#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014681.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2014681
loop_
_publ_author_name
'Sikorski, Artur'
'Krzymiński, Karol'
'Konitz, Antoni'
'Błażejowski, Jerzy'
_publ_section_title
;
 2-Ethylphenyl acridine-9-carboxylate and 2,5-dimethylphenyl
 acridine-9-carboxylate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o50
_journal_page_last               o52
_journal_paper_doi               10.1107/S0108270104030537
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C22 H17 N O2'
_chemical_formula_moiety         'C22 H17 N O2'
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.37
_chemical_name_systematic
;
2,5-dimethylphenyl acridine-9-carboxylate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 115.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.769(2)
_cell_length_b                   15.404(3)
_cell_length_c                   10.125(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2.32
_cell_volume                     1661.1(7)
_computing_cell_refinement       'KM-4 Software'
_computing_data_collection       'KM-4 Software (Kuma Diffraction, 1989)'
_computing_data_reduction        'KM-4 Software'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3424
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.32
_diffrn_standards_decay_%        0.58
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.154
_refine_ls_extinction_coef       0.0155(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0582P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                1619
_reflns_number_total             3267
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga1086.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014681
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
'-x, y+1/2, -z+1/2'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.20927(15) 0.47340(11) -0.09760(19) 0.0516(4) Uani d . 1 . . C
H1A 0.2748 0.4306 -0.0665 0.062 Uiso d R 1 . . H
C2 0.14294(17) 0.49015(12) -0.24163(19) 0.0602(5) Uani d . 1 . . C
H2A 0.1621 0.4594 -0.3121 0.072 Uiso d R 1 . . H
C3 0.04734(17) 0.55282(13) -0.2900(2) 0.0624(5) Uani d . 1 . . C
H3A 0.0007 0.5637 -0.3925 0.075 Uiso d R 1 . . H
C4 0.01969(16) 0.59823(11) -0.19379(19) 0.0539(5) Uani d . 1 . . C
H4A -0.0465 0.6405 -0.2281 0.065 Uiso d R 1 . . H
C5 0.08440(18) 0.66635(11) 0.2897(2) 0.0618(5) Uani d . 1 . . C
H5A 0.0183 0.7086 0.2510 0.074 Uiso d R 1 . . H
C6 0.1444(2) 0.65547(13) 0.4348(2) 0.0713(6) Uani d . 1 . . C
H6A 0.1220 0.6895 0.4996 0.086 Uiso d R 1 . . H
C7 0.24110(19) 0.59421(13) 0.4949(2) 0.0669(5) Uani d . 1 . . C
H7A 0.2837 0.5880 0.5990 0.080 Uiso d R 1 . . H
C8 0.27579(16) 0.54401(11) 0.40834(19) 0.0557(5) Uani d . 1 . . C
H8A 0.3419 0.5023 0.4522 0.067 Uiso d R 1 . . H
C9 0.24516(13) 0.50435(9) 0.15759(17) 0.0409(4) Uani d . 1 . . C
N10 0.05513(12) 0.63085(8) 0.04906(15) 0.0490(3) Uani d . 1 . . N
C11 0.18284(14) 0.51921(9) 0.00771(16) 0.0414(4) Uani d . 1 . . C
C12 0.08646(14) 0.58377(9) -0.04112(17) 0.0435(4) Uani d . 1 . . C
C13 0.21465(14) 0.55312(10) 0.25398(17) 0.0432(4) Uani d . 1 . . C
C14 0.11726(15) 0.61638(10) 0.19307(19) 0.0469(4) Uani d . 1 . . C
C15 0.34256(15) 0.43544(10) 0.21445(17) 0.0468(4) Uani d . 1 . . C
O16 0.29415(10) 0.36404(7) 0.24412(13) 0.0534(3) Uani d . 1 . . O
O17 0.44758(12) 0.44111(9) 0.2296(2) 0.0927(6) Uani d . 1 . . O
C18 0.36886(14) 0.28859(10) 0.29262(18) 0.0448(4) Uani d . 1 . . C
C19 0.33351(14) 0.21791(10) 0.20007(18) 0.0489(4) Uani d . 1 . . C
C20 0.40315(16) 0.14305(11) 0.2551(2) 0.0575(5) Uani d . 1 . . C
H20A 0.3847 0.0922 0.1946 0.069 Uiso d R 1 . . H
C21 0.49853(16) 0.13915(11) 0.3931(2) 0.0581(5) Uani d . 1 . . C
H21A 0.5435 0.0858 0.4283 0.070 Uiso d R 1 . . H
C22 0.53092(15) 0.21036(11) 0.4839(2) 0.0523(4) Uani d . 1 . . C
C23 0.46436(14) 0.28639(10) 0.43039(18) 0.0484(4) Uani d . 1 . . C
H23A 0.4860 0.3378 0.4897 0.058 Uiso d R 1 . . H
C24 0.22563(17) 0.22178(13) 0.0514(2) 0.0693(6) Uani d . 1 . . C
H24A 0.1517 0.2414 0.0601 0.104 Uiso d R 1 . . H
H24B 0.2108 0.1650 0.0081 0.104 Uiso d R 1 . . H
H24C 0.2454 0.2613 -0.0091 0.104 Uiso d R 1 . . H
C25 0.63114(18) 0.20648(13) 0.6379(2) 0.0746(6) Uani d . 1 . . C
H25A 0.7032 0.1765 0.6394 0.112 Uiso d R 1 . . H
H25B 0.5996 0.1761 0.6981 0.112 Uiso d R 1 . . H
H25C 0.6546 0.2644 0.6745 0.112 Uiso d R 1 . . H
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_publ_flag
C2 C1 C11 120.27(16) ?
C2 C1 H1A 119.9 ?
C11 C1 H1A 119.8 ?
C1 C2 C3 121.09(17) ?
C1 C2 H2A 119.7 ?
C3 C2 H2A 119.2 ?
C4 C3 C2 120.62(17) ?
C4 C3 H3A 119.2 ?
C2 C3 H3A 120.2 ?
C3 C4 C12 120.87(17) ?
C3 C4 H4A 120.0 ?
C12 C4 H4A 119.2 ?
C6 C5 C14 121.0(2) ?
C6 C5 H5A 119.2 ?
C14 C5 H5A 119.8 ?
C5 C6 C7 120.7(2) ?
C5 C6 H6A 120.7 ?
C7 C6 H6A 118.6 ?
C8 C7 C6 121.0(2) ?
C8 C7 H7A 119.5 ?
C6 C7 H7A 119.5 ?
C7 C8 C13 120.2(2) ?
C7 C8 H8A 119.4 ?
C13 C8 H8A 120.4 ?
C13 C9 C11 120.02(13) ?
C13 C9 C15 119.96(14) ?
C12 N10 C14 118.11(14) ?
C9 C11 C1 123.64(14) ?
C9 C11 C12 117.58(14) ?
C1 C11 C12 118.78(14) ?
N10 C12 C4 118.20(15) ?
N10 C12 C11 123.43(15) ?
C4 C12 C11 118.36(15) ?
C9 C13 C8 123.74(15) ?
C9 C13 C14 117.61(14) ?
C8 C13 C14 118.65(15) ?
N10 C14 C5 118.38(16) ?
N10 C14 C13 123.23(15) ?
C5 C14 C13 118.38(16) ?
C9 C15 O16 110.12(13) yes
C9 C15 O17 126.07(15) yes
C11 C9 C15 120.01(14) ?
C15 O16 C18 119.69(12) yes
O16 C15 O17 123.80(15) yes
O16 C18 C19 116.71(14) ?
C18 C19 C24 122.10(15) ?
C23 C18 C19 123.48(15) ?
C23 C18 O16 119.59(15) ?
C18 C19 C20 115.30(15) ?
C20 C19 C24 122.59(16) ?
C21 C20 C19 122.22(17) ?
C21 C20 H20A 118.6 ?
C19 C20 H20A 119.1 ?
C20 C21 C22 121.29(16) ?
C20 C21 H21A 119.9 ?
C22 C21 H21A 118.8 ?
C21 C22 C23 117.56(17) ?
C21 C22 C25 122.19(17) ?
C23 C22 C25 120.21(17) ?
C18 C23 C22 120.13(16) ?
C18 C23 H23A 120.0 ?
C22 C23 H23A 119.8 ?
C19 C24 H24A 109.5 ?
C19 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
C19 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
C22 C25 H25A 109.5 ?
C22 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
C22 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.354(2) ?
C1 C11 . 1.419(2) ?
C1 H1A . 0.96 ?
C2 C3 . 1.403(3) ?
C2 H2A . 0.96 ?
C3 C4 . 1.347(2) ?
C3 H3A . 0.96 ?
C4 C12 . 1.422(2) ?
C4 H4A . 0.96 ?
C5 C6 . 1.343(3) ?
C5 C14 . 1.421(2) ?
C5 H5A . 0.96 ?
C6 C7 . 1.402(3) ?
C6 H6A . 0.96 ?
C7 C8 . 1.356(3) ?
C7 H7A . 0.96 ?
C8 C13 . 1.422(2) ?
C8 H8A . 0.96 ?
C9 C13 . 1.394(2) ?
C9 C11 . 1.395(2) yes
C9 C15 . 1.487(2) yes
N10 C12 . 1.335(2) yes
N10 C14 . 1.343(2) ?
C11 C12 . 1.429(2) ?
C13 C14 . 1.429(2) ?
C15 O16 . 1.330(2) yes
C15 O17 . 1.182(2) yes
O16 C18 . 1.413(2) yes
C18 C23 . 1.370(2) ?
C18 C19 . 1.380(2) ?
C19 C20 . 1.387(2) ?
C19 C24 . 1.502(2) ?
C20 C21 . 1.372(2) ?
C20 H20A . 0.96 ?
C21 C22 . 1.377(2) ?
C21 H21A . 0.96 ?
C22 C23 . 1.385(2) ?
C22 C25 . 1.503(2) ?
C23 H23A . 0.96 ?
C24 H24A . 0.96 ?
C24 H24B . 0.96 ?
C24 H24C . 0.96 ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 0.96 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C25 H25C CgC 3_666 0.96 2.87 3.622(2) 136 y
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_publ_flag
C11 C1 C2 C3 0.1(3) ?
C1 C2 C3 C4 0.3(3) ?
C2 C3 C4 C12 -0.1(3) ?
C14 C5 C6 C7 -0.2(3) ?
C5 C6 C7 C8 -0.5(3) ?
C6 C7 C8 C13 0.4(3) ?
C13 C9 C11 C1 179.11(15) ?
C15 C9 C11 C1 -2.0(2) ?
C13 C9 C11 C12 -1.5(2) ?
C15 C9 C11 C12 177.43(13) ?
C2 C1 C11 C9 178.60(15) ?
C2 C1 C11 C12 -0.8(2) ?
C14 N10 C12 C4 179.22(14) ?
C14 N10 C12 C11 -0.3(2) ?
C3 C4 C12 N10 179.86(16) ?
C3 C4 C12 C11 -0.6(2) ?
C9 C11 C12 N10 1.1(2) ?
C1 C11 C12 N10 -179.47(14) ?
C9 C11 C12 C4 -178.40(13) ?
C1 C11 C12 C4 1.0(2) ?
C11 C9 C13 C8 -178.14(14) ?
C15 C9 C13 C8 2.9(2) ?
C9 C15 O16 C18 176.78(13) yes
C11 C9 C13 C14 1.1(2) ?
C11 C9 C15 O16 -99.33(16) ?
C11 C9 C15 O17 79.4(2) yes
C15 O16 C18 C23 71.6(2) yes
O16 C18 C19 C24 3.4(2) ?
O17 C15 O16 C18 -2.0(3) ?
C15 O16 C18 C19 -113.59(16) ?
C15 C9 C13 C14 -177.82(13) ?
C7 C8 C13 C9 179.68(16) ?
C7 C8 C13 C14 0.4(2) ?
C12 N10 C14 C5 179.95(15) ?
C12 N10 C14 C13 -0.2(2) ?
C6 C5 C14 N10 -179.15(16) ?
C6 C5 C14 C13 1.0(3) ?
C9 C13 C14 N10 -0.3(2) ?
C8 C13 C14 N10 179.02(15) ?
C9 C13 C14 C5 179.64(15) ?
C8 C13 C14 C5 -1.1(2) ?
C13 C9 C15 O17 -101.7(2) ?
C13 C9 C15 O16 79.59(18) ?
C23 C18 C19 C20 -1.0(2) ?
O16 C18 C19 C20 -175.58(13) ?
C23 C18 C19 C24 178.01(16) ?
C18 C19 C20 C21 1.5(2) ?
C24 C19 C20 C21 -177.49(17) ?
C19 C20 C21 C22 -0.8(3) ?
C20 C21 C22 C23 -0.5(3) ?
C20 C21 C22 C25 177.19(17) ?
C19 C18 C23 C22 -0.3(2) ?
O16 C18 C23 C22 174.20(14) ?
C21 C22 C23 C18 1.0(2) ?
C25 C22 C23 C18 -176.73(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 530135
