# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 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_c460
_database_code_depnum_ccdc_archive 'CCDC 919643'
#TrackingRef '16894_web_deposit_cif_file_0_WeiLekKwan_1358264482.SQ2.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H44 N6 O2'
_chemical_formula_weight         712.87
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                   10.136(2)
_cell_length_b                   10.200(2)
_cell_length_c                   10.494(2)
_cell_angle_alpha                61.219(4)
_cell_angle_beta                 74.534(5)
_cell_angle_gamma                80.977(5)
_cell_volume                     915.9(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    802
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.24
_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             378
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6608
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9032
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4174
_reflns_number_gt                3194
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0745P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         4174
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
O1 O -0.06504(9) 1.17990(9) 0.07458(10) 0.0205(2) Uani 1 1 d . . .
N1 N 0.31493(11) 0.86738(11) 0.09926(11) 0.0155(2) Uani 1 1 d . . .
N2 N 0.60133(11) 0.82223(11) 0.26160(12) 0.0182(3) Uani 1 1 d . . .
N3 N 0.71264(11) 0.73237(11) 0.30100(12) 0.0190(3) Uani 1 1 d . . .
C1 C -0.03139(13) 1.08253(13) 0.03427(14) 0.0156(3) Uani 1 1 d . . .
C2 C 0.09045(13) 0.98198(13) 0.03674(13) 0.0154(3) Uani 1 1 d . . .
C3 C 0.20516(13) 0.96936(13) 0.09171(14) 0.0160(3) Uani 1 1 d . . .
C4 C 0.23088(14) 1.05648(14) 0.15399(14) 0.0178(3) Uani 1 1 d . . .
H4 H 0.1732 1.1353 0.1643 0.021 Uiso 1 1 calc R . .
C5 C 0.35368(13) 1.00720(14) 0.19695(14) 0.0185(3) Uani 1 1 d . . .
H5 H 0.3966 1.0470 0.2405 0.022 Uiso 1 1 calc R . .
C6 C 0.40440(13) 0.88714(14) 0.16491(14) 0.0169(3) Uani 1 1 d . . .
C7 C 0.52398(13) 0.79139(14) 0.19974(14) 0.0170(3) Uani 1 1 d . . .
H7 H 0.5452 0.7091 0.1782 0.020 Uiso 1 1 calc R . .
C8 C 0.32431(13) 0.74643(13) 0.05927(14) 0.0168(3) Uani 1 1 d . . .
H8A H 0.4219 0.7176 0.0335 0.020 Uiso 1 1 calc R . .
H8B H 0.2859 0.7830 -0.0299 0.020 Uiso 1 1 calc R . .
C9 C 0.24751(14) 0.60901(14) 0.18590(15) 0.0208(3) Uani 1 1 d . . .
H9A H 0.2638 0.5923 0.2816 0.025 Uiso 1 1 calc R . .
H9B H 0.1480 0.6286 0.1901 0.025 Uiso 1 1 calc R . .
C10 C 0.29107(15) 0.46757(14) 0.16791(16) 0.0251(3) Uani 1 1 d . . .
H10A H 0.2199 0.3922 0.2317 0.030 Uiso 1 1 calc R . .
H10B H 0.2977 0.4917 0.0631 0.030 Uiso 1 1 calc R . .
C11 C 0.42784(16) 0.40065(15) 0.20920(17) 0.0293(3) Uani 1 1 d . . .
H11A H 0.4992 0.4738 0.1447 0.044 Uiso 1 1 calc R . .
H11B H 0.4509 0.3103 0.1960 0.044 Uiso 1 1 calc R . .
H11C H 0.4215 0.3747 0.3135 0.044 Uiso 1 1 calc R . .
C12 C 0.73567(13) 0.59127(13) 0.29599(14) 0.0166(3) Uani 1 1 d . . .
C13 C 0.67119(13) 0.46553(14) 0.41693(14) 0.0188(3) Uani 1 1 d . . .
H13 H 0.6158 0.4725 0.5023 0.023 Uiso 1 1 calc R . .
C14 C 0.68802(14) 0.33006(14) 0.41256(15) 0.0202(3) Uani 1 1 d . . .
H14 H 0.6432 0.2443 0.4943 0.024 Uiso 1 1 calc R . .
C15 C 0.77046(14) 0.32008(14) 0.28862(15) 0.0203(3) Uani 1 1 d . . .
H15 H 0.7814 0.2277 0.2848 0.024 Uiso 1 1 calc R . .
C16 C 0.83689(14) 0.44507(14) 0.17031(15) 0.0209(3) Uani 1 1 d . . .
H16 H 0.8951 0.4373 0.0866 0.025 Uiso 1 1 calc R . .
C17 C 0.81933(13) 0.58137(14) 0.17290(14) 0.0193(3) Uani 1 1 d . . .
H17 H 0.8643 0.6670 0.0910 0.023 Uiso 1 1 calc R . .
C18 C 0.78865(13) 0.76777(13) 0.37436(14) 0.0165(3) Uani 1 1 d . . .
C19 C 0.91058(13) 0.68758(14) 0.40626(15) 0.0204(3) Uani 1 1 d . . .
H19 H 0.9414 0.6099 0.3788 0.025 Uiso 1 1 calc R . .
C20 C 0.98666(14) 0.72120(15) 0.47801(16) 0.0235(3) Uani 1 1 d . . .
H20 H 1.0700 0.6668 0.4984 0.028 Uiso 1 1 calc R . .
C21 C 0.94299(14) 0.83284(14) 0.52032(15) 0.0225(3) Uani 1 1 d . . .
H21 H 0.9949 0.8546 0.5706 0.027 Uiso 1 1 calc R . .
C22 C 0.82194(14) 0.91234(14) 0.48800(15) 0.0213(3) Uani 1 1 d . . .
H22 H 0.7912 0.9893 0.5164 0.026 Uiso 1 1 calc R . .
C23 C 0.74499(14) 0.88161(14) 0.41505(15) 0.0197(3) Uani 1 1 d . . .
H23 H 0.6628 0.9379 0.3929 0.024 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0188(5) 0.0216(5) 0.0291(5) -0.0179(4) -0.0088(4) 0.0060(4)
N1 0.0134(5) 0.0170(5) 0.0188(5) -0.0105(4) -0.0057(4) 0.0035(4)
N2 0.0141(6) 0.0196(5) 0.0228(6) -0.0113(5) -0.0076(4) 0.0051(4)
N3 0.0165(6) 0.0193(5) 0.0289(6) -0.0163(5) -0.0118(5) 0.0080(4)
C1 0.0140(6) 0.0170(6) 0.0162(6) -0.0083(5) -0.0033(5) 0.0009(5)
C2 0.0150(6) 0.0146(6) 0.0162(6) -0.0076(5) -0.0034(5) 0.0023(5)
C3 0.0143(6) 0.0157(6) 0.0179(6) -0.0084(5) -0.0040(5) 0.0027(5)
C4 0.0181(7) 0.0166(6) 0.0212(7) -0.0112(5) -0.0060(5) 0.0038(5)
C5 0.0185(7) 0.0196(6) 0.0221(7) -0.0124(5) -0.0074(5) 0.0017(5)
C6 0.0157(7) 0.0175(6) 0.0179(6) -0.0088(5) -0.0043(5) 0.0009(5)
C7 0.0158(7) 0.0176(6) 0.0200(7) -0.0108(5) -0.0059(5) 0.0036(5)
C8 0.0162(6) 0.0188(6) 0.0207(7) -0.0132(5) -0.0062(5) 0.0034(5)
C9 0.0180(7) 0.0212(6) 0.0240(7) -0.0124(6) -0.0032(5) 0.0013(5)
C10 0.0276(8) 0.0206(7) 0.0302(8) -0.0144(6) -0.0049(6) -0.0024(6)
C11 0.0324(9) 0.0212(7) 0.0319(8) -0.0127(6) -0.0064(7) 0.0061(6)
C12 0.0134(6) 0.0190(6) 0.0247(7) -0.0140(5) -0.0113(5) 0.0060(5)
C13 0.0153(6) 0.0262(7) 0.0192(7) -0.0140(6) -0.0067(5) 0.0047(5)
C14 0.0187(7) 0.0190(6) 0.0223(7) -0.0081(5) -0.0074(5) 0.0012(5)
C15 0.0219(7) 0.0186(6) 0.0266(7) -0.0136(6) -0.0123(6) 0.0057(5)
C16 0.0177(7) 0.0267(7) 0.0229(7) -0.0158(6) -0.0059(5) 0.0038(5)
C17 0.0164(7) 0.0214(6) 0.0210(7) -0.0100(5) -0.0058(5) 0.0004(5)
C18 0.0150(6) 0.0173(6) 0.0193(6) -0.0092(5) -0.0057(5) 0.0004(5)
C19 0.0175(7) 0.0207(6) 0.0294(7) -0.0163(6) -0.0086(6) 0.0050(5)
C20 0.0173(7) 0.0243(7) 0.0333(8) -0.0150(6) -0.0122(6) 0.0049(5)
C21 0.0228(7) 0.0225(7) 0.0274(7) -0.0123(6) -0.0112(6) -0.0023(5)
C22 0.0247(7) 0.0169(6) 0.0265(7) -0.0124(6) -0.0088(6) 0.0016(5)
C23 0.0176(7) 0.0180(6) 0.0255(7) -0.0116(5) -0.0078(5) 0.0042(5)
_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
O1 C1 1.2259(15) . ?
N1 C6 1.3645(16) . ?
N1 C3 1.3895(16) . ?
N1 C8 1.4654(15) . ?
N2 C7 1.2963(17) . ?
N2 N3 1.3578(15) . ?
N3 C18 1.4099(16) . ?
N3 C12 1.4454(15) . ?
C1 C2 1.4737(17) . ?
C1 C2 1.4765(17) 2_575 ?
C2 C3 1.3930(18) . ?
C2 C1 1.4765(17) 2_575 ?
C3 C4 1.4169(17) . ?
C4 C5 1.3748(19) . ?
C5 C6 1.4085(18) . ?
C6 C7 1.4414(18) . ?
C8 C9 1.5275(17) . ?
C9 C10 1.5264(18) . ?
C10 C11 1.521(2) . ?
C12 C17 1.3828(18) . ?
C12 C13 1.3914(18) . ?
C13 C14 1.3868(18) . ?
C14 C15 1.3861(19) . ?
C15 C16 1.3854(18) . ?
C16 C17 1.3862(18) . ?
C18 C23 1.3936(17) . ?
C18 C19 1.3958(18) . ?
C19 C20 1.3858(18) . ?
C20 C21 1.3833(19) . ?
C21 C22 1.3867(19) . ?
C22 C23 1.3852(18) . ?
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
C6 N1 C3 109.32(10) . . ?
C6 N1 C8 125.39(11) . . ?
C3 N1 C8 124.92(11) . . ?
C7 N2 N3 119.46(11) . . ?
N2 N3 C18 116.64(10) . . ?
N2 N3 C12 121.28(10) . . ?
C18 N3 C12 120.90(10) . . ?
O1 C1 C2 133.40(12) . . ?
O1 C1 C2 136.48(12) . 2_575 ?
C2 C1 C2 90.12(10) . 2_575 ?
C3 C2 C1 128.65(12) . . ?
C3 C2 C1 141.46(12) . 2_575 ?
C1 C2 C1 89.88(10) . 2_575 ?
N1 C3 C2 126.92(11) . . ?
N1 C3 C4 106.65(11) . . ?
C2 C3 C4 126.41(12) . . ?
C5 C4 C3 108.20(11) . . ?
C4 C5 C6 107.74(11) . . ?
N1 C6 C5 108.07(11) . . ?
N1 C6 C7 123.17(11) . . ?
C5 C6 C7 128.67(12) . . ?
N2 C7 C6 117.28(11) . . ?
N1 C8 C9 112.09(10) . . ?
C10 C9 C8 112.89(11) . . ?
C11 C10 C9 112.71(12) . . ?
C17 C12 C13 120.49(11) . . ?
C17 C12 N3 120.73(11) . . ?
C13 C12 N3 118.78(12) . . ?
C14 C13 C12 119.82(12) . . ?
C15 C14 C13 119.86(12) . . ?
C16 C15 C14 119.87(12) . . ?
C15 C16 C17 120.66(12) . . ?
C12 C17 C16 119.27(12) . . ?
C23 C18 C19 119.29(12) . . ?
C23 C18 N3 121.41(11) . . ?
C19 C18 N3 119.30(11) . . ?
C20 C19 C18 120.02(12) . . ?
C21 C20 C19 120.95(13) . . ?
C20 C21 C22 118.74(12) . . ?
C23 C22 C21 121.27(12) . . ?
C22 C23 C18 119.71(12) . . ?
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052


data_c499
_database_code_depnum_ccdc_archive 'CCDC 919644'
#TrackingRef '16895_web_deposit_cif_file_1_WeiLekKwan_1358264482.SQ-P2.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H48 N6 O2'
_chemical_formula_weight         837.00
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                   10.125(9)
_cell_length_b                   10.347(9)
_cell_length_c                   11.204(9)
_cell_angle_alpha                104.475(15)
_cell_angle_beta                 94.514(17)
_cell_angle_gamma                104.237(16)
_cell_volume                     1089.2(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    419
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      21.58
_exptl_crystal_description       Rod
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'Not measured'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             442
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6416
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_sigmaI/netI    0.1978
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4817
_reflns_number_gt                2435
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1852P)^2^+0.7391P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.036(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         4817
_refine_ls_number_parameters     290
_refine_ls_number_restraints     192
_refine_ls_R_factor_all          0.2305
_refine_ls_R_factor_gt           0.1413
_refine_ls_wR_factor_ref         0.3628
_refine_ls_wR_factor_gt          0.3114
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.041
_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
O1 O 1.0609(4) 0.7124(4) 0.9676(4) 0.0173(9) Uani 1 1 d U . .
N1 N 0.6436(5) 0.3902(4) 0.9130(4) 0.0129(10) Uani 1 1 d U . .
N2 N 0.3036(5) 0.3770(5) 0.7804(4) 0.0156(11) Uani 1 1 d U . .
N3 N 0.1760(5) 0.2855(5) 0.7461(4) 0.0180(11) Uani 1 1 d U . .
C1 C 1.0291(6) 0.5958(5) 0.9854(5) 0.0114(11) Uani 1 1 d U . .
C2 C 0.8973(6) 0.4918(5) 0.9698(5) 0.0113(11) Uani 1 1 d U . .
C3 C 0.7659(6) 0.4925(5) 0.9249(5) 0.0103(11) Uani 1 1 d U . .
C4 C 0.7319(6) 0.5937(6) 0.8747(5) 0.0138(12) Uani 1 1 d U . .
H4 H 0.7949 0.6764 0.8699 0.017 Uiso 1 1 calc R . .
C5 C 0.5930(6) 0.5537(6) 0.8337(5) 0.0149(12) Uani 1 1 d U . .
H5 H 0.5429 0.6032 0.7958 0.018 Uiso 1 1 calc R . .
C6 C 0.5383(6) 0.4259(5) 0.8582(5) 0.0127(12) Uani 1 1 d U . .
C7 C 0.4015(6) 0.3366(6) 0.8271(5) 0.0174(12) Uani 1 1 d U . .
H7 H 0.3824 0.2473 0.8408 0.021 Uiso 1 1 calc R . .
C8 C 0.6299(6) 0.2600(5) 0.9467(5) 0.0147(12) Uani 1 1 d U . .
H8A H 0.5423 0.2352 0.9800 0.018 Uiso 1 1 calc R . .
H8B H 0.7067 0.2720 1.0125 0.018 Uiso 1 1 calc R . .
C9 C 0.6319(6) 0.1446(6) 0.8338(5) 0.0190(13) Uani 1 1 d U . .
H9A H 0.7242 0.1650 0.8076 0.023 Uiso 1 1 calc R . .
H9B H 0.5640 0.1429 0.7644 0.023 Uiso 1 1 calc R . .
C10 C 0.5989(7) 0.0005(6) 0.8566(6) 0.0227(14) Uani 1 1 d U . .
H10A H 0.6593 0.0043 0.9321 0.027 Uiso 1 1 calc R . .
H10B H 0.5022 -0.0260 0.8717 0.027 Uiso 1 1 calc R . .
C11 C 0.6191(6) -0.1064(6) 0.7487(5) 0.0189(13) Uani 1 1 d U . .
C12 C 0.7497(7) -0.1175(6) 0.7287(6) 0.0243(14) Uani 1 1 d U . .
H12 H 0.8268 -0.0578 0.7875 0.029 Uiso 1 1 calc R . .
C13 C 0.7720(7) -0.2114(6) 0.6274(6) 0.0237(14) Uani 1 1 d U . .
H13 H 0.8627 -0.2177 0.6174 0.028 Uiso 1 1 calc R . .
C14 C 0.6621(7) -0.2957(7) 0.5410(6) 0.0279(15) Uani 1 1 d U . .
H14 H 0.6760 -0.3599 0.4694 0.033 Uiso 1 1 calc R . .
C15 C 0.5310(8) -0.2870(8) 0.5582(7) 0.0408(19) Uani 1 1 d U . .
H15 H 0.4546 -0.3458 0.4983 0.049 Uiso 1 1 calc R . .
C16 C 0.5098(8) -0.1945(7) 0.6607(6) 0.0324(16) Uani 1 1 d U . .
H16 H 0.4185 -0.1908 0.6716 0.039 Uiso 1 1 calc R . .
C17 C 0.1558(6) 0.1456(6) 0.7562(5) 0.0180(13) Uani 1 1 d U . .
C18 C 0.1811(7) 0.0481(6) 0.6586(6) 0.0224(14) Uani 1 1 d U . .
H18 H 0.2033 0.0704 0.5840 0.027 Uiso 1 1 calc R . .
C19 C 0.1731(7) -0.0843(6) 0.6718(6) 0.0244(14) Uani 1 1 d U . .
H19 H 0.1881 -0.1538 0.6051 0.029 Uiso 1 1 calc R . .
C20 C 0.1436(6) -0.1139(6) 0.7816(5) 0.0199(13) Uani 1 1 d U . .
H20 H 0.1422 -0.2025 0.7920 0.024 Uiso 1 1 calc R . .
C21 C 0.1163(6) -0.0158(6) 0.8756(5) 0.0165(12) Uani 1 1 d U . .
H21 H 0.0937 -0.0378 0.9502 0.020 Uiso 1 1 calc R . .
C22 C 0.1210(6) 0.1141(6) 0.8637(5) 0.0159(12) Uani 1 1 d U . .
H22 H 0.1004 0.1814 0.9289 0.019 Uiso 1 1 calc R . .
C23 C 0.0679(6) 0.3321(6) 0.7016(5) 0.0166(12) Uani 1 1 d U . .
C24 C -0.0649(6) 0.2455(6) 0.6679(5) 0.0185(13) Uani 1 1 d U . .
H24 H -0.0829 0.1526 0.6730 0.022 Uiso 1 1 calc R . .
C25 C -0.1711(7) 0.2923(6) 0.6272(5) 0.0223(14) Uani 1 1 d U . .
H25 H -0.2619 0.2316 0.6056 0.027 Uiso 1 1 calc R . .
C26 C -0.1482(7) 0.4246(7) 0.6172(6) 0.0266(15) Uani 1 1 d U . .
H26 H -0.2221 0.4568 0.5897 0.032 Uiso 1 1 calc R . .
C27 C -0.0170(7) 0.5096(7) 0.6474(6) 0.0276(15) Uani 1 1 d U . .
H27 H 0.0001 0.6013 0.6394 0.033 Uiso 1 1 calc R . .
C28 C 0.0919(7) 0.4659(6) 0.6895(6) 0.0243(14) Uani 1 1 d U . .
H28 H 0.1825 0.5270 0.7100 0.029 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0187(17) 0.0079(15) 0.0245(16) 0.0075(13) -0.0004(13) 0.0007(13)
N1 0.0138(18) 0.0068(17) 0.0167(17) 0.0042(14) -0.0018(14) 0.0010(14)
N2 0.0143(18) 0.0116(17) 0.0189(17) 0.0061(14) -0.0023(14) -0.0007(14)
N3 0.0178(19) 0.0121(18) 0.0227(18) 0.0078(14) -0.0018(15) 0.0001(14)
C1 0.0125(19) 0.0051(18) 0.0151(18) 0.0025(14) -0.0002(15) 0.0007(14)
C2 0.0118(19) 0.0075(18) 0.0126(18) 0.0040(15) -0.0018(15) -0.0013(15)
C3 0.0114(19) 0.0056(18) 0.0120(18) 0.0028(14) -0.0032(15) -0.0002(14)
C4 0.015(2) 0.0089(18) 0.0163(18) 0.0043(15) -0.0002(15) 0.0010(15)
C5 0.016(2) 0.0088(18) 0.0198(19) 0.0055(15) -0.0011(15) 0.0030(15)
C6 0.0141(19) 0.0084(18) 0.0159(18) 0.0056(15) -0.0013(15) 0.0024(15)
C7 0.018(2) 0.0133(19) 0.0209(19) 0.0082(15) 0.0004(15) 0.0017(15)
C8 0.016(2) 0.0118(19) 0.0168(18) 0.0081(15) -0.0013(15) 0.0012(15)
C9 0.019(2) 0.015(2) 0.022(2) 0.0076(16) 0.0023(16) 0.0009(15)
C10 0.023(2) 0.018(2) 0.027(2) 0.0083(16) 0.0017(16) 0.0047(16)
C11 0.020(2) 0.0143(19) 0.0227(19) 0.0078(16) 0.0005(16) 0.0035(15)
C12 0.023(2) 0.021(2) 0.029(2) 0.0090(16) 0.0001(16) 0.0047(16)
C13 0.025(2) 0.019(2) 0.028(2) 0.0080(16) 0.0027(16) 0.0068(16)
C14 0.030(2) 0.024(2) 0.030(2) 0.0075(17) 0.0019(17) 0.0089(17)
C15 0.041(3) 0.037(2) 0.043(2) 0.0108(18) 0.0004(18) 0.0111(18)
C16 0.030(2) 0.029(2) 0.037(2) 0.0065(17) 0.0009(17) 0.0098(17)
C17 0.017(2) 0.0142(19) 0.0208(19) 0.0054(16) -0.0015(16) 0.0020(15)
C18 0.024(2) 0.019(2) 0.023(2) 0.0077(16) 0.0028(16) 0.0025(16)
C19 0.027(2) 0.020(2) 0.026(2) 0.0068(16) 0.0028(16) 0.0057(16)
C20 0.021(2) 0.015(2) 0.023(2) 0.0070(16) 0.0002(16) 0.0028(16)
C21 0.016(2) 0.0140(19) 0.0187(19) 0.0069(15) 0.0009(15) 0.0011(15)
C22 0.016(2) 0.0124(19) 0.0182(19) 0.0047(15) 0.0003(15) 0.0015(15)
C23 0.018(2) 0.0133(19) 0.0189(19) 0.0067(15) 0.0004(15) 0.0035(15)
C24 0.020(2) 0.016(2) 0.0198(19) 0.0081(16) 0.0009(16) 0.0025(15)
C25 0.021(2) 0.021(2) 0.024(2) 0.0059(16) 0.0025(16) 0.0056(16)
C26 0.027(2) 0.025(2) 0.027(2) 0.0082(17) -0.0018(16) 0.0070(17)
C27 0.029(2) 0.024(2) 0.030(2) 0.0079(17) -0.0017(17) 0.0096(17)
C28 0.025(2) 0.022(2) 0.026(2) 0.0069(16) -0.0009(16) 0.0072(16)
_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
O1 C1 1.240(6) . ?
N1 C6 1.362(7) . ?
N1 C3 1.390(7) . ?
N1 C8 1.465(7) . ?
N2 C7 1.291(7) . ?
N2 N3 1.360(7) . ?
N3 C23 1.404(8) . ?
N3 C17 1.446(7) . ?
C1 C2 1.459(7) 2_767 ?
C1 C2 1.460(7) . ?
C2 C3 1.388(8) . ?
C2 C1 1.459(7) 2_767 ?
C3 C4 1.404(7) . ?
C4 C5 1.370(8) . ?
C5 C6 1.405(7) . ?
C6 C7 1.424(8) . ?
C8 C9 1.512(8) . ?
C9 C10 1.535(8) . ?
C10 C11 1.486(8) . ?
C11 C16 1.383(9) . ?
C11 C12 1.386(9) . ?
C12 C13 1.371(8) . ?
C13 C14 1.367(9) . ?
C14 C15 1.377(10) . ?
C15 C16 1.368(9) . ?
C17 C22 1.374(7) . ?
C17 C18 1.377(8) . ?
C18 C19 1.398(8) . ?
C19 C20 1.378(8) . ?
C20 C21 1.365(8) . ?
C21 C22 1.374(8) . ?
C23 C24 1.383(8) . ?
C23 C28 1.388(8) . ?
C24 C25 1.374(9) . ?
C25 C26 1.366(9) . ?
C26 C27 1.363(9) . ?
C27 C28 1.384(9) . ?
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
C6 N1 C3 109.2(4) . . ?
C6 N1 C8 124.8(5) . . ?
C3 N1 C8 125.8(5) . . ?
C7 N2 N3 117.9(5) . . ?
N2 N3 C23 117.8(4) . . ?
N2 N3 C17 119.8(5) . . ?
C23 N3 C17 122.4(5) . . ?
O1 C1 C2 136.0(5) . 2_767 ?
O1 C1 C2 132.8(5) . . ?
C2 C1 C2 91.3(4) 2_767 . ?
C3 C2 C1 141.3(5) . 2_767 ?
C3 C2 C1 129.9(5) . . ?
C1 C2 C1 88.7(4) 2_767 . ?
C2 C3 N1 127.2(5) . . ?
C2 C3 C4 126.3(5) . . ?
N1 C3 C4 106.4(5) . . ?
C5 C4 C3 108.9(5) . . ?
C4 C5 C6 107.4(5) . . ?
N1 C6 C5 108.1(5) . . ?
N1 C6 C7 121.9(5) . . ?
C5 C6 C7 129.8(5) . . ?
N2 C7 C6 119.9(5) . . ?
N1 C8 C9 110.2(4) . . ?
C8 C9 C10 113.6(4) . . ?
C11 C10 C9 111.6(5) . . ?
C16 C11 C12 117.0(6) . . ?
C16 C11 C10 121.7(6) . . ?
C12 C11 C10 121.2(6) . . ?
C13 C12 C11 122.5(6) . . ?
C14 C13 C12 119.2(6) . . ?
C13 C14 C15 119.7(7) . . ?
C16 C15 C14 120.7(8) . . ?
C15 C16 C11 120.9(7) . . ?
C22 C17 C18 121.4(5) . . ?
C22 C17 N3 120.4(5) . . ?
C18 C17 N3 118.1(5) . . ?
C17 C18 C19 118.5(5) . . ?
C20 C19 C18 120.0(6) . . ?
C21 C20 C19 120.0(5) . . ?
C20 C21 C22 120.9(5) . . ?
C21 C22 C17 119.1(5) . . ?
C24 C23 C28 118.3(6) . . ?
C24 C23 N3 120.8(5) . . ?
C28 C23 N3 120.8(6) . . ?
C25 C24 C23 120.7(5) . . ?
C26 C25 C24 121.0(6) . . ?
C27 C26 C25 118.6(7) . . ?
C26 C27 C28 121.7(6) . . ?
C27 C28 C23 119.5(6) . . ?
_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.118