#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/58/7105881.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_7105881
loop_
_publ_author_name
'Jiangtao Zhu'
'Haibo Xie,'
'Zixian Chen'
'Shan Li'
'Yongming Wu'
_publ_section_title
;
 Synthesis of 6-trifluoromethylindolo[1,2-c]quinazolines and related
 heterocycles using N-(2-iodophenyl)trifluoroacetimidoyl chlorides as
 starting material via C–H bond functionalization
;
_journal_name_full               Chem.Commun.
_journal_page_first              1512
_journal_paper_doi               10.1039/c0cc03197f
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C22 H13 F3 N2'
_chemical_formula_weight         362.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.308(2)
_cell_length_b                   7.6365(16)
_cell_length_c                   42.549(9)
_cell_measurement_reflns_used    1968
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.115
_cell_measurement_theta_min      5.503
_cell_volume                     3349.3(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.1001
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            16151
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54073
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0684
_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)+(0.0807P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1698
_reflns_number_gt                1611
_reflns_number_total             3124
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CC03197F.TXT
_cod_data_source_block           cd201336
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        3349.4(12)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7105881
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.48178(18) -0.0660(3) 0.17918(5) 0.0648(6) Uani 1 1 d . . .
F2 F 0.6560(2) 0.0733(4) 0.18641(5) 0.0873(9) Uani 1 1 d . . .
F3 F 0.6581(3) -0.1619(4) 0.16075(6) 0.1053(10) Uani 1 1 d . . .
N1 N 0.6638(2) 0.0614(4) 0.11562(6) 0.0462(8) Uani 1 1 d . . .
N2 N 0.4537(2) 0.1722(3) 0.12923(6) 0.0403(7) Uani 1 1 d . . .
C1 C 0.5722(3) 0.0801(4) 0.13486(7) 0.0405(8) Uani 1 1 d . . .
C2 C 0.5913(3) -0.0180(5) 0.16505(8) 0.0504(9) Uani 1 1 d . . .
C3 C 0.6699(3) 0.1288(5) 0.08495(8) 0.0449(9) Uani 1 1 d . . .
C4 C 0.7943(3) 0.1755(6) 0.07483(9) 0.0611(11) Uani 1 1 d . . .
H4 H 0.8631 0.1692 0.0889 0.073 Uiso 1 1 calc R . .
C5 C 0.8168(4) 0.2297(6) 0.04491(11) 0.0763(13) Uani 1 1 d . . .
H5 H 0.9003 0.2600 0.0387 0.092 Uiso 1 1 calc R . .
C6 C 0.7161(5) 0.2397(6) 0.02403(10) 0.0737(13) Uani 1 1 d . . .
H6 H 0.7303 0.2791 0.0036 0.088 Uiso 1 1 calc R . .
C7 C 0.5930(4) 0.1908(5) 0.03349(8) 0.0616(11) Uani 1 1 d . . .
H7 H 0.5255 0.1956 0.0190 0.074 Uiso 1 1 calc R . .
C8 C 0.5671(3) 0.1349(4) 0.06370(7) 0.0470(9) Uani 1 1 d . . .
C9 C 0.4325(3) 0.0836(4) 0.07273(8) 0.0452(9) Uani 1 1 d . . .
C10 C 0.3435(3) 0.0231(5) 0.05080(8) 0.0563(10) Uani 1 1 d . . .
H10 H 0.3717 -0.0070 0.0308 0.068 Uiso 1 1 calc R . .
C11 C 0.2126(4) 0.0067(5) 0.05834(9) 0.0643(11) Uani 1 1 d . . .
H11 H 0.1554 -0.0360 0.0433 0.077 Uiso 1 1 calc R . .
C12 C 0.1662(3) 0.0514(5) 0.08721(10) 0.0594(10) Uani 1 1 d . . .
H12 H 0.0779 0.0444 0.0915 0.071 Uiso 1 1 calc R . .
C13 C 0.2528(3) 0.1079(5) 0.11015(8) 0.0476(9) Uani 1 1 d . . .
C14 C 0.3845(3) 0.1138(4) 0.10244(7) 0.0398(8) Uani 1 1 d . . .
C15 C 0.3598(3) 0.2126(5) 0.15297(7) 0.0428(9) Uani 1 1 d . . .
C16 C 0.2417(3) 0.1735(5) 0.14127(8) 0.0498(9) Uani 1 1 d . . .
H16 H 0.1639 0.1875 0.1521 0.060 Uiso 1 1 calc R . .
C17 C 0.3942(3) 0.2992(4) 0.18186(7) 0.0430(8) Uani 1 1 d . . .
C18 C 0.3181(3) 0.2797(5) 0.20854(8) 0.0549(10) Uani 1 1 d . . .
H18 H 0.2464 0.2058 0.2079 0.066 Uiso 1 1 calc R . .
C19 C 0.3467(4) 0.3674(6) 0.23566(9) 0.0621(11) Uani 1 1 d . . .
H19 H 0.2941 0.3529 0.2532 0.075 Uiso 1 1 calc R . .
C20 C 0.4520(4) 0.4765(6) 0.23725(9) 0.0667(11) Uani 1 1 d . . .
H20 H 0.4707 0.5364 0.2557 0.080 Uiso 1 1 calc R . .
C21 C 0.5297(3) 0.4964(6) 0.21122(9) 0.0618(11) Uani 1 1 d . . .
H21 H 0.6020 0.5690 0.2123 0.074 Uiso 1 1 calc R . .
C22 C 0.5018(3) 0.4109(5) 0.18395(8) 0.0517(10) Uani 1 1 d . . .
H22 H 0.5549 0.4268 0.1665 0.062 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 126.7(3) . . ?
C14 N2 C1 114.2(2) . . ?
C14 N2 C15 107.1(2) . . ?
C1 N2 C15 124.4(2) . . ?
N1 C1 N2 126.0(3) . . ?
N1 C1 C2 113.7(3) . . ?
N2 C1 C2 120.1(3) . . ?
F3 C2 F2 105.8(3) . . ?
F3 C2 F1 106.1(3) . . ?
F2 C2 F1 105.2(3) . . ?
F3 C2 C1 111.6(3) . . ?
F2 C2 C1 113.0(3) . . ?
F1 C2 C1 114.4(3) . . ?
C8 C3 C4 119.2(3) . . ?
C8 C3 N1 125.5(3) . . ?
C4 C3 N1 114.9(3) . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 119.5(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 122.2(4) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C3 117.9(3) . . ?
C7 C8 C9 120.1(3) . . ?
C3 C8 C9 122.1(3) . . ?
C14 C9 C10 115.8(3) . . ?
C14 C9 C8 121.8(3) . . ?
C10 C9 C8 121.9(3) . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 119.0(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C14 118.0(3) . . ?
C12 C13 C16 135.3(3) . . ?
C14 C13 C16 106.6(3) . . ?
C9 C14 C13 124.0(3) . . ?
C9 C14 N2 127.6(3) . . ?
C13 C14 N2 108.1(3) . . ?
C16 C15 N2 107.6(3) . . ?
C16 C15 C17 129.7(3) . . ?
N2 C15 C17 122.3(3) . . ?
C15 C16 C13 110.4(3) . . ?
C15 C16 H16 124.8 . . ?
C13 C16 H16 124.8 . . ?
C18 C17 C22 117.4(3) . . ?
C18 C17 C15 120.6(3) . . ?
C22 C17 C15 121.9(3) . . ?
C19 C18 C17 121.1(4) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 120.7(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C21 119.3(4) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C22 C21 C20 120.7(4) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C17 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
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
F1 C2 1.330(4) . ?
F2 C2 1.325(4) . ?
F3 C2 1.310(4) . ?
N1 C1 1.258(4) . ?
N1 C3 1.404(4) . ?
N2 C14 1.417(4) . ?
N2 C1 1.430(4) . ?
N2 C15 1.433(4) . ?
C1 C2 1.500(5) . ?
C3 C8 1.394(4) . ?
C3 C4 1.399(4) . ?
C4 C5 1.359(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.492(4) . ?
C9 C14 1.377(4) . ?
C9 C10 1.388(4) . ?
C10 C11 1.393(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(4) . ?
C13 C16 1.420(5) . ?
C15 C16 1.348(4) . ?
C15 C17 1.440(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(4) . ?
C17 C22 1.402(5) . ?
C18 C19 1.366(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.362(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 N2 1.1(5) . . . . ?
C3 N1 C1 C2 176.2(3) . . . . ?
C14 N2 C1 N1 55.1(4) . . . . ?
C15 N2 C1 N1 -170.6(3) . . . . ?
C14 N2 C1 C2 -119.8(3) . . . . ?
C15 N2 C1 C2 14.6(5) . . . . ?
N1 C1 C2 F3 -31.1(4) . . . . ?
N2 C1 C2 F3 144.4(3) . . . . ?
N1 C1 C2 F2 88.0(4) . . . . ?
N2 C1 C2 F2 -96.5(3) . . . . ?
N1 C1 C2 F1 -151.6(3) . . . . ?
N2 C1 C2 F1 23.9(5) . . . . ?
C1 N1 C3 C8 -40.1(5) . . . . ?
C1 N1 C3 C4 146.7(4) . . . . ?
C8 C3 C4 C5 1.2(6) . . . . ?
N1 C3 C4 C5 174.8(4) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C7 -1.4(7) . . . . ?
C5 C6 C7 C8 1.3(6) . . . . ?
C6 C7 C8 C3 0.0(6) . . . . ?
C6 C7 C8 C9 180.0(3) . . . . ?
C4 C3 C8 C7 -1.2(5) . . . . ?
N1 C3 C8 C7 -174.1(3) . . . . ?
C4 C3 C8 C9 178.8(3) . . . . ?
N1 C3 C8 C9 5.9(5) . . . . ?
C7 C8 C9 C14 -145.9(3) . . . . ?
C3 C8 C9 C14 34.1(5) . . . . ?
C7 C8 C9 C10 26.0(5) . . . . ?
C3 C8 C9 C10 -154.1(3) . . . . ?
C14 C9 C10 C11 4.3(5) . . . . ?
C8 C9 C10 C11 -168.0(3) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C10 C11 C12 C13 -2.8(6) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C11 C12 C13 C16 175.5(4) . . . . ?
C10 C9 C14 C13 -8.2(5) . . . . ?
C8 C9 C14 C13 164.1(3) . . . . ?
C10 C9 C14 N2 178.8(3) . . . . ?
C8 C9 C14 N2 -8.9(5) . . . . ?
C12 C13 C14 C9 6.6(5) . . . . ?
C16 C13 C14 C9 -170.7(3) . . . . ?
C12 C13 C14 N2 -179.2(3) . . . . ?
C16 C13 C14 N2 3.5(4) . . . . ?
C1 N2 C14 C9 -47.8(4) . . . . ?
C15 N2 C14 C9 170.3(3) . . . . ?
C1 N2 C14 C13 138.3(3) . . . . ?
C15 N2 C14 C13 -3.6(3) . . . . ?
C14 N2 C15 C16 2.3(4) . . . . ?
C1 N2 C15 C16 -134.7(3) . . . . ?
C14 N2 C15 C17 -171.0(3) . . . . ?
C1 N2 C15 C17 52.0(4) . . . . ?
N2 C15 C16 C13 -0.1(4) . . . . ?
C17 C15 C16 C13 172.5(3) . . . . ?
C12 C13 C16 C15 -178.7(4) . . . . ?
C14 C13 C16 C15 -2.1(4) . . . . ?
C16 C15 C17 C18 32.6(5) . . . . ?
N2 C15 C17 C18 -155.8(3) . . . . ?
C16 C15 C17 C22 -145.0(4) . . . . ?
N2 C15 C17 C22 26.7(5) . . . . ?
C22 C17 C18 C19 0.6(5) . . . . ?
C15 C17 C18 C19 -177.1(3) . . . . ?
C17 C18 C19 C20 -0.4(6) . . . . ?
C18 C19 C20 C21 -0.4(6) . . . . ?
C19 C20 C21 C22 0.9(6) . . . . ?
C20 C21 C22 C17 -0.7(6) . . . . ?
C18 C17 C22 C21 -0.1(5) . . . . ?
C15 C17 C22 C21 177.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653241
