#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/33/7103338.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_7103338
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 N1 O4'
_chemical_formula_sum            'C14 H17 F2 N O4'
_chemical_formula_weight         301.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             07-06-13
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90.285(8)
_cell_angle_beta                 106.596(9)
_cell_angle_gamma                102.27(1)
_cell_formula_units_Z            2
_cell_length_a                   8.0326(8)
_cell_length_b                   8.7779(11)
_cell_length_c                   10.5283(10)
_cell_measurement_reflns_used    77
_cell_measurement_temperature    250
_cell_measurement_theta_max      22
_cell_measurement_theta_min      4
_cell_volume                     693.44(14)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      250
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12967
_diffrn_reflns_theta_full        26.396
_diffrn_reflns_theta_max         29.996
_diffrn_reflns_theta_min         2.023
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       92
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0868
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000320
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
1.00 0.648 0.633
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0709
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0486
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2520
_reflns_number_total             3998
_reflns_threshold_expression     I>3.0σ(I)
_cod_data_source_file            b807092j.txt
_cod_data_source_block           Patrick
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'refu' changed to
'refU' 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 -1 '
_cod_original_formula_sum        'C14 H17 F2 N1 O4'
_cod_database_code               7103338
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.19770(17) 0.45744(16) 0.71380(14) 0.0264 1.0000 Uani . . . . . .
C3 C 0.14237(18) 0.69957(18) 0.60262(14) 0.0290 1.0000 Uani . . . . . .
C4 C 0.09799(17) 0.76733(16) 0.72152(13) 0.0243 1.0000 Uani . . . . . .
C5 C 0.14894(17) 0.67023(15) 0.84579(13) 0.0233 1.0000 Uani . . . . . .
C6 C 0.34721(18) 0.69991(16) 0.91018(13) 0.0271 1.0000 Uani . . . . . .
C7 C 0.45506(17) 0.61626(17) 0.88368(14) 0.0284 1.0000 Uani . . . . . .
C8 C 0.50256(18) 0.41159(18) 0.75203(15) 0.0308 1.0000 Uani . . . . . .
C9 C 0.08525(17) 0.49644(15) 0.79940(14) 0.0249 1.0000 Uani . . . . . .
C10 C 0.5253(3) 0.2084(3) 0.6142(3) 0.0647 1.0000 Uani . . . . . .
C11 C 0.1993(2) 0.94262(17) 0.74970(15) 0.0320 1.0000 Uani . . . . . .
C12 C 0.1395(3) 1.03182(18) 0.84745(17) 0.0402 1.0000 Uani . . . . . .
C13 C -0.0608(3) 1.0245(2) 0.79745(19) 0.0433 1.0000 Uani . . . . . .
C14 C -0.1666(2) 0.8534(2) 0.77115(18) 0.0395 1.0000 Uani . . . . . .
C15 C -0.10669(19) 0.76158(19) 0.67303(15) 0.0321 1.0000 Uani . . . . . .
O1 O 0.14025(19) 0.76957(17) 0.50300(12) 0.0462 1.0000 Uani . . . . . .
O2 O 0.17811(14) 0.55441(13) 0.60054(10) 0.0323 1.0000 Uani . . . . . .
O3 O 0.66284(15) 0.44999(16) 0.79886(13) 0.0448 1.0000 Uani . . . . . .
O4 O 0.41414(15) 0.29310(15) 0.65972(13) 0.0421 1.0000 Uani . . . . . .
N8 N 0.38411(15) 0.48507(14) 0.78910(12) 0.0276 1.0000 Uani . . . . . .
F1 F 0.41681(14) 0.82092(11) 1.00606(10) 0.0429 1.0000 Uani . . . . . .
F2 F 0.10856(12) 0.40293(10) 0.90806(9) 0.0347 1.0000 Uani . . . . . .
H11 H 0.1544 0.3449 0.6805 0.0494(14) 1.0000 Uiso . . . . . .
H51 H 0.0892 0.6948 0.9122 0.0494(14) 1.0000 Uiso . . . . . .
H71 H 0.5859 0.6456 0.9302 0.0494(14) 1.0000 Uiso . . . . . .
H91 H -0.0433 0.4737 0.7462 0.0494(14) 1.0000 Uiso . . . . . .
H101 H 0.4482 0.1232 0.5462 0.0494(14) 1.0000 Uiso . . . . . .
H102 H 0.5982 0.1619 0.6911 0.0494(14) 1.0000 Uiso . . . . . .
H103 H 0.6062 0.2818 0.5738 0.0494(14) 1.0000 Uiso . . . . . .
H111 H 0.3297 0.9472 0.7875 0.0494(14) 1.0000 Uiso . . . . . .
H112 H 0.1777 0.9943 0.6639 0.0494(14) 1.0000 Uiso . . . . . .
H121 H 0.2055 1.1436 0.8585 0.0494(14) 1.0000 Uiso . . . . . .
H122 H 0.1672 0.9845 0.9351 0.0494(14) 1.0000 Uiso . . . . . .
H131 H -0.0970 1.0780 0.8660 0.0494(14) 1.0000 Uiso . . . . . .
H132 H -0.0876 1.0787 0.7131 0.0494(14) 1.0000 Uiso . . . . . .
H141 H -0.1473 0.8021 0.8571 0.0494(14) 1.0000 Uiso . . . . . .
H142 H -0.2962 0.8517 0.7328 0.0494(14) 1.0000 Uiso . . . . . .
H151 H -0.1355 0.8078 0.5849 0.0494(14) 1.0000 Uiso . . . . . .
H152 H -0.1732 0.6500 0.6633 0.0494(14) 1.0000 Uiso . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 . C1 . O2 . 109.22(10) ?
C9 . C1 . N8 . 111.21(11) ?
O2 . C1 . N8 . 109.16(11) ?
C9 . C1 . H11 . 109.1 no
O2 . C1 . H11 . 109.1 no
N8 . C1 . H11 . 109.1 no
C4 . C3 . O1 . 121.96(13) ?
C4 . C3 . O2 . 121.99(12) ?
O1 . C3 . O2 . 115.99(13) ?
C3 . C4 . C5 . 110.72(11) ?
C3 . C4 . C11 . 107.82(11) ?
C5 . C4 . C11 . 112.15(11) ?
C3 . C4 . C15 . 105.81(11) ?
C5 . C4 . C15 . 111.98(11) ?
C11 . C4 . C15 . 108.07(11) ?
C4 . C5 . C6 . 112.64(11) ?
C4 . C5 . C9 . 108.15(11) ?
C6 . C5 . C9 . 106.93(11) ?
C4 . C5 . H51 . 109.7 no
C6 . C5 . H51 . 109.7 no
C9 . C5 . H51 . 109.7 no
C5 . C6 . C7 . 125.39(12) ?
C5 . C6 . F1 . 115.52(12) ?
C7 . C6 . F1 . 119.06(12) ?
C6 . C7 . N8 . 120.01(12) ?
C6 . C7 . H71 . 120.0 no
N8 . C7 . H71 . 120.0 no
O3 . C8 . O4 . 125.53(14) ?
O3 . C8 . N8 . 123.65(15) ?
O4 . C8 . N8 . 110.82(12) ?
C5 . C9 . C1 . 108.49(11) ?
C5 . C9 . F2 . 110.97(11) ?
C1 . C9 . F2 . 107.86(10) ?
C5 . C9 . H91 . 109.8 no
C1 . C9 . H91 . 109.8 no
F2 . C9 . H91 . 109.8 no
O4 . C10 . H101 . 109.5 no
O4 . C10 . H102 . 109.5 no
H101 . C10 . H102 . 109.5 no
O4 . C10 . H103 . 109.5 no
H101 . C10 . H103 . 109.5 no
H102 . C10 . H103 . 109.5 no
C4 . C11 . C12 . 112.98(12) ?
C4 . C11 . H111 . 108.6 no
C12 . C11 . H111 . 108.6 no
C4 . C11 . H112 . 108.6 no
C12 . C11 . H112 . 108.6 no
H111 . C11 . H112 . 109.5 no
C11 . C12 . C13 . 111.20(15) ?
C11 . C12 . H121 . 109.0 no
C13 . C12 . H121 . 109.0 no
C11 . C12 . H122 . 109.0 no
C13 . C12 . H122 . 109.0 no
H121 . C12 . H122 . 109.5 no
C12 . C13 . C14 . 110.47(13) ?
C12 . C13 . H131 . 109.2 no
C14 . C13 . H131 . 109.2 no
C12 . C13 . H132 . 109.2 no
C14 . C13 . H132 . 109.2 no
H131 . C13 . H132 . 109.5 no
C13 . C14 . C15 . 111.53(13) ?
C13 . C14 . H141 . 109.0 no
C15 . C14 . H141 . 109.0 no
C13 . C14 . H142 . 109.0 no
C15 . C14 . H142 . 109.0 no
H141 . C14 . H142 . 109.5 no
C14 . C15 . C4 . 112.27(13) ?
C14 . C15 . H151 . 108.8 no
C4 . C15 . H151 . 108.8 no
C14 . C15 . H152 . 108.8 no
C4 . C15 . H152 . 108.8 no
H151 . C15 . H152 . 109.5 no
C1 . O2 . C3 . 123.79(10) ?
C10 . O4 . C8 . 115.31(14) ?
C1 . N8 . C7 . 117.93(11) ?
C1 . N8 . C8 . 122.00(12) ?
C7 . N8 . C8 . 118.44(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C9 . 1.5293(18) ?
C1 . O2 . 1.4598(17) ?
C1 . N8 . 1.4474(17) ?
C1 . H11 . 1.000 no
C3 . C4 . 1.5446(19) ?
C3 . O1 . 1.2160(17) ?
C3 . O2 . 1.3657(18) ?
C4 . C5 . 1.5682(18) ?
C4 . C11 . 1.563(2) ?
C4 . C15 . 1.5656(19) ?
C5 . C6 . 1.5063(19) ?
C5 . C9 . 1.5315(19) ?
C5 . H51 . 1.000 no
C6 . C7 . 1.332(2) ?
C6 . F1 . 1.3691(16) ?
C7 . N8 . 1.4240(19) ?
C7 . H71 . 1.000 no
C8 . O3 . 1.2106(18) ?
C8 . O4 . 1.346(2) ?
C8 . N8 . 1.3943(17) ?
C9 . F2 . 1.4035(16) ?
C9 . H91 . 1.000 no
C10 . O4 . 1.450(2) ?
C10 . H101 . 1.000 no
C10 . H102 . 1.000 no
C10 . H103 . 1.000 no
C11 . C12 . 1.529(2) ?
C11 . H111 . 1.000 no
C11 . H112 . 1.000 no
C12 . C13 . 1.530(3) ?
C12 . H121 . 1.000 no
C12 . H122 . 1.000 no
C13 . C14 . 1.541(3) ?
C13 . H131 . 1.000 no
C13 . H132 . 1.000 no
C14 . C15 . 1.546(2) ?
C14 . H141 . 1.000 no
C14 . H142 . 1.000 no
C15 . H151 . 1.000 no
C15 . H152 . 1.000 no
