#------------------------------------------------------------------------------
#$Date: 2020-04-05 14:11:43 +0300 (Sun, 05 Apr 2020) $
#$Revision: 250364 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/73/7157392.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_7157392
loop_
_publ_author_name
'Pianoski, Karlos Eduardo'
'Poletto, Julia'
'Vieira da Silva, Michael Jackson'
'Ascencio Camargo, Jeniffer Nascimento'
'Jacomini, Andrey Petita'
'Gonçalves, Davana Silva'
'Back, Davi Fernando'
'Moura, Sidnei'
'Rosa, Fernanda Andreia'
_publ_section_title
;
 1,2-Addition to trifluoromethylated β-enamino diketones: regioselective
 synthesis of trifluoromethyl-containing azomethine pyrazoles and
 isoxazoles.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2524
_journal_page_last               2537
_journal_paper_doi               10.1039/d0ob00319k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C24 H17 F4 N3 O'
_chemical_formula_sum            'C24 H17 F4 N3 O'
_chemical_formula_weight         439.41
_chemical_melting_point          ?
_chemical_name_common
'Phenyl trifluormethyl (methyl methoxyphenyl)imin fluorphenyl pyrazol'
_chemical_name_systematic
;
1-Phenyl-3-trifluormethyl-4-(methyl-(2-methoxyphenyl)imin)-5-(4-fluorphenyl)-1H-
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2018-07-09T13:19:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-10-15 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                103.200(2)
_cell_angle_beta                 92.950(2)
_cell_angle_gamma                110.440(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0678(4)
_cell_length_b                   10.6289(5)
_cell_length_c                   11.4690(6)
_cell_measurement_reflns_used    9721
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.172
_cell_measurement_theta_min      2.415
_cell_volume                     997.94(8)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v4.2.7'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Diamond (version 3.2i); Crystal Impact GbR'
_computing_structure_refinement  'SHELXL-2008 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2° φ & ω scans'
_diffrn_radiation_monochromator  'Montel type 2-dim beam shaping X ray optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            51922
_diffrn_reflns_theta_full        29.19
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         2.42
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
        absorption correction based on the indexed faces of the crystal.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0475P)²+0.4512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                4849
_reflns_number_total             5396
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d0ob00319k2.cif
_cod_data_source_block           p-1_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157391--7157393.cif.
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7157392
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F32 F 0.54381(7) 0.61754(7) 0.70451(6) 0.01923(14) Uani 1 1 d . . .
F33 F 0.36665(8) 0.70562(7) 0.74796(6) 0.02027(14) Uani 1 1 d . . .
F31 F 0.29960(8) 0.48335(7) 0.68951(6) 0.02283(15) Uani 1 1 d . . .
F51 F 0.58577(9) 0.88340(8) -0.01749(6) 0.02834(17) Uani 1 1 d . . .
O41 O 0.79231(9) 1.07832(8) 0.49881(7) 0.01834(16) Uani 1 1 d . . .
N1 N 0.24729(10) 0.54206(8) 0.36218(7) 0.01287(16) Uani 1 1 d . . .
N41 N 0.65406(10) 0.88584(8) 0.63574(8) 0.01390(16) Uani 1 1 d . . .
N2 N 0.23919(10) 0.50893(9) 0.47002(7) 0.01399(16) Uani 1 1 d . . .
C3 C 0.36582(11) 0.60684(10) 0.54209(9) 0.01244(17) Uani 1 1 d . . .
C51 C 0.42303(11) 0.71302(10) 0.26081(9) 0.01238(17) Uani 1 1 d . . .
C4 C 0.45824(11) 0.70333(10) 0.48271(8) 0.01209(17) Uani 1 1 d . . .
C5 C 0.37773(11) 0.65665(10) 0.36508(9) 0.01203(17) Uani 1 1 d . . .
C42 C 0.80608(11) 0.99409(10) 0.67130(9) 0.01286(18) Uani 1 1 d . . .
C43 C 0.88067(11) 1.08656(10) 0.60223(9) 0.01379(18) Uani 1 1 d . . .
C41 C 0.60995(11) 0.81967(10) 0.52402(9) 0.01281(18) Uani 1 1 d . . .
H41 H 0.6778 0.8471 0.4665 0.015 Uiso 1 1 calc R . .
C11 C 0.12342(11) 0.45808(10) 0.26338(9) 0.01335(18) Uani 1 1 d . . .
C56 C 0.47145(12) 0.85649(10) 0.27534(9) 0.01534(19) Uani 1 1 d . . .
H56 H 0.4682 0.9149 0.3506 0.018 Uiso 1 1 calc R . .
C52 C 0.42588(12) 0.62739(10) 0.14902(9) 0.01468(18) Uani 1 1 d . . .
H52 H 0.3904 0.5295 0.1376 0.018 Uiso 1 1 calc R . .
C16 C 0.04409(12) 0.52126(11) 0.20388(9) 0.01684(19) Uani 1 1 d . . .
H16 H 0.0715 0.6192 0.2281 0.02 Uiso 1 1 calc R . .
C12 C 0.08512(12) 0.31532(11) 0.22982(9) 0.01658(19) Uani 1 1 d . . .
H12 H 0.1404 0.2737 0.2715 0.02 Uiso 1 1 calc R . .
C53 C 0.48030(12) 0.68463(11) 0.05459(9) 0.0175(2) Uani 1 1 d . . .
H53 H 0.4834 0.6271 -0.0212 0.021 Uiso 1 1 calc R . .
C47 C 0.88390(12) 1.01129(10) 0.78521(9) 0.01616(19) Uani 1 1 d . . .
H47 H 0.831 0.9557 0.8357 0.019 Uiso 1 1 calc R . .
C54 C 0.52987(12) 0.82730(12) 0.07369(9) 0.0184(2) Uani 1 1 d . . .
C46 C 1.03783(13) 1.10853(11) 0.82636(10) 0.0191(2) Uani 1 1 d . . .
H46 H 1.0903 1.1174 0.9034 0.023 Uiso 1 1 calc R . .
C55 C 0.52433(13) 0.91485(11) 0.18099(10) 0.0185(2) Uani 1 1 d . . .
H55 H 0.5557 1.0121 0.1903 0.022 Uiso 1 1 calc R . .
C31 C 0.39379(11) 0.60371(10) 0.67068(9) 0.01428(18) Uani 1 1 d . . .
C45 C 1.11361(12) 1.19200(11) 0.75430(10) 0.0192(2) Uani 1 1 d . . .
H45 H 1.2201 1.2559 0.7806 0.023 Uiso 1 1 calc R . .
C15 C -0.07612(12) 0.43843(12) 0.10824(10) 0.0196(2) Uani 1 1 d . . .
H15 H -0.1319 0.48 0.0669 0.024 Uiso 1 1 calc R . .
C44 C 1.03499(12) 1.18310(10) 0.64338(10) 0.0169(2) Uani 1 1 d . . .
H44 H 1.0867 1.243 0.5956 0.02 Uiso 1 1 calc R . .
C14 C -0.11525(12) 0.29573(12) 0.07274(10) 0.0207(2) Uani 1 1 d . . .
H14 H -0.1964 0.24 0.0065 0.025 Uiso 1 1 calc R . .
C13 C -0.03579(13) 0.23424(11) 0.13402(10) 0.0201(2) Uani 1 1 d . . .
H13 H -0.0642 0.1362 0.1104 0.024 Uiso 1 1 calc R . .
C48 C 0.86820(14) 1.16725(12) 0.42557(10) 0.0220(2) Uani 1 1 d . . .
H48A H 0.7928 1.1517 0.3545 0.033 Uiso 1 1 calc R . .
H48B H 0.9602 1.1465 0.3992 0.033 Uiso 1 1 calc R . .
H48C H 0.9036 1.2646 0.4727 0.033 Uiso 1 1 calc R . .
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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C43 O41 C48 117.31(8) . . ?
N2 N1 C5 112.69(8) . . ?
N2 N1 C11 118.79(8) . . ?
C5 N1 C11 128.52(8) . . ?
C41 N41 C42 119.12(8) . . ?
C3 N2 N1 104.18(8) . . ?
N2 C3 C4 112.72(8) . . ?
N2 C3 C31 118.81(8) . . ?
C4 C3 C31 128.47(9) . . ?
C56 C51 C52 119.19(9) . . ?
C56 C51 C5 119.13(9) . . ?
C52 C51 C5 121.61(9) . . ?
C5 C4 C3 104.01(8) . . ?
C5 C4 C41 124.71(9) . . ?
C3 C4 C41 131.09(9) . . ?
N1 C5 C4 106.38(8) . . ?
N1 C5 C51 125.17(8) . . ?
C4 C5 C51 128.42(9) . . ?
C47 C42 C43 118.50(9) . . ?
C47 C42 N41 116.32(9) . . ?
C43 C42 N41 125.15(9) . . ?
O41 C43 C44 123.48(9) . . ?
O41 C43 C42 116.69(8) . . ?
C44 C43 C42 119.79(9) . . ?
N41 C41 C4 121.66(9) . . ?
C12 C11 C16 121.62(9) . . ?
C12 C11 N1 119.04(9) . . ?
C16 C11 N1 119.33(9) . . ?
C55 C56 C51 120.89(9) . . ?
C53 C52 C51 120.44(9) . . ?
C11 C16 C15 118.72(10) . . ?
C11 C12 C13 118.75(10) . . ?
C54 C53 C52 118.41(9) . . ?
C46 C47 C42 121.24(10) . . ?
F51 C54 C55 118.55(10) . . ?
F51 C54 C53 118.44(10) . . ?
C55 C54 C53 123.01(10) . . ?
C45 C46 C47 119.49(10) . . ?
C54 C55 C56 118.01(9) . . ?
F33 C31 F31 106.99(8) . . ?
F33 C31 F32 106.71(8) . . ?
F31 C31 F32 106.35(8) . . ?
F33 C31 C3 112.33(8) . . ?
F31 C31 C3 111.78(8) . . ?
F32 C31 C3 112.28(8) . . ?
C46 C45 C44 120.45(9) . . ?
C14 C15 C16 120.50(10) . . ?
C45 C44 C43 120.20(10) . . ?
C15 C14 C13 119.97(10) . . ?
C14 C13 C12 120.41(10) . . ?
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
F32 C31 1.3426(11) . ?
F33 C31 1.3378(12) . ?
F31 C31 1.3397(11) . ?
F51 C54 1.3544(12) . ?
O41 C43 1.3646(12) . ?
O41 C48 1.4284(12) . ?
N1 N2 1.3599(11) . ?
N1 C5 1.3619(12) . ?
N1 C11 1.4315(12) . ?
N41 C41 1.2788(13) . ?
N41 C42 1.4179(12) . ?
N2 C3 1.3265(12) . ?
C3 C4 1.4126(13) . ?
C3 C31 1.4934(13) . ?
C51 C56 1.3981(13) . ?
C51 C52 1.3999(13) . ?
C51 C5 1.4709(13) . ?
C4 C5 1.3925(13) . ?
C4 C41 1.4572(13) . ?
C42 C47 1.3943(14) . ?
C42 C43 1.4133(13) . ?
C43 C44 1.3935(13) . ?
C11 C12 1.3866(14) . ?
C11 C16 1.3893(14) . ?
C56 C55 1.3921(14) . ?
C52 C53 1.3902(14) . ?
C16 C15 1.3900(14) . ?
C12 C13 1.3913(14) . ?
C53 C54 1.3826(15) . ?
C47 C46 1.3932(14) . ?
C54 C55 1.3780(15) . ?
C46 C45 1.3820(16) . ?
C45 C44 1.3928(15) . ?
C15 C14 1.3855(16) . ?
C14 C13 1.3881(16) . ?
