#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:08:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180289 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/03/7150336.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_7150336
loop_
_publ_author_name
'Arany, Andrea'
'Crowley, Patrick J.'
'Fawcett, John'
'Hursthouse, Michael B.'
'Kariuki, Benson M.'
'Light, Mark E.'
'Moralee, Andrew C.'
'Percy, Jonathan M.'
'Salafia, Vittoria'
_publ_section_title
;
 Highly-functionalised difluorinated (hydroxymethyl)conduritol
 analogues via the Diels-Alder reactions of a difluorinated dienophile.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              455
_journal_page_last               465
_journal_paper_doi               10.1039/b314314g
_journal_volume                  2
_journal_year                    2004
_chemical_formula_sum            'C15 H21 F2 N O5'
_chemical_formula_weight         333.33
_chemical_name_systematic
;
?
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.346(10)
_cell_angle_beta                 96.497(9)
_cell_angle_gamma                91.913(10)
_cell_formula_units_Z            2
_cell_length_a                   6.951(4)
_cell_length_b                   8.869(5)
_cell_length_c                   13.399(7)
_cell_measurement_reflns_used    533
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18.47
_cell_measurement_theta_min      2.32
_cell_volume                     811.0(8)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1077
_diffrn_reflns_av_sigmaI/netI    0.1633
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5929
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.887
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.887
_refine_ls_R_factor_all          0.1780
_refine_ls_R_factor_gt           0.0718
_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)+(0.0598P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1912
_reflns_number_gt                1140
_reflns_number_total             2833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b314314g.txt
_cod_data_source_block           13b
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150336
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_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 0.4924(4) 0.7849(3) 0.9204(2) 0.0670(9) Uani 1 1 d . C .
F2 F 0.4071(4) 0.9717(3) 0.8438(2) 0.0650(9) Uani 1 1 d . C .
N1 N 0.4590(7) 0.4202(5) 0.7724(4) 0.0768(16) Uani 1 1 d . . .
O1 O 0.8137(5) 1.0081(4) 0.8204(3) 0.0565(10) Uani 1 1 d . C .
O2 O 0.4676(5) 0.9526(5) 0.6514(3) 0.0739(12) Uani 1 1 d . C .
O3 O 0.5202(6) 0.7123(4) 0.5900(3) 0.0773(13) Uani 1 1 d . B .
O4 O 0.6209(5) 0.6333(4) 0.7627(2) 0.0481(9) Uani 1 1 d . . .
O5 O 0.2955(5) 0.6274(4) 0.7417(3) 0.0760(13) Uani 1 1 d . . .
C1 C 0.8393(8) 0.8571(6) 0.7754(4) 0.0552(15) Uani 1 1 d . . .
C2 C 0.6207(7) 0.7918(6) 0.7605(4) 0.0452(13) Uani 1 1 d . C .
C3 C 0.5574(8) 0.8830(6) 0.8601(4) 0.0498(14) Uani 1 1 d . . .
C4 C 0.7356(8) 0.9732(6) 0.9079(4) 0.0593(15) Uani 1 1 d . C .
H4 H 0.7152 1.0631 0.9593 0.071 Uiso 1 1 calc R . .
C5 C 0.8738(8) 0.8605(6) 0.9451(4) 0.0628(16) Uani 1 1 d . . .
H5 H 0.9083 0.8448 1.0133 0.075 Uiso 1 1 calc R C .
C6 C 0.9359(8) 0.7891(6) 0.8641(4) 0.0572(15) Uani 1 1 d . C .
H6 H 1.0246 0.7098 0.8612 0.069 Uiso 1 1 calc R . .
C7 C 0.9366(8) 0.8469(6) 0.6825(4) 0.0759(18) Uani 1 1 d . C .
H7A H 0.8623 0.8996 0.6326 0.114 Uiso 1 1 calc R . .
H7B H 0.9445 0.7394 0.6539 0.114 Uiso 1 1 calc R . .
H7C H 1.0676 0.8948 0.6993 0.114 Uiso 1 1 calc R . .
C8 C 0.5194(7) 0.8290(7) 0.6628(4) 0.0534(14) Uani 1 1 d . . .
C9 C 0.4418(13) 0.7351(10) 0.4878(5) 0.126(3) Uani 1 1 d . . .
H9A H 0.5008 0.8306 0.4720 0.151 Uiso 1 1 calc R A 1
H9B H 0.4769 0.6497 0.4381 0.151 Uiso 1 1 calc R A 1
C10 C 0.247(3) 0.7431(19) 0.4782(17) 0.089(6) Uani 0.50 1 d P B 1
H10A H 0.1873 0.6464 0.4898 0.133 Uiso 0.50 1 d PR B 1
H10B H 0.2008 0.7625 0.4096 0.133 Uiso 0.50 1 d PR B 1
H10C H 0.2112 0.8262 0.5282 0.133 Uiso 0.50 1 d PR B 1
C10' C 0.230(3) 0.627(2) 0.4713(16) 0.134(10) Uani 0.50 1 d P B 2
H10D H 0.1401 0.6762 0.5156 0.201 Uiso 0.50 1 d PR B 2
H10E H 0.2560 0.5257 0.4886 0.201 Uiso 0.50 1 d PR B 2
H10F H 0.1726 0.6179 0.4003 0.201 Uiso 0.50 1 d PR B 2
C11 C 0.4424(9) 0.5620(6) 0.7575(4) 0.0592(15) Uani 1 1 d . C .
C12 C 0.6411(8) 0.3531(6) 0.7997(4) 0.0648(17) Uani 1 1 d . C .
H12A H 0.7397 0.3881 0.7592 0.078 Uiso 1 1 calc R . .
H12B H 0.6241 0.2407 0.7828 0.078 Uiso 1 1 calc R . .
C13 C 0.7122(9) 0.3946(7) 0.9101(5) 0.083(2) Uani 1 1 d . . .
H13A H 0.7385 0.5053 0.9263 0.125 Uiso 1 1 calc R C .
H13B H 0.8316 0.3426 0.9260 0.125 Uiso 1 1 calc R . .
H13C H 0.6133 0.3632 0.9506 0.125 Uiso 1 1 calc R . .
C14 C 0.279(4) 0.340(3) 0.795(2) 0.076(6) Uani 0.50 1 d P C 1
H14A H 0.3153 0.2737 0.8466 0.091 Uiso 0.50 1 calc PR C 1
H14B H 0.1930 0.4170 0.8239 0.091 Uiso 0.50 1 calc PR C 1
C15 C 0.175(2) 0.2501(16) 0.7088(15) 0.095(7) Uani 0.50 1 d P C 1
H15A H 0.1620 0.3082 0.6518 0.142 Uiso 0.50 1 d PR C 1
H15B H 0.0459 0.2217 0.7251 0.142 Uiso 0.50 1 d PR C 1
H15C H 0.2442 0.1576 0.6902 0.142 Uiso 0.50 1 d PR C 1
C14' C 0.283(3) 0.312(2) 0.7306(14) 0.078(6) Uani 0.50 1 d P C 2
H14C H 0.1959 0.3517 0.6781 0.093 Uiso 0.50 1 calc PR C 2
H14D H 0.3204 0.2078 0.7043 0.093 Uiso 0.50 1 calc PR C 2
C15' C 0.203(4) 0.318(3) 0.827(2) 0.089(7) Uani 0.50 1 d P C 2
H15D H 0.3002 0.2883 0.8782 0.134 Uiso 0.50 1 d PR C 2
H15E H 0.0885 0.2484 0.8177 0.134 Uiso 0.50 1 d PR C 2
H15F H 0.1666 0.4226 0.8489 0.134 Uiso 0.50 1 d PR C 2
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
C11 N1 C12 124.5(5) . . ?
C11 N1 C14 116.0(10) . . ?
C12 N1 C14 116.6(10) . . ?
C11 N1 C14' 115.8(9) . . ?
C12 N1 C14' 117.6(8) . . ?
C14 N1 C14' 33.1(11) . . ?
C1 O1 C4 97.8(4) . . ?
C8 O3 C9 116.8(5) . . ?
C11 O4 C2 115.2(4) . . ?
O1 C1 C7 113.9(5) . . ?
O1 C1 C6 102.0(4) . . ?
C7 C1 C6 117.9(5) . . ?
O1 C1 C2 99.6(4) . . ?
C7 C1 C2 115.9(4) . . ?
C6 C1 C2 105.1(4) . . ?
O4 C2 C8 112.3(4) . . ?
O4 C2 C3 112.5(4) . . ?
C8 C2 C3 115.5(4) . . ?
O4 C2 C1 108.2(4) . . ?
C8 C2 C1 109.6(4) . . ?
C3 C2 C1 97.4(4) . . ?
F2 C3 F1 103.9(4) . . ?
F2 C3 C4 112.1(4) . . ?
F1 C3 C4 112.7(4) . . ?
F2 C3 C2 114.1(4) . . ?
F1 C3 C2 110.5(4) . . ?
C4 C3 C2 103.7(4) . . ?
O1 C4 C3 100.3(4) . . ?
O1 C4 C5 102.4(4) . . ?
C3 C4 C5 106.2(4) . . ?
C6 C5 C4 105.5(5) . . ?
C5 C6 C1 106.5(5) . . ?
O2 C8 O3 125.5(5) . . ?
O2 C8 C2 123.9(5) . . ?
O3 C8 C2 110.1(5) . . ?
C10 C9 O3 112.0(11) . . ?
C10 C9 C10' 36.8(10) . . ?
O3 C9 C10' 101.1(9) . . ?
O5 C11 N1 127.7(6) . . ?
O5 C11 O4 121.9(5) . . ?
N1 C11 O4 110.4(5) . . ?
N1 C12 C13 112.2(5) . . ?
C15 C14 N1 114(2) . . ?
C15' C14' N1 95.5(19) . . ?
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 C3 1.369(5) . ?
F2 C3 1.346(5) . ?
N1 C11 1.309(6) . ?
N1 C12 1.449(6) . ?
N1 C14 1.50(2) . ?
N1 C14' 1.53(2) . ?
O1 C1 1.412(5) . ?
O1 C4 1.416(6) . ?
O2 C8 1.190(6) . ?
O3 C8 1.315(6) . ?
O3 C9 1.460(6) . ?
O4 C11 1.364(6) . ?
O4 C2 1.410(5) . ?
O5 C11 1.204(6) . ?
C1 C7 1.475(7) . ?
C1 C6 1.511(7) . ?
C1 C2 1.588(7) . ?
C2 C8 1.500(7) . ?
C2 C3 1.572(7) . ?
C3 C4 1.480(7) . ?
C4 C5 1.507(7) . ?
C5 C6 1.300(7) . ?
C9 C10 1.35(2) . ?
C9 C10' 1.70(2) . ?
C12 C13 1.494(7) . ?
C14 C15 1.41(4) . ?
C14' C15' 1.45(3) . ?
