#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:01:00 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233204 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/56/7235653.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_7235653
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         'C22 H13 N O'
_chemical_formula_sum            'C22 H13 N O'
_chemical_formula_weight         307.33
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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      2.3
_audit_creation_date             2013-12-03T17:57:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 110.6260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9851(4)
_cell_length_b                   8.0059(3)
_cell_length_c                   16.6683(8)
_cell_measurement_reflns_used    2615
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.61
_cell_measurement_wavelength     0.71073
_cell_volume                     1496.83(10)
_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, 2012),
           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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0434
_diffrn_reflns_av_unetI/netI     0.044
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11243
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0596P)²+0.1069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.107
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                2679
_reflns_number_total             3420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra02583k2.cif
_cod_data_source_block           NM273
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7235653
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_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
O1 O 0.38681(8) 0.46395(12) 0.78584(6) 0.0277(2) Uani 1 1 d .
C2 C 0.34810(11) 0.43913(15) 0.84309(8) 0.0217(3) Uani 1 1 d .
C3 C 0.23001(11) 0.49749(16) 0.84441(8) 0.0221(3) Uani 1 1 d .
C4 C 0.14227(12) 0.58783(16) 0.78375(9) 0.0253(3) Uani 1 1 d .
H4 H 0.151 0.6197 0.7314 0.03 Uiso 1 1 calc R
C5 C 0.04057(12) 0.63110(18) 0.80125(9) 0.0296(3) Uani 1 1 d .
H5 H -0.0213 0.6931 0.7605 0.035 Uiso 1 1 calc R
C6 C 0.02944(13) 0.58385(19) 0.87818(10) 0.0330(4) Uani 1 1 d .
H6 H -0.0406 0.6137 0.8892 0.04 Uiso 1 1 calc R
C7 C 0.11838(12) 0.49374(17) 0.93962(9) 0.0293(3) Uani 1 1 d .
H7 H 0.1101 0.4628 0.9923 0.035 Uiso 1 1 calc R
C8 C 0.21900(12) 0.45041(16) 0.92207(8) 0.0236(3) Uani 1 1 d .
C9 C 0.32859(11) 0.35907(16) 0.97314(8) 0.0229(3) Uani 1 1 d .
C10 C 0.35967(12) 0.29202(17) 1.05594(8) 0.0266(3) Uani 1 1 d .
H10 H 0.3071 0.3015 1.0871 0.032 Uiso 1 1 calc R
C11 C 0.46716(12) 0.21269(17) 1.09093(8) 0.0273(3) Uani 1 1 d .
H11 H 0.4888 0.1667 1.1469 0.033 Uiso 1 1 calc R
C12 C 0.54676(12) 0.19771(16) 1.04551(8) 0.0237(3) Uani 1 1 d .
C13 C 0.51610(11) 0.26614(15) 0.96152(8) 0.0215(3) Uani 1 1 d .
C14 C 0.40447(11) 0.34849(15) 0.92668(8) 0.0212(3) Uani 1 1 d .
C15 C 0.65897(12) 0.11829(16) 1.08055(8) 0.0268(3) Uani 1 1 d .
H15 H 0.684 0.0733 1.1369 0.032 Uiso 1 1 calc R
C16 C 0.73052(12) 0.10666(17) 1.03359(9) 0.0276(3) Uani 1 1 d .
H16 H 0.8055 0.0522 1.0565 0.033 Uiso 1 1 calc R
C17 C 0.69307(11) 0.17632(15) 0.94971(8) 0.0233(3) Uani 1 1 d .
N18 N 0.58942(9) 0.25425(13) 0.91462(7) 0.0229(3) Uani 1 1 d .
C19 C 0.77041(11) 0.16785(16) 0.89716(8) 0.0243(3) Uani 1 1 d .
C20 C 0.85737(12) 0.04374(17) 0.91033(9) 0.0296(3) Uani 1 1 d .
H20 H 0.8687 -0.0363 0.9546 0.036 Uiso 1 1 calc R
C21 C 0.92693(12) 0.03671(19) 0.85950(10) 0.0337(4) Uani 1 1 d .
H21 H 0.9849 -0.0491 0.8687 0.04 Uiso 1 1 calc R
C22 C 0.91303(12) 0.1534(2) 0.79537(10) 0.0343(4) Uani 1 1 d .
H22 H 0.9612 0.1482 0.7608 0.041 Uiso 1 1 calc R
C23 C 0.82777(12) 0.27818(19) 0.78224(9) 0.0326(3) Uani 1 1 d .
H23 H 0.8181 0.3594 0.7387 0.039 Uiso 1 1 calc R
C24 C 0.75692(12) 0.28479(17) 0.83227(9) 0.0270(3) Uani 1 1 d .
H24 H 0.6984 0.37 0.8223 0.032 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 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'
O O 0.0106 0.006 '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
O1 C2 C3 125.77(12)
O1 C2 C14 129.44(12)
C3 C2 C14 104.79(11)
C4 C3 C8 121.59(12)
C4 C3 C2 129.27(12)
C8 C3 C2 109.11(11)
C3 C4 C5 118.30(13)
C3 C4 H4 120.9
C5 C4 H4 120.9
C6 C5 C4 120.11(13)
C6 C5 H5 119.9
C4 C5 H5 119.9
C5 C6 C7 121.55(13)
C5 C6 H6 119.2
C7 C6 H6 119.2
C8 C7 C6 118.28(13)
C8 C7 H7 120.9
C6 C7 H7 120.9
C7 C8 C3 120.16(12)
C7 C8 C9 131.71(12)
C3 C8 C9 108.12(11)
C14 C9 C10 121.72(12)
C14 C9 C8 109.37(11)
C10 C9 C8 128.91(12)
C11 C10 C9 118.71(12)
C11 C10 H10 120.6
C9 C10 H10 120.6
C10 C11 C12 121.43(12)
C10 C11 H11 119.3
C12 C11 H11 119.3
C15 C12 C11 122.60(12)
C15 C12 C13 117.19(12)
C11 C12 C13 120.20(12)
N18 C13 C14 120.04(11)
N18 C13 C12 122.57(12)
C14 C13 C12 117.39(12)
C9 C14 C13 120.54(12)
C9 C14 C2 108.57(11)
C13 C14 C2 130.87(12)
C16 C15 C12 119.76(12)
C16 C15 H15 120.1
C12 C15 H15 120.1
C15 C16 C17 119.79(13)
C15 C16 H16 120.1
C17 C16 H16 120.1
N18 C17 C16 122.63(12)
N18 C17 C19 116.33(11)
C16 C17 C19 121.03(12)
C17 N18 C13 118.04(11)
C24 C19 C20 118.30(13)
C24 C19 C17 120.04(12)
C20 C19 C17 121.67(12)
C21 C20 C19 120.58(14)
C21 C20 H20 119.7
C19 C20 H20 119.7
C20 C21 C22 120.71(14)
C20 C21 H21 119.6
C22 C21 H21 119.6
C21 C22 C23 119.23(13)
C21 C22 H22 120.4
C23 C22 H22 120.4
C24 C23 C22 120.34(14)
C24 C23 H23 119.8
C22 C23 H23 119.8
C23 C24 C19 120.84(13)
C23 C24 H24 119.6
C19 C24 H24 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.2154(15)
C2 C3 1.4980(18)
C2 C14 1.5037(17)
C3 C4 1.3792(18)
C3 C8 1.3983(18)
C4 C5 1.3934(18)
C4 H4 0.95
C5 C6 1.388(2)
C5 H5 0.95
C6 C7 1.392(2)
C6 H6 0.95
C7 C8 1.3815(18)
C7 H7 0.95
C8 C9 1.4821(18)
C9 C14 1.3893(17)
C9 C10 1.4034(18)
C10 C11 1.3688(19)
C10 H10 0.95
C11 C12 1.4166(18)
C11 H11 0.95
C12 C15 1.4144(18)
C12 C13 1.4257(18)
C13 N18 1.3697(16)
C13 C14 1.4194(18)
C15 C16 1.3526(19)
C15 H15 0.95
C16 C17 1.4231(18)
C16 H16 0.95
C17 N18 1.3277(16)
C17 C19 1.4842(18)
C19 C24 1.3961(19)
C19 C20 1.4002(18)
C20 C21 1.383(2)
C20 H20 0.95
C21 C22 1.385(2)
C21 H21 0.95
C22 C23 1.390(2)
C22 H22 0.95
C23 C24 1.3850(19)
C23 H23 0.95
C24 H24 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
O1 C2 C3 C4 0.3(2)
C14 C2 C3 C4 179.62(13)
O1 C2 C3 C8 -177.80(12)
C14 C2 C3 C8 1.56(13)
C8 C3 C4 C5 -0.40(19)
C2 C3 C4 C5 -178.26(12)
C3 C4 C5 C6 0.2(2)
C4 C5 C6 C7 0.3(2)
C5 C6 C7 C8 -0.5(2)
C6 C7 C8 C3 0.3(2)
C6 C7 C8 C9 178.90(14)
C4 C3 C8 C7 0.19(19)
C2 C3 C8 C7 178.43(12)
C4 C3 C8 C9 -178.73(12)
C2 C3 C8 C9 -0.49(14)
C7 C8 C9 C14 -179.63(14)
C3 C8 C9 C14 -0.89(15)
C7 C8 C9 C10 -0.7(2)
C3 C8 C9 C10 178.09(13)
C14 C9 C10 C11 -0.8(2)
C8 C9 C10 C11 -179.61(13)
C9 C10 C11 C12 0.2(2)
C10 C11 C12 C15 179.17(12)
C10 C11 C12 C13 0.1(2)
C15 C12 C13 N18 1.32(18)
C11 C12 C13 N18 -179.58(12)
C15 C12 C13 C14 -178.94(11)
C11 C12 C13 C14 0.16(18)
C10 C9 C14 C13 1.06(19)
C8 C9 C14 C13 -179.88(11)
C10 C9 C14 C2 -177.18(12)
C8 C9 C14 C2 1.87(14)
N18 C13 C14 C9 179.01(11)
C12 C13 C14 C9 -0.74(18)
N18 C13 C14 C2 -3.2(2)
C12 C13 C14 C2 177.06(12)
O1 C2 C14 C9 177.22(13)
C3 C2 C14 C9 -2.10(13)
O1 C2 C14 C13 -0.8(2)
C3 C2 C14 C13 179.90(12)
C11 C12 C15 C16 179.39(12)
C13 C12 C15 C16 -1.53(19)
C12 C15 C16 C17 0.8(2)
C15 C16 C17 N18 0.2(2)
C15 C16 C17 C19 179.04(12)
C16 C17 N18 C13 -0.48(18)
C19 C17 N18 C13 -179.34(10)
C14 C13 N18 C17 179.94(11)
C12 C13 N18 C17 -0.33(18)
N18 C17 C19 C24 23.16(17)
C16 C17 C19 C24 -155.72(12)
N18 C17 C19 C20 -156.41(12)
C16 C17 C19 C20 24.71(19)
C24 C19 C20 C21 -0.7(2)
C17 C19 C20 C21 178.85(12)
C19 C20 C21 C22 0.8(2)
C20 C21 C22 C23 -0.2(2)
C21 C22 C23 C24 -0.5(2)
C22 C23 C24 C19 0.6(2)
C20 C19 C24 C23 0.0(2)
C17 C19 C24 C23 -179.59(12)
