#------------------------------------------------------------------------------
#$Date: 2019-11-11 18:02:31 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/53/4035373.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_4035373
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            'C16 H10 N2 O'
_chemical_formula_weight         246.26
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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                 93.01(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8460(8)
_cell_length_b                   24.811(5)
_cell_length_c                   12.108(2)
_cell_measurement_reflns_used    2047
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.64
_cell_volume                     1153.8(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       dtprofit.ref
_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  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13368
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.0000
_exptl_absorpt_correction_T_min  0.0000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0593
_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)+(0.0500P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                1987
_reflns_number_total             2047
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01206_si_006.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'None' was changed
to 'none' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4035373
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
O1 O -0.2281(5) 0.67654(7) -0.03318(13) 0.0392(5) Uani 1 1 d .
C1 C 0.0051(6) 0.76008(9) 0.08764(19) 0.0287(5) Uani 1 1 d .
H1A H -0.1038 0.7654 0.0181 0.034 Uiso 1 1 calc R
C2 C 0.1045(6) 0.80314(10) 0.14884(19) 0.0291(5) Uani 1 1 d .
H2A H 0.0658 0.8378 0.1218 0.035 Uiso 1 1 calc R
C3 C 0.2679(6) 0.79514(10) 0.25432(19) 0.0291(5) Uani 1 1 d .
H3A H 0.3346 0.8246 0.2979 0.035 Uiso 1 1 calc R
C4 C 0.3279(6) 0.74441(9) 0.29215(19) 0.0268(5) Uani 1 1 d .
H4A H 0.4364 0.7395 0.3619 0.032 Uiso 1 1 calc R
C5 C 0.2288(6) 0.69862(9) 0.22771(17) 0.0227(5) Uani 1 1 d .
C6 C 0.2902(6) 0.64514(9) 0.26195(17) 0.0225(5) Uani 1 1 d .
C7 C 0.1855(6) 0.60137(9) 0.19328(17) 0.0238(5) Uani 1 1 d .
C8 C 0.0180(6) 0.61210(9) 0.09196(18) 0.0273(5) Uani 1 1 d .
H8A H -0.0451 0.5831 0.0467 0.033 Uiso 1 1 calc R
C9 C -0.0633(6) 0.66452(10) 0.05290(18) 0.0271(5) Uani 1 1 d .
C10 C 0.4776(6) 0.63801(9) 0.36638(18) 0.0244(5) Uani 1 1 d .
C11 C 0.2493(6) 0.54456(9) 0.22825(18) 0.0246(5) Uani 1 1 d .
C12 C 0.1892(6) 0.52742(9) 0.33507(19) 0.0282(5) Uani 1 1 d .
H12A H 0.1085 0.5517 0.3863 0.034 Uiso 1 1 calc R
C13 C 0.2493(7) 0.47424(10) 0.3653(2) 0.0323(6) Uani 1 1 d .
H13A H 0.2088 0.4630 0.4368 0.039 Uiso 1 1 calc R
C14 C 0.3691(7) 0.43789(10) 0.2897(2) 0.0331(6) Uani 1 1 d .
H14A H 0.4105 0.4023 0.3106 0.040 Uiso 1 1 calc R
C15 C 0.4276(7) 0.45428(10) 0.1835(2) 0.0348(6) Uani 1 1 d .
H15A H 0.5079 0.4297 0.1327 0.042 Uiso 1 1 calc R
C16 C 0.3667(6) 0.50714(10) 0.1526(2) 0.0309(6) Uani 1 1 d .
H16A H 0.4043 0.5179 0.0806 0.037 Uiso 1 1 calc R
N1 N 0.0608(5) 0.70791(8) 0.12544(14) 0.0240(4) Uani 1 1 d .
N2 N 0.6314(6) 0.63403(8) 0.45016(16) 0.0333(5) 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
C2 C1 N1 121.7(2)
C2 C1 H1A 119.1
N1 C1 H1A 119.1
C1 C2 C3 119.3(2)
C1 C2 H2A 120.4
C3 C2 H2A 120.4
C4 C3 C2 119.8(2)
C4 C3 H3A 120.1
C2 C3 H3A 120.1
C3 C4 C5 121.5(2)
C3 C4 H4A 119.3
C5 C4 H4A 119.3
N1 C5 C6 118.9(2)
N1 C5 C4 117.2(2)
C6 C5 C4 123.9(2)
C5 C6 C7 120.9(2)
C5 C6 C10 116.46(19)
C7 C6 C10 122.6(2)
C8 C7 C6 118.7(2)
C8 C7 C11 119.8(2)
C6 C7 C11 121.51(19)
C7 C8 C9 124.0(2)
C7 C8 H8A 118.0
C9 C8 H8A 118.0
O1 C9 C8 127.1(2)
O1 C9 N1 118.1(2)
C8 C9 N1 114.80(19)
N2 C10 C6 177.7(2)
C12 C11 C16 118.8(2)
C12 C11 C7 121.4(2)
C16 C11 C7 119.8(2)
C13 C12 C11 120.2(2)
C13 C12 H12A 119.9
C11 C12 H12A 119.9
C14 C13 C12 120.2(2)
C14 C13 H13A 119.9
C12 C13 H13A 119.9
C15 C14 C13 120.1(2)
C15 C14 H14A 119.9
C13 C14 H14A 119.9
C14 C15 C16 120.0(2)
C14 C15 H15A 120.0
C16 C15 H15A 120.0
C15 C16 C11 120.7(2)
C15 C16 H16A 119.7
C11 C16 H16A 119.7
C5 N1 C1 120.48(19)
C5 N1 C9 122.64(19)
C1 N1 C9 116.88(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.228(3)
C1 C2 1.344(3)
C1 N1 1.386(3)
C1 H1A 0.9300
C2 C3 1.407(3)
C2 H2A 0.9300
C3 C4 1.355(3)
C3 H3A 0.9300
C4 C5 1.419(3)
C4 H4A 0.9300
C5 N1 1.386(3)
C5 C6 1.406(3)
C6 C7 1.413(3)
C6 C10 1.433(3)
C7 C8 1.381(3)
C7 C11 1.488(3)
C8 C9 1.413(3)
C8 H8A 0.9300
C9 N1 1.454(3)
C10 N2 1.151(3)
C11 C12 1.392(3)
C11 C16 1.396(3)
C12 C13 1.385(3)
C12 H12A 0.9300
C13 C14 1.381(3)
C13 H13A 0.9300
C14 C15 1.379(3)
C14 H14A 0.9300
C15 C16 1.380(3)
C15 H15A 0.9300
C16 H16A 0.9300
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
N1 C1 C2 C3 -0.3(4)
C1 C2 C3 C4 1.0(4)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 N1 -1.4(3)
C3 C4 C5 C6 178.8(2)
N1 C5 C6 C7 0.5(3)
C4 C5 C6 C7 -179.8(2)
N1 C5 C6 C10 177.49(19)
C4 C5 C6 C10 -2.7(3)
C5 C6 C7 C8 -0.6(3)
C10 C6 C7 C8 -177.4(2)
C5 C6 C7 C11 179.9(2)
C10 C6 C7 C11 3.0(3)
C6 C7 C8 C9 -1.4(4)
C11 C7 C8 C9 178.1(2)
C7 C8 C9 O1 -175.6(2)
C7 C8 C9 N1 3.3(3)
C5 C6 C10 N2 -15(6)
C7 C6 C10 N2 162(6)
C8 C7 C11 C12 -136.0(2)
C6 C7 C11 C12 43.5(3)
C8 C7 C11 C16 43.0(3)
C6 C7 C11 C16 -137.5(2)
C16 C11 C12 C13 0.7(4)
C7 C11 C12 C13 179.7(2)
C11 C12 C13 C14 0.0(4)
C12 C13 C14 C15 -0.4(4)
C13 C14 C15 C16 0.1(4)
C14 C15 C16 C11 0.6(4)
C12 C11 C16 C15 -1.0(4)
C7 C11 C16 C15 180.0(2)
C6 C5 N1 C1 -178.1(2)
C4 C5 N1 C1 2.1(3)
C6 C5 N1 C9 1.6(3)
C4 C5 N1 C9 -178.1(2)
C2 C1 N1 C5 -1.3(3)
C2 C1 N1 C9 178.9(2)
O1 C9 N1 C5 175.6(2)
C8 C9 N1 C5 -3.4(3)
O1 C9 N1 C1 -4.6(3)
C8 C9 N1 C1 176.3(2)
