#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:53:44 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180321 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/35/7153583.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_7153583
loop_
_publ_author_name
'Basavaiah, Deevi'
'Veeraraghavaiah, Gorre'
'Badsara, Satpal Singh'
_publ_section_title
;
 Ketones as electrophiles in two component Baylis-Hillman reaction: a
 facile one-pot synthesis of substituted indolizines.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1551
_journal_page_last               1555
_journal_paper_doi               10.1039/c3ob42064g
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.36
_chemical_melting_point          122.5(5)
_chemical_name_systematic
; 
 8-Acetyl-1-aza-9-(3-oxobutyl)-7-phenylbicyclo[4.3.0]nona-2,4,6,8-tetraene 
;
_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                81.098(2)
_cell_angle_beta                 65.775(2)
_cell_angle_gamma                79.753(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1844(10)
_cell_length_b                   9.6681(11)
_cell_length_c                   10.4799(12)
_cell_measurement_reflns_used    3146
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.45
_cell_volume                     831.62(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8707
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.264
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.264
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0887
_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)+(0.0582P)²+0.5349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1860
_refine_ls_wR_factor_ref         0.1889
_reflns_number_gt                3107
_reflns_number_total             3258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42064g.txt
_cod_data_source_block           4h
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '122-123' was changed to '122.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7153583
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
N1 N 0.4120(2) 0.1773(2) 0.6606(2) 0.0406(5) Uani 1 1 d .
O2 O -0.1440(2) 0.0294(2) 0.9348(2) 0.0574(6) Uani 1 1 d .
C13 C -0.0482(3) -0.0443(3) 0.8477(3) 0.0423(6) Uani 1 1 d .
C15 C 0.5773(3) 0.3482(3) 0.3018(3) 0.0402(6) Uani 1 1 d .
O1 O 0.0760(3) 0.2537(3) 0.4749(3) 0.0728(7) Uani 1 1 d .
C7 C 0.3139(3) 0.2662(3) 0.5003(3) 0.0406(6) Uani 1 1 d .
C8 C 0.2761(3) 0.1985(3) 0.6343(3) 0.0400(6) Uani 1 1 d .
C5 C 0.5384(3) 0.2319(3) 0.5441(3) 0.0403(6) Uani 1 1 d .
C12 C 0.1025(3) 0.0047(3) 0.7372(3) 0.0462(7) Uani 1 1 d .
H12A H 0.1048 -0.0055 0.6457 0.055 Uiso 1 1 calc R
H12B H 0.1940 -0.0562 0.7471 0.055 Uiso 1 1 calc R
C11 C 0.1207(3) 0.1559(3) 0.7421(3) 0.0422(6) Uani 1 1 d .
H11A H 0.0324 0.2177 0.7272 0.051 Uiso 1 1 calc R
H11B H 0.1141 0.1676 0.8346 0.051 Uiso 1 1 calc R
C4 C 0.6892(3) 0.2195(3) 0.5528(3) 0.0484(7) Uani 1 1 d .
H4 H 0.7757 0.2534 0.4769 0.058 Uiso 1 1 calc R
C6 C 0.4786(3) 0.2878(3) 0.4433(3) 0.0396(6) Uani 1 1 d .
C16 C 0.6652(4) 0.4572(3) 0.2846(3) 0.0517(7) Uani 1 1 d .
H16 H 0.6604 0.4942 0.3633 0.062 Uiso 1 1 calc R
C1 C 0.4349(4) 0.1143(3) 0.7797(3) 0.0513(7) Uani 1 1 d .
H1 H 0.3502 0.0782 0.8559 0.062 Uiso 1 1 calc R
C20 C 0.5874(4) 0.2960(3) 0.1824(3) 0.0543(8) Uani 1 1 d .
H20 H 0.5301 0.2225 0.1910 0.065 Uiso 1 1 calc R
C9 C 0.1920(3) 0.3152(3) 0.4408(3) 0.0492(7) Uani 1 1 d .
C18 C 0.7677(5) 0.4592(4) 0.0360(3) 0.0716(10) Uani 1 1 d .
H18 H 0.8313 0.4966 -0.0529 0.086 Uiso 1 1 calc R
C2 C 0.5786(4) 0.1055(4) 0.7851(3) 0.0622(9) Uani 1 1 d .
H2 H 0.5935 0.0636 0.8657 0.075 Uiso 1 1 calc R
C17 C 0.7596(4) 0.5112(4) 0.1528(4) 0.0658(9) Uani 1 1 d .
H17 H 0.8185 0.5838 0.1431 0.079 Uiso 1 1 calc R
C19 C 0.6819(5) 0.3519(4) 0.0503(3) 0.0701(10) Uani 1 1 d .
H19 H 0.6871 0.3162 -0.0292 0.084 Uiso 1 1 calc R
C3 C 0.7091(4) 0.1592(4) 0.6697(4) 0.0613(9) Uani 1 1 d .
H3 H 0.8088 0.1527 0.6749 0.074 Uiso 1 1 calc R
C14 C -0.0737(5) -0.1910(4) 0.8438(4) 0.0760(11) Uani 1 1 d .
H14A H -0.1758 -0.2103 0.9159 0.114 Uiso 1 1 calc R
H14B H 0.0107 -0.2562 0.8592 0.114 Uiso 1 1 calc R
H14C H -0.0725 -0.2012 0.7537 0.114 Uiso 1 1 calc R
C10 C 0.2068(4) 0.4477(4) 0.3437(4) 0.0715(10) Uani 1 1 d .
H10A H 0.1082 0.4767 0.3302 0.107 Uiso 1 1 calc R
H10B H 0.2935 0.4306 0.2548 0.107 Uiso 1 1 calc R
H10C H 0.2282 0.5207 0.3837 0.107 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'
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
C8 N1 C1 129.2(2)
C8 N1 C5 109.8(2)
C1 N1 C5 121.1(2)
O2 C13 C14 121.4(3)
O2 C13 C12 122.5(3)
C14 C13 C12 116.2(3)
C20 C15 C16 117.9(3)
C20 C15 C6 121.1(2)
C16 C15 C6 121.0(2)
C8 C7 C6 108.5(2)
C8 C7 C9 122.3(2)
C6 C7 C9 128.9(2)
N1 C8 C7 107.4(2)
N1 C8 C11 121.5(2)
C7 C8 C11 131.0(2)
C6 C5 N1 107.5(2)
C6 C5 C4 134.9(2)
N1 C5 C4 117.7(2)
C13 C12 C11 114.4(2)
C8 C11 C12 112.6(2)
C3 C4 C5 120.5(3)
C5 C6 C7 106.8(2)
C5 C6 C15 123.9(2)
C7 C6 C15 129.1(2)
C17 C16 C15 120.8(3)
C2 C1 N1 119.8(3)
C19 C20 C15 120.7(3)
O1 C9 C7 120.7(3)
O1 C9 C10 119.7(3)
C7 C9 C10 119.5(3)
C17 C18 C19 119.7(3)
C1 C2 C3 120.8(3)
C18 C17 C16 120.6(3)
C18 C19 C20 120.3(3)
C4 C3 C2 120.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.359(3)
N1 C1 1.381(3)
N1 C5 1.404(3)
O2 C13 1.198(3)
C13 C14 1.487(4)
C13 C12 1.493(4)
C15 C20 1.383(4)
C15 C16 1.385(4)
C15 C6 1.476(3)
O1 C9 1.210(4)
C7 C8 1.385(4)
C7 C6 1.421(4)
C7 C9 1.469(4)
C8 C11 1.492(3)
C5 C6 1.380(4)
C5 C4 1.409(4)
C12 C11 1.511(4)
C4 C3 1.340(4)
C16 C17 1.374(4)
C1 C2 1.332(4)
C20 C19 1.382(4)
C9 C10 1.496(4)
C18 C17 1.363(5)
C18 C19 1.366(5)
C2 C3 1.417(4)
