#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/02/2010278.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_2010278
loop_
_publ_author_name
'Sivaraman, J.'
'Subramanian, K.'
'Velmurugan, D.'
'Subramanian, E.'
'Ramakrishanan, V.T.'
_publ_section_title
9-Methyl-10-(4-methylphenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2011
_journal_page_last               2013
_journal_paper_doi               10.1107/S0108270194002805
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C21 H23 N1 O2'
_chemical_formula_sum            'C21 H23 N O2'
_chemical_formula_weight         321.4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 102.80(10)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   9.1080(10)
_cell_length_b                   11.405(2)
_cell_length_c                   17.482(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293
_cell_measurement_theta_max      25
_cell_measurement_theta_min      15
_cell_volume                     1770.8(8)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.021
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3000
_diffrn_reflns_theta_max         60
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.57
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'deep red'
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      1.210
_exptl_crystal_description       'rectangular blocks'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.5
_refine_diff_density_min         -0.4
_refine_ls_goodness_of_fit_obs   1.105
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     309
_refine_ls_number_reflns         2611
_refine_ls_R_factor_obs          0.066
_refine_ls_shift/esd_max         0.085
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.008779F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.069
_reflns_number_observed          2611
_reflns_number_total             2831
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            ha1062.cif
_cod_data_source_block           ha1062a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F) + 0.008779F^2^]'
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^(F) +
0.008779F^2^]'.

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_original_formula_sum        'C21 H23 N1 O2'
_cod_database_code               2010278
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
C(1) 1.0415(3) .2023(2) -.05240(10)
C(2) 1.1861(5) .1736(5) -.0749(2)
C(3) 1.2797(5) .0868(4) -.0332(2)
C(4) 1.2906(3) .0839(2) .0540(2)
C(4)a 1.1670(2) .1343(2) .08330(10)
O(4) 1.3982(2) .0373(2) .09870(10)
C(5) 1.1770(3) .1307(2) .17020(10)
C(5)' 1.2732(3) .2301(3) .2113(2)
C(5)a 1.0204(3) .1363(2) .18540(10)
C(6) .9911(3) .0814(3) .25570(10)
O(6) 1.0896(3) .0275(3) .30080(10)
C(7) .8353(3) .0910(3) .2708(2)
C(8) .7615(3) .2046(4) .2398(2)
C(9) .7577(3) .2182(3) .15340(10)
C(9)a .9079(2) .1934(2) .13530(10)
N(10) .9278(2) .2296(2) .06180(10)
C(10)a 1.0508(3) .1884(2) .03420(10)
C(11) .8151(2) .3021(2) .01230(10)
C(12) .6948(3) .2511(2) -.03850(10)
C(13) .5891(3) .3230(3) -.08700(10)
C(14) .6026(3) .4435(2) -.08430(10)
C(14)' .4891(4) .5199(3) -.1377(2)
C(15) .7244(3) .4923(2) -.03270(10)
C(16) .8305(3) .4220(2) .01660(10)
H(1)a 0.963(4) 0.154(3) -.073(2)
H(1)b 1.016(4) .281(3) -.071(2)
H(2)a 1.269(4) .250(3) -.060(2)
H(2)b 1.156(3) .158(3) -.138(2)
H(3)a 1.218(4) .003(3) -.059(2)
H(3)b 1.380(4) .073(3) -.044(2)
H(5) 1.2190(10) .050(2) .1870(10)
H(5)'a 1.284(4) .234(3) .268(2)
H(5)'b 1.228(3) .315(3) .180(2)
H(5)'c 1.381(3) .234(2) .196(2)
H(7)a .838(3) .070(2) .3330(10)
H(7)b .781(4) .031(3) .243(2)
H(8)a .663(4) .208(3) .246(2)
H(8)b .830(4) .269(3) .269(2)
H(9)a .732(3) .304(2) .1350(10)
H(9)b .677(2) .164(2) .1170(10)
H(12) .678(3) .166(2) -.0460(10)
H(13) .497(3) .275(3) -.127(2)
H(14)a .400(4) .475(3) -.164(2)
H(14)b .536(4) .560(3) -.177(2)
H(14)c .460(4) .590(3) -.103(2)
H(15) .750(4) .583(3) -.029(2)
H(16) .912(4) .467(3) .051(2)
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
C(2) C(1) C(10)a 112.7(2) yes
C(1) C(2) C(3) 119.3(3) yes
C(2) C(3) C(4) 116.0(4) yes
C(3) C(4) O(4) 121.1(3) yes
C(3) C(4) C(4)a 117.7(3) yes
C(4)a C(4) O(4) 121.1(3) yes
C(4) C(4)a C(10)a 120.9(2) yes
C(4) C(4)a C(5) 117.9(2) yes
C(5) C(4)a C(10)a 121.1(2) yes
C(4)a C(5) C(5)a 109.2(2) yes
C(4)a C(5) C(5)' 111.0(2) yes
C(5)' C(5) C(5)a 110.8(2) yes
C(5) C(5)a C(9)a 121.0(2) yes
C(5) C(5)a C(6) 119.2(2) yes
C(6) C(5)a C(9)a 119.8(2) yes
C(5)a C(6) C(7) 118.3(2) yes
C(5)a C(6) O(6) 121.1(2) yes
O(6) C(6) C(7) 120.7(2) yes
C(6) C(7) C(8) 111.3(3) yes
C(7) C(8) C(9) 111.0(3) yes
C(8) C(9) C(9)a 111.8(2) yes
C(5)a C(9)a C(9) 123.3(2) yes
C(9) C(9)a N(10) 116.7(2) yes
C(5)a C(9)a N(10) 120.1(2) yes
C(9)a N(10) C(11) 119.9(2) yes
C(9)a N(10) C(10)a 119.7(2) yes
C(10)a N(10) C(11) 120.2(2) yes
C(4)a C(10)a N(10) 120.6(2) yes
C(1) C(10)a N(10) 116.2(2) yes
C(1) C(10)a C(4)a 123.2(2) yes
N(10) C(11) C(16) 119.0(2) yes
N(10) C(11) C(12) 120.1(2) yes
C(12) C(11) C(16) 120.8(2) yes
C(11) C(12) C(13) 119.1(2) yes
C(12) C(13) C(14) 121.3(2) yes
C(13) C(14) C(15) 118.4(2) yes
C(13) C(14) C(14)' 120.7(2) yes
C(14)' C(14) C(15) 120.8(2) yes
C(14) C(15) C(16) 121.1(2) yes
C(11) C(16) C(15) 119.3(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(2) 1.492(6) yes
C(1) C(10)a 1.506(3) yes
C(2) C(3) 1.401(6) yes
C(3) C(4) 1.506(5) yes
C(4) C(4)a 1.455(4) yes
C(4) O(4) 1.231(3) yes
C(4)a C(5) 1.502(3) yes
C(4)a C(10)a 1.355(3) yes
C(5) C(5)' 1.513(4) yes
C(5) C(5)a 1.509(4) yes
C(5)a C(6) 1.456(3) yes
C(5)a C(9)a 1.358(3) yes
C(6) O(6) 1.221(4) yes
C(6) C(7) 1.504(4) yes
C(7) C(8) 1.504(5) yes
C(8) C(9) 1.511(4) yes
C(9) C(9)a 1.498(3) yes
C(9)a N(10) 1.399(3) yes
N(10) C(10)a 1.396(3) yes
N(10) C(11) 1.447(3) yes
C(11) C(12) 1.377(3) yes
C(11) C(16) 1.375(3) yes
C(12) C(13) 1.399(3) yes
C(13) C(14) 1.380(4) yes
C(14) C(14)' 1.507(4) yes
C(14) C(15) 1.382(3) yes
C(15) C(16) 1.397(3) yes
C(1) H(1)a 0.91(3) no
C(1) H(1)b 0.97(4) no
C(2) H(2)a 1.14(4) no
C(2) H(2)b 1.09(3) no
C(3) H(3)a 1.15(3) no
C(3) H(3)b 0.99(4) no
C(5) H(5) 1.02(2) no
C(5)' H(5)'a 0.98(3) no
C(5)' H(5)'b 1.14(3) no
C(5)' H(5)'c 1.07(3) no
C(7) H(7)a 1.10(3) no
C(7) H(7)b 0.92(3) no
C(8) H(8)a 0.93(3) no
C(8) H(8)b 1.02(3) no
C(9) H(9)a 1.04(3) no
C(9) H(9)b 1.06(2) no
C(12) H(12) 0.98(3) no
C(13) H(13) 1.10(3) no
C(14)' H(14)a 0.98(4) no
C(14)' H(14)b 0.99(4) no
C(14)' H(14)c 1.07(4) no
C(15) H(15) 1.06(3) no
C(16) H(16) 0.99(3) no
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
C(2) C(1) C(10)a C(4)a -12.1(4) yes
C(10)a C(1) C(2) C(3) 32.6(5) yes
C(1) C(2) C(3) C(4) -38.7(6) yes
C(2) C(3) C(4) C(4)a 23.6(5) yes
C(3) C(4) C(4)a C(10)a -4.0(4) yes
C(4) C(4)a C(10)a C(1) -1.1(4) yes
C(5) C(4)a C(10)a N(10) -8.0(3) yes
C(10)a C(4)a C(5) C(5)a 27.9(3) yes
C(4)a C(5) C(5)a C(9)a -29.8(3) yes
C(5) C(5)a C(9)a N(10) 11.6(3) yes
C(5)a C(9)a N(10) C(10)a 11.9(3) yes
C(9)a N(10) C(10)a C(4)a -13.9(3) yes
C(6) C(5)a C(9)a C(9) 8.8(4) yes
C(9)a C(5)a C(6) C(7) -0.5(4) yes
C(5)a C(6) C(7) C(8) -32.0(4) yes
C(6) C(7) C(8) C(9) 56.2(4) yes
C(7) C(8) C(9) C(9)a -48.4(3) yes
C(8) C(9) C(9)a C(5)a 16.3(3) yes
C(2) C(1) C(10)a C(4)a -12.1(4) no
C(2) C(1) C(10)a N(10) 171.0(3) no
C(10)a C(1) C(2) C(3) 32.6(5) no
C(1) C(2) C(3) C(4) 38.7(6) no
C(2) C(3) C(4) C(4)a 23.6(5) no
C(2) C(3) C(4) O(4) -158.6(4) no
C(3) C(4) C(4)a C(5) 179.5(3) no
C(3) C(4) C(4)a C(10)a -4.0(4) no
O(4) C(4) C(4)a C(10)a 178.2(2) no
O(4) C(4) C(4)a C(5) 1.7(4) no
C(4) C(4)a C(10)a C(1) -1.1(4) no
C(5) C(4)a C(10)a C(1) 175.3(2) no
C(4) C(4)a C(10)a N(10) 175.7(2) no
C(4) C(4)a C(5) C(5)' 81.9(3) no
C(4) C(4)a C(5) C(5)a -155.6(2) no
C(5) C(4)a C(10)a N(10) -8.0(3) no
C(10)a C(4)a C(5) C(5)a 27.9(3) no
C(10)a C(4)a C(5) C(5)' -94.5(3) no
C(4)a C(5) C(5)a C(6) 151.4(2) no
C(4)a C(5) C(5)a C(9)a -29.8(3) no
C(5)' C(5) C(5)a C(6) -86.0(3) no
C(5)' C(5) C(5)a C(9)a 92.8(3) no
C(5) C(5)a C(9)a N(10) 11.6(3) no
C(5) C(5)a C(9)a C(9) -170.0(2) no
C(5) C(5)a C(6) O(6) -2.7(4) no
C(5) C(5)a C(6) C(7) 178.3(2) no
C(6) C(5)a C(9)a N(10) -169.6(2) no
C(6) C(5)a C(9)a C(9) 8.8(4) no
C(9)a C(5)a C(6) C(7) -0.5(4) no
C(9)a C(5)a C(6) O(6) 178.5(3) no
C(5)a C(6) C(7) C(8) -32.0(4) no
O(6) C(6) C(7) C(8) 149.0(3) no
C(6) C(7) C(8) C(9) 56.2(4) no
C(7) C(8) C(9) C(9)a -48.4(3) no
C(8) C(9) C(9)a C(5)a 16.3(3) no
C(8) C(9) C(9)a N(10) -165.3(2) no
C(9) C(9)a N(10) C(10)a -166.5(2) no
C(5)a C(9)a N(10) C(10)a 11.9(3) no
C(9) C(9)a N(10) C(11) 8.7(3) no
C(5)a C(9)a N(10) C(11) -172.8(2) no
C(9)a N(10) C(10)a C(4)a -13.9(3) no
C(9)a N(10) C(10)a C(1) 163.1(2) no
C(9)a N(10) C(11) C(12) -87.8(3) no
C(9)a N(10) C(11) C(16) 92.5(3) no
C(11) N(10) C(10)a C(4)a 170.9(2) no
C(11) N(10) C(10)a C(1) -12.1(3) no
C(10)a N(10) C(11) C(12) 87.5(3) no
C(10)a N(10) C(11) C(16) -92.2(3) no
N(10) C(11) C(16) C(15) 178.1(2) no
N(10) C(11) C(12) C(13) -178.6(2) no
C(12) C(11) C(16) C(15) -1.6(3) no
C(16) C(11) C(12) C(13) 1.1(3) no
C(11) C(12) C(13) C(14) -0.6(4) no
C(12) C(13) C(14) C(14)' 179.1(3) no
C(12) C(13) C(14) C(15) 0.5(4) no
C(13) C(14) C(15) C(16) -1.0(4) no
C(14) C(15) C(16) C(11) 1.5(4) no
