#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/32/1503211.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_1503211
loop_
_publ_author_name
'Jones, Brian D.'
'La Clair, James J.'
'Moore, Curtis E.'
'Rheingold, Arnold L.'
'Burkart, Michael D.'
_publ_section_title
;
 Convergent route to the spirohexenolide macrocycle.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4516
_journal_page_last               4519
_journal_paper_doi               10.1021/ol1018163
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C26 H32 O5'
_chemical_formula_weight         424.52
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.811(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.834(5)
_cell_length_b                   12.224(3)
_cell_length_c                   8.784(2)
_cell_measurement_reflns_used    2647
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.90
_cell_measurement_theta_min      2.57
_cell_volume                     2232.1(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0805
_diffrn_reflns_av_sigmaI/netI    0.1006
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20594
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         0.98
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Blade
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0082(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         5125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0580
_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)+(0.0510P)²+0.4409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                2863
_reflns_number_total             5125
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol1018163_si_004.cif
_cod_data_source_block           burk13
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2232.0(9)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1503211
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.24071(7) 0.83303(12) 0.48230(19) 0.0274(4) Uani 1 1 d .
O2 O 0.16205(7) 0.71605(11) 0.40989(17) 0.0205(4) Uani 1 1 d .
O3 O 0.23251(7) 0.48236(11) 0.25323(18) 0.0212(4) Uani 1 1 d .
O4 O 0.47711(8) 0.79986(15) 0.4926(2) 0.0396(5) Uani 1 1 d .
O5 O 0.56446(8) 0.67765(15) 0.7597(2) 0.0374(5) Uani 1 1 d .
H5O H 0.5389 0.6778 0.8298 0.056 Uiso 1 1 calc R
C1 C 0.22568(11) 0.74465(18) 0.4288(3) 0.0207(5) Uani 1 1 d .
C2 C 0.26585(10) 0.65588(17) 0.3772(3) 0.0194(5) Uani 1 1 d .
C3 C 0.22457(10) 0.57768(17) 0.3206(3) 0.0188(5) Uani 1 1 d .
C4 C 0.15554(10) 0.60539(17) 0.3480(3) 0.0175(5) Uani 1 1 d .
C5 C 0.10894(10) 0.61456(18) 0.2063(3) 0.0217(5) Uani 1 1 d .
H5A H 0.1309 0.6549 0.1270 0.026 Uiso 1 1 calc R
H5B H 0.0718 0.6594 0.2331 0.026 Uiso 1 1 calc R
C6 C 0.08303(11) 0.50661(18) 0.1360(3) 0.0245(6) Uani 1 1 d .
H6 H 0.0376 0.5221 0.0987 0.029 Uiso 1 1 calc R
C7 C 0.07910(10) 0.41655(18) 0.2528(3) 0.0219(5) Uani 1 1 d .
C8 C 0.10007(10) 0.42767(18) 0.3980(3) 0.0212(5) Uani 1 1 d .
H8 H 0.0966 0.3653 0.4614 0.025 Uiso 1 1 calc R
C9 C 0.12898(10) 0.52945(17) 0.4733(3) 0.0191(5) Uani 1 1 d .
C10 C 0.18274(10) 0.50864(18) 0.5957(3) 0.0201(5) Uani 1 1 d .
H10 H 0.1877 0.5659 0.6687 0.024 Uiso 1 1 calc R
C11 C 0.22463(10) 0.42623(18) 0.6220(3) 0.0228(5) Uani 1 1 d .
C12 C 0.27706(11) 0.44525(19) 0.7404(3) 0.0254(6) Uani 1 1 d .
H12 H 0.2712 0.5046 0.8079 0.030 Uiso 1 1 calc R
C13 C 0.33172(11) 0.38916(19) 0.7642(3) 0.0277(6) Uani 1 1 d .
H13 H 0.3361 0.3226 0.7101 0.033 Uiso 1 1 calc R
C14 C 0.38668(11) 0.4253(2) 0.8714(3) 0.0303(6) Uani 1 1 d .
H14A H 0.4013 0.3628 0.9365 0.036 Uiso 1 1 calc R
H14B H 0.3717 0.4836 0.9387 0.036 Uiso 1 1 calc R
C15 C 0.44353(11) 0.4683(2) 0.7854(3) 0.0319(6) Uani 1 1 d .
H15A H 0.4788 0.4901 0.8604 0.038 Uiso 1 1 calc R
H15B H 0.4597 0.4088 0.7219 0.038 Uiso 1 1 calc R
C16 C 0.42549(12) 0.56398(19) 0.6856(3) 0.0278(6) Uani 1 1 d .
H16 H 0.3809 0.5807 0.6729 0.033 Uiso 1 1 calc R
C17 C 0.46502(11) 0.62879(19) 0.6122(3) 0.0264(6) Uani 1 1 d .
C18 C 0.44014(11) 0.7241(2) 0.5224(3) 0.0271(6) Uani 1 1 d .
C19 C 0.37152(11) 0.7340(2) 0.4724(3) 0.0278(6) Uani 1 1 d .
H19 H 0.3519 0.8036 0.4810 0.033 Uiso 1 1 calc R
C20 C 0.33504(11) 0.65236(19) 0.4162(3) 0.0239(6) Uani 1 1 d .
H20 H 0.3561 0.5849 0.3997 0.029 Uiso 1 1 calc R
C21 C 0.29545(11) 0.4548(2) 0.2040(3) 0.0340(7) Uani 1 1 d .
H21A H 0.3166 0.5211 0.1696 0.051 Uiso 1 1 calc R
H21B H 0.2908 0.4022 0.1197 0.051 Uiso 1 1 calc R
H21C H 0.3215 0.4223 0.2893 0.051 Uiso 1 1 calc R
C22 C 0.11735(12) 0.4712(2) -0.0062(3) 0.0305(6) Uani 1 1 d .
H22A H 0.1619 0.4507 0.0241 0.046 Uiso 1 1 calc R
H22B H 0.1172 0.5319 -0.0790 0.046 Uiso 1 1 calc R
H22C H 0.0948 0.4083 -0.0541 0.046 Uiso 1 1 calc R
C23 C 0.04607(12) 0.31253(19) 0.1967(3) 0.0320(6) Uani 1 1 d .
H23A H 0.0732 0.2747 0.1264 0.048 Uiso 1 1 calc R
H23B H 0.0046 0.3306 0.1436 0.048 Uiso 1 1 calc R
H23C H 0.0391 0.2649 0.2838 0.048 Uiso 1 1 calc R
C24 C 0.07410(10) 0.58726(19) 0.5519(3) 0.0241(6) Uani 1 1 d .
H24A H 0.0410 0.6110 0.4745 0.036 Uiso 1 1 calc R
H24B H 0.0913 0.6511 0.6084 0.036 Uiso 1 1 calc R
H24C H 0.0552 0.5364 0.6227 0.036 Uiso 1 1 calc R
C25 C 0.22628(12) 0.31942(18) 0.5358(3) 0.0299(6) Uani 1 1 d .
H25A H 0.1953 0.3222 0.4470 0.045 Uiso 1 1 calc R
H25B H 0.2151 0.2593 0.6029 0.045 Uiso 1 1 calc R
H25C H 0.2696 0.3075 0.5018 0.045 Uiso 1 1 calc R
C26 C 0.53738(11) 0.6163(2) 0.6340(3) 0.0332(6) Uani 1 1 d .
H26A H 0.5480 0.5381 0.6500 0.040 Uiso 1 1 calc R
H26B H 0.5570 0.6405 0.5400 0.040 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O2 C4 110.28(16)
C3 O3 C21 118.80(17)
C26 O5 H5O 109.5
O1 C1 O2 119.9(2)
O1 C1 C2 130.1(2)
O2 C1 C2 110.02(18)
C3 C2 C20 131.0(2)
C3 C2 C1 105.94(19)
C20 C2 C1 121.7(2)
O3 C3 C2 133.6(2)
O3 C3 C4 114.65(18)
C2 C3 C4 111.72(19)
O2 C4 C3 101.58(16)
O2 C4 C5 105.84(16)
C3 C4 C5 116.46(19)
O2 C4 C9 108.37(17)
C3 C4 C9 111.26(17)
C5 C4 C9 112.31(17)
C4 C5 C6 116.73(18)
C4 C5 H5A 108.1
C6 C5 H5A 108.1
C4 C5 H5B 108.1
C6 C5 H5B 108.1
H5A C5 H5B 107.3
C7 C6 C5 112.69(19)
C7 C6 C22 113.22(19)
C5 C6 C22 113.37(19)
C7 C6 H6 105.5
C5 C6 H6 105.5
C22 C6 H6 105.5
C8 C7 C6 123.3(2)
C8 C7 C23 120.8(2)
C6 C7 C23 115.8(2)
C7 C8 C9 126.8(2)
C7 C8 H8 116.6
C9 C8 H8 116.6
C8 C9 C10 115.07(18)
C8 C9 C24 106.62(17)
C10 C9 C24 107.01(19)
C8 C9 C4 109.16(19)
C10 C9 C4 108.50(17)
C24 C9 C4 110.43(17)
C11 C10 C9 133.4(2)
C11 C10 H10 113.3
C9 C10 H10 113.3
C10 C11 C12 116.4(2)
C10 C11 C25 126.7(2)
C12 C11 C25 116.7(2)
C13 C12 C11 127.8(2)
C13 C12 H12 116.1
C11 C12 H12 116.1
C12 C13 C14 123.7(2)
C12 C13 H13 118.1
C14 C13 H13 118.1
C13 C14 C15 111.9(2)
C13 C14 H14A 109.2
C15 C14 H14A 109.2
C13 C14 H14B 109.2
C15 C14 H14B 109.2
H14A C14 H14B 107.9
C16 C15 C14 112.6(2)
C16 C15 H15A 109.1
C14 C15 H15A 109.1
C16 C15 H15B 109.1
C14 C15 H15B 109.1
H15A C15 H15B 107.8
C17 C16 C15 127.4(2)
C17 C16 H16 116.3
C15 C16 H16 116.3
C16 C17 C18 121.2(2)
C16 C17 C26 121.2(2)
C18 C17 C26 117.2(2)
O4 C18 C19 118.6(2)
O4 C18 C17 119.9(2)
C19 C18 C17 121.4(2)
C20 C19 C18 124.7(2)
C20 C19 H19 117.6
C18 C19 H19 117.6
C19 C20 C2 126.6(2)
C19 C20 H20 116.7
C2 C20 H20 116.7
O3 C21 H21A 109.5
O3 C21 H21B 109.5
H21A C21 H21B 109.5
O3 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C6 C22 H22A 109.5
C6 C22 H22B 109.5
H22A C22 H22B 109.5
C6 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C7 C23 H23A 109.5
C7 C23 H23B 109.5
H23A C23 H23B 109.5
C7 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C9 C24 H24A 109.5
C9 C24 H24B 109.5
H24A C24 H24B 109.5
C9 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C11 C25 H25A 109.5
C11 C25 H25B 109.5
H25A C25 H25B 109.5
C11 C25 H25C 109.5
H25A C25 H25C 109.5
H25B C25 H25C 109.5
O5 C26 C17 112.7(2)
O5 C26 H26A 109.1
C17 C26 H26A 109.1
O5 C26 H26B 109.1
C17 C26 H26B 109.1
H26A C26 H26B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.211(3)
O2 C1 1.370(3)
O2 C4 1.461(2)
O3 C3 1.322(2)
O3 C21 1.448(3)
O4 C18 1.243(3)
O5 C26 1.420(3)
O5 H5O 0.8400
C1 C2 1.461(3)
C2 C3 1.358(3)
C2 C20 1.460(3)
C3 C4 1.512(3)
C4 C5 1.531(3)
C4 C9 1.569(3)
C5 C6 1.539(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.511(3)
C6 C22 1.542(3)
C6 H6 1.0000
C7 C8 1.328(3)
C7 C23 1.513(3)
C8 C9 1.515(3)
C8 H8 0.9500
C9 C10 1.521(3)
C9 C24 1.545(3)
C10 C11 1.343(3)
C10 H10 0.9500
C11 C12 1.476(3)
C11 C25 1.511(3)
C12 C13 1.334(3)
C12 H12 0.9500
C13 C14 1.500(3)
C13 H13 0.9500
C14 C15 1.539(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.494(3)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C17 1.339(3)
C16 H16 0.9500
C17 C18 1.481(3)
C17 C26 1.515(3)
C18 C19 1.472(3)
C19 C20 1.329(3)
C19 H19 0.9500
C20 H20 0.9500
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
C23 H23A 0.9800
C23 H23B 0.9800
C23 H23C 0.9800
C24 H24A 0.9800
C24 H24B 0.9800
C24 H24C 0.9800
C25 H25A 0.9800
C25 H25B 0.9800
C25 H25C 0.9800
C26 H26A 0.9900
C26 H26B 0.9900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5O O4 0.84 2.01 2.840(3) 172.2 4_576
