#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/13/2011340.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_2011340
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         'C21 H22 N2 O3 , H2 O'
_chemical_formula_sum            'C21 H24 N2 O4'
_chemical_formula_weight         368.42
_chemical_name_systematic
10-(4-methylbenzoylamino)-3,4,6,7,9,10-hexahydro-1,8-(2H,5H)-acridinedione(II)
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 132.1400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.2343(10)
_cell_length_b                   13.8327(6)
_cell_length_c                   16.3286(7)
_cell_measurement_reflns_used    6666
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      1.89
_cell_volume                     3891.4(3)
_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, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full .476
_diffrn_measured_fraction_theta_max .476
_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  .0307
_diffrn_reflns_av_sigmaI/netI    .0341
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10281
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    .088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          .48
_exptl_crystal_size_mid          .44
_exptl_crystal_size_min          .36
_refine_diff_density_max         .308
_refine_diff_density_min         -.319
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   .945
_refine_ls_hydrogen_treatment    'constr(execpt water molecule)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .945
_refine_ls_R_factor_all          .0705
_refine_ls_R_factor_gt           .0553
_refine_ls_shift/su_max          .003
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1225P)²+2.3517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1897
_reflns_number_gt                2634
_reflns_number_total             3424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ka1336.cif
_cod_data_source_block           II
_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^)+(0.1225P)^2^+2.3517P] 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^)+(0.1225P)^2^+2.3517P] 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      'C 2/c'
_cod_database_code               2011340
_cod_database_fobs_code          2011340
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 .19154(13) .35055(13) .14221(17) .0917(6) Uani d . 1 . . O
O2 .14732(16) .41574(14) .39752(19) .1088(8) Uani d . 1 . . O
O3 .01368(10) .01930(11) .11193(14) .0711(5) Uani d . 1 . . O
O1W .27048(12) -.07556(15) .47128(16) .0761(5) Uani d . 1 . . O
HWA .3006(18) -.025(2) .509(3) .085(9) Uiso d . 1 . . H
HWB .294(2) -.098(2) .446(3) .114(12) Uiso d . 1 . . H
C1 .19224(15) .26294(18) .1572(2) .0676(6) Uani d . 1 . . C
C1A .17132(13) .22895(14) .21847(17) .0558(5) Uani d . 1 . . C
C2 .2088(2) .1891(2) .1077(3) .0911(9) Uani d . 1 . . C
H2A .1614 .1763 .0322 .109 Uiso calc R 1 . . H
H2B .2464 .2156 .1055 .109 Uiso calc R 1 . . H
C3 .2390(2) .0973(2) .1697(3) .0950(9) Uani d . 1 . . C
H3A .2910 .1077 .2403 .114 Uiso calc R 1 . . H
H3B .2423 .0502 .1290 .114 Uiso calc R 1 . . H
C4 .18877(16) .05684(17) .1894(2) .0677(6) Uani d . 1 . . C
H4A .1416 .0303 .1210 .081 Uiso calc R 1 . . H
H4B .2162 .0048 .2429 .081 Uiso calc R 1 . . H
C4A .16805(12) .13331(14) .23127(16) .0527(5) Uani d . 1 . . C
C5 .13821(16) .32860(19) .4007(2) .0752(7) Uani d . 1 . . C
C5A .14027(12) .26131(16) .33461(17) .0573(5) Uani d . 1 . . C
C6 .1286(3) .2902(3) .4756(3) .1134(12) Uani d . 1 . . C
H6A .1781 .2955 .5508 .136 Uiso calc R 1 . . H
H6B .0921 .3313 .4695 .136 Uiso calc R 1 . . H
C7 .1032(3) .1953(3) .4580(4) .153(2) Uani d . 1 . . C
H7A .0471 .1974 .4081 .183 Uiso calc R 1 . . H
H7B .1220 .1710 .5280 .183 Uiso calc R 1 . . H
C8 .12297(17) .12158(19) .4140(2) .0735(7) Uani d . 1 . . C
H8A .0813 .0746 .3709 .088 Uiso calc R 1 . . H
H8B .1697 .0877 .4752 .088 Uiso calc R 1 . . H
C8A .13548(11) .16539(15) .34328(16) .0522(5) Uani d . 1 . . C
C9 .14962(18) .30370(16) .2601(2) .0739(7) Uani d . 1 . . C
H9A .1895 .3532 .2999 .089 Uiso calc R 1 . . H
H9B .1014 .3343 .1978 .089 Uiso calc R 1 . . H
N10 .14564(11) .10201(11) .28778(15) .0575(5) Uani d . 1 . . N
N11 .13047(11) .00379(11) .28438(15) .0568(5) Uani d . 1 . . N
H11 .1626 -.0326 .3410 .068 Uiso calc R 1 . . H
C12 .06327(12) -.03293(14) .18885(16) .0510(5) Uani d . 1 . . C
C13 .05681(11) -.13969(14) .18533(15) .0481(5) Uani d . 1 . . C
C14 .01321(13) -.18396(16) .08280(18) .0620(6) Uani d . 1 . . C
H14 -.0110 -.1465 .0199 .074 Uiso calc R 1 . . H
C15 .00567(15) -.28268(17) .0739(2) .0698(6) Uani d . 1 . . C
H15 -.0231 -.3112 .0047 .084 Uiso calc R 1 . . H
C16 .03971(14) -.34104(16) .1652(2) .0673(6) Uani d . 1 . . C
C17 .08318(16) -.29647(17) .2667(2) .0740(7) Uani d . 1 . . C
H17 .1069 -.3340 .3294 .089 Uiso calc R 1 . . H
C18 .09226(14) -.19757(16) .27738(18) .0639(6) Uani d . 1 . . C
H18 .1224 -.1694 .3470 .077 Uiso calc R 1 . . H
C19 .0291(2) -.44942(19) .1527(3) .1095(12) Uani d . 1 . . C
H19A .0484 -.4740 .1199 .164 Uiso calc R 1 . . H
H19B -.0250 -.4647 .1062 .164 Uiso calc R 1 . . H
H19C .0573 -.4784 .2240 .164 Uiso calc 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 .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 119.2(2) yes
O1 C1 C2 122.3(2) yes
C1A C1 C2 118.4(2) ?
C4A C1A C1 120.2(2) ?
C4A C1A C9 122.3(2) ?
C1 C1A C9 117.34(19) ?
C3 C2 C1 113.0(2) ?
C3 C2 H2A 109.0 ?
C1 C2 H2A 109.0 ?
C3 C2 H2B 109.0 ?
C1 C2 H2B 109.0 ?
H2A C2 H2B 107.8 ?
C2 C3 C4 112.7(3) ?
C2 C3 H3A 109.1 ?
C4 C3 H3A 109.1 ?
C2 C3 H3B 109.1 ?
C4 C3 H3B 109.1 ?
H3A C3 H3B 107.8 ?
C4A C4 C3 111.4(2) ?
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 119.36(19) yes
C1A C4A C4 123.5(2) ?
N10 C4A C4 117.18(17) yes
O2 C5 C5A 120.3(3) yes
O2 C5 C6 120.8(2) yes
C5A C5 C6 118.9(3) ?
C8A C5A C5 120.5(2) ?
C8A C5A C9 122.71(19) ?
C5 C5A C9 116.8(2) ?
C7 C6 C5 116.6(3) ?
C7 C6 H6A 108.1 ?
C5 C6 H6A 108.1 ?
C7 C6 H6B 108.1 ?
C5 C6 H6B 108.1 ?
H6A C6 H6B 107.3 ?
C6 C7 C8 121.5(3) ?
C6 C7 H7A 107.0 ?
C8 C7 H7A 107.0 ?
C6 C7 H7B 107.0 ?
C8 C7 H7B 107.0 ?
H7A C7 H7B 106.7 ?
C7 C8 C8A 112.2(2) ?
C7 C8 H8A 109.2 ?
C8A C8 H8A 109.2 ?
C7 C8 H8B 109.2 ?
C8A C8 H8B 109.2 ?
H8A C8 H8B 107.9 ?
C5A C8A N10 119.38(19) yes
C5A C8A C8 123.6(2) ?
N10 C8A C8 116.99(19) yes
C5A C9 C1A 112.11(18) ?
C5A C9 H9A 109.2 ?
C1A C9 H9A 109.2 ?
C5A C9 H9B 109.2 ?
C1A C9 H9B 109.2 ?
H9A C9 H9B 107.9 ?
C8A N10 N11 119.41(17) yes
C8A N10 C4A 122.43(16) yes
N11 N10 C4A 118.12(16) yes
C12 N11 N10 118.22(17) yes
C12 N11 H11 120.9 ?
N10 N11 H11 120.9 ?
O3 C12 N11 121.54(19) yes
O3 C12 C13 123.35(19) yes
N11 C12 C13 115.09(16) yes
C18 C13 C14 118.37(19) ?
C18 C13 C12 124.28(18) ?
C14 C13 C12 117.34(17) ?
C15 C14 C13 120.3(2) ?
C15 C14 H14 119.9 ?
C13 C14 H14 119.9 ?
C14 C15 C16 121.8(2) ?
C14 C15 H15 119.1 ?
C16 C15 H15 119.1 ?
C17 C16 C15 117.5(2) ?
C17 C16 C19 121.9(2) ?
C15 C16 C19 120.6(2) ?
C18 C17 C16 121.5(2) ?
C18 C17 H17 119.3 ?
C16 C17 H17 119.3 ?
C17 C18 C13 120.5(2) ?
C17 C18 H18 119.7 ?
C13 C18 H18 119.7 ?
C16 C19 H19A 109.5 ?
C16 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C16 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 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
O1 C1 . 1.234(3) yes
O2 C5 . 1.231(3) yes
O3 C12 . 1.219(2) yes
C1 C1A . 1.453(3) yes
C1 C2 . 1.504(4) ?
C1A C4A . 1.350(3) yes
C1A C9 . 1.499(3) yes
C2 C3 . 1.476(4) ?
C2 H2A . .9700 ?
C2 H2B . .9700 ?
C3 C4 . 1.511(4) ?
C3 H3A . .9700 ?
C3 H3B . .9700 ?
C4 C4A . 1.503(3) yes
C4 H4A . .9700 ?
C4 H4B . .9700 ?
C4A N10 . 1.398(3) yes
C5 C5A . 1.450(3) yes
C5 C6 . 1.480(5) ?
C5A C8A . 1.347(3) yes
C5A C9 . 1.491(3) yes
C6 C7 . 1.389(5) ?
C6 H6A . .9700 ?
C6 H6B . .9700 ?
C7 C8 . 1.487(4) ?
C7 H7A . .9700 ?
C7 H7B . .9700 ?
C8 C8A . 1.495(3) yes
C8 H8A . .9700 ?
C8 H8B . .9700 ?
C8A N10 . 1.390(3) yes
C9 H9A . .9700 ?
C9 H9B . .9700 ?
N10 N11 . 1.395(2) yes
N11 C12 . 1.364(3) yes
N11 H11 . .8600 ?
C12 C13 . 1.482(3) ?
C13 C18 . 1.385(3) ?
C13 C14 . 1.389(3) ?
C14 C15 . 1.372(3) ?
C14 H14 . .9300 ?
C15 C16 . 1.384(3) ?
C15 H15 . .9300 ?
C16 C17 . 1.379(3) ?
C16 C19 . 1.511(3) ?
C17 C18 . 1.377(3) ?
C17 H17 . .9300 ?
C18 H18 . .9300 ?
C19 H19A . .9600 ?
C19 H19B . .9600 ?
C19 H19C . .9600 ?
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 1_555 .86 2.001 2.789(2) 151.8
C8 H8A O3 2_555 .97 2.522 3.2340(10) 130.0
O1W HWB O1 4_545 .93 1.828 2.730(5) 162.0
O1W HWA O2 7_556 .88 1.897 2.763(3) 166.2
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 176.8(2)
C2 C1 C1A C4A .9(3)
O1 C1 C1A C9 .1(3)
C2 C1 C1A C9 -175.8(2)
O1 C1 C2 C3 155.7(3)
C1A C1 C2 C3 -28.5(4)
C1 C2 C3 C4 51.7(4)
C2 C3 C4 C4A -47.1(4)
C1 C1A C4A N10 -178.2(2)
C9 C1A C4A N10 -1.7(3)
C1 C1A C4A C4 2.9(3)
C9 C1A C4A C4 179.4(2)
C3 C4 C4A C1A 20.2(3)
C3 C4 C4A N10 -158.7(2)
O2 C5 C5A C8A 175.6(2)
C6 C5 C5A C8A -1.6(4)
O2 C5 C5A C9 -3.1(4)
C6 C5 C5A C9 179.7(3)
O2 C5 C6 C7 167.4(4)
C5A C5 C6 C7 -15.4(5)
C5 C6 C7 C8 31.1(7)
C6 C7 C8 C8A -27.9(6)
C5 C5A C8A N10 -173.4(2)
C9 C5A C8A N10 5.2(3)
C5 C5A C8A C8 3.9(3)
C9 C5A C8A C8 -177.5(2)
C7 C8 C8A C5A 9.7(4)
C7 C8 C8A N10 -173.0(3)
C8A C5A C9 C1A -13.3(3)
C5 C5A C9 C1A 165.3(2)
C4A C1A C9 C5A 11.4(3)
C1 C1A C9 C5A -172.0(2)
C5A C8A N10 N11 -171.42(19)
C8 C8A N10 N11 11.1(3)
C5A C8A N10 C4A 6.2(3)
C8 C8A N10 C4A -171.2(2)
C1A C4A N10 C8A -8.0(3)
C4 C4A N10 C8A 171.0(2)
C1A C4A N10 N11 169.70(19)
C4 C4A N10 N11 -11.4(3)
C8A N10 N11 C12 103.8(2)
C4A N10 N11 C12 -74.0(2)
N10 N11 C12 O3 -7.5(3)
N10 N11 C12 C13 170.87(17)
O3 C12 C13 C18 -152.9(2)
N11 C12 C13 C18 28.8(3)
O3 C12 C13 C14 28.2(3)
N11 C12 C13 C14 -150.11(19)
C18 C13 C14 C15 .2(3)
C12 C13 C14 C15 179.2(2)
C13 C14 C15 C16 1.0(4)
C14 C15 C16 C17 -1.2(4)
C14 C15 C16 C19 178.8(3)
C15 C16 C17 C18 .3(4)
C19 C16 C17 C18 -179.7(3)
C16 C17 C18 C13 .8(4)
C14 C13 C18 C17 -1.1(3)
C12 C13 C18 C17 180.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21135568
