#------------------------------------------------------------------------------
#$Date: 2024-02-13 04:27:39 +0200 (Tue, 13 Feb 2024) $
#$Revision: 289799 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/81/7248127.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_7248127
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'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-01-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-01-23 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_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_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           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11578
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         48.76
_diffrn_reflns_theta_min         2.30
_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             260.394
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.178
_refine_diff_density_max         0.3603
_refine_diff_density_min         -0.2864
_refine_diff_density_rms         0.0366
_refine_ls_d_res_high            0.4726
_refine_ls_d_res_low             8.8456
_refine_ls_goodness_of_fit_ref   1.1780
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     193
_refine_ls_number_reflns         11578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1780
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0139
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0083P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0387
_refine_ls_wR_factor_ref         0.0426
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              16
_reflns_limit_k_min              -18
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                9998
_reflns_number_total             11578
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ra08081a2.cif
_cod_data_source_block           9AA
_cod_database_code               7248127
_olex2_refinement_description
;
1. Others
 Fixed U11: H16(0.041734) H14(0.028708) H13(0.031712) H12(0.024091)
 H11(0.030177) H5(0.033814) H2(0.025258) H9(0.022299) H4(0.038171) H8(0.027659)
 H10(0.032882) H3(0.024341) H15(0.045892)
 Fixed U12: H16(-0.007636) H14(0.005661) H13(0.00867) H12(0.011761)
 H11(0.007465) H5(0.004735) H2(0.006579) H9(0.011721) H4(0.005164) H8(0.006232)
 H10(0.009835) H3(0.008861) H15(-0.014892)
 Fixed U13: H16(0.003145) H14(-0.008295) H13(-0.003699) H12(-0.004746) H11(-
 0.00713) H5(-0.00735) H2(-0.00677) H9(-0.001557) H4(0.005896) H8(-0.01045)
 H10(0.00344) H3(0.004083) H15(0.001002)
 Fixed U22: H16(0.049776) H14(0.039354) H13(0.039277) H12(0.03881)
 H11(0.041415) H5(0.043915) H2(0.041345) H9(0.041277) H4(0.044175) H8(0.042375)
 H10(0.040685) H3(0.041361) H15(0.042462)
 Fixed U23: H16(-0.017851) H14(-0.002744) H13(-0.009855) H12(-0.005324) H11(-
 0.005311) H5(-0.003708) H2(-0.004159) H9(-0.004276) H4(-0.00824) H8(-0.003528)
 H10(-0.008475) H3(-0.006095) H15(-0.009608)
 Fixed U33: H16(0.03108) H14(0.01886) H13(0.01935) H12(0.0271) H11(0.01866)
 H5(0.01874) H2(0.02376) H9(0.03529) H4(0.01933) H8(0.02451) H10(0.02294)
 H3(0.0321) H15(0.03117)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_refinement_flags_posn
Cl1 Cl 1.061866(6) 0.731645(5) 0.897100(4) 0.015108(11) Uani 1.000000 .
O1 O 0.92282(2) 0.330530(19) 0.802027(15) 0.01767(2) Uani 1.000000 .
N2 N 0.641137(19) 0.241262(18) 0.559012(15) 0.012603(19) Uani 1.000000 .
N1 N 0.22826(2) 0.09310(2) 0.186825(16) 0.01493(2) Uani 1.000000 .
C13 C 0.36067(2) 0.140382(19) 0.306183(16) 0.01098(2) Uani 1.000000 .
C12 C 0.50519(2) 0.064885(19) 0.295390(16) 0.01101(2) Uani 1.000000 .
C1 C 0.36349(2) 0.268815(19) 0.449626(16) 0.01112(2) Uani 1.000000 .
C11 C 0.51531(2) -0.06187(2) 0.158645(18) 0.01341(2) Uani 1.000000 .
C6 C 0.50640(2) 0.315335(19) 0.574387(16) 0.01157(2) Uani 1.000000 .
C5 C 0.51107(2) 0.43913(2) 0.717547(18) 0.01455(2) Uani 1.000000 .
C2 C 0.22516(2) 0.34834(2) 0.471496(18) 0.01358(2) Uani 1.000000 .
C9 C 0.79742(2) -0.07012(2) 0.28315(2) 0.01529(2) Uani 1.000000 .
C4 C 0.37419(3) 0.51279(2) 0.734866(19) 0.01592(2) Uani 1.000000 .
C8 C 0.79128(2) 0.05175(2) 0.417264(19) 0.01402(2) Uani 1.000000 .
C7 C 0.64497(2) 0.120883(19) 0.424993(17) 0.01136(2) Uani 1.000000 .
C10 C 0.65815(2) -0.12770(2) 0.15271(2) 0.01515(2) Uani 1.000000 .
C3 C 0.23016(2) 0.46736(2) 0.61117(2) 0.01559(2) Uani 1.000000 .
H16 H 0.9221(9) 0.3097(8) 0.8911(8) 0.040863 Uani 1.000000 .
H14 H 0.7434(7) 0.2773(7) 0.6552(6) 0.028974 Uani 1.000000 .
H13 H 0.2123(8) -0.0097(7) 0.0884(6) 0.030113 Uani 1.000000 .
H12 H 0.1323(7) 0.1546(7) 0.1895(6) 0.030000 Uani 1.000000 .
H11 H 0.4085(7) -0.1085(6) 0.0578(5) 0.030084 Uani 1.000000 .
H5 H 0.6239(7) 0.4737(7) 0.8094(5) 0.032156 Uani 1.000000 .
H2 H 0.1138(6) 0.3150(6) 0.3769(5) 0.030121 Uani 1.000000 .
H9 H 0.9082(7) -0.1239(7) 0.2765(6) 0.032955 Uani 1.000000 .
H4 H 0.3739(7) 0.6041(7) 0.8425(5) 0.033892 Uani 1.000000 .
H8 H 0.8970(7) 0.0989(6) 0.5169(6) 0.031514 Uani 1.000000 .
H10 H 0.6658(7) -0.2252(7) 0.0485(5) 0.032169 Uani 1.000000 .
H3 H 0.1255(7) 0.5292(6) 0.6287(6) 0.032601 Uani 1.000000 .
H15 H 0.9814(9) 0.4536(8) 0.8361(7) 0.039842 Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_source
H 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
O 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
C 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
Cl 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
N 'DiSCaMB, J. Appl. Cryst. 2018, DOI:10.1107/S1600576717015825'
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
H15 O1 H16 105.7(5) . . ?
C7 N2 C6 122.289(13) . . ?
H14 N2 C6 118.1(3) . . ?
H14 N2 C7 119.6(3) . . ?
H13 N1 C13 122.3(3) . . ?
H12 N1 C13 121.7(3) . . ?
H12 N1 H13 116.0(4) . . ?
C12 C13 N1 120.780(13) . . ?
C1 C13 N1 120.763(14) . . ?
C1 C13 C12 118.457(13) . . ?
C11 C12 C13 122.712(13) . . ?
C7 C12 C13 118.871(13) . . ?
C7 C12 C11 118.405(13) . . ?
C6 C1 C13 119.133(13) . . ?
C2 C1 C13 122.391(13) . . ?
C2 C1 C6 118.461(13) . . ?
C10 C11 C12 120.730(14) . . ?
H11 C11 C12 119.8(3) . . ?
H11 C11 C10 119.4(3) . . ?
C1 C6 N2 120.498(13) . . ?
C5 C6 N2 119.103(14) . . ?
C5 C6 C1 120.399(14) . . ?
C4 C5 C6 119.578(15) . . ?
H5 C5 C6 118.3(3) . . ?
H5 C5 C4 122.1(3) . . ?
C3 C2 C1 120.700(15) . . ?
H2 C2 C1 119.9(2) . . ?
H2 C2 C3 119.4(2) . . ?
C10 C9 C8 120.434(15) . . ?
H9 C9 C8 120.3(3) . . ?
H9 C9 C10 119.2(3) . . ?
C3 C4 C5 120.677(15) . . ?
H4 C4 C5 120.6(3) . . ?
H4 C4 C3 118.8(3) . . ?
C7 C8 C9 119.899(14) . . ?
H8 C8 C9 121.5(3) . . ?
H8 C8 C7 118.5(3) . . ?
C12 C7 N2 120.733(14) . . ?
C8 C7 N2 119.014(13) . . ?
C8 C7 C12 120.252(14) . . ?
C9 C10 C11 120.278(15) . . ?
H10 C10 C11 120.9(3) . . ?
H10 C10 C9 118.8(3) . . ?
C4 C3 C2 120.181(16) . . ?
H3 C3 C2 121.2(3) . . ?
H3 C3 C4 118.6(3) . . ?
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 H16 0.948(7) . ?
O1 H15 0.973(6) . ?
N2 C6 1.3607(2) . ?
N2 C7 1.3605(2) . ?
N2 H14 1.050(5) . ?
N1 C13 1.3233(2) . ?
N1 H13 1.021(5) . ?
N1 H12 1.022(5) . ?
C13 C12 1.4370(2) . ?
C13 C1 1.4380(2) . ?
C12 C11 1.4201(2) . ?
C12 C7 1.4110(2) . ?
C1 C6 1.4098(2) . ?
C1 C2 1.4187(2) . ?
C11 C10 1.3730(2) . ?
C11 H11 1.085(4) . ?
C6 C5 1.4149(2) . ?
C5 C4 1.3742(3) . ?
C5 H5 1.075(5) . ?
C2 C3 1.3733(2) . ?
C2 H2 1.088(5) . ?
C9 C8 1.3729(3) . ?
C9 C10 1.4120(3) . ?
C9 H9 1.079(5) . ?
C4 C3 1.4105(3) . ?
C4 H4 1.066(4) . ?
C8 C7 1.4153(2) . ?
C8 H8 1.072(5) . ?
C10 H10 1.085(5) . ?
C3 H3 1.083(5) . ?
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 C1 C13 0.771(17) . . . . ?
N2 C6 C1 C2 179.406(15) . . . . ?
N2 C6 C5 C4 -179.002(16) . . . . ?
N2 C7 C12 C13 1.577(17) . . . . ?
N2 C7 C12 C11 -179.590(15) . . . . ?
N2 C7 C8 C9 179.862(16) . . . . ?
N1 C13 C12 C11 0.339(19) . . . . ?
N1 C13 C12 C7 179.119(15) . . . . ?
N1 C13 C1 C6 179.740(15) . . . . ?
N1 C13 C1 C2 1.161(18) . . . . ?
C13 C12 C11 C10 178.517(16) . . . . ?
C13 C12 C7 C8 -178.640(14) . . . . ?
C13 C1 C6 C5 -178.899(15) . . . . ?
C13 C1 C2 C3 178.342(16) . . . . ?
C12 C11 C10 C9 0.075(19) . . . . ?
C12 C7 C8 C9 0.076(17) . . . . ?
C1 C6 C5 C4 0.673(17) . . . . ?
C1 C2 C3 C4 0.349(19) . . . . ?
C11 C10 C9 C8 0.20(2) . . . . ?
C6 C5 C4 C3 -0.574(19) . . . . ?
C5 C4 C3 C2 0.07(2) . . . . ?
