#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/20/4022032.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_4022032
loop_
_publ_author_name
'Wadih Ghattas'
'Corinna R. Hess'
'Gilles Iacazio'
'Renaud Hardré'
'Judith P. Klinman'
'Marius Réglier'
_publ_section_title
;
 Pathway for the Stereocontrolled Z and E Production of
 α,α-Difluorine-Substituted Phenyl Butenoates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8618
_journal_page_last               8621
_journal_paper_doi               10.1021/jo061022s
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C10 H8 F2 O2'
_chemical_formula_weight         198.16
_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                 90.25(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.51(1)
_cell_length_b                   5.662(1)
_cell_length_c                   9.238(3)
_cell_measurement_reflns_used    1803
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.49
_cell_volume                     915.9(6)
_computing_cell_refinement
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD (Brucker-Nonius, 1998)'
_computing_data_reduction
'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.885
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Phi scan'
_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  0.06
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1654
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.78
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .5
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0545
_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)+(0.0370P)²+0.4305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                1461
_reflns_number_total             1654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061022ssi20060516_084025.cif
_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/c'
_cod_database_code               4022032
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
F1 F 0.33255(6) 0.11133(18) 0.69372(13) 0.0450(3) Uani 1 1 d .
F2 F 0.41790(7) -0.1141(2) 0.59273(12) 0.0505(4) Uani 1 1 d .
O2 O 0.41314(7) 0.1254(2) 0.92974(15) 0.0451(4) Uani 1 1 d .
H2 H 0.4440 0.1385 1.0070 0.054 Uiso 1 1 d R
O1 O 0.49438(7) -0.1462(2) 0.84277(15) 0.0431(4) Uani 1 1 d .
C1 C 0.43504(10) -0.0296(3) 0.83838(19) 0.0337(4) Uani 1 1 d .
C4 C 0.26035(12) -0.3200(4) 0.7897(3) 0.0539(6) Uani 1 1 d .
H4 H 0.2440 -0.5022 0.7972 0.065 Uiso 1 1 d R
C6 C 0.21921(12) 0.0408(4) 0.9278(3) 0.0551(6) Uani 1 1 d .
H6 H 0.2733 0.0548 0.9653 0.066 Uiso 1 1 d R
C3 C 0.33235(11) -0.2989(3) 0.7477(2) 0.0458(5) Uani 1 1 d .
H3 H 0.3664 -0.4326 0.7271 0.055 Uiso 1 1 d R
C5 C 0.20332(11) -0.1430(4) 0.8332(3) 0.0494(5) Uani 1 1 d .
C2 C 0.37718(10) -0.0810(3) 0.7171(2) 0.0367(4) Uani 1 1 d .
C7 C 0.16213(15) 0.1928(5) 0.9723(3) 0.0693(7) Uani 1 1 d .
H7 H 0.1764 0.3204 1.0343 0.083 Uiso 1 1 d R
C9 C 0.07207(15) -0.0164(6) 0.8281(4) 0.0902(10) Uani 1 1 d .
H9 H 0.0236 -0.0256 0.7916 0.108 Uiso 1 1 d R
C10 C 0.12801(14) -0.1713(5) 0.7844(4) 0.0741(8) Uani 1 1 d .
H10 H 0.1165 -0.3343 0.7226 0.089 Uiso 1 1 d R
C8 C 0.08868(15) 0.1645(6) 0.9214(4) 0.0828(9) Uani 1 1 d .
H8 H 0.0471 0.2616 0.9592 0.099 Uiso 1 1 d R
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
F1 0.0497(6) 0.0368(6) 0.0484(7) 0.0048(5) -0.0067(5) 0.0052(5)
F2 0.0569(7) 0.0614(8) 0.0331(7) -0.0077(5) 0.0032(5) -0.0001(5)
O2 0.0437(7) 0.0504(9) 0.0411(8) -0.0165(6) -0.0026(5) 0.0053(6)
O1 0.0420(7) 0.0463(8) 0.0411(8) -0.0050(6) -0.0005(5) 0.0080(6)
C1 0.0378(8) 0.0307(9) 0.0327(10) -0.0011(7) 0.0039(6) -0.0024(7)
C4 0.0528(12) 0.0397(12) 0.0691(15) 0.0024(10) 0.0000(10) -0.0071(9)
C6 0.0473(11) 0.0631(15) 0.0549(14) 0.0015(11) 0.0045(9) -0.0005(10)
C3 0.0476(10) 0.0329(10) 0.0568(13) -0.0053(9) -0.0027(8) -0.0007(8)
C5 0.0419(10) 0.0473(12) 0.0589(14) 0.0109(10) 0.0035(9) -0.0064(8)
C2 0.0423(9) 0.0336(10) 0.0342(10) -0.0016(7) 0.0007(7) 0.0042(7)
C7 0.0657(15) 0.0694(17) 0.0729(19) -0.0032(13) 0.0179(12) 0.0039(12)
C9 0.0409(13) 0.106(3) 0.123(3) 0.001(2) -0.0031(14) 0.0033(14)
C10 0.0460(12) 0.0754(18) 0.101(2) -0.0020(15) -0.0037(12) -0.0089(12)
C8 0.0554(15) 0.088(2) 0.105(3) 0.0126(18) 0.0244(15) 0.0173(14)
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'
F F 0.0171 0.0103 '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 H2 113.7
O1 C1 O2 127.02(17)
O1 C1 C2 118.44(15)
O2 C1 C2 114.42(15)
C3 C4 C5 131.7(2)
C3 C4 H4 111.1
C5 C4 H4 117.1
C7 C6 C5 120.8(2)
C7 C6 H6 121.8
C5 C6 H6 117.4
C4 C3 C2 129.23(19)
C4 C3 H3 124.4
C2 C3 H3 106.3
C6 C5 C10 118.3(2)
C6 C5 C4 123.3(2)
C10 C5 C4 118.3(2)
F1 C2 F2 106.16(15)
F1 C2 C3 113.02(15)
F2 C2 C3 108.86(15)
F1 C2 C1 109.96(14)
F2 C2 C1 107.12(15)
C3 C2 C1 111.41(16)
C8 C7 C6 120.1(3)
C8 C7 H7 122.4
C6 C7 H7 117.5
C8 C9 C10 120.8(3)
C8 C9 H9 118.0
C10 C9 H9 121.1
C9 C10 C5 120.2(3)
C9 C10 H10 123.8
C5 C10 H10 115.5
C9 C8 C7 119.8(3)
C9 C8 H8 119.3
C7 C8 H8 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.357(2)
F2 C2 1.367(2)
O2 C1 1.277(2)
O2 H2 0.8960
O1 C1 1.231(2)
C1 C2 1.535(3)
C4 C3 1.326(3)
C4 C5 1.472(3)
C4 H4 1.0729
C6 C7 1.383(3)
C6 C5 1.387(3)
C6 H6 1.0100
C3 C2 1.490(3)
C3 H3 0.9823
C5 C10 1.401(3)
C7 C8 1.377(4)
C7 H7 0.9545
C9 C8 1.369(5)
C9 C10 1.377(4)
C9 H9 0.9139
C10 H10 1.1032
C8 H8 0.9780
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194251
