#------------------------------------------------------------------------------
#$Date: 2016-05-21 04:40:00 +0300 (Sat, 21 May 2016) $
#$Revision: 183064 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/33/1543348.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1543348
loop_
_publ_author_name
'Atalay, Şehriman'
'Gerçeker, Semra'
'Meral, Seher'
'Alaman Ağar, Ayşen'
_publ_section_title
;
 2-Amino-3-((E)-{[3-(trifluoromethyl)phenyl]imino}methyl)-4H-chromen-4-one
;
_journal_coeditor_code           HB4046
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x160797
_journal_paper_doi               10.1107/S2414314616007975
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C17 H11 F3 N2 O2'
_chemical_formula_moiety         'C17 H11 F3 N2 O2'
_chemical_formula_sum            'C17 H11 F3 N2 O2'
_chemical_formula_weight         332.28
_chemical_name_systematic
2-Amino-3-((E)-{[3-(trifluoromethyl)phenyl]imino}methyl)-4H-chromen-4-one
_space_group_IT_number           2
_space_group_name_Hall           '-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_creation_method           SHELXL-97
_cell_angle_alpha                99.626(9)
_cell_angle_beta                 91.602(9)
_cell_angle_gamma                105.020(8)
_cell_formula_units_Z            2
_cell_length_a                   7.1355(7)
_cell_length_b                   7.4786(8)
_cell_length_c                   14.8254(18)
_cell_measurement_reflns_used    10185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.79
_cell_volume                     751.23(15)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10651
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9278
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0487
_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)+(0.0712P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                1943
_reflns_number_total             3459
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb4046sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        751.23(14)
_cod_database_code               1543348
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
F F1 1.1149(3) 1.2500(3) 1.04420(11) 0.1398(7) Uani d . 1 1
F F2 1.3145(3) 1.3841(3) 0.96186(14) 0.1488(8) Uani d . 1 1
F F3 1.2718(3) 1.0977(3) 0.96031(12) 0.1440(8) Uani d . 1 1
O O1 1.00027(15) 0.60607(17) 0.39411(8) 0.0605(3) Uani d . 1 1
O O2 0.48054(19) 0.7063(3) 0.45522(12) 0.1060(6) Uani d . 1 1
N N1 0.9386(2) 0.9435(2) 0.64656(11) 0.0635(4) Uani d . 1 1
N N2 1.1497(2) 0.7799(2) 0.52389(13) 0.0636(4) Uani d . 1 1
H H2A 1.149(3) 0.848(3) 0.5759(15) 0.067(6) Uiso d . 1 1
H H2B 1.257(3) 0.754(3) 0.5005(15) 0.080(6) Uiso d . 1 1
C C1 1.1803(4) 1.2277(3) 0.96150(17) 0.0885(7) Uani d . 1 1
C C2 1.0264(3) 1.1879(3) 0.88641(15) 0.0722(5) Uani d . 1 1
C C3 0.8666(3) 1.2580(3) 0.90000(16) 0.0826(6) Uani d . 1 1
H H3 0.8517 1.3240 0.9571 0.099 Uiso calc R 1 1
C C4 0.7307(3) 1.2296(3) 0.82875(17) 0.0864(7) Uani d . 1 1
H H4 0.6242 1.2790 0.8375 0.104 Uiso calc R 1 1
C C5 0.7485(3) 1.1285(3) 0.74360(15) 0.0750(6) Uani d . 1 1
H H5 0.6554 1.1117 0.6955 0.090 Uiso calc R 1 1
C C6 0.9068(3) 1.0518(2) 0.73012(13) 0.0628(5) Uani d . 1 1
C C7 1.0465(3) 1.0860(3) 0.80176(14) 0.0670(5) Uani d . 1 1
H H7 1.1553 1.0402 0.7932 0.080 Uiso calc R 1 1
C C8 0.7961(3) 0.8608(3) 0.58759(13) 0.0632(5) Uani d . 1 1
H H8 0.6741 0.8746 0.6021 0.076 Uiso calc R 1 1
C C9 0.8082(2) 0.7480(2) 0.50068(13) 0.0578(4) Uani d . 1 1
C C10 0.9849(2) 0.7136(2) 0.47434(12) 0.0542(4) Uani d . 1 1
C C11 0.8380(2) 0.5221(2) 0.33411(13) 0.0590(4) Uani d . 1 1
C C12 0.8643(3) 0.4088(3) 0.25495(15) 0.0741(5) Uani d . 1 1
H H12 0.9866 0.3919 0.2434 0.089 Uiso calc R 1 1
C C13 0.7079(4) 0.3218(3) 0.19368(16) 0.0855(6) Uani d . 1 1
H H13 0.7241 0.2460 0.1396 0.103 Uiso calc R 1 1
C C14 0.5251(4) 0.3453(3) 0.21125(17) 0.0893(7) Uani d . 1 1
H H14 0.4190 0.2840 0.1695 0.107 Uiso calc R 1 1
C C15 0.5009(3) 0.4590(3) 0.29012(16) 0.0807(6) Uani d . 1 1
H H15 0.3781 0.4750 0.3014 0.097 Uiso calc R 1 1
C C16 0.6580(2) 0.5510(3) 0.35376(13) 0.0631(5) Uani d . 1 1
C C17 0.6385(2) 0.6731(3) 0.43930(14) 0.0682(5) Uani d . 1 1
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'
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 0.0060 '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
C10 O1 C11 120.17(13)
C8 N1 C6 119.83(15)
C10 N2 H2A 117.3(13)
C10 N2 H2B 118.3(13)
H2A N2 H2B 124.4(19)
F3 C1 F2 105.9(2)
F3 C1 F1 105.4(2)
F2 C1 F1 104.0(2)
F3 C1 C2 114.44(19)
F2 C1 C2 112.9(2)
F1 C1 C2 113.3(2)
C3 C2 C7 120.3(2)
C3 C2 C1 119.7(2)
C7 C2 C1 119.89(19)
C4 C3 C2 119.3(2)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C5 121.1(2)
C3 C4 H4 119.4
C5 C4 H4 119.4
C4 C5 C6 119.8(2)
C4 C5 H5 120.1
C6 C5 H5 120.1
C7 C6 C5 118.56(18)
C7 C6 N1 116.63(16)
C5 C6 N1 124.79(18)
C6 C7 C2 120.72(18)
C6 C7 H7 119.6
C2 C7 H7 119.6
N1 C8 C9 125.45(16)
N1 C8 H8 117.3
C9 C8 H8 117.3
C10 C9 C17 119.43(17)
C10 C9 C8 121.30(16)
C17 C9 C8 119.25(15)
N2 C10 O1 112.79(14)
N2 C10 C9 124.50(17)
O1 C10 C9 122.71(15)
C12 C11 O1 116.69(16)
C12 C11 C16 122.26(18)
O1 C11 C16 121.05(16)
C13 C12 C11 118.85(19)
C13 C12 H12 120.6
C11 C12 H12 120.6
C12 C13 C14 120.7(2)
C12 C13 H13 119.7
C14 C13 H13 119.7
C15 C14 C13 119.9(2)
C15 C14 H14 120.0
C13 C14 H14 120.0
C14 C15 C16 120.8(2)
C14 C15 H15 119.6
C16 C15 H15 119.6
C11 C16 C15 117.49(19)
C11 C16 C17 119.89(16)
C15 C16 C17 122.62(17)
O2 C17 C9 123.26(19)
O2 C17 C16 120.15(18)
C9 C17 C16 116.60(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C1 1.324(3)
F2 C1 1.304(3)
F3 C1 1.302(3)
O1 C10 1.344(2)
O1 C11 1.380(2)
O2 C17 1.236(2)
N1 C8 1.275(2)
N1 C6 1.420(2)
N2 C10 1.302(2)
N2 H2A 0.85(2)
N2 H2B 0.90(2)
C1 C2 1.479(3)
C2 C3 1.379(3)
C2 C7 1.387(3)
C3 C4 1.365(3)
C3 H3 0.9300
C4 C5 1.386(3)
C4 H4 0.9300
C5 C6 1.399(3)
C5 H5 0.9300
C6 C7 1.380(3)
C7 H7 0.9300
C8 C9 1.435(3)
C8 H8 0.9300
C9 C10 1.404(2)
C9 C17 1.423(3)
C11 C12 1.375(3)
C11 C16 1.388(2)
C12 C13 1.365(3)
C12 H12 0.9300
C13 C14 1.387(3)
C13 H13 0.9300
C14 C15 1.369(3)
C14 H14 0.9300
C15 C16 1.395(3)
C15 H15 0.9300
C16 C17 1.466(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A N1 . 0.85(2) 2.06(2) 2.727(2) 134.4(16)
N2 H2B O2 1_655 0.90(2) 1.84(2) 2.745(2) 178(2)
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
F3 C1 C2 C3 150.4(2)
F2 C1 C2 C3 -88.4(3)
F1 C1 C2 C3 29.6(3)
F3 C1 C2 C7 -31.8(3)
F2 C1 C2 C7 89.4(3)
F1 C1 C2 C7 -152.7(2)
C7 C2 C3 C4 -1.4(3)
C1 C2 C3 C4 176.3(2)
C2 C3 C4 C5 1.3(4)
C3 C4 C5 C6 0.8(3)
C4 C5 C6 C7 -2.7(3)
C4 C5 C6 N1 178.99(19)
C8 N1 C6 C7 159.66(18)
C8 N1 C6 C5 -22.0(3)
C5 C6 C7 C2 2.5(3)
N1 C6 C7 C2 -179.00(17)
C3 C2 C7 C6 -0.5(3)
C1 C2 C7 C6 -178.25(19)
C6 N1 C8 C9 179.79(18)
N1 C8 C9 C10 2.3(3)
N1 C8 C9 C17 -176.31(19)
C11 O1 C10 N2 178.83(15)
C11 O1 C10 C9 -0.9(2)
C17 C9 C10 N2 177.86(18)
C8 C9 C10 N2 -0.8(3)
C17 C9 C10 O1 -2.5(3)
C8 C9 C10 O1 178.87(16)
C10 O1 C11 C12 -177.75(16)
C10 O1 C11 C16 2.0(2)
O1 C11 C12 C13 179.66(19)
C16 C11 C12 C13 -0.1(3)
C11 C12 C13 C14 -0.7(3)
C12 C13 C14 C15 1.0(4)
C13 C14 C15 C16 -0.4(4)
C12 C11 C16 C15 0.6(3)
O1 C11 C16 C15 -179.16(18)
C12 C11 C16 C17 179.95(18)
O1 C11 C16 C17 0.2(3)
C14 C15 C16 C11 -0.3(3)
C14 C15 C16 C17 -179.7(2)
C10 C9 C17 O2 -175.6(2)
C8 C9 C17 O2 3.0(3)
C10 C9 C17 C16 4.4(3)
C8 C9 C17 C16 -176.88(17)
C11 C16 C17 O2 176.7(2)
C15 C16 C17 O2 -4.0(3)
C11 C16 C17 C9 -3.4(3)
C15 C16 C17 C9 175.96(19)

_cod_database_fobs_code 1543348
