#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:59:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178415 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/36/4023625.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_4023625
loop_
_publ_author_name
'Jhillu S. Yadav'
'Basi V. Subba Reddy'
'Nagendra Nath Yadav'
'Manoj K. Gupta'
'Balasubramanian Sridhar'
_publ_section_title
;
 Gold(III) Chloride-Catalyzed Three-Component Reaction:
 A Facile Synthesis of Alkynyl Derivatives of
 1,2-Dihydroquinolines and Isoquinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6857
_journal_page_last               6859
_journal_paper_doi               10.1021/jo8007034
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H27 N O4'
_chemical_formula_sum            'C27 H27 N O4'
_chemical_formula_weight         429.50
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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            4
_cell_length_a                   10.9098(8)
_cell_length_b                   21.5016(16)
_cell_length_c                   10.3485(8)
_cell_measurement_reflns_used    2696
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      20.30
_cell_measurement_theta_min      2.66
_cell_volume                     2427.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'ω scan'
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16841
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         0.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0503
_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)+(0.0845P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                1927
_reflns_number_total             2271
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo8007034_si_001.cif
_cod_data_source_block           ac97
_cod_database_code               4023625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
C1 C -0.0152(3) 0.54589(18) 0.3545(4) 0.0483(10) Uani 1 1 d . . .
H1 H -0.0266 0.5076 0.3143 0.058 Uiso 1 1 calc R . .
C2 C -0.0800(3) 0.59390(19) 0.3175(4) 0.0491(9) Uani 1 1 d . . .
H2 H -0.1338 0.5893 0.2485 0.059 Uiso 1 1 calc R . .
C3 C -0.0708(3) 0.65599(17) 0.3823(4) 0.0422(9) Uani 1 1 d . . .
H3 H -0.1538 0.6732 0.3877 0.051 Uiso 1 1 calc R . .
C4 C 0.0748(3) 0.55178(16) 0.4580(4) 0.0411(9) Uani 1 1 d . . .
C5 C 0.1659(4) 0.50772(19) 0.4806(5) 0.0557(11) Uani 1 1 d . . .
H5 H 0.1679 0.4715 0.4316 0.067 Uiso 1 1 calc R . .
C6 C 0.2534(5) 0.5173(2) 0.5753(5) 0.0646(12) Uani 1 1 d . . .
H6 H 0.3118 0.4868 0.5923 0.077 Uiso 1 1 calc R . .
C7 C 0.2538(4) 0.5720(2) 0.6440(5) 0.0609(11) Uani 1 1 d . . .
H7 H 0.3147 0.5792 0.7052 0.073 Uiso 1 1 calc R . .
C8 C 0.1642(3) 0.61660(18) 0.6228(4) 0.0469(9) Uani 1 1 d . . .
H8 H 0.1660 0.6540 0.6680 0.056 Uiso 1 1 calc R . .
C9 C 0.0729(3) 0.60539(15) 0.5352(3) 0.0362(8) Uani 1 1 d . . .
C10 C -0.0685(3) 0.68489(15) 0.6128(3) 0.0375(8) Uani 1 1 d . . .
C11 C -0.0627(4) 0.65611(17) 0.7458(4) 0.0409(8) Uani 1 1 d . . .
C12 C 0.0135(7) 0.6636(3) 0.9565(5) 0.104(2) Uani 1 1 d . . .
H12A H 0.0287 0.6196 0.9545 0.156 Uiso 1 1 calc R . .
H12B H -0.0632 0.6714 0.9989 0.156 Uiso 1 1 calc R . .
H12C H 0.0783 0.6839 1.0029 0.156 Uiso 1 1 calc R . .
C13 C -0.1277(3) 0.73920(16) 0.5934(4) 0.0483(9) Uani 1 1 d . . .
H13 H -0.1292 0.7562 0.5108 0.058 Uiso 1 1 calc R . .
C14 C -0.1893(4) 0.77178(19) 0.6978(5) 0.0539(10) Uani 1 1 d . . .
C15 C -0.2817(7) 0.8651(2) 0.7613(8) 0.113(3) Uani 1 1 d . . .
H15A H -0.2334 0.8653 0.8388 0.169 Uiso 1 1 calc R . .
H15B H -0.3599 0.8464 0.7787 0.169 Uiso 1 1 calc R . .
H15C H -0.2936 0.9070 0.7319 0.169 Uiso 1 1 calc R . .
C16 C 0.0051(4) 0.70086(19) 0.3107(4) 0.0497(10) Uani 1 1 d . . .
C17 C 0.0678(4) 0.73882(19) 0.2586(4) 0.0537(10) Uani 1 1 d . . .
C18 C 0.1445(4) 0.78589(18) 0.1999(4) 0.0514(10) Uani 1 1 d . . .
C19 C 0.2649(5) 0.7930(2) 0.2377(5) 0.0678(13) Uani 1 1 d . . .
H19 H 0.2985 0.7658 0.2980 0.081 Uiso 1 1 calc R . .
C20 C 0.3359(4) 0.8401(2) 0.1867(6) 0.0718(14) Uani 1 1 d . . .
H20 H 0.4166 0.8441 0.2143 0.086 Uiso 1 1 calc R . .
C21 C 0.2919(4) 0.88119(18) 0.0970(4) 0.0548(11) Uani 1 1 d . . .
C22 C 0.1726(4) 0.8731(2) 0.0581(5) 0.0679(12) Uani 1 1 d . . .
H22 H 0.1395 0.9001 -0.0027 0.081 Uiso 1 1 calc R . .
C23 C 0.1001(4) 0.8256(2) 0.1073(5) 0.0665(12) Uani 1 1 d . . .
H23 H 0.0204 0.8206 0.0770 0.080 Uiso 1 1 calc R . .
C24 C 0.3734(4) 0.93349(19) 0.0436(6) 0.0675(11) Uani 1 1 d U . .
C25 C 0.4675(7) 0.9062(3) -0.0457(9) 0.124(3) Uani 1 1 d U . .
H25A H 0.5261 0.9376 -0.0688 0.186 Uiso 1 1 calc R . .
H25B H 0.4278 0.8910 -0.1223 0.186 Uiso 1 1 calc R . .
H25C H 0.5087 0.8725 -0.0032 0.186 Uiso 1 1 calc R . .
C26 C 0.3022(6) 0.9831(3) -0.0243(12) 0.162(4) Uani 1 1 d U . .
H26A H 0.2651 0.9660 -0.1005 0.243 Uiso 1 1 calc R . .
H26B H 0.3563 1.0163 -0.0482 0.243 Uiso 1 1 calc R . .
H26C H 0.2396 0.9987 0.0322 0.243 Uiso 1 1 calc R . .
C27 C 0.4426(7) 0.9656(3) 0.1553(8) 0.126(2) Uani 1 1 d U . .
H27A H 0.3847 0.9811 0.2172 0.189 Uiso 1 1 calc R . .
H27B H 0.4902 0.9995 0.1217 0.189 Uiso 1 1 calc R . .
H27C H 0.4961 0.9361 0.1963 0.189 Uiso 1 1 calc R . .
N1 N -0.0258(3) 0.64759(13) 0.5157(3) 0.0398(7) Uani 1 1 d . . .
O1 O -0.2120(3) 0.75201(13) 0.8038(3) 0.0709(10) Uani 1 1 d . . .
O2 O -0.2193(4) 0.82993(13) 0.6630(4) 0.0879(12) Uani 1 1 d . . .
O3 O -0.1173(3) 0.60958(13) 0.7714(3) 0.0575(8) Uani 1 1 d . . .
O4 O 0.0088(3) 0.68726(13) 0.8262(3) 0.0580(8) 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
_geom_angle_publ_flag
C2 C1 C4 120.7(4) . . ?
C2 C1 H1 119.7 . . ?
C4 C1 H1 119.7 . . ?
C1 C2 C3 122.4(4) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C16 C3 N1 111.3(3) . . ?
C16 C3 C2 113.4(3) . . ?
N1 C3 C2 109.4(3) . . ?
C16 C3 H3 107.5 . . ?
N1 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
C5 C4 C9 118.3(4) . . ?
C5 C4 C1 123.0(4) . . ?
C9 C4 C1 118.7(3) . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 119.7(4) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.5(4) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.8(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 120.8(3) . . ?
C8 C9 N1 122.2(3) . . ?
C4 C9 N1 117.0(3) . . ?
C13 C10 N1 124.2(3) . . ?
C13 C10 C11 120.7(3) . . ?
N1 C10 C11 114.5(3) . . ?
O3 C11 O4 125.4(4) . . ?
O3 C11 C10 121.6(3) . . ?
O4 C11 C10 113.0(3) . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 C14 121.9(4) . . ?
C10 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
O1 C14 O2 121.6(4) . . ?
O1 C14 C13 127.1(4) . . ?
O2 C14 C13 111.2(4) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C3 176.6(4) . . ?
C16 C17 C18 177.9(4) . . ?
C23 C18 C19 117.8(4) . . ?
C23 C18 C17 121.6(4) . . ?
C19 C18 C17 120.6(4) . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 122.5(4) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C20 C21 C22 116.7(4) . . ?
C20 C21 C24 120.9(4) . . ?
C22 C21 C24 122.4(4) . . ?
C21 C22 C23 121.7(4) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C18 C23 C22 120.8(4) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C26 C24 C25 110.2(7) . . ?
C26 C24 C21 112.9(4) . . ?
C25 C24 C21 109.3(4) . . ?
C26 C24 C27 106.7(6) . . ?
C25 C24 C27 107.6(5) . . ?
C21 C24 C27 110.0(5) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C10 N1 C9 121.9(3) . . ?
C10 N1 C3 120.1(3) . . ?
C9 N1 C3 117.6(3) . . ?
C14 O2 C15 114.5(4) . . ?
C11 O4 C12 115.5(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.309(5) . ?
C1 C4 1.459(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.497(5) . ?
C2 H2 0.9300 . ?
C3 C16 1.472(6) . ?
C3 N1 1.476(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.393(5) . ?
C4 C9 1.403(5) . ?
C5 C6 1.383(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(5) . ?
C8 H8 0.9300 . ?
C9 N1 1.422(4) . ?
C10 C13 1.349(5) . ?
C10 N1 1.368(4) . ?
C10 C11 1.511(5) . ?
C11 O3 1.194(4) . ?
C11 O4 1.323(5) . ?
C12 O4 1.443(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.452(6) . ?
C13 H13 0.9300 . ?
C14 O1 1.202(5) . ?
C14 O2 1.342(5) . ?
C15 O2 1.439(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.194(5) . ?
C17 C18 1.447(6) . ?
C18 C23 1.372(6) . ?
C18 C19 1.379(6) . ?
C19 C20 1.380(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(6) . ?
C21 C24 1.537(6) . ?
C22 C23 1.388(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C26 1.494(8) . ?
C24 C25 1.500(8) . ?
C24 C27 1.543(9) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C1 C2 C3 -3.1(6) . . . . ?
C1 C2 C3 C16 100.9(4) . . . . ?
C1 C2 C3 N1 -23.9(5) . . . . ?
C2 C1 C4 C5 -164.1(4) . . . . ?
C2 C1 C4 C9 13.3(5) . . . . ?
C9 C4 C5 C6 -1.2(6) . . . . ?
C1 C4 C5 C6 176.2(4) . . . . ?
C4 C5 C6 C7 -2.8(7) . . . . ?
C5 C6 C7 C8 2.6(7) . . . . ?
C6 C7 C8 C9 1.6(6) . . . . ?
C7 C8 C9 C4 -5.8(6) . . . . ?
C7 C8 C9 N1 175.8(4) . . . . ?
C5 C4 C9 C8 5.6(5) . . . . ?
C1 C4 C9 C8 -172.0(3) . . . . ?
C5 C4 C9 N1 -176.0(3) . . . . ?
C1 C4 C9 N1 6.5(5) . . . . ?
C13 C10 C11 O3 110.1(4) . . . . ?
N1 C10 C11 O3 -61.0(5) . . . . ?
C13 C10 C11 O4 -70.7(5) . . . . ?
N1 C10 C11 O4 118.2(3) . . . . ?
N1 C10 C13 C14 169.4(3) . . . . ?
C11 C10 C13 C14 -0.8(6) . . . . ?
C10 C13 C14 O1 -12.2(7) . . . . ?
C10 C13 C14 O2 167.2(4) . . . . ?
C23 C18 C19 C20 2.3(7) . . . . ?
C17 C18 C19 C20 -176.4(5) . . . . ?
C18 C19 C20 C21 -0.5(8) . . . . ?
C19 C20 C21 C22 -0.7(7) . . . . ?
C19 C20 C21 C24 179.3(5) . . . . ?
C20 C21 C22 C23 0.0(7) . . . . ?
C24 C21 C22 C23 180.0(5) . . . . ?
C19 C18 C23 C22 -3.0(7) . . . . ?
C17 C18 C23 C22 175.8(4) . . . . ?
C21 C22 C23 C18 1.9(7) . . . . ?
C20 C21 C24 C26 -164.5(7) . . . . ?
C22 C21 C24 C26 15.5(8) . . . . ?
C20 C21 C24 C25 72.4(7) . . . . ?
C22 C21 C24 C25 -107.6(6) . . . . ?
C20 C21 C24 C27 -45.4(6) . . . . ?
C22 C21 C24 C27 134.5(5) . . . . ?
C13 C10 N1 C9 155.4(3) . . . . ?
C11 C10 N1 C9 -33.8(4) . . . . ?
C13 C10 N1 C3 -16.7(5) . . . . ?
C11 C10 N1 C3 154.1(3) . . . . ?
C8 C9 N1 C10 -29.9(5) . . . . ?
C4 C9 N1 C10 151.6(3) . . . . ?
C8 C9 N1 C3 142.4(4) . . . . ?
C4 C9 N1 C3 -36.1(4) . . . . ?
C16 C3 N1 C10 89.7(4) . . . . ?
C2 C3 N1 C10 -144.3(3) . . . . ?
C16 C3 N1 C9 -82.7(4) . . . . ?
C2 C3 N1 C9 43.3(4) . . . . ?
O1 C14 O2 C15 -1.1(7) . . . . ?
C13 C14 O2 C15 179.5(5) . . . . ?
O3 C11 O4 C12 -3.6(6) . . . . ?
C10 C11 O4 C12 177.3(4) . . . . ?
