#------------------------------------------------------------------------------
#$Date: 2018-10-05 14:19:55 +0200 (vie 05 de oct de 2018) $
#$Revision: 211332 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/22/4022268.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_4022268
loop_
_publ_author_name
'Alan Armstrong'
'Ghafoor Ahmed'
'Belén Domínguez-Fernández'
'Barry R. Hayter'
'J. Steven Wailes'
_publ_section_title
;
 Enantioselective Epoxidation of Alkenes Catalyzed by
 2-Fluoro-N-Carbethoxytropinone and Related Tropinone Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8610
_journal_page_last               8617
_journal_paper_doi               10.1021/jo026322y
_journal_volume                  67
_journal_year                    2002
_chemical_formula_moiety         'C10 H14 F N O3'
_chemical_formula_sum            'C10 H14 F N O3'
_chemical_formula_weight         215.22
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.439(2)
_cell_length_b                   7.680(2)
_cell_length_c                   20.619(5)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      17.20
_cell_measurement_theta_min      12.65
_cell_volume                     1019.7(4)
_computing_cell_refinement       'STADI4 (Stoe & Cie, 1997a)'
_computing_data_collection       'STADI4 (Stoe & Cie, 1997a)'
_computing_data_reduction        'X-RED (Stoe & Cie, 1997b)'
_computing_molecular_graphics    'SHELXTL/PC version 5.03 (Sheldrick, 1995)'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Stoe Stadi-4 four-circle'
_diffrn_measurement_method       ω-θ
_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  0.018
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            2190
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.83
_diffrn_standards_decay_%        'variation +/-3.8'
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.14
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.043P)²+0.257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                1702
_reflns_number_total             1795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026322y_s2.cif
_cod_data_source_block           DICYNF
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geometrically placed' was
changed to 'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_database_code               4022268
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
F1 F 1.0073(2) 0.4552(2) 0.20152(6) 0.0512(5) Uani 1 1 d .
O1 O 1.3182(3) 0.6897(2) 0.12214(9) 0.0505(5) Uani 1 1 d .
O2 O 0.9229(3) 0.04324(19) 0.09427(7) 0.0334(4) Uani 1 1 d .
O3 O 0.6744(2) 0.18637(19) 0.15098(7) 0.0297(4) Uani 1 1 d .
C1 C 0.8151(3) 0.5058(2) 0.10516(10) 0.0262(5) Uani 1 1 d .
H1 H 0.6765 0.5053 0.1270 0.031 Uiso 1 1 calc R
C2 C 0.9857(3) 0.5719(3) 0.14945(10) 0.0337(5) Uani 1 1 d .
H2 H 0.9517 0.6913 0.1657 0.040 Uiso 1 1 calc R
C3 C 1.1968(3) 0.5718(3) 0.11478(11) 0.0319(5) Uani 1 1 d .
C4 C 1.2381(3) 0.4174(3) 0.07196(11) 0.0319(5) Uani 1 1 d .
H4A H 1.2885 0.3191 0.0988 0.038 Uiso 1 1 calc R
H4B H 1.3482 0.4471 0.0403 0.038 Uiso 1 1 calc R
C5 C 1.0418(3) 0.3619(3) 0.03554(9) 0.0244(5) Uani 1 1 d .
H5 H 1.0674 0.2557 0.0086 0.029 Uiso 1 1 calc R
C6 C 0.9526(4) 0.5103(3) -0.00534(10) 0.0318(5) Uani 1 1 d .
H6A H 0.8699 0.4642 -0.0420 0.038 Uiso 1 1 calc R
H6B H 1.0649 0.5850 -0.0227 0.038 Uiso 1 1 calc R
C7 C 0.8136(3) 0.6131(3) 0.04230(11) 0.0323(5) Uani 1 1 d .
H7A H 0.8706 0.7311 0.0499 0.039 Uiso 1 1 calc R
H7B H 0.6707 0.6242 0.0251 0.039 Uiso 1 1 calc R
N8 N 0.8743(3) 0.3332(2) 0.08196(8) 0.0230(4) Uani 1 1 d .
C9 C 0.8339(3) 0.1763(3) 0.10868(10) 0.0237(4) Uani 1 1 d .
C10 C 0.6170(4) 0.0234(3) 0.18200(10) 0.0333(5) Uani 1 1 d .
H10A H 0.7296 -0.0166 0.2111 0.040 Uiso 1 1 calc R
H10B H 0.5918 -0.0677 0.1489 0.040 Uiso 1 1 calc R
C11 C 0.4223(5) 0.0575(4) 0.22022(13) 0.0549(8) Uani 1 1 d .
H11A H 0.3071 0.0803 0.1904 0.082 Uiso 1 1 calc R
H11B H 0.4433 0.1589 0.2483 0.082 Uiso 1 1 calc R
H11C H 0.3897 -0.0446 0.2469 0.082 Uiso 1 1 calc 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 0.0401(8) 0.0830(12) 0.0305(6) -0.0047(7) -0.0003(6) -0.0014(9)
O1 0.0295(8) 0.0462(10) 0.0758(13) -0.0224(10) 0.0020(9) -0.0093(9)
O2 0.0363(8) 0.0214(7) 0.0424(8) -0.0002(7) 0.0061(7) 0.0040(7)
O3 0.0295(7) 0.0272(7) 0.0324(7) 0.0055(6) 0.0075(6) -0.0025(7)
C1 0.0189(9) 0.0216(10) 0.0381(11) -0.0056(9) 0.0051(10) 0.0009(9)
C2 0.0276(11) 0.0354(11) 0.0381(11) -0.0131(10) 0.0036(10) 0.0004(11)
C3 0.0206(10) 0.0343(11) 0.0406(11) -0.0088(11) -0.0040(9) -0.0006(10)
C4 0.0202(10) 0.0335(11) 0.0420(11) -0.0083(11) 0.0023(9) 0.0025(9)
C5 0.0225(10) 0.0216(9) 0.0291(10) -0.0036(8) 0.0063(8) -0.0026(9)
C6 0.0335(11) 0.0280(10) 0.0340(10) 0.0046(9) 0.0015(10) -0.0098(10)
C7 0.0241(10) 0.0247(10) 0.0481(12) 0.0065(10) -0.0010(10) -0.0008(9)
N8 0.0232(8) 0.0196(8) 0.0263(8) -0.0018(7) 0.0058(7) 0.0006(7)
C9 0.0221(9) 0.0250(10) 0.0239(9) -0.0007(8) -0.0028(9) -0.0018(9)
C10 0.0399(12) 0.0292(10) 0.0307(10) 0.0077(9) 0.0005(10) -0.0068(10)
C11 0.0666(19) 0.0437(14) 0.0545(14) 0.0088(13) 0.0323(14) -0.0102(16)
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
C9 O3 C10 115.37(16)
N8 C1 C2 108.21(17)
N8 C1 C7 102.26(16)
C2 C1 C7 109.48(17)
F1 C2 C1 108.56(18)
F1 C2 C3 105.52(18)
C1 C2 C3 111.14(16)
O1 C3 C4 123.5(2)
O1 C3 C2 121.0(2)
C4 C3 C2 115.50(19)
C3 C4 C5 111.21(17)
N8 C5 C6 101.32(16)
N8 C5 C4 109.32(15)
C6 C5 C4 111.90(17)
C5 C6 C7 104.36(16)
C1 C7 C6 104.98(16)
C9 N8 C5 122.99(17)
C9 N8 C1 128.81(15)
C5 N8 C1 105.71(16)
O2 C9 O3 124.64(19)
O2 C9 N8 124.27(18)
O3 C9 N8 111.02(17)
O3 C10 C11 107.02(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.406(3)
O1 C3 1.205(3)
O2 C9 1.208(2)
O3 C9 1.349(2)
O3 C10 1.454(2)
C1 N8 1.460(2)
C1 C2 1.516(3)
C1 C7 1.536(3)
C2 C3 1.536(3)
C3 C4 1.503(3)
C4 C5 1.531(3)
C5 N8 1.459(2)
C5 C6 1.529(3)
C6 C7 1.546(3)
N8 C9 1.351(3)
C10 C11 1.504(4)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N8 C1 C2 F1 -59.7(2)
C7 C1 C2 F1 -170.40(16)
N8 C1 C2 C3 55.9(2)
C7 C1 C2 C3 -54.8(2)
F1 C2 C3 O1 -102.7(3)
C1 C2 C3 O1 139.9(2)
F1 C2 C3 C4 77.5(2)
C1 C2 C3 C4 -39.9(3)
O1 C3 C4 C5 -141.3(2)
C2 C3 C4 C5 38.5(3)
C3 C4 C5 N8 -54.0(2)
C3 C4 C5 C6 57.4(2)
N8 C5 C6 C7 30.73(19)
C4 C5 C6 C7 -85.6(2)
N8 C1 C7 C6 -21.5(2)
C2 C1 C7 C6 93.04(19)
C5 C6 C7 C1 -5.7(2)
C6 C5 N8 C9 149.79(18)
C4 C5 N8 C9 -92.0(2)
C6 C5 N8 C1 -46.71(19)
C4 C5 N8 C1 71.5(2)
C2 C1 N8 C9 89.7(2)
C7 C1 N8 C9 -154.8(2)
C2 C1 N8 C5 -72.46(19)
C7 C1 N8 C5 43.06(19)
C10 O3 C9 O2 2.5(3)
C10 O3 C9 N8 179.36(17)
C5 N8 C9 O2 -4.5(3)
C1 N8 C9 O2 -164.0(2)
C5 N8 C9 O3 178.60(16)
C1 N8 C9 O3 19.1(3)
C9 O3 C10 C11 -173.06(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9260331
