data_ID184

_publ_section_acknowledgements
;
Crystal structure determination was performed in the Department of Structural
Studies of Zelinsky Institute of Organic Chemistry, Moscow.
;

_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H15 F4 N O2'
_chemical_formula_sum             'C14 H15 F4 N O2'  
_chemical_formula_weight          305.27

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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.
;
 
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'
 
_cell_length_a                    13.4130(3)
_cell_length_b                    7.3746(2)
_cell_length_c                    13.8840(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90.2570(10)
_cell_angle_gamma                 90
_cell_volume                      1373.33(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used      9235
_cell_measurement_theta_min        2.93
_cell_measurement_theta_max       36.75

_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.476
_exptl_crystal_F_000              632
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.59
_exptl_crystal_size_mid           0.56
_exptl_crystal_size_min           0.15
_exptl_absorpt_coefficient_mu     0.134
_shelx_estimated_absorpt_T_min    0.925
_shelx_estimated_absorpt_T_max    0.980
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6996
_exptl_absorpt_correction_T_max   0.7473
_exptl_absorpt_process_details
;
 SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10).
;
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method        'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean  7.31
_diffrn_reflns_number             52704
_diffrn_reflns_av_unetI/netI      0.0237
_diffrn_reflns_av_R_equivalents   0.0350
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          2.934
_diffrn_reflns_theta_max          37.060
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              7002
_reflns_number_gt                 5318
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'APEX3 (Bruker, 2019)'
_computing_cell_refinement        'SAINT (Bruker, 2019)'
_computing_data_reduction         'SAINT (Bruker, 2019)'
_computing_structure_solution
;
SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0576P)²+0.2896P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          7002
_refine_ls_number_parameters      192
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0606
_refine_ls_R_factor_gt            0.0406
_refine_ls_wR_factor_ref          0.1205
_refine_ls_wR_factor_gt           0.1097
_refine_ls_goodness_of_fit_ref    1.046
_refine_ls_restrained_S_all       1.046
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
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 0.71517(4) 0.29588(8) 0.41169(4) 0.02642(12) Uani 1 1 d . . . . .
F2 F 0.85084(4) 0.29908(7) 0.49906(4) 0.02230(10) Uani 1 1 d . . . . .
F3 F 0.80913(4) 0.44555(10) 0.26332(4) 0.03303(14) Uani 1 1 d . . . . .
F4 F 0.89163(4) 0.21219(8) 0.31862(5) 0.03264(14) Uani 1 1 d . . . . .
O1 O 0.58088(5) 0.56919(10) 0.89007(4) 0.02662(14) Uani 1 1 d . . . . .
O2 O 0.44306(4) 0.59289(9) 0.79854(4) 0.02088(11) Uani 1 1 d . . . . .
N1 N 0.86875(5) 0.68457(9) 0.47461(5) 0.01760(12) Uani 1 1 d . . . . .
C1 C 0.77483(5) 0.58336(10) 0.46149(5) 0.01567(12) Uani 1 1 d . . . . .
H1 H 0.734802 0.643719 0.409698 0.019 Uiso 1 1 calc R U . . .
C2 C 0.80027(5) 0.39063(10) 0.42872(5) 0.01768(13) Uani 1 1 d . . . . .
C3 C 0.86602(6) 0.38712(12) 0.33899(6) 0.02183(15) Uani 1 1 d . . . . .
C4 C 0.95631(6) 0.50439(12) 0.35150(6) 0.02165(14) Uani 1 1 d . . . . .
H4A H 0.992765 0.512748 0.289820 0.026 Uiso 1 1 calc R U . . .
H4B H 1.001477 0.450140 0.400179 0.026 Uiso 1 1 calc R U . . .
C5 C 0.92468(6) 0.69322(12) 0.38393(6) 0.02187(15) Uani 1 1 d . . . . .
H5A H 0.984556 0.769970 0.392976 0.026 Uiso 1 1 calc R U . . .
H5B H 0.882566 0.749590 0.333426 0.026 Uiso 1 1 calc R U . . .
C6 C 0.84839(7) 0.86958(11) 0.50840(7) 0.02622(17) Uani 1 1 d . . . . .
H6A H 0.911066 0.937439 0.512740 0.039 Uiso 1 1 calc R U . . .
H6B H 0.817213 0.864517 0.572041 0.039 Uiso 1 1 calc R U . . .
H6C H 0.803301 0.930217 0.462950 0.039 Uiso 1 1 calc R U . . .
C7 C 0.71311(5) 0.57761(10) 0.55262(5) 0.01502(12) Uani 1 1 d . . . . .
C8 C 0.75654(5) 0.53507(11) 0.64150(5) 0.01871(13) Uani 1 1 d . . . . .
H8 H 0.825607 0.507185 0.645115 0.022 Uiso 1 1 calc R U . . .
C9 C 0.69933(6) 0.53337(11) 0.72438(5) 0.01870(13) Uani 1 1 d . . . . .
H9 H 0.729381 0.505190 0.784631 0.022 Uiso 1 1 calc R U . . .
C10 C 0.59760(5) 0.57298(10) 0.71952(5) 0.01554(12) Uani 1 1 d . . . . .
C11 C 0.55333(5) 0.61277(10) 0.63119(5) 0.01672(12) Uani 1 1 d . . . . .
H11 H 0.483995 0.638294 0.627512 0.020 Uiso 1 1 calc R U . . .
C12 C 0.61137(5) 0.61496(10) 0.54808(5) 0.01649(12) Uani 1 1 d . . . . .
H12 H 0.581208 0.642205 0.487754 0.020 Uiso 1 1 calc R U . . .
C13 C 0.54130(6) 0.57696(10) 0.81172(5) 0.01702(12) Uani 1 1 d . . . . .
C14 C 0.38539(6) 0.60717(12) 0.88622(6) 0.02205(15) Uani 1 1 d . . . . .
H14A H 0.314244 0.612095 0.870059 0.033 Uiso 1 1 calc R U . . .
H14B H 0.404473 0.717734 0.920843 0.033 Uiso 1 1 calc R U . . .
H14C H 0.398453 0.501322 0.927044 0.033 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 C2 1.3581(9) . ?
F2 C2 1.3653(9) . ?
F3 C3 1.3655(10) . ?
F4 C3 1.3650(10) . ?
O1 C13 1.2097(9) . ?
O2 C13 1.3347(9) . ?
O2 C14 1.4491(9) . ?
N1 C6 1.4688(11) . ?
N1 C5 1.4698(10) . ?
N1 C1 1.4748(9) . ?
C1 C7 1.5158(10) . ?
C1 C2 1.5313(11) . ?
C1 H1 1.0000 . ?
C2 C3 1.5297(11) . ?
C3 C4 1.4977(11) . ?
C4 C5 1.5243(12) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C12 1.3934(10) . ?
C7 C8 1.3979(10) . ?
C8 C9 1.3860(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.3968(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.3915(10) . ?
C10 C13 1.4894(10) . ?
C11 C12 1.3950(10) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
 
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
C13 O2 C14 114.94(6) . . ?
C6 N1 C5 109.24(6) . . ?
C6 N1 C1 110.46(6) . . ?
C5 N1 C1 110.80(6) . . ?
N1 C1 C7 112.36(6) . . ?
N1 C1 C2 108.37(6) . . ?
C7 C1 C2 110.20(6) . . ?
N1 C1 H1 108.6 . . ?
C7 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
F1 C2 F2 106.53(6) . . ?
F1 C2 C3 109.68(6) . . ?
F2 C2 C3 106.73(6) . . ?
F1 C2 C1 109.94(6) . . ?
F2 C2 C1 110.92(6) . . ?
C3 C2 C1 112.81(6) . . ?
F4 C3 F3 106.21(7) . . ?
F4 C3 C4 111.45(7) . . ?
F3 C3 C4 110.85(7) . . ?
F4 C3 C2 109.35(7) . . ?
F3 C3 C2 107.40(6) . . ?
C4 C3 C2 111.38(6) . . ?
C3 C4 C5 109.62(7) . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C4 110.92(6) . . ?
N1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 119.24(6) . . ?
C12 C7 C1 119.68(6) . . ?
C8 C7 C1 121.08(6) . . ?
C9 C8 C7 120.32(7) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.17(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.97(7) . . ?
C11 C10 C13 122.50(6) . . ?
C9 C10 C13 117.49(6) . . ?
C10 C11 C12 119.60(7) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 120.69(7) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 O2 123.82(7) . . ?
O1 C13 C10 123.35(7) . . ?
O2 C13 C10 112.83(6) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
 
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
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C6 N1 C1 C7 -56.62(8) . . . . ?
C5 N1 C1 C7 -177.83(6) . . . . ?
C6 N1 C1 C2 -178.63(6) . . . . ?
C5 N1 C1 C2 60.17(8) . . . . ?
N1 C1 C2 F1 -177.25(6) . . . . ?
C7 C1 C2 F1 59.43(8) . . . . ?
N1 C1 C2 F2 65.19(7) . . . . ?
C7 C1 C2 F2 -58.13(8) . . . . ?
N1 C1 C2 C3 -54.48(8) . . . . ?
C7 C1 C2 C3 -177.80(6) . . . . ?
F1 C2 C3 F4 -61.66(8) . . . . ?
F2 C2 C3 F4 53.37(8) . . . . ?
C1 C2 C3 F4 175.43(6) . . . . ?
F1 C2 C3 F3 53.18(9) . . . . ?
F2 C2 C3 F3 168.20(6) . . . . ?
C1 C2 C3 F3 -69.73(8) . . . . ?
F1 C2 C3 C4 174.72(7) . . . . ?
F2 C2 C3 C4 -70.25(8) . . . . ?
C1 C2 C3 C4 51.81(9) . . . . ?
F4 C3 C4 C5 -174.36(7) . . . . ?
F3 C3 C4 C5 67.57(8) . . . . ?
C2 C3 C4 C5 -51.95(9) . . . . ?
C6 N1 C5 C4 174.38(7) . . . . ?
C1 N1 C5 C4 -63.69(8) . . . . ?
C3 C4 C5 N1 58.38(9) . . . . ?
N1 C1 C7 C12 133.49(7) . . . . ?
C2 C1 C7 C12 -105.55(8) . . . . ?
N1 C1 C7 C8 -46.61(9) . . . . ?
C2 C1 C7 C8 74.35(9) . . . . ?
C12 C7 C8 C9 -1.18(11) . . . . ?
C1 C7 C8 C9 178.92(7) . . . . ?
C7 C8 C9 C10 0.45(12) . . . . ?
C8 C9 C10 C11 0.54(12) . . . . ?
C8 C9 C10 C13 -177.32(7) . . . . ?
C9 C10 C11 C12 -0.78(11) . . . . ?
C13 C10 C11 C12 176.97(7) . . . . ?
C8 C7 C12 C11 0.93(11) . . . . ?
C1 C7 C12 C11 -179.17(7) . . . . ?
C10 C11 C12 C7 0.05(11) . . . . ?
C14 O2 C13 O1 2.14(11) . . . . ?
C14 O2 C13 C10 -176.84(6) . . . . ?
C11 C10 C13 O1 -168.77(8) . . . . ?
C9 C10 C13 O1 9.04(11) . . . . ?
C11 C10 C13 O2 10.22(10) . . . . ?
C9 C10 C13 O2 -171.97(7) . . . . ?
 
_refine_diff_density_max    0.530
_refine_diff_density_min   -0.285
_refine_diff_density_rms    0.054



