#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:53:44 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180321 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/35/7153582.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_7153582
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            'C16 H13 N O'
_chemical_formula_weight         235.27
_chemical_melting_point          143.0(10)
_chemical_name_systematic
; 
 8-Acetyl-1-aza-7-phenylbicyclo[4.3.0]nona-2,4,6,8-tetraene 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 98.495(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.286(2)
_cell_length_b                   11.358(3)
_cell_length_c                   11.827(3)
_cell_measurement_reflns_used    3566
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      2.50
_cell_volume                     1233.7(5)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12115
_diffrn_reflns_theta_full        25.89
_diffrn_reflns_theta_max         25.89
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0453P)²+0.4428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                2103
_reflns_number_total             2380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42064g.txt
_cod_data_source_block           3h
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '142-144' was changed to '143.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' 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_cell_volume        1233.8(5)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7153582
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-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
N1 N 0.87616(16) 1.10778(13) 0.43955(12) 0.0406(4) Uani 1 1 d .
C5 C 0.77862(18) 1.01433(15) 0.44172(15) 0.0379(4) Uani 1 1 d .
O1 O 0.91885(17) 0.85808(14) 0.14538(13) 0.0658(5) Uani 1 1 d .
C6 C 0.79260(18) 0.94148(15) 0.35069(14) 0.0371(4) Uani 1 1 d .
C7 C 0.90214(19) 0.99226(15) 0.29340(15) 0.0390(4) Uani 1 1 d .
C11 C 0.69903(19) 0.83795(15) 0.32074(15) 0.0392(4) Uani 1 1 d .
C9 C 0.9632(2) 0.94725(17) 0.19528(16) 0.0460(5) Uani 1 1 d .
C3 C 0.6942(2) 1.10716(18) 0.60098(17) 0.0517(5) Uani 1 1 d .
H3 H 0.6323 1.1089 0.6560 0.062 Uiso 1 1 calc R
C8 C 0.9506(2) 1.09319(16) 0.35099(15) 0.0435(4) Uani 1 1 d .
H8 H 1.0227 1.1431 0.3320 0.052 Uiso 1 1 calc R
C12 C 0.6804(2) 0.75328(16) 0.40116(17) 0.0473(5) Uani 1 1 d .
H12 H 0.7331 0.7584 0.4742 0.057 Uiso 1 1 calc R
C4 C 0.6877(2) 1.01669(17) 0.52720(16) 0.0442(5) Uani 1 1 d .
H4 H 0.6229 0.9553 0.5326 0.053 Uiso 1 1 calc R
C16 C 0.6188(2) 0.82701(17) 0.21260(16) 0.0481(5) Uani 1 1 d .
H16 H 0.6300 0.8825 0.1568 0.058 Uiso 1 1 calc R
C1 C 0.8839(2) 1.19886(17) 0.51710(18) 0.0510(5) Uani 1 1 d .
H1 H 0.9509 1.2593 0.5148 0.061 Uiso 1 1 calc R
C2 C 0.7947(2) 1.19959(19) 0.59533(18) 0.0548(5) Uani 1 1 d .
H2 H 0.7985 1.2617 0.6469 0.066 Uiso 1 1 calc R
C14 C 0.5059(3) 0.6525(2) 0.2675(2) 0.0640(6) Uani 1 1 d .
H14 H 0.4410 0.5905 0.2499 0.077 Uiso 1 1 calc R
C13 C 0.5847(2) 0.66135(18) 0.3744(2) 0.0598(6) Uani 1 1 d .
H13 H 0.5736 0.6049 0.4294 0.072 Uiso 1 1 calc R
C15 C 0.5230(2) 0.7352(2) 0.18679(19) 0.0604(6) Uani 1 1 d .
H15 H 0.4696 0.7295 0.1140 0.072 Uiso 1 1 calc R
C10 C 1.0861(3) 1.0135(2) 0.15646(19) 0.0646(6) Uani 1 1 d .
H10A H 1.1327 0.9647 0.1063 0.097 Uiso 1 1 calc R
H10B H 1.1555 1.0350 0.2216 0.097 Uiso 1 1 calc R
H10C H 1.0492 1.0833 0.1165 0.097 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 128.88(17)
C8 N1 C5 109.20(15)
C1 N1 C5 121.88(16)
C6 C5 N1 107.77(15)
C6 C5 C4 134.96(17)
N1 C5 C4 117.19(16)
C5 C6 C7 106.53(15)
C5 C6 C11 123.11(16)
C7 C6 C11 130.21(16)
C8 C7 C6 107.84(16)
C8 C7 C9 123.33(17)
C6 C7 C9 128.75(16)
C12 C11 C16 117.89(17)
C12 C11 C6 121.28(16)
C16 C11 C6 120.68(16)
O1 C9 C7 122.40(18)
O1 C9 C10 119.38(18)
C7 C9 C10 118.22(18)
C4 C3 C2 120.28(19)
N1 C8 C7 108.65(16)
C13 C12 C11 120.77(19)
C3 C4 C5 120.41(18)
C15 C16 C11 120.9(2)
C2 C1 N1 119.43(19)
C1 C2 C3 120.79(18)
C15 C14 C13 119.6(2)
C14 C13 C12 120.5(2)
C14 C15 C16 120.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.348(2)
N1 C1 1.377(2)
N1 C5 1.398(2)
C5 C6 1.379(2)
C5 C4 1.410(3)
O1 C9 1.213(2)
C6 C7 1.425(2)
C6 C11 1.474(2)
C7 C8 1.375(2)
C7 C9 1.458(3)
C11 C12 1.381(3)
C11 C16 1.387(3)
C9 C10 1.495(3)
C3 C4 1.344(3)
C3 C2 1.412(3)
C12 C13 1.377(3)
C16 C15 1.375(3)
C1 C2 1.330(3)
C14 C15 1.365(3)
C14 C13 1.368(3)
