#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023278.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_4023278
loop_
_publ_author_name
'Andrew DeAngelis'
'Patricia Panne'
'Glenn P. A. Yap'
'Joseph M. Fox'
_publ_section_title
;
 Rh-Catalyzed Formation of Dioxolanes from α-Alkyl Diazoesters:
 Diastereoselective Cycloadditions of Carbonyl Ylides with Selectivity
 over β-Hydride Elimination
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1435
_journal_page_last               1439
_journal_paper_doi               10.1021/jo702308f
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C25 H24 O4'
_chemical_formula_weight         388.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.670(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.462(4)
_cell_length_b                   9.852(5)
_cell_length_c                   24.897(12)
_cell_measurement_reflns_used    920
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.64
_cell_volume                     2068.9(17)
_computing_cell_refinement       'SHELXTL, Sheldrick (2001)'
_computing_data_collection       'SMART, Bruker (2002)'
_computing_data_reduction        'SHELXTL, Sheldrick (2001)'
_computing_molecular_graphics    'SHELXTL, Sheldrick (2001)'
_computing_publication_material  'SHELXTL, Sheldrick (2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            22360
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.23
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9753
_exptl_absorpt_correction_T_min  0.9435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0493
_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)+(0.1167P)²+0.1183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1666
_reflns_number_gt                3771
_reflns_number_total             4772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702308f-File003.cif
_cod_data_source_block           joef047
_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 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023278
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.26130(11) 0.21558(10) 0.20522(4) 0.0321(2) Uani 1 1 d . . .
O2 O 0.11393(11) 0.03355(10) 0.17755(4) 0.0327(3) Uani 1 1 d . . .
O3 O 0.25858(13) 0.07040(12) 0.04938(4) 0.0397(3) Uani 1 1 d . . .
O4 O 0.04284(13) 0.15733(13) 0.08285(5) 0.0518(3) Uani 1 1 d . . .
C1 C 0.23747(15) 0.03951(13) 0.14234(5) 0.0276(3) Uani 1 1 d . . .
C2 C 0.16529(16) 0.09590(14) 0.08851(6) 0.0323(3) Uani 1 1 d . . .
C3 C 0.2086(2) 0.1317(2) -0.00254(7) 0.0624(6) Uani 1 1 d . . .
H3A H 0.1163 0.0821 -0.0199 0.075 Uiso 1 1 calc R . .
H3B H 0.1773 0.2274 0.0025 0.075 Uiso 1 1 calc R . .
C4 C 0.3414(3) 0.1248(3) -0.03621(8) 0.0892(9) Uani 1 1 d . . .
H4A H 0.3089 0.1615 -0.0720 0.134 Uiso 1 1 calc R . .
H4B H 0.3744 0.0301 -0.0397 0.134 Uiso 1 1 calc R . .
H4C H 0.4302 0.1781 -0.0196 0.134 Uiso 1 1 calc R . .
C5 C 0.31625(16) -0.09896(14) 0.13738(5) 0.0306(3) Uani 1 1 d . . .
H5A H 0.4006 -0.0906 0.1123 0.037 Uiso 1 1 calc R . .
H5B H 0.3676 -0.1246 0.1731 0.037 Uiso 1 1 calc R . .
C6 C 0.20557(15) -0.21163(13) 0.11778(5) 0.0298(3) Uani 1 1 d . . .
C7 C 0.12075(17) -0.28163(14) 0.15465(6) 0.0346(3) Uani 1 1 d . . .
H7A H 0.1296 -0.2549 0.1914 0.042 Uiso 1 1 calc R . .
C8 C 0.02372(18) -0.38969(15) 0.13832(7) 0.0407(4) Uani 1 1 d . . .
H8A H -0.0327 -0.4370 0.1639 0.049 Uiso 1 1 calc R . .
C9 C 0.00887(19) -0.42864(17) 0.08512(8) 0.0491(4) Uani 1 1 d . . .
H9A H -0.0570 -0.5032 0.0740 0.059 Uiso 1 1 calc R . .
C10 C 0.0901(2) -0.35878(18) 0.04812(7) 0.0516(5) Uani 1 1 d . . .
H10A H 0.0789 -0.3847 0.0113 0.062 Uiso 1 1 calc R . .
C11 C 0.18829(19) -0.25090(16) 0.06417(6) 0.0401(4) Uani 1 1 d . . .
H11A H 0.2439 -0.2037 0.0383 0.048 Uiso 1 1 calc R . .
C12 C 0.15877(17) 0.11519(14) 0.22362(5) 0.0314(3) Uani 1 1 d . . .
H12A H 0.2168 0.0587 0.2522 0.038 Uiso 1 1 calc R . .
C13 C 0.01710(17) 0.17990(14) 0.24542(5) 0.0317(3) Uani 1 1 d . . .
C14 C -0.0659(2) 0.28059(17) 0.21661(7) 0.0444(4) Uani 1 1 d . . .
H14A H -0.0362 0.3062 0.1820 0.053 Uiso 1 1 calc R . .
C15 C -0.1919(2) 0.34393(19) 0.23811(8) 0.0524(4) Uani 1 1 d . . .
H15A H -0.2479 0.4139 0.2184 0.063 Uiso 1 1 calc R . .
C16 C -0.2373(2) 0.30607(18) 0.28819(8) 0.0491(4) Uani 1 1 d . . .
H16A H -0.3237 0.3501 0.3030 0.059 Uiso 1 1 calc R . .
C17 C -0.1559(2) 0.20362(17) 0.31643(6) 0.0439(4) Uani 1 1 d . . .
H17A H -0.1872 0.1761 0.3506 0.053 Uiso 1 1 calc R . .
C18 C -0.02888(18) 0.14108(15) 0.29510(6) 0.0361(3) Uani 1 1 d . . .
H18A H 0.0271 0.0710 0.3147 0.043 Uiso 1 1 calc R . .
C19 C 0.35839(16) 0.14327(14) 0.17088(5) 0.0300(3) Uani 1 1 d . . .
H19A H 0.4398 0.0912 0.1938 0.036 Uiso 1 1 calc R . .
C20 C 0.44222(16) 0.23738(14) 0.13532(5) 0.0306(3) Uani 1 1 d . . .
C21 C 0.36982(18) 0.35444(14) 0.11444(6) 0.0360(3) Uani 1 1 d . . .
H21A H 0.2667 0.3781 0.1237 0.043 Uiso 1 1 calc R . .
C22 C 0.4482(2) 0.43747(16) 0.07985(6) 0.0421(4) Uani 1 1 d . . .
H22A H 0.3988 0.5180 0.0658 0.050 Uiso 1 1 calc R . .
C23 C 0.5976(2) 0.40278(18) 0.06604(7) 0.0457(4) Uani 1 1 d . . .
H23A H 0.6502 0.4591 0.0422 0.055 Uiso 1 1 calc R . .
C24 C 0.67069(19) 0.28706(19) 0.08666(7) 0.0473(4) Uani 1 1 d . . .
H24A H 0.7735 0.2634 0.0770 0.057 Uiso 1 1 calc R . .
C25 C 0.59320(17) 0.20481(16) 0.12175(6) 0.0391(4) Uani 1 1 d . . .
H25A H 0.6443 0.1258 0.1365 0.047 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C19 104.09(10) . . ?
C1 O2 C12 108.19(10) . . ?
C2 O3 C3 115.18(13) . . ?
O2 C1 C5 111.18(11) . . ?
O2 C1 C2 107.11(11) . . ?
C5 C1 C2 113.50(11) . . ?
O2 C1 C19 103.45(10) . . ?
C5 C1 C19 110.15(11) . . ?
C2 C1 C19 110.96(11) . . ?
O4 C2 O3 124.72(14) . . ?
O4 C2 C1 124.45(13) . . ?
O3 C2 C1 110.81(12) . . ?
C4 C3 O3 108.00(17) . . ?
C6 C5 C1 114.83(11) . . ?
C11 C6 C7 118.48(14) . . ?
C11 C6 C5 122.09(13) . . ?
C7 C6 C5 119.41(12) . . ?
C8 C7 C6 120.80(14) . . ?
C9 C8 C7 120.19(15) . . ?
C8 C9 C10 119.55(15) . . ?
C9 C10 C11 120.64(16) . . ?
C6 C11 C10 120.33(15) . . ?
O1 C12 O2 105.27(10) . . ?
O1 C12 C13 110.45(12) . . ?
O2 C12 C13 111.28(11) . . ?
C18 C13 C14 119.70(14) . . ?
C18 C13 C12 119.92(13) . . ?
C14 C13 C12 120.36(13) . . ?
C15 C14 C13 119.95(15) . . ?
C14 C15 C16 120.45(17) . . ?
C17 C16 C15 119.41(15) . . ?
C18 C17 C16 120.11(14) . . ?
C13 C18 C17 120.36(15) . . ?
O1 C19 C20 111.64(11) . . ?
O1 C19 C1 102.14(11) . . ?
C20 C19 C1 117.16(11) . . ?
C25 C20 C21 119.28(14) . . ?
C25 C20 C19 119.39(13) . . ?
C21 C20 C19 121.31(13) . . ?
C20 C21 C22 120.09(14) . . ?
C23 C22 C21 120.02(15) . . ?
C24 C23 C22 120.36(15) . . ?
C23 C24 C25 119.68(15) . . ?
C20 C25 C24 120.55(15) . . ?
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 C12 1.4162(17) . ?
O1 C19 1.4241(16) . ?
O2 C1 1.4192(16) . ?
O2 C12 1.4268(17) . ?
O3 C2 1.3270(18) . ?
O3 C3 1.458(2) . ?
O4 C2 1.1984(18) . ?
C1 C5 1.5278(19) . ?
C1 C2 1.5312(19) . ?
C1 C19 1.5742(19) . ?
C3 C4 1.457(3) . ?
C5 C6 1.5077(19) . ?
C6 C11 1.386(2) . ?
C6 C7 1.393(2) . ?
C7 C8 1.385(2) . ?
C8 C9 1.375(3) . ?
C9 C10 1.378(3) . ?
C10 C11 1.388(2) . ?
C12 C13 1.498(2) . ?
C13 C18 1.381(2) . ?
C13 C14 1.382(2) . ?
C14 C15 1.381(2) . ?
C15 C16 1.386(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.382(2) . ?
C19 C20 1.4996(19) . ?
C20 C25 1.386(2) . ?
C20 C21 1.387(2) . ?
C21 C22 1.394(2) . ?
C22 C23 1.379(2) . ?
C23 C24 1.377(3) . ?
C24 C25 1.394(2) . ?
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
C12 O2 C1 C5 114.43(12) . . . . ?
C12 O2 C1 C2 -121.05(12) . . . . ?
C12 O2 C1 C19 -3.76(13) . . . . ?
C3 O3 C2 O4 4.4(2) . . . . ?
C3 O3 C2 C1 -174.10(13) . . . . ?
O2 C1 C2 O4 18.76(19) . . . . ?
C5 C1 C2 O4 141.85(15) . . . . ?
C19 C1 C2 O4 -93.48(17) . . . . ?
O2 C1 C2 O3 -162.79(11) . . . . ?
C5 C1 C2 O3 -39.69(16) . . . . ?
C19 C1 C2 O3 84.98(14) . . . . ?
C2 O3 C3 C4 165.30(18) . . . . ?
O2 C1 C5 C6 57.74(15) . . . . ?
C2 C1 C5 C6 -63.09(15) . . . . ?
C19 C1 C5 C6 171.80(11) . . . . ?
C1 C5 C6 C11 96.84(16) . . . . ?
C1 C5 C6 C7 -84.99(15) . . . . ?
C11 C6 C7 C8 1.2(2) . . . . ?
C5 C6 C7 C8 -177.01(12) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C7 C6 C11 C10 -0.9(2) . . . . ?
C5 C6 C11 C10 177.33(14) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C19 O1 C12 O2 -41.55(13) . . . . ?
C19 O1 C12 C13 -161.77(11) . . . . ?
C1 O2 C12 O1 27.56(13) . . . . ?
C1 O2 C12 C13 147.23(11) . . . . ?
O1 C12 C13 C18 -131.09(13) . . . . ?
O2 C12 C13 C18 112.36(14) . . . . ?
O1 C12 C13 C14 47.42(17) . . . . ?
O2 C12 C13 C14 -69.13(17) . . . . ?
C18 C13 C14 C15 1.4(2) . . . . ?
C12 C13 C14 C15 -177.08(15) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C14 C13 C18 C17 -0.9(2) . . . . ?
C12 C13 C18 C17 177.64(13) . . . . ?
C16 C17 C18 C13 -0.3(2) . . . . ?
C12 O1 C19 C20 163.57(11) . . . . ?
C12 O1 C19 C1 37.58(12) . . . . ?
O2 C1 C19 O1 -20.77(12) . . . . ?
C5 C1 C19 O1 -139.67(11) . . . . ?
C2 C1 C19 O1 93.78(12) . . . . ?
O2 C1 C19 C20 -143.07(11) . . . . ?
C5 C1 C19 C20 98.03(13) . . . . ?
C2 C1 C19 C20 -28.52(15) . . . . ?
O1 C19 C20 C25 145.79(13) . . . . ?
C1 C19 C20 C25 -96.96(15) . . . . ?
O1 C19 C20 C21 -36.14(17) . . . . ?
C1 C19 C20 C21 81.11(16) . . . . ?
C25 C20 C21 C22 0.5(2) . . . . ?
C19 C20 C21 C22 -177.58(13) . . . . ?
C20 C21 C22 C23 0.5(2) . . . . ?
C21 C22 C23 C24 -0.7(2) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C21 C20 C25 C24 -1.3(2) . . . . ?
C19 C20 C25 C24 176.85(14) . . . . ?
C23 C24 C25 C20 1.1(2) . . . . ?
