#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/53/4025393.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_4025393
loop_
_publ_author_name
'Haitao Yu'
'Jinbo Li'
'Zhuangfei Kou'
'Xuewen Du'
'Yi wei'
'Hoong-Kun Fun'
'Jianhua Xu'
'Yan Zhang'
_publ_section_title
;
 Photoinduced Tandem Reactions of Isoquinoline-1,3,4-trione with Alkynes
 To Build Aza-polycycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2989
_journal_page_last               3001
_journal_paper_doi               10.1021/jo100218w
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C21 H12 N4 O3, C H3 O H'
_chemical_formula_sum            'C22 H16 N4 O4'
_chemical_formula_weight         400.39
_chemical_name_systematic
; 
 ? 
;
_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                 106.52(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5310(17)
_cell_length_b                   26.709(5)
_cell_length_c                   8.8690(18)
_cell_measurement_reflns_used    3527
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      1.52
_cell_volume                     1937.4(7)
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_collection       'CAD4 EXPRESS(Enraf-Nonius,1994)'
_computing_data_reduction        'XCAD4(Harms & Wocadlo,1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3527
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.52
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.345
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.427
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.439
_refine_ls_R_factor_all          0.1902
_refine_ls_R_factor_gt           0.1211
_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)+(0.0700P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2616
_refine_ls_wR_factor_ref         0.2912
_reflns_number_gt                1751
_reflns_number_total             3527
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100218w_si_002.cif
_cod_data_source_block           y
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025393
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0990(5) -0.15179(17) 0.0538(5) 0.0532(12) Uani 1 1 d . . .
N1 N 0.6168(6) 0.0212(2) 0.3651(5) 0.0454(14) Uani 1 1 d . . .
C1 C 0.5658(8) 0.0601(3) 0.2659(8) 0.0515(17) Uani 1 1 d . . .
H1B H 0.6243 0.0896 0.2945 0.062 Uiso 1 1 calc R . .
O2 O -0.2079(5) -0.07644(18) -0.3893(5) 0.0635(14) Uani 1 1 d . . .
N2 N 0.4468(6) 0.06222(19) 0.1362(6) 0.0425(13) Uani 1 1 d . . .
C2 C 0.5327(7) -0.0200(2) 0.3238(6) 0.0385(15) Uani 1 1 d . . .
H2B H 0.5617 -0.0481 0.3880 0.046 Uiso 1 1 calc R . .
O3 O 0.3207(5) -0.11427(18) 0.3749(5) 0.0576(13) Uani 1 1 d . . .
N3 N -0.0565(6) -0.11350(19) -0.1669(6) 0.0440(13) Uani 1 1 d . . .
C3 C 0.3986(6) -0.0240(2) 0.1852(6) 0.0326(13) Uani 1 1 d . . .
C4 C 0.3611(6) 0.0191(2) 0.0935(6) 0.0304(13) Uani 1 1 d . . .
N4 N 0.6941(10) -0.2068(3) 0.3198(11) 0.108(3) Uani 1 1 d . . .
C5 C 0.3058(6) -0.0693(2) 0.1426(6) 0.0347(14) Uani 1 1 d . . .
C6 C 0.1750(6) -0.0694(2) 0.0097(6) 0.0326(13) Uani 1 1 d . . .
C7 C 0.1363(6) -0.0266(2) -0.0872(6) 0.0314(13) Uani 1 1 d . . .
C8 C 0.2260(6) 0.0178(2) -0.0498(6) 0.0304(13) Uani 1 1 d . . .
C9 C 0.0743(7) -0.1151(2) -0.0290(7) 0.0410(15) Uani 1 1 d . . .
C10 C -0.0939(7) -0.0737(2) -0.2688(6) 0.0423(16) Uani 1 1 d . . .
C11 C 0.0040(7) -0.0273(2) -0.2278(6) 0.0348(14) Uani 1 1 d . . .
C12 C -0.0351(7) 0.0142(2) -0.3208(7) 0.0410(15) Uani 1 1 d . . .
H12A H -0.1240 0.0132 -0.4105 0.049 Uiso 1 1 calc R . .
C13 C 0.0564(7) 0.0579(2) -0.2830(7) 0.0433(16) Uani 1 1 d . . .
H13A H 0.0303 0.0855 -0.3492 0.052 Uiso 1 1 calc R . .
C14 C 0.1845(7) 0.0605(2) -0.1490(7) 0.0413(15) Uani 1 1 d . . .
H14A H 0.2440 0.0900 -0.1230 0.050 Uiso 1 1 calc R . .
C15 C -0.1581(9) -0.1587(3) -0.2111(9) 0.072(2) Uani 1 1 d . . .
H15A H -0.2430 -0.1526 -0.3067 0.109 Uiso 1 1 calc R . .
H15B H -0.2061 -0.1671 -0.1287 0.109 Uiso 1 1 calc R . .
H15C H -0.0912 -0.1861 -0.2268 0.109 Uiso 1 1 calc R . .
C16 C 0.3571(7) -0.1133(2) 0.2536(7) 0.0382(14) Uani 1 1 d . . .
C17 C 0.4682(7) -0.1506(2) 0.2142(8) 0.0463(16) Uani 1 1 d . . .
C18 C 0.5839(10) -0.1725(3) 0.3396(9) 0.074(2) Uani 1 1 d . . .
H18A H 0.5862 -0.1632 0.4413 0.089 Uiso 1 1 calc R . .
C19 C 0.6872(12) -0.2176(3) 0.1681(14) 0.094(3) Uani 1 1 d . . .
H19A H 0.7629 -0.2402 0.1501 0.113 Uiso 1 1 calc R . .
C20 C 0.5785(9) -0.1979(3) 0.0441(10) 0.066(2) Uani 1 1 d . . .
H20A H 0.5768 -0.2080 -0.0567 0.079 Uiso 1 1 calc R . .
C21 C 0.4691(8) -0.1628(2) 0.0636(8) 0.0492(17) Uani 1 1 d . . .
H21A H 0.3969 -0.1475 -0.0228 0.059 Uiso 1 1 calc R . .
O4 O 0.1983(12) -0.1871(4) 0.6201(12) 0.186 Uani 1 1 d D . .
C22 C 0.1608(17) -0.2131(5) 0.4803(15) 0.188 Uani 1 1 d D . .
H4A H 0.0955 -0.1923 0.3976 0.282 Uiso 1 1 calc R . .
H4B H 0.1007 -0.2428 0.4894 0.282 Uiso 1 1 calc R . .
H4C H 0.2599 -0.2222 0.4563 0.282 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 114.5(5) . . ?
N2 C1 N1 129.5(6) . . ?
N2 C1 H1B 115.3 . . ?
N1 C1 H1B 115.3 . . ?
C1 N2 C4 115.6(5) . . ?
N1 C2 C3 123.1(5) . . ?
N1 C2 H2B 118.4 . . ?
C3 C2 H2B 118.4 . . ?
C10 N3 C9 125.2(5) . . ?
C10 N3 C15 116.8(5) . . ?
C9 N3 C15 118.0(5) . . ?
C4 C3 C2 115.9(5) . . ?
C4 C3 C5 121.6(5) . . ?
C2 C3 C5 122.5(5) . . ?
N2 C4 C3 121.4(5) . . ?
N2 C4 C8 119.6(5) . . ?
C3 C4 C8 119.0(5) . . ?
C18 N4 C19 115.7(7) . . ?
C6 C5 C3 118.8(5) . . ?
C6 C5 C16 124.6(5) . . ?
C3 C5 C16 116.5(5) . . ?
C5 C6 C7 120.8(5) . . ?
C5 C6 C9 118.7(5) . . ?
C7 C6 C9 120.5(5) . . ?
C8 C7 C6 121.7(5) . . ?
C8 C7 C11 117.5(5) . . ?
C6 C7 C11 120.9(5) . . ?
C7 C8 C14 120.7(5) . . ?
C7 C8 C4 118.1(5) . . ?
C14 C8 C4 121.2(5) . . ?
O1 C9 N3 120.9(6) . . ?
O1 C9 C6 122.7(5) . . ?
N3 C9 C6 116.4(5) . . ?
O2 C10 N3 120.5(6) . . ?
O2 C10 C11 121.0(6) . . ?
N3 C10 C11 118.5(5) . . ?
C12 C11 C7 121.1(6) . . ?
C12 C11 C10 120.5(5) . . ?
C7 C11 C10 118.4(5) . . ?
C11 C12 C13 120.7(5) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C14 C13 C12 120.5(6) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C8 119.6(6) . . ?
C13 C14 H14A 120.2 . . ?
C8 C14 H14A 120.2 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 C17 122.8(6) . . ?
O3 C16 C5 119.8(6) . . ?
C17 C16 C5 117.0(5) . . ?
C21 C17 C18 118.6(7) . . ?
C21 C17 C16 124.6(6) . . ?
C18 C17 C16 116.7(6) . . ?
N4 C18 C17 122.7(8) . . ?
N4 C18 H18A 118.7 . . ?
C17 C18 H18A 118.7 . . ?
C20 C19 N4 123.9(8) . . ?
C20 C19 H19A 118.0 . . ?
N4 C19 H19A 118.0 . . ?
C19 C20 C21 120.5(8) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C20 C21 C17 118.5(7) . . ?
C20 C21 H21A 120.8 . . ?
C17 C21 H21A 120.8 . . ?
O4 C22 H4A 109.5 . . ?
O4 C22 H4B 109.5 . . ?
H4A C22 H4B 109.5 . . ?
O4 C22 H4C 109.5 . . ?
H4A C22 H4C 109.5 . . ?
H4B C22 H4C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.207(7) . ?
N1 C2 1.308(7) . ?
N1 C1 1.351(8) . ?
C1 N2 1.301(7) . ?
C1 H1B 0.9300 . ?
O2 C10 1.226(6) . ?
N2 C4 1.359(7) . ?
C2 C3 1.425(7) . ?
C2 H2B 0.9300 . ?
O3 C16 1.202(6) . ?
N3 C10 1.372(8) . ?
N3 C9 1.403(7) . ?
N3 C15 1.473(8) . ?
C3 C4 1.394(7) . ?
C3 C5 1.436(7) . ?
C4 C8 1.453(7) . ?
N4 C18 1.360(10) . ?
N4 C19 1.361(11) . ?
C5 C6 1.374(7) . ?
C5 C16 1.517(8) . ?
C6 C7 1.412(7) . ?
C6 C9 1.474(8) . ?
C7 C8 1.401(7) . ?
C7 C11 1.424(7) . ?
C8 C14 1.422(8) . ?
C10 C11 1.482(8) . ?
C11 C12 1.364(8) . ?
C12 C13 1.392(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.368(8) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.484(9) . ?
C17 C21 1.376(8) . ?
C17 C18 1.389(9) . ?
C18 H18A 0.9300 . ?
C19 C20 1.330(11) . ?
C19 H19A 0.9300 . ?
C20 C21 1.368(9) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
O4 C22 1.377(8) . ?
C22 H4A 0.9600 . ?
C22 H4B 0.9600 . ?
C22 H4C 0.9600 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -0.5(10) . . . . ?
N1 C1 N2 C4 -0.1(10) . . . . ?
C1 N1 C2 C3 0.4(9) . . . . ?
N1 C2 C3 C4 0.2(8) . . . . ?
N1 C2 C3 C5 -179.0(5) . . . . ?
C1 N2 C4 C3 0.7(8) . . . . ?
C1 N2 C4 C8 -179.9(5) . . . . ?
C2 C3 C4 N2 -0.8(8) . . . . ?
C5 C3 C4 N2 178.4(5) . . . . ?
C2 C3 C4 C8 179.9(5) . . . . ?
C5 C3 C4 C8 -0.9(8) . . . . ?
C4 C3 C5 C6 -1.3(8) . . . . ?
C2 C3 C5 C6 177.9(5) . . . . ?
C4 C3 C5 C16 -179.0(5) . . . . ?
C2 C3 C5 C16 0.2(8) . . . . ?
C3 C5 C6 C7 2.6(8) . . . . ?
C16 C5 C6 C7 -179.9(5) . . . . ?
C3 C5 C6 C9 -176.6(5) . . . . ?
C16 C5 C6 C9 0.8(8) . . . . ?
C5 C6 C7 C8 -1.8(8) . . . . ?
C9 C6 C7 C8 177.5(5) . . . . ?
C5 C6 C7 C11 177.9(5) . . . . ?
C9 C6 C7 C11 -2.9(8) . . . . ?
C6 C7 C8 C14 -179.9(5) . . . . ?
C11 C7 C8 C14 0.5(8) . . . . ?
C6 C7 C8 C4 -0.5(8) . . . . ?
C11 C7 C8 C4 179.9(5) . . . . ?
N2 C4 C8 C7 -177.6(5) . . . . ?
C3 C4 C8 C7 1.8(7) . . . . ?
N2 C4 C8 C14 1.8(8) . . . . ?
C3 C4 C8 C14 -178.9(5) . . . . ?
C10 N3 C9 O1 -179.6(6) . . . . ?
C15 N3 C9 O1 -2.7(9) . . . . ?
C10 N3 C9 C6 1.9(9) . . . . ?
C15 N3 C9 C6 178.9(6) . . . . ?
C5 C6 C9 O1 2.3(9) . . . . ?
C7 C6 C9 O1 -176.9(6) . . . . ?
C5 C6 C9 N3 -179.2(5) . . . . ?
C7 C6 C9 N3 1.5(8) . . . . ?
C9 N3 C10 O2 177.7(6) . . . . ?
C15 N3 C10 O2 0.7(9) . . . . ?
C9 N3 C10 C11 -3.7(9) . . . . ?
C15 N3 C10 C11 179.3(6) . . . . ?
C8 C7 C11 C12 -1.2(8) . . . . ?
C6 C7 C11 C12 179.2(5) . . . . ?
C8 C7 C11 C10 -179.3(5) . . . . ?
C6 C7 C11 C10 1.0(8) . . . . ?
O2 C10 C11 C12 2.6(9) . . . . ?
N3 C10 C11 C12 -176.0(5) . . . . ?
O2 C10 C11 C7 -179.3(5) . . . . ?
N3 C10 C11 C7 2.2(8) . . . . ?
C7 C11 C12 C13 1.9(9) . . . . ?
C10 C11 C12 C13 -180.0(5) . . . . ?
C11 C12 C13 C14 -2.0(9) . . . . ?
C12 C13 C14 C8 1.3(9) . . . . ?
C7 C8 C14 C13 -0.6(8) . . . . ?
C4 C8 C14 C13 -179.9(5) . . . . ?
C6 C5 C16 O3 -100.7(7) . . . . ?
C3 C5 C16 O3 76.9(7) . . . . ?
C6 C5 C16 C17 86.5(7) . . . . ?
C3 C5 C16 C17 -96.0(6) . . . . ?
O3 C16 C17 C21 155.6(6) . . . . ?
C5 C16 C17 C21 -31.8(8) . . . . ?
O3 C16 C17 C18 -27.9(9) . . . . ?
C5 C16 C17 C18 144.8(6) . . . . ?
C19 N4 C18 C17 1.8(14) . . . . ?
C21 C17 C18 N4 -2.6(12) . . . . ?
C16 C17 C18 N4 -179.4(8) . . . . ?
C18 N4 C19 C20 -2.0(15) . . . . ?
N4 C19 C20 C21 3.0(14) . . . . ?
C19 C20 C21 C17 -3.6(11) . . . . ?
C18 C17 C21 C20 3.4(10) . . . . ?
C16 C17 C21 C20 179.9(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659187
