# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound-9
_database_code_depnum_ccdc_archive 'CCDC 1029448'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N3 O0'
_chemical_formula_weight         299.37

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 1 21/c 1'

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                   17.0546(9)
_cell_length_b                   5.5978(2)
_cell_length_c                   16.1901(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.328(4)
_cell_angle_gamma                90.00
_cell_volume                     1490.66(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1415
_cell_measurement_theta_min      2.6842
_cell_measurement_theta_max      71.4776

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4593
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         71.62
_reflns_number_total             2844
_reflns_number_gt                1816
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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)+(0.0833P)²+0.2273P] 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     SHELXL
_refine_ls_extinction_coef       0.0011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2844
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
N3 N 0.25910(14) 0.3572(4) 0.17562(13) 0.0495(6) Uani 1 1 d . . .
N2 N 0.28093(14) -0.0025(5) 0.40642(13) 0.0533(6) Uani 1 1 d . . .
C1 C 0.13753(17) -0.1114(5) 0.20187(15) 0.0450(6) Uani 1 1 d . . .
N1 N 0.17358(15) -0.2624(4) 0.33752(13) 0.0508(6) Uani 1 1 d . . .
C6 C 0.12145(17) -0.2903(5) 0.25706(16) 0.0495(7) Uani 1 1 d . . .
C10 C 0.31473(17) 0.3039(5) 0.31791(16) 0.0497(7) Uani 1 1 d . . .
C8 C 0.20455(16) 0.0299(5) 0.25323(15) 0.0454(6) Uani 1 1 d . . .
C13 C 0.31968(17) 0.5290(5) 0.20168(17) 0.0504(7) Uani 1 1 d . . .
C2 C 0.08820(18) -0.1058(5) 0.11842(16) 0.0544(7) Uani 1 1 d . . .
H9 H 0.0959 0.0119 0.0808 0.065 Uiso 1 1 calc R . .
C7 C 0.22351(17) -0.0689(5) 0.33648(15) 0.0477(7) Uani 1 1 d . . .
C12 C 0.35488(17) 0.5050(5) 0.28988(17) 0.0506(7) Uani 1 1 d . . .
C9 C 0.25459(17) 0.2224(5) 0.24512(15) 0.0455(6) Uani 1 1 d . . .
C20 C 0.2123(2) 0.3253(6) 0.08776(16) 0.0659(9) Uani 1 1 d . . .
H13A H 0.1582 0.3850 0.0810 0.099 Uiso 1 1 calc R . .
H13B H 0.2099 0.1585 0.0735 0.099 Uiso 1 1 calc R . .
H13C H 0.2377 0.4111 0.0505 0.099 Uiso 1 1 calc R . .
C11 C 0.32617(18) 0.1859(6) 0.39645(16) 0.0543(7) Uani 1 1 d . . .
C5 C 0.06142(18) -0.4606(6) 0.23003(18) 0.0579(8) Uani 1 1 d . . .
H15 H 0.0528 -0.5778 0.2674 0.069 Uiso 1 1 calc R . .
C18 C 0.1757(2) -0.4087(6) 0.41194(17) 0.0636(9) Uani 1 1 d . . .
H16A H 0.1308 -0.3673 0.4345 0.095 Uiso 1 1 calc R . .
H16B H 0.2258 -0.3816 0.4548 0.095 Uiso 1 1 calc R . .
H16C H 0.1718 -0.5742 0.3958 0.095 Uiso 1 1 calc R . .
C4 C 0.01482(19) -0.4527(6) 0.14671(19) 0.0618(8) Uani 1 1 d . . .
H17 H -0.0256 -0.5664 0.1271 0.074 Uiso 1 1 calc R . .
C3 C 0.0279(2) -0.2746(6) 0.09133(18) 0.0637(9) Uani 1 1 d . . .
H18 H -0.0046 -0.2698 0.0353 0.076 Uiso 1 1 calc R . .
C16 C 0.4393(2) 0.8412(6) 0.2806(2) 0.0686(9) Uani 1 1 d . . .
H19 H 0.4797 0.9490 0.3068 0.082 Uiso 1 1 calc R . .
C17 C 0.41597(19) 0.6659(6) 0.3295(2) 0.0617(8) Uani 1 1 d . . .
H20 H 0.4406 0.6552 0.3879 0.074 Uiso 1 1 calc R . .
C19 C 0.3923(2) 0.2602(7) 0.47382(18) 0.0781(11) Uani 1 1 d . . .
H21A H 0.3830 0.4217 0.4888 0.117 Uiso 1 1 calc R . .
H21B H 0.4440 0.2501 0.4610 0.117 Uiso 1 1 calc R . .
H21C H 0.3920 0.1563 0.5209 0.117 Uiso 1 1 calc R . .
C14 C 0.34312(19) 0.7053(6) 0.1525(2) 0.0615(8) Uani 1 1 d . . .
H22 H 0.3189 0.7187 0.0941 0.074 Uiso 1 1 calc R . .
C15 C 0.4036(2) 0.8589(6) 0.1939(2) 0.0674(9) Uani 1 1 d . . .
H23 H 0.4209 0.9778 0.1627 0.081 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
N3 C9 1.374(3) . ?
N3 C13 1.393(3) . ?
N3 C20 1.446(3) . ?
N2 C7 1.339(3) . ?
N2 C11 1.341(4) . ?
C1 C2 1.391(3) . ?
C1 C6 1.416(4) . ?
C1 C8 1.456(4) . ?
N1 C6 1.378(3) . ?
N1 C7 1.381(4) . ?
N1 C18 1.450(3) . ?
C6 C5 1.382(4) . ?
C10 C11 1.400(4) . ?
C10 C9 1.418(3) . ?
C10 C12 1.452(4) . ?
C8 C9 1.402(4) . ?
C8 C7 1.413(3) . ?
C13 C14 1.391(4) . ?
C13 C12 1.401(4) . ?
C2 C3 1.381(4) . ?
C2 H9 0.9300 . ?
C12 C17 1.398(4) . ?
C20 H13A 0.9600 . ?
C20 H13B 0.9600 . ?
C20 H13C 0.9600 . ?
C11 C19 1.506(4) . ?
C5 C4 1.374(4) . ?
C5 H15 0.9300 . ?
C18 H16A 0.9600 . ?
C18 H16B 0.9600 . ?
C18 H16C 0.9600 . ?
C4 C3 1.397(4) . ?
C4 H17 0.9300 . ?
C3 H18 0.9300 . ?
C16 C15 1.378(4) . ?
C16 C17 1.383(5) . ?
C16 H19 0.9300 . ?
C17 H20 0.9300 . ?
C19 H21A 0.9600 . ?
C19 H21B 0.9600 . ?
C19 H21C 0.9600 . ?
C14 C15 1.373(4) . ?
C14 H22 0.9300 . ?
C15 H23 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
C9 N3 C13 109.2(2) . . ?
C9 N3 C20 127.0(2) . . ?
C13 N3 C20 123.8(2) . . ?
C7 N2 C11 115.6(2) . . ?
C2 C1 C6 117.4(3) . . ?
C2 C1 C8 136.4(3) . . ?
C6 C1 C8 106.1(2) . . ?
C6 N1 C7 108.9(2) . . ?
C6 N1 C18 126.1(3) . . ?
C7 N1 C18 125.0(2) . . ?
N1 C6 C5 128.0(3) . . ?
N1 C6 C1 109.4(2) . . ?
C5 C6 C1 122.6(2) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 C12 133.3(3) . . ?
C9 C10 C12 106.7(2) . . ?
C9 C8 C7 113.5(2) . . ?
C9 C8 C1 140.3(2) . . ?
C7 C8 C1 106.2(2) . . ?
C14 C13 N3 128.2(3) . . ?
C14 C13 C12 122.7(3) . . ?
N3 C13 C12 109.0(2) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H9 119.9 . . ?
C1 C2 H9 119.9 . . ?
N2 C7 N1 121.5(2) . . ?
N2 C7 C8 129.0(3) . . ?
N1 C7 C8 109.4(2) . . ?
C17 C12 C13 118.2(3) . . ?
C17 C12 C10 135.4(3) . . ?
C13 C12 C10 106.4(2) . . ?
N3 C9 C8 131.8(2) . . ?
N3 C9 C10 108.6(2) . . ?
C8 C9 C10 119.6(2) . . ?
N3 C20 H13A 109.5 . . ?
N3 C20 H13B 109.5 . . ?
H13A C20 H13B 109.5 . . ?
N3 C20 H13C 109.5 . . ?
H13A C20 H13C 109.5 . . ?
H13B C20 H13C 109.5 . . ?
N2 C11 C10 122.2(3) . . ?
N2 C11 C19 116.4(3) . . ?
C10 C11 C19 121.3(3) . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H15 120.8 . . ?
C6 C5 H15 120.8 . . ?
N1 C18 H16A 109.5 . . ?
N1 C18 H16B 109.5 . . ?
H16A C18 H16B 109.5 . . ?
N1 C18 H16C 109.5 . . ?
H16A C18 H16C 109.5 . . ?
H16B C18 H16C 109.5 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H17 119.9 . . ?
C3 C4 H17 119.9 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H18 119.5 . . ?
C4 C3 H18 119.5 . . ?
C15 C16 C17 121.2(3) . . ?
C15 C16 H19 119.4 . . ?
C17 C16 H19 119.4 . . ?
C16 C17 C12 119.1(3) . . ?
C16 C17 H20 120.4 . . ?
C12 C17 H20 120.4 . . ?
C11 C19 H21A 109.5 . . ?
C11 C19 H21B 109.5 . . ?
H21A C19 H21B 109.5 . . ?
C11 C19 H21C 109.5 . . ?
H21A C19 H21C 109.5 . . ?
H21B C19 H21C 109.5 . . ?
C15 C14 C13 117.2(3) . . ?
C15 C14 H22 121.4 . . ?
C13 C14 H22 121.4 . . ?
C14 C15 C16 121.6(3) . . ?
C14 C15 H23 119.2 . . ?
C16 C15 H23 119.2 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        71.62
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.048
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound-15
_database_code_depnum_ccdc_archive 'CCDC 1029449'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H21 N3'
_chemical_formula_weight         375.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   13.1017(10)
_cell_length_b                   20.7038(19)
_cell_length_c                   7.3429(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.921(9)
_cell_angle_gamma                90.00
_cell_volume                     1915.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_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            4657
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         24.71
_reflns_number_total             3032
_reflns_number_gt                2100
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_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 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)+(0.0635P)²+0.1189P] 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         3032
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
C23 C -0.07530(17) 0.87658(11) 0.7814(3) 0.0594(6) Uani 1 1 d . . .
H23 H -0.0362 0.8944 0.8954 0.071 Uiso 1 1 calc R . .
C22 C -0.17778(18) 0.89698(12) 0.7007(3) 0.0656(7) Uani 1 1 d . . .
H22 H -0.2074 0.9286 0.7604 0.079 Uiso 1 1 calc R . .
N2 N 0.08460(12) 0.73951(9) 0.7831(2) 0.0512(5) Uani 1 1 d . . .
C17 C 0.26540(15) 0.81393(12) 0.9513(2) 0.0501(5) Uani 1 1 d . . .
C10 C 0.16680(15) 0.84302(11) 0.8576(3) 0.0484(5) Uani 1 1 d . . .
C7 C 0.27433(16) 0.74662(12) 0.9609(3) 0.0504(5) Uani 1 1 d . . .
C18 C -0.03019(15) 0.82959(10) 0.6935(3) 0.0476(5) Uani 1 1 d . . .
C9 C 0.07819(15) 0.80388(11) 0.7806(3) 0.0483(5) Uani 1 1 d . . .
C8 C 0.17897(16) 0.71432(11) 0.8693(3) 0.0498(5) Uani 1 1 d . . .
C11 C 0.18497(16) 0.91215(11) 0.8594(3) 0.0520(6) Uani 1 1 d . . .
N3 N 0.33877(13) 0.86228(10) 1.0153(2) 0.0575(5) Uani 1 1 d . . .
C19 C -0.09184(15) 0.80348(10) 0.5256(3) 0.0514(5) Uani 1 1 d . . .
H19 H -0.0631 0.7713 0.4662 0.062 Uiso 1 1 calc R . .
N1 N 0.19476(14) 0.64879(9) 0.8808(2) 0.0558(5) Uani 1 1 d . . .
C1 C 0.29880(18) 0.63717(12) 0.9770(3) 0.0576(6) Uani 1 1 d . . .
C16 C 0.29172(18) 0.92131(12) 0.9595(3) 0.0571(6) Uani 1 1 d . . .
C6 C 0.35222(17) 0.69647(13) 1.0304(3) 0.0568(6) Uani 1 1 d . . .
C21 C -0.23648(17) 0.87101(12) 0.5330(3) 0.0630(6) Uani 1 1 d . . .
H21 H -0.3053 0.8856 0.4792 0.076 Uiso 1 1 calc R . .
C20 C -0.19470(16) 0.82369(11) 0.4435(3) 0.0565(6) Uani 1 1 d . . .
C15 C 0.3381(2) 0.98219(14) 0.9876(3) 0.0726(7) Uani 1 1 d . . .
H15 H 0.4086 0.9875 1.0562 0.087 Uiso 1 1 calc R . .
C2 C 0.3484(2) 0.57771(13) 1.0173(3) 0.0745(7) Uani 1 1 d . . .
H2 H 0.3114 0.5394 0.9809 0.089 Uiso 1 1 calc R . .
C12 C 0.12542(19) 0.96643(12) 0.7828(3) 0.0633(6) Uani 1 1 d . . .
H12 H 0.0547 0.9620 0.7141 0.076 Uiso 1 1 calc R . .
C26 C 0.44869(17) 0.85436(14) 1.1209(3) 0.0796(8) Uani 1 1 d . . .
H26A H 0.4817 0.8960 1.1471 0.119 Uiso 1 1 calc R . .
H26B H 0.4849 0.8293 1.0477 0.119 Uiso 1 1 calc R . .
H26C H 0.4525 0.8325 1.2378 0.119 Uiso 1 1 calc R . .
C3 C 0.4553(2) 0.57752(17) 1.1142(3) 0.0871(9) Uani 1 1 d . . .
H3 H 0.4910 0.5384 1.1429 0.105 Uiso 1 1 calc R . .
C5 C 0.45973(18) 0.69339(15) 1.1289(3) 0.0767(8) Uani 1 1 d . . .
H5 H 0.4978 0.7312 1.1677 0.092 Uiso 1 1 calc R . .
C24 C -0.2588(2) 0.79312(14) 0.2627(4) 0.0947(10) Uani 1 1 d . . .
H24A H -0.3283 0.8122 0.2258 0.142 Uiso 1 1 calc R . .
H24B H -0.2650 0.7476 0.2818 0.142 Uiso 1 1 calc R . .
H24C H -0.2242 0.8001 0.1649 0.142 Uiso 1 1 calc R . .
C25 C 0.11412(19) 0.60075(12) 0.8094(3) 0.0688(7) Uani 1 1 d . . .
H25A H 0.1331 0.5753 0.7144 0.103 Uiso 1 1 calc R . .
H25B H 0.0473 0.6217 0.7550 0.103 Uiso 1 1 calc R . .
H25C H 0.1082 0.5733 0.9114 0.103 Uiso 1 1 calc R . .
C13 C 0.1718(2) 1.02646(13) 0.8092(4) 0.0771(7) Uani 1 1 d . . .
H13 H 0.1320 1.0625 0.7575 0.093 Uiso 1 1 calc R . .
C4 C 0.5094(2) 0.63443(18) 1.1684(4) 0.0886(10) Uani 1 1 d . . .
H4 H 0.5811 0.6330 1.2332 0.106 Uiso 1 1 calc R . .
C14 C 0.2766(2) 1.03401(14) 0.9113(4) 0.0829(8) Uani 1 1 d . . .
H14 H 0.3059 1.0752 0.9286 0.100 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
C23 C22 1.377(3) . ?
C23 C18 1.386(3) . ?
C23 H23 0.9300 . ?
C22 C21 1.370(3) . ?
C22 H22 0.9300 . ?
N2 C8 1.331(2) . ?
N2 C9 1.335(3) . ?
C17 N3 1.378(3) . ?
C17 C7 1.399(3) . ?
C17 C10 1.420(3) . ?
C10 C9 1.401(3) . ?
C10 C11 1.450(3) . ?
C7 C8 1.414(3) . ?
C7 C6 1.447(3) . ?
C18 C19 1.385(3) . ?
C18 C9 1.487(3) . ?
C8 N1 1.371(3) . ?
C11 C12 1.396(3) . ?
C11 C16 1.403(3) . ?
N3 C16 1.379(3) . ?
N3 C26 1.445(3) . ?
C19 C20 1.382(3) . ?
C19 H19 0.9300 . ?
N1 C1 1.373(3) . ?
N1 C25 1.441(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.414(3) . ?
C16 C15 1.390(3) . ?
C6 C5 1.397(3) . ?
C21 C20 1.374(3) . ?
C21 H21 0.9300 . ?
C20 C24 1.503(3) . ?
C15 C14 1.366(3) . ?
C15 H15 0.9300 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9300 . ?
C12 C13 1.374(3) . ?
C12 H12 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C5 C4 1.376(4) . ?
C5 H5 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C4 H4 0.9300 . ?
C14 H14 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
C22 C23 C18 120.3(2) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
C21 C22 C23 120.5(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C8 N2 C9 116.39(19) . . ?
N3 C17 C7 131.74(19) . . ?
N3 C17 C10 108.3(2) . . ?
C7 C17 C10 120.0(2) . . ?
C9 C10 C17 119.5(2) . . ?
C9 C10 C11 133.6(2) . . ?
C17 C10 C11 106.79(18) . . ?
C17 C7 C8 113.36(19) . . ?
C17 C7 C6 140.7(2) . . ?
C8 C7 C6 105.9(2) . . ?
C19 C18 C23 117.99(18) . . ?
C19 C18 C9 119.86(19) . . ?
C23 C18 C9 122.02(18) . . ?
N2 C9 C10 121.98(19) . . ?
N2 C9 C18 114.36(19) . . ?
C10 C9 C18 123.7(2) . . ?
N2 C8 N1 121.4(2) . . ?
N2 C8 C7 128.7(2) . . ?
N1 C8 C7 109.87(19) . . ?
C12 C11 C16 118.0(2) . . ?
C12 C11 C10 136.0(2) . . ?
C16 C11 C10 106.0(2) . . ?
C17 N3 C16 109.23(17) . . ?
C17 N3 C26 126.8(2) . . ?
C16 N3 C26 123.93(19) . . ?
C20 C19 C18 122.1(2) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C8 N1 C1 108.45(19) . . ?
C8 N1 C25 125.26(18) . . ?
C1 N1 C25 126.2(2) . . ?
N1 C1 C2 127.3(2) . . ?
N1 C1 C6 109.7(2) . . ?
C2 C1 C6 123.0(2) . . ?
N3 C16 C15 128.2(2) . . ?
N3 C16 C11 109.6(2) . . ?
C15 C16 C11 122.2(2) . . ?
C5 C6 C1 117.1(2) . . ?
C5 C6 C7 136.8(3) . . ?
C1 C6 C7 106.11(19) . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C20 C19 118.45(19) . . ?
C21 C20 C24 121.5(2) . . ?
C19 C20 C24 120.0(2) . . ?
C14 C15 C16 117.8(2) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C1 C2 C3 117.4(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N3 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 C13 C14 120.9(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        29.22
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.033
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound-30
_database_code_depnum_ccdc_archive 'CCDC 1029450'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H27 N3 O3'
_chemical_formula_weight         477.55

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pca2(1) '

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

_cell_length_a                   21.214(3)
_cell_length_b                   8.2654(11)
_cell_length_c                   27.017(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4737.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      21.86

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2016
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            43207
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8319
_reflns_number_gt                6938
_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 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)+(0.0667P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(12)
_refine_ls_number_reflns         8319
_refine_ls_number_parameters     661
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
N5 N 0.39739(10) 0.7974(3) 0.42558(9) 0.0506(6) Uani 1 1 d . . .
C50 C 0.43292(12) 0.7267(3) 0.34847(11) 0.0470(7) Uani 1 1 d . . .
C40 C 0.54248(12) 0.6115(3) 0.38126(11) 0.0468(6) Uani 1 1 d . . .
C38 C 0.55675(13) 0.6530(3) 0.47162(11) 0.0509(7) Uani 1 1 d . . .
C49 C 0.38201(12) 0.7890(3) 0.37567(11) 0.0471(7) Uani 1 1 d . . .
C41 C 0.57675(12) 0.5322(3) 0.34213(12) 0.0482(7) Uani 1 1 d . . .
C48 C 0.45923(12) 0.7394(3) 0.42991(11) 0.0454(7) Uani 1 1 d . . .
N6 N 0.63290(10) 0.5098(3) 0.41366(10) 0.0560(7) Uani 1 1 d . . .
C31 C 0.57904(14) 0.6608(3) 0.52262(12) 0.0554(8) Uani 1 1 d . . .
C47 C 0.48214(12) 0.6892(3) 0.38409(11) 0.0434(6) Uani 1 1 d . . .
C51 C 0.42759(14) 0.7196(3) 0.29702(12) 0.0551(7) Uani 1 1 d . . .
H5 H 0.4611 0.6821 0.2780 0.066 Uiso 1 1 calc R . .
O5 O 0.36182(12) 0.7656(3) 0.22447(9) 0.0868(8) Uani 1 1 d . . .
C53 C 0.32224(14) 0.8268(3) 0.30290(13) 0.0591(8) Uani 1 1 d . . .
H3 H 0.2853 0.8596 0.2873 0.071 Uiso 1 1 calc R . .
N4 N 0.48545(11) 0.7931(3) 0.51935(9) 0.0559(6) Uani 1 1 d . . .
C36 C 0.53504(15) 0.7505(3) 0.54965(12) 0.0576(8) Uani 1 1 d . . .
C54 C 0.32658(13) 0.8365(3) 0.35321(12) 0.0556(8) Uani 1 1 d . . .
H2 H 0.2929 0.8743 0.3720 0.067 Uiso 1 1 calc R . .
C42 C 0.63217(13) 0.4741(4) 0.36398(14) 0.0585(8) Uani 1 1 d . . .
C37 C 0.49778(13) 0.7330(3) 0.47234(11) 0.0480(7) Uani 1 1 d . . .
C39 C 0.57811(12) 0.5920(3) 0.42514(11) 0.0474(7) Uani 1 1 d . . .
C46 C 0.56591(14) 0.4982(4) 0.29215(13) 0.0598(8) Uani 1 1 d . . .
H20 H 0.5286 0.5319 0.2772 0.072 Uiso 1 1 calc R . .
C43 C 0.67689(15) 0.3900(4) 0.33600(17) 0.0784(11) Uani 1 1 d . . .
H17 H 0.7140 0.3536 0.3505 0.094 Uiso 1 1 calc R . .
C45 C 0.60999(16) 0.4152(4) 0.26498(14) 0.0663(9) Uani 1 1 d . . .
C52 C 0.37227(15) 0.7686(4) 0.27436(12) 0.0585(8) Uani 1 1 d . . .
C32 C 0.63195(16) 0.6025(4) 0.54894(14) 0.0716(9) Uani 1 1 d . . .
H28 H 0.6620 0.5395 0.5329 0.086 Uiso 1 1 calc R . .
C35 C 0.54293(18) 0.7862(4) 0.59903(14) 0.0750(10) Uani 1 1 d . . .
H25 H 0.5130 0.8476 0.6157 0.090 Uiso 1 1 calc R . .
O6 O 0.59460(13) 0.3878(3) 0.21638(10) 0.0922(8) Uani 1 1 d . . .
C33 C 0.63890(19) 0.6389(4) 0.59806(15) 0.0798(11) Uani 1 1 d . . .
C59 C 0.34810(15) 0.7571(5) 0.46211(13) 0.0696(9) Uani 1 1 d . . .
H1A H 0.3246 0.8528 0.4701 0.104 Uiso 1 1 calc R . .
H1B H 0.3674 0.7151 0.4916 0.104 Uiso 1 1 calc R . .
H1C H 0.3203 0.6772 0.4484 0.104 Uiso 1 1 calc R . .
C34 C 0.5950(2) 0.7306(5) 0.62326(15) 0.0877(12) Uani 1 1 d . . .
H26 H 0.6009 0.7544 0.6566 0.105 Uiso 1 1 calc R . .
O4 O 0.68973(15) 0.5916(4) 0.62628(11) 0.1118(10) Uani 1 1 d . . .
C55 C 0.44623(16) 0.9327(4) 0.53116(13) 0.0732(9) Uani 1 1 d . . .
H30A H 0.4118 0.8992 0.5518 0.110 Uiso 1 1 calc R . .
H30B H 0.4300 0.9788 0.5011 0.110 Uiso 1 1 calc R . .
H30C H 0.4710 1.0120 0.5483 0.110 Uiso 1 1 calc R . .
C44 C 0.66525(16) 0.3620(4) 0.28686(16) 0.0762(10) Uani 1 1 d . . .
H18 H 0.6948 0.3065 0.2680 0.091 Uiso 1 1 calc R . .
C57 C 0.68618(14) 0.4744(5) 0.44521(15) 0.0819(11) Uani 1 1 d . . .
H22A H 0.7223 0.4498 0.4251 0.123 Uiso 1 1 calc R . .
H22B H 0.6764 0.3832 0.4659 0.123 Uiso 1 1 calc R . .
H22C H 0.6952 0.5666 0.4656 0.123 Uiso 1 1 calc R . .
C56 C 0.7350(2) 0.4922(6) 0.6037(2) 0.1090(16) Uani 1 1 d . . .
H29A H 0.7158 0.3917 0.5942 0.164 Uiso 1 1 calc R . .
H29B H 0.7686 0.4715 0.6266 0.164 Uiso 1 1 calc R . .
H29C H 0.7514 0.5455 0.5749 0.164 Uiso 1 1 calc R . .
C60 C 0.40607(19) 0.6853(5) 0.19392(14) 0.0893(12) Uani 1 1 d . . .
H8A H 0.4458 0.7404 0.1956 0.134 Uiso 1 1 calc R . .
H8B H 0.3912 0.6850 0.1604 0.134 Uiso 1 1 calc R . .
H8C H 0.4112 0.5758 0.2051 0.134 Uiso 1 1 calc R . .
C58 C 0.6392(2) 0.3086(6) 0.18611(18) 0.1122(16) Uani 1 1 d . . .
H21A H 0.6778 0.3693 0.1858 0.168 Uiso 1 1 calc R . .
H21B H 0.6230 0.3005 0.1530 0.168 Uiso 1 1 calc R . .
H21C H 0.6471 0.2022 0.1989 0.168 Uiso 1 1 calc R . .
C20 C 0.32681(12) 0.2355(3) 0.46239(11) 0.0451(7) Uani 1 1 d . . .
N2 N 0.35831(11) 0.2790(3) 0.38182(10) 0.0518(6) Uani 1 1 d . . .
C11 C 0.18903(11) 0.0242(3) 0.47868(10) 0.0410(6) Uani 1 1 d . . .
C19 C 0.37616(13) 0.2896(3) 0.43130(12) 0.0491(7) Uani 1 1 d . . .
C17 C 0.27712(12) 0.1800(3) 0.42935(10) 0.0457(6) Uani 1 1 d . . .
O2 O 0.39217(10) 0.3306(3) 0.58280(8) 0.0713(6) Uani 1 1 d . . .
N3 N 0.12707(10) -0.0175(3) 0.41100(8) 0.0461(6) Uani 1 1 d . . .
C16 C 0.20461(13) 0.0028(3) 0.52840(11) 0.0510(7) Uani 1 1 d . . .
H60 H 0.2422 0.0444 0.5407 0.061 Uiso 1 1 calc R . .
C6 C 0.21073(15) 0.2024(3) 0.26608(11) 0.0546(7) Uani 1 1 d . . .
C7 C 0.25533(13) 0.2004(3) 0.34124(10) 0.0478(7) Uani 1 1 d . . .
C1 C 0.16779(13) 0.1220(3) 0.29780(11) 0.0509(7) Uani 1 1 d . . .
C21 C 0.33434(13) 0.2545(3) 0.51287(11) 0.0508(7) Uani 1 1 d . . .
H54 H 0.3017 0.2251 0.5340 0.061 Uiso 1 1 calc R . .
O3 O 0.17481(11) -0.1074(3) 0.60839(8) 0.0730(6) Uani 1 1 d . . .
C9 C 0.17950(12) 0.0683(3) 0.39501(10) 0.0434(6) Uani 1 1 d . . .
C8 C 0.19616(12) 0.1230(3) 0.34651(10) 0.0457(6) Uani 1 1 d . . .
N1 N 0.26322(12) 0.2487(3) 0.29283(9) 0.0554(6) Uani 1 1 d . . .
C18 C 0.29662(12) 0.2169(3) 0.38123(11) 0.0463(6) Uani 1 1 d . . .
C12 C 0.13224(12) -0.0444(3) 0.46103(10) 0.0448(7) Uani 1 1 d . . .
C15 C 0.16432(14) -0.0796(4) 0.55931(11) 0.0538(7) Uani 1 1 d . . .
C13 C 0.09227(14) -0.1295(4) 0.49216(11) 0.0561(8) Uani 1 1 d . . .
H44 H 0.0551 -0.1745 0.4802 0.067 Uiso 1 1 calc R . .
C22 C 0.38996(13) 0.3170(3) 0.53258(11) 0.0518(7) Uani 1 1 d . . .
C10 C 0.21852(11) 0.0991(3) 0.43637(10) 0.0425(6) Uani 1 1 d . . .
C24 C 0.43255(13) 0.3467(3) 0.45092(12) 0.0526(7) Uani 1 1 d . . .
H57 H 0.4656 0.3754 0.4300 0.063 Uiso 1 1 calc R . .
C14 C 0.10848(14) -0.1458(4) 0.54065(12) 0.0604(8) Uani 1 1 d . . .
H45 H 0.0818 -0.2022 0.5618 0.072 Uiso 1 1 calc R . .
C23 C 0.43920(14) 0.3602(3) 0.50120(12) 0.0538(7) Uani 1 1 d . . .
H56 H 0.4768 0.3985 0.5144 0.065 Uiso 1 1 calc R . .
C5 C 0.19817(18) 0.2265(4) 0.21678(12) 0.0695(9) Uani 1 1 d . . .
H31 H 0.2271 0.2804 0.1969 0.083 Uiso 1 1 calc R . .
C2 C 0.11084(16) 0.0691(4) 0.27671(12) 0.0652(8) Uani 1 1 d . . .
H35 H 0.0809 0.0180 0.2964 0.078 Uiso 1 1 calc R . .
C29 C 0.40573(15) 0.2330(4) 0.34548(14) 0.0703(9) Uani 1 1 d . . .
H51A H 0.4306 0.3260 0.3369 0.105 Uiso 1 1 calc R . .
H51B H 0.3853 0.1919 0.3164 0.105 Uiso 1 1 calc R . .
H51C H 0.4325 0.1509 0.3592 0.105 Uiso 1 1 calc R . .
C4 C 0.14328(19) 0.1712(4) 0.19720(12) 0.0733(10) Uani 1 1 d . . .
H32 H 0.1349 0.1855 0.1637 0.088 Uiso 1 1 calc R . .
C3 C 0.09926(17) 0.0925(5) 0.22756(12) 0.0715(9) Uani 1 1 d . . .
C27 C 0.07303(14) -0.0714(5) 0.38352(13) 0.0707(9) Uani 1 1 d . . .
H42A H 0.0864 -0.1426 0.3575 0.106 Uiso 1 1 calc R . .
H42B H 0.0518 0.0203 0.3695 0.106 Uiso 1 1 calc R . .
H42C H 0.0448 -0.1280 0.4052 0.106 Uiso 1 1 calc R . .
O1 O 0.04480(14) 0.0433(4) 0.20400(10) 0.0974(8) Uani 1 1 d . . .
C25 C 0.30321(18) 0.3795(4) 0.27485(14) 0.0770(10) Uani 1 1 d . . .
H38A H 0.3346 0.3363 0.2529 0.116 Uiso 1 1 calc R . .
H38B H 0.3235 0.4313 0.3024 0.116 Uiso 1 1 calc R . .
H38C H 0.2779 0.4570 0.2574 0.116 Uiso 1 1 calc R . .
C26 C 0.00110(18) -0.0501(6) 0.23083(16) 0.0922(12) Uani 1 1 d . . .
H34A H 0.0206 -0.1494 0.2411 0.138 Uiso 1 1 calc R . .
H34B H -0.0346 -0.0737 0.2103 0.138 Uiso 1 1 calc R . .
H34C H -0.0125 0.0092 0.2595 0.138 Uiso 1 1 calc R . .
C28 C 0.22760(18) -0.0347(5) 0.63090(13) 0.0836(11) Uani 1 1 d . . .
H59A H 0.2655 -0.0784 0.6168 0.125 Uiso 1 1 calc R . .
H59B H 0.2269 -0.0561 0.6658 0.125 Uiso 1 1 calc R . .
H59C H 0.2264 0.0800 0.6254 0.125 Uiso 1 1 calc R . .
C30 C 0.44677(17) 0.3952(6) 0.60487(14) 0.0930(13) Uani 1 1 d . . .
H58A H 0.4820 0.3257 0.5981 0.140 Uiso 1 1 calc R . .
H58B H 0.4407 0.4031 0.6400 0.140 Uiso 1 1 calc R . .
H58C H 0.4549 0.5008 0.5915 0.140 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
N5 C49 1.389(4) . ?
N5 C48 1.402(3) . ?
N5 C59 1.476(4) . ?
C50 C51 1.396(4) . ?
C50 C49 1.404(4) . ?
C50 C47 1.454(4) . ?
C40 C39 1.415(4) . ?
C40 C47 1.434(4) . ?
C40 C41 1.441(4) . ?
C38 C37 1.415(4) . ?
C38 C39 1.427(4) . ?
C38 C31 1.458(4) . ?
C49 C54 1.380(4) . ?
C41 C46 1.398(4) . ?
C41 C42 1.400(4) . ?
C48 C47 1.393(4) . ?
C48 C37 1.409(4) . ?
N6 C42 1.374(4) . ?
N6 C39 1.382(3) . ?
N6 C57 1.446(4) . ?
C31 C36 1.398(4) . ?
C31 C32 1.413(4) . ?
C51 C52 1.384(4) . ?
C51 H5 0.9300 . ?
O5 C52 1.366(4) . ?
O5 C60 1.416(5) . ?
C53 C54 1.364(4) . ?
C53 C52 1.397(5) . ?
C53 H3 0.9300 . ?
N4 C36 1.379(4) . ?
N4 C37 1.388(4) . ?
N4 C55 1.458(4) . ?
C36 C35 1.377(5) . ?
C54 H2 0.9300 . ?
C42 C43 1.398(5) . ?
C46 C45 1.372(4) . ?
C46 H20 0.9300 . ?
C43 C44 1.370(5) . ?
C43 H17 0.9300 . ?
C45 O6 1.372(4) . ?
C45 C44 1.385(5) . ?
C32 C33 1.369(5) . ?
C32 H28 0.9300 . ?
C35 C34 1.364(5) . ?
C35 H25 0.9300 . ?
O6 C58 1.411(5) . ?
C33 O4 1.377(4) . ?
C33 C34 1.380(6) . ?
C59 H1A 0.9600 . ?
C59 H1B 0.9600 . ?
C59 H1C 0.9600 . ?
C34 H26 0.9300 . ?
O4 C56 1.402(6) . ?
C55 H30A 0.9600 . ?
C55 H30B 0.9600 . ?
C55 H30C 0.9600 . ?
C44 H18 0.9300 . ?
C57 H22A 0.9600 . ?
C57 H22B 0.9600 . ?
C57 H22C 0.9600 . ?
C56 H29A 0.9600 . ?
C56 H29B 0.9600 . ?
C56 H29C 0.9600 . ?
C60 H8A 0.9600 . ?
C60 H8B 0.9600 . ?
C60 H8C 0.9600 . ?
C58 H21A 0.9600 . ?
C58 H21B 0.9600 . ?
C58 H21C 0.9600 . ?
C20 C21 1.382(4) . ?
C20 C19 1.415(4) . ?
C20 C17 1.455(4) . ?
N2 C19 1.392(4) . ?
N2 C18 1.406(4) . ?
N2 C29 1.456(4) . ?
C11 C16 1.395(4) . ?
C11 C12 1.414(4) . ?
C11 C10 1.443(4) . ?
C19 C24 1.391(4) . ?
C17 C18 1.398(4) . ?
C17 C10 1.424(4) . ?
O2 C22 1.362(4) . ?
O2 C30 1.408(4) . ?
N3 C12 1.374(4) . ?
N3 C9 1.388(3) . ?
N3 C27 1.437(4) . ?
C16 C15 1.376(4) . ?
C16 H60 0.9300 . ?
C6 C5 1.373(4) . ?
C6 N1 1.382(4) . ?
C6 C1 1.416(4) . ?
C7 N1 1.378(4) . ?
C7 C18 1.398(4) . ?
C7 C8 1.416(4) . ?
C1 C2 1.406(4) . ?
C1 C8 1.447(4) . ?
C21 C22 1.394(4) . ?
C21 H54 0.9300 . ?
O3 C15 1.364(3) . ?
O3 C28 1.409(4) . ?
C9 C10 1.414(4) . ?
C9 C8 1.430(4) . ?
N1 C25 1.457(4) . ?
C12 C13 1.386(4) . ?
C15 C14 1.399(4) . ?
C13 C14 1.361(4) . ?
C13 H44 0.9300 . ?
C22 C23 1.392(4) . ?
C24 C23 1.370(4) . ?
C24 H57 0.9300 . ?
C14 H45 0.9300 . ?
C23 H56 0.9300 . ?
C5 C4 1.358(5) . ?
C5 H31 0.9300 . ?
C2 C3 1.364(5) . ?
C2 H35 0.9300 . ?
C29 H51A 0.9600 . ?
C29 H51B 0.9600 . ?
C29 H51C 0.9600 . ?
C4 C3 1.403(5) . ?
C4 H32 0.9300 . ?
C3 O1 1.380(4) . ?
C27 H42A 0.9600 . ?
C27 H42B 0.9600 . ?
C27 H42C 0.9600 . ?
O1 C26 1.407(5) . ?
C25 H38A 0.9600 . ?
C25 H38B 0.9600 . ?
C25 H38C 0.9600 . ?
C26 H34A 0.9600 . ?
C26 H34B 0.9600 . ?
C26 H34C 0.9600 . ?
C28 H59A 0.9600 . ?
C28 H59B 0.9600 . ?
C28 H59C 0.9600 . ?
C30 H58A 0.9600 . ?
C30 H58B 0.9600 . ?
C30 H58C 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
C49 N5 C48 106.5(2) . . ?
C49 N5 C59 118.1(2) . . ?
C48 N5 C59 122.0(2) . . ?
C51 C50 C49 118.3(3) . . ?
C51 C50 C47 135.1(3) . . ?
C49 C50 C47 106.5(3) . . ?
C39 C40 C47 118.9(3) . . ?
C39 C40 C41 107.1(2) . . ?
C47 C40 C41 133.9(3) . . ?
C37 C38 C39 117.2(3) . . ?
C37 C38 C31 104.7(3) . . ?
C39 C38 C31 138.1(3) . . ?
C54 C49 N5 127.8(3) . . ?
C54 C49 C50 122.0(3) . . ?
N5 C49 C50 110.2(2) . . ?
C46 C41 C42 118.4(3) . . ?
C46 C41 C40 135.8(3) . . ?
C42 C41 C40 105.7(3) . . ?
C47 C48 N5 110.8(2) . . ?
C47 C48 C37 120.6(2) . . ?
N5 C48 C37 128.6(3) . . ?
C42 N6 C39 108.4(2) . . ?
C42 N6 C57 122.8(3) . . ?
C39 N6 C57 128.7(3) . . ?
C36 C31 C32 116.6(3) . . ?
C36 C31 C38 107.5(3) . . ?
C32 C31 C38 135.9(3) . . ?
C48 C47 C40 119.5(3) . . ?
C48 C47 C50 105.9(2) . . ?
C40 C47 C50 134.5(3) . . ?
C52 C51 C50 119.8(3) . . ?
C52 C51 H5 120.1 . . ?
C50 C51 H5 120.1 . . ?
C52 O5 C60 118.4(3) . . ?
C54 C53 C52 121.2(3) . . ?
C54 C53 H3 119.4 . . ?
C52 C53 H3 119.4 . . ?
C36 N4 C37 107.9(2) . . ?
C36 N4 C55 120.5(3) . . ?
C37 N4 C55 126.2(3) . . ?
C35 C36 N4 127.8(3) . . ?
C35 C36 C31 122.6(3) . . ?
N4 C36 C31 109.6(3) . . ?
C53 C54 C49 118.6(3) . . ?
C53 C54 H2 120.7 . . ?
C49 C54 H2 120.7 . . ?
N6 C42 C43 128.8(3) . . ?
N6 C42 C41 110.3(3) . . ?
C43 C42 C41 120.8(4) . . ?
N4 C37 C48 128.4(2) . . ?
N4 C37 C38 110.3(2) . . ?
C48 C37 C38 121.3(3) . . ?
N6 C39 C40 108.5(3) . . ?
N6 C39 C38 129.7(3) . . ?
C40 C39 C38 121.8(2) . . ?
C45 C46 C41 120.3(3) . . ?
C45 C46 H20 119.8 . . ?
C41 C46 H20 119.8 . . ?
C44 C43 C42 119.1(3) . . ?
C44 C43 H17 120.5 . . ?
C42 C43 H17 120.5 . . ?
O6 C45 C46 115.6(3) . . ?
O6 C45 C44 123.9(3) . . ?
C46 C45 C44 120.5(3) . . ?
O5 C52 C51 124.7(3) . . ?
O5 C52 C53 115.3(3) . . ?
C51 C52 C53 120.0(3) . . ?
C33 C32 C31 119.9(4) . . ?
C33 C32 H28 120.1 . . ?
C31 C32 H28 120.1 . . ?
C34 C35 C36 119.4(4) . . ?
C34 C35 H25 120.3 . . ?
C36 C35 H25 120.3 . . ?
C45 O6 C58 118.1(3) . . ?
C32 C33 O4 123.9(4) . . ?
C32 C33 C34 121.8(3) . . ?
O4 C33 C34 114.3(4) . . ?
N5 C59 H1A 109.5 . . ?
N5 C59 H1B 109.5 . . ?
H1A C59 H1B 109.5 . . ?
N5 C59 H1C 109.5 . . ?
H1A C59 H1C 109.5 . . ?
H1B C59 H1C 109.5 . . ?
C35 C34 C33 119.6(4) . . ?
C35 C34 H26 120.2 . . ?
C33 C34 H26 120.2 . . ?
C33 O4 C56 117.5(3) . . ?
N4 C55 H30A 109.5 . . ?
N4 C55 H30B 109.5 . . ?
H30A C55 H30B 109.5 . . ?
N4 C55 H30C 109.5 . . ?
H30A C55 H30C 109.5 . . ?
H30B C55 H30C 109.5 . . ?
C43 C44 C45 120.8(3) . . ?
C43 C44 H18 119.6 . . ?
C45 C44 H18 119.6 . . ?
N6 C57 H22A 109.5 . . ?
N6 C57 H22B 109.5 . . ?
H22A C57 H22B 109.5 . . ?
N6 C57 H22C 109.5 . . ?
H22A C57 H22C 109.5 . . ?
H22B C57 H22C 109.5 . . ?
O4 C56 H29A 109.5 . . ?
O4 C56 H29B 109.5 . . ?
H29A C56 H29B 109.5 . . ?
O4 C56 H29C 109.5 . . ?
H29A C56 H29C 109.5 . . ?
H29B C56 H29C 109.5 . . ?
O5 C60 H8A 109.5 . . ?
O5 C60 H8B 109.5 . . ?
H8A C60 H8B 109.5 . . ?
O5 C60 H8C 109.5 . . ?
H8A C60 H8C 109.5 . . ?
H8B C60 H8C 109.5 . . ?
O6 C58 H21A 109.5 . . ?
O6 C58 H21B 109.5 . . ?
H21A C58 H21B 109.5 . . ?
O6 C58 H21C 109.5 . . ?
H21A C58 H21C 109.5 . . ?
H21B C58 H21C 109.5 . . ?
C21 C20 C19 117.7(3) . . ?
C21 C20 C17 136.5(2) . . ?
C19 C20 C17 105.8(3) . . ?
C19 N2 C18 106.7(2) . . ?
C19 N2 C29 118.4(2) . . ?
C18 N2 C29 122.7(3) . . ?
C16 C11 C12 118.4(2) . . ?
C16 C11 C10 135.6(2) . . ?
C12 C11 C10 105.9(2) . . ?
C24 C19 N2 128.4(3) . . ?
C24 C19 C20 121.2(3) . . ?
N2 C19 C20 110.4(2) . . ?
C18 C17 C10 119.0(3) . . ?
C18 C17 C20 106.7(2) . . ?
C10 C17 C20 134.3(3) . . ?
C22 O2 C30 118.8(3) . . ?
C12 N3 C9 109.0(2) . . ?
C12 N3 C27 121.4(2) . . ?
C9 N3 C27 129.6(2) . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 H60 120.0 . . ?
C11 C16 H60 120.0 . . ?
C5 C6 N1 128.6(3) . . ?
C5 C6 C1 122.0(3) . . ?
N1 C6 C1 109.4(2) . . ?
N1 C7 C18 129.0(3) . . ?
N1 C7 C8 109.5(3) . . ?
C18 C7 C8 121.5(2) . . ?
C2 C1 C6 117.0(3) . . ?
C2 C1 C8 136.7(3) . . ?
C6 C1 C8 106.3(2) . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H54 119.4 . . ?
C22 C21 H54 119.4 . . ?
C15 O3 C28 118.5(2) . . ?
N3 C9 C10 108.4(2) . . ?
N3 C9 C8 130.1(2) . . ?
C10 C9 C8 121.5(2) . . ?
C7 C8 C9 117.0(3) . . ?
C7 C8 C1 106.2(2) . . ?
C9 C8 C1 136.8(3) . . ?
C7 N1 C6 108.6(2) . . ?
C7 N1 C25 127.0(3) . . ?
C6 N1 C25 120.0(3) . . ?
C7 C18 C17 120.8(2) . . ?
C7 C18 N2 128.9(3) . . ?
C17 C18 N2 110.2(2) . . ?
N3 C12 C13 129.1(3) . . ?
N3 C12 C11 109.6(2) . . ?
C13 C12 C11 121.3(3) . . ?
O3 C15 C16 124.9(3) . . ?
O3 C15 C14 115.0(3) . . ?
C16 C15 C14 120.1(3) . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H44 120.7 . . ?
C12 C13 H44 120.7 . . ?
O2 C22 C23 124.0(3) . . ?
O2 C22 C21 116.1(3) . . ?
C23 C22 C21 119.8(3) . . ?
C9 C10 C17 119.4(2) . . ?
C9 C10 C11 107.2(2) . . ?
C17 C10 C11 133.3(2) . . ?
C23 C24 C19 119.6(3) . . ?
C23 C24 H57 120.2 . . ?
C19 C24 H57 120.2 . . ?
C13 C14 C15 121.5(3) . . ?
C13 C14 H45 119.3 . . ?
C15 C14 H45 119.3 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H56 119.8 . . ?
C22 C23 H56 119.8 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H31 120.1 . . ?
C6 C5 H31 120.1 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H35 119.8 . . ?
C1 C2 H35 119.8 . . ?
N2 C29 H51A 109.5 . . ?
N2 C29 H51B 109.5 . . ?
H51A C29 H51B 109.5 . . ?
N2 C29 H51C 109.5 . . ?
H51A C29 H51C 109.5 . . ?
H51B C29 H51C 109.5 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H32 120.0 . . ?
C3 C4 H32 120.0 . . ?
C2 C3 O1 123.9(4) . . ?
C2 C3 C4 121.0(3) . . ?
O1 C3 C4 115.1(3) . . ?
N3 C27 H42A 109.5 . . ?
N3 C27 H42B 109.5 . . ?
H42A C27 H42B 109.5 . . ?
N3 C27 H42C 109.5 . . ?
H42A C27 H42C 109.5 . . ?
H42B C27 H42C 109.5 . . ?
C3 O1 C26 118.4(3) . . ?
N1 C25 H38A 109.5 . . ?
N1 C25 H38B 109.5 . . ?
H38A C25 H38B 109.5 . . ?
N1 C25 H38C 109.5 . . ?
H38A C25 H38C 109.5 . . ?
H38B C25 H38C 109.5 . . ?
O1 C26 H34A 109.5 . . ?
O1 C26 H34B 109.5 . . ?
H34A C26 H34B 109.5 . . ?
O1 C26 H34C 109.5 . . ?
H34A C26 H34C 109.5 . . ?
H34B C26 H34C 109.5 . . ?
O3 C28 H59A 109.5 . . ?
O3 C28 H59B 109.5 . . ?
H59A C28 H59B 109.5 . . ?
O3 C28 H59C 109.5 . . ?
H59A C28 H59C 109.5 . . ?
H59B C28 H59C 109.5 . . ?
O2 C30 H58A 109.5 . . ?
O2 C30 H58B 109.5 . . ?
H58A C30 H58B 109.5 . . ?
O2 C30 H58C 109.5 . . ?
H58A C30 H58C 109.5 . . ?
H58B C30 H58C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.034
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound-34
_database_code_depnum_ccdc_archive 'CCDC 1029451'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H39 N3 O3 S0'
_chemical_formula_weight         705.82

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'

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

_cell_length_a                   14.8372(17)
_cell_length_b                   26.503(3)
_cell_length_c                   18.224(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.420(11)
_cell_angle_gamma                90.00
_cell_volume                     7121.3(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2557
_cell_measurement_theta_min      2.8400
_cell_measurement_theta_max      26.6530

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2976
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.91782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  multi-scan
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13371
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6266
_reflns_number_gt                3882
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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)+(0.0462P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6266
_refine_ls_number_parameters     490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
N2 N 1.05328(11) 0.54093(7) 0.85546(9) 0.0413(5) Uani 1 1 d . . .
N1 N 0.75693(11) 0.53219(7) 0.93768(8) 0.0395(4) Uani 1 1 d . . .
C36 C 0.91951(14) 0.53869(8) 0.90636(10) 0.0371(5) Uani 1 1 d . . .
N3 N 0.91832(12) 0.38153(7) 0.89653(10) 0.0458(5) Uani 1 1 d . . .
C34 C 0.98743(14) 0.45654(8) 0.87911(10) 0.0374(5) Uani 1 1 d . . .
C31 C 0.83050(14) 0.46066(8) 0.91179(10) 0.0376(5) Uani 1 1 d . . .
C32 C 0.84052(13) 0.51289(8) 0.92281(10) 0.0358(5) Uani 1 1 d . . .
C35 C 0.98897(13) 0.50958(8) 0.88023(10) 0.0361(5) Uani 1 1 d . . .
C30 C 0.73597(14) 0.44893(8) 0.91314(10) 0.0378(5) Uani 1 1 d . . .
C37 C 1.02559(14) 0.59038(8) 0.86454(11) 0.0436(6) Uani 1 1 d . . .
C45 C 1.14137(14) 0.41379(9) 0.85210(11) 0.0455(6) Uani 1 1 d . . .
H45 H 1.1735 0.4430 0.8440 0.055 Uiso 1 1 calc R . .
C38 C 0.94408(14) 0.59093(8) 0.89677(11) 0.0404(5) Uani 1 1 d . . .
C25 C 0.68209(14) 0.40624(9) 0.89649(11) 0.0444(6) Uani 1 1 d . . .
H25 H 0.7081 0.3760 0.8837 0.053 Uiso 1 1 calc R . .
C33 C 0.90799(14) 0.43324(8) 0.89663(10) 0.0382(5) Uani 1 1 d . . .
C39 C 0.90477(15) 0.63763(8) 0.90743(12) 0.0501(6) Uani 1 1 d . . .
H39 H 0.8507 0.6396 0.9286 0.060 Uiso 1 1 calc R . .
C29 C 0.69375(14) 0.49367(8) 0.93014(10) 0.0394(5) Uani 1 1 d . . .
C43 C 1.00577(15) 0.37155(8) 0.88010(12) 0.0452(6) Uani 1 1 d . . .
C44 C 1.05114(14) 0.41659(8) 0.86746(10) 0.0394(5) Uani 1 1 d . . .
C19 C 1.11013(13) 0.52949(9) 0.79731(10) 0.0430(6) Uani 1 1 d . . .
H19A H 1.0909 0.5507 0.7550 0.052 Uiso 1 1 calc R . .
H19B H 1.0994 0.4947 0.7822 0.052 Uiso 1 1 calc R . .
C8 C 0.67458(14) 0.61388(8) 0.93827(12) 0.0437(6) Uani 1 1 d . . .
O1 O 0.53040(11) 0.37072(7) 0.88348(10) 0.0720(5) Uani 1 1 d . . .
O3 O 1.27060(11) 0.36030(7) 0.83563(9) 0.0690(5) Uani 1 1 d . . .
O2 O 0.91262(13) 0.72813(7) 0.89529(11) 0.0850(6) Uani 1 1 d . . .
C28 C 0.60095(14) 0.49628(9) 0.93488(11) 0.0478(6) Uani 1 1 d . . .
H28 H 0.5743 0.5261 0.9485 0.057 Uiso 1 1 calc R . .
C14 C 0.84039(15) 0.29975(9) 0.90507(14) 0.0521(6) Uani 1 1 d . . .
C46 C 1.18177(15) 0.36752(10) 0.84912(12) 0.0522(6) Uani 1 1 d . . .
C21 C 0.73909(14) 0.57702(8) 0.97893(11) 0.0459(6) Uani 1 1 d . . .
H21A H 0.7962 0.5941 0.9932 0.055 Uiso 1 1 calc R . .
H21B H 0.7146 0.5669 1.0238 0.055 Uiso 1 1 calc R . .
C40 C 0.94622(17) 0.68071(9) 0.88662(14) 0.0570(7) Uani 1 1 d . . .
C6 C 1.21069(14) 0.53666(9) 0.81742(11) 0.0424(6) Uani 1 1 d . . .
C5 C 1.24752(15) 0.55604(9) 0.88389(12) 0.0529(6) Uani 1 1 d . . .
H5 H 1.2105 0.5628 0.9206 0.064 Uiso 1 1 calc R . .
C41 C 1.02592(17) 0.67875(10) 0.85393(14) 0.0628(7) Uani 1 1 d . . .
H41 H 1.0523 0.7085 0.8396 0.075 Uiso 1 1 calc R . .
C7 C 0.67047(16) 0.61999(9) 0.86306(13) 0.0564(6) Uani 1 1 d . . .
H7 H 0.7089 0.6015 0.8364 0.068 Uiso 1 1 calc R . .
C42 C 1.06601(16) 0.63374(9) 0.84258(13) 0.0547(6) Uani 1 1 d . . .
H42 H 1.1195 0.6323 0.8205 0.066 Uiso 1 1 calc R . .
C22 C 1.31647(16) 0.40178(11) 0.80932(14) 0.0711(8) Uani 1 1 d . . .
H22A H 1.3220 0.4279 0.8460 0.107 Uiso 1 1 calc R . .
H22B H 1.2830 0.4143 0.7649 0.107 Uiso 1 1 calc R . .
H22C H 1.3758 0.3915 0.7990 0.107 Uiso 1 1 calc R . .
C47 C 1.13607(17) 0.32371(10) 0.86249(14) 0.0637(7) Uani 1 1 d . . .
H47 H 1.1652 0.2927 0.8607 0.076 Uiso 1 1 calc R . .
C27 C 0.55002(16) 0.45394(9) 0.91903(12) 0.0541(6) Uani 1 1 d . . .
H27 H 0.4878 0.4549 0.9215 0.065 Uiso 1 1 calc R . .
C26 C 0.59016(15) 0.40961(9) 0.89933(12) 0.0487(6) Uani 1 1 d . . .
C1 C 1.26811(16) 0.52553(10) 0.76522(12) 0.0586(7) Uani 1 1 d . . .
H1 H 1.2443 0.5117 0.7203 0.070 Uiso 1 1 calc R . .
C4 C 1.33956(17) 0.56553(11) 0.89644(14) 0.0651(7) Uani 1 1 d . . .
H4 H 1.3639 0.5791 0.9414 0.078 Uiso 1 1 calc R . .
C48 C 1.04801(17) 0.32564(9) 0.87848(13) 0.0608(7) Uani 1 1 d . . .
H48 H 1.0173 0.2962 0.8881 0.073 Uiso 1 1 calc R . .
C20 C 0.87510(15) 0.34703(8) 0.94348(12) 0.0496(6) Uani 1 1 d . . .
H20A H 0.8249 0.3642 0.9625 0.060 Uiso 1 1 calc R . .
H20B H 0.9184 0.3380 0.9853 0.060 Uiso 1 1 calc R . .
C3 C 1.39504(17) 0.55522(11) 0.84349(16) 0.0735(8) Uani 1 1 d . . .
H3 H 1.4567 0.5624 0.8520 0.088 Uiso 1 1 calc R . .
C2 C 1.36016(17) 0.53438(11) 0.77810(15) 0.0734(8) Uani 1 1 d . . .
H2 H 1.3980 0.5262 0.7425 0.088 Uiso 1 1 calc R . .
C9 C 0.61751(18) 0.64170(10) 0.97611(14) 0.0659(7) Uani 1 1 d . . .
H9 H 0.6194 0.6378 1.0270 0.079 Uiso 1 1 calc R . .
C13 C 0.81136(19) 0.29855(11) 0.83124(16) 0.0745(8) Uani 1 1 d . . .
H13 H 0.8136 0.3277 0.8030 0.089 Uiso 1 1 calc R . .
C12 C 0.60951(19) 0.65355(11) 0.82696(15) 0.0697(8) Uani 1 1 d . . .
H12 H 0.6068 0.6574 0.7760 0.084 Uiso 1 1 calc R . .
C24 C 0.83083(18) 0.73321(10) 0.92631(16) 0.0833(9) Uani 1 1 d . . .
H24A H 0.8375 0.7192 0.9752 0.125 Uiso 1 1 calc R . .
H24B H 0.7836 0.7156 0.8963 0.125 Uiso 1 1 calc R . .
H24C H 0.8154 0.7683 0.9287 0.125 Uiso 1 1 calc R . .
C15 C 0.8370(2) 0.25624(11) 0.94509(17) 0.0800(9) Uani 1 1 d . . .
H15 H 0.8570 0.2563 0.9953 0.096 Uiso 1 1 calc R . .
C23 C 0.56480(19) 0.32466(10) 0.86148(17) 0.0878(9) Uani 1 1 d . . .
H23A H 0.6099 0.3126 0.8992 0.132 Uiso 1 1 calc R . .
H23B H 0.5916 0.3293 0.8164 0.132 Uiso 1 1 calc R . .
H23C H 0.5164 0.3005 0.8537 0.132 Uiso 1 1 calc R . .
C11 C 0.5531(2) 0.68108(11) 0.86603(19) 0.0816(9) Uani 1 1 d . . .
H11 H 0.5121 0.7037 0.8417 0.098 Uiso 1 1 calc R . .
C17 C 0.7769(3) 0.21147(16) 0.8392(3) 0.1235(17) Uani 1 1 d . . .
H17 H 0.7565 0.1814 0.8169 0.148 Uiso 1 1 calc R . .
C10 C 0.5572(2) 0.67539(12) 0.94019(19) 0.0874(10) Uani 1 1 d . . .
H10 H 0.5193 0.6943 0.9669 0.105 Uiso 1 1 calc R . .
C18 C 0.7786(2) 0.25416(16) 0.7983(2) 0.1051(12) Uani 1 1 d . . .
H18 H 0.7579 0.2536 0.7482 0.126 Uiso 1 1 calc R . .
C16 C 0.8045(3) 0.21260(13) 0.9119(3) 0.1181(15) Uani 1 1 d . . .
H16 H 0.8015 0.1834 0.9399 0.142 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
N2 C35 1.379(2) . ?
N2 C37 1.389(3) . ?
N2 C19 1.458(2) . ?
N1 C29 1.382(3) . ?
N1 C32 1.396(2) . ?
N1 C21 1.446(2) . ?
C36 C35 1.412(3) . ?
C36 C32 1.418(3) . ?
C36 C38 1.447(3) . ?
N3 C33 1.379(3) . ?
N3 C43 1.389(3) . ?
N3 C20 1.450(3) . ?
C34 C33 1.399(3) . ?
C34 C35 1.406(3) . ?
C34 C44 1.451(3) . ?
C31 C32 1.404(3) . ?
C31 C33 1.413(3) . ?
C31 C30 1.440(3) . ?
C30 C29 1.392(3) . ?
C30 C25 1.399(3) . ?
C37 C42 1.376(3) . ?
C37 C38 1.403(3) . ?
C45 C46 1.369(3) . ?
C45 C44 1.400(3) . ?
C45 H45 0.9300 . ?
C38 C39 1.391(3) . ?
C25 C26 1.374(3) . ?
C25 H25 0.9300 . ?
C39 C40 1.370(3) . ?
C39 H39 0.9300 . ?
C29 C28 1.391(3) . ?
C43 C48 1.370(3) . ?
C43 C44 1.402(3) . ?
C19 C6 1.508(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C8 C9 1.366(3) . ?
C8 C7 1.375(3) . ?
C8 C21 1.504(3) . ?
O1 C26 1.369(3) . ?
O1 C23 1.399(3) . ?
O3 C46 1.381(3) . ?
O3 C22 1.405(3) . ?
O2 C40 1.368(3) . ?
O2 C24 1.401(3) . ?
C28 C27 1.365(3) . ?
C28 H28 0.9300 . ?
C14 C13 1.366(3) . ?
C14 C15 1.369(3) . ?
C14 C20 1.498(3) . ?
C46 C47 1.380(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C40 C41 1.383(3) . ?
C6 C5 1.372(3) . ?
C6 C1 1.378(3) . ?
C5 C4 1.382(3) . ?
C5 H5 0.9300 . ?
C41 C42 1.359(3) . ?
C41 H41 0.9300 . ?
C7 C12 1.382(3) . ?
C7 H7 0.9300 . ?
C42 H42 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C47 C48 1.371(3) . ?
C47 H47 0.9300 . ?
C27 C26 1.383(3) . ?
C27 H27 0.9300 . ?
C1 C2 1.380(3) . ?
C1 H1 0.9300 . ?
C4 C3 1.364(3) . ?
C4 H4 0.9300 . ?
C48 H48 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C3 C2 1.362(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C13 C18 1.384(4) . ?
C13 H13 0.9300 . ?
C12 C11 1.368(4) . ?
C12 H12 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C15 C16 1.368(4) . ?
C15 H15 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C11 C10 1.354(4) . ?
C11 H11 0.9300 . ?
C17 C16 1.342(5) . ?
C17 C18 1.357(5) . ?
C17 H17 0.9300 . ?
C10 H10 0.9300 . ?
C18 H18 0.9300 . ?
C16 H16 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
C35 N2 C37 107.75(17) . . ?
C35 N2 C19 126.19(17) . . ?
C37 N2 C19 119.05(18) . . ?
C29 N1 C32 108.51(17) . . ?
C29 N1 C21 119.79(17) . . ?
C32 N1 C21 128.34(18) . . ?
C35 C36 C32 117.36(19) . . ?
C35 C36 C38 106.18(18) . . ?
C32 C36 C38 135.4(2) . . ?
C33 N3 C43 107.23(18) . . ?
C33 N3 C20 124.70(18) . . ?
C43 N3 C20 119.51(17) . . ?
C33 C34 C35 116.8(2) . . ?
C33 C34 C44 106.91(19) . . ?
C35 C34 C44 136.2(2) . . ?
C32 C31 C33 117.36(19) . . ?
C32 C31 C30 107.35(19) . . ?
C33 C31 C30 135.0(2) . . ?
N1 C32 C31 107.88(18) . . ?
N1 C32 C36 129.6(2) . . ?
C31 C32 C36 121.47(19) . . ?
N2 C35 C34 127.5(2) . . ?
N2 C35 C36 109.82(19) . . ?
C34 C35 C36 122.68(19) . . ?
C29 C30 C25 118.47(19) . . ?
C29 C30 C31 106.45(19) . . ?
C25 C30 C31 134.9(2) . . ?
C42 C37 N2 127.5(2) . . ?
C42 C37 C38 122.5(2) . . ?
N2 C37 C38 109.89(19) . . ?
C46 C45 C44 119.2(2) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C39 C38 C37 117.5(2) . . ?
C39 C38 C36 136.0(2) . . ?
C37 C38 C36 106.33(19) . . ?
C26 C25 C30 119.0(2) . . ?
C26 C25 H25 120.5 . . ?
C30 C25 H25 120.5 . . ?
N3 C33 C34 109.98(19) . . ?
N3 C33 C31 127.2(2) . . ?
C34 C33 C31 122.8(2) . . ?
C40 C39 C38 119.6(2) . . ?
C40 C39 H39 120.2 . . ?
C38 C39 H39 120.2 . . ?
N1 C29 C28 128.5(2) . . ?
N1 C29 C30 109.53(18) . . ?
C28 C29 C30 122.0(2) . . ?
C48 C43 N3 127.9(2) . . ?
C48 C43 C44 121.5(2) . . ?
N3 C43 C44 110.52(19) . . ?
C45 C44 C43 118.4(2) . . ?
C45 C44 C34 136.2(2) . . ?
C43 C44 C34 105.34(18) . . ?
N2 C19 C6 115.73(16) . . ?
N2 C19 H19A 108.3 . . ?
C6 C19 H19A 108.3 . . ?
N2 C19 H19B 108.3 . . ?
C6 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C9 C8 C7 118.6(2) . . ?
C9 C8 C21 119.9(2) . . ?
C7 C8 C21 121.5(2) . . ?
C26 O1 C23 117.96(19) . . ?
C46 O3 C22 117.44(19) . . ?
C40 O2 C24 118.6(2) . . ?
C27 C28 C29 118.3(2) . . ?
C27 C28 H28 120.8 . . ?
C29 C28 H28 120.8 . . ?
C13 C14 C15 118.6(3) . . ?
C13 C14 C20 122.2(2) . . ?
C15 C14 C20 119.1(2) . . ?
C45 C46 C47 121.4(2) . . ?
C45 C46 O3 124.2(2) . . ?
C47 C46 O3 114.4(2) . . ?
N1 C21 C8 114.90(17) . . ?
N1 C21 H21A 108.5 . . ?
C8 C21 H21A 108.5 . . ?
N1 C21 H21B 108.5 . . ?
C8 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
O2 C40 C39 123.6(2) . . ?
O2 C40 C41 115.1(2) . . ?
C39 C40 C41 121.3(2) . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C19 123.2(2) . . ?
C1 C6 C19 118.46(19) . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C42 C41 C40 120.6(2) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C8 C7 C12 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C12 C7 H7 119.9 . . ?
C41 C42 C37 118.4(2) . . ?
C41 C42 H42 120.8 . . ?
C37 C42 H42 120.8 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C48 C47 C46 120.3(2) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C28 C27 C26 120.6(2) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
O1 C26 C25 124.4(2) . . ?
O1 C26 C27 114.0(2) . . ?
C25 C26 C27 121.6(2) . . ?
C6 C1 C2 121.5(2) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C43 C48 C47 119.1(2) . . ?
C43 C48 H48 120.4 . . ?
C47 C48 H48 120.4 . . ?
N3 C20 C14 113.78(18) . . ?
N3 C20 H20A 108.8 . . ?
C14 C20 H20A 108.8 . . ?
N3 C20 H20B 108.8 . . ?
C14 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C14 C13 C18 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C18 C13 H13 119.9 . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C16 C17 C18 120.1(4) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C17 C18 C13 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C17 C16 C15 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound-A
_database_code_depnum_ccdc_archive 'CCDC 1029452'
_audit_update_record             
;
2014-10-16 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2'
_chemical_formula_weight         182.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   9.0822(11)
_cell_length_b                   14.3844(18)
_cell_length_c                   7.6234(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.165(2)
_cell_angle_gamma                90.00
_cell_volume                     995.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  none
_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            9419
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1750
_reflns_number_gt                1437
_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 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)+(0.0675P)²+0.1375P] 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     SHELXL
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1750
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1329
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.66846(14) 0.57774(9) 0.02874(19) 0.0686(4) Uani 1 1 d . . .
C7 C 0.82303(16) 0.48120(11) -0.1045(2) 0.0603(4) Uani 1 1 d . . .
C6 C 0.78175(15) 0.43856(11) 0.05694(19) 0.0579(4) Uani 1 1 d . . .
C10 C 0.91719(18) 0.44894(12) -0.2390(2) 0.0661(5) Uani 1 1 d . . .
H10 H 0.9224 0.4866 -0.3377 0.079 Uiso 1 1 calc R . .
C8 C 0.75080(18) 0.56517(12) -0.1133(2) 0.0692(5) Uani 1 1 d . . .
H8 H 0.7577 0.6076 -0.2047 0.083 Uiso 1 1 calc R . .
C5 C 0.81367(19) 0.35538(12) 0.1438(2) 0.0704(5) Uani 1 1 d . . .
H5 H 0.8795 0.3134 0.0973 0.084 Uiso 1 1 calc R . .
C1 C 0.68406(16) 0.50065(11) 0.1356(2) 0.0627(4) Uani 1 1 d . . .
C11 C 0.99737(18) 0.37217(12) -0.2394(2) 0.0665(5) Uani 1 1 d . . .
H11 H 0.9966 0.3331 -0.1422 0.080 Uiso 1 1 calc R . .
C9 C 0.5784(2) 0.65907(13) 0.0642(3) 0.0877(6) Uani 1 1 d . . .
H9A H 0.6244 0.6946 0.1576 0.132 Uiso 1 1 calc R . .
H9B H 0.4825 0.6394 0.0977 0.132 Uiso 1 1 calc R . .
H9C H 0.5691 0.6968 -0.0396 0.132 Uiso 1 1 calc R . .
C2 C 0.6193(2) 0.48128(14) 0.2935(3) 0.0837(6) Uani 1 1 d . . .
H2 H 0.5560 0.5235 0.3441 0.100 Uiso 1 1 calc R . .
C4 C 0.7476(2) 0.33580(15) 0.2980(2) 0.0901(6) Uani 1 1 d . . .
H4 H 0.7676 0.2795 0.3541 0.108 Uiso 1 1 calc R . .
C3 C 0.6518(3) 0.39791(16) 0.3721(3) 0.0992(7) Uani 1 1 d . . .
H3 H 0.6087 0.3827 0.4771 0.119 Uiso 1 1 calc R . .
C12 C 1.0846(2) 0.34715(12) -0.3830(2) 0.0707(5) Uani 1 1 d . . .
N2 N 1.1540(2) 0.32425(12) -0.4963(2) 0.0948(6) 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 C8 1.351(2) . ?
N1 C1 1.380(2) . ?
N1 C9 1.458(2) . ?
C7 C8 1.375(2) . ?
C7 C10 1.437(2) . ?
C7 C6 1.437(2) . ?
C6 C5 1.393(2) . ?
C6 C1 1.409(2) . ?
C10 C11 1.323(2) . ?
C5 C4 1.369(2) . ?
C1 C2 1.388(2) . ?
C11 C12 1.422(2) . ?
C2 C3 1.368(3) . ?
C4 C3 1.383(3) . ?
C12 N2 1.137(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
C8 N1 C1 108.53(13) . . ?
C8 N1 C9 125.94(15) . . ?
C1 N1 C9 125.53(15) . . ?
C8 C7 C10 123.00(16) . . ?
C8 C7 C6 106.10(14) . . ?
C10 C7 C6 130.89(15) . . ?
C5 C6 C1 117.73(15) . . ?
C5 C6 C7 135.84(14) . . ?
C1 C6 C7 106.42(14) . . ?
C11 C10 C7 127.89(16) . . ?
N1 C8 C7 110.85(15) . . ?
C4 C5 C6 119.68(16) . . ?
N1 C1 C2 129.48(15) . . ?
N1 C1 C6 108.09(14) . . ?
C2 C1 C6 122.42(16) . . ?
C10 C11 C12 122.43(16) . . ?
C3 C2 C1 117.68(17) . . ?
C5 C4 C3 121.38(19) . . ?
C2 C3 C4 121.09(18) . . ?
N2 C12 C11 177.81(19) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.027






