#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/17/2201735.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2201735
loop_
_publ_author_name
'Qi, Jian Ying'
'Qiu, Li Qin'
'Yang, Qi Yun'
'Zhou, Zhong Yuan'
'Chan, Albert S. C.'
_publ_section_title
;
 N-(4-Iodophenyl)quinoline-2-carboxamide
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o104
_journal_page_last               o105
_journal_paper_doi               10.1107/S1600536802022419
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C16 H11 I N2 O'
_chemical_formula_moiety         'C16 H11 I N2 O'
_chemical_formula_sum            'C16 H11 I N2 O'
_chemical_formula_weight         374.17
_chemical_name_systematic
;
N-(4-iodopheny)quinoline-2-carboxamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90.00
_cell_angle_beta                 102.377(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5389(10)
_cell_length_b                   17.036(3)
_cell_length_c                   12.702(2)
_cell_measurement_reflns_used    4725
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1382.1(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SHELXTL-NT (Siemens, 1995)'
_computing_molecular_graphics    SHELXTL-NT
_computing_publication_material  SHELXTL-NT
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9337
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.313
_exptl_absorpt_correction_T_max  0.7377
_exptl_absorpt_correction_T_min  0.6548
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.334
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.05P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0716
_reflns_number_gt                2153
_reflns_number_total             3169
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ac6024.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2201735
_cod_database_fobs_code          2201735
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1 0.73626(3) 0.085146(15) 0.107807(18) 0.06689(11) Uani d . 1 . . I
O1 1.3784(3) -0.09556(13) 0.57661(18) 0.0635(6) Uani d . 1 . . O
N1 1.8030(3) -0.18297(13) 0.49117(17) 0.0428(5) Uani d . 1 . . N
N2 1.4644(4) -0.09772(13) 0.4118(2) 0.0496(6) Uani d . 1 . . N
H2A 1.5606 -0.1137 0.3802 0.060 Uiso calc R 1 . . H
C1 2.1005(4) -0.25189(18) 0.4569(2) 0.0508(7) Uani d . 1 . . C
H1B 2.0672 -0.2350 0.3856 0.061 Uiso calc R 1 . . H
C2 2.2703(5) -0.29842(19) 0.4910(3) 0.0592(8) Uani d . 1 . . C
H2B 2.3519 -0.3131 0.4426 0.071 Uiso calc R 1 . . H
C3 2.3244(5) -0.3245(2) 0.5969(3) 0.0652(9) Uani d . 1 . . C
H3A 2.4408 -0.3567 0.6185 0.078 Uiso calc R 1 . . H
C4 2.2069(5) -0.3031(2) 0.6701(3) 0.0601(9) Uani d . 1 . . C
H4A 2.2448 -0.3202 0.7411 0.072 Uiso calc R 1 . . H
C5 2.0284(4) -0.25515(16) 0.6368(2) 0.0464(7) Uani d . 1 . . C
C6 1.8986(5) -0.23214(19) 0.7061(2) 0.0553(8) Uani d . 1 . . C
H6A 1.9291 -0.2483 0.7777 0.066 Uiso calc R 1 . . H
C7 1.7287(5) -0.18645(19) 0.6688(2) 0.0548(8) Uani d . 1 . . C
H7A 1.6419 -0.1709 0.7141 0.066 Uiso calc R 1 . . H
C8 1.6867(4) -0.16315(16) 0.5600(2) 0.0431(7) Uani d . 1 . . C
C9 1.9747(4) -0.22898(15) 0.5286(2) 0.0416(7) Uani d . 1 . . C
C10 1.4944(4) -0.11484(17) 0.5182(2) 0.0460(7) Uani d . 1 . . C
C11 1.2966(4) -0.05721(17) 0.3460(2) 0.0444(7) Uani d . 1 . . C
C12 1.1149(4) -0.03794(19) 0.3795(2) 0.0520(8) Uani d . 1 . . C
H12A 1.0991 -0.0521 0.4480 0.062 Uiso calc R 1 . . H
C13 0.9566(4) 0.00244(18) 0.3107(3) 0.0522(8) Uani d . 1 . . C
H13A 0.8348 0.0155 0.3334 0.063 Uiso calc R 1 . . H
C14 0.9787(4) 0.02331(17) 0.2092(2) 0.0477(7) Uani d . 1 . . C
C15 1.1588(4) 0.00457(18) 0.1749(2) 0.0525(8) Uani d . 1 . . C
H15A 1.1734 0.0185 0.1061 0.063 Uiso calc R 1 . . H
C16 1.3173(4) -0.03514(18) 0.2436(3) 0.0522(8) Uani d . 1 . . C
H16A 1.4397 -0.0473 0.2210 0.063 Uiso calc R 1 . . H
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'
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
C8 N1 C9 117.6(2)
C10 N2 C11 128.7(2)
C10 N2 H2A 115.7
C11 N2 H2A 115.7
C2 C1 C9 120.4(3)
C2 C1 H1B 119.8
C9 C1 H1B 119.8
C1 C2 C3 121.2(3)
C1 C2 H2B 119.4
C3 C2 H2B 119.4
C4 C3 C2 120.4(3)
C4 C3 H3A 119.8
C2 C3 H3A 119.8
C3 C4 C5 119.7(3)
C3 C4 H4A 120.1
C5 C4 H4A 120.1
C6 C5 C4 123.1(3)
C6 C5 C9 117.6(3)
C4 C5 C9 119.3(3)
C7 C6 C5 120.1(3)
C7 C6 H6A 119.9
C5 C6 H6A 119.9
C6 C7 C8 118.5(3)
C6 C7 H7A 120.7
C8 C7 H7A 120.7
N1 C8 C7 124.0(3)
N1 C8 C10 117.6(3)
C7 C8 C10 118.3(3)
N1 C9 C1 119.0(2)
N1 C9 C5 122.1(2)
C1 C9 C5 118.9(3)
O1 C10 N2 125.1(3)
O1 C10 C8 121.1(3)
N2 C10 C8 113.7(3)
C12 C11 C16 119.1(3)
C12 C11 N2 123.0(3)
C16 C11 N2 117.9(3)
C11 C12 C13 119.9(3)
C11 C12 H12A 120.1
C13 C12 H12A 120.1
C14 C13 C12 120.3(3)
C14 C13 H13A 119.8
C12 C13 H13A 119.8
C13 C14 C15 120.4(3)
C13 C14 I1 119.2(2)
C15 C14 I1 120.4(2)
C14 C15 C16 119.3(3)
C14 C15 H15A 120.3
C16 C15 H15A 120.3
C15 C16 C11 121.0(3)
C15 C16 H16A 119.5
C11 C16 H16A 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C14 . 2.099(3) ?
O1 C10 . 1.215(3) ?
N1 C8 . 1.320(3) ?
N1 C9 . 1.368(3) ?
N2 C10 . 1.355(4) ?
N2 C11 . 1.409(4) ?
N2 H2A . 0.8600 ?
C1 C2 . 1.357(4) ?
C1 C9 . 1.407(4) ?
C1 H1B . 0.9300 ?
C2 C3 . 1.388(5) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.376(5) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.413(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.403(4) ?
C5 C9 . 1.416(4) ?
C6 C7 . 1.356(4) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.407(4) ?
C7 H7A . 0.9300 ?
C8 C10 . 1.502(4) ?
C11 C12 . 1.384(4) ?
C11 C16 . 1.388(4) ?
C12 C13 . 1.385(4) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.375(4) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.378(4) ?
C15 C16 . 1.381(4) ?
C15 H15A . 0.9300 ?
C16 H16A . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A N1 0.86 2.22 2.659(3) 112
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
C9 C1 C2 C3 0.0(5)
C1 C2 C3 C4 -0.5(5)
C2 C3 C4 C5 0.9(5)
C3 C4 C5 C6 178.7(3)
C3 C4 C5 C9 -0.8(4)
C4 C5 C6 C7 -179.5(3)
C9 C5 C6 C7 0.0(4)
C5 C6 C7 C8 0.1(5)
C9 N1 C8 C7 0.0(4)
C9 N1 C8 C10 -178.1(2)
C6 C7 C8 N1 -0.1(5)
C6 C7 C8 C10 178.0(3)
C8 N1 C9 C1 179.3(2)
C8 N1 C9 C5 0.1(4)
C2 C1 C9 N1 -179.1(3)
C2 C1 C9 C5 0.1(4)
C6 C5 C9 N1 -0.1(4)
C4 C5 C9 N1 179.4(3)
C6 C5 C9 C1 -179.2(3)
C4 C5 C9 C1 0.3(4)
C11 N2 C10 O1 -1.8(5)
C11 N2 C10 C8 176.7(3)
N1 C8 C10 O1 178.8(3)
C7 C8 C10 O1 0.7(4)
N1 C8 C10 N2 0.3(4)
C7 C8 C10 N2 -177.9(3)
C10 N2 C11 C12 -10.0(5)
C10 N2 C11 C16 169.2(3)
C16 C11 C12 C13 0.4(5)
N2 C11 C12 C13 179.6(3)
C11 C12 C13 C14 0.2(5)
C12 C13 C14 C15 -0.2(5)
C12 C13 C14 I1 -179.6(2)
C13 C14 C15 C16 -0.3(5)
I1 C14 C15 C16 179.1(2)
C14 C15 C16 C11 0.8(5)
C12 C11 C16 C15 -0.9(5)
N2 C11 C16 C15 179.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1898930
