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#$Date: 2020-10-04 06:34:55 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257127 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038751.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_4038751
loop_
_publ_author_name
'Chernykh, Anton V.'
'Olifir, Oleksandr S.'
'Kuchkovska, Yuliya O.'
'Volochnyuk, Dmitriy M.'
'Yarmolchuk, Vladimir S.'
'Grygorenko, Oleksandr O.'
_publ_section_title
;
 Fluoroalkyl-Substituted Cyclopropane Derivatives: Synthesis and
 Physicochemical Properties.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12692
_journal_page_last               12702
_journal_paper_doi               10.1021/acs.joc.0c01848
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C11 H10 F3 N O'
_chemical_formula_sum            'C11 H10 F3 N O'
_chemical_formula_weight         229.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6036(13)
_cell_length_b                   11.7912(19)
_cell_length_c                   21.270(3)
_cell_measurement_reflns_used    958
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      20.88
_cell_measurement_theta_min      3.05
_cell_volume                     2157.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7596
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.013
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_min         3.045
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0632P)²+0.7244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1640
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1081
_reflns_number_total             1898
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01848_si_003.cif
_cod_data_source_block           xr265
_cod_depositor_comments
'Adding full bibliography for 4038748--4038751.cif.'
_cod_database_code               4038751
_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   0.942
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_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'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4251(4) 0.7111(3) 0.40085(16) 0.0508(10) Uani 1 1 d . . . . .
H1 H 0.528425 0.706034 0.420057 0.061 Uiso 1 1 calc R U . . .
C2 C 0.4274(4) 0.7022(3) 0.33005(16) 0.0497(10) Uani 1 1 d . . . . .
H2 H 0.530712 0.693817 0.311174 0.060 Uiso 1 1 calc R U . . .
C3 C 0.3752(5) 0.6053(3) 0.36964(17) 0.0589(10) Uani 1 1 d . . . . .
H3A H 0.265181 0.587509 0.369905 0.071 Uiso 1 1 calc R U . . .
H3B H 0.443485 0.540071 0.372692 0.071 Uiso 1 1 calc R U . . .
C4 C 0.3151(5) 0.7808(4) 0.43703(17) 0.0587(11) Uani 1 1 d . . . . .
C5 C 0.3112(4) 0.7633(3) 0.29077(15) 0.0410(9) Uani 1 1 d . . . . .
C6 C 0.2909(4) 0.8844(3) 0.19676(15) 0.0386(8) Uani 1 1 d . . . . .
C7 C 0.1840(4) 0.9646(3) 0.21699(17) 0.0480(9) Uani 1 1 d . . . . .
H7 H 0.163462 0.973378 0.259638 0.058 Uiso 1 1 calc R U . . .
C8 C 0.1082(4) 1.0316(3) 0.1731(2) 0.0616(11) Uani 1 1 d . . . . .
H8 H 0.035073 1.084447 0.186517 0.074 Uiso 1 1 calc R U . . .
C9 C 0.1394(5) 1.0209(3) 0.1107(2) 0.0679(12) Uani 1 1 d . . . . .
H9 H 0.088139 1.066306 0.081631 0.081 Uiso 1 1 calc R U . . .
C10 C 0.2484(5) 0.9418(4) 0.0907(2) 0.0683(12) Uani 1 1 d . . . . .
H10 H 0.271030 0.935005 0.048136 0.082 Uiso 1 1 calc R U . . .
C11 C 0.3230(4) 0.8732(3) 0.13364(16) 0.0501(9) Uani 1 1 d . . . . .
H11 H 0.394867 0.819659 0.120026 0.060 Uiso 1 1 calc R U . . .
F1 F 0.3556(3) 0.7828(2) 0.49772(10) 0.0934(9) Uani 1 1 d . . . . .
F2 F 0.1683(3) 0.7443(2) 0.43731(10) 0.0734(8) Uani 1 1 d . . . . .
F3 F 0.3080(3) 0.8884(2) 0.41752(13) 0.0918(9) Uani 1 1 d . . . . .
N1 N 0.3727(4) 0.8163(3) 0.24086(13) 0.0421(8) Uani 1 1 d . . . . .
O1 O 0.1723(3) 0.7630(2) 0.30338(10) 0.0538(7) Uani 1 1 d . . . . .
H1N H 0.461(4) 0.804(3) 0.2336(13) 0.030(10) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C1 C3 121.3(4) . . ?
C4 C1 C2 124.7(3) . . ?
C3 C1 C2 59.8(2) . . ?
C3 C2 C5 119.1(3) . . ?
C3 C2 C1 59.0(2) . . ?
C5 C2 C1 121.1(3) . . ?
C1 C3 C2 61.2(2) . . ?
F2 C4 F1 104.4(3) . . ?
F2 C4 F3 105.3(3) . . ?
F1 C4 F3 107.1(3) . . ?
F2 C4 C1 115.6(3) . . ?
F1 C4 C1 110.3(3) . . ?
F3 C4 C1 113.4(3) . . ?
O1 C5 N1 124.0(3) . . ?
O1 C5 C2 122.1(3) . . ?
N1 C5 C2 113.9(3) . . ?
C11 C6 C7 120.0(3) . . ?
C11 C6 N1 119.3(3) . . ?
C7 C6 N1 120.6(3) . . ?
C8 C7 C6 119.5(3) . . ?
C9 C8 C7 120.7(4) . . ?
C8 C9 C10 119.7(4) . . ?
C11 C10 C9 120.3(4) . . ?
C10 C11 C6 119.7(4) . . ?
C5 N1 C6 126.2(3) . . ?
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
C1 C4 1.471(5) . ?
C1 C3 1.477(5) . ?
C1 C2 1.510(5) . ?
C2 C3 1.489(5) . ?
C2 C5 1.489(5) . ?
C4 F2 1.334(4) . ?
C4 F1 1.337(4) . ?
C4 F3 1.337(4) . ?
C5 O1 1.225(4) . ?
C5 N1 1.340(4) . ?
C6 C11 1.377(4) . ?
C6 C7 1.388(4) . ?
C6 N1 1.422(4) . ?
C7 C8 1.385(5) . ?
C8 C9 1.360(5) . ?
C9 C10 1.390(6) . ?
C10 C11 1.378(5) . ?
