#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014680.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_2014680
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-ethylphenyl acridine-9-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.12(3)
_cell_angle_beta                 98.96(3)
_cell_angle_gamma                106.28(3)
_cell_formula_units_Z            2
_cell_length_a                   7.995(2)
_cell_length_b                   9.465(2)
_cell_length_c                   11.899(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      2.25
_cell_volume                     850.7(4)
_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  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0473
_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       0
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3507
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        1.27
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.178
_refine_ls_extinction_coef       0.027(4)
_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   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0440
_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)+(0.0568P)²+0.1515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1253
_reflns_number_gt                1788
_reflns_number_total             3337
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga1086.cif
_cod_data_source_block           I
_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_database_code               2014680
_cod_database_fobs_code          2014680
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.5133(3) 0.6084(2) 1.18451(18) 0.0511(5) Uani d . 1 . . C
H1A 0.4984 0.5760 1.1052 0.061 Uiso d R 1 . . H
C2 0.6438(3) 0.5833(3) 1.2593(2) 0.0650(6) Uani d . 1 . . C
H2A 0.7216 0.5336 1.2329 0.078 Uiso d R 1 . . H
C3 0.6677(4) 0.6299(3) 1.3758(2) 0.0781(8) Uani d . 1 . . C
H3A 0.7606 0.6097 1.4282 0.094 Uiso d R 1 . . H
C4 0.5649(4) 0.7033(3) 1.41436(19) 0.0718(7) Uani d . 1 . . C
H4A 0.5815 0.7319 1.4945 0.086 Uiso d R 1 . . H
C5 0.1004(4) 0.9242(3) 1.3584(2) 0.0677(7) Uani d . 1 . . C
H5A 0.1289 0.9556 1.4385 0.081 Uiso d R 1 . . H
C6 -0.0342(4) 0.9571(3) 1.2926(2) 0.0741(7) Uani d . 1 . . C
H6A -0.0949 1.0188 1.3246 0.089 Uiso d R 1 . . H
C7 -0.0827(3) 0.9057(3) 1.1765(2) 0.0663(6) Uani d . 1 . . C
H7A -0.1807 0.9283 1.1311 0.080 Uiso d R 1 . . H
C8 0.0062(3) 0.8253(2) 1.12776(18) 0.0519(5) Uani d . 1 . . C
H8A -0.0302 0.7904 1.0485 0.062 Uiso d R 1 . . H
C9 0.2568(2) 0.71311(19) 1.14893(15) 0.0380(4) Uani d . 1 . . C
N10 0.3295(3) 0.8110(2) 1.38188(14) 0.0561(5) Uani d . 1 . . N
C11 0.3964(3) 0.6831(2) 1.22095(15) 0.0411(5) Uani d . 1 . . C
C12 0.4262(3) 0.7344(2) 1.33895(16) 0.0499(5) Uani d . 1 . . C
C13 0.1528(3) 0.7912(2) 1.19268(15) 0.0409(5) Uani d . 1 . . C
C14 0.1980(3) 0.8399(2) 1.31147(16) 0.0489(5) Uani d . 1 . . C
C15 0.2216(2) 0.6582(2) 1.02595(15) 0.0392(4) Uani d . 1 . . C
O16 0.21642(18) 0.76849(14) 0.95782(10) 0.0460(4) Uani d . 1 . . O
O17 0.2048(2) 0.53417(16) 0.99104(11) 0.0538(4) Uani d . 1 . . O
C18 0.1779(3) 0.7319(2) 0.83844(14) 0.0400(5) Uani d . 1 . . C
C19 0.3075(3) 0.7949(2) 0.77632(15) 0.0426(5) Uani d . 1 . . C
C20 0.2640(3) 0.7638(2) 0.65900(16) 0.0497(5) Uani d . 1 . . C
H20A 0.3517 0.8043 0.6129 0.060 Uiso d R 1 . . H
C21 0.1011(3) 0.6749(2) 0.60717(17) 0.0550(6) Uani d . 1 . . C
H21A 0.0735 0.6555 0.5256 0.066 Uiso d R 1 . . H
C22 -0.0254(3) 0.6152(3) 0.67261(18) 0.0577(6) Uani d . 1 . . C
H22A -0.1396 0.5528 0.6369 0.069 Uiso d R 1 . . H
C23 0.0126(3) 0.6446(2) 0.78953(17) 0.0492(5) Uani d . 1 . . C
H23A -0.0751 0.6052 0.8357 0.059 Uiso d R 1 . . H
C24 0.4866(3) 0.8924(3) 0.8307(2) 0.0627(6) Uani d . 1 . . C
H24A 0.4754 0.9458 0.8979 0.075 Uiso d R 1 . . H
H24B 0.5298 0.9631 0.7785 0.075 Uiso d R 1 . . H
C25 0.6199(4) 0.8113(4) 0.8629(3) 0.1151(13) Uani d . 1 . . C
H25A 0.7319 0.8805 0.8946 0.173 Uiso d R 1 . . H
H25B 0.6318 0.7570 0.7963 0.173 Uiso d R 1 . . H
H25C 0.5817 0.7440 0.9185 0.173 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 121.0(2) ?
C2 C1 H1A 119.6 ?
C11 C1 H1A 119.4 ?
C1 C2 C3 120.5(2) ?
C1 C2 H2A 119.7 ?
C3 C2 H2A 119.8 ?
C4 C3 C2 121.1(2) ?
C4 C3 H3A 119.5 ?
C2 C3 H3A 119.3 ?
C3 C4 C12 120.8(2) ?
C3 C4 H4A 119.8 ?
C12 C4 H4A 119.4 ?
C6 C5 C14 120.7(2) ?
C6 C5 H5A 119.9 ?
C14 C5 H5A 119.4 ?
C5 C6 C7 120.5(2) ?
C5 C6 H6A 119.7 ?
C7 C6 H6a 119.7 ?
C8 C7 C6 121.1(2) ?
C8 C7 H7A 119.5 ?
C6 C7 H7A 119.5 ?
C7 C8 C13 120.7(2) ?
C7 C8 H8A 119.6 ?
C13 C8 H8A 119.6 ?
C13 C9 C11 120.25(16) ?
C13 C9 C15 121.52(17) ?
C14 N10 C12 118.59(17) ?
C9 C11 C1 124.70(17) ?
C9 C11 C12 117.4(2) ?
C1 C11 C12 117.9(2) ?
N10 C12 C4 118.3(2) ?
N10 C12 C11 123.1(2) ?
C4 C12 C11 118.6(2) ?
C9 C13 C8 124.89(17) ?
C9 C13 C14 117.2(2) ?
C8 C13 C14 117.8(2) ?
N10 C14 C5 117.5(2) ?
N10 C14 C13 123.4(2) ?
C5 C14 C13 119.1(2) ?
C9 C15 O16 111.19(16) yes
C9 C15 O17 125.0(2) yes
C11 C9 C15 118.22(17) ?
C15 O16 C18 117.60(14) yes
O16 C15 O17 123.74(17) yes
O16 C18 C19 117.20(17) ?
C18 C19 C24 122.8(2) ?
C23 C18 C19 123.34(17) ?
C23 C18 O16 119.32(17) ?
C18 C19 C20 116.3(2) ?
C20 C19 C24 120.8(2) ?
C21 C20 C19 122.0(2) ?
C21 C20 H20A 119.2 ?
C19 C20 H20A 118.8 ?
C20 C21 C22 119.7(2) ?
C20 C21 H21A 120.5 ?
C22 C21 H21A 119.7 ?
C23 C22 C21 120.0(2) ?
C23 C22 H22A 119.9 ?
C21 C22 H22A 120.1 ?
C18 C23 C22 118.6(2) ?
C18 C23 H23A 120.7 ?
C22 C23 H23A 120.7 ?
C25 C24 C19 114.0(2) ?
C25 C24 H24A 108.8 ?
C19 C24 H24A 109.0 ?
C25 C24 H24B 108.5 ?
C19 C24 H24B 108.7 ?
H24A C24 H24B 107.7 ?
C24 C25 H25A 109.5 ?
C24 C25 H25B 109.4 ?
H25A C25 H25B 109.5 ?
C24 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 . 1.343(3) ?
C1 C11 . 1.426(3) ?
C1 H1A . 0.96 ?
C2 C3 . 1.406(3) ?
C2 H2A . 0.96 ?
C3 C4 . 1.335(4) ?
C3 H3A . 0.96 ?
C4 C12 . 1.419(3) ?
C4 H4A . 0.96 ?
C5 C6 . 1.346(4) ?
C5 C14 . 1.417(3) ?
C5 H5A . 0.96 ?
C6 C7 . 1.404(3) ?
C6 H6A . 0.96 ?
C7 C8 . 1.349(3) ?
C7 H7A . 0.96 ?
C8 C13 . 1.423(3) ?
C8 H8A . 0.96 ?
C9 C13 . 1.400(3) ?
C9 C11 . 1.400(3) yes
C9 C15 . 1.491(2) yes
N10 C14 . 1.337(3) ?
N10 C12 . 1.339(3) yes
C11 C12 . 1.430(3) ?
C13 C14 . 1.429(3) ?
C15 O16 . 1.351(2) yes
C15 O17 . 1.195(2) yes
O16 C18 . 1.414(2) yes
C18 C23 . 1.371(3) ?
C18 C19 . 1.379(3) ?
C19 C20 . 1.385(3) ?
C19 C24 . 1.499(3) ?
C20 C21 . 1.372(3) ?
C20 H20A . 0.96 ?
C21 C22 . 1.380(3) ?
C21 H21A . 0.96 ?
C22 C23 . 1.377(3) ?
C22 H22A . 0.96 ?
C23 H23A . 0.96 ?
C24 C25 . 1.491(4) ?
C24 H24A . 0.96 ?
C24 H24B . 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
C2 H2A CgA 2_667 0.96 2.81 3.608(3) 142 y
C6 H6A CgA 2_577 0.96 2.81 3.540(3) 133 y
C24 H24A CgB 2_677 0.96 2.70 3.576(3) 151 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 0.2(4) ?
C1 C2 C3 C4 -1.8(4) ?
C2 C3 C4 C12 1.1(5) ?
C14 C5 C6 C7 1.4(4) ?
C5 C6 C7 C8 -1.5(4) ?
C6 C7 C8 C13 -0.5(4) ?
C13 C9 C11 C1 -178.0(2) ?
C15 C9 C11 C1 2.7(3) ?
C13 C9 C11 C12 0.3(3) ?
C15 C9 C11 C12 -179.0(2) ?
C2 C1 C11 C9 -179.7(2) ?
C2 C1 C11 C12 2.0(3) ?
C14 N10 C12 C4 -179.6(2) ?
C14 N10 C12 C11 0.5(3) ?
C3 C4 C12 N10 -178.7(2) ?
C3 C4 C12 C11 1.2(4) ?
C9 C11 C12 N10 -1.2(3) ?
C1 C11 C12 N10 177.2(2) ?
C9 C11 C12 C4 178.9(2) ?
C1 C11 C12 C4 -2.6(3) ?
C11 C9 C13 C8 -178.8(2) ?
C15 C9 C13 C8 0.4(3) ?
C15 C9 C13 C14 -179.59(17) ?
C7 C8 C13 C9 -177.7(2) ?
C7 C8 C13 C14 2.3(3) ?
C12 N10 C14 C5 -178.5(2) ?
C12 N10 C14 C13 1.1(3) ?
C6 C5 C14 N10 -179.8(2) ?
C6 C5 C14 C13 0.6(4) ?
C9 C13 C14 N10 -1.9(3) ?
C8 C13 C14 N10 178.0(2) ?
C9 C13 C14 C5 177.6(2) ?
C8 C13 C14 C5 -2.4(3) ?
C13 C9 C15 O17 -128.4(2) ?
C13 C9 C15 O16 53.5(2) ?
C9 C15 O16 C18 -177.82(16) yes
C11 C9 C13 C14 1.2(3) ?
C11 C9 C15 O16 -127.2(2) ?
C11 C9 C15 O17 50.8(3) yes
C15 O16 C18 C19 -116.7(2) yes
O16 C18 C19 C24 3.1(3) ?
O17 C15 O16 C18 4.1(3) ?
C15 O16 C18 C23 67.3(2) ?
C23 C18 C19 C20 -1.0(3) ?
O16 C18 C19 C20 -176.74(17) ?
C23 C18 C19 C24 178.8(2) ?
C18 C19 C20 C21 -0.2(3) ?
C24 C19 C20 C21 180.0(2) ?
C19 C20 C21 C22 0.8(3) ?
C20 C21 C22 C23 -0.3(3) ?
C19 C18 C23 C22 1.5(3) ?
O16 C18 C23 C22 177.2(2) ?
C21 C22 C23 C18 -0.8(3) ?
C18 C19 C24 C25 89.5(3) ?
C20 C19 C24 C25 -90.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21133996
