# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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.
#
data_toa_077
_audit_creation_date             2014-03-20
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(Br), 2(C20 H17 N4 O2), C H2 Cl2'
_chemical_formula_sum            'C41 H36 Br2 Cl2 N8 O4'
_chemical_formula_weight         935.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H17 Br N4 O2'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.6382(7)
_cell_length_b                   10.7068(3)
_cell_length_c                   21.8503(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.245(5)
_cell_angle_gamma                90.00
_cell_volume                     4008.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4367
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.8505
_cell_measurement_theta_min      2.6622
_exptl_absorpt_coefficient_mu    2.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1896
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11961
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.67
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00   44.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223   57.0000  -30.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega  -81.00  -42.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  124.0000   82.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -93.00  -17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  -57.0000 -180.0000 76

#__ type_ start__ end____ width___ exp.time_
  4 omega   13.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   57.0000   60.0000 63

#__ type_ start__ end____ width___ exp.time_
  5 omega  -67.00  -17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223   19.0000  -90.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0166601000
_diffrn_orient_matrix_UB_12      0.0447740000
_diffrn_orient_matrix_UB_13      -0.0273727000
_diffrn_orient_matrix_UB_21      -0.0161961000
_diffrn_orient_matrix_UB_22      -0.0488201000
_diffrn_orient_matrix_UB_23      -0.0249698000
_diffrn_orient_matrix_UB_31      -0.0342545000
_diffrn_orient_matrix_UB_32      0.0013476000
_diffrn_orient_matrix_UB_33      0.0031918000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3828
_reflns_number_total             4613
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.019
_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)+(0.0297P)²+5.9334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0784
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Br1 Br 0.660307(13) 0.40943(2) 0.292187(12) 0.01792(8) Uani 1 1 d . . .
O2 O 1.00291(9) 0.51790(18) 0.59197(9) 0.0244(4) Uani 1 1 d . . .
O3 O 1.01515(9) 0.43030(17) 0.68619(9) 0.0232(4) Uani 1 1 d . . .
N4 N 0.97550(11) 0.46671(19) 0.62560(10) 0.0168(4) Uani 1 1 d . . .
N5 N 0.61676(10) 0.31058(18) 0.57738(9) 0.0116(4) Uani 1 1 d . . .
N6 N 0.64619(10) 0.21289(18) 0.67388(9) 0.0128(4) Uani 1 1 d . . .
N1 N 0.60435(10) 0.38568(18) 0.41223(10) 0.0136(4) Uani 1 1 d . . .
H1 H 0.6223 0.4096 0.3853 0.016 Uiso 1 1 calc R . .
C2 C 0.64989(12) 0.3389(2) 0.68787(12) 0.0155(5) Uani 1 1 d . . .
H2 H 0.6626 0.3751 0.7308 0.019 Uiso 1 1 calc R . .
C3 C 0.89096(12) 0.4457(2) 0.59056(12) 0.0136(5) Uani 1 1 d . . .
C4 C 0.29712(13) 0.2587(2) 0.43166(13) 0.0203(5) Uani 1 1 d . . .
H4 H 0.2476 0.2485 0.4266 0.024 Uiso 1 1 calc R . .
C5 C 0.62616(12) 0.1980(2) 0.60701(11) 0.0122(4) Uani 1 1 d . . .
H5 H 0.6197 0.1218 0.5844 0.015 Uiso 1 1 calc R . .
C6 C 0.73229(12) 0.3969(2) 0.52125(12) 0.0121(4) Uani 1 1 d . . .
C7 C 0.44509(12) 0.2963(2) 0.44499(11) 0.0125(5) Uani 1 1 d . . .
C8 C 0.42892(13) 0.3344(2) 0.49783(12) 0.0145(5) Uani 1 1 d . . .
H8 H 0.4678 0.3723 0.5381 0.017 Uiso 1 1 calc R . .
C9 C 0.35560(13) 0.3163(2) 0.49078(13) 0.0174(5) Uani 1 1 d . . .
H9 H 0.3455 0.3431 0.5261 0.021 Uiso 1 1 calc R . .
C10 C 0.76691(13) 0.4611(2) 0.48747(12) 0.0137(5) Uani 1 1 d . . .
H10 H 0.7362 0.4876 0.4414 0.016 Uiso 1 1 calc R . .
C11 C 0.64830(12) 0.3709(2) 0.48353(12) 0.0124(4) Uani 1 1 d . . .
C12 C 0.84621(13) 0.4855(2) 0.52197(12) 0.0143(5) Uani 1 1 d . . .
H12 H 0.8690 0.5279 0.4994 0.017 Uiso 1 1 calc R . .
C13 C 0.51984(12) 0.3255(2) 0.44731(11) 0.0123(4) Uani 1 1 d . . .
C14 C 0.85905(13) 0.3836(2) 0.62614(12) 0.0146(5) Uani 1 1 d . . .
H14 H 0.8902 0.3588 0.6725 0.017 Uiso 1 1 calc R . .
C15 C 0.52848(13) 0.3572(2) 0.39027(12) 0.0146(5) Uani 1 1 d . . .
H15 H 0.4885 0.3589 0.3439 0.018 Uiso 1 1 calc R . .
C16 C 0.59612(12) 0.3336(2) 0.50577(11) 0.0120(4) Uani 1 1 d . . .
C17 C 0.63168(13) 0.4001(2) 0.62779(12) 0.0162(5) Uani 1 1 d . . .
H17 H 0.6296 0.4862 0.6216 0.019 Uiso 1 1 calc R . .
C18 C 0.77978(13) 0.3591(2) 0.59113(12) 0.0144(5) Uani 1 1 d . . .
H18 H 0.7576 0.3169 0.6142 0.017 Uiso 1 1 calc R . .
C19 C 0.38609(13) 0.2355(2) 0.38610(12) 0.0157(5) Uani 1 1 d . . .
H19 H 0.3959 0.2078 0.3508 0.019 Uiso 1 1 calc R . .
C1A C 0.66479(14) 0.1128(2) 0.72561(12) 0.0184(5) Uani 1 1 d . . .
H1AA H 0.7198 0.1130 0.7580 0.028 Uiso 1 1 calc R . .
H1AB H 0.6500 0.0337 0.7020 0.028 Uiso 1 1 calc R . .
H1AC H 0.6367 0.1263 0.7507 0.028 Uiso 1 1 calc R . .
C1B C 0.31317(13) 0.2165(2) 0.38005(13) 0.0200(5) Uani 1 1 d . . .
H1B H 0.2747 0.1751 0.3410 0.024 Uiso 1 1 calc R . .
C1C C 0.5000 0.6357(4) 0.2500 0.0230(8) Uani 1 2 d S . .
H1CA H 0.4619 0.5825 0.2532 0.028 Uiso 0.50 1 calc PR . .
H1CB H 0.5381 0.5825 0.2468 0.028 Uiso 0.50 1 calc PR . .
Cl2 Cl 0.45310(5) 0.72883(8) 0.17414(4) 0.0436(2) Uani 1 1 d . . .


_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
O2 N4 1.232(3) . ?
O3 N4 1.226(2) . ?
N4 C3 1.467(3) . ?
N5 C5 1.338(3) . ?
N5 C16 1.433(3) . ?
N5 C17 1.379(3) . ?
N6 C2 1.377(3) . ?
N6 C5 1.324(3) . ?
N6 C1A 1.468(3) . ?
N1 C11 1.372(3) . ?
N1 C15 1.358(3) . ?
C2 C17 1.350(3) . ?
C3 C12 1.383(3) . ?
C3 C14 1.384(3) . ?
C4 C9 1.385(4) . ?
C4 C1B 1.387(4) . ?
C6 C10 1.404(3) . ?
C6 C11 1.466(3) . ?
C6 C18 1.405(3) . ?
C7 C8 1.400(3) . ?
C7 C13 1.477(3) . ?
C7 C19 1.402(3) . ?
C8 C9 1.385(3) . ?
C10 C12 1.384(3) . ?
C11 C16 1.390(3) . ?
C13 C15 1.380(3) . ?
C13 C16 1.419(3) . ?
C14 C18 1.383(3) . ?
C19 C1B 1.387(3) . ?
C1C Cl2 1.760(2) 2_655 ?
C1C Cl2 1.760(2) . ?

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
O2 N4 C3 118.03(19) . . ?
O3 N4 O2 123.61(19) . . ?
O3 N4 C3 118.34(19) . . ?
C5 N5 C16 125.58(19) . . ?
C5 N5 C17 108.32(19) . . ?
C17 N5 C16 126.1(2) . . ?
C2 N6 C1A 125.28(19) . . ?
C5 N6 C2 108.54(19) . . ?
C5 N6 C1A 126.1(2) . . ?
C15 N1 C11 110.37(19) . . ?
C17 C2 N6 107.4(2) . . ?
C12 C3 N4 118.5(2) . . ?
C12 C3 C14 122.3(2) . . ?
C14 C3 N4 119.2(2) . . ?
C9 C4 C1B 119.3(2) . . ?
N6 C5 N5 108.8(2) . . ?
C10 C6 C11 119.9(2) . . ?
C10 C6 C18 118.5(2) . . ?
C18 C6 C11 121.6(2) . . ?
C8 C7 C13 122.1(2) . . ?
C8 C7 C19 118.3(2) . . ?
C19 C7 C13 119.4(2) . . ?
C9 C8 C7 120.7(2) . . ?
C8 C9 C4 120.6(2) . . ?
C12 C10 C6 120.8(2) . . ?
N1 C11 C6 121.8(2) . . ?
N1 C11 C16 105.54(19) . . ?
C16 C11 C6 132.6(2) . . ?
C3 C12 C10 118.8(2) . . ?
C15 C13 C7 125.4(2) . . ?
C15 C13 C16 104.86(19) . . ?
C16 C13 C7 129.7(2) . . ?
C18 C14 C3 118.5(2) . . ?
N1 C15 C13 109.5(2) . . ?
C11 C16 N5 124.58(19) . . ?
C11 C16 C13 109.7(2) . . ?
C13 C16 N5 125.7(2) . . ?
C2 C17 N5 106.9(2) . . ?
C14 C18 C6 121.1(2) . . ?
C1B C19 C7 120.5(2) . . ?
C4 C1B C19 120.6(2) . . ?
Cl2 C1C Cl2 111.0(2) 2_655 . ?

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
O2 N4 C3 C12 -0.7(3) . . . . ?
O2 N4 C3 C14 177.2(2) . . . . ?
O3 N4 C3 C12 -179.3(2) . . . . ?
O3 N4 C3 C14 -1.4(3) . . . . ?
N4 C3 C12 C10 177.2(2) . . . . ?
N4 C3 C14 C18 -176.8(2) . . . . ?
N6 C2 C17 N5 0.2(2) . . . . ?
N1 C11 C16 N5 -178.2(2) . . . . ?
N1 C11 C16 C13 0.1(3) . . . . ?
C2 N6 C5 N5 0.0(2) . . . . ?
C3 C14 C18 C6 -0.5(3) . . . . ?
C5 N5 C16 C11 -102.7(3) . . . . ?
C5 N5 C16 C13 79.2(3) . . . . ?
C5 N5 C17 C2 -0.2(2) . . . . ?
C5 N6 C2 C17 -0.1(2) . . . . ?
C6 C10 C12 C3 -0.1(3) . . . . ?
C6 C11 C16 N5 -0.3(4) . . . . ?
C6 C11 C16 C13 178.1(2) . . . . ?
C7 C8 C9 C4 0.8(4) . . . . ?
C7 C13 C15 N1 176.1(2) . . . . ?
C7 C13 C16 N5 1.9(4) . . . . ?
C7 C13 C16 C11 -176.5(2) . . . . ?
C7 C19 C1B C4 0.9(4) . . . . ?
C8 C7 C13 C15 -141.8(2) . . . . ?
C8 C7 C13 C16 34.9(4) . . . . ?
C8 C7 C19 C1B 1.4(3) . . . . ?
C9 C4 C1B C19 -2.3(4) . . . . ?
C10 C6 C11 N1 12.7(3) . . . . ?
C10 C6 C11 C16 -165.0(2) . . . . ?
C10 C6 C18 C14 -0.4(3) . . . . ?
C11 N1 C15 C13 1.5(3) . . . . ?
C11 C6 C10 C12 -179.4(2) . . . . ?
C11 C6 C18 C14 179.7(2) . . . . ?
C12 C3 C14 C18 1.0(4) . . . . ?
C13 C7 C8 C9 173.6(2) . . . . ?
C13 C7 C19 C1B -174.6(2) . . . . ?
C14 C3 C12 C10 -0.7(4) . . . . ?
C15 N1 C11 C6 -179.2(2) . . . . ?
C15 N1 C11 C16 -1.0(3) . . . . ?
C15 C13 C16 N5 179.1(2) . . . . ?
C15 C13 C16 C11 0.7(3) . . . . ?
C16 N5 C5 N6 179.09(19) . . . . ?
C16 N5 C17 C2 -179.1(2) . . . . ?
C16 C13 C15 N1 -1.3(3) . . . . ?
C17 N5 C5 N6 0.1(2) . . . . ?
C17 N5 C16 C11 76.1(3) . . . . ?
C17 N5 C16 C13 -102.0(3) . . . . ?
C18 C6 C10 C12 0.7(3) . . . . ?
C18 C6 C11 N1 -167.4(2) . . . . ?
C18 C6 C11 C16 14.9(4) . . . . ?
C19 C7 C8 C9 -2.2(3) . . . . ?
C19 C7 C13 C15 34.0(3) . . . . ?
C19 C7 C13 C16 -149.3(2) . . . . ?
C1A N6 C2 C17 177.5(2) . . . . ?
C1A N6 C5 N5 -177.58(19) . . . . ?
C1B C4 C9 C8 1.5(4) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 992831'
#######################################################################
#
#                 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_funt2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 Br N4'
_chemical_formula_weight         496.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1221(2)
_cell_length_b                   10.9612(3)
_cell_length_c                   12.8679(3)
_cell_angle_alpha                71.798(2)
_cell_angle_beta                 79.244(2)
_cell_angle_gamma                88.953(2)
_cell_volume                     1199.69(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15533
_cell_measurement_theta_min      3.6803
_cell_measurement_theta_max      76.5020

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             510
_exptl_absorpt_coefficient_mu    2.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46988
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22772
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.68
_diffrn_reflns_theta_max         70.99
_reflns_number_total             4636
_reflns_number_gt                4507
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0507P)²+4.6368P] 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         4636
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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
Br1 Br 0.31120(4) 0.20299(4) 0.93995(4) 0.03384(15) Uani 1 1 d . . .
N1 N -0.2092(4) 0.5100(3) 1.0441(3) 0.0321(7) Uani 1 1 d . . .
N3 N -0.2645(3) 0.1085(3) 0.8701(3) 0.0262(7) Uani 1 1 d . . .
C21 C -0.1293(4) 0.1819(4) 1.1995(3) 0.0267(8) Uani 1 1 d . . .
C1 C -0.0713(4) 0.1571(4) 0.9312(3) 0.0283(8) Uani 1 1 d . . .
H1 H 0.0230 0.1604 0.9481 0.034 Uiso 1 1 calc R . .
C2 C -0.1177(4) 0.0813(4) 0.8779(3) 0.0290(8) Uani 1 1 d . . .
H2 H -0.0615 0.0219 0.8514 0.035 Uiso 1 1 calc R . .
C3 C -0.3070(4) 0.1979(4) 0.9179(3) 0.0263(8) Uani 1 1 d . . .
H3 H -0.4009 0.2326 0.9237 0.032 Uiso 1 1 calc R . .
N2 N -0.1917(3) 0.2292(3) 0.9560(3) 0.0247(6) Uani 1 1 d . . .
C20 C -0.1579(4) 0.3036(4) 1.1183(3) 0.0276(8) Uani 1 1 d . . .
C12 C -0.2225(4) 0.4519(4) 0.9658(3) 0.0287(8) Uani 1 1 d . . .
C13 C -0.2598(4) 0.5240(4) 0.8569(3) 0.0308(8) Uani 1 1 d . . .
C5 C -0.3299(4) 0.1236(4) 0.6884(3) 0.0300(8) Uani 1 1 d . . .
C23 C -0.0004(5) 0.0632(4) 1.3459(3) 0.0342(9) Uani 1 1 d . . .
H23 H 0.0723 0.0610 1.3883 0.041 Uiso 1 1 calc R . .
C4 C -0.3550(5) 0.0533(4) 0.8116(3) 0.0312(8) Uani 1 1 d . . .
H4A H -0.4597 0.0554 0.8435 0.037 Uiso 1 1 calc R . .
H4B H -0.3311 -0.0360 0.8230 0.037 Uiso 1 1 calc R . .
C11 C -0.1920(4) 0.3250(4) 1.0108(3) 0.0264(8) Uani 1 1 d . . .
C19 C -0.1691(4) 0.4223(4) 1.1344(3) 0.0303(8) Uani 1 1 d . . .
H19 H -0.1520 0.4399 1.1974 0.036 Uiso 1 1 calc R . .
C18 C -0.3710(5) 0.6126(4) 0.8495(4) 0.0358(9) Uani 1 1 d . . .
H18 H -0.4244 0.6251 0.9141 0.043 Uiso 1 1 calc R . .
C26 C -0.2155(4) 0.0708(4) 1.2188(3) 0.0321(8) Uani 1 1 d . . .
H26 H -0.2876 0.0723 1.1760 0.038 Uiso 1 1 calc R . .
C10 C -0.4015(5) 0.0760(4) 0.6227(4) 0.0382(10) Uani 1 1 d . . .
H10 H -0.4614 0.0010 0.6550 0.046 Uiso 1 1 calc R . .
C14 C -0.1809(5) 0.5060(4) 0.7590(3) 0.0332(9) Uani 1 1 d . . .
H14 H -0.1063 0.4466 0.7626 0.040 Uiso 1 1 calc R . .
C17 C -0.4033(5) 0.6828(4) 0.7469(4) 0.0422(10) Uani 1 1 d . . .
H17 H -0.4783 0.7418 0.7429 0.051 Uiso 1 1 calc R . .
C24 C -0.0891(5) -0.0465(4) 1.3657(3) 0.0367(9) Uani 1 1 d . . .
H24 H -0.0771 -0.1217 1.4217 0.044 Uiso 1 1 calc R . .
C6 C -0.2339(5) 0.2317(5) 0.6364(4) 0.0412(10) Uani 1 1 d . . .
H6 H -0.1807 0.2628 0.6785 0.049 Uiso 1 1 calc R . .
C22 C -0.0193(5) 0.1756(4) 1.2637(3) 0.0309(8) Uani 1 1 d . . .
H22 H 0.0417 0.2479 1.2509 0.037 Uiso 1 1 calc R . .
C25 C -0.1957(5) -0.0423(4) 1.3010(4) 0.0371(9) Uani 1 1 d . . .
H25 H -0.2543 -0.1156 1.3126 0.045 Uiso 1 1 calc R . .
C16 C -0.3237(6) 0.6650(4) 0.6501(4) 0.0433(11) Uani 1 1 d . . .
H16 H -0.3445 0.7125 0.5812 0.052 Uiso 1 1 calc R . .
C15 C -0.2133(5) 0.5764(4) 0.6565(4) 0.0408(10) Uani 1 1 d . . .
H15 H -0.1605 0.5639 0.5917 0.049 Uiso 1 1 calc R . .
C7 C -0.2169(5) 0.2931(5) 0.5231(4) 0.0437(11) Uani 1 1 d . . .
H7 H -0.1519 0.3647 0.4892 0.052 Uiso 1 1 calc R . .
C8 C -0.2970(5) 0.2477(5) 0.4598(4) 0.0415(10) Uani 1 1 d . . .
H8 H -0.2903 0.2916 0.3843 0.050 Uiso 1 1 calc R . .
C9 C -0.3851(6) 0.1387(5) 0.5089(4) 0.0438(11) Uani 1 1 d . . .
H9 H -0.4349 0.1058 0.4661 0.053 Uiso 1 1 calc R . .
N1A N 0.1372(9) 0.3837(6) 0.6405(5) 0.0903(19) Uani 1 1 d . . .
C1A C 0.4028(8) 0.4017(6) 0.6481(5) 0.0675(17) Uani 1 1 d . . .
H1AA H 0.4473 0.3583 0.5966 0.101 Uiso 1 1 calc R . .
H1AB H 0.4342 0.3644 0.7180 0.101 Uiso 1 1 calc R . .
H1AC H 0.4336 0.4911 0.6187 0.101 Uiso 1 1 calc R . .
C2A C 0.2467(8) 0.3891(6) 0.6642(8) 0.085(3) Uani 1 1 d . . .


_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 C19 1.362(5) . ?
N1 C12 1.373(5) . ?
N3 C3 1.327(5) . ?
N3 C2 1.382(5) . ?
N3 C4 1.466(5) . ?
C21 C26 1.391(6) . ?
C21 C22 1.402(5) . ?
C21 C20 1.469(5) . ?
C1 C2 1.348(6) . ?
C1 N2 1.388(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 N2 1.333(5) . ?
C3 H3 0.9300 . ?
N2 C11 1.436(5) . ?
C20 C19 1.380(6) . ?
C20 C11 1.422(5) . ?
C12 C11 1.375(6) . ?
C12 C13 1.477(5) . ?
C13 C18 1.387(6) . ?
C13 C14 1.399(6) . ?
C5 C10 1.382(6) . ?
C5 C6 1.393(6) . ?
C5 C4 1.506(5) . ?
C23 C22 1.383(6) . ?
C23 C24 1.391(6) . ?
C23 H23 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C19 H19 0.9300 . ?
C18 C17 1.388(6) . ?
C18 H18 0.9300 . ?
C26 C25 1.391(6) . ?
C26 H26 0.9300 . ?
C10 C9 1.390(6) . ?
C10 H10 0.9300 . ?
C14 C15 1.387(6) . ?
C14 H14 0.9300 . ?
C17 C16 1.388(7) . ?
C17 H17 0.9300 . ?
C24 C25 1.384(6) . ?
C24 H24 0.9300 . ?
C6 C7 1.382(6) . ?
C6 H6 0.9300 . ?
C22 H22 0.9300 . ?
C25 H25 0.9300 . ?
C16 C15 1.382(7) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C7 C8 1.391(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.358(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
N1A C2A 1.104(9) . ?
C1A C2A 1.403(9) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 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
C19 N1 C12 109.7(3) . . ?
C3 N3 C2 109.3(3) . . ?
C3 N3 C4 125.6(3) . . ?
C2 N3 C4 125.0(3) . . ?
C26 C21 C22 118.0(4) . . ?
C26 C21 C20 120.9(3) . . ?
C22 C21 C20 121.0(4) . . ?
C2 C1 N2 106.7(3) . . ?
C2 C1 H1 126.7 . . ?
N2 C1 H1 126.7 . . ?
C1 C2 N3 107.1(3) . . ?
C1 C2 H2 126.5 . . ?
N3 C2 H2 126.5 . . ?
N3 C3 N2 108.0(3) . . ?
N3 C3 H3 126.0 . . ?
N2 C3 H3 126.0 . . ?
C3 N2 C1 109.0(3) . . ?
C3 N2 C11 125.0(3) . . ?
C1 N2 C11 126.0(3) . . ?
C19 C20 C11 104.5(3) . . ?
C19 C20 C21 126.6(4) . . ?
C11 C20 C21 128.7(4) . . ?
N1 C12 C11 106.2(3) . . ?
N1 C12 C13 122.2(4) . . ?
C11 C12 C13 131.7(4) . . ?
C18 C13 C14 118.9(4) . . ?
C18 C13 C12 120.7(4) . . ?
C14 C13 C12 120.4(4) . . ?
C10 C5 C6 118.1(4) . . ?
C10 C5 C4 118.4(4) . . ?
C6 C5 C4 123.4(4) . . ?
C22 C23 C24 120.6(4) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
N3 C4 C5 112.8(3) . . ?
N3 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N3 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C12 C11 C20 109.9(3) . . ?
C12 C11 N2 124.9(3) . . ?
C20 C11 N2 125.2(3) . . ?
N1 C19 C20 109.7(3) . . ?
N1 C19 H19 125.1 . . ?
C20 C19 H19 125.1 . . ?
C13 C18 C17 120.7(4) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C25 C26 C21 121.1(4) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?
C5 C10 C9 120.8(4) . . ?
C5 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C25 C24 C23 119.1(4) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C23 C22 C21 120.8(4) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C25 C26 120.4(4) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C6 C7 C8 120.0(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 119.5(4) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N1A C2A C1A 156.6(10) . . ?

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
N2 C1 C2 N3 0.4(4) . . . . ?
C3 N3 C2 C1 -0.4(4) . . . . ?
C4 N3 C2 C1 175.9(3) . . . . ?
C2 N3 C3 N2 0.1(4) . . . . ?
C4 N3 C3 N2 -176.1(3) . . . . ?
N3 C3 N2 C1 0.2(4) . . . . ?
N3 C3 N2 C11 178.4(3) . . . . ?
C2 C1 N2 C3 -0.4(4) . . . . ?
C2 C1 N2 C11 -178.6(3) . . . . ?
C26 C21 C20 C19 132.5(4) . . . . ?
C22 C21 C20 C19 -44.3(6) . . . . ?
C26 C21 C20 C11 -41.8(6) . . . . ?
C22 C21 C20 C11 141.3(4) . . . . ?
C19 N1 C12 C11 0.9(4) . . . . ?
C19 N1 C12 C13 -177.9(4) . . . . ?
N1 C12 C13 C18 -43.7(6) . . . . ?
C11 C12 C13 C18 137.8(5) . . . . ?
N1 C12 C13 C14 134.8(4) . . . . ?
C11 C12 C13 C14 -43.7(6) . . . . ?
C3 N3 C4 C5 92.1(5) . . . . ?
C2 N3 C4 C5 -83.6(5) . . . . ?
C10 C5 C4 N3 175.9(4) . . . . ?
C6 C5 C4 N3 -1.6(6) . . . . ?
N1 C12 C11 C20 -0.5(4) . . . . ?
C13 C12 C11 C20 178.2(4) . . . . ?
N1 C12 C11 N2 -179.3(3) . . . . ?
C13 C12 C11 N2 -0.6(7) . . . . ?
C19 C20 C11 C12 -0.2(4) . . . . ?
C21 C20 C11 C12 175.1(4) . . . . ?
C19 C20 C11 N2 178.6(3) . . . . ?
C21 C20 C11 N2 -6.1(6) . . . . ?
C3 N2 C11 C12 -57.4(5) . . . . ?
C1 N2 C11 C12 120.6(4) . . . . ?
C3 N2 C11 C20 124.0(4) . . . . ?
C1 N2 C11 C20 -58.0(5) . . . . ?
C12 N1 C19 C20 -1.1(5) . . . . ?
C11 C20 C19 N1 0.8(4) . . . . ?
C21 C20 C19 N1 -174.7(4) . . . . ?
C14 C13 C18 C17 -0.2(6) . . . . ?
C12 C13 C18 C17 178.3(4) . . . . ?
C22 C21 C26 C25 1.4(6) . . . . ?
C20 C21 C26 C25 -175.5(4) . . . . ?
C6 C5 C10 C9 -3.8(7) . . . . ?
C4 C5 C10 C9 178.5(4) . . . . ?
C18 C13 C14 C15 0.3(6) . . . . ?
C12 C13 C14 C15 -178.2(4) . . . . ?
C13 C18 C17 C16 -0.2(7) . . . . ?
C22 C23 C24 C25 0.8(6) . . . . ?
C10 C5 C6 C7 3.3(7) . . . . ?
C4 C5 C6 C7 -179.2(4) . . . . ?
C24 C23 C22 C21 0.8(6) . . . . ?
C26 C21 C22 C23 -1.9(6) . . . . ?
C20 C21 C22 C23 175.1(4) . . . . ?
C23 C24 C25 C26 -1.2(6) . . . . ?
C21 C26 C25 C24 0.1(6) . . . . ?
C18 C17 C16 C15 0.6(7) . . . . ?
C17 C16 C15 C14 -0.5(7) . . . . ?
C13 C14 C15 C16 0.1(6) . . . . ?
C5 C6 C7 C8 0.5(7) . . . . ?
C6 C7 C8 C9 -3.7(8) . . . . ?
C7 C8 C9 C10 3.2(8) . . . . ?
C5 C10 C9 C8 0.7(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        70.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.823
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.091
_database_code_depnum_ccdc_archive 'CCDC 992996'
#######################################################################
#
#                 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_ole1
_audit_creation_date             2013-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H16 N4 O2'
_chemical_formula_sum            'C20 H16 N4 O2'
_chemical_formula_weight         344.37
_chemical_melting_point          ?

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.4914(4)
_cell_length_b                   11.8011(3)
_cell_length_c                   13.0430(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.162(5)
_cell_angle_gamma                90.00
_cell_volume                     1690.02(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5541
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5772
_cell_measurement_theta_min      2.6968
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7769
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9597
_diffrn_measured_fraction_theta_max 0.9597
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0542389000
_diffrn_orient_matrix_UB_12      -0.0197775000
_diffrn_orient_matrix_UB_13      -0.0094042000
_diffrn_orient_matrix_UB_21      -0.0275236000
_diffrn_orient_matrix_UB_22      0.0056666000
_diffrn_orient_matrix_UB_23      -0.0560887000
_diffrn_orient_matrix_UB_31      0.0218171000
_diffrn_orient_matrix_UB_32      0.0564512000
_diffrn_orient_matrix_UB_33      0.0023565000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_number_gt                2331
_reflns_number_total             2827
_reflns_odcompleteness_completeness 92.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.124
_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/[σ²(Fo²)+(0.0173P)²+2.9620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1171
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C23(H23), C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.98180(18) 0.98571(16) 0.24816(16) 0.0153(4) Uani 1 1 d . . .
N2 N 1.55339(19) 0.90221(17) 0.30552(17) 0.0197(5) Uani 1 1 d . . .
N3 N 1.03653(18) 1.19552(15) 0.06261(16) 0.0147(4) Uani 1 1 d . . .
O4 O 1.62539(16) 0.95630(15) 0.27009(15) 0.0252(4) Uani 1 1 d . . .
O5 O 1.58419(17) 0.81606(15) 0.36041(17) 0.0295(5) Uani 1 1 d . . .
N6 N 1.10796(19) 1.34787(16) 0.01250(17) 0.0169(4) Uani 1 1 d . . .
C7 C 1.4284(2) 0.9415(2) 0.2805(2) 0.0183(5) Uani 1 1 d . . .
C8 C 1.3458(2) 0.8795(2) 0.3165(2) 0.0205(6) Uani 1 1 d . . .
H8 H 1.3706 0.8145 0.3573 0.025 Uiso 1 1 calc R . .
C9 C 1.0582(2) 1.04413(19) 0.2032(2) 0.0168(5) Uani 1 1 d . . .
C10 C 0.7529(2) 1.15405(19) 0.0461(2) 0.0170(5) Uani 1 1 d . . .
C11 C 0.6386(2) 1.1149(2) 0.0498(2) 0.0199(6) Uani 1 1 d . . .
H11 H 0.6353 1.0573 0.0975 0.024 Uiso 1 1 calc R . .
C12 C 1.3940(2) 1.0395(2) 0.2214(2) 0.0188(5) Uani 1 1 d . . .
H12 H 1.4504 1.0806 0.1980 0.023 Uiso 1 1 calc R . .
C13 C 0.8641(2) 1.10455(19) 0.1188(2) 0.0157(5) Uani 1 1 d . . .
C14 C 0.8688(2) 1.02265(19) 0.1982(2) 0.0170(5) Uani 1 1 d . . .
H14 H 0.8000 0.9965 0.2146 0.020 Uiso 1 1 calc R . .
C15 C 1.1867(2) 1.01391(19) 0.23053(19) 0.0145(5) Uani 1 1 d . . .
C16 C 0.9886(2) 1.11854(18) 0.1259(2) 0.0147(5) Uani 1 1 d . . .
C17 C 0.5310(2) 1.1597(2) -0.0158(2) 0.0226(6) Uani 1 1 d . . .
H17 H 0.4568 1.1321 -0.0115 0.027 Uiso 1 1 calc R . .
C18 C 1.2747(2) 1.0758(2) 0.1977(2) 0.0170(5) Uani 1 1 d . . .
H18 H 1.2517 1.1426 0.1592 0.020 Uiso 1 1 calc R . .
C19 C 0.7525(2) 1.2389(2) -0.0291(2) 0.0202(6) Uani 1 1 d . . .
H19 H 0.8263 1.2656 -0.0353 0.024 Uiso 1 1 calc R . .
C20 C 1.0668(2) 1.30338(19) 0.0886(2) 0.0153(5) Uani 1 1 d . . .
H20 H 1.0601 1.3408 0.1494 0.018 Uiso 1 1 calc R . .
C21 C 1.2275(2) 0.9150(2) 0.2916(2) 0.0188(6) Uani 1 1 d . . .
H21 H 1.1723 0.8728 0.3154 0.023 Uiso 1 1 calc R . .
C22 C 1.1514(2) 1.4643(2) 0.0102(2) 0.0207(6) Uani 1 1 d . . .
H22A H 1.1437 1.5048 0.0717 0.031 Uiso 1 1 calc R . .
H22B H 1.1036 1.5013 -0.0541 0.031 Uiso 1 1 calc R . .
H22C H 1.2353 1.4632 0.0113 0.031 Uiso 1 1 calc R . .
C23 C 1.0598(2) 1.1710(2) -0.0327(2) 0.0188(5) Uani 1 1 d . . .
H23 H 1.0474 1.1019 -0.0685 0.023 Uiso 1 1 calc R . .
C24 C 1.1039(3) 1.2660(2) -0.0642(2) 0.0218(6) Uani 1 1 d . . .
H24 H 1.1274 1.2751 -0.1261 0.026 Uiso 1 1 calc R . .
C25 C 0.5330(2) 1.2456(2) -0.0877(2) 0.0214(6) Uani 1 1 d . . .
H25 H 0.4609 1.2770 -0.1308 0.026 Uiso 1 1 calc R . .
C26 C 0.6451(2) 1.2838(2) -0.0942(2) 0.0237(6) Uani 1 1 d . . .
H26 H 0.6478 1.3404 -0.1430 0.028 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 C9 1.377(3) . ?
N1 C14 1.342(3) . ?
N2 O4 1.238(3) . ?
N2 O5 1.234(3) . ?
N2 C7 1.452(3) . ?
N3 C16 1.441(3) . ?
N3 C20 1.336(3) . ?
N3 C23 1.378(3) . ?
N6 C20 1.327(3) . ?
N6 C22 1.465(3) . ?
N6 C24 1.381(3) . ?
C7 C8 1.386(3) . ?
C7 C12 1.382(3) . ?
C8 H8 0.9300 . ?
C8 C21 1.367(4) . ?
C9 C15 1.457(3) . ?
C9 C16 1.397(3) . ?
C10 C11 1.407(3) . ?
C10 C13 1.468(4) . ?
C10 C19 1.400(3) . ?
C11 H11 0.9300 . ?
C11 C17 1.384(4) . ?
C12 H12 0.9300 . ?
C12 C18 1.381(3) . ?
C13 C14 1.406(3) . ?
C13 C16 1.416(3) . ?
C14 H14 0.9300 . ?
C15 C18 1.412(3) . ?
C15 C21 1.413(3) . ?
C17 H17 0.9300 . ?
C17 C25 1.387(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C26 1.381(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C24 1.343(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.390(4) . ?
C26 H26 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
C14 N1 C9 106.2(2) . . ?
O4 N2 C7 118.5(2) . . ?
O5 N2 O4 122.2(2) . . ?
O5 N2 C7 119.3(2) . . ?
C20 N3 C16 124.8(2) . . ?
C20 N3 C23 108.85(19) . . ?
C23 N3 C16 126.39(19) . . ?
C20 N6 C22 125.8(2) . . ?
C20 N6 C24 108.75(19) . . ?
C24 N6 C22 125.4(2) . . ?
C8 C7 N2 119.1(2) . . ?
C12 C7 N2 119.6(2) . . ?
C12 C7 C8 121.3(2) . . ?
C7 C8 H8 120.3 . . ?
C21 C8 C7 119.4(2) . . ?
C21 C8 H8 120.3 . . ?
N1 C9 C15 120.1(2) . . ?
N1 C9 C16 108.7(2) . . ?
C16 C9 C15 130.8(2) . . ?
C11 C10 C13 119.4(2) . . ?
C19 C10 C11 116.6(2) . . ?
C19 C10 C13 124.0(2) . . ?
C10 C11 H11 119.1 . . ?
C17 C11 C10 121.8(2) . . ?
C17 C11 H11 119.1 . . ?
C7 C12 H12 120.4 . . ?
C18 C12 C7 119.1(2) . . ?
C18 C12 H12 120.4 . . ?
C14 C13 C10 125.9(2) . . ?
C14 C13 C16 102.3(2) . . ?
C16 C13 C10 131.7(2) . . ?
N1 C14 C13 113.7(2) . . ?
N1 C14 H14 123.1 . . ?
C13 C14 H14 123.1 . . ?
C18 C15 C9 124.3(2) . . ?
C18 C15 C21 116.7(2) . . ?
C21 C15 C9 119.0(2) . . ?
C9 C16 N3 125.1(2) . . ?
C9 C16 C13 109.0(2) . . ?
C13 C16 N3 125.8(2) . . ?
C11 C17 H17 119.8 . . ?
C11 C17 C25 120.5(2) . . ?
C25 C17 H17 119.8 . . ?
C12 C18 C15 121.6(2) . . ?
C12 C18 H18 119.2 . . ?
C15 C18 H18 119.2 . . ?
C10 C19 H19 119.2 . . ?
C26 C19 C10 121.5(2) . . ?
C26 C19 H19 119.2 . . ?
N3 C20 H20 125.9 . . ?
N6 C20 N3 108.1(2) . . ?
N6 C20 H20 125.9 . . ?
C8 C21 C15 121.9(2) . . ?
C8 C21 H21 119.0 . . ?
C15 C21 H21 119.0 . . ?
N6 C22 H22A 109.5 . . ?
N6 C22 H22B 109.5 . . ?
N6 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 H23 126.5 . . ?
C24 C23 N3 107.0(2) . . ?
C24 C23 H23 126.5 . . ?
N6 C24 H24 126.3 . . ?
C23 C24 N6 107.3(2) . . ?
C23 C24 H24 126.3 . . ?
C17 C25 H25 120.7 . . ?
C17 C25 C26 118.6(3) . . ?
C26 C25 H25 120.7 . . ?
C19 C26 C25 121.0(2) . . ?
C19 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?

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
N1 C9 C15 C18 -173.1(2) . . . . ?
N1 C9 C15 C21 8.6(3) . . . . ?
N1 C9 C16 N3 179.0(2) . . . . ?
N1 C9 C16 C13 -2.0(3) . . . . ?
N2 C7 C8 C21 -178.8(2) . . . . ?
N2 C7 C12 C18 179.7(2) . . . . ?
N3 C23 C24 N6 0.3(3) . . . . ?
O4 N2 C7 C8 177.8(2) . . . . ?
O4 N2 C7 C12 -2.2(3) . . . . ?
O5 N2 C7 C8 -1.7(4) . . . . ?
O5 N2 C7 C12 178.3(2) . . . . ?
C7 C8 C21 C15 -0.5(4) . . . . ?
C7 C12 C18 C15 -1.3(4) . . . . ?
C8 C7 C12 C18 -0.3(4) . . . . ?
C9 N1 C14 C13 0.6(3) . . . . ?
C9 C15 C18 C12 -176.5(2) . . . . ?
C9 C15 C21 C8 177.5(2) . . . . ?
C10 C11 C17 C25 0.0(4) . . . . ?
C10 C13 C14 N1 175.3(2) . . . . ?
C10 C13 C16 N3 4.4(4) . . . . ?
C10 C13 C16 C9 -174.7(2) . . . . ?
C10 C19 C26 C25 -0.4(4) . . . . ?
C11 C10 C13 C14 -3.3(4) . . . . ?
C11 C10 C13 C16 172.9(2) . . . . ?
C11 C10 C19 C26 1.7(4) . . . . ?
C11 C17 C25 C26 1.3(4) . . . . ?
C12 C7 C8 C21 1.2(4) . . . . ?
C13 C10 C11 C17 179.0(2) . . . . ?
C13 C10 C19 C26 -178.9(2) . . . . ?
C14 N1 C9 C15 -172.5(2) . . . . ?
C14 N1 C9 C16 0.9(3) . . . . ?
C14 C13 C16 N3 -178.8(2) . . . . ?
C14 C13 C16 C9 2.2(3) . . . . ?
C15 C9 C16 N3 -8.6(4) . . . . ?
C15 C9 C16 C13 170.4(2) . . . . ?
C16 N3 C20 N6 179.7(2) . . . . ?
C16 N3 C23 C24 -179.8(2) . . . . ?
C16 C9 C15 C18 15.2(4) . . . . ?
C16 C9 C15 C21 -163.2(2) . . . . ?
C16 C13 C14 N1 -1.8(3) . . . . ?
C17 C25 C26 C19 -1.2(4) . . . . ?
C18 C15 C21 C8 -0.9(4) . . . . ?
C19 C10 C11 C17 -1.5(4) . . . . ?
C19 C10 C13 C14 177.3(2) . . . . ?
C19 C10 C13 C16 -6.5(4) . . . . ?
C20 N3 C16 C9 -93.2(3) . . . . ?
C20 N3 C16 C13 88.0(3) . . . . ?
C20 N3 C23 C24 -0.3(3) . . . . ?
C20 N6 C24 C23 -0.2(3) . . . . ?
C21 C15 C18 C12 1.9(3) . . . . ?
C22 N6 C20 N3 -179.7(2) . . . . ?
C22 N6 C24 C23 179.5(2) . . . . ?
C23 N3 C16 C9 86.2(3) . . . . ?
C23 N3 C16 C13 -92.7(3) . . . . ?
C23 N3 C20 N6 0.2(3) . . . . ?
C24 N6 C20 N3 0.0(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 991739'
