#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023279.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_4023279
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 H22 Cl2 O4'
_chemical_formula_weight         457.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   7.9089(15)
_cell_length_b                   19.010(4)
_cell_length_c                   28.786(6)
_cell_measurement_reflns_used    945
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.26
_cell_volume                     4327.8(14)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2001)'
_computing_publication_material  SHELXTL
_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 0.931
_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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            21864
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.8734
_exptl_absorpt_correction_T_min  0.8607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0463
_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)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                3760
_reflns_number_total             4993
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702308f-File004.cif
_cod_data_source_block           joef064
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_database_code               4023279
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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 0.62890(7) -0.14598(3) 0.552553(16) 0.03474(16) Uani 1 1 d . . .
Cl2 Cl 1.19923(6) 0.16660(3) 0.567012(16) 0.03385(15) Uani 1 1 d . . .
O1 O 0.97300(15) -0.00745(6) 0.62974(4) 0.0219(3) Uani 1 1 d . . .
O2 O 0.79171(14) 0.08336(6) 0.63427(4) 0.0219(3) Uani 1 1 d . . .
O3 O 0.62422(18) 0.02026(7) 0.70475(4) 0.0337(3) Uani 1 1 d . . .
O4 O 0.45481(16) -0.03508(7) 0.65395(4) 0.0285(3) Uani 1 1 d . . .
C1 C 0.8187(2) -0.03552(9) 0.61165(6) 0.0204(4) Uani 1 1 d . . .
H1A H 0.8296 -0.0409 0.5772 0.025 Uiso 1 1 calc R . .
C2 C 0.9595(2) 0.06544(9) 0.62028(6) 0.0217(4) Uani 1 1 d . . .
H2A H 0.9743 0.0744 0.5863 0.026 Uiso 1 1 calc R . .
C3 C 0.6870(2) 0.02465(9) 0.62237(6) 0.0207(4) Uani 1 1 d . . .
C4 C 0.7857(2) -0.10660(9) 0.63290(6) 0.0217(4) Uani 1 1 d . . .
C5 C 0.8371(2) -0.12164(10) 0.67831(6) 0.0247(4) Uani 1 1 d . . .
H5A H 0.8923 -0.0862 0.6960 0.030 Uiso 1 1 calc R . .
C6 C 0.8094(2) -0.18681(11) 0.69803(7) 0.0304(4) Uani 1 1 d . . .
H6A H 0.8458 -0.1958 0.7289 0.036 Uiso 1 1 calc R . .
C7 C 0.7289(2) -0.23920(10) 0.67301(7) 0.0312(4) Uani 1 1 d . . .
H7A H 0.7107 -0.2841 0.6866 0.037 Uiso 1 1 calc R . .
C8 C 0.6749(2) -0.22585(10) 0.62813(7) 0.0283(4) Uani 1 1 d . . .
H8A H 0.6185 -0.2614 0.6109 0.034 Uiso 1 1 calc R . .
C9 C 0.7037(2) -0.16031(10) 0.60850(6) 0.0246(4) Uani 1 1 d . . .
C10 C 1.0877(2) 0.10632(9) 0.64756(6) 0.0210(4) Uani 1 1 d . . .
C11 C 1.2029(2) 0.15179(10) 0.62691(6) 0.0241(4) Uani 1 1 d . . .
C12 C 1.3238(2) 0.18715(10) 0.65273(7) 0.0294(4) Uani 1 1 d . . .
H12A H 1.4010 0.2182 0.6379 0.035 Uiso 1 1 calc R . .
C13 C 1.3309(2) 0.17688(10) 0.70021(7) 0.0298(4) Uani 1 1 d . . .
H13A H 1.4143 0.2006 0.7181 0.036 Uiso 1 1 calc R . .
C14 C 1.2164(2) 0.13193(10) 0.72203(7) 0.0285(4) Uani 1 1 d . . .
H14A H 1.2211 0.1251 0.7547 0.034 Uiso 1 1 calc R . .
C15 C 1.0955(2) 0.09721(9) 0.69571(6) 0.0247(4) Uani 1 1 d . . .
H15A H 1.0170 0.0668 0.7106 0.030 Uiso 1 1 calc R . .
C16 C 0.5707(2) 0.04205(10) 0.58068(6) 0.0238(4) Uani 1 1 d . . .
H16A H 0.5134 -0.0016 0.5705 0.029 Uiso 1 1 calc R . .
H16B H 0.4823 0.0754 0.5911 0.029 Uiso 1 1 calc R . .
C17 C 0.6630(2) 0.07359(10) 0.53975(6) 0.0241(4) Uani 1 1 d . . .
C18 C 0.6964(2) 0.14565(10) 0.53829(6) 0.0296(4) Uani 1 1 d . . .
H18A H 0.6565 0.1751 0.5626 0.036 Uiso 1 1 calc R . .
C19 C 0.7869(3) 0.17483(11) 0.50184(7) 0.0375(5) Uani 1 1 d . . .
H19A H 0.8099 0.2239 0.5015 0.045 Uiso 1 1 calc R . .
C20 C 0.8436(3) 0.13262(12) 0.46596(7) 0.0381(5) Uani 1 1 d . . .
H20A H 0.9070 0.1525 0.4412 0.046 Uiso 1 1 calc R . .
C21 C 0.8078(2) 0.06173(12) 0.46623(7) 0.0337(5) Uani 1 1 d . . .
H21A H 0.8443 0.0329 0.4412 0.040 Uiso 1 1 calc R . .
C22 C 0.7187(2) 0.03234(10) 0.50293(6) 0.0255(4) Uani 1 1 d . . .
H22A H 0.6953 -0.0167 0.5029 0.031 Uiso 1 1 calc R . .
C23 C 0.5857(2) 0.00515(9) 0.66567(6) 0.0237(4) Uani 1 1 d . . .
C24 C 0.3624(3) -0.06807(12) 0.69204(7) 0.0379(5) Uani 1 1 d . . .
H24A H 0.2784 -0.0349 0.7051 0.045 Uiso 1 1 calc R . .
H24B H 0.4412 -0.0822 0.7171 0.045 Uiso 1 1 calc R . .
C25 C 0.2761(3) -0.13093(12) 0.67234(8) 0.0406(5) Uani 1 1 d . . .
H25A H 0.2064 -0.1531 0.6964 0.061 Uiso 1 1 calc R . .
H25B H 0.3610 -0.1646 0.6613 0.061 Uiso 1 1 calc R . .
H25C H 0.2041 -0.1165 0.6463 0.061 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
C2 O1 C1 103.33(12) . . ?
C2 O2 C3 106.51(12) . . ?
C23 O4 C24 116.51(14) . . ?
O1 C1 C4 109.56(14) . . ?
O1 C1 C3 102.80(13) . . ?
C4 C1 C3 117.17(14) . . ?
O1 C2 O2 104.44(13) . . ?
O1 C2 C10 110.80(13) . . ?
O2 C2 C10 110.92(13) . . ?
O2 C3 C23 107.29(14) . . ?
O2 C3 C16 111.28(14) . . ?
C23 C3 C16 111.89(14) . . ?
O2 C3 C1 103.31(13) . . ?
C23 C3 C1 109.27(14) . . ?
C16 C3 C1 113.31(14) . . ?
C5 C4 C9 117.07(16) . . ?
C5 C4 C1 120.84(16) . . ?
C9 C4 C1 122.09(16) . . ?
C6 C5 C4 121.45(17) . . ?
C5 C6 C7 120.31(18) . . ?
C8 C7 C6 119.72(18) . . ?
C7 C8 C9 119.64(18) . . ?
C8 C9 C4 121.81(17) . . ?
C8 C9 Cl1 117.57(14) . . ?
C4 C9 Cl1 120.60(14) . . ?
C11 C10 C15 118.15(16) . . ?
C11 C10 C2 122.81(15) . . ?
C15 C10 C2 119.01(15) . . ?
C12 C11 C10 121.68(17) . . ?
C12 C11 Cl2 117.57(14) . . ?
C10 C11 Cl2 120.75(14) . . ?
C13 C12 C11 119.37(18) . . ?
C12 C13 C14 120.36(17) . . ?
C15 C14 C13 119.55(18) . . ?
C14 C15 C10 120.88(17) . . ?
C17 C16 C3 113.73(15) . . ?
C22 C17 C18 118.09(17) . . ?
C22 C17 C16 121.61(17) . . ?
C18 C17 C16 120.30(16) . . ?
C19 C18 C17 120.88(19) . . ?
C20 C19 C18 120.0(2) . . ?
C21 C20 C19 119.80(19) . . ?
C20 C21 C22 120.2(2) . . ?
C21 C22 C17 120.96(19) . . ?
O3 C23 O4 124.91(17) . . ?
O3 C23 C3 125.02(17) . . ?
O4 C23 C3 109.92(14) . . ?
O4 C24 C25 106.77(16) . . ?
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 C9 1.7370(19) . ?
Cl2 C11 1.7474(18) . ?
O1 C2 1.416(2) . ?
O1 C1 1.430(2) . ?
O2 C2 1.428(2) . ?
O2 C3 1.431(2) . ?
O3 C23 1.200(2) . ?
O4 C23 1.331(2) . ?
O4 C24 1.459(2) . ?
C1 C4 1.506(2) . ?
C1 C3 1.578(2) . ?
C2 C10 1.500(2) . ?
C3 C23 1.527(2) . ?
C3 C16 1.548(2) . ?
C4 C5 1.399(2) . ?
C4 C9 1.399(2) . ?
C5 C6 1.380(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.384(3) . ?
C8 C9 1.387(3) . ?
C10 C11 1.390(2) . ?
C10 C15 1.398(2) . ?
C11 C12 1.385(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.387(2) . ?
C16 C17 1.510(2) . ?
C17 C22 1.390(3) . ?
C17 C18 1.396(3) . ?
C18 C19 1.386(3) . ?
C19 C20 1.383(3) . ?
C20 C21 1.377(3) . ?
C21 C22 1.388(3) . ?
C24 C25 1.488(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
C2 O1 C1 C4 -160.75(13) . . . . ?
C2 O1 C1 C3 -35.46(15) . . . . ?
C1 O1 C2 O2 45.65(15) . . . . ?
C1 O1 C2 C10 165.14(13) . . . . ?
C3 O2 C2 O1 -36.75(16) . . . . ?
C3 O2 C2 C10 -156.16(13) . . . . ?
C2 O2 C3 C23 128.93(14) . . . . ?
C2 O2 C3 C16 -108.36(15) . . . . ?
C2 O2 C3 C1 13.54(16) . . . . ?
O1 C1 C3 O2 13.47(15) . . . . ?
C4 C1 C3 O2 133.64(15) . . . . ?
O1 C1 C3 C23 -100.50(15) . . . . ?
C4 C1 C3 C23 19.7(2) . . . . ?
O1 C1 C3 C16 134.00(14) . . . . ?
C4 C1 C3 C16 -105.84(17) . . . . ?
O1 C1 C4 C5 32.3(2) . . . . ?
C3 C1 C4 C5 -84.2(2) . . . . ?
O1 C1 C4 C9 -147.47(15) . . . . ?
C3 C1 C4 C9 96.0(2) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C1 C4 C5 C6 -179.24(17) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C4 -0.3(3) . . . . ?
C7 C8 C9 Cl1 -178.57(14) . . . . ?
C5 C4 C9 C8 -0.3(3) . . . . ?
C1 C4 C9 C8 179.45(16) . . . . ?
C5 C4 C9 Cl1 177.93(13) . . . . ?
C1 C4 C9 Cl1 -2.3(2) . . . . ?
O1 C2 C10 C11 124.84(17) . . . . ?
O2 C2 C10 C11 -119.64(17) . . . . ?
O1 C2 C10 C15 -53.4(2) . . . . ?
O2 C2 C10 C15 62.1(2) . . . . ?
C15 C10 C11 C12 0.5(3) . . . . ?
C2 C10 C11 C12 -177.80(16) . . . . ?
C15 C10 C11 Cl2 -179.27(13) . . . . ?
C2 C10 C11 Cl2 2.5(2) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
Cl2 C11 C12 C13 -179.99(15) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C11 C10 C15 C14 -0.8(3) . . . . ?
C2 C10 C15 C14 177.52(16) . . . . ?
O2 C3 C16 C17 49.99(19) . . . . ?
C23 C3 C16 C17 170.01(15) . . . . ?
C1 C3 C16 C17 -65.91(19) . . . . ?
C3 C16 C17 C22 95.3(2) . . . . ?
C3 C16 C17 C18 -84.0(2) . . . . ?
C22 C17 C18 C19 -1.9(3) . . . . ?
C16 C17 C18 C19 177.39(17) . . . . ?
C17 C18 C19 C20 0.8(3) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C20 C21 C22 -1.5(3) . . . . ?
C20 C21 C22 C17 0.4(3) . . . . ?
C18 C17 C22 C21 1.3(3) . . . . ?
C16 C17 C22 C21 -178.02(16) . . . . ?
C24 O4 C23 O3 -6.0(3) . . . . ?
C24 O4 C23 C3 169.81(15) . . . . ?
O2 C3 C23 O3 -21.4(2) . . . . ?
C16 C3 C23 O3 -143.68(18) . . . . ?
C1 C3 C23 O3 90.0(2) . . . . ?
O2 C3 C23 O4 162.84(13) . . . . ?
C16 C3 C23 O4 40.52(19) . . . . ?
C1 C3 C23 O4 -85.80(17) . . . . ?
C23 O4 C24 C25 -156.55(17) . . . . ?
