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#$Date: 2022-06-30 11:37:50 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276438 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105583.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_8105583
loop_
_publ_author_name
'Jien, Yang'
'Songhua, Chen'
_publ_section_title
;
 Crystal structure of
 2-(4-(dimethylamino)phenyl)-10-methylacridin-9(10H)-one, C22H20N2O
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              187
_journal_page_last               188
_journal_paper_doi               10.1515/ncrs-2018-0310
_journal_volume                  234
_journal_year                    2018
_chemical_formula_sum            'C22 H20 N2 O'
_chemical_formula_weight         328.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.538(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.316(2)
_cell_length_b                   9.247(2)
_cell_length_c                   20.908(5)
_cell_measurement_temperature    173(2)
_cell_volume                     1604.7(6)
_computing_cell_refinement       'CrystalClear [8]'
_computing_data_collection       'CrystalClear [8]'
_computing_data_reduction        'CrystalClear [8]'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELXL-2018/3 [10]'
_computing_structure_refinement  SHELXL-2018/3[10]
_computing_structure_solution    'SHELXS-97 [9]'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9902
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.584
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.216
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0618
_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)+(0.0589P)²+0.6619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2624
_reflns_number_total             2816
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0310_suppl.cif
_cod_data_source_block           sa1788
_cod_original_cell_volume        1604.7(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105583
_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.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_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
O1 O 0.27602(19) 0.18905(18) 0.05131(8) 0.0458(5) Uani 1 1 d . . . . .
N1 N 0.6039(2) 0.51239(18) 0.09521(8) 0.0289(4) Uani 1 1 d . . . . .
N2 N -0.3893(2) 0.4571(2) 0.33768(9) 0.0368(5) Uani 1 1 d . . . . .
C1 C 0.5296(2) 0.2943(2) 0.03534(10) 0.0284(5) Uani 1 1 d . . . . .
C2 C 0.5679(3) 0.1896(2) -0.00961(10) 0.0331(5) Uani 1 1 d . . . . .
H2 H 0.491642 0.116170 -0.021111 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7129(3) 0.1905(2) -0.03744(12) 0.0397(6) Uani 1 1 d . . . . .
H3 H 0.737020 0.119072 -0.068082 0.048 Uiso 1 1 calc R U . . .
C4 C 0.8239(3) 0.2981(3) -0.01990(12) 0.0433(6) Uani 1 1 d . . . . .
H4 H 0.925641 0.297997 -0.038193 0.052 Uiso 1 1 calc R U . . .
C5 C 0.7903(3) 0.4045(2) 0.02316(11) 0.0369(5) Uani 1 1 d . . . . .
H5 H 0.867842 0.477560 0.033671 0.044 Uiso 1 1 calc R U . . .
C6 C 0.6408(2) 0.4056(2) 0.05188(10) 0.0284(5) Uani 1 1 d . . . . .
C7 C 0.4642(2) 0.5036(2) 0.12823(9) 0.0266(5) Uani 1 1 d . . . . .
C8 C 0.3517(2) 0.3921(2) 0.11535(10) 0.0264(5) Uani 1 1 d . . . . .
C9 C 0.3768(2) 0.2843(2) 0.06611(10) 0.0300(5) Uani 1 1 d . . . . .
C10 C 0.4302(2) 0.6051(2) 0.17607(10) 0.0307(5) Uani 1 1 d . . . . .
H10 H 0.503118 0.682343 0.185610 0.037 Uiso 1 1 calc R U . . .
C11 C 0.2930(2) 0.5932(2) 0.20888(10) 0.0306(5) Uani 1 1 d . . . . .
H11 H 0.273100 0.663691 0.240507 0.037 Uiso 1 1 calc R U . . .
C12 C 0.1803(2) 0.4810(2) 0.19766(10) 0.0271(5) Uani 1 1 d . . . . .
C13 C 0.2131(2) 0.3831(2) 0.15025(10) 0.0279(5) Uani 1 1 d . . . . .
H13 H 0.139008 0.306737 0.140898 0.033 Uiso 1 1 calc R U . . .
C14 C 0.0358(2) 0.4683(2) 0.23560(10) 0.0272(5) Uani 1 1 d . . . . .
C15 C 0.0275(2) 0.5330(2) 0.29572(10) 0.0314(5) Uani 1 1 d . . . . .
H15 H 0.119273 0.583131 0.313630 0.038 Uiso 1 1 calc R U . . .
C16 C -0.1090(3) 0.5271(2) 0.33017(10) 0.0318(5) Uani 1 1 d . . . . .
H16 H -0.108455 0.571924 0.371058 0.038 Uiso 1 1 calc R U . . .
C17 C -0.2490(2) 0.4553(2) 0.30546(10) 0.0295(5) Uani 1 1 d . . . . .
C18 C -0.2384(2) 0.3827(2) 0.24710(11) 0.0319(5) Uani 1 1 d . . . . .
H18 H -0.327528 0.327341 0.230334 0.038 Uiso 1 1 calc R U . . .
C19 C -0.1005(2) 0.3901(2) 0.21332(10) 0.0299(5) Uani 1 1 d . . . . .
H19 H -0.098377 0.340266 0.173642 0.036 Uiso 1 1 calc R U . . .
C20 C 0.7136(3) 0.6347(2) 0.10633(12) 0.0378(6) Uani 1 1 d . . . . .
H20B H 0.653322 0.718228 0.121003 0.057 Uiso 1 1 calc R U . . .
H20A H 0.762915 0.659288 0.066367 0.057 Uiso 1 1 calc R U . . .
H20C H 0.797997 0.608639 0.139081 0.057 Uiso 1 1 calc R U . . .
C21 C -0.5216(3) 0.3618(3) 0.31858(11) 0.0382(6) Uani 1 1 d . . . . .
H21A H -0.539146 0.362829 0.271797 0.057 Uiso 1 1 calc R U . . .
H21C H -0.619501 0.394767 0.337953 0.057 Uiso 1 1 calc R U . . .
H21B H -0.495837 0.263207 0.333040 0.057 Uiso 1 1 calc R U . . .
C22 C -0.3912(3) 0.5206(3) 0.40119(11) 0.0406(6) Uani 1 1 d . . . . .
H22A H -0.330894 0.458493 0.432166 0.061 Uiso 1 1 calc R U . . .
H22C H -0.502764 0.529550 0.413253 0.061 Uiso 1 1 calc R U . . .
H22B H -0.341168 0.616538 0.400992 0.061 Uiso 1 1 calc R U . . .
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
C6 N1 C7 120.53(17) . .
C6 N1 C20 119.59(17) . .
C7 N1 C20 119.89(17) . .
C17 N2 C21 120.53(18) . .
C17 N2 C22 120.51(18) . .
C21 N2 C22 116.58(18) . .
C2 C1 C6 119.69(19) . .
C2 C1 C9 119.50(19) . .
C6 C1 C9 120.78(18) . .
C3 C2 C1 121.6(2) . .
C3 C2 H2 119.2 . .
C1 C2 H2 119.2 . .
C2 C3 C4 118.6(2) . .
C2 C3 H3 120.7 . .
C4 C3 H3 120.7 . .
C5 C4 C3 121.8(2) . .
C5 C4 H4 119.1 . .
C3 C4 H4 119.1 . .
C4 C5 C6 120.2(2) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
N1 C6 C1 120.72(18) . .
N1 C6 C5 121.20(19) . .
C1 C6 C5 118.08(19) . .
N1 C7 C8 120.94(18) . .
N1 C7 C10 121.51(18) . .
C8 C7 C10 117.55(19) . .
C13 C8 C7 120.08(19) . .
C13 C8 C9 119.00(18) . .
C7 C8 C9 120.92(18) . .
O1 C9 C8 122.50(19) . .
O1 C9 C1 121.76(19) . .
C8 C9 C1 115.74(18) . .
C11 C10 C7 120.65(19) . .
C11 C10 H10 119.7 . .
C7 C10 H10 119.7 . .
C10 C11 C12 122.76(19) . .
C10 C11 H11 118.6 . .
C12 C11 H11 118.6 . .
C13 C12 C11 116.32(19) . .
C13 C12 C14 122.27(18) . .
C11 C12 C14 121.41(18) . .
C12 C13 C8 122.62(19) . .
C12 C13 H13 118.7 . .
C8 C13 H13 118.7 . .
C15 C14 C19 115.85(19) . .
C15 C14 C12 122.25(18) . .
C19 C14 C12 121.90(19) . .
C16 C15 C14 122.66(19) . .
C16 C15 H15 118.7 . .
C14 C15 H15 118.7 . .
C15 C16 C17 120.9(2) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
N2 C17 C18 122.10(19) . .
N2 C17 C16 121.19(19) . .
C18 C17 C16 116.71(19) . .
C19 C18 C17 121.33(19) . .
C19 C18 H18 119.3 . .
C17 C18 H18 119.3 . .
C18 C19 C14 122.3(2) . .
C18 C19 H19 118.8 . .
C14 C19 H19 118.8 . .
N1 C20 H20B 109.5 . .
N1 C20 H20A 109.5 . .
H20B C20 H20A 109.5 . .
N1 C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
N2 C21 H21A 109.5 . .
N2 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
N2 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
H21C C21 H21B 109.5 . .
N2 C22 H22A 109.5 . .
N2 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
N2 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
H22C C22 H22B 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C9 1.242(2) .
N1 C6 1.387(3) .
N1 C7 1.390(3) .
N1 C20 1.463(3) .
N2 C17 1.382(3) .
N2 C21 1.447(3) .
N2 C22 1.453(3) .
C1 C2 1.400(3) .
C1 C6 1.413(3) .
C1 C9 1.462(3) .
C2 C3 1.370(3) .
C2 H2 0.9500 .
C3 C4 1.391(3) .
C3 H3 0.9500 .
C4 C5 1.374(3) .
C4 H4 0.9500 .
C5 C6 1.414(3) .
C5 H5 0.9500 .
C7 C8 1.407(3) .
C7 C10 1.413(3) .
C8 C13 1.404(3) .
C8 C9 1.457(3) .
C10 C11 1.372(3) .
C10 H10 0.9500 .
C11 C12 1.408(3) .
C11 H11 0.9500 .
C12 C13 1.382(3) .
C12 C14 1.485(3) .
C13 H13 0.9500 .
C14 C15 1.398(3) .
C14 C19 1.400(3) .
C15 C16 1.382(3) .
C15 H15 0.9500 .
C16 C17 1.411(3) .
C16 H16 0.9500 .
C17 C18 1.400(3) .
C18 C19 1.385(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 H20B 0.9800 .
C20 H20A 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21C 0.9800 .
C21 H21B 0.9800 .
C22 H22A 0.9800 .
C22 H22C 0.9800 .
C22 H22B 0.9800 .
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
C6 C1 C2 C3 1.2(3) . . . .
C9 C1 C2 C3 -176.9(2) . . . .
C1 C2 C3 C4 0.4(3) . . . .
C2 C3 C4 C5 -1.5(4) . . . .
C3 C4 C5 C6 1.1(4) . . . .
C7 N1 C6 C1 6.8(3) . . . .
C20 N1 C6 C1 -173.50(19) . . . .
C7 N1 C6 C5 -173.03(19) . . . .
C20 N1 C6 C5 6.7(3) . . . .
C2 C1 C6 N1 178.53(19) . . . .
C9 C1 C6 N1 -3.4(3) . . . .
C2 C1 C6 C5 -1.7(3) . . . .
C9 C1 C6 C5 176.39(19) . . . .
C4 C5 C6 N1 -179.6(2) . . . .
C4 C5 C6 C1 0.5(3) . . . .
C6 N1 C7 C8 -4.4(3) . . . .
C20 N1 C7 C8 175.82(19) . . . .
C6 N1 C7 C10 175.15(18) . . . .
C20 N1 C7 C10 -4.6(3) . . . .
N1 C7 C8 C13 178.51(18) . . . .
C10 C7 C8 C13 -1.1(3) . . . .
N1 C7 C8 C9 -1.2(3) . . . .
C10 C7 C8 C9 179.15(18) . . . .
C13 C8 C9 O1 4.0(3) . . . .
C7 C8 C9 O1 -176.2(2) . . . .
C13 C8 C9 C1 -175.44(18) . . . .
C7 C8 C9 C1 4.3(3) . . . .
C2 C1 C9 O1 -3.4(3) . . . .
C6 C1 C9 O1 178.5(2) . . . .
C2 C1 C9 C8 176.02(18) . . . .
C6 C1 C9 C8 -2.0(3) . . . .
N1 C7 C10 C11 -178.91(19) . . . .
C8 C7 C10 C11 0.7(3) . . . .
C7 C10 C11 C12 0.5(3) . . . .
C10 C11 C12 C13 -1.3(3) . . . .
C10 C11 C12 C14 177.82(19) . . . .
C11 C12 C13 C8 0.9(3) . . . .
C14 C12 C13 C8 -178.24(18) . . . .
C7 C8 C13 C12 0.3(3) . . . .
C9 C8 C13 C12 -179.95(19) . . . .
C13 C12 C14 C15 158.1(2) . . . .
C11 C12 C14 C15 -21.0(3) . . . .
C13 C12 C14 C19 -21.6(3) . . . .
C11 C12 C14 C19 159.26(19) . . . .
C19 C14 C15 C16 -3.1(3) . . . .
C12 C14 C15 C16 177.1(2) . . . .
C14 C15 C16 C17 -0.6(3) . . . .
C21 N2 C17 C18 11.7(3) . . . .
C22 N2 C17 C18 173.6(2) . . . .
C21 N2 C17 C16 -168.3(2) . . . .
C22 N2 C17 C16 -6.4(3) . . . .
C15 C16 C17 N2 -175.6(2) . . . .
C15 C16 C17 C18 4.4(3) . . . .
N2 C17 C18 C19 175.6(2) . . . .
C16 C17 C18 C19 -4.4(3) . . . .
C17 C18 C19 C14 0.7(3) . . . .
C15 C14 C19 C18 3.0(3) . . . .
C12 C14 C19 C18 -177.19(19) . . . .
