#------------------------------------------------------------------------------
#$Date: 2020-01-28 02:15:35 +0200 (Tue, 28 Jan 2020) $
#$Revision: 247269 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/78/4037862.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_4037862
loop_
_publ_author_name
'Trofymchuk, Serhii'
'Bugera, Maksym'
'Klipkov, Anton A.'
'Razhyk, Bohdan'
'Semenov, Sergey'
'Tarasenko, Karen'
'Starova, Viktoriia S.'
'Zaporozhets, Olga A.'
'Tananaiko, Oksana Y.'
'Alekseenko, Anatoliy N.'
'Pustovit, Yurii'
'Kiriakov, Oleksandr'
'Gerus, Igor I.'
'Tolmachev, Andrei A.'
'Mykhailiuk, Pavel K.'
_publ_section_title
;
 Deoxofluorination of (Hetero)aromatic Acids.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03011
_journal_year                    2020
_chemical_formula_sum            'C6 H11 Cl F3 N O2'
_chemical_formula_weight         221.61
_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   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 99.556(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5754(18)
_cell_length_b                   7.6962(9)
_cell_length_c                   10.3772(15)
_cell_measurement_reflns_used    1982
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.0027
_cell_measurement_theta_min      3.1089
_cell_volume                     990.4(2)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9132
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.115
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.138
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0840
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1538P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2240
_refine_ls_wR_factor_ref         0.2528
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1686
_reflns_number_total             2785
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03011_si_001.cif
_cod_data_source_block           t123
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037862
_shelx_shelxl_version_number     2016/6
_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   0.924
_shelx_estimated_absorpt_t_max   0.980
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
Cl1 Cl -0.00864(7) 0.73159(11) 0.41020(8) 0.0546(3) Uani 1 1 d . .
F1 F 0.4691(3) 0.2513(5) 0.7586(5) 0.1256(15) Uani 1 1 d . .
F2 F 0.4736(2) 0.3128(5) 0.9561(4) 0.1084(11) Uani 1 1 d . .
F3 F 0.4039(2) 0.0781(3) 0.8852(4) 0.1091(12) Uani 1 1 d . .
O1 O 0.2484(2) 0.4001(4) 1.0228(3) 0.0722(8) Uani 1 1 d . .
O2 O 0.1716(2) 0.1760(3) 0.9074(3) 0.0607(7) Uani 1 1 d . .
H2O H 0.134307 0.173510 0.965196 0.091 Uiso 1 1 calc R U
N1 N 0.1146(2) 0.8836(4) 0.6795(3) 0.0532(7) Uani 1 1 d . .
H1NC H 0.082280 0.834536 0.605650 0.080 Uiso 1 1 calc R U
H1NB H 0.124256 0.996327 0.666064 0.080 Uiso 1 1 calc R U
H1NA H 0.073602 0.870528 0.740999 0.080 Uiso 1 1 calc R U
C1 C 0.2389(3) 0.3060(4) 0.9278(3) 0.0475(7) Uani 1 1 d . .
C2 C 0.3041(2) 0.3296(4) 0.8192(3) 0.0478(7) Uani 1 1 d . .
H2 H 0.265881 0.271725 0.740906 0.057 Uiso 1 1 calc R U
C3 C 0.3167(3) 0.5213(4) 0.7870(4) 0.0536(8) Uani 1 1 d . .
H3B H 0.351381 0.581540 0.864841 0.064 Uiso 1 1 calc R U
H3A H 0.362985 0.531481 0.721352 0.064 Uiso 1 1 calc R U
C4 C 0.2094(3) 0.6076(4) 0.7369(4) 0.0525(8) Uani 1 1 d . .
H4B H 0.179183 0.558002 0.652876 0.063 Uiso 1 1 calc R U
H4A H 0.159768 0.584221 0.797058 0.063 Uiso 1 1 calc R U
C5 C 0.2205(3) 0.7996(5) 0.7225(4) 0.0626(10) Uani 1 1 d . .
H5B H 0.253746 0.848772 0.805584 0.075 Uiso 1 1 calc R U
H5A H 0.267355 0.823261 0.659186 0.075 Uiso 1 1 calc R U
C6 C 0.4131(3) 0.2457(5) 0.8552(5) 0.0682(11) Uani 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'
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
O1 C1 O2 124.3(3)
O1 C1 C2 122.8(3)
O2 C1 C2 112.9(3)
C6 C2 C1 110.4(3)
C6 C2 C3 110.2(3)
C1 C2 C3 111.6(3)
C4 C3 C2 112.3(3)
C5 C4 C3 112.0(3)
N1 C5 C4 111.6(3)
F2 C6 F1 106.6(4)
F2 C6 F3 105.0(4)
F1 C6 F3 106.7(3)
F2 C6 C2 114.7(3)
F1 C6 C2 112.1(4)
F3 C6 C2 111.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C6 1.317(6)
F2 C6 1.295(5)
F3 C6 1.336(5)
O1 C1 1.213(4)
O2 C1 1.305(4)
N1 C5 1.481(5)
C1 C2 1.510(4)
C2 C6 1.506(5)
C2 C3 1.527(4)
C3 C4 1.516(5)
C4 C5 1.494(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1NA Cl1 0.89 2.32 3.186(3) 165.0 4_576
N1 H1NC Cl1 0.89 2.30 3.185(3) 174.8 .
O2 H2O Cl1 0.82 2.25 3.041(3) 163.3 2_546
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
O1 C1 C2 C6 83.0(4)
O2 C1 C2 C6 -97.7(3)
O1 C1 C2 C3 -40.0(5)
O2 C1 C2 C3 139.4(3)
C6 C2 C3 C4 174.2(3)
C1 C2 C3 C4 -62.7(4)
C2 C3 C4 C5 172.4(3)
C3 C4 C5 N1 -177.3(3)
C1 C2 C6 F2 -63.4(5)
C3 C2 C6 F2 60.4(5)
C1 C2 C6 F1 174.9(3)
C3 C2 C6 F1 -61.4(4)
C1 C2 C6 F3 55.5(4)
C3 C2 C6 F3 179.3(4)
