#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117701.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_7117701
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         'C16 H10 N2'
_chemical_formula_sum            'C16 H10 N2'
_chemical_formula_weight         230.26
_space_group_IT_number           14
_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_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                 106.572(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4760(11)
_cell_length_b                   6.7685(5)
_cell_length_c                   15.8831(16)
_cell_measurement_reflns_used    952
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      28.9680
_cell_measurement_theta_min      3.2840
_cell_volume                     1182.5(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.864
_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  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5267
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.22
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98218
_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            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0550
_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)+(0.0606P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                1598
_reflns_number_total             2774
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05196g2.cif
_cod_data_source_block           rp9162
_cod_original_cell_volume        1182.48(19)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7117701
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33179(13) 0.17539(18) 0.30142(11) 0.0444(4) Uani 1 1 d . . .
N2 N -0.00196(15) 0.2016(3) 0.42297(12) 0.0629(5) Uani 1 1 d . . .
C1 C 0.28201(16) 0.1769(2) 0.21247(13) 0.0396(4) Uani 1 1 d . . .
C2 C 0.36101(18) 0.1716(2) 0.15887(16) 0.0516(5) Uani 1 1 d . . .
H2A H 0.4446 0.1692 0.1848 0.062 Uiso 1 1 calc R . .
C3 C 0.3171(2) 0.1699(3) 0.07035(17) 0.0601(6) Uani 1 1 d . . .
H3A H 0.3706 0.1681 0.0361 0.072 Uiso 1 1 calc R . .
C4 C 0.1914(2) 0.1707(3) 0.02993(14) 0.0597(6) Uani 1 1 d . . .
H4A H 0.1621 0.1672 -0.0310 0.072 Uiso 1 1 calc R . .
C5 C 0.11183(18) 0.1767(2) 0.07914(13) 0.0490(5) Uani 1 1 d . . .
H5A H 0.0287 0.1776 0.0514 0.059 Uiso 1 1 calc R . .
C6 C 0.15417(15) 0.1815(2) 0.17184(12) 0.0361(4) Uani 1 1 d . . .
C7 C 0.07586(15) 0.1868(2) 0.22664(11) 0.0342(4) Uani 1 1 d . . .
C8 C 0.12890(15) 0.1817(2) 0.31580(12) 0.0358(4) Uani 1 1 d . . .
C9 C 0.25718(16) 0.1765(2) 0.35001(13) 0.0423(4) Uani 1 1 d . . .
H9A H 0.2902 0.1737 0.4107 0.051 Uiso 1 1 calc R . .
C10 C -0.05838(15) 0.1973(2) 0.18946(11) 0.0386(4) Uani 1 1 d . . .
C11 C -0.11272(18) 0.3608(3) 0.14198(13) 0.0520(5) Uani 1 1 d . . .
H11A H -0.0651 0.4649 0.1325 0.062 Uiso 1 1 calc R . .
C12 C -0.23721(19) 0.3694(3) 0.10872(14) 0.0680(6) Uani 1 1 d . . .
H12A H -0.2734 0.4800 0.0772 0.082 Uiso 1 1 calc R . .
C13 C -0.30804(19) 0.2169(4) 0.12172(14) 0.0717(7) Uani 1 1 d . . .
H13A H -0.3920 0.2230 0.0982 0.086 Uiso 1 1 calc R . .
C14 C -0.25582(19) 0.0555(4) 0.16923(14) 0.0683(6) Uani 1 1 d . . .
H14A H -0.3043 -0.0475 0.1786 0.082 Uiso 1 1 calc R . .
C15 C -0.13120(17) 0.0449(3) 0.20336(13) 0.0527(5) Uani 1 1 d . . .
H15A H -0.0959 -0.0650 0.2359 0.063 Uiso 1 1 calc R . .
C16 C 0.05592(16) 0.1916(2) 0.37580(12) 0.0423(4) 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'
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
C9 N1 C1 117.41(16) . .
N1 C1 C2 118.26(18) . .
N1 C1 C6 122.82(16) . .
C2 C1 C6 118.91(19) . .
C3 C2 C1 121.0(2) . .
C3 C2 H2A 119.5 . .
C1 C2 H2A 119.5 . .
C2 C3 C4 120.40(19) . .
C2 C3 H3A 119.8 . .
C4 C3 H3A 119.8 . .
C5 C4 C3 120.6(2) . .
C5 C4 H4A 119.7 . .
C3 C4 H4A 119.7 . .
C4 C5 C6 120.7(2) . .
C4 C5 H5A 119.6 . .
C6 C5 H5A 119.6 . .
C5 C6 C7 123.37(17) . .
C5 C6 C1 118.37(16) . .
C7 C6 C1 118.25(16) . .
C8 C7 C6 117.38(15) . .
C8 C7 C10 121.03(15) . .
C6 C7 C10 121.59(16) . .
C7 C8 C9 120.18(16) . .
C7 C8 C16 120.76(16) . .
C9 C8 C16 118.98(16) . .
N1 C9 C8 123.92(18) . .
N1 C9 H9A 118.0 . .
C8 C9 H9A 118.0 . .
C15 C10 C11 118.95(17) . .
C15 C10 C7 120.37(15) . .
C11 C10 C7 120.67(15) . .
C12 C11 C10 120.05(18) . .
C12 C11 H11A 120.0 . .
C10 C11 H11A 120.0 . .
C13 C12 C11 120.5(2) . .
C13 C12 H12A 119.8 . .
C11 C12 H12A 119.8 . .
C14 C13 C12 120.1(2) . .
C14 C13 H13A 119.9 . .
C12 C13 H13A 119.9 . .
C13 C14 C15 120.1(2) . .
C13 C14 H14A 120.0 . .
C15 C14 H14A 120.0 . .
C10 C15 C14 120.28(19) . .
C10 C15 H15A 119.9 . .
C14 C15 H15A 119.9 . .
N2 C16 C8 179.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C9 1.306(2) .
N1 C1 1.365(2) .
N2 C16 1.136(2) .
C1 C2 1.410(2) .
C1 C6 1.425(2) .
C2 C3 1.351(3) .
C2 H2A 0.9300 .
C3 C4 1.402(3) .
C3 H3A 0.9300 .
C4 C5 1.361(2) .
C4 H4A 0.9300 .
C5 C6 1.413(3) .
C5 H5A 0.9300 .
C6 C7 1.419(2) .
C7 C8 1.373(2) .
C7 C10 1.486(2) .
C8 C9 1.417(2) .
C8 C16 1.439(2) .
C9 H9A 0.9300 .
C10 C15 1.384(2) .
C10 C11 1.383(2) .
C11 C12 1.376(3) .
C11 H11A 0.9300 .
C12 C13 1.365(3) .
C12 H12A 0.9300 .
C13 C14 1.366(3) .
C13 H13A 0.9300 .
C14 C15 1.379(3) .
C14 H14A 0.9300 .
C15 H15A 0.9300 .
