#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/57/2215701.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_2215701
loop_
_publ_author_name
'Karol Krzymiński'
'Artur Sikorski'
'Jerzy Błażejowski'
_publ_section_title
;
 Ethyl (9-oxo-9,10-dihydroacridin-10-yl)acetate
;
_journal_coeditor_code           XU2311
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3972
_journal_page_last               o3973
_journal_paper_doi               10.1107/S1600536807042663
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H15 N O3'
_chemical_formula_moiety         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_chemical_name_systematic
;
Ethyl (9-oxo-9,10-dihydroacridin-10-yl)acetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 96.069(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3232(3)
_cell_length_b                   10.3380(2)
_cell_length_c                   11.8925(3)
_cell_measurement_reflns_used    2420
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.28
_cell_volume                     1384.32(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Diffraction GEMINI R ULTRA'
_diffrn_measurement_method       ω
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8822
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.28
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.204
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.066P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                1776
_reflns_number_total             2426
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2311.cif
_cod_data_source_block           I
_cod_original_cell_volume        1384.33(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215701
_cod_database_fobs_code          2215701
loop_
_symmetry_equiv_pos_as_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_type_symbol
_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
C C1 0.74768(11) 0.07698(13) 0.59379(11) 0.0255(3) Uani d . 1
H H1 0.7852 0.0956 0.6673 0.031 Uiso calc R 1
C C2 0.79552(12) -0.01492(14) 0.53008(12) 0.0301(4) Uani d . 1
H H2 0.8643 -0.0614 0.5594 0.036 Uiso calc R 1
C C3 0.74185(12) -0.03963(14) 0.42115(12) 0.0318(4) Uani d . 1
H H3 0.7762 -0.1013 0.3751 0.038 Uiso calc R 1
C C4 0.64007(12) 0.02402(13) 0.37971(12) 0.0272(3) Uani d . 1
H H4 0.6049 0.0057 0.3053 0.033 Uiso calc R 1
C C5 0.33185(11) 0.34410(12) 0.42677(11) 0.0235(3) Uani d . 1
H H5 0.2908 0.3207 0.3559 0.028 Uiso calc R 1
C C6 0.29030(11) 0.44419(13) 0.48748(11) 0.0263(3) Uani d . 1
H H6 0.2210 0.4894 0.4576 0.032 Uiso calc R 1
C C7 0.34785(12) 0.48082(13) 0.59227(12) 0.0267(3) Uani d . 1
H H7 0.3188 0.5508 0.6332 0.032 Uiso calc R 1
C C8 0.44674(11) 0.41402(12) 0.63490(11) 0.0238(3) Uani d . 1
H H8 0.4859 0.4377 0.7066 0.029 Uiso calc R 1
C C9 0.59786(11) 0.24433(12) 0.62432(11) 0.0220(3) Uani d . 1
N N10 0.48050(9) 0.17667(10) 0.40685(8) 0.0211(3) Uani d . 1
C C11 0.64392(11) 0.14521(12) 0.55352(11) 0.0209(3) Uani d . 1
C C12 0.58718(11) 0.11590(12) 0.44574(11) 0.0213(3) Uani d . 1
C C13 0.49175(11) 0.31132(12) 0.57522(10) 0.0202(3) Uani d . 1
C C14 0.43467(10) 0.27592(12) 0.46854(10) 0.0194(3) Uani d . 1
O O15 0.64646(8) 0.27032(9) 0.72029(7) 0.0296(3) Uani d . 1
C C16 0.42514(12) 0.14381(13) 0.29409(10) 0.0226(3) Uani d . 1
H H16A 0.3399 0.1672 0.2881 0.027 Uiso calc R 1
H H16B 0.4308 0.0493 0.2824 0.027 Uiso calc R 1
C C17 0.48365(11) 0.21345(12) 0.20307(11) 0.0224(3) Uani d . 1
O O18 0.44395(8) 0.16691(8) 0.10116(7) 0.0251(3) Uani d . 1
C C19 0.49230(12) 0.22930(14) 0.00575(11) 0.0269(3) Uani d . 1
H H19B 0.5781 0.2099 0.0073 0.032 Uiso calc R 1
H H19A 0.4824 0.3243 0.0100 0.032 Uiso calc R 1
C C20 0.42657(16) 0.17831(15) -0.10081(12) 0.0428(4) Uani d . 1
H H20C 0.4328 0.0838 -0.1020 0.064 Uiso calc R 1
H H20B 0.4610 0.2145 -0.1662 0.064 Uiso calc R 1
H H20A 0.3428 0.2033 -0.1040 0.064 Uiso calc R 1
O O21 0.55459(8) 0.29938(9) 0.21883(8) 0.0341(3) Uani d . 1
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 121.73(12) no
C2 C1 H1 119.1 no
C11 C1 H1 119.1 no
C1 C2 C3 118.96(12) no
C1 C2 H2 120.5 no
C3 C2 H2 120.5 no
C4 C3 C2 120.83(14) no
C4 C3 H3 119.6 no
C2 C3 H3 119.6 no
C3 C4 C12 120.96(12) no
C3 C4 H4 119.5 no
C12 C4 H4 119.5 no
C6 C5 C14 120.59(12) no
C6 C5 H5 119.7 no
C14 C5 H5 119.7 no
C5 C6 C7 121.35(12) no
C5 C6 H6 119.3 no
C7 C6 H6 119.3 no
C8 C7 C6 118.74(13) no
C8 C7 H7 120.6 no
C6 C7 H7 120.6 no
C7 C8 C13 121.47(11) no
C7 C8 H8 119.3 no
C13 C8 H8 119.3 no
O15 C9 C13 122.17(12) no
O15 C9 C11 122.13(11) no
N10 C16 C17 111.68(10) y
C11 C9 C13 115.70(11) y
C12 N10 C14 120.95(10) y
C14 N10 C16 120.51(10) y
C12 C11 C1 119.10(12) no
C12 C11 C9 121.45(11) no
C1 C11 C9 119.45(11) no
N10 C12 C11 120.09(12) no
N10 C12 C4 121.58(11) no
C11 C12 C4 118.33(11) no
C8 C13 C14 119.69(11) no
C8 C13 C9 119.09(11) no
C14 C13 C9 121.22(12) no
N10 C14 C5 121.58(11) no
N10 C14 C13 120.28(11) no
C5 C14 C13 118.14(12) no
N10 C16 H16A 109.3 no
C17 C16 H16A 109.3 no
N10 C16 H16B 109.3 no
C17 C16 H16B 109.3 no
H16B C16 H16B 107.9 no
C16 C17 O18 110.32(10) y
C16 C17 O21 125.35(12) y
C17 O18 C19 115.31(9) y
O18 C17 O21 124.32(12) y
O18 C19 C20 107.97(11) y
O18 C19 H19B 110.1 no
C20 C19 H19B 110.1 no
O18 C19 H19A 110.1 no
C20 C19 H19A 110.1 no
H19B C19 H19A 108.4 no
C19 C20 H20C 109.5 no
C19 C20 H20B 109.5 no
H20C C20 H20B 109.5 no
C19 C20 H20A 109.5 no
H20C C20 H20A 109.5 no
H20B C20 H20A 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.363(2) no
C1 C11 1.4100(17) no
C1 H1 0.9500 no
C2 C3 1.3951(19) no
C2 H2 0.9500 no
C3 C4 1.3725(19) no
C3 H3 0.9500 no
C4 C12 1.4061(19) no
C4 H4 0.9500 no
C5 C6 1.3731(19) no
C5 C14 1.4060(17) no
C5 H5 0.9500 no
C6 C7 1.3962(18) no
C6 H6 0.9500 no
C7 C8 1.3666(18) no
C7 H7 0.9500 no
C8 C13 1.4026(18) no
C8 H8 0.9500 no
C9 C13 1.4546(17) no
C9 C11 1.4574(18) y
C9 O15 1.2428(14) y
N10 C12 1.3962(16) n
N10 C14 1.3932(16) n
N10 C16 1.4591(15) y
C11 C12 1.4048(17) no
C13 C14 1.4099(16) no
C16 C17 1.5102(19) no
C16 H16A 0.9900 no
C16 H16B 0.9900 no
C17 O18 1.3369(15) y
C17 O21 1.1990(15) y
O18 C19 1.4610(16) y
C19 C20 1.4961(18) no
C19 H19B 0.9900 no
C19 H19A 0.9900 no
C20 H20C 0.9800 no
C20 H20B 0.9800 no
C20 H20A 0.9800 no
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
C3 H3 O21 2_645 0.95 2.53 3.4155(17) 154 y
C5 H5 O15 4_565 0.95 2.37 3.2781(15) 161 y
C16 H16A O15 4_565 0.99 2.34 3.3061(16) 164 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 1.6(2) no
C1 C2 C3 C4 -2.3(2) no
C2 C3 C4 C12 0.1(2) no
C14 C5 C6 C7 -0.4(2) no
C5 C6 C7 C8 -0.7(2) no
C6 C7 C8 C13 0.7(2) no
C2 C1 C11 C12 1.2(2) no
C2 C1 C11 C9 -178.80(12) no
O15 C9 C11 C12 179.25(12) no
C13 C9 C11 C12 -1.06(18) no
O15 C9 C11 C1 -0.74(19) no
C13 C9 C11 C1 178.95(11) no
C14 N10 C12 C11 6.44(18) no
C16 N10 C12 C11 179.62(11) no
C14 N10 C12 C4 -174.07(11) no
C16 N10 C12 C4 -0.88(18) no
C1 C11 C12 C4 -3.34(19) y
N10 C16 C17 O18 170.44(10) y
N10 C16 C17 O21 -10.40(19) y
C11 C9 C13 C14 3.50(18) y
C12 N10 C14 C13 -4.00(18) y
C1 C11 C12 N10 176.17(11) no
C9 C11 C12 N10 -3.82(19) no
C9 C11 C12 C4 176.68(12) no
C3 C4 C12 N10 -176.76(12) no
C3 C4 C12 C11 2.7(2) no
C7 C8 C13 C14 0.3(2) no
C7 C8 C13 C9 179.52(12) no
O15 C9 C13 C8 4.02(19) no
C11 C9 C13 C8 -175.67(11) no
O15 C9 C13 C14 -176.81(12) no
C12 N10 C14 C5 175.47(12) no
C16 N10 C14 C5 2.45(18) no
C16 N10 C14 C13 -177.02(11) no
C6 C5 C14 N10 -178.01(12) no
C6 C5 C14 C13 1.47(19) no
C8 C13 C14 N10 178.06(11) no
C9 C13 C14 N10 -1.10(18) no
C8 C13 C14 C5 -1.43(18) no
C9 C13 C14 C5 179.41(11) no
C14 N10 C16 C17 93.93(13) no
C12 N10 C16 C17 -79.29(14) no
O21 C17 O18 C19 -0.61(18) no
C16 C17 O18 C19 178.56(10) no
C17 O18 C19 C20 -172.36(12) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2117252
2 PubChem 2840265
