#------------------------------------------------------------------------------
#$Date: 2019-11-23 11:01:00 +0100 (Sat 23 de Nov de 2019) $
#$Revision: 233204 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/56/7235648.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_7235648
loop_
_publ_author_name
'Marquise, Nada'
'Bretel, Guillaume'
'Lassagne, Frédéric'
'Chevallier, Floris'
'Roisnel, Thierry'
'Dorcet, Vincent'
'Halauko, Yury S.'
'Ivashkevich, Oleg A.'
'Matulis, Vadim E.'
'Gros, Philippe C.'
'Mongin, Florence'
_publ_section_title
;
 Deproto-metallation using mixed lithium--zinc and lithium--copper bases
 and computed CH acidity of 2-substituted quinolines
;
_journal_issue                   38
_journal_name_full               'RSC Adv.'
_journal_page_first              19602
_journal_paper_doi               10.1039/C4RA02583K
_journal_volume                  4
_journal_year                    2014
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H10 I N'
_chemical_formula_sum            'C15 H10 I N'
_chemical_formula_weight         331.14
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      60
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-09-25T11:32:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.1278(3)
_cell_length_b                   12.2969(4)
_cell_length_c                   18.3090(6)
_cell_measurement_reflns_used    2908
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.88
_cell_measurement_wavelength     0.71073
_cell_volume                     2505.36(13)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
           WinGX publication routines (Farrugia, 1999),
           CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11818
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.5
_exptl_absorpt_coefficient_mu    2.532
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.1
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2861
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0231P)²+0.3611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0656
_reflns_number_gt                2261
_reflns_number_total             2861
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra02583k2.cif
_cod_data_source_block           GB022
_cod_database_code               7235648
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.65935(19) 0.1366(2) 0.04371(11) 0.0182(5) Uani 1 1 d .
C2 C 0.6049(2) 0.1087(2) -0.02014(14) 0.0184(6) Uani 1 1 d .
C3 C 0.6559(2) 0.0261(2) -0.06509(16) 0.0191(6) Uani 1 1 d .
C4 C 0.5995(2) -0.0088(3) -0.12695(15) 0.0227(7) Uani 1 1 d .
H4 H 0.6336 -0.0659 -0.1551 0.027 Uiso 1 1 calc R
C5 C 0.4906(3) 0.0399(3) -0.14925(15) 0.0256(7) Uani 1 1 d .
H5 H 0.4516 0.0153 -0.1923 0.031 Uiso 1 1 calc R
C6 C 0.4412(2) 0.1217(2) -0.10936(16) 0.0239(7) Uani 1 1 d .
H6 H 0.369 0.1551 -0.1256 0.029 Uiso 1 1 calc R
C7 C 0.4960(2) 0.1577(2) -0.04405(14) 0.0201(6) Uani 1 1 d .
C8 C 0.4462(2) 0.2393(2) 0.00077(16) 0.0226(7) Uani 1 1 d .
H8 H 0.3755 0.2766 -0.014 0.027 Uiso 1 1 calc R
C9 C 0.5002(2) 0.2644(3) 0.06558(16) 0.0231(7) Uani 1 1 d .
H9 H 0.4662 0.3178 0.0969 0.028 Uiso 1 1 calc R
C10 C 0.6073(2) 0.2101(2) 0.08552(15) 0.0202(6) Uani 1 1 d .
C11 C 0.6671(2) 0.2311(3) 0.15731(15) 0.0212(6) Uani 1 1 d .
C12 C 0.6443(3) 0.3242(3) 0.19810(16) 0.0280(7) Uani 1 1 d .
H12 H 0.588 0.3763 0.1807 0.034 Uiso 1 1 calc R
C13 C 0.7031(3) 0.3419(3) 0.26421(18) 0.0346(8) Uani 1 1 d .
H13 H 0.6868 0.4059 0.2915 0.041 Uiso 1 1 calc R
C14 C 0.7846(3) 0.2672(3) 0.29028(16) 0.0341(8) Uani 1 1 d .
H14 H 0.8245 0.2795 0.3354 0.041 Uiso 1 1 calc R
C15 C 0.8080(3) 0.1741(3) 0.25035(17) 0.0324(8) Uani 1 1 d .
H15 H 0.864 0.1222 0.2682 0.039 Uiso 1 1 calc R
C16 C 0.7500(3) 0.1561(3) 0.18426(16) 0.0271(7) Uani 1 1 d .
H16 H 0.767 0.0921 0.1571 0.032 Uiso 1 1 calc R
I1 I 0.818305(16) -0.047008(17) -0.033197(10) 0.02505(9) 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 0 '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'
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
C10 N1 C2 118.4(2)
N1 C2 C7 122.5(3)
N1 C2 C3 119.9(2)
C7 C2 C3 117.6(2)
C4 C3 C2 121.3(3)
C4 C3 I1 119.5(2)
C2 C3 I1 119.1(2)
C3 C4 C5 120.1(3)
C3 C4 H4 119.9
C5 C4 H4 119.9
C6 C5 C4 120.3(3)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C7 120.8(3)
C5 C6 H6 119.6
C7 C6 H6 119.6
C8 C7 C6 123.1(3)
C8 C7 C2 117.2(2)
C6 C7 C2 119.7(3)
C9 C8 C7 119.6(3)
C9 C8 H8 120.2
C7 C8 H8 120.2
C8 C9 C10 119.2(3)
C8 C9 H9 120.4
C10 C9 H9 120.4
N1 C10 C9 123.0(3)
N1 C10 C11 115.7(2)
C9 C10 C11 121.3(3)
C12 C11 C16 118.4(3)
C12 C11 C10 122.2(3)
C16 C11 C10 119.4(3)
C11 C12 C13 120.6(3)
C11 C12 H12 119.7
C13 C12 H12 119.7
C14 C13 C12 120.5(3)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.5(3)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C16 120.3(3)
C14 C15 H15 119.8
C16 C15 H15 119.8
C15 C16 C11 120.7(3)
C15 C16 H16 119.7
C11 C16 H16 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C10 1.318(3)
N1 C2 1.361(3)
C2 C7 1.422(4)
C2 C3 1.425(4)
C3 C4 1.364(4)
C3 I1 2.101(3)
C4 C5 1.412(4)
C4 H4 0.95
C5 C6 1.359(4)
C5 H5 0.95
C6 C7 1.413(4)
C6 H6 0.95
C7 C8 1.410(4)
C8 C9 1.365(4)
C8 H8 0.95
C9 C10 1.415(4)
C9 H9 0.95
C10 C11 1.496(4)
C11 C12 1.390(4)
C11 C16 1.395(4)
C12 C13 1.393(4)
C12 H12 0.95
C13 C14 1.376(5)
C13 H13 0.95
C14 C15 1.383(4)
C14 H14 0.95
C15 C16 1.389(4)
C15 H15 0.95
C16 H16 0.95
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
C10 N1 C2 C7 1.6(4)
C10 N1 C2 C3 -177.2(3)
N1 C2 C3 C4 175.7(3)
C7 C2 C3 C4 -3.2(4)
N1 C2 C3 I1 -2.2(4)
C7 C2 C3 I1 178.9(2)
C2 C3 C4 C5 2.4(4)
I1 C3 C4 C5 -179.7(2)
C3 C4 C5 C6 0.1(4)
C4 C5 C6 C7 -1.6(4)
C5 C6 C7 C8 -177.5(3)
C5 C6 C7 C2 0.7(4)
N1 C2 C7 C8 1.1(4)
C3 C2 C7 C8 180.0(3)
N1 C2 C7 C6 -177.2(3)
C3 C2 C7 C6 1.7(4)
C6 C7 C8 C9 175.5(3)
C2 C7 C8 C9 -2.8(4)
C7 C8 C9 C10 1.8(4)
C2 N1 C10 C9 -2.7(4)
C2 N1 C10 C11 175.8(2)
C8 C9 C10 N1 1.0(4)
C8 C9 C10 C11 -177.4(3)
N1 C10 C11 C12 162.1(3)
C9 C10 C11 C12 -19.4(4)
N1 C10 C11 C16 -17.0(4)
C9 C10 C11 C16 161.6(3)
C16 C11 C12 C13 0.1(4)
C10 C11 C12 C13 -179.0(3)
C11 C12 C13 C14 -0.2(5)
C12 C13 C14 C15 0.0(5)
C13 C14 C15 C16 0.2(5)
C14 C15 C16 C11 -0.3(5)
C12 C11 C16 C15 0.1(4)
C10 C11 C16 C15 179.3(3)
