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#$Date: 2019-11-09 02:19:25 +0200 (Sat, 09 Nov 2019) $
#$Revision: 225399 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/47/4034708.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_4034708
loop_
_publ_author_name
'Chalyk, Bohdan A.'
'Khutorianskyi, Andrii'
'Lysenko, Andrii'
'Fil, Yulia'
'Kuchkovska, Yuliya O.'
'Gavrilenko, Konstantin S.'
'Bakanovych, Iulia'
'Moroz, Yurii S.'
'Gorlova, Alina O.'
'Grygorenko, Oleksandr O.'
_publ_section_title
;
 Regioselective Synthesis of Functionalized 3- or 5-Fluoroalkyl Isoxazoles
 and Pyrazoles from Fluoroalkyl Ynones and Binucleophiles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02258
_journal_year                    2019
_chemical_formula_moiety         'C6 H8 F2 N2 O'
_chemical_formula_sum            'C6 H8 F2 N2 O'
_chemical_formula_weight         162.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 105.295(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.914(4)
_cell_length_b                   10.509(5)
_cell_length_c                   9.039(5)
_cell_measurement_reflns_used    697
_cell_measurement_temperature    138(2)
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.67
_cell_volume                     725.1(6)
_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-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      138(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6625
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.454
_diffrn_reflns_theta_min         2.668
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0475
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+0.4833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.000
_reflns_number_gt                998
_reflns_number_total             1488
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02258_si_002.cif
_cod_data_source_block           xr25
_cod_original_cell_volume        725.1(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034708
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.935
_shelx_estimated_absorpt_t_max   0.989
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 0.6194(3) 0.2998(2) 0.4906(2) 0.0860(7) Uani 1 1 d . .
F2 F 0.6946(3) 0.47847(19) 0.60293(19) 0.0790(6) Uani 1 1 d . .
O1 O 0.9516(3) 0.65933(18) 0.0262(2) 0.0498(5) Uani 1 1 d . .
N1 N 0.8918(3) 0.4426(2) 0.1950(2) 0.0430(5) Uani 1 1 d . .
N2 N 0.8870(3) 0.37176(18) 0.3175(2) 0.0422(5) Uani 1 1 d . .
C1 C 0.7871(3) 0.4373(2) 0.3851(2) 0.0392(6) Uani 1 1 d . .
C2 C 0.7297(3) 0.5505(2) 0.3076(3) 0.0416(6) Uani 1 1 d . .
H2 H 0.657006 0.613745 0.334206 0.050 Uiso 1 1 calc R U
C3 C 0.8001(3) 0.5509(2) 0.1857(3) 0.0390(6) Uani 1 1 d . .
C4 C 0.7509(4) 0.3850(3) 0.5259(3) 0.0512(7) Uani 1 1 d . .
H4 H 0.858841 0.344722 0.592451 0.061 Uiso 1 1 calc R U
C5 C 0.7851(3) 0.6424(2) 0.0556(3) 0.0449(6) Uani 1 1 d . .
H5 H 0.743160 0.726270 0.084273 0.054 Uiso 1 1 calc R U
C6 C 0.6601(4) 0.5959(3) -0.0876(3) 0.0584(8) Uani 1 1 d . .
H6A H 0.655499 0.656776 -0.170640 0.088 Uiso 1 1 calc R U
H6B H 0.543208 0.587285 -0.070778 0.088 Uiso 1 1 calc R U
H6C H 0.699171 0.512949 -0.115551 0.088 Uiso 1 1 calc R U
H1N H 0.956(3) 0.416(2) 0.136(3) 0.042(7) Uiso 1 1 d . .
H1O H 1.004(5) 0.713(4) 0.074(5) 0.104(16) Uiso 1 1 d . .
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
C3 N1 N2 112.9(2)
C1 N2 N1 104.1(2)
N2 C1 C2 111.7(2)
N2 C1 C4 118.7(2)
C2 C1 C4 129.5(2)
C3 C2 C1 105.1(2)
N1 C3 C2 106.1(2)
N1 C3 C5 121.5(2)
C2 C3 C5 132.3(2)
F2 C4 F1 105.5(2)
F2 C4 C1 109.8(2)
F1 C4 C1 110.8(2)
O1 C5 C6 108.4(2)
O1 C5 C3 109.9(2)
C6 C5 C3 111.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C4 1.346(3)
F2 C4 1.346(3)
O1 C5 1.423(3)
N1 C3 1.341(3)
N1 N2 1.344(3)
N2 C1 1.314(3)
C1 C2 1.395(3)
C1 C4 1.483(3)
C2 C3 1.359(3)
C3 C5 1.499(3)
C5 C6 1.489(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
C3 N1 N2 C1 0.9(3)
N1 N2 C1 C2 -0.8(3)
N1 N2 C1 C4 179.1(2)
N2 C1 C2 C3 0.3(3)
C4 C1 C2 C3 -179.5(3)
N2 N1 C3 C2 -0.8(3)
N2 N1 C3 C5 -178.6(2)
C1 C2 C3 N1 0.3(3)
C1 C2 C3 C5 177.8(3)
N2 C1 C4 F2 161.4(2)
C2 C1 C4 F2 -18.8(4)
N2 C1 C4 F1 -82.4(3)
C2 C1 C4 F1 97.4(3)
N1 C3 C5 O1 -44.4(3)
C2 C3 C5 O1 138.4(3)
N1 C3 C5 C6 75.9(3)
C2 C3 C5 C6 -101.3(3)
