 O -0.2436(2) 0.72943(19) 0.57584(6) 0.0455(5) Uani 1 1 d . . .
O3 O -0.2550(2) 0.8744(2) 0.52348(7) 0.0561(6) Uani 1 1 d . . .
C1 C 0.0966(3) 0.4429(3) 0.60058(10) 0.0519(8) Uani 1 1 d . . .
H1A H 0.1327 0.4697 0.5722 0.062 Uiso 1 1 calc R . .
C2 C -0.0360(3) 0.5279(3) 0.61159(8) 0.0392(7) Uani 1 1 d . . .
H2 H -0.0025 0.6174 0.6085 0.047 Uiso 1 1 calc R . .
C3 C -0.1569(3) 0.5084(3) 0.57739(8) 0.0399(7) Uani 1 1 d . . .
H3 H -0.1902 0.4184 0.5786 0.048 Uiso 1 1 calc R . .
C4 C -0.2886(3) 0.5956(3) 0.58346(9) 0.0433(7) Uani 1 1 d . . .
H4 H -0.3265 0.5867 0.6129 0.052 Uiso 1 1 calc R . .
C5 C -0.2910(3) 0.7700(3) 0.53703(9) 0.0441(7) Uani 1 1 d . . .
C6 C -0.3883(3) 0.6717(3) 0.51644(10) 0.0522(8) Uani 1 1 d . . .
H6A H -0.3411 0.6341 0.4913 0.063 Uiso 1 1 calc R . .
H6B H -0.4809 0.7101 0.5077 0.063 Uiso 1 1 calc R . .
C7 C -0.4125(3) 0.5709(3) 0.55097(10) 0.0529(8) Uani 1 1 d . . .
H7A H -0.4056 0.4845 0.5390 0.063 Uiso 1 1 calc R . .
H7B H -0.5081 0.5814 0.5644 0.063 Uiso 1 1 calc R . .
C8 C -0.0933(3) 0.5159(3) 0.65727(9) 0.0425(7) Uani 1 1 d . . .
C9 C -0.1780(3) 0.4087(3) 0.66852(10) 0.0590(9) Uani 1 1 d . . .
H9 H -0.1934 0.3437 0.6483 0.071 Uiso 1 1 calc R . .
C10 C -0.2396(4) 0.3971(5) 0.70901(14) 0.0835(12) Uani 1 1 d . . .
H10 H -0.2969 0.3255 0.7158 0.100 Uiso 1 1 calc R . .
C11 C -0.2157(5) 0.4915(5) 0.73898(13) 0.0905(14) Uani 1 1 d . . .
H11 H -0.2573 0.4847 0.7663 0.109 Uiso 1 1 calc R . .
C12 C -0.1306(4) 0.5959(5) 0.72879(11) 0.0770(11) Uani 1 1 d . . .
H12 H -0.1125 0.6579 0.7498 0.092 Uiso 1 1 calc R . .
C13 C -0.0698(3) 0.6124(3) 0.68767(10) 0.0559(9) Uani 1 1 d . . .
C14 C 0.0156(5) 0.7342(3) 0.67798(12) 0.0787(12) Uani 1 1 d . . .
H14A H 0.0200 0.7870 0.7034 0.118 Uiso 1 1 calc R . .
H14B H -0.0324 0.7810 0.6553 0.118 Uiso 1 1 calc R . .
H14C H 0.1136 0.7119 0.6691 0.118 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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
C5 O2 C4 110.5(2) . . ?
C2 C1 Cl2 112.0(2) . . ?
C2 C1 Cl1 113.2(2) . . ?
Cl2 C1 Cl1 108.82(16) . . ?
C8 C2 C1 115.6(2) . . ?
C8 C2 C3 112.8(2) . . ?
C1 C2 C3 109.4(2) . . ?
O1 C3 C4 110.1(2) . . ?
O1 C3 C2 107.3(2) . . ?
C4 C3 C2 113.7(2) . . ?
O2 C4 C3 108.9(2) . . ?
O2 C4 C7 104.9(2) . . ?
C3 C4 C7 113.6(2) . . ?
O3 C5 O2 120.3(3) . . ?
O3 C5 C6 128.6(3) . . ?
O2 C5 C6 111.1(3) . . ?
C5 C6 C7 104.7(2) . . ?
C6 C7 C4 104.1(2) . . ?
C13 C8 C9 119.1(3) . . ?
C13 C8 C2 121.5(3) . . ?
C9 C8 C2 119.3(3) . . ?
C10 C9 C8 121.4(3) . . ?
C11 C10 C9 119.5(4) . . ?
C10 C11 C12 119.9(4) . . ?
C11 C12 C13 122.1(4) . . ?
C8 C13 C12 118.0(3) . . ?
C8 C13 C14 122.9(3) . . ?
C12 C13 C14 119.1(3) . . ?
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
Cl1 C1 1.788(3) . ?
Cl2 C1 1.772(3) . ?
O1 C3 1.423(3) . ?
O2 C5 1.345(3) . ?
O2 C4 1.463(3) . ?
O3 C5 1.204(3) . ?
C1 C2 1.531(4) . ?
C2 C8 1.514(4) . ?
C2 C3 1.540(4) . ?
C3 C4 1.511(4) . ?
C4 C7 1.532(4) . ?
C5 C6 1.491(4) . ?
C6 C7 1.511(4) . ?
C8 C13 1.390(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.379(5) . ?
C10 C11 1.365(6) . ?
C11 C12 1.366(6) . ?
C12 C13 1.399(5) . ?
C13 C14 1.510(5) . ?
