#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/34/7013461.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_7013461
loop_
_publ_author_name
'Licchelli, Maurizio'
'Biroli, Alessio Orbelli'
'Poggi, Antonio'
'Sacchi, Donatella'
'Sangermani, Corrado'
'Zema, Michele'
_publ_section_title
;
 Excimer emission induced by metal ion coordination in
 1,8-naphthalimide-tethered iminopyridine ligands
;
_journal_issue                   23
_journal_name_full               'Dalton Transactions'
_journal_page_first              4537
_journal_paper_doi               10.1039/b308439f
_journal_year                    2003
_chemical_formula_moiety         'C20 H15 N3 O2'
_chemical_formula_sum            'C20 H15 N3 O2'
_chemical_formula_weight         329.35
_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                 109.57(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.756(3)
_cell_length_b                   13.355(6)
_cell_length_c                   12.837(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10.58
_cell_measurement_theta_min      6.51
_cell_volume                     1575.9(12)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled 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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4769
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  240
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0469
_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)+(0.0554P)²+0.2424P],P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1374
_reflns_number_gt                2609
_reflns_number_total             4585
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b308439f.txt
_cod_data_source_block           licc21
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7013461
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
C1 C 1.1869(2) 0.54587(14) -0.10975(17) 0.0583(5) Uani 1 1 d . . .
C2 C 1.3166(2) 0.56347(15) -0.02862(17) 0.0609(5) Uani 1 1 d . . .
C3 C 1.3580(2) 0.50243(16) 0.06275(17) 0.0619(5) Uani 1 1 d . . .
C4 C 1.2671(2) 0.42551(15) 0.06903(15) 0.0557(4) Uani 1 1 d . . .
C5 C 1.13690(17) 0.41408(12) -0.01582(13) 0.0459(4) Uani 1 1 d . . .
C6 C 1.03162(19) 0.33564(13) -0.01399(14) 0.0495(4) Uani 1 1 d . . .
C7 C 0.9473(2) 0.19330(15) 0.04661(16) 0.0534(4) Uani 1 1 d . . .
C8 C 0.94776(19) 0.16689(15) 0.16075(15) 0.0515(4) Uani 1 1 d . . .
C9 C 0.69835(18) 0.14161(12) 0.15852(14) 0.0478(4) Uani 1 1 d . . .
C10 C 0.84873(17) -0.00281(12) 0.14369(13) 0.0439(4) Uani 1 1 d . . .
C11 C 0.57694(16) 0.07322(12) 0.14997(12) 0.0429(3) Uani 1 1 d . . .
C12 C 0.44527(19) 0.11107(16) 0.14807(14) 0.0536(4) Uani 1 1 d . . .
C13 C 0.33218(19) 0.04640(18) 0.14715(16) 0.0625(5) Uani 1 1 d . . .
C14 C 0.35085(19) -0.05423(17) 0.14783(15) 0.0601(5) Uani 1 1 d . . .
C15 C 0.48189(18) -0.09665(13) 0.14504(13) 0.0488(4) Uani 1 1 d . . .
C16 C 0.5054(2) -0.20030(15) 0.14141(16) 0.0614(5) Uani 1 1 d . . .
C17 C 0.6332(2) -0.23694(15) 0.13749(17) 0.0648(5) Uani 1 1 d . . .
C18 C 0.7466(2) -0.17193(13) 0.13812(15) 0.0549(4) Uani 1 1 d . . .
C19 C 0.72916(17) -0.07071(12) 0.14299(12) 0.0431(3) Uani 1 1 d . . .
C20 C 0.59688(16) -0.03092(12) 0.14605(12) 0.0412(3) Uani 1 1 d . . .
N1 N 1.09486(15) 0.47301(11) -0.10494(12) 0.0546(4) Uani 1 1 d . . .
N2 N 1.06231(15) 0.26511(11) 0.05458(12) 0.0531(4) Uani 1 1 d . . .
N3 N 0.82674(14) 0.09916(10) 0.15492(11) 0.0454(3) Uani 1 1 d . . .
O1 O 0.68958(15) 0.23169(9) 0.16968(13) 0.0723(4) Uani 1 1 d . . .
O2 O 0.96193(12) -0.03218(10) 0.13440(11) 0.0582(3) Uani 1 1 d . . .
H1 H 1.151(2) 0.5859(16) -0.1780(18) 0.077(6) Uiso 1 1 d . . .
H2 H 1.375(2) 0.6193(15) -0.0353(16) 0.069(6) Uiso 1 1 d . . .
H3 H 1.453(2) 0.5128(15) 0.1234(18) 0.077(6) Uiso 1 1 d . . .
H4 H 1.2895(19) 0.3783(15) 0.1296(16) 0.067(6) Uiso 1 1 d . . .
H6 H 0.933(2) 0.3433(14) -0.0724(16) 0.069(6) Uiso 1 1 d . . .
H7A H 0.850(2) 0.2203(13) -0.0008(15) 0.057(5) Uiso 1 1 d . . .
H7B H 0.967(2) 0.1338(16) 0.0106(16) 0.070(6) Uiso 1 1 d . . .
H8A H 0.9339(19) 0.2254(14) 0.2005(15) 0.058(5) Uiso 1 1 d . . .
H8B H 1.036(2) 0.1341(14) 0.2059(15) 0.059(5) Uiso 1 1 d . . .
H12 H 0.432(2) 0.1826(16) 0.1464(16) 0.073(6) Uiso 1 1 d . . .
H13 H 0.242(2) 0.0730(16) 0.1463(17) 0.078(6) Uiso 1 1 d . . .
H14 H 0.276(2) -0.1002(16) 0.1490(16) 0.071(6) Uiso 1 1 d . . .
H16 H 0.430(2) -0.2468(17) 0.1456(18) 0.085(7) Uiso 1 1 d . . .
H17 H 0.648(2) -0.3079(18) 0.1325(18) 0.087(7) Uiso 1 1 d . . .
H18 H 0.840(2) -0.1961(15) 0.1361(16) 0.072(6) Uiso 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'
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'
H H 0.0000 0.0000 '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
N1 C1 C2 123.71(19) . . ?
N1 C1 H1 113.0(12) . . ?
C2 C1 H1 123.3(12) . . ?
C1 C2 C3 118.84(18) . . ?
C1 C2 H2 119.5(12) . . ?
C3 C2 H2 121.7(12) . . ?
C2 C3 C4 118.82(18) . . ?
C2 C3 H3 120.9(12) . . ?
C4 C3 H3 120.3(12) . . ?
C3 C4 C5 118.54(18) . . ?
C3 C4 H4 123.8(11) . . ?
C5 C4 H4 117.6(11) . . ?
N1 C5 C4 123.35(16) . . ?
N1 C5 C6 114.66(15) . . ?
C4 C5 C6 121.99(16) . . ?
N2 C6 C5 122.77(16) . . ?
N2 C6 H6 122.9(11) . . ?
C5 C6 H6 114.3(11) . . ?
N2 C7 C8 109.59(15) . . ?
N2 C7 H7A 110.8(10) . . ?
C8 C7 H7A 111.5(10) . . ?
N2 C7 H7B 107.6(12) . . ?
C8 C7 H7B 109.6(12) . . ?
H7A C7 H7B 107.6(15) . . ?
N3 C8 C7 110.74(14) . . ?
N3 C8 H8A 105.8(11) . . ?
C7 C8 H8A 111.6(11) . . ?
N3 C8 H8B 107.1(11) . . ?
C7 C8 H8B 113.5(11) . . ?
H8A C8 H8B 107.7(15) . . ?
O1 C9 N3 120.43(15) . . ?
O1 C9 C11 122.40(16) . . ?
N3 C9 C11 117.17(14) . . ?
O2 C10 N3 120.14(15) . . ?
O2 C10 C19 122.95(15) . . ?
N3 C10 C19 116.91(13) . . ?
C12 C11 C20 120.18(16) . . ?
C12 C11 C9 119.87(16) . . ?
C20 C11 C9 119.93(14) . . ?
C11 C12 C13 120.24(19) . . ?
C11 C12 H12 118.9(12) . . ?
C13 C12 H12 120.8(12) . . ?
C14 C13 C12 120.55(17) . . ?
C14 C13 H13 119.7(13) . . ?
C12 C13 H13 119.8(13) . . ?
C13 C14 C15 121.28(17) . . ?
C13 C14 H14 122.1(12) . . ?
C15 C14 H14 116.6(12) . . ?
C16 C15 C14 123.78(17) . . ?
C16 C15 C20 118.10(17) . . ?
C14 C15 C20 118.12(17) . . ?
C17 C16 C15 121.26(18) . . ?
C17 C16 H16 119.5(13) . . ?
C15 C16 H16 119.2(13) . . ?
C16 C17 C18 120.59(19) . . ?
C16 C17 H17 121.3(13) . . ?
C18 C17 H17 118.1(13) . . ?
C19 C18 C17 120.17(18) . . ?
C19 C18 H18 117.4(12) . . ?
C17 C18 H18 122.4(12) . . ?
C18 C19 C20 120.24(15) . . ?
C18 C19 C10 119.89(15) . . ?
C20 C19 C10 119.86(14) . . ?
C11 C20 C19 120.85(14) . . ?
C11 C20 C15 119.51(14) . . ?
C19 C20 C15 119.64(15) . . ?
C5 N1 C1 116.72(15) . . ?
C6 N2 C7 116.65(15) . . ?
C9 N3 C10 125.01(13) . . ?
C9 N3 C8 117.71(14) . . ?
C10 N3 C8 117.26(14) . . ?
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
C1 N1 1.339(2) . ?
C1 C2 1.363(3) . ?
C1 H1 0.98(2) . ?
C2 C3 1.373(3) . ?
C2 H2 0.96(2) . ?
C3 C4 1.377(3) . ?
C3 H3 1.00(2) . ?
C4 C5 1.377(2) . ?
C4 H4 0.97(2) . ?
C5 N1 1.335(2) . ?
C5 C6 1.473(2) . ?
C6 N2 1.255(2) . ?
C6 H6 1.007(19) . ?
C7 N2 1.454(2) . ?
C7 C8 1.505(3) . ?
C7 H7A 1.007(18) . ?
C7 H7B 0.97(2) . ?
C8 N3 1.469(2) . ?
C8 H8A 0.968(19) . ?
C8 H8B 0.969(18) . ?
C9 O1 1.218(2) . ?
C9 N3 1.390(2) . ?
C9 C11 1.470(2) . ?
C10 O2 1.2149(18) . ?
C10 N3 1.394(2) . ?
C10 C19 1.475(2) . ?
C11 C12 1.373(2) . ?
C11 C20 1.408(2) . ?
C12 C13 1.398(3) . ?
C12 H12 0.96(2) . ?
C13 C14 1.356(3) . ?
C13 H13 0.95(2) . ?
C14 C15 1.410(3) . ?
C14 H14 0.96(2) . ?
C15 C16 1.407(3) . ?
C15 C20 1.421(2) . ?
C16 C17 1.356(3) . ?
C16 H16 0.98(2) . ?
C17 C18 1.404(3) . ?
C17 H17 0.96(2) . ?
C18 C19 1.366(2) . ?
C18 H18 0.98(2) . ?
C19 C20 1.408(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652764
