# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_101102

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 Br N2 O2'
_chemical_formula_sum            'C24 H19 Br N2 O2'
_chemical_formula_weight         447.32

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.424(16)
_cell_length_b                   9.834(11)
_cell_length_c                   16.368(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.546(7)
_cell_angle_gamma                90.00
_cell_volume                     1981(4)
_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       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    2.099
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_T_max  0.8176
_exptl_absorpt_process_details   
;
Jacobson, RA (1998). REQAB. Version 1.1. Molecular Structure Corporation,
 9009 Research Forest Drive, The Woodlands, TX 77381, USA.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16408
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3661
_reflns_number_gt                2031
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Crystal Clear ver 1.3.6 SP3 (Rigaku, 2007)'
_computing_cell_refinement       'Crystal Clear ver 1.3.6 SP3 (Rigaku, 2007)'
_computing_data_reduction        'Crystal Clear ver 1.3.6 SP3 (Rigaku, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'yadokari-XG (Wakita, 2005)'

_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)+(0.1643P)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         3661
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1578
_refine_ls_R_factor_gt           0.0902
_refine_ls_wR_factor_ref         0.3358
_refine_ls_wR_factor_gt          0.2539
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1 C -0.2390(6) 0.8787(7) 0.1162(5) 0.0537(17) Uani 1 1 d . . .
H1 H -0.310(5) 0.830(7) 0.110(4) 0.052(17) Uiso 1 1 d . . .
N1 N -0.2245(5) 0.9750(7) 0.1856(4) 0.0648(17) Uani 1 1 d . . .
H2 H -0.2812 1.0033 0.1926 0.078 Uiso 1 1 calc R . .
C2 C -0.1160(7) 1.1439(9) 0.2853(5) 0.071(2) Uani 1 1 d . . .
H3 H -0.1771 1.1960 0.2769 0.085 Uiso 1 1 calc R . .
C3 C -0.0167(8) 1.1881(10) 0.3419(5) 0.079(2) Uani 1 1 d . . .
H4 H -0.0100 1.2710 0.3710 0.095 Uiso 1 1 calc R . .
C4 C 0.0742(7) 1.1110(10) 0.3566(6) 0.084(3) Uani 1 1 d . . .
H5 H 0.1424 1.1407 0.3958 0.100 Uiso 1 1 calc R . .
C5 C 0.0631(7) 0.9923(9) 0.3134(5) 0.074(2) Uani 1 1 d . . .
H6 H 0.1243 0.9389 0.3241 0.089 Uiso 1 1 calc R . .
C6 C -0.0499(5) 0.8205(8) 0.2098(5) 0.0584(18) Uani 1 1 d . . .
H7 H 0.0091 0.7617 0.2253 0.070 Uiso 1 1 calc R . .
C7 C -0.1441(6) 0.7837(7) 0.1475(5) 0.0549(17) Uani 1 1 d . . .
C8 C -0.1275(6) 1.0234(8) 0.2403(5) 0.0588(18) Uani 1 1 d . . .
C9 C -0.0367(6) 0.9475(7) 0.2534(5) 0.0562(18) Uani 1 1 d . . .
C10 C -0.1658(6) 0.6517(8) 0.1039(5) 0.065(2) Uani 1 1 d . . .
O1 O -0.2577(4) 0.6171(6) 0.0578(4) 0.0785(16) Uani 1 1 d . . .
C11 C -0.0754(6) 0.5575(7) 0.1180(5) 0.0571(18) Uani 1 1 d . . .
C12 C 0.0165(7) 0.5937(9) 0.1064(5) 0.071(2) Uani 1 1 d . . .
H8 H 0.0260 0.6836 0.0934 0.085 Uiso 1 1 calc R . .
C13 C 0.0929(7) 0.5014(9) 0.1134(6) 0.075(2) Uani 1 1 d . . .
H9 H 0.1545 0.5268 0.1044 0.090 Uiso 1 1 calc R . .
C14 C 0.0799(6) 0.3718(8) 0.1335(5) 0.064(2) Uani 1 1 d . . .
C15 C -0.0089(7) 0.3327(9) 0.1462(6) 0.073(2) Uani 1 1 d . . .
H10 H -0.0166 0.2432 0.1610 0.088 Uiso 1 1 calc R . .
C16 C -0.0872(6) 0.4262(8) 0.1371(5) 0.070(2) Uani 1 1 d . . .
H11 H -0.1498 0.3995 0.1441 0.084 Uiso 1 1 calc R . .
Br1 Br 0.18417(9) 0.24175(11) 0.14169(8) 0.1001(6) Uani 1 1 d . . .
C17 C -0.2551(6) 0.9443(7) 0.0301(4) 0.0543(17) Uani 1 1 d . . .
C18 C -0.3423(5) 0.9203(7) -0.0475(5) 0.0543(17) Uani 1 1 d . . .
C19 C -0.3560(6) 0.9867(8) -0.1241(5) 0.065(2) Uani 1 1 d . . .
H12 H -0.4159 0.9681 -0.1765 0.078 Uiso 1 1 calc R . .
C20 C -0.2816(8) 1.0799(9) -0.1233(6) 0.084(3) Uani 1 1 d . . .
H13 H -0.2925 1.1289 -0.1747 0.101 Uiso 1 1 calc R . .
C21 C -0.1912(8) 1.1026(9) -0.0481(6) 0.086(3) Uani 1 1 d . . .
H14 H -0.1381 1.1629 -0.0487 0.103 Uiso 1 1 calc R . .
C22 C -0.1794(7) 1.0362(9) 0.0275(5) 0.072(2) Uani 1 1 d . . .
H15 H -0.1183 1.0533 0.0794 0.087 Uiso 1 1 calc R . .
N2 N -0.4162(4) 0.8207(7) -0.0490(4) 0.0620(16) Uani 1 1 d . . .
H16 H -0.3897 0.7470 -0.0204 0.074 Uiso 1 1 calc R . .
C23 C -0.5228(7) 0.8275(11) -0.0899(6) 0.076(2) Uani 1 1 d . . .
O2 O -0.5661(4) 0.9283(8) -0.1308(5) 0.101(2) Uani 1 1 d . . .
C24 C -0.5846(7) 0.7146(12) -0.0776(7) 0.095(3) Uani 1 1 d . . .
H17 H -0.6239 0.7438 -0.0430 0.143 Uiso 1 1 calc R . .
H18 H -0.5360 0.6422 -0.0470 0.143 Uiso 1 1 calc R . .
H19 H -0.6348 0.6828 -0.1347 0.143 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
C1 N1 1.432(9) . ?
C1 C17 1.485(10) . ?
C1 C7 1.496(10) . ?
C1 H1 1.04(7) . ?
N1 C8 1.338(9) . ?
N1 H2 0.8600 . ?
C2 C3 1.356(12) . ?
C2 C8 1.372(11) . ?
C2 H3 0.9300 . ?
C3 C4 1.374(12) . ?
C3 H4 0.9300 . ?
C4 C5 1.342(12) . ?
C4 H5 0.9300 . ?
C5 C9 1.379(10) . ?
C5 H6 0.9300 . ?
C6 C7 1.319(9) . ?
C6 C9 1.413(10) . ?
C6 H7 0.9300 . ?
C7 C10 1.454(11) . ?
C8 C9 1.372(10) . ?
C10 O1 1.210(9) . ?
C10 C11 1.470(10) . ?
C11 C16 1.352(11) . ?
C11 C12 1.369(10) . ?
C12 C13 1.340(12) . ?
C12 H8 0.9300 . ?
C13 C14 1.346(12) . ?
C13 H9 0.9300 . ?
C14 C15 1.346(11) . ?
C14 Br1 1.861(8) . ?
C15 C16 1.358(11) . ?
C15 H10 0.9300 . ?
C16 H11 0.9300 . ?
C17 C18 1.360(9) . ?
C17 C22 1.373(10) . ?
C18 C19 1.359(10) . ?
C18 N2 1.387(9) . ?
C19 C20 1.351(12) . ?
C19 H12 0.9300 . ?
C20 C21 1.357(12) . ?
C20 H13 0.9300 . ?
C21 C22 1.353(11) . ?
C21 H14 0.9300 . ?
C22 H15 0.9300 . ?
N2 C23 1.317(10) . ?
N2 H16 0.8600 . ?
C23 O2 1.207(11) . ?
C23 C24 1.448(14) . ?
C24 H17 0.9600 . ?
C24 H18 0.9600 . ?
C24 H19 0.9600 . ?

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
N1 C1 C17 112.8(6) . . ?
N1 C1 C7 108.3(6) . . ?
C17 C1 C7 112.2(6) . . ?
N1 C1 H1 102(4) . . ?
C17 C1 H1 110(3) . . ?
C7 C1 H1 111(4) . . ?
C8 N1 C1 123.6(6) . . ?
C8 N1 H2 118.2 . . ?
C1 N1 H2 118.2 . . ?
C3 C2 C8 120.9(8) . . ?
C3 C2 H3 119.5 . . ?
C8 C2 H3 119.5 . . ?
C2 C3 C4 120.3(9) . . ?
C2 C3 H4 119.8 . . ?
C4 C3 H4 119.8 . . ?
C5 C4 C3 119.0(8) . . ?
C5 C4 H5 120.5 . . ?
C3 C4 H5 120.5 . . ?
C4 C5 C9 121.7(8) . . ?
C4 C5 H6 119.2 . . ?
C9 C5 H6 119.2 . . ?
C7 C6 C9 121.4(7) . . ?
C7 C6 H7 119.3 . . ?
C9 C6 H7 119.3 . . ?
C6 C7 C10 124.5(7) . . ?
C6 C7 C1 121.0(7) . . ?
C10 C7 C1 114.4(6) . . ?
N1 C8 C2 122.5(7) . . ?
N1 C8 C9 118.5(7) . . ?
C2 C8 C9 118.9(7) . . ?
C8 C9 C5 119.2(7) . . ?
C8 C9 C6 118.5(7) . . ?
C5 C9 C6 122.2(7) . . ?
O1 C10 C7 120.8(7) . . ?
O1 C10 C11 119.5(7) . . ?
C7 C10 C11 119.7(7) . . ?
C16 C11 C12 118.4(7) . . ?
C16 C11 C10 118.2(7) . . ?
C12 C11 C10 123.2(7) . . ?
C13 C12 C11 121.0(8) . . ?
C13 C12 H8 119.5 . . ?
C11 C12 H8 119.5 . . ?
C12 C13 C14 119.5(8) . . ?
C12 C13 H9 120.3 . . ?
C14 C13 H9 120.3 . . ?
C15 C14 C13 121.2(8) . . ?
C15 C14 Br1 118.7(7) . . ?
C13 C14 Br1 120.0(7) . . ?
C14 C15 C16 119.0(8) . . ?
C14 C15 H10 120.5 . . ?
C16 C15 H10 120.5 . . ?
C11 C16 C15 121.0(8) . . ?
C11 C16 H11 119.5 . . ?
C15 C16 H11 119.5 . . ?
C18 C17 C22 117.2(7) . . ?
C18 C17 C1 123.7(7) . . ?
C22 C17 C1 119.0(6) . . ?
C19 C18 C17 121.8(7) . . ?
C19 C18 N2 119.4(6) . . ?
C17 C18 N2 118.8(7) . . ?
C20 C19 C18 119.3(8) . . ?
C20 C19 H12 120.3 . . ?
C18 C19 H12 120.3 . . ?
C19 C20 C21 120.7(8) . . ?
C19 C20 H13 119.7 . . ?
C21 C20 H13 119.7 . . ?
C22 C21 C20 119.0(9) . . ?
C22 C21 H14 120.5 . . ?
C20 C21 H14 120.5 . . ?
C21 C22 C17 121.9(8) . . ?
C21 C22 H15 119.1 . . ?
C17 C22 H15 119.1 . . ?
C23 N2 C18 126.7(7) . . ?
C23 N2 H16 116.7 . . ?
C18 N2 H16 116.7 . . ?
O2 C23 N2 120.5(9) . . ?
O2 C23 C24 122.1(9) . . ?
N2 C23 C24 117.2(9) . . ?
C23 C24 H17 109.5 . . ?
C23 C24 H18 109.5 . . ?
H17 C24 H18 109.5 . . ?
C23 C24 H19 109.5 . . ?
H17 C24 H19 109.5 . . ?
H18 C24 H19 109.5 . . ?

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
C17 C1 N1 C8 -90.0(8) . . . . ?
C7 C1 N1 C8 34.9(9) . . . . ?
C8 C2 C3 C4 -1.4(14) . . . . ?
C2 C3 C4 C5 0.6(14) . . . . ?
C3 C4 C5 C9 1.5(14) . . . . ?
C9 C6 C7 C10 -175.8(7) . . . . ?
C9 C6 C7 C1 4.1(11) . . . . ?
N1 C1 C7 C6 -24.3(10) . . . . ?
C17 C1 C7 C6 100.9(8) . . . . ?
N1 C1 C7 C10 155.6(6) . . . . ?
C17 C1 C7 C10 -79.1(8) . . . . ?
C1 N1 C8 C2 158.0(7) . . . . ?
C1 N1 C8 C9 -23.8(11) . . . . ?
C3 C2 C8 N1 178.3(8) . . . . ?
C3 C2 C8 C9 0.1(12) . . . . ?
N1 C8 C9 C5 -176.4(7) . . . . ?
C2 C8 C9 C5 1.9(11) . . . . ?
N1 C8 C9 C6 -1.1(10) . . . . ?
C2 C8 C9 C6 177.2(7) . . . . ?
C4 C5 C9 C8 -2.7(13) . . . . ?
C4 C5 C9 C6 -177.8(8) . . . . ?
C7 C6 C9 C8 10.3(11) . . . . ?
C7 C6 C9 C5 -174.6(8) . . . . ?
C6 C7 C10 O1 168.4(8) . . . . ?
C1 C7 C10 O1 -11.5(10) . . . . ?
C6 C7 C10 C11 -9.8(12) . . . . ?
C1 C7 C10 C11 170.2(7) . . . . ?
O1 C10 C11 C16 -45.1(11) . . . . ?
C7 C10 C11 C16 133.2(8) . . . . ?
O1 C10 C11 C12 129.9(9) . . . . ?
C7 C10 C11 C12 -51.8(11) . . . . ?
C16 C11 C12 C13 0.2(12) . . . . ?
C10 C11 C12 C13 -174.8(8) . . . . ?
C11 C12 C13 C14 -1.0(13) . . . . ?
C12 C13 C14 C15 0.4(13) . . . . ?
C12 C13 C14 Br1 179.0(7) . . . . ?
C13 C14 C15 C16 1.0(13) . . . . ?
Br1 C14 C15 C16 -177.6(6) . . . . ?
C12 C11 C16 C15 1.3(12) . . . . ?
C10 C11 C16 C15 176.5(8) . . . . ?
C14 C15 C16 C11 -1.8(13) . . . . ?
N1 C1 C17 C18 -124.5(7) . . . . ?
C7 C1 C17 C18 112.8(8) . . . . ?
N1 C1 C17 C22 54.6(9) . . . . ?
C7 C1 C17 C22 -68.1(9) . . . . ?
C22 C17 C18 C19 -1.6(11) . . . . ?
C1 C17 C18 C19 177.4(7) . . . . ?
C22 C17 C18 N2 175.2(7) . . . . ?
C1 C17 C18 N2 -5.8(11) . . . . ?
C17 C18 C19 C20 -0.6(11) . . . . ?
N2 C18 C19 C20 -177.4(7) . . . . ?
C18 C19 C20 C21 3.3(13) . . . . ?
C19 C20 C21 C22 -3.8(14) . . . . ?
C20 C21 C22 C17 1.4(15) . . . . ?
C18 C17 C22 C21 1.2(13) . . . . ?
C1 C17 C22 C21 -177.9(8) . . . . ?
C19 C18 N2 C23 -43.8(11) . . . . ?
C17 C18 N2 C23 139.3(8) . . . . ?
C18 N2 C23 O2 -0.8(13) . . . . ?
C18 N2 C23 C24 -176.0(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.077

_database_code_depnum_ccdc_archive 'CCDC 1003324'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_110719

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            dibenzonaphthyridine
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 N2'
_chemical_formula_sum            'C23 H16 N2'
_chemical_formula_weight         320.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.980(18)
_cell_length_b                   5.904(3)
_cell_length_c                   15.103(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.257(9)
_cell_angle_gamma                90.00
_cell_volume                     3297(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3208
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      26.0

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_process_details   
;
Jacobson, RA (1998). REQAB. Version 1.1. Molecular Structure Corporation,
 9009 Research Forest Drive, The Woodlands, TX 77381, USA.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  Rigaku_Saturn724+
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10985
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.31
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3208
_reflns_number_gt                1561
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Crystal Clear ver 1.3.6 SP3 (Rigaku, 2007)'
_computing_cell_refinement       'Crystal Clear ver 1.3.6 SP3 (Rigaku, 2007)'
_computing_data_reduction        'Crystal Clear ver 1.3.6 SP3 (Rigaku, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'yadokari-XG (Wakita, 2005)'

_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)+(0.0687P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3208
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1603
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
N1 N 0.93666(7) 0.3395(4) -0.00415(15) 0.0537(7) Uani 1 1 d . . .
C1 C 0.92205(9) 0.5179(5) -0.04988(17) 0.0490(8) Uani 1 1 d . . .
C2 C 0.88463(9) 0.5664(5) -0.04973(18) 0.0492(8) Uani 1 1 d . . .
C3 C 0.86214(9) 0.4314(5) 0.00149(17) 0.0513(8) Uani 1 1 d . . .
H1 H 0.8375 0.4613 0.0035 0.062 Uiso 1 1 calc R . .
C4 C 0.85413(9) 0.1007(5) 0.10281(17) 0.0452(8) Uani 1 1 d . . .
N2 N 0.86715(7) -0.0804(4) 0.14197(14) 0.0473(7) Uani 1 1 d . . .
C5 C 0.90439(9) -0.1222(5) 0.13705(17) 0.0448(8) Uani 1 1 d . . .
C6 C 0.92838(8) 0.0181(5) 0.09189(16) 0.0435(7) Uani 1 1 d . . .
C7 C 0.91390(8) 0.2123(5) 0.04357(18) 0.0448(8) Uani 1 1 d . . .
C8 C 0.87640(8) 0.2526(5) 0.04955(17) 0.0422(7) Uani 1 1 d . . .
C9 C 0.94575(10) 0.6579(6) -0.0994(2) 0.0639(10) Uani 1 1 d . . .
H2 H 0.9705 0.6291 -0.0992 0.077 Uiso 1 1 calc R . .
C10 C 0.93223(12) 0.8341(6) -0.1473(2) 0.0723(11) Uani 1 1 d . . .
H3 H 0.9478 0.9236 -0.1804 0.087 Uiso 1 1 calc R . .
C11 C 0.89507(12) 0.8829(6) -0.1474(2) 0.0724(11) Uani 1 1 d . . .
H4 H 0.8864 1.0052 -0.1799 0.087 Uiso 1 1 calc R . .
C12 C 0.87169(10) 0.7530(5) -0.1003(2) 0.0629(10) Uani 1 1 d . . .
H5 H 0.8471 0.7863 -0.1011 0.075 Uiso 1 1 calc R . .
C13 C 0.91764(10) -0.3126(5) 0.18240(18) 0.0563(9) Uani 1 1 d . . .
H6 H 0.9018 -0.4073 0.2125 0.068 Uiso 1 1 calc R . .
C14 C 0.95399(10) -0.3585(6) 0.1822(2) 0.0617(9) Uani 1 1 d . . .
H7 H 0.9627 -0.4857 0.2117 0.074 Uiso 1 1 calc R . .
C15 C 0.97781(10) -0.2166(6) 0.1384(2) 0.0650(10) Uani 1 1 d . . .
H8 H 1.0024 -0.2489 0.1391 0.078 Uiso 1 1 calc R . .
C16 C 0.96547(9) -0.0293(6) 0.09409(19) 0.0563(9) Uani 1 1 d . . .
H9 H 0.9817 0.0661 0.0656 0.068 Uiso 1 1 calc R . .
C17 C 0.81522(9) 0.1488(5) 0.11487(17) 0.0463(8) Uani 1 1 d . . .
C18 C 0.80363(9) 0.3541(5) 0.14949(19) 0.0563(9) Uani 1 1 d . . .
H10 H 0.8206 0.4646 0.1640 0.068 Uiso 1 1 calc R . .
C19 C 0.76747(10) 0.3963(6) 0.16257(19) 0.0608(10) Uani 1 1 d . . .
H11 H 0.7605 0.5343 0.1868 0.073 Uiso 1 1 calc R . .
C20 C 0.74122(9) 0.2388(6) 0.14066(19) 0.0552(9) Uani 1 1 d . . .
C21 C 0.75263(9) 0.0368(6) 0.1053(2) 0.0615(9) Uani 1 1 d . . .
H12 H 0.7355 -0.0714 0.0894 0.074 Uiso 1 1 calc R . .
C22 C 0.78896(9) -0.0097(5) 0.09285(18) 0.0559(9) Uani 1 1 d . . .
H13 H 0.7958 -0.1487 0.0694 0.067 Uiso 1 1 calc R . .
C23 C 0.70177(9) 0.2906(6) 0.1554(2) 0.0763(11) Uani 1 1 d . . .
H14 H 0.6919 0.3625 0.1037 0.115 Uiso 1 1 calc R . .
H15 H 0.6994 0.3900 0.2054 0.115 Uiso 1 1 calc R . .
H16 H 0.6889 0.1523 0.1666 0.115 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
N1 C7 1.340(3) . ?
N1 C1 1.370(4) . ?
C1 C2 1.413(4) . ?
C1 C9 1.420(4) . ?
C2 C3 1.390(4) . ?
C2 C12 1.422(4) . ?
C3 C8 1.384(4) . ?
C4 N2 1.312(3) . ?
C4 C8 1.462(4) . ?
C4 C17 1.479(4) . ?
N2 C5 1.401(4) . ?
C5 C6 1.394(4) . ?
C5 C13 1.404(4) . ?
C6 C16 1.400(4) . ?
C6 C7 1.460(4) . ?
C7 C8 1.410(4) . ?
C9 C10 1.360(4) . ?
C10 C11 1.404(5) . ?
C11 C12 1.359(4) . ?
C13 C14 1.371(4) . ?
C14 C15 1.386(4) . ?
C15 C16 1.370(4) . ?
C17 C22 1.388(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.375(4) . ?
C19 C20 1.383(4) . ?
C20 C21 1.374(4) . ?
C20 C23 1.508(4) . ?
C21 C22 1.385(4) . ?

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
C7 N1 C1 117.0(3) . . ?
N1 C1 C2 122.6(3) . . ?
N1 C1 C9 118.1(3) . . ?
C2 C1 C9 119.3(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C12 122.9(3) . . ?
C1 C2 C12 118.9(3) . . ?
C8 C3 C2 120.1(3) . . ?
N2 C4 C8 122.8(3) . . ?
N2 C4 C17 117.2(3) . . ?
C8 C4 C17 120.0(3) . . ?
C4 N2 C5 118.6(3) . . ?
C6 C5 N2 123.3(3) . . ?
C6 C5 C13 119.5(3) . . ?
N2 C5 C13 117.1(3) . . ?
C5 C6 C16 119.7(3) . . ?
C5 C6 C7 118.6(3) . . ?
C16 C6 C7 121.7(3) . . ?
N1 C7 C8 124.1(3) . . ?
N1 C7 C6 118.6(3) . . ?
C8 C7 C6 117.3(3) . . ?
C3 C8 C7 117.9(3) . . ?
C3 C8 C4 122.9(3) . . ?
C7 C8 C4 119.2(3) . . ?
C10 C9 C1 119.9(4) . . ?
C9 C10 C11 121.0(3) . . ?
C12 C11 C10 120.6(3) . . ?
C11 C12 C2 120.3(4) . . ?
C14 C13 C5 119.9(3) . . ?
C13 C14 C15 120.4(3) . . ?
C16 C15 C14 120.7(3) . . ?
C15 C16 C6 119.8(3) . . ?
C22 C17 C18 117.5(3) . . ?
C22 C17 C4 121.4(3) . . ?
C18 C17 C4 121.1(3) . . ?
C19 C18 C17 120.9(3) . . ?
C18 C19 C20 121.7(3) . . ?
C21 C20 C19 117.4(3) . . ?
C21 C20 C23 122.2(3) . . ?
C19 C20 C23 120.4(3) . . ?
C20 C21 C22 121.6(3) . . ?
C21 C22 C17 120.8(3) . . ?

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
C7 N1 C1 C2 -1.6(4) . . . . ?
C7 N1 C1 C9 178.7(2) . . . . ?
N1 C1 C2 C3 2.3(4) . . . . ?
C9 C1 C2 C3 -178.0(2) . . . . ?
N1 C1 C2 C12 -179.0(3) . . . . ?
C9 C1 C2 C12 0.8(4) . . . . ?
C1 C2 C3 C8 -1.0(4) . . . . ?
C12 C2 C3 C8 -179.7(3) . . . . ?
C8 C4 N2 C5 4.0(4) . . . . ?
C17 C4 N2 C5 -175.6(2) . . . . ?
C4 N2 C5 C6 -0.6(4) . . . . ?
C4 N2 C5 C13 177.7(2) . . . . ?
N2 C5 C6 C16 176.6(3) . . . . ?
C13 C5 C6 C16 -1.6(4) . . . . ?
N2 C5 C6 C7 -3.1(4) . . . . ?
C13 C5 C6 C7 178.7(2) . . . . ?
C1 N1 C7 C8 -0.4(4) . . . . ?
C1 N1 C7 C6 178.9(2) . . . . ?
C5 C6 C7 N1 -176.1(2) . . . . ?
C16 C6 C7 N1 4.2(4) . . . . ?
C5 C6 C7 C8 3.2(4) . . . . ?
C16 C6 C7 C8 -176.5(3) . . . . ?
C2 C3 C8 C7 -0.8(4) . . . . ?
C2 C3 C8 C4 -178.3(2) . . . . ?
N1 C7 C8 C3 1.6(4) . . . . ?
C6 C7 C8 C3 -177.7(2) . . . . ?
N1 C7 C8 C4 179.2(2) . . . . ?
C6 C7 C8 C4 -0.1(4) . . . . ?
N2 C4 C8 C3 173.8(3) . . . . ?
C17 C4 C8 C3 -6.6(4) . . . . ?
N2 C4 C8 C7 -3.8(4) . . . . ?
C17 C4 C8 C7 175.9(3) . . . . ?
N1 C1 C9 C10 178.6(3) . . . . ?
C2 C1 C9 C10 -1.1(4) . . . . ?
C1 C9 C10 C11 1.1(5) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C2 0.4(5) . . . . ?
C3 C2 C12 C11 178.3(3) . . . . ?
C1 C2 C12 C11 -0.4(4) . . . . ?
C6 C5 C13 C14 0.2(4) . . . . ?
N2 C5 C13 C14 -178.1(3) . . . . ?
C5 C13 C14 C15 0.8(5) . . . . ?
C13 C14 C15 C16 -0.4(5) . . . . ?
C14 C15 C16 C6 -0.9(4) . . . . ?
C5 C6 C16 C15 1.9(4) . . . . ?
C7 C6 C16 C15 -178.4(3) . . . . ?
N2 C4 C17 C22 -56.1(4) . . . . ?
C8 C4 C17 C22 124.3(3) . . . . ?
N2 C4 C17 C18 123.3(3) . . . . ?
C8 C4 C17 C18 -56.3(4) . . . . ?
C22 C17 C18 C19 1.0(4) . . . . ?
C4 C17 C18 C19 -178.4(3) . . . . ?
C17 C18 C19 C20 -1.1(5) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C18 C19 C20 C23 -179.7(3) . . . . ?
C19 C20 C21 C22 0.7(4) . . . . ?
C23 C20 C21 C22 -179.4(3) . . . . ?
C20 C21 C22 C17 -0.8(5) . . . . ?
C18 C17 C22 C21 -0.1(4) . . . . ?
C4 C17 C22 C21 179.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 1003843'
