#------------------------------------------------------------------------------
#$Date: 2010-01-30 15:59:17 +0200 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2203332.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_2203332
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
'Qingjian Liu'
'Jianhua Xu'
_publ_section_title
;
9-Bromo-4-methyl-2-phenylbenzo[de]cyclobut[i]isoquinoline-3,5(2H)-dione
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o466
_journal_page_last               o467
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C21 H14 Br N O2'
_chemical_formula_moiety         'C21 H14 Br N O2'
_chemical_formula_sum            'C21 H14 Br N O2'
_chemical_formula_weight         392.24
_chemical_melting_point          458-459
_chemical_name_systematic
;
9-Bromo-4-methyl-2-phenylbenzo[de]cyclobut[i]
isoquinoline-3,5(2H)-dione
;
_symmetry_cell_setting           Monoclinic
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 104.88(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.589(2)
_cell_length_b                   19.126(4)
_cell_length_c                   10.176(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      11
_cell_volume                     1615.6(6)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3036
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        4.81
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.559
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.300
_refine_ls_extinction_coef       0.0108(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0481
_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/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1631
_reflns_number_gt                1527
_reflns_number_total             2840
_reflns_threshold_expression     I>2\s(I)
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_type_symbol
Br 0.32705(10) 0.57408(4) 0.15772(6) 0.0708(3) Uani d . 1 Br
O1 0.1191(5) 0.4793(2) 0.8228(4) 0.0639(12) Uani d . 1 O
O2 0.0019(5) 0.6979(2) 0.6597(4) 0.0530(11) Uani d . 1 O
N 0.0659(5) 0.5896(2) 0.7446(4) 0.0442(12) Uani d . 1 N
C1 0.3403(6) 0.6818(3) 0.6323(5) 0.0362(13) Uani d . 1 C
C2 0.3022(7) 0.7285(3) 0.5318(6) 0.0452(15) Uani d . 1 C
H2 0.348(6) 0.768(3) 0.517(5) 0.049(17) Uiso d . 1 H
C3 0.1602(7) 0.6884(3) 0.4467(5) 0.0466(15) Uani d . 1 C
H3A 0.0574 0.7134 0.4304 0.056 Uiso calc R 1 H
C4 0.1980(7) 0.6617(3) 0.3224(5) 0.0486(15) Uani d . 1 C
H4A 0.1782 0.6902 0.2459 0.058 Uiso calc R 1 H
C5 0.2591(7) 0.5986(3) 0.3157(5) 0.0435(14) Uani d . 1 C
C6 0.2691(6) 0.5443(3) 0.4198(5) 0.0393(13) Uani d . 1 C
C7 0.3169(7) 0.4752(3) 0.4040(6) 0.0468(15) Uani d . 1 C
H7A 0.3561 0.4637 0.3297 0.056 Uiso calc R 1 H
C8 0.3065(7) 0.4242(3) 0.4971(6) 0.0502(15) Uani d . 1 C
H8A 0.3408 0.3789 0.4863 0.060 Uiso calc R 1 H
C9 0.2458(7) 0.4399(3) 0.6051(6) 0.0489(15) Uani d . 1 C
H9A 0.2347 0.4050 0.6657 0.059 Uiso calc R 1 H
C10 0.2008(6) 0.5082(3) 0.6244(5) 0.0385(13) Uani d . 1 C
C11 0.2200(6) 0.5613(3) 0.5359(5) 0.0336(12) Uani d . 1 C
C12 0.1917(6) 0.6354(3) 0.5695(5) 0.0366(13) Uani d . 1 C
C13 0.0736(6) 0.6440(3) 0.6575(5) 0.0411(14) Uani d . 1 C
C14 0.1290(6) 0.5234(3) 0.7395(6) 0.0431(14) Uani d . 1 C
C15 0.4674(6) 0.6778(3) 0.7593(5) 0.0382(14) Uani d . 1 C
C16 0.4895(7) 0.6197(3) 0.8426(5) 0.0447(14) Uani d . 1 C
H16A 0.4223 0.5812 0.8180 0.054 Uiso calc R 1 H
C17 0.6105(7) 0.6182(3) 0.9622(6) 0.0521(16) Uani d . 1 C
H17A 0.6249 0.5786 1.0168 0.063 Uiso calc R 1 H
C18 0.7091(7) 0.6748(4) 1.0005(6) 0.0556(17) Uani d . 1 C
H18A 0.7884 0.6742 1.0822 0.067 Uiso calc R 1 H
C19 0.6902(7) 0.7322(4) 0.9179(7) 0.0628(18) Uani d . 1 C
H19A 0.7593 0.7701 0.9427 0.075 Uiso calc R 1 H
C20 0.5715(7) 0.7347(3) 0.7997(6) 0.0529(16) Uani d . 1 C
H20A 0.5594 0.7745 0.7455 0.063 Uiso calc R 1 H
C21 -0.0243(8) 0.6031(4) 0.8490(6) 0.0601(17) Uani d . 1 C
H21A -0.0226 0.5619 0.9031 0.090 Uiso calc R 1 H
H21B -0.1338 0.6150 0.8048 0.090 Uiso calc R 1 H
H21C 0.0253 0.6411 0.9062 0.090 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br 0.0999(7) 0.0714(5) 0.0474(4) 0.0078(4) 0.0300(4) 0.0001(3)
O1 0.077(3) 0.060(3) 0.058(3) 0.001(2) 0.022(2) 0.017(2)
O2 0.049(3) 0.047(3) 0.064(3) 0.012(2) 0.019(2) -0.005(2)
N 0.040(3) 0.051(3) 0.043(3) 0.002(2) 0.013(2) 0.001(2)
C1 0.034(3) 0.029(3) 0.045(3) 0.000(2) 0.010(3) -0.005(2)
C2 0.055(4) 0.031(3) 0.052(4) -0.002(3) 0.018(3) 0.002(3)
C3 0.048(4) 0.040(3) 0.050(3) 0.009(3) 0.009(3) 0.003(3)
C4 0.055(4) 0.044(4) 0.044(3) -0.001(3) 0.007(3) 0.006(3)
C5 0.046(4) 0.053(4) 0.032(3) -0.004(3) 0.009(3) 0.002(3)
C6 0.042(3) 0.036(3) 0.035(3) 0.000(3) 0.001(3) 0.001(2)
C7 0.049(4) 0.043(4) 0.047(3) -0.003(3) 0.010(3) -0.006(3)
C8 0.056(4) 0.034(3) 0.056(4) 0.000(3) 0.006(3) -0.007(3)
C9 0.057(4) 0.030(3) 0.055(4) -0.005(3) 0.004(3) 0.003(3)
C10 0.032(3) 0.039(3) 0.038(3) -0.004(3) -0.002(2) 0.000(3)
C11 0.023(3) 0.034(3) 0.038(3) -0.004(2) -0.001(2) 0.001(2)
C12 0.034(3) 0.033(3) 0.040(3) 0.001(3) 0.004(2) 0.001(2)
C13 0.031(3) 0.044(4) 0.045(3) 0.002(3) 0.003(3) -0.003(3)
C14 0.037(3) 0.042(4) 0.048(3) -0.002(3) 0.006(3) 0.005(3)
C15 0.037(4) 0.037(3) 0.042(3) 0.003(3) 0.013(3) -0.007(3)
C16 0.037(3) 0.047(4) 0.048(3) -0.004(3) 0.006(3) -0.007(3)
C17 0.047(4) 0.064(4) 0.046(3) 0.005(3) 0.013(3) 0.000(3)
C18 0.038(4) 0.080(5) 0.046(3) 0.001(4) 0.004(3) -0.026(4)
C19 0.042(4) 0.058(5) 0.082(5) -0.005(4) 0.004(4) -0.022(4)
C20 0.051(4) 0.038(4) 0.069(4) -0.006(3) 0.016(3) -0.010(3)
C21 0.053(4) 0.079(5) 0.054(4) -0.005(4) 0.024(3) -0.007(3)
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
C13 N C14 125.6(5) no
C13 N C21 116.6(5) no
C14 N C21 117.8(5) no
C2 C1 C15 133.9(5) yes
C2 C1 C12 93.1(4) yes
C15 C1 C12 132.9(5) yes
C1 C2 C3 95.9(5) yes
C1 C2 H2 133(4) no
C3 C2 H2 131(4) no
C4 C3 C2 110.1(5) yes
C4 C3 C12 115.2(5) no
C2 C3 C12 85.6(4) yes
C4 C3 H3A 114.2 no
C2 C3 H3A 114.2 no
C12 C3 H3A 114.2 no
C5 C4 C3 122.5(5) no
C5 C4 H4A 118.8 no
C3 C4 H4A 118.8 no
C4 C5 C6 123.8(5) no
C4 C5 Br 118.6(4) no
C6 C5 Br 117.5(4) no
C11 C6 C7 118.5(5) no
C11 C6 C5 118.3(5) no
C7 C6 C5 123.1(5) no
C8 C7 C6 121.0(5) no
C8 C7 H7A 119.5 no
C6 C7 H7A 119.5 no
C9 C8 C7 120.2(6) no
C9 C8 H8A 119.9 no
C7 C8 H8A 119.9 no
C8 C9 C10 119.9(6) no
C8 C9 H9A 120.1 no
C10 C9 H9A 120.1 no
C9 C10 C11 120.7(5) no
C9 C10 C14 118.8(5) no
C11 C10 C14 120.5(5) no
C6 C11 C10 119.4(5) no
C6 C11 C12 121.3(5) no
C10 C11 C12 119.3(5) no
C11 C12 C13 114.2(4) no
C11 C12 C1 118.2(4) yes
C13 C12 C1 107.3(4) yes
C11 C12 C3 115.7(4) no
C13 C12 C3 113.0(4) no
C1 C12 C3 85.0(4) yes
O2 C13 N 121.6(5) no
O2 C13 C12 121.6(5) no
N C13 C12 116.4(5) no
O1 C14 N 120.7(5) no
O1 C14 C10 122.1(5) no
N C14 C10 117.1(5) no
C16 C15 C20 118.0(5) no
C16 C15 C1 122.6(5) no
C20 C15 C1 119.5(5) no
C15 C16 C17 120.7(5) no
C15 C16 H16A 119.7 no
C17 C16 H16A 119.7 no
C18 C17 C16 120.3(6) no
C18 C17 H17A 119.8 no
C16 C17 H17A 119.8 no
C19 C18 C17 119.5(6) no
C19 C18 H18A 120.2 no
C17 C18 H18A 120.2 no
C20 C19 C18 121.0(6) no
C20 C19 H19A 119.5 no
C18 C19 H19A 119.5 no
C19 C20 C15 120.4(6) no
C19 C20 H20A 119.8 no
C15 C20 H20A 119.8 no
N C21 H21A 109.5 no
N C21 H21B 109.5 nno
H21A C21 H21B 109.5 no
N C21 H21C 109.5 no
H21A C21 H21C 109.5 no
H21B C21 H21C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br C5 1.905(5) no
O1 C14 1.215(6) no
O2 C13 1.205(6) no
N C13 1.381(7) no
N C14 1.383(7) no
N C21 1.489(7) no
C1 C2 1.333(7) yes
C1 C15 1.465(7) yes
C1 C12 1.552(7) yes
C2 C3 1.510(8) yes
C2 H2 0.88(6) no
C3 C4 1.476(8) yes
C3 C12 1.579(7) yes
C3 H3A 0.9800 no
C4 C5 1.325(8) yes
C4 H4A 0.9300 no?
C5 C6 1.470(7) no
C6 C11 1.391(7) no
C6 C7 1.407(7) no
C7 C8 1.379(8) no
C7 H7A 0.9300 no
C8 C9 1.366(8) no
C8 H8A 0.9300 no
C9 C10 1.390(7) no
C9 H9A 0.9300 no
C10 C11 1.395(7) no
C10 C14 1.487(8) no
C11 C12 1.493(7) yes
C12 C13 1.524(7) yes
C15 C16 1.380(7) no
C15 C20 1.402(7) no
C16 C17 1.383(7) no
C16 H16A 0.9300 no
C17 C18 1.368(8) no
C17 H17A 0.9300 no
C18 C19 1.367(9) no
C18 H18A 0.9300 no
C19 C20 1.364(8) no
C19 H19A 0.9300 no
C20 H20A 0.9300 no
C21 H21A 0.9600 no
C21 H21B 0.9600 no
C21 H21C 0.9600 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
C15 C1 C2 C3 178.9(6) ?
C12 C1 C2 C3 -4.9(5) ?
C1 C2 C3 C4 -110.4(5) ?
C1 C2 C3 C12 4.8(4) no
C2 C3 C4 C5 92.5(7) ?
C12 C3 C4 C5 -2.2(8) ?
C3 C4 C5 C6 11.2(9) no
C3 C4 C5 Br -172.5(4) no
C4 C5 C6 C11 -3.7(8) no
Br C5 C6 C11 180.0(4) no
C4 C5 C6 C7 172.4(6) no
Br C5 C6 C7 -3.9(7) no
C11 C6 C7 C8 3.8(8) no
C5 C6 C7 C8 -172.3(5) no
C6 C7 C8 C9 1.5(9) no
C7 C8 C9 C10 -2.7(9) no
C8 C9 C10 C11 -1.3(9) no
C8 C9 C10 C14 177.6(5) no
C7 C6 C11 C10 -7.7(8) no
C5 C6 C11 C10 168.6(5) no
C7 C6 C11 C12 170.6(5) no
C5 C6 C11 C12 -13.0(7) no
C9 C10 C11 C6 6.6(8) no
C14 C10 C11 C6 -172.3(5) no
C9 C10 C11 C12 -171.8(5) no
C14 C10 C11 C12 9.4(7) no
C6 C11 C12 C13 154.6(5) no
C10 C11 C12 C13 -27.1(6) no
C6 C11 C12 C1 -77.8(6) ?
C10 C11 C12 C1 100.5(6) no
C6 C11 C12 C3 20.7(7) no
C10 C11 C12 C3 -160.9(5) no
C2 C1 C12 C11 121.2(5) no
C15 C1 C12 C11 -62.5(7) ?
C2 C1 C12 C13 -107.9(5) ?
C15 C1 C12 C13 68.4(7) ?
C2 C1 C12 C3 4.7(4) no
C15 C1 C12 C3 -179.0(6) no
C4 C3 C12 C11 -12.9(7) no
C2 C3 C12 C11 -123.1(5) no
C4 C3 C12 C13 -147.3(5) no
C2 C3 C12 C13 102.5(5) no
C4 C3 C12 C1 106.1(5) no
C2 C3 C12 C1 -4.1(4) ?
C14 N C13 O2 172.4(5) no
C21 N C13 O2 -5.0(8) no
C14 N C13 C12 -14.1(8) no
C21 N C13 C12 168.6(4) no
C11 C12 C13 O2 -157.3(5) no
C1 C12 C13 O2 69.6(6) no
C3 C12 C13 O2 -22.3(7) no
C11 C12 C13 N 29.2(6) no
C1 C12 C13 N -103.9(5) no
C3 C12 C13 N 164.2(4) no
C13 N C14 O1 178.4(5) no
C21 N C14 O1 -4.3(8) no
C13 N C14 C10 -4.7(8) no
C21 N C14 C10 172.6(5) no
C9 C10 C14 O1 5.4(8) no
C11 C10 C14 O1 -175.7(5) no
C9 C10 C14 N -171.5(5) no
C11 C10 C14 N 7.4(7) no
C2 C1 C15 C16 -174.2(6) no
C12 C1 C15 C16 10.9(8) ?
C2 C1 C15 C20 6.1(9) ?
C12 C1 C15 C20 -168.8(5) no
C20 C15 C16 C17 0.2(8) no
C1 C15 C16 C17 -179.6(5) no
C15 C16 C17 C18 0.8(9) no
C16 C17 C18 C19 -1.8(9) no
C17 C18 C19 C20 1.9(10) no
C18 C19 C20 C15 -1.0(10) no
C16 C15 C20 C19 -0.1(8) no
C1 C15 C20 C19 179.7(5) no
_cod_database_code 2203332