#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/63/2206390.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_2206390
loop_
_publ_author_name
'Shujiang Tu'
'Bo Jiang'
'Xiang Zou'
'Tuanjie Li'
_publ_section_title
;
 9-(4-Bromophenyl)-3,3,7-trimethyl-3,4-dihydroacridin-1(2H)-one
;
_journal_coeditor_code           CV6527
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2570
_journal_page_last               o2572
_journal_paper_doi               10.1107/S1600536805022270
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C22 H20 Br N O'
_chemical_formula_moiety         'C22 H20 Br N O'
_chemical_formula_sum            'C22 H20 Br N O'
_chemical_formula_weight         394.30
_chemical_melting_point          .513E-305
_chemical_name_systematic
;
9-(4-Bromophenyl)-3,3,7-trimethyl-3,4-dihydroacridin-1(2H)-one
;
_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                111.134(2)
_cell_angle_beta                 112.428(3)
_cell_angle_gamma                99.831(3)
_cell_formula_units_Z            2
_cell_length_a                   10.045(2)
_cell_length_b                   10.247(2)
_cell_length_c                   11.261(2)
_cell_measurement_reflns_used    2153
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.185
_cell_measurement_theta_min      2.213
_cell_volume                     933.3(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4925
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    2.211
_exptl_absorpt_correction_T_max  0.6539
_exptl_absorpt_correction_T_min  0.4498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.520
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0323
_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)+(0.0469P)²+0.1846P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0856
_reflns_number_gt                2609
_reflns_number_total             3255
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6527.cif
_cod_data_source_block           I
_cod_original_cell_volume        933.3(4)
_cod_database_code               2206390
_cod_database_fobs_code          2206390
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_type_symbol
Br1 0.09824(4) 0.89628(3) 1.14806(3) 0.06064(14) Uani d . 1 Br
N1 0.0848(2) 0.1489(2) 0.4077(2) 0.0394(5) Uani d . 1 N
O1 -0.2132(2) 0.3159(2) 0.6346(2) 0.0648(6) Uani d . 1 O
C1 -0.1941(3) 0.2204(3) 0.5477(3) 0.0402(6) Uani d . 1 C
C2 -0.3163(3) 0.0677(3) 0.4444(3) 0.0515(7) Uani d . 1 C
H2A -0.4145 0.0731 0.4367 0.062 Uiso calc R 1 H
H2B -0.2926 -0.0002 0.4841 0.062 Uiso calc R 1 H
C3 -0.3320(3) 0.0036(3) 0.2926(3) 0.0492(7) Uani d . 1 C
C4 -0.1760(3) -0.0061(3) 0.3094(3) 0.0478(7) Uani d . 1 C
H4A -0.1616 -0.0862 0.3337 0.057 Uiso calc R 1 H
H4B -0.1782 -0.0326 0.2167 0.057 Uiso calc R 1 H
C5 0.3484(3) 0.2846(3) 0.4953(3) 0.0490(7) Uani d . 1 C
H5A 0.3461 0.2100 0.4162 0.059 Uiso calc R 1 H
C6 0.4809(3) 0.4037(3) 0.5954(3) 0.0530(7) Uani d . 1 C
H6A 0.5681 0.4088 0.5837 0.064 Uiso calc R 1 H
C7 0.4900(3) 0.5205(3) 0.7173(3) 0.0472(7) Uani d . 1 C
C8 0.3603(3) 0.5117(3) 0.7324(3) 0.0395(6) Uani d . 1 C
H8A 0.3647 0.5882 0.8115 0.047 Uiso calc R 1 H
C9 0.2193(3) 0.3888(3) 0.6304(2) 0.0328(5) Uani d . 1 C
C10 0.0826(3) 0.3750(2) 0.6430(2) 0.0308(5) Uani d . 1 C
C11 -0.0469(3) 0.2467(2) 0.5399(2) 0.0320(5) Uani d . 1 C
C12 -0.0398(3) 0.1358(3) 0.4232(2) 0.0352(5) Uani d . 1 C
C13 0.2138(3) 0.2727(3) 0.5100(3) 0.0361(5) Uani d . 1 C
C14 -0.3761(4) 0.1052(4) 0.2256(4) 0.0791(11) Uani d . 1 C
H14A -0.2979 0.2034 0.2855 0.119 Uiso calc R 1 H
H14B -0.4728 0.1114 0.2187 0.119 Uiso calc R 1 H
H14C -0.3855 0.0648 0.1302 0.119 Uiso calc R 1 H
C15 -0.4559(4) -0.1536(4) 0.1970(4) 0.0790(10) Uani d . 1 C
H15A -0.5538 -0.1476 0.1865 0.119 Uiso calc R 1 H
H15B -0.4296 -0.2162 0.2415 0.119 Uiso calc R 1 H
H15C -0.4620 -0.1955 0.1030 0.119 Uiso calc R 1 H
C16 0.6403(3) 0.6489(4) 0.8257(4) 0.0696(9) Uani d . 1 C
H16A 0.6279 0.7182 0.9013 0.104 Uiso calc R 1 H
H16B 0.6713 0.6989 0.7778 0.104 Uiso calc R 1 H
H16C 0.7178 0.6116 0.8670 0.104 Uiso calc R 1 H
C17 0.0855(3) 0.5001(2) 0.7658(2) 0.0318(5) Uani d . 1 C
C18 0.1400(3) 0.5089(3) 0.9022(3) 0.0387(6) Uani d . 1 C
H18A 0.1738 0.4345 0.9174 0.046 Uiso calc R 1 H
C19 0.1453(3) 0.6259(3) 1.0166(3) 0.0417(6) Uani d . 1 C
H19A 0.1814 0.6302 1.1077 0.050 Uiso calc R 1 H
C20 0.0960(3) 0.7363(3) 0.9928(3) 0.0389(6) Uani d . 1 C
C21 0.0435(3) 0.7321(3) 0.8587(3) 0.0458(6) Uani d . 1 C
H21A 0.0117 0.8078 0.8443 0.055 Uiso calc R 1 H
C22 0.0389(3) 0.6138(3) 0.7459(3) 0.0427(6) Uani d . 1 C
H22A 0.0041 0.6105 0.6552 0.051 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 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'
Br Br -0.2901 2.4595 '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
C12 N1 C13 118.2(2) yes
O1 C1 C11 122.1(2) ?
O1 C1 C2 121.3(2) ?
C11 C1 C2 116.5(2) ?
C1 C2 C3 113.7(2) yes
C1 C2 H2A 108.8 ?
C3 C2 H2A 108.8 ?
C1 C2 H2B 108.8 ?
C3 C2 H2B 108.8 ?
H2A C2 H2B 107.7 ?
C14 C3 C2 109.7(3) ?
C14 C3 C4 111.2(3) ?
C2 C3 C4 107.0(2) yes
C14 C3 C15 109.7(2) ?
C2 C3 C15 109.7(3) ?
C4 C3 C15 109.5(2) ?
C12 C4 C3 114.6(2) yes
C12 C4 H4A 108.6 ?
C3 C4 H4A 108.6 ?
C12 C4 H4B 108.6 ?
C3 C4 H4B 108.6 ?
H4A C4 H4B 107.6 ?
C6 C5 C13 120.6(2) ?
C6 C5 H5A 119.7 ?
C13 C5 H5A 119.7 ?
C5 C6 C7 121.8(2) ?
C5 C6 H6A 119.1 ?
C7 C6 H6A 119.1 ?
C8 C7 C6 118.4(2) ?
C8 C7 C16 122.2(3) ?
C6 C7 C16 119.5(3) ?
C7 C8 C9 121.7(2) ?
C7 C8 H8A 119.1 ?
C9 C8 H8A 119.1 ?
C13 C9 C8 118.7(2) ?
C13 C9 C10 117.9(2) yes
C8 C9 C10 123.4(2) ?
C11 C10 C9 118.4(2) ?
C11 C10 C17 123.4(2) ?
C9 C10 C17 118.2(2) ?
C10 C11 C12 119.2(2) ?
C10 C11 C1 121.9(2) ?
C12 C11 C1 118.8(2) yes
N1 C12 C11 123.1(2) yes
N1 C12 C4 115.4(2) ?
C11 C12 C4 121.5(2) ?
N1 C13 C5 118.1(2) ?
N1 C13 C9 123.2(2) yes
C5 C13 C9 118.8(2) ?
C3 C14 H14A 109.5 ?
C3 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C3 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C3 C15 H15A 109.5 ?
C3 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C3 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C7 C16 H16A 109.5 ?
C7 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C7 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C18 C17 C22 118.5(2) ?
C18 C17 C10 121.3(2) ?
C22 C17 C10 120.1(2) ?
C17 C18 C19 121.4(2) ?
C17 C18 H18A 119.3 ?
C19 C18 H18A 119.3 ?
C20 C19 C18 118.7(2) ?
C20 C19 H19A 120.7 ?
C18 C19 H19A 120.7 ?
C19 C20 C21 121.3(2) ?
C19 C20 Br1 119.29(19) ?
C21 C20 Br1 119.42(19) ?
C20 C21 C22 119.0(2) ?
C20 C21 H21A 120.5 ?
C22 C21 H21A 120.5 ?
C21 C22 C17 121.1(2) ?
C21 C22 H22A 119.5 ?
C17 C22 H22A 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C20 1.906(2) ?
N1 C12 1.320(3) yes
N1 C13 1.364(3) yes
O1 C1 1.212(3) ?
C1 C11 1.500(3) ?
C1 C2 1.500(4) ?
C2 C3 1.526(4) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C14 1.523(4) ?
C3 C4 1.530(4) ?
C3 C15 1.531(4) ?
C4 C12 1.506(3) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C6 1.357(4) ?
C5 C13 1.415(3) ?
C5 H5A 0.9300 ?
C6 C7 1.417(4) ?
C6 H6A 0.9300 ?
C7 C8 1.369(4) ?
C7 C16 1.503(4) ?
C8 C9 1.421(3) ?
C8 H8A 0.9300 ?
C9 C13 1.419(3) yes
C9 C10 1.421(3) yes
C10 C11 1.390(3) yes
C10 C17 1.496(3) ?
C11 C12 1.430(3) yes
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
C17 C18 1.381(3) ?
C17 C22 1.385(3) ?
C18 C19 1.383(3) ?
C18 H18A 0.9300 ?
C19 C20 1.380(4) ?
C19 H19A 0.9300 ?
C20 C21 1.378(4) ?
C21 C22 1.383(3) ?
C21 H21A 0.9300 ?
C22 H22A 0.9300 ?
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
O1 C1 C2 C3 141.1(3) ?
C11 C1 C2 C3 -40.3(3) ?
C1 C2 C3 C14 -61.0(3) yes
C1 C2 C3 C4 59.7(3) yes
C1 C2 C3 C15 178.4(3) ?
C14 C3 C4 C12 69.6(3) ?
C2 C3 C4 C12 -50.1(3) yes
C15 C3 C4 C12 -169.0(2) ?
C13 C5 C6 C7 -0.3(4) ?
C5 C6 C7 C8 -0.4(4) ?
C5 C6 C7 C16 179.4(3) ?
C6 C7 C8 C9 0.7(4) ?
C16 C7 C8 C9 -179.1(2) ?
C7 C8 C9 C13 -0.1(4) ?
C7 C8 C9 C10 179.5(2) ?
C13 C9 C10 C11 2.2(3) ?
C8 C9 C10 C11 -177.3(2) ?
C13 C9 C10 C17 -177.3(2) ?
C8 C9 C10 C17 3.1(3) ?
C9 C10 C11 C12 -1.8(3) ?
C17 C10 C11 C12 177.67(19) ?
C9 C10 C11 C1 177.8(2) ?
C17 C10 C11 C1 -2.7(3) ?
O1 C1 C11 C10 8.1(4) ?
C2 C1 C11 C10 -170.6(2) ?
O1 C1 C11 C12 -172.3(2) ?
C2 C1 C11 C12 9.1(3) yes
C13 N1 C12 C11 1.7(3) yes
C13 N1 C12 C4 -177.9(2) ?
C10 C11 C12 N1 -0.2(3) yes
C1 C11 C12 N1 -179.8(2) ?
C10 C11 C12 C4 179.4(2) ?
C1 C11 C12 C4 -0.3(3) yes
C3 C4 C12 N1 -158.0(2) ?
C3 C4 C12 C11 22.4(3) yes
C12 N1 C13 C5 178.3(2) ?
C12 N1 C13 C9 -1.2(4) yes
C6 C5 C13 N1 -178.7(2) ?
C6 C5 C13 C9 0.9(4) ?
C8 C9 C13 N1 178.8(2) ?
C10 C9 C13 N1 -0.7(3) yes
C8 C9 C13 C5 -0.7(3) ?
C10 C9 C13 C5 179.7(2) ?
C11 C10 C17 C18 96.3(3) ?
C9 C10 C17 C18 -84.2(3) ?
C11 C10 C17 C22 -86.5(3) ?
C9 C10 C17 C22 93.0(3) ?
C22 C17 C18 C19 1.5(4) ?
C10 C17 C18 C19 178.8(2) ?
C17 C18 C19 C20 -0.6(4) ?
C18 C19 C20 C21 -0.6(4) ?
C18 C19 C20 Br1 178.66(18) ?
C19 C20 C21 C22 0.7(4) ?
Br1 C20 C21 C22 -178.5(2) ?
C20 C21 C22 C17 0.3(4) ?
C18 C17 C22 C21 -1.4(4) ?
C10 C17 C22 C21 -178.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129161
