#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:22:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180136 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/33/7103339.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_7103339
loop_
_publ_author_name
'Rudler, Henri'
'Parlier, Andrée'
'Hamon, Louis'
'Herson, Patrick'
'Daran, Jean-Claude'
_publ_section_title
;
 Lactonizations of carboxylic acid-substituted 3-fluorodihydropyridines
 with electrophiles: peculiar behaviour of F(+).
;
_journal_issue                   35
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4150
_journal_page_last               4152
_journal_paper_doi               10.1039/b807092j
_journal_year                    2008
_chemical_formula_moiety         'C14 H17 F2 N O4'
_chemical_formula_sum            'C14 H17 F2 N O4'
_chemical_formula_weight         301.29
_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                   13.566(3)
_cell_length_b                   10.620(2)
_cell_length_c                   18.434(4)
_cell_measurement_reflns_used    2332
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.20
_cell_measurement_theta_min      2.45
_cell_volume                     2655.9(9)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.2632
_diffrn_measured_fraction_theta_full 0.836
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_device_type  'Oxford-Diffraction XCALIBUR'
_diffrn_measurement_method       'ω and φ'
_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  0.1488
_diffrn_reflns_av_sigmaI/netI    0.1961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5889
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED (Oxford Diffraction, 2006)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1596
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.1648
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1051P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.2136
_reflns_number_gt                627
_reflns_number_total             1596
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b807092j.txt
_cod_data_source_block           HRFF
_cod_database_code               7103339
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
O1 O 0.3989(4) 0.2654(6) 0.5317(3) 0.063(2) Uani 1 1 d . . .
O2 O 0.4526(3) 0.2345(6) 0.4224(3) 0.0443(17) Uani 1 1 d . . .
N8 N 0.5527(4) 0.3375(8) 0.3353(4) 0.042(2) Uani 1 1 d . . .
O81 O 0.5100(4) 0.4869(7) 0.2519(3) 0.050(2) Uani 1 1 d . . .
O82 O 0.4222(4) 0.3082(6) 0.2648(3) 0.0487(19) Uani 1 1 d . . .
F1 F 0.5953(3) 0.0532(5) 0.4351(2) 0.0490(15) Uani 1 1 d . . .
F2 F 0.6899(3) 0.1452(5) 0.3564(2) 0.0494(15) Uani 1 1 d . . .
C1 C 0.5278(5) 0.2213(10) 0.3699(4) 0.041(3) Uani 1 1 d . . .
H1 H 0.5058 0.1614 0.3329 0.049 Uiso 1 1 calc R . .
C3 C 0.4690(5) 0.2561(9) 0.4933(5) 0.043(2) Uani 1 1 d . . .
C4 C 0.5749(4) 0.2682(9) 0.5257(4) 0.040(2) Uani 1 1 d . . .
C5 C 0.6544(5) 0.2567(9) 0.4650(4) 0.042(3) Uani 1 1 d . . .
H5 H 0.7160 0.2249 0.4860 0.050 Uiso 1 1 calc R . .
C6 C 0.6741(5) 0.3787(10) 0.4265(4) 0.042(3) Uani 1 1 d . . .
H6 H 0.7229 0.4311 0.4448 0.050 Uiso 1 1 calc R . .
C7 C 0.6249(5) 0.4165(9) 0.3667(4) 0.041(3) Uani 1 1 d . . .
H7 H 0.6384 0.4946 0.3462 0.049 Uiso 1 1 calc R . .
C9 C 0.6182(5) 0.1667(10) 0.4086(5) 0.039(3) Uani 1 1 d . . .
C41 C 0.5792(5) 0.3972(10) 0.5633(4) 0.049(3) Uani 1 1 d . . .
H41A H 0.5771 0.4629 0.5268 0.059 Uiso 1 1 calc R . .
H41B H 0.5216 0.4068 0.5940 0.059 Uiso 1 1 calc R . .
C42 C 0.6715(4) 0.4136(10) 0.6090(4) 0.051(3) Uani 1 1 d . . .
H42A H 0.7289 0.4115 0.5777 0.061 Uiso 1 1 calc R . .
H42B H 0.6696 0.4951 0.6326 0.061 Uiso 1 1 calc R . .
C43 C 0.6803(6) 0.3136(11) 0.6647(5) 0.055(3) Uani 1 1 d . . .
H43A H 0.6263 0.3206 0.6988 0.066 Uiso 1 1 calc R . .
H43B H 0.7415 0.3244 0.6912 0.066 Uiso 1 1 calc R . .
C44 C 0.6787(5) 0.1835(10) 0.6294(4) 0.051(3) Uani 1 1 d . . .
H44A H 0.7370 0.1732 0.5995 0.061 Uiso 1 1 calc R . .
H44B H 0.6800 0.1194 0.6668 0.061 Uiso 1 1 calc R . .
C45 C 0.5875(5) 0.1666(9) 0.5831(4) 0.041(3) Uani 1 1 d . . .
H45A H 0.5300 0.1666 0.6144 0.050 Uiso 1 1 calc R . .
H45B H 0.5908 0.0852 0.5594 0.050 Uiso 1 1 calc R . .
C81 C 0.4959(6) 0.3891(12) 0.2812(5) 0.042(3) Uani 1 1 d . . .
C83 C 0.3557(5) 0.3536(10) 0.2102(4) 0.055(3) Uani 1 1 d . . .
H83A H 0.3195 0.4242 0.2288 0.082 Uiso 1 1 calc R . .
H83B H 0.3107 0.2878 0.1970 0.082 Uiso 1 1 calc R . .
H83C H 0.3926 0.3791 0.1682 0.082 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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
C3 O2 C1 124.2(5) . . ?
C81 N8 C7 116.7(9) . . ?
C81 N8 C1 122.4(7) . . ?
C7 N8 C1 119.5(7) . . ?
C81 O82 C83 114.1(8) . . ?
O2 C1 N8 113.0(7) . . ?
O2 C1 C9 107.3(6) . . ?
N8 C1 C9 110.2(7) . . ?
O1 C3 O2 117.4(7) . . ?
O1 C3 C4 120.1(8) . . ?
O2 C3 C4 122.5(6) . . ?
C45 C4 C41 108.3(7) . . ?
C45 C4 C5 111.5(7) . . ?
C41 C4 C5 111.5(7) . . ?
C45 C4 C3 108.2(6) . . ?
C41 C4 C3 106.3(6) . . ?
C5 C4 C3 110.9(6) . . ?
C9 C5 C6 106.3(7) . . ?
C9 C5 C4 108.7(6) . . ?
C6 C5 C4 113.2(8) . . ?
C7 C6 C5 123.8(8) . . ?
C6 C7 N8 120.1(8) . . ?
F1 C9 F2 105.6(7) . . ?
F1 C9 C5 113.5(8) . . ?
F2 C9 C5 110.9(6) . . ?
F1 C9 C1 109.0(7) . . ?
F2 C9 C1 107.5(6) . . ?
C5 C9 C1 110.1(8) . . ?
C42 C41 C4 112.6(7) . . ?
C43 C42 C41 111.7(7) . . ?
C42 C43 C44 110.6(7) . . ?
C45 C44 C43 111.1(7) . . ?
C44 C45 C4 113.6(7) . . ?
O81 C81 O82 125.1(8) . . ?
O81 C81 N8 126.0(9) . . ?
O82 C81 N8 108.9(9) . . ?
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 C3 1.189(8) . ?
O2 C3 1.345(8) . ?
O2 C1 1.413(8) . ?
N8 C81 1.374(10) . ?
N8 C7 1.414(10) . ?
N8 C1 1.429(11) . ?
O81 C81 1.186(11) . ?
O82 C81 1.353(11) . ?
O82 C83 1.434(8) . ?
F1 C9 1.337(10) . ?
F2 C9 1.386(8) . ?
C1 C9 1.533(10) . ?
C3 C4 1.560(9) . ?
C4 C45 1.521(11) . ?
C4 C41 1.537(12) . ?
C4 C5 1.559(10) . ?
C5 C9 1.496(12) . ?
C5 C6 1.501(11) . ?
C6 C7 1.348(10) . ?
C41 C42 1.519(9) . ?
C42 C43 1.482(12) . ?
C43 C44 1.527(13) . ?
C44 C45 1.513(9) . ?
