#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:06:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180287 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/01/7150198.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_7150198
loop_
_publ_author_name
'Griffith, Gerry A.'
'Percy, Jonathan M.'
'Pintat, Stéphane'
'Smith, Clive A.'
'Spencer, Neil'
'Uneyama, Emi'
_publ_section_title
;
 Towards novel difluorinated sugar mimetics; syntheses and
 conformational analyses of highly-functionalised difluorinated
 cyclooctenones.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2701
_journal_page_last               2712
_journal_paper_doi               10.1039/b505978j
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C13 H19 F2 N O4'
_chemical_formula_weight         291.29
_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                 91.5060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5260(9)
_cell_length_b                   7.0680(5)
_cell_length_c                   13.3397(9)
_cell_measurement_reflns_used    6264
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      2.81
_cell_volume                     1369.11(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9518
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absorption correction based on 8283 reflections (SADABS); Rint 0.31
and 0.19 before and after correction respectively.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0323
_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)+(0.0420P)²+0.4613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0818
_reflns_number_gt                2237
_reflns_number_total             2411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b505978j.txt
_cod_data_source_block           16b
_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      P2(1)/c
_cod_database_code               7150198
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.79430(5) 1.19102(11) 0.42852(5) 0.0291(2) Uani 1 1 d . . .
F2 F 0.70637(6) 1.38230(10) 0.34249(6) 0.0329(2) Uani 1 1 d . . .
O1 O 0.71355(6) 0.83032(12) 0.46887(6) 0.0221(2) Uani 1 1 d . . .
O2 O 0.73101(6) 1.01507(13) 0.60617(6) 0.0279(2) Uani 1 1 d . . .
O3 O 0.81654(6) 1.19036(13) 0.21952(7) 0.0297(2) Uani 1 1 d . . .
H3 H 0.7949 1.2832 0.1874 0.045 Uiso 1 1 calc R . .
O4 O 0.57004(7) 1.22810(14) 0.42593(7) 0.0353(3) Uani 1 1 d . . .
N1 N 0.82662(7) 0.76546(15) 0.57982(8) 0.0237(2) Uani 1 1 d . . .
C1 C 0.62598(8) 0.91915(18) 0.45057(9) 0.0233(3) Uani 1 1 d . . .
H1 H 0.5929 0.9203 0.5154 0.028 Uiso 1 1 calc R . .
C2 C 0.57146(9) 0.79221(19) 0.37807(10) 0.0277(3) Uani 1 1 d . . .
H2A H 0.5096 0.8483 0.3671 0.033 Uiso 1 1 calc R . .
H2B H 0.5630 0.6678 0.4106 0.033 Uiso 1 1 calc R . .
C3 C 0.61367(9) 0.75905(19) 0.27567(10) 0.0269(3) Uani 1 1 d . . .
H3A H 0.6800 0.7303 0.2856 0.032 Uiso 1 1 calc R . .
H3B H 0.5840 0.6471 0.2440 0.032 Uiso 1 1 calc R . .
C4 C 0.60345(9) 0.92427(19) 0.20595(10) 0.0274(3) Uani 1 1 d . . .
H4 H 0.5514 0.9243 0.1613 0.033 Uiso 1 1 calc R . .
C5 C 0.66024(9) 1.07014(19) 0.20090(9) 0.0252(3) Uani 1 1 d . . .
H5 H 0.6466 1.1656 0.1526 0.030 Uiso 1 1 calc R . .
C6 C 0.74468(8) 1.09415(18) 0.26659(9) 0.0231(3) Uani 1 1 d . . .
H6 H 0.7676 0.9652 0.2853 0.028 Uiso 1 1 calc R . .
C7 C 0.72068(9) 1.19673(17) 0.36294(10) 0.0237(3) Uani 1 1 d . . .
C8 C 0.63385(8) 1.12281(19) 0.41549(9) 0.0235(3) Uani 1 1 d . . .
C9 C 0.75647(8) 0.88012(17) 0.55693(9) 0.0216(3) Uani 1 1 d . . .
C10 C 0.88333(9) 0.8077(2) 0.66892(10) 0.0305(3) Uani 1 1 d . . .
H10A H 0.9056 0.6873 0.6987 0.037 Uiso 1 1 calc R . .
H10B H 0.8446 0.8710 0.7189 0.037 Uiso 1 1 calc R . .
C11 C 0.96486(11) 0.9314(3) 0.64858(13) 0.0490(4) Uani 1 1 d . . .
H11A H 1.0037 0.8699 0.5992 0.073 Uiso 1 1 calc R . .
H11B H 1.0006 0.9515 0.7110 0.073 Uiso 1 1 calc R . .
H11C H 0.9434 1.0536 0.6222 0.073 Uiso 1 1 calc R . .
C12 C 0.84680(9) 0.59688(18) 0.52039(10) 0.0275(3) Uani 1 1 d . . .
H12A H 0.7882 0.5436 0.4935 0.033 Uiso 1 1 calc R . .
H12B H 0.8758 0.5006 0.5649 0.033 Uiso 1 1 calc R . .
C13 C 0.90937(11) 0.6346(2) 0.43440(11) 0.0371(4) Uani 1 1 d . . .
H13A H 0.8827 0.7343 0.3917 0.056 Uiso 1 1 calc R . .
H13B H 0.9163 0.5187 0.3950 0.056 Uiso 1 1 calc R . .
H13C H 0.9698 0.6754 0.4606 0.056 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
C9 O1 C1 114.70(9) . . ?
C9 N1 C10 118.34(11) . . ?
C9 N1 C12 122.28(11) . . ?
C10 N1 C12 119.37(11) . . ?
O1 C1 C8 113.19(10) . . ?
O1 C1 C2 107.09(10) . . ?
C8 C1 C2 113.84(10) . . ?
C1 C2 C3 116.26(11) . . ?
C4 C3 C2 113.54(11) . . ?
C5 C4 C3 125.97(12) . . ?
C4 C5 C6 124.08(12) . . ?
O3 C6 C5 113.53(10) . . ?
O3 C6 C7 109.58(10) . . ?
C5 C6 C7 110.20(10) . . ?
F2 C7 F1 105.75(10) . . ?
F2 C7 C6 109.15(10) . . ?
F1 C7 C6 109.51(10) . . ?
F2 C7 C8 107.16(10) . . ?
F1 C7 C8 109.48(10) . . ?
C6 C7 C8 115.34(10) . . ?
O4 C8 C1 119.17(12) . . ?
O4 C8 C7 118.94(12) . . ?
C1 C8 C7 121.84(10) . . ?
O2 C9 N1 126.39(11) . . ?
O2 C9 O1 121.85(11) . . ?
N1 C9 O1 111.77(11) . . ?
N1 C10 C11 113.75(12) . . ?
N1 C12 C13 113.67(11) . . ?
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
F1 C7 1.3643(14) . ?
F2 C7 1.3546(14) . ?
O1 C9 1.3616(14) . ?
O1 C1 1.4337(15) . ?
O2 C9 1.2209(15) . ?
O3 C6 1.4074(15) . ?
O4 C8 1.1997(16) . ?
N1 C9 1.3311(16) . ?
N1 C10 1.4592(16) . ?
N1 C12 1.4651(17) . ?
C1 C8 1.5189(18) . ?
C1 C2 1.5255(18) . ?
C2 C3 1.5299(19) . ?
C3 C4 1.4979(19) . ?
C4 C5 1.3232(19) . ?
C5 C6 1.4983(17) . ?
C6 C7 1.5240(18) . ?
C7 C8 1.5498(18) . ?
C10 C11 1.503(2) . ?
C12 C13 1.506(2) . ?
