#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:35:45 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178433 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/54/4025430.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_4025430
loop_
_publ_author_name
'Nitin T. Patil'
'Rahul D. Kavthe'
'Valmik S. Shinde'
'Balasubramanian Sridhar'
_publ_section_title
;
 Pt(IV)-Catalyzed Hydroamination Triggered Cyclization: A Strategy to
 Fused Pyrrolo[1,2-a]quinoxalines, Indolo[1,2-a]quinoxalines, and
 Indolo[3,2-c]quinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3371
_journal_page_last               3380
_journal_paper_doi               10.1021/jo100373w
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C17 H18 N2 O2'
_chemical_formula_sum            'C17 H18 N2 O2'
_chemical_formula_weight         282.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_cell_angle_alpha                98.359(1)
_cell_angle_beta                 101.378(1)
_cell_angle_gamma                109.283(1)
_cell_formula_units_Z            2
_cell_length_a                   8.1163(7)
_cell_length_b                   8.4645(7)
_cell_length_c                   11.6804(9)
_cell_measurement_reflns_used    5007
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.61
_cell_volume                     723.07(10)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6955
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.046(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0431
_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)+(0.0694P)²+0.1074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2318
_reflns_number_total             2534
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo100373w_si_004.cif
_cod_data_source_block           ah52m
_cod_database_code               4025430
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
C1 C 0.17795(17) 0.04461(17) 0.41056(11) 0.0487(3) Uani 1 1 d . . .
C2 C 0.25091(16) 0.22106(16) 0.48525(11) 0.0454(3) Uani 1 1 d . . .
C3 C 0.40844(16) 0.27131(16) 0.57752(11) 0.0448(3) Uani 1 1 d . . .
H3 H 0.4677 0.1954 0.5888 0.054 Uiso 1 1 calc R . .
C4 C 0.47690(16) 0.43289(15) 0.65223(10) 0.0429(3) Uani 1 1 d . . .
C5 C 0.77616(18) 0.42719(19) 0.75548(13) 0.0588(4) Uani 1 1 d . . .
H5 H 0.7729 0.3273 0.7082 0.071 Uiso 1 1 calc R . .
C6 C 0.9144(2) 0.5343(2) 0.84899(15) 0.0726(5) Uani 1 1 d . . .
H6 H 1.0227 0.5201 0.8777 0.087 Uiso 1 1 calc R . .
C7 C 0.8663(2) 0.6709(2) 0.89545(14) 0.0690(4) Uani 1 1 d . . .
H7 H 0.9369 0.7628 0.9599 0.083 Uiso 1 1 calc R . .
C8 C 0.69788(18) 0.64408(17) 0.82891(11) 0.0526(3) Uani 1 1 d . . .
C9 C 0.56854(18) 0.73384(16) 0.83617(11) 0.0493(3) Uani 1 1 d . . .
C10 C 0.6548(2) 0.92996(17) 0.87155(13) 0.0601(4) Uani 1 1 d . . .
H10A H 0.6901 0.9711 0.9580 0.072 Uiso 1 1 calc R . .
H10B H 0.7604 0.9716 0.8412 0.072 Uiso 1 1 calc R . .
C11 C 0.5063(2) 0.98758(19) 0.81344(14) 0.0693(4) Uani 1 1 d . . .
H11A H 0.5579 1.0949 0.7901 0.083 Uiso 1 1 calc R . .
H11B H 0.4351 1.0039 0.8686 0.083 Uiso 1 1 calc R . .
C12 C 0.3892(2) 0.84430(18) 0.70347(14) 0.0640(4) Uani 1 1 d . . .
H12A H 0.2629 0.8056 0.7042 0.077 Uiso 1 1 calc R . .
H12B H 0.4009 0.8827 0.6301 0.077 Uiso 1 1 calc R . .
C13 C 0.38818(17) 0.55015(16) 0.63726(11) 0.0447(3) Uani 1 1 d . . .
C14 C 0.23506(18) 0.50010(17) 0.54125(12) 0.0520(3) Uani 1 1 d . . .
H14 H 0.1777 0.5767 0.5273 0.062 Uiso 1 1 calc R . .
C15 C 0.16784(17) 0.33837(17) 0.46684(12) 0.0510(3) Uani 1 1 d . . .
H15 H 0.0654 0.3073 0.4034 0.061 Uiso 1 1 calc R . .
C16 C 0.4476(2) 0.66302(19) 0.91713(14) 0.0652(4) Uani 1 1 d . . .
H16A H 0.3640 0.7206 0.9195 0.098 Uiso 1 1 calc R . .
H16B H 0.5214 0.6822 0.9967 0.098 Uiso 1 1 calc R . .
H16C H 0.3818 0.5420 0.8858 0.098 Uiso 1 1 calc R . .
C17 C -0.0670(2) -0.1627(2) 0.25876(14) 0.0669(4) Uani 1 1 d . . .
H17A H 0.0070 -0.1805 0.2072 0.100 Uiso 1 1 calc R . .
H17B H -0.1839 -0.1772 0.2110 0.100 Uiso 1 1 calc R . .
H17C H -0.0803 -0.2447 0.3084 0.100 Uiso 1 1 calc R . .
N1 N 0.45970(15) 0.70828(14) 0.71394(9) 0.0522(3) Uani 1 1 d . . .
N2 N 0.64135(14) 0.49285(13) 0.74312(9) 0.0480(3) Uani 1 1 d . . .
O1 O 0.25031(14) -0.05869(13) 0.41668(9) 0.0687(3) Uani 1 1 d . . .
O2 O 0.01725(13) 0.00823(12) 0.33320(9) 0.0611(3) 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'
O O 0.0106 0.0060 '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
O1 C1 O2 122.37(12) . . ?
O1 C1 C2 125.31(12) . . ?
O2 C1 C2 112.32(11) . . ?
C15 C2 C3 119.05(12) . . ?
C15 C2 C1 122.32(11) . . ?
C3 C2 C1 118.64(12) . . ?
C4 C3 C2 120.35(12) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 N2 122.37(11) . . ?
C3 C4 C13 120.79(11) . . ?
N2 C4 C13 116.78(11) . . ?
C6 C5 N2 107.58(13) . . ?
C6 C5 H5 126.2 . . ?
N2 C5 H5 126.2 . . ?
C5 C6 C7 108.35(13) . . ?
C5 C6 H6 125.8 . . ?
C7 C6 H6 125.8 . . ?
C8 C7 C6 107.54(13) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 N2 107.54(12) . . ?
C7 C8 C9 134.03(13) . . ?
N2 C8 C9 118.28(11) . . ?
N1 C9 C8 107.76(10) . . ?
N1 C9 C10 100.45(10) . . ?
C8 C9 C10 115.13(12) . . ?
N1 C9 C16 110.92(11) . . ?
C8 C9 C16 110.65(11) . . ?
C10 C9 C16 111.43(11) . . ?
C11 C10 C9 103.94(12) . . ?
C11 C10 H10A 111.0 . . ?
C9 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C10 C11 C12 105.88(11) . . ?
C10 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
N1 C12 C11 104.02(12) . . ?
N1 C12 H12A 111.0 . . ?
C11 C12 H12A 111.0 . . ?
N1 C12 H12B 111.0 . . ?
C11 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
N1 C13 C14 123.13(12) . . ?
N1 C13 C4 118.88(11) . . ?
C14 C13 C4 117.94(11) . . ?
C15 C14 C13 120.78(12) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C2 120.97(12) . . ?
C14 C15 H15 119.5 . . ?
C2 C15 H15 119.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N1 C12 124.35(11) . . ?
C13 N1 C9 120.73(10) . . ?
C12 N1 C9 111.40(10) . . ?
C5 N2 C8 108.99(11) . . ?
C5 N2 C4 128.13(11) . . ?
C8 N2 C4 122.57(11) . . ?
C1 O2 C17 116.35(12) . . ?
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 O1 1.2063(16) . ?
C1 O2 1.3421(16) . ?
C1 C2 1.4750(18) . ?
C2 C15 1.3906(18) . ?
C2 C3 1.3932(17) . ?
C3 C4 1.3786(17) . ?
C3 H3 0.9300 . ?
C4 N2 1.4152(15) . ?
C4 C13 1.4167(17) . ?
C5 C6 1.353(2) . ?
C5 N2 1.3746(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.360(2) . ?
C7 H7 0.9300 . ?
C8 N2 1.3824(16) . ?
C8 C9 1.4932(19) . ?
C9 N1 1.4669(16) . ?
C9 C10 1.5283(18) . ?
C9 C16 1.5362(19) . ?
C10 C11 1.521(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.526(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N1 1.4546(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N1 1.3653(16) . ?
C13 C14 1.3949(18) . ?
C14 C15 1.3787(18) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O2 1.4366(16) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O1 C1 C2 C15 174.53(13) . . . . ?
O2 C1 C2 C15 -5.99(18) . . . . ?
O1 C1 C2 C3 -5.6(2) . . . . ?
O2 C1 C2 C3 173.89(11) . . . . ?
C15 C2 C3 C4 2.43(19) . . . . ?
C1 C2 C3 C4 -177.46(11) . . . . ?
C2 C3 C4 N2 -176.64(11) . . . . ?
C2 C3 C4 C13 0.43(19) . . . . ?
N2 C5 C6 C7 -0.65(19) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 N2 0.45(19) . . . . ?
C6 C7 C8 C9 175.73(15) . . . . ?
C7 C8 C9 N1 150.43(17) . . . . ?
N2 C8 C9 N1 -34.68(16) . . . . ?
C7 C8 C9 C10 39.3(2) . . . . ?
N2 C8 C9 C10 -145.81(12) . . . . ?
C7 C8 C9 C16 -88.1(2) . . . . ?
N2 C8 C9 C16 86.75(14) . . . . ?
N1 C9 C10 C11 36.85(13) . . . . ?
C8 C9 C10 C11 152.26(12) . . . . ?
C16 C9 C10 C11 -80.69(14) . . . . ?
C9 C10 C11 C12 -27.89(16) . . . . ?
C10 C11 C12 N1 7.33(16) . . . . ?
C3 C4 C13 N1 179.39(11) . . . . ?
N2 C4 C13 N1 -3.38(17) . . . . ?
C3 C4 C13 C14 -3.11(19) . . . . ?
N2 C4 C13 C14 174.12(11) . . . . ?
N1 C13 C14 C15 -179.65(12) . . . . ?
C4 C13 C14 C15 3.0(2) . . . . ?
C13 C14 C15 C2 -0.2(2) . . . . ?
C3 C2 C15 C14 -2.6(2) . . . . ?
C1 C2 C15 C14 177.29(12) . . . . ?
C14 C13 N1 C12 -1.7(2) . . . . ?
C4 C13 N1 C12 175.64(13) . . . . ?
C14 C13 N1 C9 155.29(13) . . . . ?
C4 C13 N1 C9 -27.35(17) . . . . ?
C11 C12 N1 C13 176.36(12) . . . . ?
C11 C12 N1 C9 17.50(16) . . . . ?
C8 C9 N1 C13 44.99(16) . . . . ?
C10 C9 N1 C13 165.82(11) . . . . ?
C16 C9 N1 C13 -76.26(15) . . . . ?
C8 C9 N1 C12 -155.27(12) . . . . ?
C10 C9 N1 C12 -34.45(15) . . . . ?
C16 C9 N1 C12 83.47(14) . . . . ?
C6 C5 N2 C8 0.94(17) . . . . ?
C6 C5 N2 C4 174.61(13) . . . . ?
C7 C8 N2 C5 -0.87(16) . . . . ?
C9 C8 N2 C5 -177.02(12) . . . . ?
C7 C8 N2 C4 -174.96(12) . . . . ?
C9 C8 N2 C4 8.89(18) . . . . ?
C3 C4 N2 C5 16.5(2) . . . . ?
C13 C4 N2 C5 -160.68(13) . . . . ?
C3 C4 N2 C8 -170.60(12) . . . . ?
C13 C4 N2 C8 12.22(18) . . . . ?
O1 C1 O2 C17 1.2(2) . . . . ?
C2 C1 O2 C17 -178.33(11) . . . . ?
