#------------------------------------------------------------------------------
#$Date: 2017-12-11 01:28:22 +0200 (Mon, 11 Dec 2017) $
#$Revision: 204147 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/21/7152139.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_7152139
loop_
_publ_author_name
'Hardin Narayan, Alison R.'
'Sarpong, Richmond'
_publ_section_title
;
 Indolizinones as synthetic scaffolds: fundamental reactivity and the
 relay of stereochemical information.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              70
_journal_page_last               78
_journal_paper_doi               10.1039/c1ob06423a
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_chemical_name_common            sarpong18
_chemical_name_systematic
;
sarpong18
;
_space_group.centring_type       C
_space_group_IT_number           15
_space_group.IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 110.568(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.2396(13)
_cell_length_b                   12.8939(7)
_cell_length_c                   10.3090(6)
_cell_measurement_reflns_used    4679
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.34
_cell_measurement_theta_min      4.03
_cell_volume                     2767.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-97
_computing_structure_solution    SIR-2008
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'HELIOS multilayer mirrors'
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0106
_diffrn_refln_scan_rate          5
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2466
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_min         4.03
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  0.9524
_exptl_absorpt_correction_T_min  0.9080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   TWINABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.113
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0465
_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)+(0.0719P)²+3.1407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                2362
_reflns_number_total             2466
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06423a.txt
_cod_data_source_block           sarpong18
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_space_group.centring_type' value 'C-centered' was replaced with the
value 'C' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7152139
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.47681(9) 0.22610(14) 0.4584(2) 0.0202(4) Uani 1 1 d .
H1 H 0.5107 0.2498 0.4300 0.024 Uiso 1 1 calc R
C2 C 0.48592(8) 0.15518(14) 0.5592(2) 0.0210(4) Uani 1 1 d .
H2 H 0.5259 0.1265 0.6155 0.025 Uiso 1 1 calc R
C3 C 0.42392(9) 0.13071(13) 0.56614(19) 0.0180(4) Uani 1 1 d .
C4 C 0.37503(8) 0.20459(14) 0.4654(2) 0.0177(4) Uani 1 1 d .
C5 C 0.31945(8) 0.15165(14) 0.3488(2) 0.0188(4) Uani 1 1 d .
H5 H 0.2911 0.1111 0.3870 0.023 Uiso 1 1 calc R
C6 C 0.34948(8) 0.08127(14) 0.2654(2) 0.0184(4) Uani 1 1 d .
H6 H 0.3770 0.0264 0.3264 0.022 Uiso 1 1 calc R
C7 C 0.29800(9) 0.03324(14) 0.1427(2) 0.0219(4) Uani 1 1 d .
C8 C 0.35563(9) 0.13423(14) 0.0459(2) 0.0209(4) Uani 1 1 d .
C9 C 0.38874(8) 0.14761(14) 0.2001(2) 0.0185(4) Uani 1 1 d .
H9 H 0.4340 0.1219 0.2295 0.022 Uiso 1 1 calc R
C10 C 0.38729(9) 0.26232(14) 0.2456(2) 0.0201(4) Uani 1 1 d .
H10 H 0.4122 0.3085 0.2051 0.024 Uiso 1 1 calc R
C11 C 0.31782(9) 0.29483(14) 0.2012(2) 0.0218(4) Uani 1 1 d .
H11 H 0.3009 0.3520 0.1414 0.026 Uiso 1 1 calc R
C12 C 0.28252(8) 0.23678(14) 0.2527(2) 0.0212(4) Uani 1 1 d .
H12 H 0.2378 0.2476 0.2312 0.025 Uiso 1 1 calc R
C13 C 0.34909(9) 0.27711(15) 0.5523(2) 0.0215(4) Uani 1 1 d .
H13A H 0.3163 0.3234 0.4888 0.026 Uiso 1 1 calc R
H13B H 0.3275 0.2345 0.6029 0.026 Uiso 1 1 calc R
C14 C 0.40037(9) 0.34399(15) 0.6571(2) 0.0243(5) Uani 1 1 d .
H14A H 0.4290 0.2990 0.7309 0.029 Uiso 1 1 calc R
H14B H 0.4268 0.3786 0.6099 0.029 Uiso 1 1 calc R
C15 C 0.37086(10) 0.42435(16) 0.7208(2) 0.0303(5) Uani 1 1 d .
H15 H 0.3376 0.4654 0.6591 0.036 Uiso 1 1 calc R
C16 C 0.38642(13) 0.4436(2) 0.8532(3) 0.0436(6) Uani 1 1 d .
H16A H 0.4194 0.4046 0.9191 0.052 Uiso 1 1 calc R
H16B H 0.3647 0.4965 0.8835 0.052 Uiso 1 1 calc R
N1 N 0.41474(7) 0.26192(12) 0.39915(17) 0.0183(4) Uani 1 1 d .
O1 O 0.40961(6) 0.06840(10) 0.64048(14) 0.0228(3) Uani 1 1 d .
O2 O 0.25668(7) -0.02591(11) 0.13922(16) 0.0311(4) Uani 1 1 d .
O3 O 0.30250(6) 0.07097(10) 0.01920(14) 0.0220(3) Uani 1 1 d .
O4 O 0.36922(6) 0.17105(12) -0.04585(15) 0.0282(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 N1 115.18(17)
C2 C1 H1 122.4
N1 C1 H1 122.4
C1 C2 C3 107.48(16)
C1 C2 H2 126.3
C3 C2 H2 126.3
O1 C3 C2 129.59(17)
O1 C3 C4 123.31(16)
C2 C3 C4 106.99(15)
N1 C4 C13 111.66(15)
N1 C4 C3 102.96(14)
C13 C4 C3 107.66(15)
N1 C4 C5 107.63(15)
C13 C4 C5 111.07(14)
C3 C4 C5 115.64(14)
C12 C5 C4 106.88(15)
C12 C5 C6 107.56(15)
C4 C5 C6 107.84(14)
C12 C5 H5 111.4
C4 C5 H5 111.4
C6 C5 H5 111.4
C7 C6 C9 103.98(15)
C7 C6 C5 110.90(14)
C9 C6 C5 109.78(15)
C7 C6 H6 110.7
C9 C6 H6 110.7
C5 C6 H6 110.7
O2 C7 O3 119.94(18)
O2 C7 C6 129.9(2)
O3 C7 C6 110.15(16)
O4 C8 O3 121.05(18)
O4 C8 C9 128.78(17)
O3 C8 C9 110.16(16)
C8 C9 C6 104.82(15)
C8 C9 C10 111.87(15)
C6 C9 C10 108.78(15)
C8 C9 H9 110.4
C6 C9 H9 110.4
C10 C9 H9 110.4
N1 C10 C11 108.59(16)
N1 C10 C9 105.92(15)
C11 C10 C9 107.47(15)
N1 C10 H10 111.5
C11 C10 H10 111.5
C9 C10 H10 111.5
C12 C11 C10 114.17(17)
C12 C11 H11 122.9
C10 C11 H11 122.9
C11 C12 C5 114.27(16)
C11 C12 H12 122.9
C5 C12 H12 122.9
C14 C13 C4 114.43(15)
C14 C13 H13A 108.7
C4 C13 H13A 108.7
C14 C13 H13B 108.7
C4 C13 H13B 108.7
H13A C13 H13B 107.6
C15 C14 C13 111.50(16)
C15 C14 H14A 109.3
C13 C14 H14A 109.3
C15 C14 H14B 109.3
C13 C14 H14B 109.3
H14A C14 H14B 108.0
C16 C15 C14 126.4(2)
C16 C15 H15 116.8
C14 C15 H15 116.8
C15 C16 H16A 120.0
C15 C16 H16B 120.0
H16A C16 H16B 120.0
C1 N1 C10 116.53(16)
C1 N1 C4 107.08(14)
C10 N1 C4 113.79(14)
C8 O3 C7 110.69(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.345(3)
C1 N1 1.378(2)
C1 H1 0.9500
C2 C3 1.440(3)
C2 H2 0.9500
C3 O1 1.227(2)
C3 C4 1.541(2)
C4 N1 1.489(2)
C4 C13 1.540(3)
C4 C5 1.548(2)
C5 C12 1.513(3)
C5 C6 1.553(3)
C5 H5 1.0000
C6 C7 1.509(3)
C6 C9 1.536(3)
C6 H6 1.0000
C7 O2 1.185(2)
C7 O3 1.399(3)
C8 O4 1.189(3)
C8 O3 1.381(2)
C8 C9 1.508(3)
C9 C10 1.556(3)
C9 H9 1.0000
C10 N1 1.483(3)
C10 C11 1.508(3)
C10 H10 1.0000
C11 C12 1.323(3)
C11 H11 0.9500
C12 H12 0.9500
C13 C14 1.531(3)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.496(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.309(3)
C15 H15 0.9500
C16 H16A 0.9500
C16 H16B 0.9500
