#------------------------------------------------------------------------------
#$Date: 2019-11-11 19:42:00 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227118 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/56/4035670.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_4035670
loop_
_publ_author_name
'Azizi, Mahboobeh'
'Nasr-Esfahani, Mahboobeh'
'Mohammadpoor-Baltork, Iraj'
'Moghadam, Majid'
'Mirkhani, Valiollah'
'Tangestaninejad, Shahram'
'Kia, Reza'
_publ_section_title
;
 Synthesis of Quinolines and Pyrido[3,2- g or 2,3- g]quinolines Catalyzed
 by Heterogeneous Propylphosphonium Tetrachloroindate Ionic Liquid.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14743
_journal_page_last               14750
_journal_paper_doi               10.1021/acs.joc.8b02261
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H11 Cl F N O2'
_chemical_formula_sum            'C17 H11 Cl F N O2'
_chemical_formula_weight         315.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.76(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.500(3)
_cell_length_b                   16.914(3)
_cell_length_c                   14.059(3)
_cell_measurement_reflns_used    546
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.45
_cell_volume                     2920.2(11)
_computing_cell_refinement       'X-Area 1.43 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.43 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.43 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL, PLATON (Spek, 2009)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'stoe ipds 2t'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17585
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.288
_diffrn_reflns_theta_min         2.700
_diffrn_source                   sealed-tube
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'mulabs in platon'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   1.000
_exptl_transmission_factor_min   0.998
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0414
_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)+(0.0669P)²+0.1468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2644
_reflns_number_total             3964
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b02261_si_003.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4035670
_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   0.696
_shelx_estimated_absorpt_t_max   0.862
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.85595(12) 0.74764(9) 0.36895(11) 0.0537(3) Uani 1 1 d . .
H1A H 0.9281 0.7592 0.3664 0.064 Uiso 1 1 calc R U
C2 C 0.82711(11) 0.66711(8) 0.37320(9) 0.0459(3) Uani 1 1 d . .
C3 C 0.72000(10) 0.64761(8) 0.37560(9) 0.0428(3) Uani 1 1 d . .
C4 C 0.64466(10) 0.71135(8) 0.37539(8) 0.0441(3) Uani 1 1 d . .
C5 C 0.68336(12) 0.78980(8) 0.37185(9) 0.0484(3) Uani 1 1 d . .
C6 C 0.61071(14) 0.85373(9) 0.37272(11) 0.0598(4) Uani 1 1 d . .
H6A H 0.6359 0.9053 0.3699 0.072 Uiso 1 1 calc R U
C7 C 0.50402(13) 0.84084(10) 0.37761(11) 0.0612(4) Uani 1 1 d . .
H7A H 0.4567 0.8831 0.3785 0.073 Uiso 1 1 calc R U
C8 C 0.46707(12) 0.76277(9) 0.38120(10) 0.0547(3) Uani 1 1 d . .
C9 C 0.53324(11) 0.69916(9) 0.37888(9) 0.0490(3) Uani 1 1 d . .
H9A H 0.5056 0.6482 0.3796 0.059 Uiso 1 1 calc R U
C10 C 0.91488(11) 0.60589(9) 0.37943(10) 0.0512(3) Uani 1 1 d . .
C11 C 1.10356(13) 0.58602(14) 0.39357(18) 0.0890(6) Uani 1 1 d . .
H11A H 1.1695 0.6162 0.4001 0.133 Uiso 1 1 calc R U
H11B H 1.0969 0.5526 0.3376 0.133 Uiso 1 1 calc R U
H11C H 1.1055 0.5540 0.4503 0.133 Uiso 1 1 calc R U
C12 C 0.68186(10) 0.56451(8) 0.38041(9) 0.0432(3) Uani 1 1 d . .
C13 C 0.65545(11) 0.53346(8) 0.46510(11) 0.0511(3) Uani 1 1 d . .
H13A H 0.6590 0.5658 0.5191 0.061 Uiso 1 1 calc R U
C14 C 0.62423(13) 0.45574(10) 0.46971(12) 0.0608(4) Uani 1 1 d . .
H14A H 0.6072 0.4359 0.5268 0.073 Uiso 1 1 calc R U
C15 C 0.61809(13) 0.40717(10) 0.39028(14) 0.0679(4) Uani 1 1 d . .
H15A H 0.5983 0.3544 0.3943 0.081 Uiso 1 1 calc R U
C16 C 0.64122(14) 0.43643(10) 0.30452(13) 0.0673(4) Uani 1 1 d . .
H16A H 0.6364 0.4042 0.2503 0.081 Uiso 1 1 calc R U
C17 C 0.67156(12) 0.51434(9) 0.30163(11) 0.0540(3) Uani 1 1 d . .
N1 N 0.78912(10) 0.80723(7) 0.36831(9) 0.0561(3) Uani 1 1 d . .
O1 O 0.90329(9) 0.53619(8) 0.38394(12) 0.0857(4) Uani 1 1 d . .
O2 O 1.01147(9) 0.63902(7) 0.38266(10) 0.0746(4) Uani 1 1 d . .
F1 F 0.69565(10) 0.54350(7) 0.21790(7) 0.0854(3) Uani 1 1 d . .
Cl1 Cl 0.33111(3) 0.74778(3) 0.38848(4) 0.07734(17) 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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 125.13(14)
N1 C1 H1A 117.4
C2 C1 H1A 117.4
C3 C2 C1 119.07(13)
C3 C2 C10 122.29(12)
C1 C2 C10 118.59(12)
C2 C3 C4 117.33(12)
C2 C3 C12 123.00(12)
C4 C3 C12 119.65(11)
C5 C4 C9 118.79(13)
C5 C4 C3 118.48(12)
C9 C4 C3 122.73(13)
N1 C5 C6 117.61(13)
N1 C5 C4 122.91(13)
C6 C5 C4 119.48(13)
C7 C6 C5 120.88(15)
C7 C6 H6A 119.6
C5 C6 H6A 119.6
C6 C7 C8 118.90(14)
C6 C7 H7A 120.5
C8 C7 H7A 120.5
C9 C8 C7 122.51(15)
C9 C8 Cl1 119.39(13)
C7 C8 Cl1 118.10(12)
C8 C9 C4 119.41(14)
C8 C9 H9A 120.3
C4 C9 H9A 120.3
O1 C10 O2 122.43(14)
O1 C10 C2 126.29(13)
O2 C10 C2 111.25(13)
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C17 C12 C13 116.81(13)
C17 C12 C3 121.71(12)
C13 C12 C3 121.48(12)
C14 C13 C12 120.92(14)
C14 C13 H13A 119.5
C12 C13 H13A 119.5
C13 C14 C15 120.33(15)
C13 C14 H14A 119.8
C15 C14 H14A 119.8
C14 C15 C16 120.30(15)
C14 C15 H15A 119.8
C16 C15 H15A 119.8
C17 C16 C15 118.21(15)
C17 C16 H16A 120.9
C15 C16 H16A 120.9
F1 C17 C16 118.69(14)
F1 C17 C12 117.91(13)
C16 C17 C12 123.37(14)
C1 N1 C5 117.07(12)
C10 O2 C11 116.40(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.308(2)
C1 C2 1.413(2)
C1 H1A 0.9300
C2 C3 1.3855(18)
C2 C10 1.499(2)
C3 C4 1.4312(18)
C3 C12 1.4897(18)
C4 C5 1.416(2)
C4 C9 1.4179(19)
C5 N1 1.3646(19)
C5 C6 1.414(2)
C6 C7 1.366(2)
C6 H6A 0.9300
C7 C8 1.403(2)
C7 H7A 0.9300
C8 C9 1.361(2)
C8 Cl1 1.7402(17)
C9 H9A 0.9300
C10 O1 1.191(2)
C10 O2 1.3242(17)
C11 O2 1.444(2)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C12 C17 1.3821(19)
C12 C13 1.3960(19)
C13 C14 1.376(2)
C13 H13A 0.9300
C14 C15 1.377(2)
C14 H14A 0.9300
C15 C16 1.383(3)
C15 H15A 0.9300
C16 C17 1.374(2)
C16 H16A 0.9300
C17 F1 1.3610(18)
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 C1 C2 C3 1.0(2)
N1 C1 C2 C10 -176.34(13)
C1 C2 C3 C4 -1.12(19)
C10 C2 C3 C4 176.08(12)
C1 C2 C3 C12 -179.80(12)
C10 C2 C3 C12 -2.6(2)
C2 C3 C4 C5 0.58(17)
C12 C3 C4 C5 179.31(11)
C2 C3 C4 C9 -179.22(12)
C12 C3 C4 C9 -0.49(18)
C9 C4 C5 N1 -179.97(12)
C3 C4 C5 N1 0.23(19)
C9 C4 C5 C6 0.55(19)
C3 C4 C5 C6 -179.26(12)
N1 C5 C6 C7 -179.05(13)
C4 C5 C6 C7 0.5(2)
C5 C6 C7 C8 -0.4(2)
C6 C7 C8 C9 -0.8(2)
C6 C7 C8 Cl1 179.44(12)
C7 C8 C9 C4 1.8(2)
Cl1 C8 C9 C4 -178.43(10)
C5 C4 C9 C8 -1.64(19)
C3 C4 C9 C8 178.15(12)
C3 C2 C10 O1 2.4(2)
C1 C2 C10 O1 179.61(16)
C3 C2 C10 O2 -175.50(12)
C1 C2 C10 O2 1.71(19)
C2 C3 C12 C17 -72.56(18)
C4 C3 C12 C17 108.78(15)
C2 C3 C12 C13 107.02(15)
C4 C3 C12 C13 -71.63(16)
C17 C12 C13 C14 2.1(2)
C3 C12 C13 C14 -177.54(13)
C12 C13 C14 C15 -0.3(2)
C13 C14 C15 C16 -1.2(3)
C14 C15 C16 C17 0.8(3)
C15 C16 C17 F1 179.29(14)
C15 C16 C17 C12 1.1(2)
C13 C12 C17 F1 179.28(13)
C3 C12 C17 F1 -1.1(2)
C13 C12 C17 C16 -2.5(2)
C3 C12 C17 C16 177.08(15)
C2 C1 N1 C5 -0.1(2)
C6 C5 N1 C1 179.04(13)
C4 C5 N1 C1 -0.5(2)
O1 C10 O2 C11 -0.9(3)
C2 C10 O2 C11 177.05(15)
