#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:47:45 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230608 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/65/7156540.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_7156540
loop_
_publ_author_name
'Chandrasekhar, Attoor'
'Ramkumar, Venkatachalam'
'Sankararaman, Sethuraman'
_publ_section_title
;
 Palladium catalyzed carbonylative annulation of the C(sp²)-H
 bond of N,1-diaryl-1H-tetrazol-5-amines and
 N,4-diaryl-4H-triazol-3-amines to quinazolinones.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8629
_journal_page_last               8638
_journal_paper_doi               10.1039/c8ob02516a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C15 H10 F N5 O'
_chemical_formula_sum            'C15 H10 F N5 O'
_chemical_formula_weight         295.28
_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_method           SHELXL-2014/7
_audit_update_record
;
2018-04-03 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                77.8244(14)
_cell_angle_beta                 77.638(2)
_cell_angle_gamma                85.281(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7614(3)
_cell_length_b                   8.5686(4)
_cell_length_c                   11.9894(4)
_cell_measurement_reflns_used    2931
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.71
_cell_volume                     662.75(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9042
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.774
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       REctangular
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0467P)²+0.1295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.1018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1697
_reflns_number_total             2276
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob02516a2.cif
_cod_data_source_block           1075
_cod_depositor_comments
'Adding full bibliography for 7156537--7156540.cif.'
_cod_database_code               7156540
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.989
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
_atom_site_refinement_flags_adp
C1 C 0.2112(2) 0.25318(19) 1.06634(13) 0.0352(4) Uani 1 1 d . .
C2 C 0.1482(3) 0.2945(2) 1.17617(14) 0.0434(4) Uani 1 1 d . .
H2 H 0.1093 0.2164 1.2425 0.052 Uiso 1 1 calc R U
C3 C 0.1451(3) 0.4499(2) 1.18349(14) 0.0430(4) Uani 1 1 d . .
C4 C 0.2015(2) 0.5713(2) 1.08738(14) 0.0402(4) Uani 1 1 d . .
H4 H 0.1978 0.6770 1.0958 0.048 Uiso 1 1 calc R U
C5 C 0.2625(2) 0.53215(19) 0.98018(14) 0.0377(4) Uani 1 1 d . .
H5 H 0.3004 0.6125 0.9151 0.045 Uiso 1 1 calc R U
C6 C 0.2692(2) 0.37328(19) 0.96626(13) 0.0325(4) Uani 1 1 d . .
C7 C 0.3345(2) 0.19536(19) 0.85023(13) 0.0344(4) Uani 1 1 d . .
C8 C 0.2167(2) 0.0865(2) 1.05785(14) 0.0409(4) Uani 1 1 d . .
C9 C 0.4668(3) 0.1934(2) 0.63766(14) 0.0398(4) Uani 1 1 d . .
C10 C 0.6421(3) 0.2764(2) 0.61589(15) 0.0496(5) Uani 1 1 d . .
H10 H 0.7060 0.2812 0.6764 0.060 Uiso 1 1 calc R U
C11 C 0.7211(3) 0.3520(2) 0.50397(17) 0.0593(5) Uani 1 1 d . .
H11 H 0.8383 0.4092 0.4883 0.071 Uiso 1 1 calc R U
C12 C 0.6260(3) 0.3426(2) 0.41546(17) 0.0621(6) Uani 1 1 d . .
H12 H 0.6789 0.3936 0.3396 0.075 Uiso 1 1 calc R U
C13 C 0.4527(3) 0.2581(3) 0.43854(16) 0.0606(6) Uani 1 1 d . .
H13 H 0.3917 0.2518 0.3772 0.073 Uiso 1 1 calc R U
C14 C 0.3654(3) 0.1815(2) 0.55093(15) 0.0467(5) Uani 1 1 d . .
C15 C 0.1741(3) 0.0926(3) 0.5753(2) 0.0715(6) Uani 1 1 d . .
H15A H 0.2061 -0.0201 0.5862 0.107 Uiso 1 1 calc R U
H15B H 0.1068 0.1246 0.5107 0.107 Uiso 1 1 calc R U
H15C H 0.0867 0.1164 0.6445 0.107 Uiso 1 1 calc R U
F1 F 0.08444(17) 0.49172(14) 1.28929(9) 0.0649(4) Uani 1 1 d . .
N1 N 0.3330(2) 0.34384(16) 0.85437(11) 0.0372(3) Uani 1 1 d . .
N2 N 0.3868(2) 0.12122(16) 0.75685(11) 0.0410(4) Uani 1 1 d . .
N3 N 0.3682(2) -0.03936(17) 0.79289(13) 0.0515(4) Uani 1 1 d . .
N4 N 0.3048(2) -0.07290(17) 0.90295(13) 0.0512(4) Uani 1 1 d . .
N5 N 0.2818(2) 0.06988(15) 0.94166(11) 0.0391(3) Uani 1 1 d . .
O1 O 0.1750(2) -0.02976(15) 1.13563(10) 0.0606(4) 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'
O O 0.0106 0.0060 '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
C2 C1 C6 119.98(15)
C2 C1 C8 119.04(14)
C6 C1 C8 120.98(15)
C3 C2 C1 118.69(15)
C3 C2 H2 120.7
C1 C2 H2 120.7
C2 C3 F1 119.36(15)
C2 C3 C4 123.09(16)
F1 C3 C4 117.56(16)
C5 C4 C3 118.58(16)
C5 C4 H4 120.7
C3 C4 H4 120.7
C4 C5 C6 121.33(15)
C4 C5 H5 119.3
C6 C5 H5 119.3
N1 C6 C5 117.66(13)
N1 C6 C1 124.01(15)
C5 C6 C1 118.33(15)
N1 C7 N2 130.07(14)
N1 C7 N5 127.41(14)
N2 C7 N5 102.52(13)
O1 C8 N5 120.94(16)
O1 C8 C1 128.58(16)
N5 C8 C1 110.47(13)
C10 C9 C14 122.88(16)
C10 C9 N2 117.10(15)
C14 C9 N2 119.99(15)
C11 C10 C9 119.40(17)
C11 C10 H10 120.3
C9 C10 H10 120.3
C12 C11 C10 119.60(19)
C12 C11 H11 120.2
C10 C11 H11 120.2
C11 C12 C13 120.22(18)
C11 C12 H12 119.9
C13 C12 H12 119.9
C12 C13 C14 122.20(18)
C12 C13 H13 118.9
C14 C13 H13 118.9
C9 C14 C13 115.69(17)
C9 C14 C15 122.64(17)
C13 C14 C15 121.68(17)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C7 N1 C6 113.21(13)
N3 N2 C7 110.18(13)
N3 N2 C9 122.27(14)
C7 N2 C9 127.37(14)
N4 N3 N2 109.77(14)
N3 N4 N5 106.94(13)
C7 N5 N4 110.59(13)
C7 N5 C8 123.91(14)
N4 N5 C8 125.49(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.404(2)
C1 C6 1.413(2)
C1 C8 1.450(2)
C2 C3 1.351(2)
C2 H2 0.9300
C3 F1 1.3603(19)
C3 C4 1.388(2)
C4 C5 1.366(2)
C4 H4 0.9300
C5 C6 1.402(2)
C5 H5 0.9300
C6 N1 1.3879(19)
C7 N1 1.283(2)
C7 N2 1.369(2)
C7 N5 1.3723(19)
C8 O1 1.2177(19)
C8 N5 1.402(2)
C9 C10 1.381(2)
C9 C14 1.387(2)
C9 N2 1.438(2)
C10 C11 1.374(2)
C10 H10 0.9300
C11 C12 1.372(3)
C11 H11 0.9300
C12 C13 1.375(3)
C12 H12 0.9300
C13 C14 1.395(3)
C13 H13 0.9300
C14 C15 1.498(3)
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
N2 N3 1.3601(19)
N3 N4 1.275(2)
N4 N5 1.3833(19)
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
C6 C1 C2 C3 -0.2(2)
C8 C1 C2 C3 179.46(15)
C1 C2 C3 F1 180.00(14)
C1 C2 C3 C4 0.0(3)
C2 C3 C4 C5 0.2(2)
F1 C3 C4 C5 -179.84(14)
C3 C4 C5 C6 -0.1(2)
C4 C5 C6 N1 180.00(14)
C4 C5 C6 C1 -0.1(2)
C2 C1 C6 N1 -179.84(14)
C8 C1 C6 N1 0.5(2)
C2 C1 C6 C5 0.2(2)
C8 C1 C6 C5 -179.42(14)
C2 C1 C8 O1 -1.0(3)
C6 C1 C8 O1 178.67(17)
C2 C1 C8 N5 179.57(14)
C6 C1 C8 N5 -0.8(2)
C14 C9 C10 C11 0.4(3)
N2 C9 C10 C11 -177.90(16)
C9 C10 C11 C12 -0.6(3)
C10 C11 C12 C13 0.0(3)
C11 C12 C13 C14 1.0(3)
C10 C9 C14 C13 0.5(3)
N2 C9 C14 C13 178.74(15)
C10 C9 C14 C15 -179.35(18)
N2 C9 C14 C15 -1.1(3)
C12 C13 C14 C9 -1.2(3)
C12 C13 C14 C15 178.68(19)
N2 C7 N1 C6 179.75(15)
N5 C7 N1 C6 -0.1(2)
C5 C6 N1 C7 179.91(14)
C1 C6 N1 C7 0.0(2)
N1 C7 N2 N3 179.18(16)
N5 C7 N2 N3 -0.94(17)
N1 C7 N2 C9 4.1(3)
N5 C7 N2 C9 -175.99(14)
C10 C9 N2 N3 -118.19(18)
C14 C9 N2 N3 63.5(2)
C10 C9 N2 C7 56.3(2)
C14 C9 N2 C7 -122.00(18)
C7 N2 N3 N4 0.92(19)
C9 N2 N3 N4 176.27(14)
N2 N3 N4 N5 -0.46(19)
N1 C7 N5 N4 -179.45(15)
N2 C7 N5 N4 0.66(16)
N1 C7 N5 C8 -0.3(3)
N2 C7 N5 C8 179.83(14)
N3 N4 N5 C7 -0.15(18)
N3 N4 N5 C8 -179.30(15)
O1 C8 N5 C7 -178.81(15)
C1 C8 N5 C7 0.7(2)
O1 C8 N5 N4 0.2(3)
C1 C8 N5 N4 179.74(14)
