#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117702.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_7117702
loop_
_publ_author_name
'Gopal Chandru Senadi'
'Wan-Ping Hu'
'Amol Milind Garkhedkar'
'Siva Senthil Kumar Boominathan'
'Jeh-Jeng Wang'
_publ_section_title
;
 Palladium(II)-catalysed regioselective synthesis of 3,4-disubstituted
 quinolines and 2,3,5-trisubstituted pyrroles from alkenes via
 anti-Markovnikov selectivity
;
_journal_name_full               Chem.Commun.
_journal_page_first              13795
_journal_paper_doi               10.1039/C5cc05196G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C24 H16 N2 O'
_chemical_formula_sum            'C24 H16 N2 O'
_chemical_formula_weight         348.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-07 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.206(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.1944(9)
_cell_length_b                   9.7945(10)
_cell_length_c                   14.6162(10)
_cell_measurement_reflns_used    1294
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.6680
_cell_measurement_theta_min      2.9890
_cell_volume                     1859.0(3)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8872
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         2.83
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1403
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1476
_reflns_number_gt                2203
_reflns_number_total             4363
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05196g2.cif
_cod_data_source_block           pcn
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7117702
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O 0.56370(11) 0.21187(17) 0.23191(9) 0.0606(5) Uani 1 1 d . . .
N1 N 0.53672(13) 0.2516(2) 0.53311(12) 0.0469(5) Uani 1 1 d . . .
H1A H 0.5471(15) 0.261(2) 0.5973(16) 0.068(7) Uiso 1 1 d . . .
N2 N 0.04695(16) -0.0784(3) 0.65426(18) 0.0973(9) Uani 1 1 d . . .
C1 C 0.60267(15) 0.2991(2) 0.47889(13) 0.0427(5) Uani 1 1 d . . .
C2 C 0.56043(15) 0.2627(2) 0.38701(13) 0.0439(5) Uani 1 1 d . . .
C3 C 0.46747(15) 0.1926(2) 0.39048(13) 0.0501(6) Uani 1 1 d . . .
H3A H 0.4233 0.1565 0.3396 0.060 Uiso 1 1 calc R . .
C4 C 0.45314(15) 0.1864(2) 0.48066(13) 0.0451(5) Uani 1 1 d . . .
C5 C 0.69679(15) 0.3720(2) 0.52189(13) 0.0442(5) Uani 1 1 d . . .
C6 C 0.69009(18) 0.4838(3) 0.57801(14) 0.0574(6) Uani 1 1 d . . .
H6A H 0.6262 0.5119 0.5895 0.069 Uiso 1 1 calc R . .
C7 C 0.7776(2) 0.5542(3) 0.61713(17) 0.0767(8) Uani 1 1 d . . .
H7A H 0.7725 0.6297 0.6546 0.092 Uiso 1 1 calc R . .
C8 C 0.8724(2) 0.5131(4) 0.6009(2) 0.0851(9) Uani 1 1 d . . .
H8A H 0.9312 0.5612 0.6269 0.102 Uiso 1 1 calc R . .
C9 C 0.88026(19) 0.4016(3) 0.5464(2) 0.0783(8) Uani 1 1 d . . .
H9A H 0.9445 0.3733 0.5359 0.094 Uiso 1 1 calc R . .
C10 C 0.79279(17) 0.3309(3) 0.50689(15) 0.0574(6) Uani 1 1 d . . .
H10A H 0.7985 0.2550 0.4699 0.069 Uiso 1 1 calc R . .
C11 C 0.60016(15) 0.2819(2) 0.30080(13) 0.0474(6) Uani 1 1 d . . .
C12 C 0.68370(16) 0.3806(2) 0.29402(13) 0.0475(6) Uani 1 1 d . . .
C13 C 0.68508(17) 0.5113(2) 0.33072(14) 0.0552(6) Uani 1 1 d . . .
H13A H 0.6316 0.5405 0.3597 0.066 Uiso 1 1 calc R . .
C14 C 0.7659(2) 0.5980(3) 0.32424(17) 0.0688(7) Uani 1 1 d . . .
H14A H 0.7663 0.6859 0.3483 0.083 Uiso 1 1 calc R . .
C15 C 0.84597(19) 0.5554(3) 0.28238(18) 0.0733(8) Uani 1 1 d . . .
H15A H 0.9011 0.6135 0.2798 0.088 Uiso 1 1 calc R . .
C16 C 0.84440(18) 0.4274(3) 0.24452(18) 0.0711(8) Uani 1 1 d . . .
H16A H 0.8982 0.3989 0.2157 0.085 Uiso 1 1 calc R . .
C17 C 0.76317(17) 0.3406(3) 0.24904(14) 0.0581(6) Uani 1 1 d . . .
H17A H 0.7616 0.2547 0.2218 0.070 Uiso 1 1 calc R . .
C18 C 0.36911(15) 0.1271(2) 0.52042(14) 0.0465(5) Uani 1 1 d . . .
C19 C 0.27424(17) 0.1037(3) 0.46397(16) 0.0691(8) Uani 1 1 d . . .
H19A H 0.2662 0.1237 0.4009 0.083 Uiso 1 1 calc R . .
C20 C 0.19253(17) 0.0521(3) 0.49866(17) 0.0689(8) Uani 1 1 d . . .
H20A H 0.1297 0.0382 0.4595 0.083 Uiso 1 1 calc R . .
C21 C 0.20333(16) 0.0204(2) 0.59233(16) 0.0538(6) Uani 1 1 d . . .
C22 C 0.29710(16) 0.0384(2) 0.64883(15) 0.0567(6) Uani 1 1 d . . .
H22A H 0.3055 0.0148 0.7113 0.068 Uiso 1 1 calc R . .
C23 C 0.37905(16) 0.0914(2) 0.61346(14) 0.0533(6) Uani 1 1 d . . .
H23A H 0.4421 0.1034 0.6527 0.064 Uiso 1 1 calc R . .
C24 C 0.11664(18) -0.0343(3) 0.62810(17) 0.0673(7) 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'
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
C1 N1 C4 111.41(17) . .
C1 N1 H1A 124.0(13) . .
C4 N1 H1A 124.6(13) . .
N1 C1 C2 106.48(18) . .
N1 C1 C5 119.72(17) . .
C2 C1 C5 133.80(18) . .
C1 C2 C3 106.77(18) . .
C1 C2 C11 130.51(19) . .
C3 C2 C11 122.66(18) . .
C4 C3 C2 108.98(18) . .
C4 C3 H3A 125.5 . .
C2 C3 H3A 125.5 . .
C3 C4 N1 106.36(18) . .
C3 C4 C18 130.26(19) . .
N1 C4 C18 123.37(17) . .
C6 C5 C10 118.8(2) . .
C6 C5 C1 119.99(19) . .
C10 C5 C1 121.2(2) . .
C5 C6 C7 120.4(2) . .
C5 C6 H6A 119.8 . .
C7 C6 H6A 119.8 . .
C6 C7 C8 120.2(3) . .
C6 C7 H7A 119.9 . .
C8 C7 H7A 119.9 . .
C9 C8 C7 120.1(3) . .
C9 C8 H8A 120.0 . .
C7 C8 H8A 120.0 . .
C8 C9 C10 120.0(3) . .
C8 C9 H9A 120.0 . .
C10 C9 H9A 120.0 . .
C5 C10 C9 120.6(2) . .
C5 C10 H10A 119.7 . .
C9 C10 H10A 119.7 . .
O C11 C2 118.79(19) . .
O C11 C12 119.44(18) . .
C2 C11 C12 121.76(18) . .
C13 C12 C17 118.9(2) . .
C13 C12 C11 122.4(2) . .
C17 C12 C11 118.7(2) . .
C12 C13 C14 119.9(2) . .
C12 C13 H13A 120.0 . .
C14 C13 H13A 120.0 . .
C13 C14 C15 120.5(3) . .
C13 C14 H14A 119.7 . .
C15 C14 H14A 119.7 . .
C16 C15 C14 120.0(3) . .
C16 C15 H15A 120.0 . .
C14 C15 H15A 120.0 . .
C15 C16 C17 120.1(2) . .
C15 C16 H16A 120.0 . .
C17 C16 H16A 120.0 . .
C12 C17 C16 120.5(2) . .
C12 C17 H17A 119.8 . .
C16 C17 H17A 119.8 . .
C19 C18 C23 117.3(2) . .
C19 C18 C4 119.76(19) . .
C23 C18 C4 122.93(18) . .
C20 C19 C18 121.8(2) . .
C20 C19 H19A 119.1 . .
C18 C19 H19A 119.1 . .
C19 C20 C21 119.9(2) . .
C19 C20 H20A 120.0 . .
C21 C20 H20A 120.0 . .
C22 C21 C20 119.3(2) . .
C22 C21 C24 121.2(2) . .
C20 C21 C24 119.4(2) . .
C21 C22 C23 120.4(2) . .
C21 C22 H22A 119.8 . .
C23 C22 H22A 119.8 . .
C18 C23 C22 121.18(19) . .
C18 C23 H23A 119.4 . .
C22 C23 H23A 119.4 . .
N2 C24 C21 178.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O C11 1.243(2) .
N1 C1 1.359(2) .
N1 C4 1.382(2) .
N1 H1A 0.93(2) .
N2 C24 1.141(3) .
C1 C2 1.406(2) .
C1 C5 1.473(3) .
C2 C3 1.415(3) .
C2 C11 1.460(3) .
C3 C4 1.366(3) .
C3 H3A 0.9300 .
C4 C18 1.461(3) .
C5 C6 1.381(3) .
C5 C10 1.383(3) .
C6 C7 1.379(3) .
C6 H6A 0.9300 .
C7 C8 1.374(4) .
C7 H7A 0.9300 .
C8 C9 1.366(4) .
C8 H8A 0.9300 .
C9 C10 1.382(3) .
C9 H9A 0.9300 .
C10 H10A 0.9300 .
C11 C12 1.483(3) .
C12 C13 1.387(3) .
C12 C17 1.389(3) .
C13 C14 1.379(3) .
C13 H13A 0.9300 .
C14 C15 1.376(3) .
C14 H14A 0.9300 .
C15 C16 1.369(4) .
C15 H15A 0.9300 .
C16 C17 1.378(3) .
C16 H16A 0.9300 .
C17 H17A 0.9300 .
C18 C19 1.391(3) .
C18 C23 1.388(3) .
C19 C20 1.367(3) .
C19 H19A 0.9300 .
C20 C21 1.386(3) .
C20 H20A 0.9300 .
C21 C22 1.372(3) .
C21 C24 1.442(3) .
C22 C23 1.380(3) .
C22 H22A 0.9300 .
C23 H23A 0.9300 .
