#------------------------------------------------------------------------------
#$Date: 2019-11-11 18:02:16 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226829 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/53/4035372.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_4035372
loop_
_publ_author_name
'Dong, Chao-Chen'
'Xiang, Jun-Feng'
'Xu, Li-Jin'
'Gong, Han-Yuan'
_publ_section_title
;
 From CO₂ to 4 H-Quinolizin-4-ones: A One-Pot Multicomponent
 Approach via Ag₂O/Cs₂CO₃ Orthogonal
 Tandem Catalysis.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9561
_journal_page_last               9567
_journal_paper_doi               10.1021/acs.joc.8b01206
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.858(2)
_cell_length_b                   6.8927(10)
_cell_length_c                   9.0764(12)
_cell_measurement_reflns_used    836
_cell_measurement_temperature    99.99(18)
_cell_measurement_theta_max      64.948
_cell_measurement_theta_min      5.580
_cell_volume                     992.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_diffrn_ambient_temperature      99.99(18)
_diffrn_detector_area_resol_mean 5.3127
_diffrn_measured_fraction_theta_full 0.857
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.857
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1810
_diffrn_reflns_point_group_measured_fraction_full 0.857
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         64.948
_diffrn_reflns_theta_min         5.580
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32600
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         836
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0731P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.000
_reflns_number_gt                627
_reflns_number_total             836
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b01206_si_003.cif
_cod_data_source_block           A
_cod_database_code               4035372
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.30750(14) 0.7500 0.3260(3) 0.0286(6) Uani 1 2 d S T P
C1 C 0.4668(2) 0.7500 0.2420(4) 0.0251(8) Uani 1 2 d S T P
H1A H 0.4233 0.7500 0.1732 0.030 Uiso 1 2 calc R U P
C2 C 0.5477(2) 0.7500 0.1944(4) 0.0273(8) Uani 1 2 d S T P
H2A H 0.5595 0.7500 0.0941 0.033 Uiso 1 2 calc R U P
C3 C 0.6141(2) 0.7500 0.2985(4) 0.0258(8) Uani 1 2 d S T P
H3A H 0.6699 0.7500 0.2669 0.031 Uiso 1 2 calc R U P
C4 C 0.59598(19) 0.7500 0.4445(4) 0.0219(7) Uani 1 2 d S T P
H4A H 0.6397 0.7500 0.5128 0.026 Uiso 1 2 calc R U P
C5 C 0.51049(19) 0.7500 0.4949(3) 0.0190(7) Uani 1 2 d S T P
C6 C 0.4879(2) 0.7500 0.6439(3) 0.0210(7) Uani 1 2 d S T P
C7 C 0.4021(2) 0.7500 0.6880(4) 0.0227(8) Uani 1 2 d S T P
C8 C 0.3404(2) 0.7500 0.5795(4) 0.0249(8) Uani 1 2 d S T P
H8A H 0.2842 0.7500 0.6088 0.030 Uiso 1 2 calc R U P
C9 C 0.3581(2) 0.7500 0.4282(4) 0.0229(8) Uani 1 2 d S T P
C10 C 0.5552(2) 0.7500 0.7489(4) 0.0231(8) Uani 1 2 d S T P
C11 C 0.3816(2) 0.7500 0.8469(4) 0.0268(8) Uani 1 2 d S T P
H11A H 0.4306 0.7500 0.9127 0.032 Uiso 1 2 calc R U P
C12 C 0.30497(14) 0.8579(4) 0.9053(3) 0.0292(6) Uani 1 1 d . . .
H12A H 0.3103 0.9233 0.9995 0.035 Uiso 1 1 calc R U .
H12B H 0.2691 0.9233 0.8345 0.035 Uiso 1 1 calc R U .
N1 N 0.44760(17) 0.7500 0.3897(3) 0.0204(6) Uani 1 2 d S T P
N2 N 0.61071(18) 0.7500 0.8305(3) 0.0324(8) Uani 1 2 d S T P
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 N1 121.4(3) . .
C2 C1 H1A 119.3 . .
N1 C1 H1A 119.3 . .
C1 C2 C3 119.5(3) . .
C1 C2 H2A 120.2 . .
C3 C2 H2A 120.2 . .
C4 C3 C2 119.7(3) . .
C4 C3 H3A 120.2 . .
C2 C3 H3A 120.2 . .
C3 C4 C5 120.9(3) . .
C3 C4 H4A 119.6 . .
C5 C4 H4A 119.6 . .
N1 C5 C6 118.9(3) . .
N1 C5 C4 117.6(3) . .
C6 C5 C4 123.5(3) . .
C5 C6 C7 121.2(3) . .
C5 C6 C10 116.9(3) . .
C7 C6 C10 121.8(3) . .
C8 C7 C6 118.4(3) . .
C8 C7 C11 122.5(3) . .
C6 C7 C11 119.1(3) . .
C7 C8 C9 123.6(3) . .
C7 C8 H8A 118.2 . .
C9 C8 H8A 118.2 . .
O1 C9 C8 127.6(3) . .
O1 C9 N1 117.0(3) . .
C8 C9 N1 115.4(3) . .
N2 C10 C6 178.4(4) . .
C7 C11 C12 121.0(2) . 7_575
C7 C11 C12 121.0(2) . .
C12 C11 C12 58.6(2) 7_575 .
C7 C11 H11A 114.9 . .
C12 C11 H11A 114.9 7_575 .
C12 C11 H11A 114.9 . .
C12 C12 C11 60.72(11) 7_575 .
C12 C12 H12A 117.7 7_575 .
C11 C12 H12A 117.7 . .
C12 C12 H12B 117.7 7_575 .
C11 C12 H12B 117.7 . .
H12A C12 H12B 114.8 . .
C1 N1 C5 120.9(3) . .
C1 N1 C9 116.6(3) . .
C5 N1 C9 122.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.226(4) .
C1 C2 1.353(5) .
C1 N1 1.376(4) .
C1 H1A 0.9300 .
C2 C3 1.414(5) .
C2 H2A 0.9300 .
C3 C4 1.356(5) .
C3 H3A 0.9300 .
C4 C5 1.431(4) .
C4 H4A 0.9300 .
C5 N1 1.380(4) .
C5 C6 1.399(4) .
C6 C7 1.419(4) .
C6 C10 1.431(4) .
C7 C8 1.388(5) .
C7 C11 1.478(5) .
C8 C9 1.402(5) .
C8 H8A 0.9300 .
C9 N1 1.462(4) .
C10 N2 1.150(4) .
C11 C12 1.520(4) 7_575
C11 C12 1.520(4) .
C11 H11A 0.9800 .
C12 C12 1.487(5) 7_575
C12 H12A 0.9700 .
C12 H12B 0.9700 .
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_4
N1 C1 C2 C3 0.000(0) .
C1 C2 C3 C4 0.000(0) .
C2 C3 C4 C5 0.000(0) .
C3 C4 C5 N1 0.000(0) .
C3 C4 C5 C6 180.000(0) .
N1 C5 C6 C7 0.000(1) .
C4 C5 C6 C7 180.000(0) .
N1 C5 C6 C10 180.000(0) .
C4 C5 C6 C10 0.000(1) .
C5 C6 C7 C8 0.000(1) .
C10 C6 C7 C8 180.000(0) .
C5 C6 C7 C11 180.000(1) .
C10 C6 C7 C11 0.000(1) .
C6 C7 C8 C9 0.000(1) .
C11 C7 C8 C9 180.000(1) .
C7 C8 C9 O1 180.000(0) .
C7 C8 C9 N1 0.000(1) .
C8 C7 C11 C12 34.81(18) 7_575
C6 C7 C11 C12 -145.19(18) 7_575
C8 C7 C11 C12 -34.81(18) .
C6 C7 C11 C12 145.19(18) .
C7 C11 C12 C12 109.7(2) 7_575
C2 C1 N1 C5 0.000(0) .
C2 C1 N1 C9 180.000(0) .
C6 C5 N1 C1 180.000(0) .
C4 C5 N1 C1 0.000(0) .
C6 C5 N1 C9 0.000(0) .
C4 C5 N1 C9 180.000(0) .
O1 C9 N1 C1 0.000(0) .
C8 C9 N1 C1 180.000(0) .
O1 C9 N1 C5 180.000(0) .
C8 C9 N1 C5 0.000(0) .
