#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/56/4025658.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_4025658
loop_
_publ_author_name
'Nitin T. Patil'
'Anil Kumar Mutyala'
'Pediredla G. V. V. Lakshmi'
'Balakrishna Gajula'
'Balasubramanian Sridhar'
'Gurava Reddy Pottireddygari'
'Tadikamalla Prabhakar Rao'
_publ_section_title
;
 Au(I)-Catalyzed Cascade Reaction Involving Formal Double Hydroamination
 of Alkynes Bearing Tethered Carboxylic Groups: An Easy Access to Fused
 Dihydrobenzimidazoles and Tetrahydroquinazolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5963
_journal_page_last               5975
_journal_paper_doi               10.1021/jo1013228
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H26 N2 O'
_chemical_formula_sum            'C22 H26 N2 O'
_chemical_formula_weight         334.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 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                   10.5601(6)
_cell_length_b                   13.1228(7)
_cell_length_c                   13.8186(8)
_cell_measurement_reflns_used    7647
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.69
_cell_measurement_theta_min      5.44
_cell_volume                     1914.96(19)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18515
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         1934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0407
_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)+(0.0656P)²+0.3725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                1771
_reflns_number_total             1934
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo1013228_si_001_1.cif
_cod_data_source_block           ah56m
_cod_original_cell_volume        1914.95(19)
_cod_database_code               4025658
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.5816(3) 0.40217(19) 1.01735(19) 0.0582(6) Uani 1 1 d . . .
C2 C 0.4948(3) 0.3509(2) 0.9615(2) 0.0769(9) Uani 1 1 d . . .
H2 H 0.4680 0.3762 0.9021 0.092 Uiso 1 1 calc R . .
C3 C 0.4490(4) 0.2589(3) 0.9984(4) 0.0986(12) Uani 1 1 d . . .
H3 H 0.3903 0.2217 0.9628 0.118 Uiso 1 1 calc R . .
C4 C 0.4891(5) 0.2228(3) 1.0860(3) 0.1050(14) Uani 1 1 d . . .
H4 H 0.4554 0.1620 1.1093 0.126 Uiso 1 1 calc R . .
C5 C 0.5778(4) 0.2737(2) 1.1410(3) 0.0910(11) Uani 1 1 d . . .
H5 H 0.6057 0.2474 1.1998 0.109 Uiso 1 1 calc R . .
C6 C 0.6243(3) 0.3656(2) 1.1056(2) 0.0629(7) Uani 1 1 d . . .
C7 C 0.7012(3) 0.52900(19) 1.09361(16) 0.0524(6) Uani 1 1 d . . .
C8 C 0.8249(3) 0.5784(2) 1.06286(19) 0.0637(7) Uani 1 1 d . . .
H8A H 0.8952 0.5319 1.0726 0.076 Uiso 1 1 calc R . .
H8B H 0.8404 0.6397 1.1002 0.076 Uiso 1 1 calc R . .
C9 C 0.8102(3) 0.6044(2) 0.95413(18) 0.0563(6) Uani 1 1 d . . .
C10 C 0.7113(3) 0.5262(2) 0.92194(17) 0.0558(6) Uani 1 1 d . . .
C11 C 0.6143(3) 0.5997(2) 1.1483(2) 0.0681(7) Uani 1 1 d . . .
H11A H 0.6500 0.6141 1.2107 0.102 Uiso 1 1 calc R . .
H11B H 0.5331 0.5679 1.1562 0.102 Uiso 1 1 calc R . .
H11C H 0.6046 0.6621 1.1127 0.102 Uiso 1 1 calc R . .
C12 C 0.9348(3) 0.5890(3) 0.8995(2) 0.0747(8) Uani 1 1 d . . .
H12A H 0.9213 0.6002 0.8316 0.112 Uiso 1 1 calc R . .
H12B H 0.9645 0.5206 0.9095 0.112 Uiso 1 1 calc R . .
H12C H 0.9968 0.6364 0.9231 0.112 Uiso 1 1 calc R . .
C13 C 0.7630(3) 0.7135(2) 0.93531(18) 0.0545(6) Uani 1 1 d . . .
C14 C 0.6653(3) 0.7345(2) 0.8727(2) 0.0622(7) Uani 1 1 d . . .
H14 H 0.6220 0.6811 0.8433 0.075 Uiso 1 1 calc R . .
C15 C 0.6299(3) 0.8347(2) 0.8527(2) 0.0713(8) Uani 1 1 d . . .
H15 H 0.5633 0.8470 0.8103 0.086 Uiso 1 1 calc R . .
C16 C 0.6925(3) 0.9163(2) 0.8950(2) 0.0725(8) Uani 1 1 d . . .
C17 C 0.7894(4) 0.8940(2) 0.9573(2) 0.0791(9) Uani 1 1 d . . .
H17 H 0.8323 0.9472 0.9874 0.095 Uiso 1 1 calc R . .
C18 C 0.8256(3) 0.7947(2) 0.9771(2) 0.0707(8) Uani 1 1 d . . .
H18 H 0.8929 0.7827 1.0190 0.085 Uiso 1 1 calc R . .
C19 C 0.6558(4) 1.0257(2) 0.8736(3) 0.0963(12) Uani 1 1 d . . .
H19A H 0.5658 1.0276 0.8596 0.116 Uiso 1 1 calc R . .
H19B H 0.6695 1.0657 0.9317 0.116 Uiso 1 1 calc R . .
C20 C 0.7217(7) 1.0735(3) 0.7955(4) 0.141(2) Uani 1 1 d . . .
H20 H 0.8030 1.0865 0.8273 0.169 Uiso 1 1 calc R . .
C21 C 0.7640(7) 1.0274(5) 0.7133(4) 0.152(2) Uani 1 1 d . . .
H21A H 0.6933 1.0003 0.6780 0.227 Uiso 1 1 calc R . .
H21B H 0.8207 0.9730 0.7301 0.227 Uiso 1 1 calc R . .
H21C H 0.8077 1.0762 0.6739 0.227 Uiso 1 1 calc R . .
C22 C 0.6767(7) 1.1842(3) 0.7815(4) 0.165(3) Uani 1 1 d . . .
H22A H 0.5880 1.1846 0.7663 0.248 Uiso 1 1 calc R . .
H22B H 0.7233 1.2150 0.7294 0.248 Uiso 1 1 calc R . .
H22C H 0.6909 1.2220 0.8400 0.248 Uiso 1 1 calc R . .
N1 N 0.7164(3) 0.43040(17) 1.14294(17) 0.0638(6) Uani 1 1 d . . .
N2 N 0.6450(2) 0.49579(15) 1.00093(14) 0.0525(5) Uani 1 1 d . . .
O1 O 0.6933(2) 0.49601(16) 0.83957(12) 0.0747(6) Uani 1 1 d . . .
H1N H 0.726(3) 0.436(3) 1.210(3) 0.087(11) Uiso 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 C6 122.8(3) . . ?
C2 C1 N2 130.5(3) . . ?
C6 C1 N2 106.7(2) . . ?
C1 C2 C3 116.7(3) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 N1 110.0(2) . . ?
C5 C6 N1 130.3(3) . . ?
N1 C7 N2 100.73(19) . . ?
N1 C7 C11 112.1(2) . . ?
N2 C7 C11 111.8(2) . . ?
N1 C7 C8 114.3(2) . . ?
N2 C7 C8 103.24(19) . . ?
C11 C7 C8 113.6(2) . . ?
C7 C8 C9 106.2(2) . . ?
C7 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C10 C9 C12 110.7(2) . . ?
C10 C9 C13 110.7(2) . . ?
C12 C9 C13 108.6(2) . . ?
C10 C9 C8 101.7(2) . . ?
C12 C9 C8 111.3(2) . . ?
C13 C9 C8 113.7(2) . . ?
O1 C10 N2 125.1(3) . . ?
O1 C10 C9 126.5(2) . . ?
N2 C10 C9 108.4(2) . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 117.9(3) . . ?
C14 C13 C9 122.5(2) . . ?
C18 C13 C9 119.5(2) . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 117.1(3) . . ?
C17 C16 C19 121.1(3) . . ?
C15 C16 C19 121.8(4) . . ?
C16 C17 C18 122.2(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C17 120.7(3) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C16 116.0(3) . . ?
C20 C19 H19A 108.3 . . ?
C16 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C16 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C21 C20 C19 126.4(5) . . ?
C21 C20 C22 114.6(4) . . ?
C19 C20 C22 111.0(5) . . ?
C21 C20 H20 99.4 . . ?
C19 C20 H20 99.4 . . ?
C22 C20 H20 99.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C6 N1 C7 106.8(2) . . ?
C6 N1 H1N 119(2) . . ?
C7 N1 H1N 114(2) . . ?
C10 N2 C1 128.9(2) . . ?
C10 N2 C7 113.77(19) . . ?
C1 N2 C7 107.86(19) . . ?
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 1.374(4) . ?
C1 C6 1.386(4) . ?
C1 N2 1.417(3) . ?
C2 C3 1.397(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.391(4) . ?
C7 N1 1.471(3) . ?
C7 N2 1.477(3) . ?
C7 C11 1.507(4) . ?
C7 C8 1.520(4) . ?
C8 C9 1.549(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.531(4) . ?
C9 C12 1.531(4) . ?
C9 C13 1.538(4) . ?
C10 O1 1.220(3) . ?
C10 N2 1.357(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.374(4) . ?
C13 C18 1.381(4) . ?
C14 C15 1.394(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(5) . ?
C16 C19 1.516(4) . ?
C17 C18 1.384(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.430(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.362(7) . ?
C20 C22 1.539(6) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 H1N 0.93(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.93(4) 2.18(4) 3.037(3) 153(3) 2_665
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
C6 C1 C2 C3 0.8(5) . . . . ?
N2 C1 C2 C3 -179.9(3) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 -1.4(7) . . . . ?
C3 C4 C5 C6 1.6(6) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
N2 C1 C6 C5 180.0(3) . . . . ?
C2 C1 C6 N1 176.7(3) . . . . ?
N2 C1 C6 N1 -2.8(3) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C4 C5 C6 N1 -177.2(3) . . . . ?
N1 C7 C8 C9 128.1(2) . . . . ?
N2 C7 C8 C9 19.7(3) . . . . ?
C11 C7 C8 C9 -101.6(3) . . . . ?
C7 C8 C9 C10 -25.6(3) . . . . ?
C7 C8 C9 C12 -143.5(2) . . . . ?
C7 C8 C9 C13 93.5(3) . . . . ?
C12 C9 C10 O1 -39.5(4) . . . . ?
C13 C9 C10 O1 81.0(4) . . . . ?
C8 C9 C10 O1 -157.8(3) . . . . ?
C12 C9 C10 N2 141.0(2) . . . . ?
C13 C9 C10 N2 -98.4(2) . . . . ?
C8 C9 C10 N2 22.7(3) . . . . ?
C10 C9 C13 C14 -18.0(3) . . . . ?
C12 C9 C13 C14 103.8(3) . . . . ?
C8 C9 C13 C14 -131.8(3) . . . . ?
C10 C9 C13 C18 166.6(2) . . . . ?
C12 C9 C13 C18 -71.6(3) . . . . ?
C8 C9 C13 C18 52.8(3) . . . . ?
C18 C13 C14 C15 -0.5(4) . . . . ?
C9 C13 C14 C15 -176.0(3) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C14 C15 C16 C19 179.7(3) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C19 C16 C17 C18 -179.3(3) . . . . ?
C14 C13 C18 C17 0.9(4) . . . . ?
C9 C13 C18 C17 176.5(3) . . . . ?
C16 C17 C18 C13 -1.2(5) . . . . ?
C17 C16 C19 C20 88.5(5) . . . . ?
C15 C16 C19 C20 -91.6(5) . . . . ?
C16 C19 C20 C21 33.5(10) . . . . ?
C16 C19 C20 C22 -179.6(5) . . . . ?
C1 C6 N1 C7 19.7(3) . . . . ?
C5 C6 N1 C7 -163.4(3) . . . . ?
N2 C7 N1 C6 -27.2(3) . . . . ?
C11 C7 N1 C6 91.8(3) . . . . ?
C8 C7 N1 C6 -137.1(2) . . . . ?
O1 C10 N2 C1 27.4(5) . . . . ?
C9 C10 N2 C1 -153.1(2) . . . . ?
O1 C10 N2 C7 169.1(3) . . . . ?
C9 C10 N2 C7 -11.4(3) . . . . ?
C2 C1 N2 C10 -51.2(4) . . . . ?
C6 C1 N2 C10 128.2(3) . . . . ?
C2 C1 N2 C7 165.4(3) . . . . ?
C6 C1 N2 C7 -15.3(3) . . . . ?
N1 C7 N2 C10 -123.8(2) . . . . ?
C11 C7 N2 C10 117.1(3) . . . . ?
C8 C7 N2 C10 -5.5(3) . . . . ?
N1 C7 N2 C1 25.8(3) . . . . ?
C11 C7 N2 C1 -93.4(3) . . . . ?
C8 C7 N2 C1 144.1(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659259
