#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/05/7150555.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_7150555
loop_
_publ_author_name
'Likhar, Pravin R.'
'Subhas, Madavu Salian'
'Roy, Sarabindu'
'Kantam, Mannepalli Lakshmi'
'Sridhar, Balasubramanian'
'Seth, Ratanesh Kumar'
'Biswas, Sukla'
_publ_section_title
;
 Synthesis of highly substituted 2-perfluoroalkyl quinolines by
 electrophilic iodocyclization of perfluoroalkyl propargyl
 imines/amines
;
_journal_issue                   1
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              85
_journal_page_last               93
_journal_paper_doi               10.1039/b815398a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C18 H13 F3 I N O2'
_chemical_formula_sum            'C18 H13 F3 I N O2'
_chemical_formula_weight         459.19
_chemical_name_systematic
3-Iodo-6-methoxy-4-(p-methoxyphenyl)-2-trifluoromethyl)quinoline
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                107.100(4)
_cell_angle_beta                 95.726(4)
_cell_angle_gamma                110.042(3)
_cell_formula_units_Z            2
_cell_length_a                   8.995(2)
_cell_length_b                   10.147(2)
_cell_length_c                   11.016(3)
_cell_measurement_reflns_used    6302
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.28
_cell_volume                     880.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7577
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.860
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²+0.2514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0672
_reflns_number_gt                2691
_reflns_number_total             2973
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b815398a.txt
_cod_data_source_block           aq35m
_cod_database_code               7150555
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5892(3) 0.3631(3) 1.0641(2) 0.0440(5) Uani 1 1 d . . .
C2 C 0.7151(3) 0.2766(3) 0.9040(2) 0.0437(5) Uani 1 1 d . . .
C3 C 0.8593(3) 0.2933(3) 0.8563(3) 0.0560(7) Uani 1 1 d . . .
H3 H 0.9532 0.3788 0.8987 0.067 Uiso 1 1 calc R . .
C4 C 0.8608(3) 0.1844(3) 0.7485(3) 0.0618(7) Uani 1 1 d . . .
H4 H 0.9556 0.1965 0.7180 0.074 Uiso 1 1 calc R . .
C5 C 0.7180(3) 0.0528(3) 0.6827(2) 0.0522(6) Uani 1 1 d . . .
C6 C 0.5759(3) 0.0346(3) 0.7242(2) 0.0452(5) Uani 1 1 d . . .
H6 H 0.4827 -0.0507 0.6792 0.054 Uiso 1 1 calc R . .
C7 C 0.5710(3) 0.1458(3) 0.8358(2) 0.0403(5) Uani 1 1 d . . .
C8 C 0.4274(3) 0.1307(3) 0.8866(2) 0.0407(5) Uani 1 1 d . . .
C9 C 0.4370(3) 0.2378(3) 1.0017(2) 0.0428(5) Uani 1 1 d . . .
C10 C 0.2746(3) -0.0043(3) 0.8115(2) 0.0400(5) Uani 1 1 d . . .
C11 C 0.1843(3) -0.0089(3) 0.6991(3) 0.0559(7) Uani 1 1 d . . .
H11 H 0.2129 0.0753 0.6748 0.067 Uiso 1 1 calc R . .
C12 C 0.0516(3) -0.1387(4) 0.6226(3) 0.0635(8) Uani 1 1 d . . .
H12 H -0.0075 -0.1406 0.5474 0.076 Uiso 1 1 calc R . .
C13 C 0.0070(3) -0.2645(3) 0.6575(3) 0.0527(6) Uani 1 1 d . . .
C14 C 0.0943(3) -0.2613(3) 0.7698(3) 0.0534(6) Uani 1 1 d . . .
H14 H 0.0650 -0.3453 0.7943 0.064 Uiso 1 1 calc R . .
C15 C 0.2268(3) -0.1307(3) 0.8457(3) 0.0514(6) Uani 1 1 d . . .
H15 H 0.2847 -0.1285 0.9216 0.062 Uiso 1 1 calc R . .
C16 C 0.6125(3) 0.4838(3) 1.1941(3) 0.0543(6) Uani 1 1 d . . .
C17 C 0.6067(4) -0.1921(4) 0.5201(3) 0.0719(9) Uani 1 1 d . . .
H17A H 0.5768 -0.2350 0.5854 0.108 Uiso 1 1 calc R . .
H17B H 0.6395 -0.2572 0.4561 0.108 Uiso 1 1 calc R . .
H17C H 0.5155 -0.1801 0.4789 0.108 Uiso 1 1 calc R . .
C18 C -0.1678(5) -0.5228(4) 0.5992(4) 0.0886(11) Uani 1 1 d . . .
H18A H -0.0759 -0.5503 0.6040 0.133 Uiso 1 1 calc R . .
H18B H -0.2554 -0.6004 0.5303 0.133 Uiso 1 1 calc R . .
H18C H -0.2014 -0.5096 0.6804 0.133 Uiso 1 1 calc R . .
F1 F 0.7631(2) 0.5885(2) 1.23531(19) 0.0917(7) Uani 1 1 d . . .
F2 F 0.5118(3) 0.5548(2) 1.19110(18) 0.0785(5) Uani 1 1 d . . .
F3 F 0.5858(2) 0.4266(2) 1.28936(15) 0.0752(5) Uani 1 1 d . . .
I1 I 0.22639(2) 0.21310(2) 1.078796(18) 0.06585(10) Uani 1 1 d . . .
N1 N 0.7207(2) 0.3829(2) 1.01714(19) 0.0455(5) Uani 1 1 d . . .
O1 O 0.7384(2) -0.0491(2) 0.5798(2) 0.0696(6) Uani 1 1 d . . .
O2 O -0.1244(3) -0.3872(3) 0.5740(2) 0.0764(6) 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'
I I -0.4742 1.8119 '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
N1 C1 C9 123.8(2) . . ?
N1 C1 C16 113.9(2) . . ?
C9 C1 C16 122.2(2) . . ?
N1 C2 C3 118.9(2) . . ?
N1 C2 C7 122.1(2) . . ?
C3 C2 C7 118.9(2) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O1 C5 C6 125.1(2) . . ?
O1 C5 C4 114.2(2) . . ?
C6 C5 C4 120.7(2) . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 119.5(2) . . ?
C6 C7 C8 122.6(2) . . ?
C2 C7 C8 117.8(2) . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 C10 123.6(2) . . ?
C7 C8 C10 117.6(2) . . ?
C8 C9 C1 118.6(2) . . ?
C8 C9 I1 118.85(16) . . ?
C1 C9 I1 122.52(17) . . ?
C15 C10 C11 118.1(2) . . ?
C15 C10 C8 121.5(2) . . ?
C11 C10 C8 120.2(2) . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O2 C13 C12 115.8(2) . . ?
O2 C13 C14 124.5(3) . . ?
C12 C13 C14 119.7(2) . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C10 C15 C14 122.0(2) . . ?
C10 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
F1 C16 F2 107.0(2) . . ?
F1 C16 F3 105.9(2) . . ?
F2 C16 F3 105.7(2) . . ?
F1 C16 C1 112.5(2) . . ?
F2 C16 C1 113.4(2) . . ?
F3 C16 C1 111.8(2) . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C2 118.6(2) . . ?
C5 O1 C17 117.2(2) . . ?
C13 O2 C18 118.2(3) . . ?
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
C1 N1 1.314(3) . ?
C1 C9 1.439(3) . ?
C1 C16 1.526(3) . ?
C2 N1 1.370(3) . ?
C2 C3 1.423(4) . ?
C2 C7 1.430(3) . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.424(4) . ?
C4 H4 0.9300 . ?
C5 O1 1.368(3) . ?
C5 C6 1.372(4) . ?
C6 C7 1.419(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.437(3) . ?
C8 C9 1.378(3) . ?
C8 C10 1.505(3) . ?
C9 I1 2.119(2) . ?
C10 C15 1.382(4) . ?
C10 C11 1.392(4) . ?
C11 C12 1.392(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9300 . ?
C13 O2 1.376(3) . ?
C13 C14 1.383(4) . ?
C14 C15 1.394(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 F1 1.333(3) . ?
C16 F2 1.340(3) . ?
C16 F3 1.345(3) . ?
C17 O1 1.431(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O2 1.414(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
N1 C2 C3 C4 175.7(3) . . . . ?
C7 C2 C3 C4 -1.3(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 O1 -177.5(3) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
O1 C5 C6 C7 177.5(3) . . . . ?
C4 C5 C6 C7 -1.6(4) . . . . ?
C5 C6 C7 C2 0.1(4) . . . . ?
C5 C6 C7 C8 -177.8(2) . . . . ?
N1 C2 C7 C6 -175.6(2) . . . . ?
C3 C2 C7 C6 1.3(4) . . . . ?
N1 C2 C7 C8 2.4(4) . . . . ?
C3 C2 C7 C8 179.3(2) . . . . ?
C6 C7 C8 C9 174.4(2) . . . . ?
C2 C7 C8 C9 -3.5(3) . . . . ?
C6 C7 C8 C10 -4.3(3) . . . . ?
C2 C7 C8 C10 177.7(2) . . . . ?
C7 C8 C9 C1 2.1(3) . . . . ?
C10 C8 C9 C1 -179.2(2) . . . . ?
C7 C8 C9 I1 -178.73(17) . . . . ?
C10 C8 C9 I1 0.0(3) . . . . ?
N1 C1 C9 C8 0.7(4) . . . . ?
C16 C1 C9 C8 -177.7(2) . . . . ?
N1 C1 C9 I1 -178.52(19) . . . . ?
C16 C1 C9 I1 3.1(3) . . . . ?
C9 C8 C10 C15 -81.3(3) . . . . ?
C7 C8 C10 C15 97.4(3) . . . . ?
C9 C8 C10 C11 103.7(3) . . . . ?
C7 C8 C10 C11 -77.6(3) . . . . ?
C15 C10 C11 C12 -1.2(4) . . . . ?
C8 C10 C11 C12 174.0(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 O2 -179.1(3) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
O2 C13 C14 C15 179.1(3) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
C11 C10 C15 C14 1.3(4) . . . . ?
C8 C10 C15 C14 -173.8(2) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
N1 C1 C16 F1 0.6(3) . . . . ?
C9 C1 C16 F1 179.1(3) . . . . ?
N1 C1 C16 F2 122.2(3) . . . . ?
C9 C1 C16 F2 -59.3(3) . . . . ?
N1 C1 C16 F3 -118.4(3) . . . . ?
C9 C1 C16 F3 60.2(3) . . . . ?
C9 C1 N1 C2 -1.8(4) . . . . ?
C16 C1 N1 C2 176.7(2) . . . . ?
C3 C2 N1 C1 -176.7(2) . . . . ?
C7 C2 N1 C1 0.2(4) . . . . ?
C6 C5 O1 C17 -7.3(4) . . . . ?
C4 C5 O1 C17 171.8(3) . . . . ?
C12 C13 O2 C18 175.1(3) . . . . ?
C14 C13 O2 C18 -4.3(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653361
