#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/19/7101989.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_7101989
loop_
_publ_author_name
'Marson, Charles M'
'Edaan, Esra'
'Morrell, James M'
'Coles, Simon J'
'Hursthouse, Michael B'
'Davies, David T'
_publ_section_title
;
 A catalytic asymmetric protocol for the enantioselective synthesis of
 3(2H)-furanones.
;
_journal_issue                   24
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2494
_journal_page_last               2496
_journal_paper_doi               10.1039/b701548h
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.27
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2005-01-11T20:05:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2521(3)
_cell_length_b                   9.3237(17)
_cell_length_c                   20.809(4)
_cell_measurement_temperature    120(2)
_cell_volume                     1213.0(3)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27007
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.93
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(8)
_refine_ls_extinction_coef       0.037(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   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0887P)²+0.1209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                2695
_reflns_number_total             2773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b701548h.txt
_cod_data_source_block           5src0001
_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_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7101989
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'
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
C1 C 0.06108(19) 0.25320(13) 0.10894(5) 0.0172(3) Uani 1 1 d .
C2 C -0.02611(19) 0.40121(13) 0.09119(6) 0.0182(2) Uani 1 1 d .
C3 C -0.1612(2) 0.44441(12) 0.14328(6) 0.0198(3) Uani 1 1 d .
H3 H -0.2373 0.5323 0.1466 0.024 Uiso 1 1 calc R
C4 C -0.16036(19) 0.33647(13) 0.18691(6) 0.0178(3) Uani 1 1 d .
C5 C 0.3014(2) 0.26072(15) 0.11874(6) 0.0231(3) Uani 1 1 d .
H5A H 0.336 0.3427 0.1463 0.035 Uiso 1 1 calc R
H5B H 0.3722 0.2723 0.077 0.035 Uiso 1 1 calc R
H5C H 0.3511 0.1721 0.1392 0.035 Uiso 1 1 calc R
C6 C -0.01273(19) 0.14065(13) 0.06059(5) 0.0170(2) Uani 1 1 d .
H6 H 0.0388 0.17 0.017 0.02 Uiso 1 1 calc R
C7 C 0.0685(2) -0.00996(13) 0.07409(6) 0.0218(3) Uani 1 1 d .
H7A H 0.0108 -0.0431 0.1158 0.026 Uiso 1 1 calc R
H7B H 0.2265 -0.0079 0.0775 0.026 Uiso 1 1 calc R
C8 C 0.0038(2) -0.11525(14) 0.02181(7) 0.0270(3) Uani 1 1 d .
H8A H -0.1522 -0.1147 0.0171 0.041 Uiso 1 1 calc R
H8B H 0.0515 -0.2118 0.0336 0.041 Uiso 1 1 calc R
H8C H 0.0702 -0.0871 -0.0189 0.041 Uiso 1 1 calc R
C9 C -0.2738(2) 0.32514(13) 0.24828(6) 0.0182(3) Uani 1 1 d .
C10 C -0.2255(2) 0.21464(14) 0.29127(6) 0.0211(3) Uani 1 1 d .
H10 H -0.1165 0.1472 0.2814 0.025 Uiso 1 1 calc R
C11 C -0.3385(2) 0.20414(14) 0.34874(6) 0.0250(3) Uani 1 1 d .
H11 H -0.3047 0.1302 0.3785 0.03 Uiso 1 1 calc R
C12 C -0.4999(2) 0.30115(14) 0.36275(6) 0.0255(3) Uani 1 1 d .
H12 H -0.5782 0.2922 0.4017 0.031 Uiso 1 1 calc R
C13 C -0.5477(2) 0.41146(15) 0.32020(6) 0.0248(3) Uani 1 1 d .
H13 H -0.6581 0.478 0.33 0.03 Uiso 1 1 calc R
C14 C -0.4335(2) 0.42368(13) 0.26350(6) 0.0218(3) Uani 1 1 d .
H14 H -0.4643 0.5 0.2347 0.026 Uiso 1 1 calc R
O1 O -0.03766(14) 0.22301(9) 0.17113(4) 0.0176(2) Uani 1 1 d .
O2 O 0.02104(16) 0.46466(10) 0.04143(4) 0.0232(2) Uani 1 1 d .
O3 O -0.23970(14) 0.14826(10) 0.06091(4) 0.0215(2) Uani 1 1 d .
H3A H -0.2883 0.1047 0.0287 0.032 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
O1 C1 C5 107.95(10)
O1 C1 C6 108.89(9)
C5 C1 C6 114.83(10)
O1 C1 C2 103.72(9)
C5 C1 C2 110.10(10)
C6 C1 C2 110.72(9)
O2 C2 C3 130.09(12)
O2 C2 C1 123.56(11)
C3 C2 C1 106.34(10)
C4 C3 C2 107.20(10)
C4 C3 H3 126.4
C2 C3 H3 126.4
O1 C4 C3 114.96(10)
O1 C4 C9 115.57(10)
C3 C4 C9 129.47(11)
C1 C5 H5A 109.5
C1 C5 H5B 109.5
H5A C5 H5B 109.5
C1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
O3 C6 C7 112.29(10)
O3 C6 C1 105.35(9)
C7 C6 C1 114.37(10)
O3 C6 H6 108.2
C7 C6 H6 108.2
C1 C6 H6 108.2
C6 C7 C8 112.05(10)
C6 C7 H7A 109.2
C8 C7 H7A 109.2
C6 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C14 C9 C10 119.69(11)
C14 C9 C4 119.84(11)
C10 C9 C4 120.46(11)
C11 C10 C9 119.49(12)
C11 C10 H10 120.3
C9 C10 H10 120.3
C12 C11 C10 120.26(12)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 120.38(12)
C11 C12 H12 119.8
C13 C12 H12 119.8
C14 C13 C12 119.54(13)
C14 C13 H13 120.2
C12 C13 H13 120.2
C13 C14 C9 120.62(12)
C13 C14 H14 119.7
C9 C14 H14 119.7
C4 O1 C1 107.77(9)
C6 O3 H3A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4612(14)
C1 C5 1.5178(16)
C1 C6 1.5252(16)
C1 C2 1.5290(17)
C2 O2 1.2285(15)
C2 C3 1.4322(17)
C3 C4 1.3555(17)
C3 H3 0.95
C4 O1 1.3474(14)
C4 C9 1.4645(17)
C5 H5A 0.98
C5 H5B 0.98
C5 H5C 0.98
C6 O3 1.4208(15)
C6 C7 1.5196(16)
C6 H6 1
C7 C8 1.5203(17)
C7 H7A 0.99
C7 H7B 0.99
C8 H8A 0.98
C8 H8B 0.98
C8 H8C 0.98
C9 C14 1.3935(18)
C9 C10 1.3973(17)
C10 C11 1.3923(18)
C10 H10 0.95
C11 C12 1.386(2)
C11 H11 0.95
C12 C13 1.3897(19)
C12 H12 0.95
C13 C14 1.3839(18)
C13 H13 0.95
C14 H14 0.95
O3 H3A 0.84
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21198042
