#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/13/2011339.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_2011339
loop_
_publ_author_name
'Jeyakanthan, J.'
'Shanmuga Sundara Raj, S.'
'Velmurugan, D.'
'Fun, Hoong-Kun'
'Rajan, T. Joseph'
'Ramakrishnan, V.T.'
_publ_section_title
;
 Two benzoylaminoacridinedione derivatives
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1109
_journal_page_last               1112
_journal_paper_doi               10.1107/S0108270199016455
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C20 H20 N2 O3 , H2 O'
_chemical_formula_sum            'C20 H22 N2 O4'
_chemical_formula_weight         354.40
_chemical_name_systematic
;
10-(benzoylamino)-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)-acridinedione (I)
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.4970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4056(2)
_cell_length_b                   12.25010(10)
_cell_length_c                   13.1746(3)
_cell_measurement_reflns_used    6167
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      1.79
_cell_volume                     1840.12(5)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1983, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .930
_diffrn_measured_fraction_theta_max .930
_diffrn_measurement_device_type
'Siemens SMART CCD area detector Diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0322
_diffrn_reflns_av_sigmaI/netI    .0403
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12199
_diffrn_reflns_theta_full        28.44
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    .090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             752
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .08
_refine_diff_density_max         .521
_refine_diff_density_min         -.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          .0842
_refine_ls_R_factor_gt           .0561
_refine_ls_shift/su_max          .000
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0755P)²+0.5302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1670
_reflns_number_gt                3066
_reflns_number_total             4512
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ka1336.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.5302P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.5302P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011339
_cod_database_fobs_code          2011339
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
O1 1.23695(13) .72286(15) -.12058(14) .0765(5) Uani d . 1 . . O
O2 .94941(15) .44042(15) -.25585(12) .0753(5) Uani d . 1 . . O
O3 .71019(13) .83820(13) -.03779(10) .0628(4) Uani d . 1 . . O
C1 1.16121(17) .75573(17) -.06314(16) .0530(5) Uani d . 1 . . C
C1A 1.05034(15) .69651(15) -.05398(13) .0421(4) Uani d . 1 . . C
C2 1.1774(2) .8579(2) -.0029(2) .0729(7) Uani d . 1 . . C
H2A 1.1501 .9194 -.0434 .088 Uiso calc R 1 . . H
H2B 1.2604 .8684 .0119 .088 Uiso calc R 1 . . H
C3 1.1133(2) .8566(2) .0950(2) .0802(8) Uani d . 1 . . C
H3A 1.1188 .9283 .1258 .096 Uiso calc R 1 . . H
H3B 1.1516 .8052 .1410 .096 Uiso calc R 1 . . H
C4 .98483(18) .82563(18) .08270(17) .0589(5) Uani d . 1 . . C
H4A .9544 .8068 .1485 .071 Uiso calc R 1 . . H
H4B .9408 .8879 .0568 .071 Uiso calc R 1 . . H
C4A .96784(15) .73105(14) .01163(13) .0418(4) Uani d . 1 . . C
C5 .87640(18) .47744(17) -.19661(15) .0539(5) Uani d . 1 . . C
C5A .90911(15) .55826(15) -.12073(13) .0427(4) Uani d . 1 . . C
C6 .7503(2) .4434(2) -.2046(2) .0749(7) Uani d . 1 . . C
H6A .7461 .3694 -.2307 .090 Uiso calc R 1 . . H
H6B .7095 .4905 -.2530 .090 Uiso calc R 1 . . H
C7 .6883(2) .4478(2) -.1055(2) .0771(7) Uani d . 1 . . C
H7A .7173 .3891 -.0622 .093 Uiso calc R 1 . . H
H7B .6052 .4356 -.1183 .093 Uiso calc R 1 . . H
C8 .70433(18) .55438(18) -.05035(18) .0596(5) Uani d . 1 . . C
H8A .6518 .6083 -.0805 .072 Uiso calc R 1 . . H
H8B .6833 .5449 .0200 .072 Uiso calc R 1 . . H
C8A .82820(15) .59571(15) -.05409(13) .0420(4) Uani d . 1 . . C
C9 1.03328(16) .59835(17) -.12132(14) .0485(4) Uani d . 1 . . C
H9A 1.0535 .6172 -.1902 .058 Uiso calc R 1 . . H
H9B 1.0855 .5404 -.0982 .058 Uiso calc R 1 . . H
N10 .85975(12) .67670(13) .01556(11) .0455(4) Uani d . 1 . . N
N11 .77321(13) .71683(13) .08003(11) .0468(4) Uani d . 1 . . N
H11 .7667 .6907 .1402 .056 Uiso calc R 1 . . H
C12 .70035(15) .79687(15) .04634(13) .0448(4) Uani d . 1 . . C
C13 .60590(14) .82915(15) .11858(13) .0421(4) Uani d . 1 . . C
C14 .55390(16) .93074(17) .10426(15) .0503(4) Uani d . 1 . . C
H14 .5800 .9770 .0536 .060 Uiso calc R 1 . . H
C15 .46231(18) .96351(19) .16583(17) .0590(5) Uani d . 1 . . C
H15 .4276 1.0315 .1557 .071 Uiso calc R 1 . . H
C16 .42296(17) .8957(2) .24160(17) .0619(6) Uani d . 1 . . C
H16 .3613 .9176 .2817 .074 Uiso calc R 1 . . H
C17 .47542(19) .7956(2) .25751(18) .0650(6) Uani d . 1 . . C
H17 .4501 .7504 .3092 .078 Uiso calc R 1 . . H
C18 .56660(17) .76214(17) .19593(17) .0551(5) Uani d . 1 . . C
H18 .6014 .6943 .2067 .066 Uiso calc R 1 . . H
O1W .18109(18) .1329(2) .22943(13) .0907(7) Uani d . 1 . . O
HWA .108(3) .113(2) .230(2) .084(9) Uiso d . 1 . . H
HWB .204(3) .152(3) .169(3) .100(10) Uiso d . 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
O1 C1 C1A 120.64(19) yes
O1 C1 C2 121.50(19) yes
C1A C1 C2 117.84(17) ?
C4A C1A C1 120.70(17) ?
C4A C1A C9 122.82(16) ?
C1 C1A C9 116.47(15) ?
C1 C2 C3 113.1(2) ?
C1 C2 H2A 109.0 ?
C3 C2 H2A 109.0 ?
C1 C2 H2B 109.0 ?
C3 C2 H2B 109.0 ?
H2A C2 H2B 107.8 ?
C2 C3 C4 113.7(2) ?
C2 C3 H3A 108.8 ?
C4 C3 H3A 108.8 ?
C2 C3 H3B 108.8 ?
C4 C3 H3B 108.8 ?
H3A C3 H3B 107.7 ?
C4A C4 C3 111.61(17) ?
C4A C4 H4A 109.3 ?
C3 C4 H4A 109.3 ?
C4A C4 H4B 109.3 ?
C3 C4 H4B 109.3 ?
H4A C4 H4B 108.0 ?
C1A C4A N10 119.89(16) yes
C1A C4A C4 123.81(17) ?
N10 C4A C4 116.30(15) yes
O2 C5 C5A 121.22(19) yes
O2 C5 C6 120.83(19) yes
C5A C5 C6 117.89(17) ?
C8A C5A C5 120.37(17) ?
C8A C5A C9 123.10(16) ?
C5 C5A C9 116.52(15) ?
C5 C6 C7 113.70(19) ?
C5 C6 H6A 108.8 ?
C7 C6 H6A 108.8 ?
C5 C6 H6B 108.8 ?
C7 C6 H6B 108.8 ?
H6A C6 H6B 107.7 ?
C6 C7 C8 113.4(2) ?
C6 C7 H7A 108.9 ?
C8 C7 H7A 108.9 ?
C6 C7 H7B 108.9 ?
C8 C7 H7B 108.9 ?
H7A C7 H7B 107.7 ?
C8A C8 C7 112.28(17) ?
C8A C8 H8A 109.1 ?
C7 C8 H8A 109.1 ?
C8A C8 H8B 109.1 ?
C7 C8 H8B 109.1 ?
H8A C8 H8B 107.9 ?
C5A C8A N10 119.63(16) yes
C5A C8A C8 123.92(17) ?
N10 C8A C8 116.45(15) yes
C5A C9 C1A 111.50(14) ?
C5A C9 H9A 109.3 ?
C1A C9 H9A 109.3 ?
C5A C9 H9B 109.3 ?
C1A C9 H9B 109.3 ?
H9A C9 H9B 108.0 ?
C8A N10 C4A 121.74(14) yes
C8A N10 N11 118.25(14) yes
C4A N10 N11 119.15(15) yes
C12 N11 N10 119.32(14) yes
C12 N11 H11 120.3 ?
N10 N11 H11 120.3 ?
O3 C12 N11 121.73(16) yes
O3 C12 C13 123.07(16) yes
N11 C12 C13 115.20(15) yes
C14 C13 C18 118.90(16) ?
C14 C13 C12 117.28(16) ?
C18 C13 C12 123.79(16) ?
C13 C14 C15 120.08(19) ?
C13 C14 H14 120.0 ?
C15 C14 H14 120.0 ?
C16 C15 C14 120.54(19) ?
C16 C15 H15 119.7 ?
C14 C15 H15 119.7 ?
C17 C16 C15 119.77(18) ?
C17 C16 H16 120.1 ?
C15 C16 H16 120.1 ?
C16 C17 C18 120.0(2) ?
C16 C17 H17 120.0 ?
C18 C17 H17 120.0 ?
C13 C18 C17 120.71(19) ?
C13 C18 H18 119.6 ?
C17 C18 H18 119.6 ?
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
O1 C1 . 1.231(2) yes
O2 C5 . 1.242(2) yes
O3 C12 . 1.226(2) yes
C1 C1A . 1.465(3) yes
C1 C2 . 1.491(3) ?
C1A C4A . 1.362(2) yes
C1A C9 . 1.504(3) yes
C2 C3 . 1.499(3) ?
C2 H2A . .9700 ?
C2 H2B . .9700 ?
C3 C4 . 1.518(3) ?
C3 H3A . .9700 ?
C3 H3B . .9700 ?
C4 C4A . 1.499(3) ?
C4 H4A . .9700 ?
C4 H4B . .9700 ?
C4A N10 . 1.403(2) yes
C5 C5A . 1.449(3) yes
C5 C6 . 1.499(3) ?
C5A C8A . 1.369(2) yes
C5A C9 . 1.499(3) yes
C6 C7 . 1.501(4) ?
C6 H6A . .9700 ?
C6 H6B . .9700 ?
C7 C8 . 1.503(3) ?
C7 H7A . .9700 ?
C7 H7B . .9700 ?
C8 C8A . 1.503(3) yes
C8 H8A . .9700 ?
C8 H8B . .9700 ?
C8A N10 . 1.392(2) yes
C9 H9A . .9700 ?
C9 H9B . .9700 ?
N10 N11 . 1.4075(18) yes
N11 C12 . 1.353(2) yes
N11 H11 . .8600 ?
C12 C13 . 1.509(2) ?
C13 C14 . 1.389(3) ?
C13 C18 . 1.392(3) ?
C14 C15 . 1.398(3) ?
C14 H14 . .9300 ?
C15 C16 . 1.383(3) ?
C15 H15 . .9300 ?
C16 C17 . 1.378(3) ?
C16 H16 . .9300 ?
C17 C18 . 1.397(3) ?
C17 H17 . .9300 ?
C18 H18 . .9300 ?
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
N11 H11 O1W 2_655 .86 1.937 2.750(2) 157.2
C16 H16 O1 4_476 .93 2.593 3.180(3) 121.5
C17 H17 O1 4_476 .93 2.644 3.203(3) 119.2
C18 H18 O1W 2_655 .93 2.705 3.407(3) 132.9
O1W HWA O2 4_466 .87 1.937 2.802(3) 173.9
O1W HWB O3 3_665 .88 2.012 2.864(2) 163.7
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
O1 C1 C1A C4A 178.15(19)
C2 C1 C1A C4A -3.4(3)
O1 C1 C1A C9 -2.7(3)
C2 C1 C1A C9 175.76(19)
O1 C1 C2 C3 -151.0(2)
C1A C1 C2 C3 30.5(3)
C1 C2 C3 C4 -51.0(3)
C2 C3 C4 C4A 43.4(3)
C1 C1A C4A N10 176.68(16)
C9 C1A C4A N10 -2.4(3)
C1 C1A C4A C4 -3.7(3)
C9 C1A C4A C4 177.25(17)
C3 C4 C4A C1A -16.5(3)
C3 C4 C4A N10 163.2(2)
O2 C5 C5A C8A -178.04(19)
C6 C5 C5A C8A 4.6(3)
O2 C5 C5A C9 3.0(3)
C6 C5 C5A C9 -174.36(19)
O2 C5 C6 C7 151.7(2)
C5A C5 C6 C7 -31.0(3)
C5 C6 C7 C8 50.0(3)
C6 C7 C8 C8A -42.0(3)
C5 C5A C8A N10 -177.31(16)
C9 C5A C8A N10 1.6(3)
C5 C5A C8A C8 2.9(3)
C9 C5A C8A C8 -178.24(18)
C7 C8 C8A C5A 16.2(3)
C7 C8 C8A N10 -163.60(19)
C8A C5A C9 C1A -10.1(2)
C5 C5A C9 C1A 168.82(15)
C4A C1A C9 C5A 10.5(2)
C1 C1A C9 C5A -168.61(16)
C5A C8A N10 C4A 8.0(3)
C8 C8A N10 C4A -172.16(17)
C5A C8A N10 N11 177.27(15)
C8 C8A N10 N11 -2.9(2)
C1A C4A N10 C8A -7.6(3)
C4 C4A N10 C8A 172.72(16)
C1A C4A N10 N11 -176.78(15)
C4 C4A N10 N11 3.5(2)
C8A N10 N11 C12 -84.2(2)
C4A N10 N11 C12 85.3(2)
N10 N11 C12 O3 -2.6(3)
N10 N11 C12 C13 176.27(15)
O3 C12 C13 C14 -21.3(3)
N11 C12 C13 C14 159.89(17)
O3 C12 C13 C18 156.9(2)
N11 C12 C13 C18 -21.9(3)
C18 C13 C14 C15 -1.1(3)
C12 C13 C14 C15 177.21(18)
C13 C14 C15 C16 .3(3)
C14 C15 C16 C17 .9(3)
C15 C16 C17 C18 -1.2(4)
C14 C13 C18 C17 .8(3)
C12 C13 C18 C17 -177.4(2)
C16 C17 C18 C13 .4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135569
