#------------------------------------------------------------------------------
#$Date: 2015-08-31 09:44:14 +0200 (lun 31 de ago de 2015) $
#$Revision: 153818 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/76/7117699.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_7117699
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         'C22 H14 N2'
_chemical_formula_sum            'C22 H14 N2'
_chemical_formula_weight         306.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                83.981(8)
_cell_angle_beta                 81.526(8)
_cell_angle_gamma                76.578(8)
_cell_formula_units_Z            2
_cell_length_a                   5.8666(5)
_cell_length_b                   11.4535(10)
_cell_length_c                   12.2113(12)
_cell_measurement_reflns_used    1393
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.7440
_cell_measurement_theta_min      3.5870
_cell_volume                     787.26(13)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.855
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6123
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99412
_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            brown
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0539
_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)+(0.0485P)²+0.1069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                2541
_reflns_number_total             3630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05196g2.cif
_cod_data_source_block           sgcnitrile
_cod_original_cell_volume        787.26(12)
_cod_database_code               7117699
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.7683(3) 1.00540(14) 0.90902(12) 0.0274(4) Uani 1 1 d . . .
N2 N 1.9672(3) 0.36880(15) 0.90783(14) 0.0357(4) Uani 1 1 d . . .
C1 C 0.6349(3) 1.02861(15) 0.82284(14) 0.0216(4) Uani 1 1 d . . .
C2 C 0.4276(3) 1.12179(16) 0.83235(15) 0.0278(4) Uani 1 1 d . . .
H2A H 0.3918 1.1690 0.8947 0.033 Uiso 1 1 calc R . .
C3 C 0.2793(3) 1.14414(17) 0.75272(15) 0.0288(4) Uani 1 1 d . . .
H3A H 0.1387 1.2052 0.7607 0.035 Uiso 1 1 calc R . .
C4 C 0.3348(3) 1.07649(16) 0.65853(15) 0.0253(4) Uani 1 1 d . . .
H4A H 0.2311 1.0923 0.6033 0.030 Uiso 1 1 calc R . .
C5 C 0.5367(3) 0.98827(15) 0.64613(14) 0.0227(4) Uani 1 1 d . . .
H5A H 0.5740 0.9455 0.5809 0.027 Uiso 1 1 calc R . .
C6 C 0.6917(3) 0.95928(15) 0.72875(14) 0.0195(4) Uani 1 1 d . . .
C7 C 0.8958(3) 0.86229(15) 0.72330(14) 0.0191(4) Uani 1 1 d . . .
C8 C 1.0267(3) 0.83816(15) 0.81200(14) 0.0203(4) Uani 1 1 d . . .
C9 C 0.9522(3) 0.91412(16) 0.90190(15) 0.0255(4) Uani 1 1 d . . .
H9A H 1.0436 0.8973 0.9621 0.031 Uiso 1 1 calc R . .
C10 C 0.9588(3) 0.79096(14) 0.62273(14) 0.0194(4) Uani 1 1 d . . .
C11 C 0.8149(3) 0.71731(15) 0.60010(15) 0.0227(4) Uani 1 1 d . . .
H11A H 0.6754 0.7118 0.6490 0.027 Uiso 1 1 calc R . .
C12 C 0.8748(3) 0.65209(15) 0.50639(15) 0.0262(4) Uani 1 1 d . . .
H12A H 0.7770 0.6014 0.4920 0.031 Uiso 1 1 calc R . .
C13 C 1.0766(3) 0.66044(16) 0.43360(15) 0.0296(4) Uani 1 1 d . . .
H13A H 1.1175 0.6153 0.3698 0.036 Uiso 1 1 calc R . .
C14 C 1.2177(3) 0.73468(17) 0.45440(16) 0.0297(4) Uani 1 1 d . . .
H14A H 1.3549 0.7415 0.4043 0.036 Uiso 1 1 calc R . .
C15 C 1.1596(3) 0.79954(16) 0.54852(15) 0.0250(4) Uani 1 1 d . . .
H15A H 1.2579 0.8502 0.5623 0.030 Uiso 1 1 calc R . .
C16 C 1.2355(3) 0.73684(15) 0.82474(14) 0.0204(4) Uani 1 1 d . . .
C17 C 1.2483(3) 0.62129(16) 0.79140(15) 0.0233(4) Uani 1 1 d . . .
H17A H 1.1268 0.6083 0.7537 0.028 Uiso 1 1 calc R . .
C18 C 1.4343(3) 0.52641(16) 0.81244(14) 0.0244(4) Uani 1 1 d . . .
H18A H 1.4397 0.4490 0.7895 0.029 Uiso 1 1 calc R . .
C19 C 1.6138(3) 0.54445(16) 0.86725(14) 0.0232(4) Uani 1 1 d . . .
C20 C 1.6055(3) 0.65809(16) 0.90120(14) 0.0233(4) Uani 1 1 d . . .
H20A H 1.7276 0.6705 0.9388 0.028 Uiso 1 1 calc R . .
C21 C 1.4185(3) 0.75276(16) 0.87990(14) 0.0220(4) Uani 1 1 d . . .
H21A H 1.4141 0.8300 0.9031 0.026 Uiso 1 1 calc R . .
C22 C 1.8100(3) 0.44593(17) 0.88995(15) 0.0257(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 117.00(15) . .
N1 C1 C2 117.74(16) . .
N1 C1 C6 122.23(15) . .
C2 C1 C6 119.96(15) . .
C3 C2 C1 120.56(17) . .
C3 C2 H2A 119.7 . .
C1 C2 H2A 119.7 . .
C2 C3 C4 119.98(17) . .
C2 C3 H3A 120.0 . .
C4 C3 H3A 120.0 . .
C5 C4 C3 120.52(16) . .
C5 C4 H4A 119.7 . .
C3 C4 H4A 119.7 . .
C4 C5 C6 121.33(16) . .
C4 C5 H5A 119.3 . .
C6 C5 H5A 119.3 . .
C5 C6 C7 123.39(15) . .
C5 C6 C1 117.60(16) . .
C7 C6 C1 118.98(15) . .
C8 C7 C6 118.25(15) . .
C8 C7 C10 122.83(15) . .
C6 C7 C10 118.93(14) . .
C7 C8 C9 117.64(16) . .
C7 C8 C16 126.14(16) . .
C9 C8 C16 116.18(15) . .
N1 C9 C8 125.88(16) . .
N1 C9 H9A 117.1 . .
C8 C9 H9A 117.1 . .
C11 C10 C15 118.74(16) . .
C11 C10 C7 120.88(15) . .
C15 C10 C7 120.35(15) . .
C10 C11 C12 120.28(17) . .
C10 C11 H11A 119.9 . .
C12 C11 H11A 119.9 . .
C13 C12 C11 120.46(17) . .
C13 C12 H12A 119.8 . .
C11 C12 H12A 119.8 . .
C12 C13 C14 119.61(17) . .
C12 C13 H13A 120.2 . .
C14 C13 H13A 120.2 . .
C13 C14 C15 120.21(18) . .
C13 C14 H14A 119.9 . .
C15 C14 H14A 119.9 . .
C10 C15 C14 120.69(16) . .
C10 C15 H15A 119.7 . .
C14 C15 H15A 119.7 . .
C17 C16 C21 117.77(16) . .
C17 C16 C8 122.31(15) . .
C21 C16 C8 119.71(15) . .
C18 C17 C16 121.23(16) . .
C18 C17 H17A 119.4 . .
C16 C17 H17A 119.4 . .
C17 C18 C19 119.93(16) . .
C17 C18 H18A 120.0 . .
C19 C18 H18A 120.0 . .
C20 C19 C18 120.01(16) . .
C20 C19 C22 119.37(16) . .
C18 C19 C22 120.62(16) . .
C21 C20 C19 119.77(16) . .
C21 C20 H20A 120.1 . .
C19 C20 H20A 120.1 . .
C20 C21 C16 121.29(16) . .
C20 C21 H21A 119.4 . .
C16 C21 H21A 119.4 . .
N2 C22 C19 179.20(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C9 1.316(2) .
N1 C1 1.371(2) .
N2 C22 1.149(2) .
C1 C2 1.419(2) .
C1 C6 1.420(2) .
C2 C3 1.365(2) .
C2 H2A 0.9500 .
C3 C4 1.410(2) .
C3 H3A 0.9500 .
C4 C5 1.368(2) .
C4 H4A 0.9500 .
C5 C6 1.419(2) .
C5 H5A 0.9500 .
C6 C7 1.431(2) .
C7 C8 1.387(2) .
C7 C10 1.500(2) .
C8 C9 1.427(2) .
C8 C16 1.494(2) .
C9 H9A 0.9500 .
C10 C11 1.396(2) .
C10 C15 1.393(2) .
C11 C12 1.389(2) .
C11 H11A 0.9500 .
C12 C13 1.388(3) .
C12 H12A 0.9500 .
C13 C14 1.381(3) .
C13 H13A 0.9500 .
C14 C15 1.391(3) .
C14 H14A 0.9500 .
C15 H15A 0.9500 .
C16 C17 1.407(2) .
C16 C21 1.403(2) .
C17 C18 1.383(2) .
C17 H17A 0.9500 .
C18 C19 1.391(2) .
C18 H18A 0.9500 .
C19 C20 1.395(2) .
C19 C22 1.449(2) .
C20 C21 1.385(2) .
C20 H20A 0.9500 .
C21 H21A 0.9500 .
