#------------------------------------------------------------------------------
#$Date: 2025-08-22 16:55:42 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301864 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/14/7211441.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_7211441
loop_
_publ_author_name
'd'Agostino, Simone'
'Grepioni, Fabrizia'
'Braga, Dario'
'Moreschi, Daniele'
'Fattori, Valeria'
'Delchiaro, Francesca'
'Di Motta, Simone'
'Negri, Fabrizia'
_publ_section_title
;
 Exciton coupling in molecular salts of 2-(1,8-naphthalimido)ethanoic acid
 and cyclic amines: modulation of the solid-state luminescence
;
_journal_issue                   48
_journal_name_full               CrystEngComm
_journal_page_first              10470
_journal_paper_doi               10.1039/c3ce41651h
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C32 H36 N4 O12'
_chemical_formula_weight         668.64
_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                 100.002(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.0482(16)
_cell_length_b                   6.7332(6)
_cell_length_c                   14.5030(19)
_cell_measurement_reflns_used    819
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3590
_cell_measurement_theta_min      2.7150
_cell_volume                     1543.3(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1340
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measurement_details
;
  1 omega  -17.00   20.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5173  -99.0000  150.0000 37

  2 omega   20.00   91.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0017   38.0000 -120.0000 71

  3 omega  -52.00   61.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0017  -19.0000   60.0000 113

;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.1324
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6682
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.42
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0032(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1919
_refine_ls_R_factor_gt           0.0642
_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)+(0.0403P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1411
_reflns_number_gt                1441
_reflns_number_total             3518
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ce41651h.txt
_cod_data_source_block           nmigly2a1piperazina_3_r2
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7211441
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
O1W O 0.14646(19) 0.8390(5) 0.2990(2) 0.0636(8) Uani 1 1 d .
N3 N 0.94776(18) 0.8388(4) 0.4587(2) 0.0422(8) Uani 1 1 d .
C2V C 0.9413(2) 1.0390(4) 0.4144(2) 0.0454(9) Uani 1 1 d .
H2V1 H 0.8838 1.0618 0.3824 0.054 Uiso 1 1 calc R
H2V2 H 0.9786 1.0467 0.3686 0.054 Uiso 1 1 calc R
C1V C 1.0344(2) 0.8047(4) 0.5113(3) 0.0480(10) Uani 1 1 d .
H1V1 H 1.0743 0.8069 0.4682 0.058 Uiso 1 1 calc R
H1V2 H 1.0372 0.6746 0.5404 0.058 Uiso 1 1 calc R
O2W O 0.9654(2) 1.5581(5) 0.3261(2) 0.0820(11) Uani 1 1 d .
H2X H 0.899(3) 0.821(5) 0.503(3) 0.111(15) Uiso 1 1 d .
H1X H 0.936(2) 0.743(5) 0.411(3) 0.075(13) Uiso 1 1 d .
H1WA H 0.147(3) 0.717(6) 0.328(3) 0.099(16) Uiso 1 1 d .
H2WA H 1.020(2) 1.516(5) 0.337(3) 0.075(14) Uiso 1 1 d .
H1WB H 0.165(3) 0.925(7) 0.342(3) 0.12(2) Uiso 1 1 d .
H2WB H 0.935(3) 1.479(6) 0.288(3) 0.12(2) Uiso 1 1 d .
O2 O 0.13303(13) 0.4849(3) 0.39511(17) 0.0504(7) Uani 1 1 d .
N1 N 0.29310(16) 0.1983(3) 0.3098(2) 0.0357(7) Uani 1 1 d .
O1 O 0.16522(13) 0.1648(3) 0.41479(17) 0.0485(7) Uani 1 1 d .
C6 C 0.35467(19) -0.1598(4) 0.2469(2) 0.0332(8) Uani 1 1 d .
O3 O 0.38384(15) 0.1699(3) 0.44684(17) 0.0525(7) Uani 1 1 d .
O4 O 0.20508(15) 0.2334(3) 0.17054(18) 0.0586(8) Uani 1 1 d .
C12 C 0.2601(2) 0.1361(5) 0.2190(3) 0.0393(9) Uani 1 1 d .
C5 C 0.3848(2) -0.3419(5) 0.2162(3) 0.0398(9) Uani 1 1 d .
C1 C 0.38597(19) -0.0917(4) 0.3384(2) 0.0335(8) Uani 1 1 d .
C7 C 0.29435(19) -0.0502(4) 0.1860(2) 0.0368(8) Uani 1 1 d .
C2 C 0.44453(19) -0.2026(4) 0.3965(3) 0.0428(9) Uani 1 1 d .
H2 H 0.4648 -0.1576 0.4569 0.051 Uiso 1 1 calc R
C4 C 0.4444(2) -0.4511(5) 0.2791(3) 0.0489(10) Uani 1 1 d .
H4 H 0.4636 -0.5724 0.2605 0.059 Uiso 1 1 calc R
C14 C 0.17822(19) 0.3361(5) 0.3862(2) 0.0361(8) Uani 1 1 d .
C11 C 0.3561(2) 0.0990(4) 0.3707(3) 0.0364(8) Uani 1 1 d .
C13 C 0.2558(2) 0.3753(4) 0.3435(2) 0.0437(9) Uani 1 1 d .
H13A H 0.2409 0.4668 0.2916 0.052 Uiso 1 1 calc R
H13B H 0.2981 0.4397 0.3898 0.052 Uiso 1 1 calc R
C3 C 0.4742(2) -0.3820(5) 0.3666(3) 0.0490(10) Uani 1 1 d .
H3 H 0.5146 -0.4545 0.4067 0.059 Uiso 1 1 calc R
C10 C 0.3513(2) -0.4078(5) 0.1253(3) 0.0557(11) Uani 1 1 d .
H10 H 0.3693 -0.5287 0.1047 0.067 Uiso 1 1 calc R
C8 C 0.2641(2) -0.1180(5) 0.0979(3) 0.0550(11) Uani 1 1 d .
H8 H 0.2241 -0.0440 0.0580 0.066 Uiso 1 1 calc R
C9 C 0.2933(3) -0.2996(6) 0.0668(3) 0.0639(11) Uani 1 1 d .
H9 H 0.2729 -0.3449 0.0065 0.077 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_3
C1V N3 C2V 110.6(2) .
N3 C2V C1V 109.5(3) 3_776
N3 C1V C2V 111.2(3) 3_776
C11 N1 C12 124.7(3) .
C11 N1 C13 118.4(3) .
C12 N1 C13 116.9(3) .
C7 C6 C1 121.0(3) .
C7 C6 C5 119.6(3) .
C1 C6 C5 119.4(3) .
O4 C12 N1 120.0(3) .
O4 C12 C7 122.8(3) .
N1 C12 C7 117.2(3) .
C10 C5 C4 123.3(3) .
C10 C5 C6 118.1(3) .
C4 C5 C6 118.6(3) .
C2 C1 C6 119.7(3) .
C2 C1 C11 120.3(3) .
C6 C1 C11 119.9(3) .
C8 C7 C6 120.6(3) .
C8 C7 C12 119.6(3) .
C6 C7 C12 119.8(3) .
C1 C2 C3 121.0(3) .
C3 C4 C5 121.1(3) .
O1 C14 O2 124.6(3) .
O1 C14 C13 119.6(3) .
O2 C14 C13 115.8(3) .
O3 C11 N1 120.0(3) .
O3 C11 C1 122.9(3) .
N1 C11 C1 117.1(3) .
N1 C13 C14 114.3(2) .
C4 C3 C2 120.2(3) .
C9 C10 C5 121.7(3) .
C7 C8 C9 120.4(3) .
C10 C9 C8 119.7(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N3 C1V 1.483(4) .
N3 C2V 1.489(4) .
C2V C1V 1.508(4) 3_776
C1V C2V 1.508(4) 3_776
O2 C14 1.257(3) .
N1 C11 1.392(4) .
N1 C12 1.396(4) .
N1 C13 1.456(4) .
O1 C14 1.255(3) .
C6 C7 1.401(4) .
C6 C1 1.412(4) .
C6 C5 1.418(4) .
O3 C11 1.214(4) .
O4 C12 1.220(3) .
C12 C7 1.482(4) .
C5 C10 1.407(4) .
C5 C4 1.409(4) .
C1 C2 1.370(4) .
C1 C11 1.475(4) .
C7 C8 1.365(4) .
C2 C3 1.395(4) .
C4 C3 1.358(4) .
C14 C13 1.508(4) .
C10 C9 1.357(5) .
C8 C9 1.411(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139197343
