#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025079.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_4025079
loop_
_publ_author_name
'MinJin Kang'
'Brian D. Jones'
'Alexander L. Mandel'
'Justin C. Hammons'
'Antonio G. DiPasquale'
'Arnold L. Rheingold'
'James J. La Clair'
'Michael D. Burkart'
_publ_section_title
;
Isolation, Structure Elucidation, and Antitumor Activity of
Spirohexenolides A and B
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9054
_journal_page_last               9061
_journal_paper_doi               10.1021/jo901826d
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C25 H28 O5'
_chemical_formula_weight         408.47
_chemical_name_common            ESMedin_cmpd1
_chemical_name_systematic
;
 ?
;
_space_group.centring_type       P
_space_group_IT_number           4
_space_group.IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 105.946(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.0073(4)
_cell_length_b                   13.0187(9)
_cell_length_c                   12.0229(7)
_cell_measurement_reflns_used    4456
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.24
_cell_measurement_theta_min      3.82
_cell_volume                     1054.60(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         0.5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7195
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.00
_diffrn_reflns_theta_min         5.12
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  0.9317
_exptl_absorpt_correction_T_min  0.8409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0589P)²+0.0974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1114
_reflns_number_gt                2574
_reflns_number_total             3065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901826d_si_002.cif
_cod_data_source_block           burk03
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4025079
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
C1 C 0.8990(4) 0.4153(3) 0.3792(3) 0.0376(8) Uani 1 1 d . . .
C2 C 0.7680(5) 0.3370(3) 0.3022(3) 0.0396(8) Uani 1 1 d . . .
H2 H 0.6348 0.3575 0.2676 0.047 Uiso 1 1 calc R . .
C3 C 0.8162(5) 0.2424(3) 0.2767(3) 0.0425(9) Uani 1 1 d . . .
C4 C 1.0243(5) 0.2013(3) 0.3206(3) 0.0440(8) Uani 1 1 d . . .
H4 H 1.0126 0.1369 0.3637 0.053 Uiso 1 1 calc R . .
C5 C 1.1618(5) 0.2723(3) 0.4092(3) 0.0466(9) Uani 1 1 d . . .
H5A H 1.3001 0.2594 0.4071 0.056 Uiso 1 1 calc R . .
H5B H 1.1527 0.2530 0.4872 0.056 Uiso 1 1 calc R . .
C6 C 1.1209(5) 0.3876(3) 0.3927(2) 0.0394(8) Uani 1 1 d . . .
C7 C 0.8546(6) 0.4092(3) 0.4978(3) 0.0535(10) Uani 1 1 d . . .
H7A H 0.8861 0.3402 0.5301 0.080 Uiso 1 1 calc R . .
H7B H 0.7138 0.4238 0.4882 0.080 Uiso 1 1 calc R . .
H7C H 0.9358 0.4599 0.5504 0.080 Uiso 1 1 calc R . .
C8 C 0.6633(5) 0.1698(3) 0.2054(3) 0.0536(10) Uani 1 1 d . . .
H8A H 0.5347 0.2048 0.1805 0.080 Uiso 1 1 calc R . .
H8B H 0.6518 0.1096 0.2521 0.080 Uiso 1 1 calc R . .
H8C H 0.7039 0.1479 0.1374 0.080 Uiso 1 1 calc R . .
C9 C 1.1157(5) 0.1684(3) 0.2239(3) 0.0469(9) Uani 1 1 d . . .
H9A H 1.1358 0.2291 0.1802 0.070 Uiso 1 1 calc R . .
H9B H 1.0261 0.1204 0.1719 0.070 Uiso 1 1 calc R . .
H9C H 1.2436 0.1348 0.2579 0.070 Uiso 1 1 calc R . .
C10 C 0.8605(4) 0.5245(3) 0.3357(3) 0.0334(7) Uani 1 1 d . . .
H10 H 0.8894 0.5746 0.3954 0.040 Uiso 1 1 calc R . .
C11 C 0.7932(4) 0.5643(3) 0.2289(3) 0.0319(7) Uani 1 1 d . . .
C12 C 0.7280(5) 0.5043(3) 0.1174(3) 0.0391(8) Uani 1 1 d . . .
H12A H 0.7573 0.4313 0.1332 0.059 Uiso 1 1 calc R . .
H12B H 0.7993 0.5293 0.0632 0.059 Uiso 1 1 calc R . .
H12C H 0.5849 0.5133 0.0834 0.059 Uiso 1 1 calc R . .
C13 C 0.7826(4) 0.6758(3) 0.2163(3) 0.0339(7) Uani 1 1 d . . .
H13 H 0.8157 0.7149 0.2857 0.041 Uiso 1 1 calc R . .
C14 C 0.7316(4) 0.7280(3) 0.1180(3) 0.0388(8) Uani 1 1 d . . .
H14 H 0.6947 0.6892 0.0485 0.047 Uiso 1 1 calc R . .
C15 C 0.7267(5) 0.8425(3) 0.1064(3) 0.0417(8) Uani 1 1 d . . .
H15A H 0.7358 0.8737 0.1828 0.050 Uiso 1 1 calc R . .
H15B H 0.5984 0.8635 0.0528 0.050 Uiso 1 1 calc R . .
C16 C 0.8970(5) 0.8832(3) 0.0611(3) 0.0424(8) Uani 1 1 d . . .
H16 H 0.9116 0.8391 -0.0042 0.051 Uiso 1 1 calc R . .
C17 C 1.0857(5) 0.8798(3) 0.1589(3) 0.0416(8) Uani 1 1 d . . .
H17 H 1.1148 0.9388 0.2071 0.050 Uiso 1 1 calc R . .
C18 C 1.2153(4) 0.8032(3) 0.1844(3) 0.0390(8) Uani 1 1 d . . .
C19 C 1.2228(4) 0.7109(3) 0.1115(2) 0.0360(7) Uani 1 1 d . . .
H19A H 1.1027 0.7097 0.0449 0.043 Uiso 1 1 calc R . .
H19B H 1.3399 0.7162 0.0809 0.043 Uiso 1 1 calc R . .
C20 C 1.3624(5) 0.7981(3) 0.2971(3) 0.0442(9) Uani 1 1 d . . .
H20 H 1.4187 0.8593 0.3353 0.053 Uiso 1 1 calc R . .
C21 C 1.4163(4) 0.7083(3) 0.3454(3) 0.0434(9) Uani 1 1 d . . .
H21 H 1.5156 0.7042 0.4173 0.052 Uiso 1 1 calc R . .
C22 C 1.3250(4) 0.6161(3) 0.2895(2) 0.0343(7) Uani 1 1 d . . .
C23 C 1.3064(4) 0.5274(3) 0.3468(2) 0.0356(8) Uani 1 1 d . . .
C24 C 1.1885(4) 0.4391(3) 0.2962(2) 0.0314(7) Uani 1 1 d . . .
C25 C 1.3514(5) 0.5180(3) 0.4719(3) 0.0452(9) Uani 1 1 d . . .
O1 O 0.8581(4) 0.98669(19) 0.02234(19) 0.0501(7) Uani 1 1 d . . .
H1 H 0.8377 0.9890 -0.0498 0.075 Uiso 1 1 calc R . .
O2 O 1.2343(3) 0.61572(19) 0.17631(16) 0.0350(5) Uani 1 1 d . . .
O3 O 1.2460(3) 0.4370(2) 0.49709(16) 0.0473(6) Uani 1 1 d . . .
O4 O 1.1460(3) 0.40925(17) 0.19625(16) 0.0338(5) Uani 1 1 d . . .
O5 O 1.4569(4) 0.5668(2) 0.54940(19) 0.0594(8) Uani 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
C2 C1 C10 113.7(3) . . ?
C2 C1 C7 106.8(3) . . ?
C10 C1 C7 107.8(3) . . ?
C2 C1 C6 109.1(3) . . ?
C10 C1 C6 109.3(3) . . ?
C7 C1 C6 109.9(2) . . ?
C3 C2 C1 128.0(3) . . ?
C3 C2 H2 116.0 . . ?
C1 C2 H2 116.0 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 C8 121.6(3) . . ?
C4 C3 C8 116.5(3) . . ?
C3 C4 C5 113.1(3) . . ?
C3 C4 C9 113.5(3) . . ?
C5 C4 C9 112.3(3) . . ?
C3 C4 H4 105.7 . . ?
C5 C4 H4 105.7 . . ?
C9 C4 H4 105.7 . . ?
C4 C5 C6 116.2(3) . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
O3 C6 C24 102.7(3) . . ?
O3 C6 C5 105.8(2) . . ?
C24 C6 C5 116.4(3) . . ?
O3 C6 C1 109.3(2) . . ?
C24 C6 C1 109.2(2) . . ?
C5 C6 C1 112.7(3) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 132.4(3) . . ?
C11 C10 H10 113.8 . . ?
C1 C10 H10 113.8 . . ?
C10 C11 C13 118.5(3) . . ?
C10 C11 C12 126.1(3) . . ?
C13 C11 C12 115.4(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 126.6(3) . . ?
C14 C13 H13 116.7 . . ?
C11 C13 H13 116.7 . . ?
C13 C14 C15 126.0(3) . . ?
C13 C14 H14 117.0 . . ?
C15 C14 H14 117.0 . . ?
C14 C15 C16 112.1(3) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O1 C16 C17 109.2(3) . . ?
O1 C16 C15 110.1(3) . . ?
C17 C16 C15 108.3(3) . . ?
O1 C16 H16 109.7 . . ?
C17 C16 H16 109.7 . . ?
C15 C16 H16 109.7 . . ?
C18 C17 C16 126.8(3) . . ?
C18 C17 H17 116.6 . . ?
C16 C17 H17 116.6 . . ?
C17 C18 C20 120.8(3) . . ?
C17 C18 C19 126.8(3) . . ?
C20 C18 C19 112.2(3) . . ?
O2 C19 C18 112.1(2) . . ?
O2 C19 H19A 109.2 . . ?
C18 C19 H19A 109.2 . . ?
O2 C19 H19B 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C18 119.6(3) . . ?
C21 C20 H20 120.2 . . ?
C18 C20 H20 120.2 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
O2 C22 C23 115.2(3) . . ?
O2 C22 C21 120.4(3) . . ?
C23 C22 C21 124.1(3) . . ?
C22 C23 C24 125.4(3) . . ?
C22 C23 C25 124.6(3) . . ?
C24 C23 C25 107.7(3) . . ?
O4 C24 C23 128.6(3) . . ?
O4 C24 C6 124.5(3) . . ?
C23 C24 C6 106.9(3) . . ?
O5 C25 O3 119.4(3) . . ?
O5 C25 C23 132.1(4) . . ?
O3 C25 C23 108.5(3) . . ?
C16 O1 H1 109.5 . . ?
C22 O2 C19 118.9(3) . . ?
C25 O3 C6 112.3(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
C1 C2 1.508(5) . ?
C1 C10 1.513(5) . ?
C1 C7 1.542(4) . ?
C1 C6 1.561(4) . ?
C2 C3 1.335(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.506(4) . ?
C3 C8 1.507(5) . ?
C4 C5 1.534(5) . ?
C4 C9 1.534(5) . ?
C4 H4 1.0000 . ?
C5 C6 1.531(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O3 1.468(4) . ?
C6 C24 1.523(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.345(4) . ?
C10 H10 0.9500 . ?
C11 C13 1.459(4) . ?
C11 C12 1.510(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.325(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.496(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.536(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O1 1.427(4) . ?
C16 C17 1.509(4) . ?
C16 H16 1.0000 . ?
C17 C18 1.327(5) . ?
C17 H17 0.9500 . ?
C18 C20 1.461(4) . ?
C18 C19 1.496(5) . ?
C19 O2 1.454(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.314(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.437(5) . ?
C21 H21 0.9500 . ?
C22 O2 1.334(3) . ?
C22 C23 1.369(5) . ?
C23 C24 1.448(5) . ?
C23 C25 1.454(4) . ?
C24 O4 1.220(3) . ?
C25 O5 1.200(4) . ?
C25 O3 1.368(5) . ?
O1 H1 0.8400 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659095
