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#$Date: 2016-03-21 04:19:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178465 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/86/4028675.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_4028675
loop_
_publ_author_name
'Bifu Liu'
'Hanling Gao'
'Yue Yu'
'Wanqing Wu'
'Huanfeng Jiang'
_publ_section_title
;
 Palladium-Catalyzed Intermolecular Aerobic Oxidative Cyclization of
 2-Ethynylanilines with Isocyanides: Regioselective Synthesis of
 4-Halo-2-aminoquinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10319
_journal_page_last               10328
_journal_paper_doi               10.1021/jo401707j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C19 H18 Br Cl N2'
_chemical_formula_weight         389.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           114
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.320(3)
_cell_length_b                   20.320(3)
_cell_length_c                   8.7899(18)
_cell_measurement_temperature    293(2)
_cell_volume                     3629.4(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            53330
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    2.413
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             1584
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(13)
_refine_ls_extinction_coef       0.0206(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0506
_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)+(0.0981P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                2757
_reflns_number_total             4149
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401707j_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        3629.3(10)
_cod_database_code               4028675
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+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
Br1 Br 0.40210(3) 0.52118(3) 0.13695(8) 0.1150(3) Uani 1 1 d .
Cl1 Cl 0.18780(6) 0.44748(5) 0.67270(15) 0.0799(4) Uani 1 1 d .
C1 C 0.18758(19) 0.57950(19) 1.0099(5) 0.0595(9) Uani 1 1 d .
N1 N 0.31427(17) 0.65636(16) 0.7906(4) 0.0658(9) Uani 1 1 d .
H1A H 0.3364 0.6446 0.7118 0.079 Uiso 1 1 calc R
C13 C 0.3575(2) 0.5312(2) 0.3280(6) 0.0724(11) Uani 1 1 d .
C5 C 0.1228(2) 0.4796(2) 0.9818(6) 0.0728(12) Uani 1 1 d .
H5A H 0.1122 0.4421 0.9262 0.087 Uiso 1 1 calc R
N2 N 0.23499(17) 0.62388(17) 0.9674(4) 0.0620(8) Uani 1 1 d .
C14 C 0.3071(2) 0.5770(2) 0.3315(5) 0.0738(11) Uani 1 1 d .
H14A H 0.2956 0.6015 0.2462 0.089 Uiso 1 1 calc R
C6 C 0.17184(18) 0.52265(19) 0.9274(4) 0.0597(9) Uani 1 1 d .
C7 C 0.20709(18) 0.51382(18) 0.7888(4) 0.0580(9) Uani 1 1 d .
C16 C 0.33192(19) 0.71976(18) 0.8559(5) 0.0612(9) Uani 1 1 d .
C19 C 0.3802(3) 0.7511(3) 0.7485(6) 0.0817(14) Uani 1 1 d .
H19A H 0.3598 0.7571 0.6509 0.123 Uiso 1 1 calc R
H19B H 0.4180 0.7232 0.7378 0.123 Uiso 1 1 calc R
H19C H 0.3936 0.7931 0.7881 0.123 Uiso 1 1 calc R
C9 C 0.26696(18) 0.61305(17) 0.8388(5) 0.0559(8) Uani 1 1 d .
C2 C 0.1540(2) 0.5926(2) 1.1485(5) 0.0752(11) Uani 1 1 d .
H2A H 0.1639 0.6295 1.2064 0.090 Uiso 1 1 calc R
C8 C 0.25471(19) 0.55612(19) 0.7423(4) 0.0552(8) Uani 1 1 d .
C15 C 0.2745(2) 0.5843(2) 0.4700(5) 0.0702(11) Uani 1 1 d .
H15A H 0.2403 0.6145 0.4772 0.084 Uiso 1 1 calc R
C10 C 0.29152(18) 0.54794(18) 0.5970(4) 0.0560(8) Uani 1 1 d .
C11 C 0.3425(2) 0.5022(2) 0.5863(5) 0.0715(11) Uani 1 1 d .
H11A H 0.3542 0.4767 0.6698 0.086 Uiso 1 1 calc R
C12 C 0.3758(2) 0.4953(3) 0.4478(7) 0.0825(14) Uani 1 1 d .
H12A H 0.4107 0.4659 0.4394 0.099 Uiso 1 1 calc R
C4 C 0.0909(2) 0.4919(2) 1.1130(6) 0.0836(13) Uani 1 1 d .
H4A H 0.0590 0.4630 1.1490 0.100 Uiso 1 1 calc R
C18 C 0.2705(2) 0.7631(2) 0.8659(6) 0.0887(14) Uani 1 1 d .
H18A H 0.2516 0.7679 0.7665 0.133 Uiso 1 1 calc R
H18B H 0.2824 0.8056 0.9048 0.133 Uiso 1 1 calc R
H18C H 0.2391 0.7429 0.9328 0.133 Uiso 1 1 calc R
C17 C 0.3645(3) 0.7097(3) 1.0143(6) 0.0869(15) Uani 1 1 d .
H17A H 0.4030 0.6828 1.0034 0.130 Uiso 1 1 calc R
H17B H 0.3339 0.6884 1.0813 0.130 Uiso 1 1 calc R
H17C H 0.3766 0.7516 1.0559 0.130 Uiso 1 1 calc R
C3 C 0.1066(3) 0.5489(3) 1.1939(7) 0.0935(16) Uani 1 1 d .
H3A H 0.0837 0.5576 1.2832 0.112 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 0.0000 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
N2 C1 C6 124.1(4)
N2 C1 C2 116.6(4)
C6 C1 C2 119.2(4)
C9 N1 C16 128.3(3)
C12 C13 C14 123.8(4)
C12 C13 Br1 120.1(4)
C14 C13 Br1 116.1(4)
C4 C5 C6 121.0(5)
C9 N2 C1 118.0(3)
C13 C14 C15 116.3(4)
C1 C6 C5 119.8(4)
C1 C6 C7 115.6(3)
C5 C6 C7 124.6(4)
C8 C7 C6 122.4(4)
C8 C7 Cl1 118.4(3)
C6 C7 Cl1 119.2(3)
N1 C16 C19 106.8(3)
N1 C16 C18 109.4(3)
C19 C16 C18 108.9(4)
N1 C16 C17 109.9(4)
C19 C16 C17 109.9(4)
C18 C16 C17 111.8(4)
N2 C9 N1 120.1(3)
N2 C9 C8 123.1(3)
N1 C9 C8 116.7(3)
C3 C2 C1 117.8(4)
C7 C8 C9 116.7(3)
C7 C8 C10 123.1(3)
C9 C8 C10 120.2(3)
C10 C15 C14 122.0(4)
C15 C10 C11 119.1(4)
C15 C10 C8 120.5(3)
C11 C10 C8 120.4(3)
C10 C11 C12 119.0(4)
C13 C12 C11 119.8(4)
C5 C4 C3 118.8(5)
C2 C3 C4 123.4(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C13 1.919(5)
Cl1 C7 1.735(4)
C1 N2 1.372(5)
C1 C6 1.401(6)
C1 C2 1.421(6)
N1 C9 1.370(5)
N1 C16 1.455(5)
C13 C12 1.333(7)
C13 C14 1.384(7)
C5 C4 1.346(7)
C5 C6 1.410(6)
N2 C9 1.322(5)
C14 C15 1.394(6)
C6 C7 1.425(5)
C7 C8 1.357(5)
C16 C19 1.503(6)
C16 C18 1.529(6)
C16 C17 1.555(7)
C9 C8 1.456(5)
C2 C3 1.369(7)
C8 C10 1.489(5)
C15 C10 1.382(6)
C10 C11 1.395(6)
C11 C12 1.400(7)
C4 C3 1.395(8)
