#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:34:55 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257127 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038750.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_4038750
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         'C4 H8 F2 N, Cl'
_chemical_formula_sum            'C4 H8 Cl F2 N'
_chemical_formula_weight         143.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                106.605(4)
_cell_angle_beta                 105.053(4)
_cell_angle_gamma                91.961(4)
_cell_formula_units_Z            2
_cell_length_a                   6.0157(4)
_cell_length_b                   7.4732(4)
_cell_length_c                   7.6279(4)
_cell_measurement_reflns_used    1743
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      3.53
_cell_volume                     315.16(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      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4817
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.531
_diffrn_reflns_theta_min         2.864
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.540
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       block
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0873P)²+0.4409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1145
_reflns_number_total             1312
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01848_si_005.cif
_cod_data_source_block           xr170
_cod_depositor_comments
'Adding full bibliography for 4038748--4038751.cif.'
_cod_database_code               4038750
_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   0.872
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_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_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 0.2884(5) 0.7029(4) 0.1976(4) 0.0206(6) Uani 1 1 d . . . . .
H1 H 0.366368 0.586904 0.198104 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0324(5) 0.6884(5) 0.1888(4) 0.0256(7) Uani 1 1 d . . . . .
H2A H -0.068229 0.761635 0.117995 0.031 Uiso 1 1 calc R U . . .
H2B H -0.043040 0.565654 0.181630 0.031 Uiso 1 1 calc R U . . .
C3 C 0.2100(5) 0.7944(4) 0.3698(4) 0.0195(6) Uani 1 1 d . . . . .
H3 H 0.217647 0.934627 0.409920 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3691(5) 0.8249(4) 0.0976(4) 0.0238(6) Uani 1 1 d . . . . .
H4 H 0.256993 0.917233 0.075154 0.029 Uiso 1 1 calc R U . . .
CL1 Cl 0.18426(12) 0.26242(9) 0.32698(10) 0.0244(3) Uani 1 1 d . . . . .
F1 F 0.5879(3) 0.9166(3) 0.1994(3) 0.0328(5) Uani 1 1 d . . . . .
F2 F 0.3958(3) 0.7140(3) -0.0720(2) 0.0328(5) Uani 1 1 d . . . . .
N1 N 0.2623(4) 0.7049(3) 0.5225(3) 0.0189(5) Uani 1 1 d . . . . .
H1N H 0.412(6) 0.744(5) 0.600(5) 0.022(8) Uiso 1 1 d . . . . .
H3N H 0.233(6) 0.570(5) 0.465(5) 0.027(9) Uiso 1 1 d . . . . .
H2N H 0.162(6) 0.724(5) 0.586(5) 0.027(9) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 118.3(2) . . ?
C4 C1 C2 117.6(3) . . ?
C3 C1 C2 59.18(18) . . ?
C3 C2 C1 59.62(18) . . ?
N1 C3 C2 116.9(2) . . ?
N1 C3 C1 115.9(2) . . ?
C2 C3 C1 61.19(19) . . ?
F2 C4 F1 104.6(2) . . ?
F2 C4 C1 109.1(2) . . ?
F1 C4 C1 110.8(2) . . ?
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 1.486(4) . ?
C1 C3 1.499(4) . ?
C1 C2 1.522(4) . ?
C2 C3 1.492(4) . ?
C3 N1 1.474(4) . ?
C4 F2 1.375(3) . ?
C4 F1 1.382(3) . ?
