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#$Date: 2023-04-04 13:11:04 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282322 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/63/7246324.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_7246324
loop_
_publ_author_name
'Sendh, Jagajiban'
'Baruah, Jubaraj B.'
_publ_section_title
;
 Polymorphs, ionic cocrystal and inclusion complex of
 N-amino-1,8-naphthalimide
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1928
_journal_page_last               1940
_journal_paper_doi               10.1039/D2CE01673G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C12 H11 N3 O6'
_chemical_formula_weight         293.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-04-26 deposited with the CCDC.	2023-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                98.26(2)
_cell_angle_beta                 94.33(2)
_cell_angle_gamma                93.17(2)
_cell_formula_units_Z            2
_cell_length_a                   6.983(4)
_cell_length_b                   8.788(5)
_cell_length_c                   10.103(6)
_cell_measurement_reflns_used    2323
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.35
_cell_volume                     610.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6767
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.554
_diffrn_reflns_theta_min         2.875
_exptl_absorpt_coefficient_mu    0.131
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0505P)²+0.0665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1643
_reflns_number_total             2961
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01673g2.cif
_cod_data_source_block           NO3Polymorph1
_cod_depositor_comments
'Adding full bibliography for 7246323--7246328.cif.'
_cod_database_code               7246324
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.9554(2) 0.17198(17) 0.98632(16) 0.0492(4) Uani 1 1 d . . . . .
O1 O 0.6271(2) 0.06283(18) 0.36280(15) 0.0495(4) Uani 1 1 d . . . . .
O2 O 0.7102(2) 0.46384(18) 0.13759(15) 0.0547(5) Uani 1 1 d . . . . .
O4 O 0.7338(2) 0.01788(19) 0.86981(16) 0.0563(5) Uani 1 1 d . . . . .
O3 O 1.0126(2) 0.0473(2) 0.79483(17) 0.0643(5) Uani 1 1 d . . . . .
N1 N 0.6749(2) 0.27066(19) 0.25881(16) 0.0372(4) Uani 1 1 d . . . . .
N3 N 0.8999(3) 0.0773(2) 0.8815(2) 0.0433(5) Uani 1 1 d . . . . .
N2 N 0.6432(3) 0.1679(2) 0.13564(18) 0.0442(5) Uani 1 1 d . . . . .
H2A H 0.624339 0.074486 0.152098 0.053 Uiso 1 1 d R U . . .
H2B H 0.542845 0.191645 0.089040 0.053 Uiso 1 1 d R U . . .
C1 C 0.6611(3) 0.2002(3) 0.3752(2) 0.0363(5) Uani 1 1 d . . . . .
C12 C 0.7127(3) 0.4259(2) 0.2485(2) 0.0380(5) Uani 1 1 d . . . . .
C2 C 0.6935(3) 0.3072(2) 0.5008(2) 0.0355(5) Uani 1 1 d . . . . .
C11 C 0.7405(2) 0.4655(2) 0.4987(2) 0.0358(5) Uani 1 1 d . . . . .
C10 C 0.7508(3) 0.5267(2) 0.3770(2) 0.0364(5) Uani 1 1 d . . . . .
C6 C 0.7760(3) 0.5658(3) 0.6221(2) 0.0437(6) Uani 1 1 d . . . . .
C3 C 0.6790(3) 0.2518(3) 0.6213(2) 0.0456(6) Uani 1 1 d . . . . .
H3 H 0.646203 0.147916 0.621885 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7977(3) 0.6812(3) 0.3792(3) 0.0481(6) Uani 1 1 d . . . . .
H9 H 0.805193 0.720451 0.298880 0.058 Uiso 1 1 calc R U . . .
C4 C 0.7140(3) 0.3526(3) 0.7421(2) 0.0541(7) Uani 1 1 d . . . . .
H4 H 0.703164 0.315035 0.822956 0.065 Uiso 1 1 calc R U . . .
C5 C 0.7635(3) 0.5040(3) 0.7432(2) 0.0528(6) Uani 1 1 d . . . . .
H5 H 0.789622 0.568401 0.824862 0.063 Uiso 1 1 calc R U . . .
C8 C 0.8341(3) 0.7796(3) 0.5011(3) 0.0565(7) Uani 1 1 d . . . . .
H8 H 0.865731 0.883915 0.501511 0.068 Uiso 1 1 calc R U . . .
C7 C 0.8233(3) 0.7232(3) 0.6198(3) 0.0551(7) Uani 1 1 d . . . . .
H7 H 0.847556 0.789848 0.700302 0.066 Uiso 1 1 calc R U . . .
O6 O 0.3571(2) 0.2463(2) 0.97004(18) 0.0650(5) Uani 1 1 d G . . . .
H6A H 0.239479 0.214060 0.966196 0.098 Uiso 1 1 d G U . . .
H6B H 0.355031 0.330901 0.938713 0.098 Uiso 1 1 d G U . . .
H2C H 0.765(4) 0.173(3) 0.084(3) 0.077(8) 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'
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
C12 N1 C1 128.98(18) . . ?
C12 N1 N2 116.21(16) . . ?
C1 N1 N2 114.80(17) . . ?
O3 N3 O4 122.0(2) . . ?
O3 N3 O5 119.29(18) . . ?
O4 N3 O5 118.73(19) . . ?
N1 N2 H2A 109.5 . . ?
N1 N2 H2B 110.0 . . ?
H2A N2 H2B 108.9 . . ?
N1 N2 H2C 108.7(14) . . ?
H2A N2 H2C 107.9 . . ?
H2B N2 H2C 111.6 . . ?
O1 C1 N1 118.9(2) . . ?
O1 C1 C2 126.99(19) . . ?
N1 C1 C2 114.14(18) . . ?
O2 C12 N1 118.6(2) . . ?
O2 C12 C10 126.8(2) . . ?
N1 C12 C10 114.57(17) . . ?
C3 C2 C11 120.5(2) . . ?
C3 C2 C1 119.3(2) . . ?
C11 C2 C1 120.17(18) . . ?
C2 C11 C6 118.91(19) . . ?
C2 C11 C10 121.9(2) . . ?
C6 C11 C10 119.1(2) . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 C12 119.7(2) . . ?
C11 C10 C12 120.12(19) . . ?
C7 C6 C5 122.4(2) . . ?
C7 C6 C11 118.8(2) . . ?
C5 C6 C11 118.8(2) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C8 C9 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
H6A O6 H6B 104.5 . . ?
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
O5 N3 1.270(2) . ?
O1 C1 1.204(2) . ?
O2 C12 1.214(2) . ?
O4 N3 1.235(2) . ?
O3 N3 1.231(2) . ?
N1 C12 1.395(3) . ?
N1 C1 1.413(3) . ?
N1 N2 1.423(2) . ?
N2 H2A 0.8661 . ?
N2 H2B 0.8664 . ?
N2 H2C 1.03(3) . ?
C1 C2 1.461(3) . ?
C12 C10 1.460(3) . ?
C2 C3 1.383(3) . ?
C2 C11 1.415(3) . ?
C11 C6 1.416(3) . ?
C11 C10 1.416(3) . ?
C10 C9 1.375(3) . ?
C6 C7 1.408(3) . ?
C6 C5 1.415(3) . ?
C3 C4 1.398(3) . ?
C3 H3 0.9300 . ?
C9 C8 1.397(3) . ?
C9 H9 0.9300 . ?
C4 C5 1.355(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C8 C7 1.368(3) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
O6 H6A 0.8502 . ?
O6 H6B 0.8495 . ?
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
C12 N1 C1 O1 -179.96(17) . . . . ?
N2 N1 C1 O1 0.9(2) . . . . ?
C12 N1 C1 C2 -0.7(3) . . . . ?
N2 N1 C1 C2 -179.85(15) . . . . ?
C1 N1 C12 O2 -176.86(18) . . . . ?
N2 N1 C12 O2 2.3(3) . . . . ?
C1 N1 C12 C10 2.8(3) . . . . ?
N2 N1 C12 C10 -178.01(15) . . . . ?
O1 C1 C2 C3 -2.3(3) . . . . ?
N1 C1 C2 C3 178.46(16) . . . . ?
O1 C1 C2 C11 177.19(18) . . . . ?
N1 C1 C2 C11 -2.0(2) . . . . ?
C3 C2 C11 C6 1.1(3) . . . . ?
C1 C2 C11 C6 -178.39(16) . . . . ?
C3 C2 C11 C10 -178.09(17) . . . . ?
C1 C2 C11 C10 2.4(3) . . . . ?
C2 C11 C10 C9 -179.78(17) . . . . ?
C6 C11 C10 C9 1.0(3) . . . . ?
C2 C11 C10 C12 -0.1(3) . . . . ?
C6 C11 C10 C12 -179.30(16) . . . . ?
O2 C12 C10 C9 -3.0(3) . . . . ?
N1 C12 C10 C9 177.35(17) . . . . ?
O2 C12 C10 C11 177.33(19) . . . . ?
N1 C12 C10 C11 -2.3(2) . . . . ?
C2 C11 C6 C7 179.83(17) . . . . ?
C10 C11 C6 C7 -0.9(3) . . . . ?
C2 C11 C6 C5 0.1(3) . . . . ?
C10 C11 C6 C5 179.37(17) . . . . ?
C11 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C4 178.56(18) . . . . ?
C11 C10 C9 C8 -0.5(3) . . . . ?
C12 C10 C9 C8 179.79(18) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 1.8(3) . . . . ?
C7 C6 C5 C4 178.72(19) . . . . ?
C11 C6 C5 C4 -1.6(3) . . . . ?
C10 C9 C8 C7 -0.1(3) . . . . ?
C9 C8 C7 C6 0.1(3) . . . . ?
C5 C6 C7 C8 -179.93(19) . . . . ?
C11 C6 C7 C8 0.4(3) . . . . ?
