#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/71/1507111.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_1507111
loop_
_publ_author_name
'Fawcett, John'
'Griffith, Gerry A.'
'Percy, Jonathan M.'
'Uneyama, Emi'
_publ_section_title
;
 Unexpectedly selective formation and reactions of epoxycyclooctenones
 under microwave-mediated conditions.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1277
_journal_page_last               1280
_journal_paper_doi               10.1021/ol0496327
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C15 H26 F2 N2 O5'
_chemical_formula_weight         352.38
_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
_cell_angle_alpha                104.018(2)
_cell_angle_beta                 103.538(2)
_cell_angle_gamma                96.314(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9296(10)
_cell_length_b                   10.4369(14)
_cell_length_c                   12.3706(17)
_cell_measurement_reflns_used    2540
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.30
_cell_volume                     830.6(2)
_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 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_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            5010
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0534P)²+0.2057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                2443
_reflns_number_total             2863
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0496327si20040301_101728.cif
_cod_data_source_block           10c_audit_creation_method_SHELXL-97
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1507111
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
F1 F 0.27207(15) 0.71262(10) 0.42160(8) 0.0251(3) Uani 1 1 d .
F2 F 0.21028(15) 0.59582(9) 0.53457(9) 0.0254(3) Uani 1 1 d .
N2 N 0.2419(2) 0.51557(16) 0.77730(14) 0.0296(4) Uani 1 1 d .
O5 O 0.16174(19) 1.05467(13) 0.64120(11) 0.0263(3) Uani 1 1 d .
H5 H 0.1176 1.1009 0.5994 0.056(8) Uiso 1 1 calc R
O1 O -0.03283(17) 0.79035(13) 0.50015(11) 0.0244(3) Uani 1 1 d .
H1 H -0.1120 0.7531 0.5276 0.037 Uiso 1 1 calc R
N1 N 0.6248(2) 0.67221(14) 0.53742(13) 0.0210(3) Uani 1 1 d .
H1C H 0.5620 0.6418 0.4640 0.025 Uiso 1 1 d R
H1B H 0.6286 0.6040 0.5617 0.025 Uiso 1 1 d R
O2 O 0.41031(18) 0.69891(12) 0.75788(11) 0.0223(3) Uani 1 1 d .
O3 O 0.5221(2) 0.50344(13) 0.71566(12) 0.0334(3) Uani 1 1 d .
O4 O 0.57302(17) 0.88638(11) 0.58500(10) 0.0194(3) Uani 1 1 d .
C1 C 0.1607(2) 0.82088(17) 0.57676(15) 0.0196(4) Uani 1 1 d .
H1A H 0.1509 0.8179 0.6539 0.023 Uiso 1 1 calc R
C2 C 0.2868(3) 0.72141(17) 0.53502(15) 0.0197(4) Uani 1 1 d .
C3 C 0.5142(3) 0.75808(17) 0.59705(15) 0.0190(4) Uani 1 1 d .
C4 C 0.5756(3) 0.75993(17) 0.72611(15) 0.0208(4) Uani 1 1 d .
H4 H 0.6831 0.7067 0.7366 0.025 Uiso 1 1 calc R
C5 C 0.6564(3) 0.90047(18) 0.80830(15) 0.0221(4) Uani 1 1 d .
C5' C 0.6652(3) 0.8977(2) 0.93085(16) 0.0311(5) Uani 1 1 d .
H5'1 H 0.7285 0.9842 0.9830 0.047 Uiso 1 1 calc R
H5'2 H 0.7417 0.8312 0.9501 0.047 Uiso 1 1 calc R
H5'3 H 0.5309 0.8761 0.9373 0.047 Uiso 1 1 calc R
C5" C 0.8703(3) 0.94589(19) 0.80401(17) 0.0290(4) Uani 1 1 d .
H5"1 H 0.9214 1.0348 0.8548 0.044 Uiso 1 1 calc R
H5"2 H 0.8696 0.9461 0.7263 0.044 Uiso 1 1 calc R
H5"3 H 0.9550 0.8855 0.8282 0.044 Uiso 1 1 calc R
C6 C 0.5197(3) 0.99529(18) 0.77272(15) 0.0227(4) Uani 1 1 d .
H6A H 0.5813 1.0865 0.8178 0.027 Uiso 1 1 calc R
H6B H 0.3924 0.9743 0.7900 0.027 Uiso 1 1 calc R
C7 C 0.4796(3) 0.98664(17) 0.64437(15) 0.0203(4) Uani 1 1 d .
H7 H 0.5384 1.0735 0.6382 0.024 Uiso 1 1 calc R
C8 C 0.2576(3) 0.95995(17) 0.58249(15) 0.0205(4) Uani 1 1 d .
H8 H 0.2415 0.9678 0.5036 0.025 Uiso 1 1 calc R
C9 C 0.3991(3) 0.56559(18) 0.74782(15) 0.0246(4) Uani 1 1 d .
C10 C 0.0885(3) 0.5910(2) 0.8060(2) 0.0432(6) Uani 1 1 d .
H10A H -0.0407 0.5310 0.7794 0.052 Uiso 1 1 calc R
H10B H 0.0790 0.6594 0.7649 0.052 Uiso 1 1 calc R
C11 C 0.1299(5) 0.6566(3) 0.9324(3) 0.0643(8) Uani 1 1 d .
H11A H 0.1377 0.5895 0.9736 0.096 Uiso 1 1 calc R
H11B H 0.0230 0.7041 0.9461 0.096 Uiso 1 1 calc R
H11C H 0.2554 0.7184 0.9588 0.096 Uiso 1 1 calc R
C10' C 0.2145(3) 0.37368(19) 0.77269(19) 0.0368(5) Uani 1 1 d .
H10C H 0.0713 0.3393 0.7538 0.044 Uiso 1 1 calc R
H10D H 0.2651 0.3258 0.7107 0.044 Uiso 1 1 calc R
C11' C 0.3146(6) 0.3454(3) 0.8795(2) 0.0725(10) Uani 1 1 d .
H11D H 0.4571 0.3771 0.8982 0.109 Uiso 1 1 calc R
H11E H 0.2902 0.2504 0.8697 0.109 Uiso 1 1 calc R
H11F H 0.2626 0.3900 0.9412 0.109 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
C9 N2 C10 123.82(16)
C9 N2 C10' 117.75(17)
C10 N2 C10' 118.29(17)
C9 O2 C4 115.39(14)
C3 O4 C7 112.83(12)
O1 C1 C2 110.00(14)
O1 C1 C8 108.84(14)
C2 C1 C8 109.43(14)
F2 C2 F1 104.34(13)
F2 C2 C1 111.21(14)
F1 C2 C1 108.16(13)
F2 C2 C3 111.02(13)
F1 C2 C3 105.72(13)
C1 C2 C3 115.58(14)
O4 C3 N1 105.79(13)
O4 C3 C2 104.33(13)
N1 C3 C2 111.11(14)
O4 C3 C4 110.30(13)
N1 C3 C4 108.27(14)
C2 C3 C4 116.50(14)
O2 C4 C5 109.09(14)
O2 C4 C3 111.01(13)
C5 C4 C3 113.38(14)
C5' C5 C6 110.11(15)
C5' C5 C5" 107.78(15)
C6 C5 C5" 110.82(15)
C5' C5 C4 109.80(15)
C6 C5 C4 109.24(14)
C5" C5 C4 109.07(15)
C5 C6 C7 112.51(14)
O4 C7 C8 108.64(13)
O4 C7 C6 112.32(13)
C8 C7 C6 112.96(15)
O5 C8 C1 109.27(14)
O5 C8 C7 109.64(14)
C1 C8 C7 110.69(14)
O3 C9 N2 125.66(18)
O3 C9 O2 122.17(17)
N2 C9 O2 112.17(16)
N2 C10 C11 113.23(19)
C11' C10' N2 114.36(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C2 1.362(2)
F2 C2 1.3569(19)
N2 C9 1.321(3)
N2 C10 1.449(3)
N2 C10' 1.458(2)
O5 C8 1.403(2)
O1 C1 1.401(2)
N1 C3 1.425(2)
O2 C9 1.358(2)
O2 C4 1.430(2)
O3 C9 1.209(2)
O4 C3 1.409(2)
O4 C7 1.433(2)
C1 C2 1.503(2)
C1 C8 1.509(2)
C2 C3 1.542(2)
C3 C4 1.548(2)
C4 C5 1.526(2)
C5 C5' 1.510(3)
C5 C6 1.514(2)
C5 C5" 1.523(3)
C6 C7 1.525(2)
C7 C8 1.511(2)
C10 C11 1.492(4)
C10' C11' 1.456(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11382587
