#------------------------------------------------------------------------------
#$Date: 2019-11-23 15:38:11 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/60/7236044.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_7236044
loop_
_publ_author_name
'Sosnovskikh, Vyacheslav Y.'
'Safrygin, Alexander V.'
'Irgashev, Roman A.'
'Ezhikova, Marina A.'
'Kodess, Mikhail I.'
_publ_section_title
;
 Synthesis of 4-arylamino-3-(trifluoromethyl)pyridazines and
 pyridazino[3,4-b]quinoxalines (as by-products) from
 3-aroylmethyl-2-(trifluoromethyl)quinoxalines and hydrazine hydrate
;
_journal_issue                   36
_journal_name_full               'RSC Advances'
_journal_page_first              30056
_journal_paper_doi               10.1039/C5RA27032D
_journal_volume                  6
_journal_year                    2016
_chemical_formula_sum            'C19 H17 F3 N5 O'
_chemical_formula_weight         388.38
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-20 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.746(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0546(15)
_cell_length_b                   19.664(3)
_cell_length_c                   17.9966(16)
_cell_measurement_reflns_used    1557
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.80
_cell_volume                     3765.3(9)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET)
(compiled Mar 23 2006,23:39:28)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Xcalibur S CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.1174
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8604
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.032
_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     273
_refine_ls_number_reflns         4349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0170P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                1557
_reflns_number_total             4349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra27032d2.cif
_cod_data_source_block           dc
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        3765.3(8)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7236044
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
F1 F 0.37098(11) 0.12863(7) 0.20386(8) 0.1028(5) Uani 1 1 d .
N1 N 0.03336(14) -0.00691(8) 0.15574(9) 0.0506(4) Uani 1 1 d .
O1 O 0.33685(12) 0.28564(7) 0.19096(7) 0.0647(4) Uani 1 1 d .
C1 C 0.35099(18) 0.32578(10) 0.24400(11) 0.0456(5) Uani 1 1 d .
N2 N 0.14125(15) 0.01849(8) 0.19868(9) 0.0568(5) Uani 1 1 d .
F2 F 0.28049(15) 0.15201(9) 0.28823(8) 0.1345(6) Uani 1 1 d .
C2 C 0.25598(18) 0.33648(11) 0.28762(12) 0.0791(7) Uani 1 1 d .
H2A H 0.1846 0.3078 0.2667 0.119 Uiso 1 1 calc R
H2B H 0.2298 0.3832 0.2833 0.119 Uiso 1 1 calc R
H2C H 0.2922 0.3254 0.3410 0.119 Uiso 1 1 calc R
N3 N 0.13365(15) 0.19096(8) 0.12468(9) 0.0493(4) Uani 1 1 d .
C3 C 0.17349(17) 0.08103(10) 0.18933(10) 0.0496(5) Uani 1 1 d .
F3 F 0.35645(13) 0.05401(8) 0.28453(9) 0.1534(8) Uani 1 1 d .
C4 C 0.10027(17) 0.12669(10) 0.13455(10) 0.0441(5) Uani 1 1 d .
N4 N 0.1185(3) 0.19206(12) -0.03289(16) 0.0942(8) Uani 1 1 d .
C5 C -0.01199(18) 0.09911(10) 0.09164(11) 0.0438(5) Uani 1 1 d .
N5 N 0.45393(14) 0.36348(8) 0.26926(9) 0.0440(4) Uani 1 1 d .
C6 C -0.04238(16) 0.03357(9) 0.10286(10) 0.0413(5) Uani 1 1 d .
C7 C 0.2954(2) 0.10233(15) 0.24202(16) 0.0837(8) Uani 1 1 d .
C8 C -0.16054(16) 0.00341(9) 0.05761(12) 0.0440(5) Uani 1 1 d .
C9 C -0.22611(18) -0.04082(10) 0.09104(12) 0.0605(6) Uani 1 1 d .
H9A H -0.1946 -0.0524 0.1428 0.073 Uiso 1 1 calc R
C10 C -0.3379(2) -0.06808(11) 0.04864(15) 0.0770(7) Uani 1 1 d .
H10A H -0.3818 -0.0981 0.0717 0.092 Uiso 1 1 calc R
C11 C -0.3845(2) -0.05117(11) -0.02739(16) 0.0767(7) Uani 1 1 d .
H11A H -0.4605 -0.0695 -0.0559 0.092 Uiso 1 1 calc R
C12 C -0.3206(2) -0.00784(11) -0.06146(12) 0.0684(6) Uani 1 1 d .
H12A H -0.3525 0.0035 -0.1133 0.082 Uiso 1 1 calc R
C13 C -0.20834(17) 0.01939(9) -0.01925(12) 0.0542(5) Uani 1 1 d .
H13A H -0.1644 0.0489 -0.0429 0.065 Uiso 1 1 calc R
C14 C 0.05020(17) 0.23552(9) 0.07255(11) 0.0419(5) Uani 1 1 d .
C15 C 0.04689(19) 0.23548(10) -0.00494(12) 0.0495(5) Uani 1 1 d .
C16 C -0.0372(2) 0.27896(11) -0.05378(11) 0.0607(6) Uani 1 1 d .
H16A H -0.0403 0.2802 -0.1059 0.073 Uiso 1 1 calc R
C17 C -0.1140(2) 0.31933(11) -0.02708(14) 0.0675(7) Uani 1 1 d .
H17A H -0.1700 0.3479 -0.0610 0.081 Uiso 1 1 calc R
C18 C -0.1110(2) 0.31891(11) 0.04902(16) 0.0744(7) Uani 1 1 d .
H18A H -0.1643 0.3469 0.0673 0.089 Uiso 1 1 calc R
C19 C -0.0282(2) 0.27663(11) 0.09836(11) 0.0592(6) Uani 1 1 d .
H19A H -0.0257 0.2761 0.1504 0.071 Uiso 1 1 calc R
H5A H -0.0697(13) 0.1283(7) 0.0568(8) 0.035(5) Uiso 1 1 d .
H5 H 0.4583(15) 0.4024(9) 0.3010(9) 0.067(6) Uiso 1 1 d .
H4A H 0.1775(17) 0.1720(10) -0.0022(11) 0.066(8) Uiso 1 1 d .
H4B H 0.130(2) 0.1995(11) -0.0797(13) 0.101(10) Uiso 1 1 d .
H3 H 0.2086(15) 0.2107(8) 0.1543(9) 0.059(6) 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'
O O 0.0106 0.0060 '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'
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
N2 N1 C6 118.48(16) . .
O1 C1 N5 123.08(18) . .
O1 C1 C2 123.21(19) . .
N5 C1 C2 113.70(18) . .
C3 N2 N1 120.84(16) . .
C1 C2 H2A 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
C1 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
C4 N3 C14 120.95(16) . .
C4 N3 H3 123.1(10) . .
C14 N3 H3 115.7(10) . .
N2 C3 C4 124.33(17) . .
N2 C3 C7 114.65(19) . .
C4 C3 C7 121.0(2) . .
N3 C4 C5 122.22(18) . .
N3 C4 C3 124.35(17) . .
C5 C4 C3 113.42(19) . .
C15 N4 H4A 119.1(15) . .
C15 N4 H4B 119.6(15) . .
H4A N4 H4B 114(2) . .
C6 C5 C4 120.60(19) . .
C6 C5 H5A 121.2(9) . .
C4 C5 H5A 118.0(9) . .
C1 N5 N5 120.55(17) . 2_655
C1 N5 H5 123.7(11) . .
N5 N5 H5 112.3(10) 2_655 .
N1 C6 C5 122.30(18) . .
N1 C6 C8 116.37(17) . .
C5 C6 C8 121.33(18) . .
F3 C7 F1 107.1(2) . .
F3 C7 F2 107.8(2) . .
F1 C7 F2 104.0(2) . .
F3 C7 C3 114.2(2) . .
F1 C7 C3 111.8(2) . .
F2 C7 C3 111.3(2) . .
C9 C8 C13 118.76(17) . .
C9 C8 C6 120.72(19) . .
C13 C8 C6 120.52(18) . .
C8 C9 C10 120.5(2) . .
C8 C9 H9A 119.8 . .
C10 C9 H9A 119.8 . .
C11 C10 C9 120.0(2) . .
C11 C10 H10A 120.0 . .
C9 C10 H10A 120.0 . .
C12 C11 C10 120.3(2) . .
C12 C11 H11A 119.8 . .
C10 C11 H11A 119.8 . .
C11 C12 C13 119.9(2) . .
C11 C12 H12A 120.1 . .
C13 C12 H12A 120.1 . .
C8 C13 C12 120.60(19) . .
C8 C13 H13A 119.7 . .
C12 C13 H13A 119.7 . .
C19 C14 C15 120.03(18) . .
C19 C14 N3 120.07(18) . .
C15 C14 N3 119.88(19) . .
N4 C15 C14 121.1(2) . .
N4 C15 C16 120.9(2) . .
C14 C15 C16 117.9(2) . .
C17 C16 C15 121.2(2) . .
C17 C16 H16A 119.4 . .
C15 C16 H16A 119.4 . .
C16 C17 C18 120.7(2) . .
C16 C17 H17A 119.6 . .
C18 C17 H17A 119.6 . .
C17 C18 C19 119.1(2) . .
C17 C18 H18A 120.5 . .
C19 C18 H18A 120.5 . .
C14 C19 C18 121.10(19) . .
C14 C19 H19A 119.4 . .
C18 C19 H19A 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C7 1.322(3) .
N1 N2 1.3300(18) .
N1 C6 1.3445(19) .
O1 C1 1.2156(19) .
C1 N5 1.331(2) .
C1 C2 1.487(2) .
N2 C3 1.304(2) .
F2 C7 1.322(3) .
C2 H2A 0.9600 .
C2 H2B 0.9600 .
C2 H2C 0.9600 .
N3 C4 1.342(2) .
N3 C14 1.424(2) .
N3 H3 0.939(16) .
C3 C4 1.414(2) .
C3 C7 1.483(3) .
F3 C7 1.290(2) .
C4 C5 1.382(2) .
N4 C15 1.351(3) .
N4 H4A 0.830(17) .
N4 H4B 0.90(2) .
C5 C6 1.361(2) .
C5 H5A 0.954(14) .
N5 N5 1.379(3) 2_655
N5 H5 0.948(17) .
C6 C8 1.464(2) .
C8 C9 1.371(2) .
C8 C13 1.376(2) .
C9 C10 1.373(2) .
C9 H9A 0.9300 .
C10 C11 1.366(3) .
C10 H10A 0.9300 .
C11 C12 1.355(3) .
C11 H11A 0.9300 .
C12 C13 1.375(2) .
C12 H12A 0.9300 .
C13 H13A 0.9300 .
C14 C19 1.356(2) .
C14 C15 1.385(2) .
C15 C16 1.387(2) .
C16 C17 1.343(2) .
C16 H16A 0.9300 .
C17 C18 1.361(3) .
C17 H17A 0.9300 .
C18 C19 1.370(3) .
C18 H18A 0.9300 .
C19 H19A 0.9300 .
