#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:49:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179025 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/23/4122377.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_4122377
loop_
_publ_author_name
'Constantinides, Christos P.'
'Berezin, Andrey A.'
'Zissimou, Georgia A.'
'Manoli, Maria'
'Leitus, Gregory M.'
'Bendikov, Michael'
'Probert, Michael R.'
'Rawson, Jeremy M.'
'Koutentis, Panayiotis A.'
_publ_section_title
;
 A Magnetostructural Investigation of an Abrupt Spin Transition for
 1-Phenyl-3-trifluoromethyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11906
_journal_paper_doi               10.1021/ja5063746
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C14 H9 F3 N3'
_chemical_formula_sum            'C14 H9 F3 N3'
_chemical_formula_weight         276.24
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-04-01
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.03.19 svn.r2915 for OlexSys, GUI svn.r4811)
;
_cell_angle_alpha                79.778(2)
_cell_angle_beta                 67.137(2)
_cell_angle_gamma                86.490(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2531(4)
_cell_length_b                   8.6096(4)
_cell_length_c                   9.5178(4)
_cell_measurement_reflns_used    6863
_cell_measurement_temperature    75.0
_cell_measurement_theta_max      26.45
_cell_measurement_theta_min      2.36
_cell_volume                     613.25(5)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      75.0
_diffrn_detector                 'Bruker APEX-II CCD area detector'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.809
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measurement_device       'XIPHOS four-circle diffractometer'
_diffrn_measurement_device_type  Xiphos
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support '0.5mm graphite fibre'
_diffrn_radiation_collimation    focused
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.809
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9462
_diffrn_reflns_point_group_measured_fraction_full 0.809
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.449
_diffrn_reflns_theta_min         2.355
_diffrn_source                   'Bruker TXS with Helios Optics'
_diffrn_source_current           75.0
_diffrn_source_power             3.75
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0966 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.8758.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dark black'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       needle
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0224P)²+0.4491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1741
_reflns_number_total             2036
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5063746_si_003.cif
_cod_data_source_block           data75k
_cod_depositor_comments
'Adding full bibliography for 4122377--4122379.cif.'
_cod_database_code               4122377
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-4
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F1 F 0.05913(16) 0.64549(12) 0.92406(11) 0.0302(3) Uani 1 1 d .
F2 F 0.23543(17) 0.84341(12) 0.81587(10) 0.0263(3) Uani 1 1 d .
F3 F -0.04004(15) 0.88063(13) 0.94151(11) 0.0298(3) Uani 1 1 d .
N1 N 0.1429(2) 0.75199(16) 0.45404(14) 0.0180(4) Uani 1 1 d .
N2 N 0.1739(2) 0.75404(16) 0.58502(14) 0.0186(4) Uani 1 1 d .
N3 N -0.1241(2) 0.83765(16) 0.71150(14) 0.0190(4) Uani 1 1 d .
C1 C 0.0363(2) 0.79705(18) 0.70076(17) 0.0172(4) Uani 1 1 d .
C2 C -0.1570(3) 0.82442(18) 0.58180(17) 0.0181(4) Uani 1 1 d .
C3 C -0.3246(3) 0.85339(19) 0.58220(18) 0.0207(4) Uani 1 1 d .
H3 H -0.4144 0.8867 0.6695 0.025 Uiso 1 1 calc R
C4 C -0.3618(3) 0.83419(19) 0.45677(19) 0.0221(4) Uani 1 1 d .
H4 H -0.4769 0.8537 0.4582 0.027 Uiso 1 1 calc R
C5 C -0.2297(3) 0.78608(19) 0.32791(18) 0.0233(5) Uani 1 1 d .
H5 H -0.2562 0.7730 0.2420 0.028 Uiso 1 1 calc R
C6 C -0.0620(3) 0.75730(19) 0.32317(17) 0.0211(4) Uani 1 1 d .
H6 H 0.0264 0.7237 0.2352 0.025 Uiso 1 1 calc R
C7 C -0.0229(2) 0.77800(18) 0.44933(17) 0.0177(4) Uani 1 1 d .
C8 C 0.2926(2) 0.70792(19) 0.32721(17) 0.0179(4) Uani 1 1 d .
C9 C 0.3499(3) 0.8069(2) 0.18463(18) 0.0217(4) Uani 1 1 d .
H9 H 0.2913 0.9032 0.1700 0.026 Uiso 1 1 calc R
C10 C 0.4944(3) 0.7620(2) 0.06402(18) 0.0238(5) Uani 1 1 d .
H10 H 0.5352 0.8280 -0.0344 0.029 Uiso 1 1 calc R
C11 C 0.5795(3) 0.6217(2) 0.08613(19) 0.0241(5) Uani 1 1 d .
H11 H 0.6781 0.5917 0.0029 0.029 Uiso 1 1 calc R
C12 C 0.5213(3) 0.5247(2) 0.2293(2) 0.0251(5) Uani 1 1 d .
H12 H 0.5800 0.4286 0.2439 0.030 Uiso 1 1 calc R
C13 C 0.3772(3) 0.56784(19) 0.35148(18) 0.0217(4) Uani 1 1 d .
H13 H 0.3373 0.5023 0.4501 0.026 Uiso 1 1 calc R
C14 C 0.0736(3) 0.7935(2) 0.84591(17) 0.0196(5) 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 0.0000 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'
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
N2 N1 C7 122.31(13)
N2 N1 C8 114.26(14)
C7 N1 C8 123.24(13)
C1 N2 N1 114.01(15)
C1 N3 C2 113.96(13)
N2 C1 C14 112.63(16)
N3 C1 N2 131.29(15)
N3 C1 C14 116.06(14)
N3 C2 C3 119.75(14)
N3 C2 C7 121.03(17)
C3 C2 C7 119.20(15)
C2 C3 H3 119.7
C4 C3 C2 120.59(15)
C4 C3 H3 119.7
C3 C4 H4 120.1
C3 C4 C5 119.83(18)
C5 C4 H4 120.1
C4 C5 H5 119.4
C6 C5 C4 121.14(16)
C6 C5 H5 119.4
C5 C6 H6 120.3
C5 C6 C7 119.36(15)
C7 C6 H6 120.3
N1 C7 C2 116.99(14)
N1 C7 C6 123.13(15)
C6 C7 C2 119.86(17)
C9 C8 N1 119.59(14)
C13 C8 N1 118.77(14)
C13 C8 C9 121.63(15)
C8 C9 H9 120.7
C10 C9 C8 118.61(15)
C10 C9 H9 120.7
C9 C10 H10 119.8
C11 C10 C9 120.44(15)
C11 C10 H10 119.8
C10 C11 H11 119.9
C10 C11 C12 120.23(16)
C12 C11 H11 119.9
C11 C12 H12 119.9
C11 C12 C13 120.17(16)
C13 C12 H12 119.9
C8 C13 C12 118.93(15)
C8 C13 H13 120.5
C12 C13 H13 120.5
F1 C14 C1 110.44(14)
F2 C14 F1 106.44(15)
F2 C14 C1 113.13(14)
F3 C14 F1 106.92(13)
F3 C14 F2 107.95(15)
F3 C14 C1 111.63(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C14 1.3432(18)
F2 C14 1.334(2)
F3 C14 1.3282(19)
N1 N2 1.3695(18)
N1 C7 1.390(2)
N1 C8 1.440(2)
N2 C1 1.327(2)
N3 C1 1.318(2)
N3 C2 1.387(2)
C1 C14 1.523(2)
C2 C3 1.389(3)
C2 C7 1.420(2)
C3 H3 0.9500
C3 C4 1.381(2)
C4 H4 0.9500
C4 C5 1.396(2)
C5 H5 0.9500
C5 C6 1.376(3)
C6 H6 0.9500
C6 C7 1.401(2)
C8 C9 1.390(2)
C8 C13 1.385(2)
C9 H9 0.9500
C9 C10 1.388(2)
C10 H10 0.9500
C10 C11 1.385(2)
C11 H11 0.9500
C11 C12 1.386(2)
C12 H12 0.9500
C12 C13 1.389(2)
C13 H13 0.9500
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
N1 N2 C1 N3 0.1(3)
N1 N2 C1 C14 178.35(13)
N1 C8 C9 C10 180.00(17)
N1 C8 C13 C12 179.83(17)
N2 N1 C7 C2 6.8(2)
N2 N1 C7 C6 -171.86(15)
N2 N1 C8 C9 -125.55(17)
N2 N1 C8 C13 53.7(2)
N2 C1 C14 F1 -80.7(2)
N2 C1 C14 F2 38.50(19)
N2 C1 C14 F3 160.50(15)
N3 C1 C14 F1 97.82(17)
N3 C1 C14 F2 -142.99(15)
N3 C1 C14 F3 -21.0(2)
N3 C2 C3 C4 -177.18(15)
N3 C2 C7 N1 -2.1(2)
N3 C2 C7 C6 176.55(15)
C1 N3 C2 C3 175.69(14)
C1 N3 C2 C7 -2.8(2)
C2 N3 C1 N2 4.1(3)
C2 N3 C1 C14 -174.05(14)
C2 C3 C4 C5 -0.4(2)
C3 C2 C7 N1 179.36(14)
C3 C2 C7 C6 -2.0(2)
C3 C4 C5 C6 -0.1(3)
C4 C5 C6 C7 -0.6(3)
C5 C6 C7 N1 -179.84(15)
C5 C6 C7 C2 1.6(2)
C7 N1 N2 C1 -5.9(2)
C7 N1 C8 C9 59.4(2)
C7 N1 C8 C13 -121.33(18)
C7 C2 C3 C4 1.4(2)
C8 N1 N2 C1 179.03(14)
C8 N1 C7 C2 -178.57(14)
C8 N1 C7 C6 2.8(2)
C8 C9 C10 C11 -0.2(3)
C9 C8 C13 C12 -0.9(3)
C9 C10 C11 C12 -0.2(3)
C10 C11 C12 C13 0.0(3)
C11 C12 C13 C8 0.5(3)
C13 C8 C9 C10 0.7(3)
