data_2203332
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_common          ?
_chemical_name_systematic
;
9-Bromo-4-methyl-2-phenylbenzo[de]cyclobut[i]
isoquinoline-3,5(2H)-dione
;
_symmetry_cell_setting         Monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_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_detector_area_resol_mean ?
_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_meas    ?
_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_disorder_assembly
_atom_site_disorder_group
_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_site_symmetry_1
_geom_angle_site_symmetry_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_site_symmetry_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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_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