#------------------------------------------------------------------------------
#$Date: 2024-02-13 03:27:39 +0100 (Tue 13 de Feb de 2024) $
#$Revision: 289799 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/81/7248128.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_7248128
loop_
_publ_author_name
'Pawlędzio, Sylwia'
'Ziemniak, Marcin'
'Trzybiński, Damian'
'Arhangelskis, Mihails'
'Makal, Anna'
'Woźniak, Krzysztof'
_publ_section_title
;
 Influence of N-protonation on electronic properties of acridine
 derivatives by quantum crystallography
;
_journal_issue                   8
_journal_name_full               'RSC Advances'
_journal_page_first              5340
_journal_page_last               5350
_journal_paper_doi               10.1039/D3RA08081A
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'Cl, H2 O, C13 H11 N2'
_chemical_formula_sum            'C13 H13 Cl N2 O'
_chemical_formula_weight         248.70
_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   difmap
_audit_creation_date             2023-06-15
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.11.02 svn.ra8b101fa for OlexSys, GUI svn.r6635)
;
_audit_update_record
;
2023-06-15 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                111.057(2)
_cell_angle_beta                 96.558(2)
_cell_angle_gamma                104.436(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7880(5)
_cell_length_b                   8.7699(5)
_cell_length_c                   9.7291(6)
_cell_measurement_reflns_used    9427
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      48.63
_cell_measurement_theta_min      2.30
_cell_volume                     585.08(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_number            11565
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         48.758
_diffrn_reflns_theta_min         2.302
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0454 before and 0.0398 after correction.
The Ratio of minimum to maximum transmission is 0.9672.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       prism
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         11565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0213
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0446P)²+0.0155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9961
_reflns_number_total             11565
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra08081a2.cif
_cod_data_source_block           9aa
_cod_database_code               7248128
_shelx_shelxl_version_number     2019/2
_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.
;
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cl1 Cl 1.06187(2) 0.73162(2) 0.89708(2) 0.01519(2) Uani 1 1 d . . . . .
O1 O 0.92275(4) 0.33028(3) 0.80177(3) 0.01772(4) Uani 1 1 d . . . . .
N2 N 0.64113(3) 0.24125(3) 0.55901(2) 0.01271(3) Uani 1 1 d . . . . .
N1 N 0.22827(3) 0.09312(3) 0.18680(3) 0.01505(3) Uani 1 1 d . . . . .
C13 C 0.36070(3) 0.14039(3) 0.30623(3) 0.01111(3) Uani 1 1 d . . . . .
C12 C 0.50521(3) 0.06493(3) 0.29538(3) 0.01118(3) Uani 1 1 d . . . . .
C1 C 0.36346(3) 0.26882(3) 0.44959(3) 0.01128(3) Uani 1 1 d . . . . .
C11 C 0.51534(4) -0.06182(3) 0.15867(3) 0.01348(3) Uani 1 1 d . . . . .
C6 C 0.50640(3) 0.31535(3) 0.57437(3) 0.01175(3) Uani 1 1 d . . . . .
C5 C 0.51104(4) 0.43916(4) 0.71756(3) 0.01471(4) Uani 1 1 d . . . . .
C2 C 0.22512(4) 0.34832(4) 0.47151(3) 0.01368(3) Uani 1 1 d . . . . .
C9 C 0.79732(4) -0.07015(4) 0.28310(3) 0.01545(4) Uani 1 1 d . . . . .
C4 C 0.37422(4) 0.51274(4) 0.73482(3) 0.01605(4) Uani 1 1 d . . . . .
C8 C 0.79129(4) 0.05174(4) 0.41722(3) 0.01418(4) Uani 1 1 d . . . . .
C7 C 0.64501(3) 0.12080(3) 0.42499(3) 0.01149(3) Uani 1 1 d . . . . .
C10 C 0.65822(4) -0.12766(4) 0.15269(3) 0.01526(4) Uani 1 1 d . . . . .
C3 C 0.23010(4) 0.46736(4) 0.61112(3) 0.01569(4) Uani 1 1 d . . . . .
H1C H 0.9156(15) 0.3112(14) 0.8742(13) 0.048(3) Uiso 1 1 d . . . . .
H2 H 0.7259(15) 0.2703(15) 0.6444(14) 0.055(3) Uiso 1 1 d . . . . .
H1A H 0.2189(13) 0.0015(12) 0.1006(11) 0.037(2) Uiso 1 1 d . . . . .
H1B H 0.1434(14) 0.1456(13) 0.1925(12) 0.044(3) Uiso 1 1 d . . . . .
H11 H 0.4280(12) -0.1038(12) 0.0683(11) 0.032(2) Uiso 1 1 d . . . . .
H5 H 0.6097(12) 0.4653(12) 0.8023(11) 0.031(2) Uiso 1 1 d . . . . .
H2A H 0.1258(14) 0.3178(13) 0.3842(12) 0.042(2) Uiso 1 1 d . . . . .
H9 H 0.8940(13) -0.1218(12) 0.2781(11) 0.038(2) Uiso 1 1 d . . . . .
H4 H 0.3710(11) 0.5915(11) 0.8338(10) 0.0267(19) Uiso 1 1 d . . . . .
H8 H 0.8859(12) 0.0917(11) 0.5122(10) 0.0276(19) Uiso 1 1 d . . . . .
H10 H 0.6660(11) -0.2184(11) 0.0550(10) 0.0270(19) Uiso 1 1 d . . . . .
H3 H 0.1339(13) 0.5209(13) 0.6267(12) 0.039(2) Uiso 1 1 d . . . . .
H1D H 0.9722(13) 0.4386(13) 0.8298(12) 0.040(2) 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'
Cl Cl 0.1484 0.1585 '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
H1C O1 H1D 108.4(10) . . ?
C6 N2 C7 122.31(2) . . ?
C6 N2 H2 117.0(7) . . ?
C7 N2 H2 120.6(7) . . ?
C13 N1 H1A 119.9(6) . . ?
C13 N1 H1B 120.3(7) . . ?
H1A N1 H1B 119.6(9) . . ?
N1 C13 C12 120.75(2) . . ?
N1 C13 C1 120.74(2) . . ?
C12 C13 C1 118.50(2) . . ?
C11 C12 C13 122.74(2) . . ?
C7 C12 C13 118.89(2) . . ?
C7 C12 C11 118.36(2) . . ?
C6 C1 C13 119.10(2) . . ?
C6 C1 C2 118.45(2) . . ?
C2 C1 C13 122.43(2) . . ?
C12 C11 H11 122.8(6) . . ?
C10 C11 C12 120.76(2) . . ?
C10 C11 H11 116.4(6) . . ?
N2 C6 C1 120.50(2) . . ?
N2 C6 C5 119.11(2) . . ?
C1 C6 C5 120.39(2) . . ?
C6 C5 H5 118.2(6) . . ?
C4 C5 C6 119.57(3) . . ?
C4 C5 H5 122.2(6) . . ?
C1 C2 H2A 118.9(6) . . ?
C3 C2 C1 120.73(2) . . ?
C3 C2 H2A 120.4(6) . . ?
C8 C9 C10 120.48(2) . . ?
C8 C9 H9 120.3(6) . . ?
C10 C9 H9 119.2(6) . . ?
C5 C4 C3 120.72(3) . . ?
C5 C4 H4 120.4(5) . . ?
C3 C4 H4 118.7(5) . . ?
C9 C8 C7 119.88(2) . . ?
C9 C8 H8 122.1(5) . . ?
C7 C8 H8 118.0(5) . . ?
N2 C7 C12 120.68(2) . . ?
N2 C7 C8 119.05(2) . . ?
C12 C7 C8 120.28(2) . . ?
C11 C10 C9 120.24(3) . . ?
C11 C10 H10 121.0(5) . . ?
C9 C10 H10 118.7(5) . . ?
C2 C3 C4 120.13(3) . . ?
C2 C3 H3 120.8(6) . . ?
C4 C3 H3 119.1(6) . . ?
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 H1C 0.786(12) . ?
O1 H1D 0.856(10) . ?
N2 C6 1.3608(3) . ?
N2 C7 1.3609(3) . ?
N2 H2 0.911(12) . ?
N1 C13 1.3239(3) . ?
N1 H1A 0.909(10) . ?
N1 H1B 0.891(11) . ?
C13 C12 1.4367(3) . ?
C13 C1 1.4376(3) . ?
C12 C11 1.4199(3) . ?
C12 C7 1.4114(3) . ?
C1 C6 1.4101(3) . ?
C1 C2 1.4187(4) . ?
C11 C10 1.3733(4) . ?
C11 H11 0.937(9) . ?
C6 C5 1.4152(4) . ?
C5 C4 1.3733(4) . ?
C5 H5 0.977(9) . ?
C2 C3 1.3731(4) . ?
C2 H2A 0.987(10) . ?
C9 C8 1.3727(4) . ?
C9 C10 1.4112(4) . ?
C9 H9 0.969(10) . ?
C4 C3 1.4111(4) . ?
C4 H4 0.970(9) . ?
C8 C7 1.4146(4) . ?
C8 H8 1.002(9) . ?
C10 H10 1.017(9) . ?
C3 H3 0.977(10) . ?
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
N2 C6 C5 C4 -178.99(2) . . . . ?
N1 C13 C12 C11 0.28(4) . . . . ?
N1 C13 C12 C7 179.14(2) . . . . ?
N1 C13 C1 C6 179.77(2) . . . . ?
N1 C13 C1 C2 1.21(4) . . . . ?
C13 C12 C11 C10 178.53(2) . . . . ?
C13 C12 C7 N2 1.50(4) . . . . ?
C13 C12 C7 C8 -178.63(2) . . . . ?
C13 C1 C6 N2 0.76(4) . . . . ?
C13 C1 C6 C5 -178.88(2) . . . . ?
C13 C1 C2 C3 178.34(2) . . . . ?
C12 C13 C1 C6 -0.44(3) . . . . ?
C12 C13 C1 C2 -178.99(2) . . . . ?
C12 C11 C10 C9 0.14(4) . . . . ?
C1 C13 C12 C11 -179.52(2) . . . . ?
C1 C13 C12 C7 -0.66(3) . . . . ?
C1 C6 C5 C4 0.66(4) . . . . ?
C1 C2 C3 C4 0.32(4) . . . . ?
C11 C12 C7 N2 -179.60(2) . . . . ?
C11 C12 C7 C8 0.27(4) . . . . ?
C6 N2 C7 C12 -1.22(4) . . . . ?
C6 N2 C7 C8 178.91(2) . . . . ?
C6 C1 C2 C3 -0.22(4) . . . . ?
C6 C5 C4 C3 -0.57(4) . . . . ?
C5 C4 C3 C2 0.08(5) . . . . ?
C2 C1 C6 N2 179.37(2) . . . . ?
C2 C1 C6 C5 -0.27(4) . . . . ?
C9 C8 C7 N2 179.86(2) . . . . ?
C9 C8 C7 C12 -0.01(4) . . . . ?
C8 C9 C10 C11 0.13(4) . . . . ?
C7 N2 C6 C1 0.06(4) . . . . ?
C7 N2 C6 C5 179.71(2) . . . . ?
C7 C12 C11 C10 -0.34(4) . . . . ?
C10 C9 C8 C7 -0.19(4) . . . . ?
