#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:34:55 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257127 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038749.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_4038749
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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 93.058(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1598(9)
_cell_length_b                   11.2723(17)
_cell_length_c                   17.688(3)
_cell_measurement_reflns_used    880
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      2.31
_cell_volume                     1027.3(3)
_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      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0621
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6646
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.045
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_min         2.143
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       needl
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0608P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1176
_reflns_number_total             1812
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01848_si_004.cif
_cod_data_source_block           xr270
_cod_depositor_comments
'Adding full bibliography for 4038748--4038751.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038749
_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   0.925
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9155(3) 0.51218(14) 0.60791(8) 0.0446(5) Uani 1 1 d . . . . .
F2 F 1.1000(4) 0.43522(15) 0.70710(9) 0.0549(6) Uani 1 1 d . . . . .
F3 F 0.6862(4) 0.43945(16) 0.69382(9) 0.0562(6) Uani 1 1 d . . . . .
N1 N 0.9721(5) 0.52897(19) 0.85142(12) 0.0274(6) Uani 1 1 d . . . . .
O1 O 0.5460(4) 0.50557(16) 0.86856(10) 0.0323(5) Uani 1 1 d . . . . .
C1 C 0.8966(5) 0.6203(2) 0.71992(13) 0.0272(7) Uani 1 1 d . . . . .
H1 H 0.775520 0.678863 0.694412 0.033 Uiso 1 1 calc R U . . .
C2 C 1.1383(6) 0.6732(3) 0.75664(14) 0.0351(7) Uani 1 1 d . . . . .
H2A H 1.299226 0.625339 0.757138 0.042 Uiso 1 1 calc R U . . .
H2B H 1.164407 0.759755 0.751237 0.042 Uiso 1 1 calc R U . . .
C3 C 0.9268(5) 0.6325(2) 0.80516(14) 0.0290(7) Uani 1 1 d . . . . .
H3 H 0.821801 0.696691 0.827768 0.035 Uiso 1 1 calc R U . . .
C4 C 0.9007(6) 0.5032(2) 0.68339(14) 0.0314(7) Uani 1 1 d . . . . .
C5 C 0.7730(5) 0.4726(2) 0.88094(13) 0.0250(6) Uani 1 1 d . . . . .
C6 C 0.8380(5) 0.3679(2) 0.93057(13) 0.0265(7) Uani 1 1 d . . . . .
C7 C 1.0484(5) 0.2945(2) 0.91889(14) 0.0324(7) Uani 1 1 d . . . . .
H7 H 1.162247 0.312220 0.879951 0.039 Uiso 1 1 calc R U . . .
C8 C 1.0922(6) 0.1948(2) 0.96438(16) 0.0384(8) Uani 1 1 d . . . . .
H8 H 1.233466 0.143485 0.955641 0.046 Uiso 1 1 calc R U . . .
C9 C 0.9307(6) 0.1707(3) 1.02206(15) 0.0372(8) Uani 1 1 d . . . . .
H9 H 0.961404 0.103010 1.053297 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7256(6) 0.2444(2) 1.03431(14) 0.0342(7) Uani 1 1 d . . . . .
H10 H 0.616768 0.228330 1.074738 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6762(5) 0.3414(2) 0.98856(14) 0.0314(7) Uani 1 1 d . . . . .
H11 H 0.530653 0.390526 0.996675 0.038 Uiso 1 1 calc R U . . .
H1N H 1.138(5) 0.509(2) 0.8662(13) 0.026(7) 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
C5 N1 C3 120.2(2) . . ?
C4 C1 C2 121.1(2) . . ?
C4 C1 C3 121.1(2) . . ?
C2 C1 C3 59.54(17) . . ?
C3 C2 C1 60.72(17) . . ?
N1 C3 C2 118.3(2) . . ?
N1 C3 C1 119.9(2) . . ?
C2 C3 C1 59.74(17) . . ?
F2 C4 F3 106.1(2) . . ?
F2 C4 F1 105.8(2) . . ?
F3 C4 F1 105.6(2) . . ?
F2 C4 C1 114.0(2) . . ?
F3 C4 C1 112.9(2) . . ?
F1 C4 C1 111.8(2) . . ?
O1 C5 N1 121.9(2) . . ?
O1 C5 C6 121.4(2) . . ?
N1 C5 C6 116.8(2) . . ?
C7 C6 C11 119.2(3) . . ?
C7 C6 C5 122.3(2) . . ?
C11 C6 C5 118.5(2) . . ?
C6 C7 C8 119.9(3) . . ?
C9 C8 C7 120.1(3) . . ?
C10 C9 C8 119.9(3) . . ?
C9 C10 C11 120.6(3) . . ?
C10 C11 C6 120.3(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
F1 C4 1.345(3) . ?
F2 C4 1.332(3) . ?
F3 C4 1.341(3) . ?
N1 C5 1.337(3) . ?
N1 C3 1.437(3) . ?
O1 C5 1.237(3) . ?
C1 C4 1.471(4) . ?
C1 C2 1.499(4) . ?
C1 C3 1.514(3) . ?
C2 C3 1.496(4) . ?
C5 C6 1.499(4) . ?
C6 C7 1.389(4) . ?
C6 C11 1.389(4) . ?
C7 C8 1.393(4) . ?
C8 C9 1.378(4) . ?
C9 C10 1.372(4) . ?
C10 C11 1.376(4) . ?
