#------------------------------------------------------------------------------
#$Date: 2020-04-05 14:11:43 +0300 (Sun, 05 Apr 2020) $
#$Revision: 250364 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/73/7157393.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_7157393
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         'C18 H12 Br F3 N2 O2'
_chemical_formula_sum            'C18 H12 Br F3 N2 O2'
_chemical_formula_weight         425.21
_chemical_melting_point          ?
_chemical_name_common
'trifluormethyl methoxyphenyl iminomethyl bromophenyl isoxal'
_chemical_name_systematic
;
3-trifluormethyl-4-(2-methoxyphenyl)iminomethyl-5-(4-bromophenyl)-isoxal
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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             2019-10-15T14:35:19-00:00
_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                90
_cell_angle_beta                 97.851(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.889(2)
_cell_length_b                   5.2686(10)
_cell_length_c                   25.153(5)
_cell_measurement_reflns_used    3977
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.751
_cell_measurement_theta_min      2.737
_cell_volume                     1692.1(5)
_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      295(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  0.0438
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14746
_diffrn_reflns_theta_full        27.2
_diffrn_reflns_theta_max         27.2
_diffrn_reflns_theta_min         2.74
_diffrn_source                   'micro-focus tube'
_exptl_absorpt_coefficient_mu    2.476
_exptl_absorpt_correction_T_max  0.7177
_exptl_absorpt_correction_T_min  0.5753
_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    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0463
_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)+(0.0545P)²+0.8323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1231
_reflns_number_gt                2246
_reflns_number_total             3750
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d0ob00319k2.cif
_cod_data_source_block           dfbkibri_0m_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_cell_volume        1692.0(5)
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7157393
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br51 Br 0.18041(3) 0.70048(10) 0.297832(18) 0.0869(2) Uani 1 1 d . . .
O41 O 0.63754(15) 1.1490(4) 0.32186(8) 0.0536(6) Uani 1 1 d . . .
O1 O 0.56875(18) 0.2176(4) 0.47664(10) 0.0601(6) Uani 1 1 d . . .
F31 F 0.87202(19) 0.5062(5) 0.54447(10) 0.0981(8) Uani 1 1 d . . .
N41 N 0.72155(19) 0.7907(5) 0.38713(11) 0.0524(7) Uani 1 1 d . . .
F32 F 0.90553(19) 0.2447(6) 0.48713(10) 0.1121(10) Uani 1 1 d . . .
C42 C 0.7899(2) 0.9589(5) 0.36532(11) 0.0397(7) Uani 1 1 d . . .
N2 N 0.6618(2) 0.1573(6) 0.50852(11) 0.0621(8) Uani 1 1 d . . .
C51 C 0.4886(2) 0.4849(6) 0.40777(11) 0.0432(7) Uani 1 1 d . . .
C43 C 0.7440(2) 1.1454(5) 0.33020(10) 0.0396(7) Uani 1 1 d . . .
F33 F 0.8505(2) 0.1196(6) 0.55816(12) 0.1308(12) Uani 1 1 d . . .
C4 C 0.6876(2) 0.4796(5) 0.45189(11) 0.0401(6) Uani 1 1 d . . .
C5 C 0.5837(2) 0.4113(6) 0.44272(11) 0.0433(7) Uani 1 1 d . . .
C47 C 0.8982(2) 0.9446(7) 0.37488(12) 0.0528(8) Uani 1 1 d . . .
H47 H 0.9295 0.8188 0.3976 0.063 Uiso 1 1 calc R . .
C41 C 0.7497(2) 0.6650(6) 0.42725(12) 0.0496(8) Uani 1 1 d . . .
H41 H 0.818 0.6904 0.4438 0.06 Uiso 1 1 calc R . .
C56 C 0.4840(2) 0.6991(6) 0.37583(13) 0.0502(8) Uani 1 1 d . . .
H56 H 0.5427 0.8023 0.3766 0.06 Uiso 1 1 calc R . .
C54 C 0.3063(2) 0.6087(7) 0.34232(13) 0.0542(8) Uani 1 1 d . . .
C46 C 0.9606(2) 1.1118(7) 0.35160(13) 0.0555(8) Uani 1 1 d . . .
H46 H 1.0332 1.0998 0.3587 0.067 Uiso 1 1 calc R . .
C55 C 0.3930(2) 0.7609(7) 0.34287(14) 0.0560(8) Uani 1 1 d . . .
H55 H 0.3904 0.9044 0.3212 0.067 Uiso 1 1 calc R . .
C44 C 0.8069(3) 1.3123(6) 0.30666(13) 0.0508(8) Uani 1 1 d . . .
H44 H 0.7766 1.4363 0.2832 0.061 Uiso 1 1 calc R . .
C45 C 0.9151(3) 1.2953(6) 0.31799(14) 0.0562(8) Uani 1 1 d . . .
H45 H 0.9569 1.4101 0.3025 0.067 Uiso 1 1 calc R . .
C3 C 0.7301(3) 0.3114(6) 0.49362(12) 0.0488(7) Uani 1 1 d . . .
C52 C 0.3992(3) 0.3359(6) 0.40680(14) 0.0578(9) Uani 1 1 d . . .
H52 H 0.4006 0.1934 0.4287 0.069 Uiso 1 1 calc R . .
C53 C 0.3085(3) 0.3978(7) 0.37360(15) 0.0639(9) Uani 1 1 d . . .
H53 H 0.2493 0.296 0.3726 0.077 Uiso 1 1 calc R . .
C48 C 0.5883(3) 1.3332(7) 0.28528(13) 0.0579(8) Uani 1 1 d . . .
H48A H 0.5136 1.3165 0.2828 0.087 Uiso 1 1 calc R . .
H48B H 0.6092 1.3068 0.2505 0.087 Uiso 1 1 calc R . .
H48C H 0.6087 1.5002 0.2978 0.087 Uiso 1 1 calc R . .
C31 C 0.8393(3) 0.2940(8) 0.52056(15) 0.0635(9) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 117.4(2) . . ?
C5 O1 N2 110.5(2) . . ?
C41 N41 C42 122.1(3) . . ?
C47 C42 C43 118.5(3) . . ?
C47 C42 N41 124.4(3) . . ?
C43 C42 N41 117.0(2) . . ?
C3 N2 O1 105.0(2) . . ?
C56 C51 C52 118.8(3) . . ?
C56 C51 C5 122.2(3) . . ?
C52 C51 C5 119.0(3) . . ?
O41 C43 C44 124.3(3) . . ?
O41 C43 C42 116.0(2) . . ?
C44 C43 C42 119.7(3) . . ?
C5 C4 C3 103.2(3) . . ?
C5 C4 C41 133.2(3) . . ?
C3 C4 C41 123.6(3) . . ?
O1 C5 C4 108.0(3) . . ?
O1 C5 C51 113.5(3) . . ?
C4 C5 C51 138.5(3) . . ?
C46 C47 C42 121.6(3) . . ?
N41 C41 C4 126.7(3) . . ?
C55 C56 C51 120.5(3) . . ?
C53 C54 C55 121.2(3) . . ?
C53 C54 Br51 119.8(3) . . ?
C55 C54 Br51 119.0(3) . . ?
C45 C46 C47 119.4(3) . . ?
C54 C55 C56 119.5(3) . . ?
C43 C44 C45 120.2(3) . . ?
C46 C45 C44 120.6(3) . . ?
N2 C3 C4 113.3(3) . . ?
N2 C3 C31 118.2(3) . . ?
C4 C3 C31 128.5(3) . . ?
C53 C52 C51 120.5(3) . . ?
C54 C53 C52 119.5(3) . . ?
F32 C31 F31 105.6(3) . . ?
F32 C31 F33 108.0(3) . . ?
F31 C31 F33 105.6(3) . . ?
F32 C31 C3 112.5(3) . . ?
F31 C31 C3 112.5(3) . . ?
F33 C31 C3 112.2(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
Br51 C54 1.903(3) . ?
O41 C43 1.359(3) . ?
O41 C48 1.425(4) . ?
O1 C5 1.361(4) . ?
O1 N2 1.386(4) . ?
F31 C31 1.311(4) . ?
N41 C41 1.220(4) . ?
N41 C42 1.412(4) . ?
F32 C31 1.303(4) . ?
C42 C47 1.386(4) . ?
C42 C43 1.398(4) . ?
N2 C3 1.290(4) . ?
C51 C56 1.382(4) . ?
C51 C52 1.392(4) . ?
C51 C5 1.460(4) . ?
C43 C44 1.383(4) . ?
F33 C31 1.312(4) . ?
C4 C5 1.376(4) . ?
C4 C3 1.425(4) . ?
C4 C41 1.455(4) . ?
C47 C46 1.377(4) . ?
C56 C55 1.380(4) . ?
C54 C53 1.360(5) . ?
C54 C55 1.374(5) . ?
C46 C45 1.363(5) . ?
C44 C45 1.387(5) . ?
C3 C31 1.479(5) . ?
C52 C53 1.380(5) . ?
