 
data_kcb-1
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H15 Br1 N2 O3'
_chemical_formula_weight          405.24
 
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'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    P21/c
 
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'
 
_cell_length_a                    13.5133(16)
_cell_length_b                    13.5483(8)
_cell_length_c                    9.6825(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.293(7)
_cell_angle_gamma                 90.00
_cell_volume                      1771.3(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        rectangular
_exptl_crystal_colour             ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.520
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              728
_exptl_absorpt_coefficient_mu     2.346
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             8479
_diffrn_reflns_av_R_equivalents   0.0612
_diffrn_reflns_av_sigmaI/netI     0.1510
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        8
_diffrn_reflns_theta_min          2.95
_diffrn_reflns_theta_max          28.95
_reflns_number_total              4053
_reflns_number_gt                 1533
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0442P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          4053
_refine_ls_number_parameters      238
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2039
_refine_ls_R_factor_gt            0.0639
_refine_ls_wR_factor_ref          0.1475
_refine_ls_wR_factor_gt           0.1060
_refine_ls_goodness_of_fit_ref    0.943
_refine_ls_restrained_S_all       0.943
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C C 0.5977(4) 0.3665(4) 0.1395(5) 0.0458(15) Uani 1 1 d . . .
C22 C 1.0077(5) 0.0947(6) 0.1551(6) 0.074(2) Uani 1 1 d . . .
H22 H 1.0491 0.1006 0.0810 0.089 Uiso 1 1 calc R . .
C21 C 1.0016(5) 0.0060(5) 0.2216(6) 0.076(2) Uani 1 1 d . . .
H21 H 1.0387 -0.0477 0.1936 0.091 Uiso 1 1 calc R . .
O11 O 0.4636(5) 0.3620(4) 0.5043(5) 0.0782(17) Uani 1 1 d . . .
H2 H 0.817(4) 0.236(4) 0.427(5) 0.053(18) Uiso 1 1 d . . .
H13 H 0.488(5) 0.314(5) 0.538(6) 0.08(3) Uiso 1 1 d . . .
H12 H 0.448(5) 0.395(5) 0.559(6) 0.07(3) Uiso 1 1 d . . .
Br Br 0.81831(6) 0.78986(5) 0.12632(6) 0.0907(4) Uani 1 1 d . . .
O002 O 0.5661(3) 0.4737(2) 0.3288(3) 0.0486(10) Uani 1 1 d . . .
H002 H 0.5457 0.4296 0.3781 0.073 Uiso 1 1 calc R . .
O003 O 0.5605(3) 0.2866(3) 0.1628(3) 0.0571(11) Uani 1 1 d . . .
C004 C 0.7316(4) 0.6044(4) 0.1938(5) 0.0483(15) Uani 1 1 d . . .
H004 H 0.7552 0.6159 0.2839 0.058 Uiso 1 1 calc R . .
N005 N 0.5983(3) 0.4119(3) 0.0143(3) 0.0443(12) Uani 1 1 d . . .
C006 C 0.6473(4) 0.5031(4) 0.0249(4) 0.0435(14) Uani 1 1 d . . .
O007 O 0.7924(3) 0.3169(2) 0.1445(3) 0.0509(11) Uani 1 1 d . . .
N008 N 0.8324(3) 0.2446(3) 0.3500(4) 0.0430(13) Uani 1 1 d . . .
C009 C 0.7856(4) 0.3136(3) 0.2711(5) 0.0364(13) Uani 1 1 d . . .
C012 C 0.6446(4) 0.4370(3) 0.2498(4) 0.0382(13) Uani 1 1 d . . .
C013 C 0.6618(5) 0.5708(4) -0.0776(5) 0.0598(18) Uani 1 1 d . . .
H013 H 0.6386 0.5592 -0.1679 0.072 Uiso 1 1 calc R . .
C014 C 0.8911(4) 0.1658(4) 0.3039(4) 0.0398(13) Uani 1 1 d . . .
C016 C 0.7475(5) 0.6722(4) 0.0882(5) 0.0564(16) Uani 1 1 d . . .
C017 C 0.7240(4) 0.3864(3) 0.3412(4) 0.0381(13) Uani 1 1 d . . .
C018 C 0.5661(4) 0.3651(4) -0.1144(4) 0.0580(17) Uani 1 1 d . . .
H01A H 0.5733 0.4106 -0.1894 0.087 Uiso 1 1 calc R . .
H01B H 0.4978 0.3461 -0.1098 0.087 Uiso 1 1 calc R . .
H01C H 0.6058 0.3076 -0.1292 0.087 Uiso 1 1 calc R . .
C020 C 0.6800(4) 0.5204(4) 0.1596(4) 0.0392(13) Uani 1 1 d . . .
C021 C 0.9541(4) 0.1755(4) 0.1950(5) 0.0530(15) Uani 1 1 d . . .
H021 H 0.9599 0.2356 0.1498 0.064 Uiso 1 1 calc R . .
C024 C 0.8852(4) 0.0758(4) 0.3707(5) 0.0521(15) Uani 1 1 d . . .
H024 H 0.8436 0.0685 0.4441 0.063 Uiso 1 1 calc R . .
C026 C 0.9408(5) -0.0024(4) 0.3288(6) 0.0722(19) Uani 1 1 d . . .
H026 H 0.9366 -0.0625 0.3748 0.087 Uiso 1 1 calc R . .
C027 C 0.7109(5) 0.6550(4) -0.0434(5) 0.0659(19) Uani 1 1 d . . .
H027 H 0.7200 0.7024 -0.1112 0.079 Uiso 1 1 calc R . .
C028 C 0.7388(4) 0.4127(4) 0.4711(5) 0.0613(18) Uani 1 1 d . . .
H02A H 0.7905 0.3850 0.5241 0.074 Uiso 1 1 calc R . .
H02B H 0.6974 0.4591 0.5099 0.074 Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C O003 1.218(6) . ?
C N005 1.360(5) . ?
C C012 1.550(7) . ?
C22 C21 1.368(8) . ?
C22 C021 1.376(8) . ?
C22 H22 0.9300 . ?
C21 C026 1.354(7) . ?
C21 H21 0.9300 . ?
O11 H13 0.80(6) . ?
O11 H12 0.73(5) . ?
Br C016 1.888(6) . ?
O002 C012 1.423(5) . ?
O002 H002 0.8200 . ?
C004 C020 1.369(6) . ?
C004 C016 1.397(6) . ?
C004 H004 0.9300 . ?
N005 C006 1.404(6) . ?
N005 C018 1.449(5) . ?
C006 C013 1.371(6) . ?
C006 C020 1.380(6) . ?
O007 C009 1.234(5) . ?
N008 C009 1.348(6) . ?
N008 C014 1.412(6) . ?
N008 H2 0.79(4) . ?
C009 C017 1.474(7) . ?
C012 C020 1.517(6) . ?
C012 C017 1.527(6) . ?
C013 C027 1.354(7) . ?
C013 H013 0.9300 . ?
C014 C024 1.383(6) . ?
C014 C021 1.388(6) . ?
C016 C027 1.369(7) . ?
C017 C028 1.314(5) . ?
C018 H01A 0.9600 . ?
C018 H01B 0.9600 . ?
C018 H01C 0.9600 . ?
C021 H021 0.9300 . ?
C024 C026 1.370(7) . ?
C024 H024 0.9300 . ?
C026 H026 0.9300 . ?
C027 H027 0.9300 . ?
C028 H02A 0.9300 . ?
C028 H02B 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O003 C N005 125.8(5) . . ?
O003 C C012 125.5(4) . . ?
N005 C C012 108.5(4) . . ?
C21 C22 C021 121.6(5) . . ?
C21 C22 H22 119.2 . . ?
C021 C22 H22 119.2 . . ?
C026 C21 C22 119.0(6) . . ?
C026 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
H13 O11 H12 109(7) . . ?
C012 O002 H002 109.5 . . ?
C020 C004 C016 117.5(4) . . ?
C020 C004 H004 121.3 . . ?
C016 C004 H004 121.3 . . ?
C N005 C006 110.7(4) . . ?
C N005 C018 123.8(4) . . ?
C006 N005 C018 124.9(4) . . ?
C013 C006 C020 121.4(5) . . ?
C013 C006 N005 128.0(4) . . ?
C020 C006 N005 110.5(4) . . ?
C009 N008 C014 127.0(4) . . ?
C009 N008 H2 120(4) . . ?
C014 N008 H2 111(4) . . ?
O007 C009 N008 122.4(4) . . ?
O007 C009 C017 120.0(5) . . ?
N008 C009 C017 117.6(4) . . ?
O002 C012 C020 108.0(4) . . ?
O002 C012 C017 111.6(3) . . ?
C020 C012 C017 116.0(4) . . ?
O002 C012 C 107.0(4) . . ?
C020 C012 C 101.1(4) . . ?
C017 C012 C 112.4(4) . . ?
C027 C013 C006 118.0(5) . . ?
C027 C013 H013 121.0 . . ?
C006 C013 H013 121.0 . . ?
C024 C014 C021 119.1(5) . . ?
C024 C014 N008 118.4(5) . . ?
C021 C014 N008 122.5(5) . . ?
C027 C016 C004 120.6(5) . . ?
C027 C016 Br 119.2(4) . . ?
C004 C016 Br 120.2(4) . . ?
C028 C017 C009 123.8(5) . . ?
C028 C017 C012 120.6(5) . . ?
C009 C017 C012 115.5(4) . . ?
N005 C018 H01A 109.5 . . ?
N005 C018 H01B 109.5 . . ?
H01A C018 H01B 109.5 . . ?
N005 C018 H01C 109.5 . . ?
H01A C018 H01C 109.5 . . ?
H01B C018 H01C 109.5 . . ?
C004 C020 C006 120.7(4) . . ?
C004 C020 C012 130.5(4) . . ?
C006 C020 C012 108.8(4) . . ?
C22 C021 C014 119.0(5) . . ?
C22 C021 H021 120.5 . . ?
C014 C021 H021 120.5 . . ?
C026 C024 C014 120.1(5) . . ?
C026 C024 H024 119.9 . . ?
C014 C024 H024 119.9 . . ?
C21 C026 C024 121.2(6) . . ?
C21 C026 H026 119.4 . . ?
C024 C026 H026 119.4 . . ?
C013 C027 C016 121.8(5) . . ?
C013 C027 H027 119.1 . . ?
C016 C027 H027 119.1 . . ?
C017 C028 H02A 120.0 . . ?
C017 C028 H02B 120.0 . . ?
H02A C028 H02B 120.0 . . ?
 
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_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C021 C22 C21 C026 0.4(10) . . . . ?
O003 C N005 C006 179.7(5) . . . . ?
C012 C N005 C006 4.5(6) . . . . ?
O003 C N005 C018 -8.9(8) . . . . ?
C012 C N005 C018 175.8(4) . . . . ?
C N005 C006 C013 -179.0(5) . . . . ?
C018 N005 C006 C013 9.8(9) . . . . ?
C N005 C006 C020 -0.4(6) . . . . ?
C018 N005 C006 C020 -171.6(4) . . . . ?
C014 N008 C009 O007 -2.6(8) . . . . ?
C014 N008 C009 C017 176.9(5) . . . . ?
O003 C C012 O002 -68.7(6) . . . . ?
N005 C C012 O002 106.6(4) . . . . ?
O003 C C012 C020 178.4(5) . . . . ?
N005 C C012 C020 -6.3(5) . . . . ?
O003 C C012 C017 54.1(7) . . . . ?
N005 C C012 C017 -130.6(4) . . . . ?
C020 C006 C013 C027 1.0(8) . . . . ?
N005 C006 C013 C027 179.5(6) . . . . ?
C009 N008 C014 C024 -142.2(5) . . . . ?
C009 N008 C014 C021 37.9(8) . . . . ?
C020 C004 C016 C027 1.0(8) . . . . ?
C020 C004 C016 Br -179.8(4) . . . . ?
O007 C009 C017 C028 -154.2(5) . . . . ?
N008 C009 C017 C028 26.2(8) . . . . ?
O007 C009 C017 C012 21.2(7) . . . . ?
N008 C009 C017 C012 -158.3(4) . . . . ?
O002 C012 C017 C028 -27.8(6) . . . . ?
C020 C012 C017 C028 96.4(6) . . . . ?
C C012 C017 C028 -148.0(5) . . . . ?
O002 C012 C017 C009 156.7(4) . . . . ?
C020 C012 C017 C009 -79.2(5) . . . . ?
C C012 C017 C009 36.4(6) . . . . ?
C016 C004 C020 C006 1.5(8) . . . . ?
C016 C004 C020 C012 -175.2(5) . . . . ?
C013 C006 C020 C004 -2.6(8) . . . . ?
N005 C006 C020 C004 178.7(5) . . . . ?
C013 C006 C020 C012 174.8(5) . . . . ?
N005 C006 C020 C012 -3.9(6) . . . . ?
O002 C012 C020 C004 70.9(7) . . . . ?
C017 C012 C020 C004 -55.1(7) . . . . ?
C C012 C020 C004 -176.9(6) . . . . ?
O002 C012 C020 C006 -106.1(4) . . . . ?
C017 C012 C020 C006 127.8(4) . . . . ?
C C012 C020 C006 6.0(5) . . . . ?
C21 C22 C021 C014 -1.2(9) . . . . ?
C024 C014 C021 C22 1.1(8) . . . . ?
N008 C014 C021 C22 -179.1(5) . . . . ?
C021 C014 C024 C026 -0.3(8) . . . . ?
N008 C014 C024 C026 179.8(5) . . . . ?
C22 C21 C026 C024 0.4(10) . . . . ?
C014 C024 C026 C21 -0.4(10) . . . . ?
C006 C013 C027 C016 1.5(9) . . . . ?
C004 C016 C027 C013 -2.6(9) . . . . ?
Br C016 C027 C013 178.3(5) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.864
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.320
_refine_diff_density_min   -0.516
_refine_diff_density_rms    0.068
