#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/31/54/4315485.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_4315485
loop_
_publ_author_name
'Wen-Fu Fu'
'Lin-Fang Jia'
'Wei-Hua Mu'
'Xin Gan'
'Jia-Bing Zhang'
'Ping-Hua Liu'
'Qian-Yong Cao'
'Gui-Ju Zhang'
'Li Quan'
'Xiao-Jun Lv'
'Quan-Qing Xu'
_publ_section_title
;
 Synthesis, Characterization, Photoinduced Isomerization, and
 Spectroscopic Properties of Vinyl-1,8-naphthyridine Derivatives and Their
 Copper(I) Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4524
_journal_page_last               4533
_journal_paper_doi               10.1021/ic100094y
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C24 H20 N4 O3'
_chemical_formula_weight         412.44
_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                 105.636(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5987(18)
_cell_length_b                   22.941(4)
_cell_length_c                   7.9527(11)
_cell_measurement_reflns_used    3022
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.55
_cell_volume                     2037.8(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11561
_diffrn_reflns_theta_full        26.67
_diffrn_reflns_theta_max         26.67
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0427
_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)+(0.0510P)²+0.2932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                2550
_reflns_number_total             4253
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic100094y_si_001_3.cif
_cod_data_source_block           50613c
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' 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               4315485
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
N1 N 0.11821(13) -0.00623(6) 0.19748(18) 0.0475(4) Uani 1 1 d . . .
N2 N 0.10721(13) -0.10720(6) 0.17055(18) 0.0479(4) Uani 1 1 d . . .
N3 N 0.49710(13) 0.10562(6) 0.22225(18) 0.0442(4) Uani 1 1 d . . .
N4 N 0.48494(15) 0.20487(7) 0.1603(2) 0.0605(4) Uani 1 1 d . . .
O1 O 0.01891(15) -0.28721(7) 0.1663(2) 0.0858(5) Uani 1 1 d . . .
O2 O 0.61571(15) 0.04453(7) 0.1136(2) 0.0816(5) Uani 1 1 d . . .
O3 O 0.49319(16) 0.11555(7) 0.50106(18) 0.0819(5) Uani 1 1 d . . .
C1 C 0.07000(16) 0.04432(8) 0.2298(2) 0.0493(5) Uani 1 1 d . . .
C2 C -0.04016(18) 0.04622(10) 0.2699(3) 0.0629(5) Uani 1 1 d . . .
H2 H -0.0734 0.0818 0.2878 0.075 Uiso 1 1 calc R . .
C3 C -0.09854(18) -0.00462(10) 0.2828(3) 0.0669(6) Uani 1 1 d . . .
H3 H -0.1713 -0.0035 0.3110 0.080 Uiso 1 1 calc R . .
C4 C -0.05054(16) -0.05785(9) 0.2544(2) 0.0534(5) Uani 1 1 d . . .
C5 C 0.05799(16) -0.05486(8) 0.2079(2) 0.0464(4) Uani 1 1 d . . .
C6 C 0.05572(16) -0.16135(8) 0.1827(2) 0.0504(5) Uani 1 1 d . . .
C7 C -0.05093(18) -0.16311(9) 0.2375(3) 0.0600(5) Uani 1 1 d . . .
H7 H -0.0857 -0.1988 0.2504 0.072 Uiso 1 1 calc R . .
C8 C -0.10178(18) -0.11345(10) 0.2708(3) 0.0640(6) Uani 1 1 d . . .
H8 H -0.1722 -0.1153 0.3053 0.077 Uiso 1 1 calc R . .
C9 C 0.21081(17) -0.11502(9) 0.1189(3) 0.0575(5) Uani 1 1 d . . .
H9 H 0.2612 -0.0857 0.0996 0.069 Uiso 1 1 calc R . .
C10 C 0.22571(18) -0.17324(9) 0.1014(3) 0.0604(5) Uani 1 1 d . . .
H10 H 0.2891 -0.1905 0.0692 0.073 Uiso 1 1 calc R . .
C11 C 0.12937(17) -0.20369(9) 0.1400(2) 0.0548(5) Uani 1 1 d . . .
C12 C 0.1107(2) -0.26647(9) 0.1417(3) 0.0616(6) Uani 1 1 d . . .
C13 C 0.2076(2) -0.30531(9) 0.1156(3) 0.0758(7) Uani 1 1 d . . .
H13A H 0.2766 -0.3021 0.2141 0.114 Uiso 1 1 calc R . .
H13B H 0.2287 -0.2939 0.0115 0.114 Uiso 1 1 calc R . .
H13C H 0.1800 -0.3449 0.1042 0.114 Uiso 1 1 calc R . .
C14 C 0.13394(18) 0.09837(8) 0.2202(2) 0.0533(5) Uani 1 1 d . . .
H14 H 0.0966 0.1331 0.2358 0.064 Uiso 1 1 calc R . .
C15 C 0.24096(17) 0.10212(8) 0.1910(2) 0.0500(5) Uani 1 1 d . . .
H15 H 0.2800 0.0674 0.1817 0.060 Uiso 1 1 calc R . .
C16 C 0.42435(17) 0.15780(7) 0.1833(2) 0.0464(4) Uani 1 1 d . . .
C17 C 0.30277(17) 0.15621(7) 0.1723(2) 0.0466(4) Uani 1 1 d . . .
C18 C 0.24238(19) 0.20958(8) 0.1328(3) 0.0586(5) Uani 1 1 d . . .
H18 H 0.1609 0.2117 0.1240 0.070 Uiso 1 1 calc R . .
C19 C 0.3028(2) 0.25835(9) 0.1071(3) 0.0662(6) Uani 1 1 d . . .
H19 H 0.2629 0.2937 0.0804 0.079 Uiso 1 1 calc R . .
C20 C 0.4229(2) 0.25460(8) 0.1213(3) 0.0681(6) Uani 1 1 d . . .
H20 H 0.4632 0.2881 0.1030 0.082 Uiso 1 1 calc R . .
C21 C 0.53621(18) 0.08004(9) 0.0865(2) 0.0539(5) Uani 1 1 d . . .
C22 C 0.4709(2) 0.09815(10) -0.0938(3) 0.0711(6) Uani 1 1 d . . .
H22A H 0.4992 0.0758 -0.1767 0.107 Uiso 1 1 calc R . .
H22B H 0.4847 0.1388 -0.1090 0.107 Uiso 1 1 calc R . .
H22C H 0.3867 0.0915 -0.1120 0.107 Uiso 1 1 calc R . .
C23 C 0.53520(18) 0.08967(8) 0.3994(2) 0.0520(5) Uani 1 1 d . . .
C24 C 0.6231(2) 0.04173(9) 0.4590(3) 0.0708(6) Uani 1 1 d . . .
H24A H 0.6305 0.0335 0.5798 0.106 Uiso 1 1 calc R . .
H24B H 0.6995 0.0533 0.4450 0.106 Uiso 1 1 calc R . .
H24C H 0.5959 0.0074 0.3906 0.106 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
C5 N1 C1 117.38(16) . . ?
C9 N2 C6 109.15(16) . . ?
C9 N2 C5 127.82(16) . . ?
C6 N2 C5 123.03(15) . . ?
C23 N3 C21 125.50(15) . . ?
C23 N3 C16 115.89(14) . . ?
C21 N3 C16 118.05(14) . . ?
C16 N4 C20 116.95(18) . . ?
N1 C1 C2 121.60(18) . . ?
N1 C1 C14 118.77(16) . . ?
C2 C1 C14 119.62(18) . . ?
C3 C2 C1 119.48(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.74(19) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 115.30(18) . . ?
C3 C4 C8 125.25(18) . . ?
C5 C4 C8 119.45(19) . . ?
N1 C5 N2 117.17(16) . . ?
N1 C5 C4 125.41(17) . . ?
N2 C5 C4 117.42(17) . . ?
N2 C6 C11 107.59(16) . . ?
N2 C6 C7 118.19(18) . . ?
C11 C6 C7 134.18(18) . . ?
C8 C7 C6 120.16(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C4 121.66(19) . . ?
C7 C8 H8 119.2 . . ?
C4 C8 H8 119.2 . . ?
C10 C9 N2 107.63(17) . . ?
C10 C9 H9 126.2 . . ?
N2 C9 H9 126.2 . . ?
C9 C10 C11 109.41(18) . . ?
C9 C10 H10 125.3 . . ?
C11 C10 H10 125.3 . . ?
C6 C11 C10 106.22(17) . . ?
C6 C11 C12 125.73(19) . . ?
C10 C11 C12 128.0(2) . . ?
O1 C12 C11 121.4(2) . . ?
O1 C12 C13 120.6(2) . . ?
C11 C12 C13 118.0(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C1 125.31(17) . . ?
C15 C14 H14 117.3 . . ?
C1 C14 H14 117.3 . . ?
C14 C15 C17 125.55(17) . . ?
C14 C15 H15 117.2 . . ?
C17 C15 H15 117.2 . . ?
N4 C16 C17 125.34(16) . . ?
N4 C16 N3 113.70(16) . . ?
C17 C16 N3 120.96(15) . . ?
C16 C17 C18 115.34(17) . . ?
C16 C17 C15 122.24(16) . . ?
C18 C17 C15 122.34(18) . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.22(19) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
N4 C20 C19 122.9(2) . . ?
N4 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
O2 C21 N3 122.26(18) . . ?
O2 C21 C22 121.79(18) . . ?
N3 C21 C22 115.92(18) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 N3 117.94(17) . . ?
O3 C23 C24 121.06(18) . . ?
N3 C23 C24 120.99(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N1 C5 1.331(2) . ?
N1 C1 1.342(2) . ?
N2 C9 1.382(2) . ?
N2 C6 1.393(2) . ?
N2 C5 1.395(2) . ?
N3 C23 1.406(2) . ?
N3 C21 1.407(2) . ?
N3 C16 1.449(2) . ?
N4 C16 1.328(2) . ?
N4 C20 1.340(3) . ?
O1 C12 1.229(2) . ?
O2 C21 1.205(2) . ?
O3 C23 1.207(2) . ?
C1 C2 1.399(3) . ?
C1 C14 1.457(3) . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(2) . ?
C4 C8 1.428(3) . ?
C6 C11 1.395(3) . ?
C6 C7 1.419(3) . ?
C7 C8 1.342(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.359(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.420(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.457(3) . ?
C12 C13 1.492(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.325(3) . ?
C14 H14 0.9300 . ?
C15 C17 1.461(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(3) . ?
C17 C18 1.403(2) . ?
C18 C19 1.364(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.370(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.489(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.487(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C5 N1 C1 C2 -1.1(3) . . . . ?
C5 N1 C1 C14 179.74(15) . . . . ?
N1 C1 C2 C3 2.3(3) . . . . ?
C14 C1 C2 C3 -178.48(18) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C2 C3 C4 C8 177.6(2) . . . . ?
C1 N1 C5 N2 178.66(15) . . . . ?
C1 N1 C5 C4 -1.8(3) . . . . ?
C9 N2 C5 N1 -1.8(3) . . . . ?
C6 N2 C5 N1 177.58(15) . . . . ?
C9 N2 C5 C4 178.59(17) . . . . ?
C6 N2 C5 C4 -2.0(2) . . . . ?
C3 C4 C5 N1 3.2(3) . . . . ?
C8 C4 C5 N1 -176.19(17) . . . . ?
C3 C4 C5 N2 -177.29(16) . . . . ?
C8 C4 C5 N2 3.4(3) . . . . ?
C9 N2 C6 C11 0.8(2) . . . . ?
C5 N2 C6 C11 -178.75(15) . . . . ?
C9 N2 C6 C7 178.79(16) . . . . ?
C5 N2 C6 C7 -0.7(2) . . . . ?
N2 C6 C7 C8 2.1(3) . . . . ?
C11 C6 C7 C8 179.5(2) . . . . ?
C6 C7 C8 C4 -0.7(3) . . . . ?
C3 C4 C8 C7 178.6(2) . . . . ?
C5 C4 C8 C7 -2.1(3) . . . . ?
C6 N2 C9 C10 -1.0(2) . . . . ?
C5 N2 C9 C10 178.52(17) . . . . ?
N2 C9 C10 C11 0.8(2) . . . . ?
N2 C6 C11 C10 -0.26(19) . . . . ?
C7 C6 C11 C10 -177.8(2) . . . . ?
N2 C6 C11 C12 177.91(17) . . . . ?
C7 C6 C11 C12 0.3(3) . . . . ?
C9 C10 C11 C6 -0.3(2) . . . . ?
C9 C10 C11 C12 -178.45(19) . . . . ?
C6 C11 C12 O1 7.1(3) . . . . ?
C10 C11 C12 O1 -175.1(2) . . . . ?
C6 C11 C12 C13 -171.85(18) . . . . ?
C10 C11 C12 C13 5.9(3) . . . . ?
N1 C1 C14 C15 -3.9(3) . . . . ?
C2 C1 C14 C15 176.86(18) . . . . ?
C1 C14 C15 C17 176.61(17) . . . . ?
C20 N4 C16 C17 -0.8(3) . . . . ?
C20 N4 C16 N3 179.05(16) . . . . ?
C23 N3 C16 N4 99.73(18) . . . . ?
C21 N3 C16 N4 -72.1(2) . . . . ?
C23 N3 C16 C17 -80.4(2) . . . . ?
C21 N3 C16 C17 107.72(19) . . . . ?
N4 C16 C17 C18 0.2(3) . . . . ?
N3 C16 C17 C18 -179.62(15) . . . . ?
N4 C16 C17 C15 176.99(16) . . . . ?
N3 C16 C17 C15 -2.8(3) . . . . ?
C14 C15 C17 C16 164.36(18) . . . . ?
C14 C15 C17 C18 -19.1(3) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C15 C17 C18 C19 -176.42(17) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C16 N4 C20 C19 0.8(3) . . . . ?
C18 C19 C20 N4 -0.3(3) . . . . ?
C23 N3 C21 O2 -6.6(3) . . . . ?
C16 N3 C21 O2 164.37(18) . . . . ?
C23 N3 C21 C22 171.60(17) . . . . ?
C16 N3 C21 C22 -17.4(2) . . . . ?
C21 N3 C23 O3 -179.74(19) . . . . ?
C16 N3 C23 O3 9.1(3) . . . . ?
C21 N3 C23 C24 -0.7(3) . . . . ?
C16 N3 C23 C24 -171.90(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660977
