#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:59:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180326 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/40/7154035.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_7154035
loop_
_publ_author_name
'He, Haitao'
'Qi, Chaorong'
'Ou, Yanglu'
'Xiong, Wenfang'
'Hu, Xiaohan'
'Ren, Yanwei'
'Jiang, Huanfeng'
_publ_section_title
;
 Base-promoted annulation of α-hydroxy ketones and dimethyl
 but-2-ynedioate: straightforward access to
 pyrano[4,3-a]quinolizine-1,4,6(2H)-triones and 2H-pyran-2,5(6H)-diones.
;
_journal_issue                   41
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8128
_journal_page_last               8131
_journal_paper_doi               10.1039/c4ob01858c
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C14 H11 N O4'
_chemical_formula_weight         257.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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                 110.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3551(15)
_cell_length_b                   19.227(4)
_cell_length_c                   8.7515(18)
_cell_measurement_temperature    293(2)
_cell_volume                     1158.1(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10380
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.110
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0456
_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)+(0.0954P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                1904
_reflns_number_total             2606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01858c2.cif
_cod_data_source_block           qi-1
_cod_depositor_comments          'Adding full bibliography for 7154035.cif.'
_cod_original_cell_volume        1158.1(4)
_cod_database_code               7154035
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
O3 O 0.35018(16) 0.67746(5) 0.17495(16) 0.0504(3) Uani 1 1 d .
C1 C 0.4708(2) 0.55885(7) 0.20912(19) 0.0383(3) Uani 1 1 d .
C14 C 0.3317(2) 0.46671(7) 0.32230(18) 0.0359(3) Uani 1 1 d .
C2 C 0.3322(2) 0.53702(7) 0.27619(18) 0.0355(3) Uani 1 1 d .
O1 O 0.0945(2) 0.58034(6) 0.37858(17) 0.0597(4) Uani 1 1 d .
C3 C 0.1962(2) 0.58821(7) 0.29584(19) 0.0389(4) Uani 1 1 d .
C8 C 0.2012(2) 0.43796(8) 0.3908(2) 0.0425(4) Uani 1 1 d .
H8A H 0.1090 0.4665 0.4093 0.051 Uiso 1 1 calc R
C7 C 0.4835(2) 0.63281(8) 0.1644(2) 0.0457(4) Uani 1 1 d .
C4 C 0.1699(2) 0.65461(7) 0.1953(2) 0.0426(4) Uani 1 1 d .
N1 N 0.4652(2) 0.42164(6) 0.29549(17) 0.0402(3) Uani 1 1 d .
C13 C 0.6063(2) 0.51481(8) 0.1898(2) 0.0452(4) Uani 1 1 d .
H13A H 0.6983 0.5324 0.1495 0.054 Uiso 1 1 calc R
C10 C 0.3439(3) 0.32579(8) 0.4018(3) 0.0549(5) Uani 1 1 d .
H10A H 0.3492 0.2789 0.4292 0.066 Uiso 1 1 calc R
C12 C 0.6117(2) 0.44356(8) 0.2287(2) 0.0458(4) Uani 1 1 d .
O2 O 0.6153(2) 0.65462(6) 0.1268(2) 0.0703(5) Uani 1 1 d .
C11 C 0.4675(3) 0.35211(8) 0.3344(2) 0.0514(4) Uani 1 1 d .
H11A H 0.5564 0.3227 0.3135 0.062 Uiso 1 1 calc R
C5 C 0.1145(3) 0.71520(9) 0.2801(3) 0.0592(5) Uani 1 1 d .
H5A H 0.0992 0.7562 0.2142 0.089 Uiso 1 1 calc R
H5B H 0.2148 0.7228 0.3842 0.089 Uiso 1 1 calc R
H5C H -0.0055 0.7050 0.2957 0.089 Uiso 1 1 calc R
C9 C 0.2073(3) 0.36956(8) 0.4304(2) 0.0511(4) Uani 1 1 d .
H9A H 0.1209 0.3518 0.4765 0.061 Uiso 1 1 calc R
C6 C 0.0218(3) 0.64034(10) 0.0282(2) 0.0558(5) Uani 1 1 d .
H6A H 0.0025 0.6816 -0.0374 0.084 Uiso 1 1 calc R
H6B H -0.0990 0.6268 0.0386 0.084 Uiso 1 1 calc R
H6C H 0.0677 0.6035 -0.0229 0.084 Uiso 1 1 calc R
O4 O 0.7224(2) 0.40014(6) 0.21056(19) 0.0649(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 0.0033 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
C7 O3 C4 122.35(11)
C13 C1 C2 122.37(13)
C13 C1 C7 116.43(13)
C2 C1 C7 121.11(12)
N1 C14 C2 118.41(12)
N1 C14 C8 117.01(12)
C2 C14 C8 124.56(12)
C1 C2 C14 118.68(12)
C1 C2 C3 118.44(12)
C14 C2 C3 122.87(12)
O1 C3 C2 125.21(13)
O1 C3 C4 117.85(12)
C2 C3 C4 116.80(12)
C9 C8 C14 121.44(14)
O2 C7 O3 118.57(14)
O2 C7 C1 122.45(14)
O3 C7 C1 118.88(12)
O3 C4 C6 108.15(12)
O3 C4 C5 103.91(13)
C6 C4 C5 112.86(14)
O3 C4 C3 112.65(12)
C6 C4 C3 107.97(13)
C5 C4 C3 111.30(13)
C11 N1 C14 120.72(12)
C11 N1 C12 115.67(12)
C14 N1 C12 123.60(12)
C1 C13 C12 122.23(13)
C11 C10 C9 119.42(15)
O4 C12 C13 126.82(15)
O4 C12 N1 118.55(14)
C13 C12 N1 114.62(12)
C10 C11 N1 121.46(14)
C8 C9 C10 119.93(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C7 1.3306(19)
O3 C4 1.4661(17)
C1 C13 1.363(2)
C1 C2 1.4081(19)
C1 C7 1.486(2)
C14 N1 1.3902(17)
C14 C2 1.411(2)
C14 C8 1.412(2)
C2 C3 1.4559(18)
O1 C3 1.2203(17)
C3 C4 1.524(2)
C8 C9 1.357(2)
C7 O2 1.2040(18)
C4 C6 1.509(3)
C4 C5 1.512(2)
N1 C11 1.3782(19)
N1 C12 1.4573(19)
C13 C12 1.409(2)
C10 C11 1.345(2)
C10 C9 1.399(2)
C12 O4 1.2153(17)
