#------------------------------------------------------------------------------
#$Date: 2014-07-11 17:35:18 +0300 (Fri, 11 Jul 2014) $
#$Revision: 120071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/65/1506556.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_1506556
loop_
_publ_author_name
'Calter, Michael A.'
'Tretyak, Olexandr A.'
'Flaschenriem, Christine'
_publ_section_title
;
 Formation of disubstituted beta-lactones using bifunctional catalysis.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1809
_journal_page_last               1812
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C15 H11 Cl O3'
_chemical_formula_weight         274.69
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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                 93.894(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8832(12)
_cell_length_b                   17.578(3)
_cell_length_c                   9.3048(14)
_cell_measurement_temperature    273(2)
_cell_volume                     1286.4(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0771
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14618
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.297
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.380
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.380
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.1329
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0950P)^2^+2.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2569
_refine_ls_wR_factor_ref         0.2689
_reflns_number_gt                2570
_reflns_number_total             3138
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    ol050411qsi20050223_051037.cif
_[local]_cod_data_source_block   asd
_cod_original_cell_volume        1286.4(3)
_cod_database_code               1506556
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
Cl1 Cl 0.32407(18) 0.09882(7) 0.49854(16) 0.0382(4) Uani 1 1 d .
O1 O 0.1295(4) -0.19259(18) 0.5161(3) 0.0241(8) Uani 1 1 d .
O2 O 0.3669(5) -0.2633(2) 0.5697(4) 0.0406(10) Uani 1 1 d .
O3 O 0.3902(4) -0.17862(19) 0.2790(4) 0.0246(8) Uani 1 1 d .
C1 C 0.1925(6) 0.0385(3) 0.3905(5) 0.0229(10) Uani 1 1 d .
C2 C 0.1964(6) -0.0395(2) 0.4206(5) 0.0206(9) Uani 1 1 d .
H2A H 0.2673 -0.0587 0.4960 0.025 Uiso 1 1 calc R
C3 C 0.0936(5) -0.0872(2) 0.3365(5) 0.0160(9) Uani 1 1 d .
C4 C -0.0084(6) -0.0585(3) 0.2222(5) 0.0236(10) Uani 1 1 d .
H4A H -0.0765 -0.0912 0.1646 0.028 Uiso 1 1 calc R
C5 C -0.0088(7) 0.0190(3) 0.1939(6) 0.0316(12) Uani 1 1 d .
H5 H -0.070(7) 0.041(3) 0.110(6) 0.035(15) Uiso 1 1 d .
C6 C 0.0912(7) 0.0679(3) 0.2785(6) 0.0311(12) Uani 1 1 d .
H6 H 0.088(8) 0.115(4) 0.268(7) 0.05(2) Uiso 1 1 d .
C7 C 0.0913(6) -0.1714(2) 0.3612(5) 0.0182(9) Uani 1 1 d .
H7 H -0.011(7) -0.194(3) 0.329(6) 0.024(13) Uiso 1 1 d .
C8 C 0.2700(6) -0.2321(3) 0.4869(5) 0.0246(10) Uani 1 1 d .
C9 C 0.2487(6) -0.2183(2) 0.3246(5) 0.0212(10) Uani 1 1 d .
H9 H 0.223(7) -0.258(3) 0.262(6) 0.026(14) Uiso 1 1 d .
C10 C 0.3920(6) -0.1618(3) 0.1346(5) 0.0214(10) Uani 1 1 d .
C11 C 0.5242(7) -0.1151(3) 0.0990(7) 0.0356(13) Uani 1 1 d .
H11 H 0.592(7) -0.094(3) 0.166(6) 0.023(14) Uiso 1 1 d .
C12 C 0.5420(9) -0.0970(4) -0.0442(7) 0.0487(16) Uani 1 1 d .
H12 H 0.648(8) -0.059(4) -0.058(7) 0.049(18) Uiso 1 1 d .
C13 C 0.4302(9) -0.1248(4) -0.1499(7) 0.0511(18) Uani 1 1 d .
H13 H 0.441(9) -0.117(4) -0.244(8) 0.053(19) Uiso 1 1 d .
C14 C 0.2992(8) -0.1705(4) -0.1134(6) 0.0421(15) Uani 1 1 d .
H14 H 0.225(6) -0.185(3) -0.180(5) 0.014(12) Uiso 1 1 d .
C15 C 0.2759(7) -0.1886(3) 0.0283(6) 0.0288(11) Uani 1 1 d .
H15 H 0.197(7) -0.217(3) 0.052(6) 0.031(16) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0419(8) 0.0268(7) 0.0468(8) -0.0156(6) 0.0096(6) -0.0187(6)
O1 0.0288(18) 0.0216(16) 0.0226(18) 0.0073(13) 0.0064(14) 0.0003(13)
O2 0.039(2) 0.038(2) 0.043(2) 0.0187(18) -0.0085(18) 0.0045(17)
O3 0.0223(16) 0.0278(18) 0.0242(18) -0.0036(14) 0.0048(13) -0.0010(13)
C1 0.022(2) 0.021(2) 0.027(3) -0.0056(19) 0.0095(19) -0.0089(18)
C2 0.023(2) 0.016(2) 0.023(2) -0.0020(17) 0.0031(19) -0.0026(17)
C3 0.016(2) 0.0116(19) 0.020(2) 0.0021(16) 0.0033(17) -0.0010(15)
C4 0.021(2) 0.024(2) 0.026(2) -0.0028(19) 0.0000(19) -0.0003(18)
C5 0.039(3) 0.029(3) 0.026(3) 0.009(2) -0.004(2) 0.006(2)
C6 0.039(3) 0.018(2) 0.037(3) 0.001(2) 0.012(2) 0.006(2)
C7 0.021(2) 0.016(2) 0.018(2) -0.0036(16) 0.0001(17) -0.0063(17)
C8 0.023(2) 0.018(2) 0.032(3) 0.0048(19) -0.005(2) -0.0046(18)
C9 0.026(2) 0.012(2) 0.026(2) -0.0027(18) -0.0014(19) 0.0036(17)
C10 0.019(2) 0.019(2) 0.027(2) -0.0055(18) 0.0064(18) 0.0087(17)
C11 0.032(3) 0.031(3) 0.045(3) -0.002(2) 0.010(3) 0.000(2)
C12 0.054(4) 0.047(4) 0.048(4) 0.009(3) 0.028(3) 0.009(3)
C13 0.064(4) 0.058(4) 0.033(4) 0.012(3) 0.021(3) 0.026(4)
C14 0.044(3) 0.057(4) 0.024(3) -0.001(3) -0.005(3) 0.028(3)
C15 0.027(3) 0.029(3) 0.031(3) 0.000(2) 0.006(2) 0.010(2)
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
C8 O1 C7 92.8(3)
C10 O3 C9 117.5(4)
C6 C1 C2 121.7(4)
C6 C1 Cl1 120.0(4)
C2 C1 Cl1 118.3(4)
C3 C2 C1 118.6(4)
C2 C3 C4 120.4(4)
C2 C3 C7 121.9(4)
C4 C3 C7 117.7(4)
C3 C4 C5 119.8(4)
C6 C5 C4 120.7(5)
C1 C6 C5 118.8(5)
O1 C7 C3 112.9(3)
O1 C7 C9 88.2(3)
C3 C7 C9 118.3(4)
O2 C8 O1 127.6(5)
O2 C8 C9 137.8(5)
O1 C8 C9 94.6(3)
O3 C9 C8 110.0(4)
O3 C9 C7 117.9(4)
C8 C9 C7 84.4(3)
O3 C10 C15 125.1(4)
O3 C10 C11 114.7(5)
C15 C10 C11 120.2(5)
C10 C11 C12 119.5(6)
C13 C12 C11 120.5(6)
C12 C13 C14 119.5(6)
C13 C14 C15 121.6(6)
C14 C15 C10 118.7(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.752(5)
O1 C8 1.351(6)
O1 C7 1.499(5)
O2 C8 1.181(6)
O3 C10 1.377(6)
O3 C9 1.405(6)
C1 C6 1.370(7)
C1 C2 1.400(6)
C2 C3 1.372(6)
C3 C4 1.384(6)
C3 C7 1.500(6)
C4 C5 1.389(7)
C5 C6 1.377(8)
C7 C9 1.546(6)
C8 C9 1.527(7)
C10 C15 1.384(7)
C10 C11 1.384(7)
C11 C12 1.386(9)
C12 C13 1.366(11)
C13 C14 1.369(10)
C14 C15 1.380(8)
_journal_paper_doi 10.1021/ol050411q