# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_ch15119

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H32 N4 O4'
_chemical_formula_sum            'C34 H32 N4 O4'
_chemical_formula_weight         560.64

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'

_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                   10.786(3)
_cell_length_b                   11.071(3)
_cell_length_c                   12.689(3)
_cell_angle_alpha                67.852(4)
_cell_angle_beta                 80.937(4)
_cell_angle_gamma                81.886(5)
_cell_volume                     1380.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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            10954
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0943
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4790
_reflns_number_gt                2814
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0988P)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         4790
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1950
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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 1.2690(3) 0.1831(4) 0.5322(4) 0.0423(10) Uani 1 1 d . . .
C2 C 1.1732(3) 0.3960(4) 0.4344(3) 0.0294(9) Uani 1 1 d . . .
C3 C 1.1520(3) 0.5263(3) 0.4266(3) 0.0319(9) Uani 1 1 d . . .
H3 H 1.2000 0.5571 0.4665 0.038 Uiso 1 1 calc R . .
C4 C 1.0620(3) 0.6113(3) 0.3616(3) 0.0302(9) Uani 1 1 d . . .
H4 H 1.0476 0.7000 0.3562 0.036 Uiso 1 1 calc R . .
C5 C 0.9930(3) 0.5627(3) 0.3042(3) 0.0258(8) Uani 1 1 d . . .
C6 C 1.0143(3) 0.4323(3) 0.3100(3) 0.0239(8) Uani 1 1 d . . .
C7 C 1.1083(3) 0.3480(3) 0.3759(3) 0.0272(8) Uani 1 1 d . . .
H7 H 1.1260 0.2601 0.3795 0.033 Uiso 1 1 calc R . .
C8 C 0.9280(3) 0.4138(3) 0.2422(3) 0.0238(8) Uani 1 1 d . . .
C9 C 0.8585(3) 0.5307(3) 0.2009(3) 0.0268(8) Uani 1 1 d . . .
H9 H 0.7936 0.5472 0.1533 0.032 Uiso 1 1 calc R . .
C10 C 0.8516(3) 0.7573(3) 0.1980(3) 0.0263(8) Uani 1 1 d . . .
C11 C 0.9395(3) 0.8490(3) 0.1653(3) 0.0313(9) Uani 1 1 d . . .
H11 H 1.0262 0.8203 0.1715 0.038 Uiso 1 1 calc R . .
C12 C 0.9022(3) 0.9809(3) 0.1242(3) 0.0357(9) Uani 1 1 d . . .
H12 H 0.9628 1.0424 0.1059 0.043 Uiso 1 1 calc R . .
C13 C 0.7779(4) 1.0247(4) 0.1092(3) 0.0378(10) Uani 1 1 d . . .
H13 H 0.7527 1.1159 0.0794 0.045 Uiso 1 1 calc R . .
C14 C 0.6904(3) 0.9342(3) 0.1382(3) 0.0350(9) Uani 1 1 d . . .
H14 H 0.6050 0.9642 0.1261 0.042 Uiso 1 1 calc R . .
C15 C 0.7241(3) 0.8011(3) 0.1843(3) 0.0284(8) Uani 1 1 d . . .
C16 C 0.6195(3) 0.7144(3) 0.2145(3) 0.0284(8) Uani 1 1 d . . .
C17 C 0.5078(4) 0.5338(4) 0.3509(4) 0.0465(11) Uani 1 1 d . . .
C18 C 0.9208(3) 0.2952(3) 0.2126(3) 0.0237(8) Uani 1 1 d . . .
H18 H 1.0007 0.2868 0.1629 0.028 Uiso 1 1 calc R . .
C19 C 0.9177(3) 0.1647(3) 0.3174(3) 0.0267(8) Uani 1 1 d . . .
H19A H 0.8977 0.0956 0.2927 0.032 Uiso 1 1 calc R . .
H19B H 1.0030 0.1398 0.3427 0.032 Uiso 1 1 calc R . .
C20 C 0.8256(3) 0.1678(3) 0.4174(3) 0.0244(8) Uani 1 1 d . . .
C21 C 0.8626(3) 0.1285(3) 0.5267(3) 0.0268(8) Uani 1 1 d . . .
H21 H 0.9494 0.1048 0.5363 0.032 Uiso 1 1 calc R . .
C22 C 0.7775(3) 0.1228(3) 0.6216(3) 0.0288(9) Uani 1 1 d . . .
C23 C 0.7412(4) 0.0886(4) 0.8213(3) 0.0469(11) Uani 1 1 d . . .
C24 C 0.6514(3) 0.1585(4) 0.6099(3) 0.0354(9) Uani 1 1 d . . .
H24 H 0.5919 0.1543 0.6746 0.042 Uiso 1 1 calc R . .
C25 C 0.6136(3) 0.2010(4) 0.5010(3) 0.0370(10) Uani 1 1 d . . .
H25 H 0.5268 0.2266 0.4923 0.044 Uiso 1 1 calc R . .
C26 C 0.6977(3) 0.2075(3) 0.4041(3) 0.0312(9) Uani 1 1 d . . .
C27 C 0.6883(3) 0.2947(3) 0.1861(3) 0.0261(8) Uani 1 1 d . . .
C28 C 0.8143(3) 0.3178(3) 0.1391(3) 0.0233(8) Uani 1 1 d . . .
C29 C 0.8443(3) 0.3653(3) 0.0220(3) 0.0283(8) Uani 1 1 d . . .
H29 H 0.9296 0.3795 -0.0083 0.034 Uiso 1 1 calc R . .
C30 C 0.7554(3) 0.3932(3) -0.0532(3) 0.0297(9) Uani 1 1 d . . .
H30 H 0.7790 0.4266 -0.1336 0.036 Uiso 1 1 calc R . .
C31 C 0.6309(3) 0.3714(3) -0.0088(3) 0.0286(8) Uani 1 1 d . . .
H31 H 0.5687 0.3910 -0.0596 0.034 Uiso 1 1 calc R . .
C32 C 0.5960(3) 0.3217(3) 0.1081(3) 0.0247(8) Uani 1 1 d . . .
C33 C 0.4614(3) 0.2960(3) 0.1516(3) 0.0299(9) Uani 1 1 d . . .
C34 C 0.2604(3) 0.2544(4) 0.1162(4) 0.0422(11) Uani 1 1 d . . .
N1 N 0.8946(2) 0.6227(3) 0.2372(2) 0.0266(7) Uani 1 1 d . . .
N2 N 0.6046(3) 0.6256(3) 0.3185(3) 0.0337(8) Uani 1 1 d . . .
N3 N 0.6448(2) 0.2458(3) 0.3012(2) 0.0376(8) Uani 1 1 d . . .
N4 N 0.3941(2) 0.2693(3) 0.0841(3) 0.0342(8) Uani 1 1 d . . .
O1 O 1.2620(2) 0.3203(2) 0.5068(2) 0.0367(7) Uani 1 1 d . . .
O2 O 0.5475(2) 0.7300(3) 0.1427(2) 0.0441(7) Uani 1 1 d . . .
O3 O 0.8265(2) 0.0795(2) 0.7252(2) 0.0370(7) Uani 1 1 d . . .
O4 O 0.4116(2) 0.2988(3) 0.2465(2) 0.0448(7) Uani 1 1 d . . .
H1A H 1.3007 0.1568 0.4639 0.054 Uiso 1 1 d R . .
H1B H 1.3263 0.1356 0.5817 0.054 Uiso 1 1 d R . .
H1C H 1.1816 0.1477 0.5731 0.054 Uiso 1 1 d R . .
H2' H 0.6527 0.6341 0.3718 0.054 Uiso 1 1 d R . .
H3' H 0.5546 0.2668 0.3115 0.054 Uiso 1 1 d R . .
H4' H 0.4339 0.2583 0.0126 0.054 Uiso 1 1 d R . .
H17A H 0.5215 0.5082 0.2881 0.054 Uiso 1 1 d R . .
H17B H 0.5213 0.4596 0.4324 0.054 Uiso 1 1 d R . .
H17C H 0.4287 0.5964 0.3719 0.054 Uiso 1 1 d R . .
H23A H 0.7004 0.1811 0.8099 0.054 Uiso 1 1 d R . .
H23B H 0.7918 0.0392 0.8885 0.054 Uiso 1 1 d R . .
H23C H 0.6675 0.0225 0.8343 0.054 Uiso 1 1 d R . .
H34A H 0.2462 0.1771 0.1914 0.054 Uiso 1 1 d R . .
H34B H 0.2300 0.2164 0.0659 0.054 Uiso 1 1 d R . .
H34C H 0.2118 0.3331 0.1266 0.054 Uiso 1 1 d 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 O1 1.422(4) . ?
C1 H1A 1.0103 . ?
C1 H1B 0.9131 . ?
C1 H1C 1.0531 . ?
C2 C7 1.376(5) . ?
C2 O1 1.391(4) . ?
C2 C3 1.396(5) . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.396(4) . ?
C5 C6 1.405(4) . ?
C6 C7 1.417(4) . ?
C6 C8 1.445(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.360(4) . ?
C8 C18 1.510(4) . ?
C9 N1 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(4) . ?
C10 C15 1.407(4) . ?
C10 N1 1.414(4) . ?
C11 C12 1.376(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.494(5) . ?
C16 O2 1.237(4) . ?
C16 N2 1.317(4) . ?
C17 N2 1.464(5) . ?
C17 H17A 0.9256 . ?
C17 H17B 1.0673 . ?
C17 H17C 1.0867 . ?
C18 C28 1.527(4) . ?
C18 C19 1.552(5) . ?
C18 H18 1.0000 . ?
C19 C20 1.491(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.394(5) . ?
C20 C26 1.404(4) . ?
C21 C22 1.380(5) . ?
C21 H21 0.9500 . ?
C22 C24 1.377(5) . ?
C22 O3 1.382(4) . ?
C23 O3 1.434(4) . ?
C23 H23A 1.0224 . ?
C23 H23B 1.0167 . ?
C23 H23C 1.1078 . ?
C24 C25 1.389(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.393(5) . ?
C25 H25 0.9500 . ?
C26 N3 1.400(4) . ?
C27 N3 1.380(4) . ?
C27 C28 1.412(4) . ?
C27 C32 1.437(4) . ?
C28 C29 1.378(5) . ?
C29 C30 1.380(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.496(4) . ?
C33 O4 1.249(4) . ?
C33 N4 1.339(4) . ?
C34 N4 1.451(4) . ?
C34 H34A 1.0210 . ?
C34 H34B 0.9993 . ?
C34 H34C 0.9937 . ?
N2 H2' 0.9527 . ?
N3 H3' 0.9685 . ?
N4 H4' 0.9840 . ?

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
O1 C1 H1A 113.8 . . ?
O1 C1 H1B 113.8 . . ?
H1A C1 H1B 101.2 . . ?
O1 C1 H1C 109.6 . . ?
H1A C1 H1C 112.7 . . ?
H1B C1 H1C 105.3 . . ?
C7 C2 O1 123.6(3) . . ?
C7 C2 C3 121.5(3) . . ?
O1 C2 C3 114.8(3) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.0(3) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
N1 C5 C4 130.7(3) . . ?
N1 C5 C6 107.5(3) . . ?
C4 C5 C6 121.8(3) . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 C8 107.8(3) . . ?
C7 C6 C8 133.1(3) . . ?
C2 C7 C6 118.7(3) . . ?
C2 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C9 C8 C6 105.8(3) . . ?
C9 C8 C18 125.5(3) . . ?
C6 C8 C18 128.5(3) . . ?
C8 C9 N1 111.3(3) . . ?
C8 C9 H9 124.3 . . ?
N1 C9 H9 124.3 . . ?
C11 C10 C15 119.0(3) . . ?
C11 C10 N1 118.7(3) . . ?
C15 C10 N1 122.1(3) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.1(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 121.6(3) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C10 118.8(3) . . ?
C14 C15 C16 116.1(3) . . ?
C10 C15 C16 125.1(3) . . ?
O2 C16 N2 121.8(3) . . ?
O2 C16 C15 119.5(3) . . ?
N2 C16 C15 118.7(3) . . ?
N2 C17 H17A 99.7 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 117.2 . . ?
N2 C17 H17C 98.0 . . ?
H17A C17 H17C 127.3 . . ?
H17B C17 H17C 102.4 . . ?
C8 C18 C28 111.0(3) . . ?
C8 C18 C19 114.0(3) . . ?
C28 C18 C19 113.2(3) . . ?
C8 C18 H18 106.0 . . ?
C28 C18 H18 106.0 . . ?
C19 C18 H18 106.0 . . ?
C20 C19 C18 115.2(3) . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C26 118.0(3) . . ?
C21 C20 C19 121.5(3) . . ?
C26 C20 C19 120.5(3) . . ?
C22 C21 C20 122.3(3) . . ?
C22 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
C24 C22 C21 120.1(3) . . ?
C24 C22 O3 123.6(3) . . ?
C21 C22 O3 116.4(3) . . ?
O3 C23 H23A 113.9 . . ?
O3 C23 H23B 102.9 . . ?
H23A C23 H23B 120.2 . . ?
O3 C23 H23C 105.9 . . ?
H23A C23 H23C 109.7 . . ?
H23B C23 H23C 102.8 . . ?
C22 C24 C25 118.3(4) . . ?
C22 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
C26 C25 C24 122.6(3) . . ?
C26 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C25 C26 N3 116.1(3) . . ?
C25 C26 C20 118.6(3) . . ?
N3 C26 C20 125.1(3) . . ?
N3 C27 C28 126.1(3) . . ?
N3 C27 C32 116.1(3) . . ?
C28 C27 C32 117.8(3) . . ?
C29 C28 C27 119.7(3) . . ?
C29 C28 C18 117.4(3) . . ?
C27 C28 C18 122.9(3) . . ?
C30 C29 C28 122.7(3) . . ?
C30 C29 H29 118.7 . . ?
C28 C29 H29 118.7 . . ?
C29 C30 C31 118.6(3) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C32 C31 C30 121.1(3) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C31 C32 C27 120.2(3) . . ?
C31 C32 C33 119.1(3) . . ?
C27 C32 C33 120.8(3) . . ?
O4 C33 N4 120.1(3) . . ?
O4 C33 C32 122.6(3) . . ?
N4 C33 C32 117.2(3) . . ?
N4 C34 H34A 110.2 . . ?
N4 C34 H34B 109.1 . . ?
H34A C34 H34B 97.3 . . ?
N4 C34 H34C 113.0 . . ?
H34A C34 H34C 107.5 . . ?
H34B C34 H34C 118.5 . . ?
C9 N1 C5 107.5(3) . . ?
C9 N1 C10 125.0(3) . . ?
C5 N1 C10 126.8(3) . . ?
C16 N2 C17 120.9(3) . . ?
C16 N2 H2' 115.0 . . ?
C17 N2 H2' 123.6 . . ?
C27 N3 C26 135.9(3) . . ?
C27 N3 H3' 109.6 . . ?
C26 N3 H3' 111.7 . . ?
C33 N4 C34 120.3(3) . . ?
C33 N4 H4' 121.2 . . ?
C34 N4 H4' 118.5 . . ?
C2 O1 C1 115.7(3) . . ?
C22 O3 C23 116.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.082
_database_code_depnum_ccdc_archive 'CCDC 1003565'
#######################################################################
#
#                 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_a16134

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 Cl2 N2'
_chemical_formula_sum            'C28 H20 Cl2 N2'
_chemical_formula_weight         455.36

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'
Cl Cl 0.1484 0.1585 '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/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                   7.242(6)
_cell_length_b                   21.438(12)
_cell_length_c                   14.019(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.92(3)
_cell_angle_gamma                90.00
_cell_volume                     2161(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8537
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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            10614
_diffrn_reflns_av_R_equivalents  0.2401
_diffrn_reflns_av_sigmaI/netI    0.4358
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.30
_reflns_number_total             3907
_reflns_number_gt                1112
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0949P)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         3907
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3364
_refine_ls_R_factor_gt           0.1027
_refine_ls_wR_factor_ref         0.2902
_refine_ls_wR_factor_gt          0.1930
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.001
_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 0.1431(14) 0.8821(5) 0.9707(8) 0.039(3) Uani 1 1 d . . .
C2 C 0.2863(12) 0.9222(5) 0.9670(7) 0.034(3) Uani 1 1 d . . .
H2 H 0.2814 0.9634 0.9917 0.041 Uiso 1 1 calc R . .
C3 C 0.4410(14) 0.9015(5) 0.9261(8) 0.043(3) Uani 1 1 d . . .
H3 H 0.5413 0.9295 0.9216 0.052 Uiso 1 1 calc R . .
C4 C 0.4527(12) 0.8409(5) 0.8917(7) 0.027(3) Uani 1 1 d . . .
C5 C 0.3077(13) 0.8003(5) 0.8964(7) 0.032(3) Uani 1 1 d . . .
C6 C 0.1504(11) 0.8226(5) 0.9382(7) 0.039(3) Uani 1 1 d . . .
H6 H 0.0487 0.7954 0.9435 0.047 Uiso 1 1 calc R . .
C7 C 0.3225(15) 0.7317(5) 0.8608(9) 0.063(4) Uani 1 1 d . . .
H7 H 0.4414 0.7167 0.8972 0.075 Uiso 1 1 calc R . .
C8 C 0.3521(17) 0.7231(6) 0.7633(9) 0.083(5) Uani 1 1 d . . .
H8A H 0.2483 0.7440 0.7232 0.100 Uiso 1 1 calc R . .
H8B H 0.3404 0.6779 0.7495 0.100 Uiso 1 1 calc R . .
C9 C 0.5311(12) 0.7450(5) 0.7285(8) 0.031(3) Uani 1 1 d . . .
C10 C 0.6465(12) 0.7928(5) 0.7682(7) 0.024(3) Uani 1 1 d . . .
C11 C 0.7970(12) 0.8119(5) 0.7236(8) 0.041(3) Uani 1 1 d . . .
H11 H 0.8733 0.8455 0.7488 0.049 Uiso 1 1 calc R . .
C12 C 0.8350(14) 0.7801(5) 0.6397(9) 0.045(3) Uani 1 1 d . . .
H12 H 0.9420 0.7915 0.6107 0.054 Uiso 1 1 calc R . .
C13 C 0.7217(13) 0.7328(5) 0.5980(8) 0.038(3) Uani 1 1 d . . .
H13 H 0.7457 0.7136 0.5397 0.045 Uiso 1 1 calc R . .
C14 C 0.5725(12) 0.7147(5) 0.6445(8) 0.039(3) Uani 1 1 d . . .
H14 H 0.4963 0.6810 0.6193 0.047 Uiso 1 1 calc R . .
C15 C 0.1754(14) 0.6869(5) 0.8939(9) 0.042(3) Uani 1 1 d . . .
C16 C 0.1970(14) 0.6543(5) 0.9852(10) 0.040(3) Uani 1 1 d . . .
C17 C 0.3261(14) 0.6489(6) 1.0673(10) 0.050(4) Uani 1 1 d . . .
H17 H 0.4364 0.6733 1.0727 0.060 Uiso 1 1 calc R . .
C18 C 0.2962(16) 0.6089(5) 1.1401(9) 0.049(4) Uani 1 1 d . . .
H18 H 0.3850 0.6069 1.1957 0.059 Uiso 1 1 calc R . .
C19 C 0.1415(15) 0.5718(5) 1.1348(9) 0.047(3) Uani 1 1 d . . .
H19 H 0.1249 0.5445 1.1865 0.056 Uiso 1 1 calc R . .
C20 C 0.0096(15) 0.5735(5) 1.0554(9) 0.041(3) Uani 1 1 d . . .
H20 H -0.0967 0.5473 1.0524 0.049 Uiso 1 1 calc R . .
C21 C 0.0317(15) 0.6142(5) 0.9785(9) 0.037(3) Uani 1 1 d . . .
C22 C 0.0137(14) 0.6691(5) 0.8399(8) 0.036(3) Uani 1 1 d . . .
H22 H -0.0297 0.6847 0.7778 0.043 Uiso 1 1 calc R . .
C23 C -0.2453(11) 0.5930(5) 0.8492(9) 0.036(3) Uani 1 1 d . . .
C24 C -0.3783(12) 0.5808(5) 0.9113(8) 0.034(3) Uani 1 1 d . . .
H24 H -0.3614 0.5925 0.9771 0.041 Uiso 1 1 calc R . .
C25 C -0.5409(13) 0.5494(5) 0.8685(9) 0.042(2) Uani 1 1 d . . .
H25 H -0.6341 0.5385 0.9077 0.051 Uiso 1 1 calc R . .
C26 C -0.5675(13) 0.5345(5) 0.7730(9) 0.039(3) Uani 1 1 d . . .
C27 C -0.4342(13) 0.5476(5) 0.7143(9) 0.042(2) Uani 1 1 d . . .
H27 H -0.4540 0.5368 0.6481 0.051 Uiso 1 1 calc R . .
C28 C -0.2733(15) 0.5760(5) 0.7513(8) 0.044(3) Uani 1 1 d . . .
H28 H -0.1796 0.5844 0.7112 0.053 Uiso 1 1 calc R . .
N1 N 0.6176(9) 0.8253(4) 0.8530(6) 0.030(2) Uani 1 1 d . . .
H1 H 0.7202 0.8380 0.8876 0.035 Uiso 1 1 calc R . .
N2 N -0.0778(11) 0.6246(4) 0.8901(7) 0.036(3) Uani 1 1 d . . .
Cl1 Cl -0.0561(3) 0.90523(14) 1.0186(2) 0.0505(10) Uani 1 1 d . . .
Cl2 Cl -0.7703(4) 0.49766(16) 0.7282(3) 0.0679(12) 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
C1 C2 1.352(12) . ?
C1 C6 1.357(13) . ?
C1 Cl1 1.736(10) . ?
C2 C3 1.392(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(12) . ?
C4 N1 1.409(10) . ?
C5 C6 1.425(12) . ?
C5 C7 1.561(14) . ?
C6 H6 0.9500 . ?
C7 C8 1.420(14) . ?
C7 C15 1.546(13) . ?
C7 H7 1.0000 . ?
C8 C9 1.514(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.394(13) . ?
C9 C14 1.408(13) . ?
C10 C11 1.382(12) . ?
C10 N1 1.416(11) . ?
C11 C12 1.416(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(12) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C22 1.369(13) . ?
C15 C16 1.451(15) . ?
C16 C17 1.397(15) . ?
C16 C21 1.468(13) . ?
C17 C18 1.371(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(14) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(14) . ?
C19 H19 0.9500 . ?
C20 C21 1.410(15) . ?
C20 H20 0.9500 . ?
C21 N2 1.406(13) . ?
C22 N2 1.398(11) . ?
C22 H22 0.9500 . ?
C23 C24 1.399(12) . ?
C23 C28 1.410(14) . ?
C23 N2 1.447(12) . ?
C24 C25 1.424(13) . ?
C24 H24 0.9500 . ?
C25 C26 1.367(14) . ?
C25 H25 0.9500 . ?
C26 C27 1.371(13) . ?
C26 Cl2 1.719(10) . ?
C27 C28 1.362(13) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N1 H1 0.8800 . ?

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
C2 C1 C6 121.6(9) . . ?
C2 C1 Cl1 120.7(8) . . ?
C6 C1 Cl1 117.8(8) . . ?
C1 C2 C3 118.1(10) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 121.8(9) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 119.7(9) . . ?
C5 C4 N1 123.9(10) . . ?
C3 C4 N1 116.4(8) . . ?
C4 C5 C6 117.5(10) . . ?
C4 C5 C7 120.0(8) . . ?
C6 C5 C7 122.5(9) . . ?
C1 C6 C5 121.3(9) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C15 113.4(10) . . ?
C8 C7 C5 117.0(10) . . ?
C15 C7 C5 114.4(8) . . ?
C8 C7 H7 103.2 . . ?
C15 C7 H7 103.2 . . ?
C5 C7 H7 103.2 . . ?
C7 C8 C9 120.3(11) . . ?
C7 C8 H8A 107.2 . . ?
C9 C8 H8A 107.2 . . ?
C7 C8 H8B 107.2 . . ?
C9 C8 H8B 107.2 . . ?
H8A C8 H8B 106.9 . . ?
C10 C9 C14 119.7(9) . . ?
C10 C9 C8 126.4(10) . . ?
C14 C9 C8 113.8(10) . . ?
C11 C10 C9 120.3(10) . . ?
C11 C10 N1 116.0(10) . . ?
C9 C10 N1 123.7(9) . . ?
C10 C11 C12 118.4(11) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 122.5(10) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C14 C13 C12 117.5(10) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C13 C14 C9 121.4(11) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C22 C15 C16 110.3(10) . . ?
C22 C15 C7 125.5(12) . . ?
C16 C15 C7 124.0(11) . . ?
C17 C16 C15 139.2(11) . . ?
C17 C16 C21 117.6(12) . . ?
C15 C16 C21 103.0(11) . . ?
C18 C17 C16 121.0(11) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 121.7(12) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C20 120.7(12) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C21 120.2(10) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
N2 C21 C20 131.9(11) . . ?
N2 C21 C16 109.4(10) . . ?
C20 C21 C16 118.7(12) . . ?
C15 C22 N2 109.7(10) . . ?
C15 C22 H22 125.1 . . ?
N2 C22 H22 125.1 . . ?
C24 C23 C28 121.9(10) . . ?
C24 C23 N2 116.6(11) . . ?
C28 C23 N2 121.5(9) . . ?
C23 C24 C25 115.0(10) . . ?
C23 C24 H24 122.5 . . ?
C25 C24 H24 122.5 . . ?
C26 C25 C24 122.3(10) . . ?
C26 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
C25 C26 C27 120.9(10) . . ?
C25 C26 Cl2 118.6(8) . . ?
C27 C26 Cl2 120.4(10) . . ?
C26 C27 C28 119.6(11) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C27 C28 C23 120.2(10) . . ?
C27 C28 H28 119.9 . . ?
C23 C28 H28 119.9 . . ?
C4 N1 C10 131.1(8) . . ?
C4 N1 H1 114.4 . . ?
C10 N1 H1 114.4 . . ?
C22 N2 C21 107.5(9) . . ?
C22 N2 C23 123.1(10) . . ?
C21 N2 C23 129.2(9) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.30
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.086
_database_code_depnum_ccdc_archive 'CCDC 1003566'
