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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 I N3 O'
_chemical_formula_sum            'C16 H10 I N3 O'
_chemical_formula_weight         387.17

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'
I I -0.4742 1.8119 '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/n 1'

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

_cell_length_a                   13.0741(18)
_cell_length_b                   4.2988(4)
_cell_length_c                   24.974(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.040(11)
_cell_angle_gamma                90.00
_cell_volume                     1382.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1288
_cell_measurement_theta_min      3.3180
_cell_measurement_theta_max      28.3750

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            ORENGE
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2585
_exptl_absorpt_correction_T_max  0.6542
_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
_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  '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            3560
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2512
_reflns_number_gt                1998
_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)+(0.0965P)²+0.7793P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2512
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.007

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
I1 I 0.64261(4) 0.73281(9) 0.159004(16) 0.0319(2) Uani 1 1 d . . .
N2 N 0.3635(5) 0.3040(13) 0.1883(2) 0.0324(14) Uani 1 1 d . . .
H2 H 0.3209 0.2525 0.2095 0.039 Uiso 1 1 calc R . .
N3 N 0.4915(4) 0.5411(12) 0.25859(18) 0.0271(12) Uani 1 1 d . . .
C4 C 0.5893(7) 0.7178(14) 0.3590(3) 0.0327(17) Uani 1 1 d . . .
C5 C 0.4877(6) 0.8127(14) 0.3416(3) 0.0284(15) Uani 1 1 d . . .
C6 C 0.5923(5) 0.4437(16) 0.2807(2) 0.0310(15) Uani 1 1 d . . .
H6 H 0.6258 0.3118 0.2598 0.037 Uiso 1 1 calc R . .
C7 C 0.5026(5) 0.5082(14) 0.1602(2) 0.0278(14) Uani 1 1 d . . .
O8 O 0.3410(5) 0.7691(11) 0.2708(2) 0.0429(14) Uani 1 1 d . . .
N9 N 0.6412(4) 0.5232(13) 0.32739(19) 0.0300(12) Uani 1 1 d . . .
C10 C 0.4313(6) 0.7117(13) 0.2891(3) 0.0275(14) Uani 1 1 d . . .
C11 C 0.3709(8) 0.160(2) 0.0273(3) 0.050(2) Uani 1 1 d . . .
H11 H 0.3766 0.1262 -0.0089 0.060 Uiso 1 1 calc R . .
C12 C 0.6445(7) 0.8231(17) 0.4096(3) 0.0398(18) Uani 1 1 d . . .
H12 H 0.7132 0.7639 0.4212 0.048 Uiso 1 1 calc R . .
C13 C 0.4387(5) 0.3653(15) 0.1149(3) 0.0297(15) Uani 1 1 d . . .
C14 C 0.4396(6) 1.0025(16) 0.3754(3) 0.0389(17) Uani 1 1 d . . .
H14 H 0.3706 1.0611 0.3645 0.047 Uiso 1 1 calc R . .
C15 C 0.4472(7) 0.3211(17) 0.0601(3) 0.0391(18) Uani 1 1 d . . .
H15 H 0.5037 0.4004 0.0464 0.047 Uiso 1 1 calc R . .
C16 C 0.2857(7) 0.0446(18) 0.0463(3) 0.049(2) Uani 1 1 d . . .
H16 H 0.2345 -0.0591 0.0224 0.059 Uiso 1 1 calc R . .
C17 C 0.4932(7) 1.1023(19) 0.4241(3) 0.0455(19) Uani 1 1 d . . .
H17 H 0.4610 1.2313 0.4461 0.055 Uiso 1 1 calc R . .
C18 C 0.4551(5) 0.4620(14) 0.2033(2) 0.0246(13) Uani 1 1 d . . .
C19 C 0.3518(6) 0.2426(13) 0.1336(3) 0.0289(16) Uani 1 1 d . . .
C20 C 0.2742(6) 0.0787(16) 0.0998(3) 0.0386(17) Uani 1 1 d . . .
H20 H 0.2173 -0.0037 0.1127 0.046 Uiso 1 1 calc R . .
C21 C 0.5963(7) 1.0109(17) 0.4412(3) 0.047(2) Uani 1 1 d . . .
H21 H 0.6323 1.0796 0.4745 0.057 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
I1 C7 2.074(7) . ?
N2 C19 1.375(8) . ?
N2 C18 1.371(9) . ?
N2 H2 0.8600 . ?
N3 C10 1.396(8) . ?
N3 C6 1.400(7) . ?
N3 C18 1.422(7) . ?
C4 C12 1.417(10) . ?
C4 C5 1.385(11) . ?
C4 N9 1.404(9) . ?
C5 C14 1.398(9) . ?
C5 C10 1.455(10) . ?
C6 N9 1.275(7) . ?
C6 H6 0.9300 . ?
C7 C18 1.348(9) . ?
C7 C13 1.423(8) . ?
O8 C10 1.215(9) . ?
C11 C15 1.365(12) . ?
C11 C16 1.377(12) . ?
C11 H11 0.9300 . ?
C12 C21 1.358(11) . ?
C12 H12 0.9300 . ?
C13 C19 1.405(10) . ?
C13 C15 1.406(10) . ?
C14 C17 1.364(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C20 1.378(10) . ?
C16 H16 0.9300 . ?
C17 C21 1.398(11) . ?
C17 H17 0.9300 . ?
C19 C20 1.392(9) . ?
C20 H20 0.9300 . ?
C21 H21 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
C19 N2 C18 107.8(6) . . ?
C19 N2 H2 126.1 . . ?
C18 N2 H2 126.1 . . ?
C10 N3 C6 121.5(5) . . ?
C10 N3 C18 122.1(5) . . ?
C6 N3 C18 116.4(5) . . ?
C12 C4 C5 119.8(7) . . ?
C12 C4 N9 118.1(8) . . ?
C5 C4 N9 122.1(6) . . ?
C4 C5 C14 119.4(6) . . ?
C4 C5 C10 120.1(6) . . ?
C14 C5 C10 120.5(7) . . ?
N9 C6 N3 124.6(6) . . ?
N9 C6 H6 117.7 . . ?
N3 C6 H6 117.7 . . ?
C18 C7 C13 106.4(6) . . ?
C18 C7 I1 127.6(5) . . ?
C13 C7 I1 125.9(5) . . ?
C6 N9 C4 117.3(6) . . ?
O8 C10 N3 120.3(6) . . ?
O8 C10 C5 125.8(6) . . ?
N3 C10 C5 113.8(6) . . ?
C15 C11 C16 121.7(8) . . ?
C15 C11 H11 119.1 . . ?
C16 C11 H11 119.1 . . ?
C21 C12 C4 119.5(8) . . ?
C21 C12 H12 120.3 . . ?
C4 C12 H12 120.3 . . ?
C19 C13 C15 118.6(6) . . ?
C19 C13 C7 107.2(6) . . ?
C15 C13 C7 134.2(7) . . ?
C17 C14 C5 120.4(7) . . ?
C17 C14 H14 119.8 . . ?
C5 C14 H14 119.8 . . ?
C11 C15 C13 118.6(8) . . ?
C11 C15 H15 120.7 . . ?
C13 C15 H15 120.7 . . ?
C20 C16 C11 121.9(7) . . ?
C20 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
C14 C17 C21 120.1(7) . . ?
C14 C17 H17 120.0 . . ?
C21 C17 H17 120.0 . . ?
C7 C18 N2 111.0(5) . . ?
C7 C18 N3 128.1(6) . . ?
N2 C18 N3 120.8(6) . . ?
N2 C19 C13 107.6(6) . . ?
N2 C19 C20 130.0(7) . . ?
C13 C19 C20 122.3(7) . . ?
C16 C20 C19 116.7(7) . . ?
C16 C20 H20 121.6 . . ?
C19 C20 H20 121.6 . . ?
C12 C21 C17 120.7(7) . . ?
C12 C21 H21 119.6 . . ?
C17 C21 H21 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.887
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.887
_refine_diff_density_max         1.004
_refine_diff_density_min         -1.600
_refine_diff_density_rms         0.194
_database_code_depnum_ccdc_archive 'CCDC 956409'
#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.33

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           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

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

_cell_length_a                   8.3989(18)
_cell_length_b                   12.9656(14)
_cell_length_c                   13.6993(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.702(16)
_cell_angle_gamma                90.00
_cell_volume                     1460.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1992
_cell_measurement_theta_min      3.4410
_cell_measurement_theta_max      28.0280

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9357
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298
_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  '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            5857
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         26.36
_reflns_number_total             2989
_reflns_number_gt                2219
_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)+(0.0776P)²+0.8925P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2989
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.2100
_refine_ls_wR_factor_gt          0.1994
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.003
_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 0.1733(3) 0.55781(15) 0.25125(15) 0.0526(6) Uani 1 1 d . . .
N2 N 0.1478(3) 0.37418(19) 0.39609(18) 0.0451(6) Uani 1 1 d . . .
N3 N 0.2643(3) 0.39201(17) 0.24674(17) 0.0388(6) Uani 1 1 d . . .
C4 C 0.2796(3) 0.3795(2) 0.3508(2) 0.0368(6) Uani 1 1 d . . .
C5 C 0.3800(4) 0.3648(2) 0.5128(2) 0.0393(6) Uani 1 1 d . . .
C6 C 0.2088(4) 0.3657(2) 0.4974(2) 0.0400(7) Uani 1 1 d . . .
C7 C 0.2317(4) 0.4952(2) 0.0989(2) 0.0405(7) Uani 1 1 d . . .
N8 N 0.3227(4) 0.31511(19) 0.10100(19) 0.0508(7) Uani 1 1 d . . .
C9 C 0.4229(3) 0.3730(2) 0.4186(2) 0.0362(6) Uani 1 1 d . . .
C10 C 0.2184(3) 0.4886(2) 0.2029(2) 0.0390(6) Uani 1 1 d . . .
C11 C 0.1310(5) 0.3583(2) 0.5777(2) 0.0547(8) Uani 1 1 d . . .
H11 H 0.0182 0.3572 0.5677 0.066 Uiso 1 1 calc R . .
C12 C 0.4741(4) 0.3593(2) 0.6096(2) 0.0522(8) Uani 1 1 d . . .
H12 H 0.5871 0.3589 0.6207 0.063 Uiso 1 1 calc R . .
C13 C -0.0234(4) 0.3789(3) 0.3471(3) 0.0541(8) Uani 1 1 d . . .
H13A H -0.0674 0.4448 0.3597 0.081 Uiso 1 1 calc R . .
H13B H -0.0823 0.3253 0.3727 0.081 Uiso 1 1 calc R . .
H13C H -0.0333 0.3698 0.2765 0.081 Uiso 1 1 calc R . .
C14 C 0.3096(4) 0.3114(2) 0.1919(2) 0.0452(7) Uani 1 1 d . . .
H14 H 0.3325 0.2486 0.2246 0.054 Uiso 1 1 calc R . .
C15 C 0.3039(5) 0.4190(3) -0.0461(2) 0.0584(9) Uani 1 1 d . . .
H15 H 0.3389 0.3627 -0.0782 0.070 Uiso 1 1 calc R . .
C16 C 0.2859(4) 0.4097(2) 0.0525(2) 0.0429(7) Uani 1 1 d . . .
C17 C 0.5899(4) 0.3715(3) 0.3993(3) 0.0542(8) Uani 1 1 d . . .
H17A H 0.6298 0.3020 0.4036 0.081 Uiso 1 1 calc R . .
H17B H 0.6594 0.4134 0.4480 0.081 Uiso 1 1 calc R . .
H17C H 0.5889 0.3983 0.3339 0.081 Uiso 1 1 calc R . .
C18 C 0.1950(5) 0.5875(2) 0.0463(2) 0.0558(9) Uani 1 1 d . . .
H18 H 0.1567 0.6439 0.0766 0.067 Uiso 1 1 calc R . .
C19 C 0.2246(6) 0.3527(3) 0.6712(3) 0.0647(10) Uani 1 1 d . . .
H19 H 0.1741 0.3476 0.7255 0.078 Uiso 1 1 calc R . .
C20 C 0.3938(6) 0.3544(3) 0.6878(2) 0.0632(10) Uani 1 1 d . . .
H20 H 0.4536 0.3522 0.7528 0.076 Uiso 1 1 calc R . .
C21 C 0.2159(5) 0.5946(3) -0.0501(2) 0.0668(11) Uani 1 1 d . . .
H21 H 0.1932 0.6562 -0.0848 0.080 Uiso 1 1 calc R . .
C22 C 0.2706(5) 0.5103(3) -0.0962(2) 0.0639(10) Uani 1 1 d . . .
H22 H 0.2848 0.5159 -0.1616 0.077 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
O1 C10 1.220(3) . ?
N2 C4 1.376(4) . ?
N2 C6 1.383(4) . ?
N2 C13 1.460(4) . ?
N3 C14 1.385(3) . ?
N3 C10 1.408(3) . ?
N3 C4 1.414(3) . ?
C4 C9 1.366(4) . ?
C5 C12 1.401(4) . ?
C5 C6 1.410(4) . ?
C5 C9 1.413(4) . ?
C6 C11 1.392(4) . ?
C7 C18 1.399(4) . ?
C7 C16 1.399(4) . ?
C7 C10 1.455(4) . ?
N8 C14 1.273(4) . ?
N8 C16 1.399(4) . ?
C9 C17 1.479(4) . ?
C11 C19 1.362(5) . ?
C11 H11 0.9300 . ?
C12 C20 1.378(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C15 C22 1.368(5) . ?
C15 C16 1.395(4) . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C21 1.369(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.386(5) . ?
C21 H21 0.9300 . ?
C22 H22 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
C4 N2 C6 106.8(2) . . ?
C4 N2 C13 126.7(3) . . ?
C6 N2 C13 126.5(3) . . ?
C14 N3 C10 121.5(2) . . ?
C14 N3 C4 118.8(2) . . ?
C10 N3 C4 119.5(2) . . ?
C9 C4 N2 111.6(2) . . ?
C9 C4 N3 125.4(2) . . ?
N2 C4 N3 122.9(2) . . ?
C12 C5 C6 120.3(3) . . ?
C12 C5 C9 132.0(3) . . ?
C6 C5 C9 107.7(2) . . ?
N2 C6 C11 131.4(3) . . ?
N2 C6 C5 108.0(2) . . ?
C11 C6 C5 120.6(3) . . ?
C18 C7 C16 120.1(3) . . ?
C18 C7 C10 120.2(3) . . ?
C16 C7 C10 119.7(2) . . ?
C14 N8 C16 116.3(2) . . ?
C4 C9 C5 105.8(2) . . ?
C4 C9 C17 128.0(3) . . ?
C5 C9 C17 126.1(3) . . ?
O1 C10 N3 120.7(3) . . ?
O1 C10 C7 125.6(2) . . ?
N3 C10 C7 113.6(2) . . ?
C19 C11 C6 118.2(3) . . ?
C19 C11 H11 120.9 . . ?
C6 C11 H11 120.9 . . ?
C20 C12 C5 117.8(3) . . ?
C20 C12 H12 121.1 . . ?
C5 C12 H12 121.1 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N8 C14 N3 126.1(3) . . ?
N8 C14 H14 117.0 . . ?
N3 C14 H14 117.0 . . ?
C22 C15 C16 120.6(3) . . ?
C22 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 N8 118.6(3) . . ?
C15 C16 C7 118.7(3) . . ?
N8 C16 C7 122.7(3) . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C18 C7 119.7(3) . . ?
C21 C18 H18 120.1 . . ?
C7 C18 H18 120.1 . . ?
C11 C19 C20 121.8(3) . . ?
C11 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C12 C20 C19 121.2(3) . . ?
C12 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C18 C21 C22 120.4(3) . . ?
C18 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C15 C22 C21 120.4(3) . . ?
C15 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 956410'
#######################################################################
#
#                 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_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N2 O'
_chemical_formula_sum            'C18 H16 N2 O'
_chemical_formula_weight         276.33

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                   10.8278(7)
_cell_length_b                   11.3669(8)
_cell_length_c                   13.0687(6)
_cell_angle_alpha                100.716(5)
_cell_angle_beta                 106.227(5)
_cell_angle_gamma                104.477(6)
_cell_volume                     1437.64(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    3448
_cell_measurement_theta_min      3.0870
_cell_measurement_theta_max      28.9860

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            PINK
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9385
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298
_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  '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            10424
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5875
_reflns_number_gt                4158
_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)+(0.0641P)²+0.1612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5875
_refine_ls_number_parameters     385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.005

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 0.73758(12) 0.63004(10) 0.14932(9) 0.0424(3) Uani 1 1 d . . .
H1 H 0.6878 0.6445 0.0965 0.064 Uiso 1 1 calc R . .
O2 O 0.99155(13) 0.79892(12) 0.18922(9) 0.0479(3) Uani 1 1 d . . .
H2 H 0.9195 0.7413 0.1686 0.072 Uiso 1 1 calc R . .
N2 N 0.48856(13) 0.34928(12) 0.01885(10) 0.0380(3) Uani 1 1 d . . .
N1 N 0.50067(14) 0.45854(13) 0.19338(10) 0.0392(3) Uani 1 1 d . . .
C32 C 0.58324(16) 0.34377(15) -0.03790(12) 0.0356(4) Uani 1 1 d . . .
C8 C 1.04093(17) 0.79411(15) 0.38330(13) 0.0374(4) Uani 1 1 d . . .
C29 C 0.55681(16) 0.43153(15) 0.11401(12) 0.0350(4) Uani 1 1 d . . .
C9 C 0.89832(17) 0.90523(15) 0.31971(13) 0.0398(4) Uani 1 1 d . . .
N4 N 0.86353(15) 0.87023(13) 0.39863(11) 0.0430(3) Uani 1 1 d . . .
C3 C 0.94995(17) 0.80132(15) 0.43918(13) 0.0387(4) Uani 1 1 d . . .
C18 C 1.01953(17) 0.86903(15) 0.29974(13) 0.0391(4) Uani 1 1 d . . .
C31 C 0.71089(16) 0.42930(15) 0.02259(13) 0.0378(4) Uani 1 1 d . . .
N3 N 0.83283(15) 0.97091(13) 0.25741(11) 0.0467(4) Uani 1 1 d . . .
C30 C 0.70711(16) 0.49638(15) 0.13182(13) 0.0375(4) Uani 1 1 d . . .
C27 C 0.47678(19) 0.56163(17) 0.34839(13) 0.0465(4) Uani 1 1 d . . .
C26 C 0.56213(19) 0.55930(17) 0.29145(13) 0.0448(4) Uani 1 1 d . . .
H26 H 0.6494 0.6160 0.3134 0.054 Uiso 1 1 calc R . .
C33 C 0.55699(19) 0.26434(16) -0.13985(13) 0.0443(4) Uani 1 1 d . . .
H33 H 0.4709 0.2071 -0.1804 0.053 Uiso 1 1 calc R . .
C25 C 0.36910(17) 0.39571(16) 0.18994(13) 0.0410(4) Uani 1 1 d . . .
C11 C 0.73010(19) 1.01909(16) 0.27409(16) 0.0507(5) Uani 1 1 d . . .
C7 C 1.12930(19) 0.72783(17) 0.40962(14) 0.0453(4) Uani 1 1 d . . .
H7 H 1.1902 0.7228 0.3722 0.054 Uiso 1 1 calc R . .
C1 C 0.80509(18) 0.47289(18) 0.22871(14) 0.0498(5) Uani 1 1 d . . .
H1A H 0.8959 0.5035 0.2282 0.075 Uiso 1 1 calc R . .
H1B H 0.7811 0.3839 0.2220 0.075 Uiso 1 1 calc R . .
H1C H 0.8000 0.5165 0.2970 0.075 Uiso 1 1 calc R . .
C5 C 1.0361(2) 0.67544(17) 0.54757(15) 0.0523(5) Uani 1 1 d . . .
H5 H 1.0352 0.6348 0.6030 0.063 Uiso 1 1 calc R . .
C36 C 0.81515(19) 0.43842(19) -0.01898(15) 0.0529(5) Uani 1 1 d . . .
H36 H 0.9006 0.4971 0.0207 0.063 Uiso 1 1 calc R . .
C24 C 0.35300(19) 0.45945(17) 0.28578(13) 0.0446(4) Uani 1 1 d . . .
C4 C 0.94596(19) 0.74229(17) 0.52147(14) 0.0473(4) Uani 1 1 d . . .
H4 H 0.8847 0.7470 0.5586 0.057 Uiso 1 1 calc R . .
C6 C 1.1267(2) 0.66836(17) 0.49275(14) 0.0505(5) Uani 1 1 d . . .
H6 H 1.1865 0.6234 0.5116 0.061 Uiso 1 1 calc R . .
C2 C 1.14345(19) 0.98474(17) 0.32796(15) 0.0530(5) Uani 1 1 d . . .
H2A H 1.2182 0.9580 0.3193 0.080 Uiso 1 1 calc R . .
H2B H 1.1673 1.0330 0.4032 0.080 Uiso 1 1 calc R . .
H2C H 1.1228 1.0361 0.2791 0.080 Uiso 1 1 calc R . .
C20 C 0.26836(19) 0.29199(18) 0.11297(15) 0.0501(5) Uani 1 1 d . . .
H20 H 0.2814 0.2496 0.0508 0.060 Uiso 1 1 calc R . .
C35 C 0.7900(2) 0.3583(2) -0.12139(16) 0.0571(5) Uani 1 1 d . . .
H35 H 0.8595 0.3625 -0.1507 0.068 Uiso 1 1 calc R . .
C34 C 0.6635(2) 0.27264(18) -0.18006(15) 0.0516(5) Uani 1 1 d . . .
H34 H 0.6488 0.2190 -0.2484 0.062 Uiso 1 1 calc R . .
C10 C 0.8518(2) 0.99494(18) 0.16062(15) 0.0555(5) Uani 1 1 d . . .
H10 H 0.9141 0.9721 0.1312 0.067 Uiso 1 1 calc R . .
C23 C 0.2288(2) 0.4172(2) 0.30167(17) 0.0603(6) Uani 1 1 d . . .
H23 H 0.2154 0.4575 0.3645 0.072 Uiso 1 1 calc R . .
C16 C 0.6712(2) 1.01803(19) 0.35558(17) 0.0595(5) Uani 1 1 d . . .
H16 H 0.6990 0.9820 0.4127 0.071 Uiso 1 1 calc R . .
C12 C 0.6891(2) 1.07240(18) 0.18686(18) 0.0619(6) Uani 1 1 d . . .
C19 C 0.7678(2) 1.05543(19) 0.11609(17) 0.0627(6) Uani 1 1 d . . .
C28 C 0.5023(2) 0.6575(2) 0.45403(15) 0.0657(6) Uani 1 1 d . . .
H28A H 0.5933 0.7147 0.4790 0.098 Uiso 1 1 calc R . .
H28B H 0.4908 0.6153 0.5095 0.098 Uiso 1 1 calc R . .
H28C H 0.4392 0.7039 0.4412 0.098 Uiso 1 1 calc R . .
C21 C 0.1473(2) 0.2535(2) 0.13171(17) 0.0650(6) Uani 1 1 d . . .
H21 H 0.0774 0.1838 0.0810 0.078 Uiso 1 1 calc R . .
C13 C 0.5856(3) 1.1267(2) 0.1833(3) 0.0850(8) Uani 1 1 d . . .
H13 H 0.5567 1.1629 0.1266 0.102 Uiso 1 1 calc R . .
C14 C 0.5273(3) 1.1260(3) 0.2638(3) 0.0908(9) Uani 1 1 d . . .
H14 H 0.4585 1.1617 0.2614 0.109 Uiso 1 1 calc R . .
C22 C 0.1272(2) 0.3161(2) 0.22427(19) 0.0697(6) Uani 1 1 d . . .
H22 H 0.0438 0.2890 0.2338 0.084 Uiso 1 1 calc R . .
C15 C 0.5698(2) 1.0726(2) 0.3486(2) 0.0787(7) Uani 1 1 d . . .
H15 H 0.5289 1.0735 0.4025 0.094 Uiso 1 1 calc R . .
C17 C 0.7567(3) 1.0966(3) 0.0123(2) 0.0908(8) Uani 1 1 d . . .
H17A H 0.7908 1.1871 0.0310 0.136 Uiso 1 1 calc R . .
H17B H 0.6632 1.0676 -0.0349 0.136 Uiso 1 1 calc R . .
H17C H 0.8088 1.0613 -0.0257 0.136 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
O1 C30 1.4309(19) . ?
O1 H1 0.8200 . ?
O2 C18 1.4211(18) . ?
O2 H2 0.8200 . ?
N2 C29 1.2943(19) . ?
N2 C32 1.4299(19) . ?
N1 C29 1.3665(19) . ?
N1 C25 1.409(2) . ?
N1 C26 1.412(2) . ?
C32 C33 1.372(2) . ?
C32 C31 1.383(2) . ?
C8 C7 1.369(2) . ?
C8 C3 1.389(2) . ?
C8 C18 1.508(2) . ?
C29 C30 1.540(2) . ?
C9 N4 1.288(2) . ?
C9 N3 1.375(2) . ?
C9 C18 1.543(2) . ?
N4 C3 1.419(2) . ?
C3 C4 1.374(2) . ?
C18 C2 1.525(2) . ?
C31 C36 1.373(2) . ?
C31 C30 1.505(2) . ?
N3 C10 1.401(2) . ?
N3 C11 1.407(2) . ?
C30 C1 1.522(2) . ?
C27 C26 1.341(2) . ?
C27 C24 1.439(3) . ?
C27 C28 1.499(2) . ?
C26 H26 0.9300 . ?
C33 C34 1.384(2) . ?
C33 H33 0.9300 . ?
C25 C20 1.376(2) . ?
C25 C24 1.404(2) . ?
C11 C16 1.386(3) . ?
C11 C12 1.404(3) . ?
C7 C6 1.385(2) . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C5 C6 1.376(3) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9300 . ?
C36 C35 1.384(2) . ?
C36 H36 0.9300 . ?
C24 C23 1.397(3) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C35 C34 1.372(3) . ?
C35 H35 0.9300 . ?
C34 H34 0.9300 . ?
C10 C19 1.343(3) . ?
C10 H10 0.9300 . ?
C23 C22 1.367(3) . ?
C23 H23 0.9300 . ?
C16 C15 1.380(3) . ?
C16 H16 0.9300 . ?
C12 C13 1.402(3) . ?
C12 C19 1.440(3) . ?
C19 C17 1.498(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9300 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C22 H22 0.9300 . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C30 O1 H1 109.5 . . ?
C18 O2 H2 109.5 . . ?
C29 N2 C32 106.02(13) . . ?
C29 N1 C25 126.55(13) . . ?
C29 N1 C26 125.86(14) . . ?
C25 N1 C26 107.51(13) . . ?
C33 C32 C31 121.51(15) . . ?
C33 C32 N2 126.34(15) . . ?
C31 C32 N2 112.15(13) . . ?
C7 C8 C3 120.37(16) . . ?
C7 C8 C18 131.92(15) . . ?
C3 C8 C18 107.71(15) . . ?
N2 C29 N1 122.83(14) . . ?
N2 C29 C30 114.94(13) . . ?
N1 C29 C30 122.23(13) . . ?
N4 C9 N3 122.61(16) . . ?
N4 C9 C18 115.46(15) . . ?
N3 C9 C18 121.93(14) . . ?
C9 N4 C3 105.89(14) . . ?
C4 C3 C8 121.16(16) . . ?
C4 C3 N4 126.19(15) . . ?
C8 C3 N4 112.61(14) . . ?
O2 C18 C8 113.89(14) . . ?
O2 C18 C2 107.17(13) . . ?
C8 C18 C2 111.38(14) . . ?
O2 C18 C9 114.11(13) . . ?
C8 C18 C9 98.18(12) . . ?
C2 C18 C9 112.07(14) . . ?
C36 C31 C32 120.54(15) . . ?
C36 C31 C30 131.30(15) . . ?
C32 C31 C30 108.13(13) . . ?
C9 N3 C10 125.22(16) . . ?
C9 N3 C11 127.11(15) . . ?
C10 N3 C11 107.56(16) . . ?
O1 C30 C31 113.52(13) . . ?
O1 C30 C1 108.14(13) . . ?
C31 C30 C1 111.47(14) . . ?
O1 C30 C29 111.54(13) . . ?
C31 C30 C29 98.69(12) . . ?
C1 C30 C29 113.40(14) . . ?
C26 C27 C24 107.24(15) . . ?
C26 C27 C28 126.38(18) . . ?
C24 C27 C28 126.28(17) . . ?
C27 C26 N1 110.31(16) . . ?
C27 C26 H26 124.8 . . ?
N1 C26 H26 124.8 . . ?
C32 C33 C34 117.48(17) . . ?
C32 C33 H33 121.3 . . ?
C34 C33 H33 121.3 . . ?
C20 C25 C24 122.38(16) . . ?
C20 C25 N1 130.87(15) . . ?
C24 C25 N1 106.75(15) . . ?
C16 C11 C12 122.2(2) . . ?
C16 C11 N3 131.03(18) . . ?
C12 C11 N3 106.77(18) . . ?
C8 C7 C6 119.01(17) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C30 C1 H1A 109.5 . . ?
C30 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C30 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C6 C5 C4 121.07(17) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C31 C36 C35 118.41(17) . . ?
C31 C36 H36 120.8 . . ?
C35 C36 H36 120.8 . . ?
C23 C24 C25 118.41(17) . . ?
C23 C24 C27 133.39(16) . . ?
C25 C24 C27 108.19(15) . . ?
C3 C4 C5 118.00(17) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C5 C6 C7 120.39(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C18 C2 H2A 109.5 . . ?
C18 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C18 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C25 C20 C21 117.34(17) . . ?
C25 C20 H20 121.3 . . ?
C21 C20 H20 121.3 . . ?
C34 C35 C36 120.56(17) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C35 C34 C33 121.47(16) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C19 C10 N3 110.8(2) . . ?
C19 C10 H10 124.6 . . ?
N3 C10 H10 124.6 . . ?
C22 C23 C24 119.51(17) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C15 C16 C11 117.4(2) . . ?
C15 C16 H16 121.3 . . ?
C11 C16 H16 121.3 . . ?
C11 C12 C13 118.4(2) . . ?
C11 C12 C19 108.13(19) . . ?
C13 C12 C19 133.5(2) . . ?
C10 C19 C12 106.78(18) . . ?
C10 C19 C17 126.9(2) . . ?
C12 C19 C17 126.4(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C20 C21 C22 121.7(2) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C23 C22 C21 120.68(19) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C16 C15 C14 121.8(3) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C19 C17 H17A 109.5 . . ?
C19 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C19 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 956411'
#######################################################################
#
#                 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_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N3 O'
_chemical_formula_sum            'C17 H13 N3 O'
_chemical_formula_weight         275.30

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                   10.830(3)
_cell_length_b                   12.205(3)
_cell_length_c                   12.209(3)
_cell_angle_alpha                102.677(4)
_cell_angle_beta                 106.686(4)
_cell_angle_gamma                110.923(4)
_cell_volume                     1347.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6487
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.09

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_T_max  0.9870
_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            12936
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.09
_reflns_number_total             4749
_reflns_number_gt                4059
_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)+(0.1190P)²+0.2682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4749
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_restrained_S_all      0.804
_refine_ls_shift/su_max          0.083
_refine_ls_shift/su_mean         0.006

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
O2 O 0.30250(10) 0.20176(9) 0.86527(9) 0.0487(3) Uani 1 1 d . . .
O1 O 0.82099(9) 0.72732(9) 0.91387(9) 0.0513(3) Uani 1 1 d . . .
N4 N 0.20053(13) -0.05775(11) 1.02799(11) 0.0548(3) Uani 1 1 d . . .
N5 N 0.64627(11) 0.53573(10) 0.88024(10) 0.0442(3) Uani 1 1 d . . .
C16 C 0.27851(13) 0.12552(11) 0.91678(11) 0.0387(3) Uani 1 1 d . . .
C28 C 0.60116(14) 0.63594(12) 0.73627(12) 0.0414(3) Uani 1 1 d . . .
C34 C 0.70035(13) 0.64140(12) 0.84875(12) 0.0405(3) Uani 1 1 d . . .
N6 N 0.41668(13) 0.43515(12) 0.71491(12) 0.0593(4) Uani 1 1 d . . .
N3 N 0.14054(11) 0.02773(10) 0.87597(9) 0.0410(3) Uani 1 1 d . . .
C6 C 0.38459(14) 0.12573(12) 1.02104(12) 0.0398(3) Uani 1 1 d . . .
N2 N -0.04036(13) 0.08624(11) 0.77312(10) 0.0501(3) Uani 1 1 d . . .
H6 H -0.0231 0.1457 0.8369 0.060 Uiso 1 1 calc R . .
C19 C 0.73762(14) 0.52058(12) 0.97948(12) 0.0432(3) Uani 1 1 d . . .
C9 C -0.02223(13) -0.07234(12) 0.65398(11) 0.0403(3) Uani 1 1 d . . .
C8 C 0.02915(14) 0.01148(12) 0.76850(11) 0.0408(3) Uani 1 1 d . . .
C18 C 0.78981(14) 0.43455(12) 0.97352(13) 0.0455(3) Uani 1 1 d . . .
C7 C 0.11005(15) -0.05653(13) 0.93522(13) 0.0501(4) Uani 1 1 d . . .
H8 H 0.0150 -0.1178 0.9046 0.060 Uiso 1 1 calc R . .
C10 C -0.13262(13) -0.04894(12) 0.58027(12) 0.0408(3) Uani 1 1 d . . .
C5 C 0.34264(15) 0.03411(13) 1.07281(12) 0.0453(3) Uani 1 1 d . . .
C14 C -0.32294(15) -0.06102(15) 0.41309(14) 0.0558(4) Uani 1 1 d . . .
H14 H -0.3846 -0.0967 0.3305 0.067 Uiso 1 1 calc R . .
C15 C -0.22448(15) -0.10366(13) 0.45568(13) 0.0492(3) Uani 1 1 d . . .
H15 H -0.2188 -0.1676 0.4029 0.059 Uiso 1 1 calc R . .
C26 C 0.50730(15) 0.44048(14) 0.81171(14) 0.0550(4) Uani 1 1 d . . .
H26 H 0.4774 0.3741 0.8390 0.066 Uiso 1 1 calc R . .
C20 C 0.87440(14) 0.45823(12) 1.09765(13) 0.0463(3) Uani 1 1 d . . .
C32 C 0.54846(17) 0.72609(16) 0.58340(15) 0.0622(4) Uani 1 1 d . . .
H32 H 0.5765 0.7897 0.5524 0.075 Uiso 1 1 calc R . .
C29 C 0.46328(15) 0.53435(13) 0.67375(13) 0.0482(3) Uani 1 1 d . . .
C27 C 0.76546(18) 0.33538(14) 0.86197(15) 0.0622(4) Uani 1 1 d . . .
H27A H 0.7144 0.3464 0.7900 0.093 Uiso 1 1 calc R . .
H27B H 0.7096 0.2539 0.8616 0.093 Uiso 1 1 calc R . .
H27C H 0.8568 0.3421 0.8626 0.093 Uiso 1 1 calc R . .
C33 C 0.64197(16) 0.73170(14) 0.68940(14) 0.0515(4) Uani 1 1 d . . .
H33 H 0.7334 0.7996 0.7307 0.062 Uiso 1 1 calc R . .
C17 C 0.02463(16) -0.16845(13) 0.61205(14) 0.0529(4) Uani 1 1 d . . .
H17A H 0.0893 -0.1727 0.6818 0.079 Uiso 1 1 calc R . .
H17B H 0.0731 -0.1458 0.5600 0.079 Uiso 1 1 calc R . .
H17C H -0.0582 -0.2489 0.5673 0.079 Uiso 1 1 calc R . .
C11 C -0.14223(15) 0.04868(13) 0.65735(12) 0.0458(3) Uani 1 1 d . . .
C1 C 0.52781(15) 0.21807(14) 1.07123(14) 0.0525(4) Uani 1 1 d . . .
H1 H 0.5556 0.2789 1.0370 0.063 Uiso 1 1 calc R . .
C21 C 0.86629(15) 0.55867(13) 1.17273(13) 0.0490(3) Uani 1 1 d . . .
C4 C 0.44622(17) 0.03640(16) 1.17366(14) 0.0599(4) Uani 1 1 d . . .
H4 H 0.4202 -0.0239 1.2088 0.072 Uiso 1 1 calc R . .
C30 C 0.36907(17) 0.53055(16) 0.56606(15) 0.0622(4) Uani 1 1 d . . .
H30 H 0.2771 0.4635 0.5240 0.075 Uiso 1 1 calc R . .
C12 C -0.24321(17) 0.09105(16) 0.61298(15) 0.0590(4) Uani 1 1 d . . .
H12 H -0.2497 0.1554 0.6644 0.071 Uiso 1 1 calc R . .
C31 C 0.41168(18) 0.62544(17) 0.52201(15) 0.0669(5) Uani 1 1 d . . .
H31 H 0.3482 0.6223 0.4501 0.080 Uiso 1 1 calc R . .
C13 C -0.33248(16) 0.03459(17) 0.49101(15) 0.0595(4) Uani 1 1 d . . .
H13 H -0.4012 0.0608 0.4595 0.071 Uiso 1 1 calc R . .
C25 C 0.95870(16) 0.40511(15) 1.15222(16) 0.0591(4) Uani 1 1 d . . .
H25 H 0.9666 0.3392 1.1046 0.071 Uiso 1 1 calc R . .
C24 C 1.02914(18) 0.45208(17) 1.27701(18) 0.0719(5) Uani 1 1 d . . .
H24 H 1.0858 0.4177 1.3140 0.086 Uiso 1 1 calc R . .
C2 C 0.62701(16) 0.21875(17) 1.17071(15) 0.0640(4) Uani 1 1 d . . .
H5 H 0.7221 0.2806 1.2048 0.077 Uiso 1 1 calc R . .
C3 C 0.58566(17) 0.12699(17) 1.22089(15) 0.0664(5) Uani 1 1 d . . .
H3 H 0.6541 0.1273 1.2878 0.080 Uiso 1 1 calc R . .
C22 C 0.93686(19) 0.60514(18) 1.29908(15) 0.0668(4) Uani 1 1 d . . .
H22 H 0.9298 0.6709 1.3479 0.080 Uiso 1 1 calc R . .
C23 C 1.01808(19) 0.55007(19) 1.34979(17) 0.0762(5) Uani 1 1 d . . .
H23 H 1.0665 0.5791 1.4345 0.091 Uiso 1 1 calc R . .
N1 N 0.78076(13) 0.59538(11) 1.09795(10) 0.0498(3) Uani 1 1 d . . .
H7 H 0.7583 0.6547 1.1213 0.060 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
O2 C16 1.2276(15) . ?
O1 C34 1.2238(15) . ?
N4 C7 1.2742(18) . ?
N4 C5 1.3928(18) . ?
N5 C26 1.3845(18) . ?
N5 C34 1.4006(17) . ?
N5 C19 1.4218(17) . ?
C16 N3 1.3939(16) . ?
C16 C6 1.4481(18) . ?
C28 C29 1.3991(19) . ?
C28 C33 1.3996(19) . ?
C28 C34 1.4512(19) . ?
N6 C26 1.2724(19) . ?
N6 C29 1.3962(19) . ?
N3 C7 1.3825(17) . ?
N3 C8 1.4221(16) . ?
C6 C1 1.3978(19) . ?
C6 C5 1.4030(19) . ?
N2 C8 1.3765(18) . ?
N2 C11 1.3727(18) . ?
N2 H6 0.8600 . ?
C19 C18 1.3569(19) . ?
C19 N1 1.3681(18) . ?
C9 C8 1.3528(18) . ?
C9 C10 1.4351(18) . ?
C9 C17 1.4854(19) . ?
C18 C20 1.429(2) . ?
C18 C27 1.494(2) . ?
C7 H8 0.9300 . ?
C10 C11 1.403(2) . ?
C10 C15 1.4001(19) . ?
C5 C4 1.395(2) . ?
C14 C15 1.369(2) . ?
C14 C13 1.390(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C26 H26 0.9300 . ?
C20 C25 1.400(2) . ?
C20 C21 1.407(2) . ?
C32 C33 1.365(2) . ?
C32 C31 1.387(2) . ?
C32 H32 0.9300 . ?
C29 C30 1.393(2) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C33 H33 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C11 C12 1.394(2) . ?
C1 C2 1.367(2) . ?
C1 H1 0.9300 . ?
C21 N1 1.3721(18) . ?
C21 C22 1.384(2) . ?
C4 C3 1.365(2) . ?
C4 H4 0.9300 . ?
C30 C31 1.370(2) . ?
C30 H30 0.9300 . ?
C12 C13 1.369(2) . ?
C12 H12 0.9300 . ?
C31 H31 0.9300 . ?
C13 H13 0.9300 . ?
C25 C24 1.367(3) . ?
C25 H25 0.9300 . ?
C24 C23 1.390(3) . ?
C24 H24 0.9300 . ?
C2 C3 1.390(2) . ?
C2 H5 0.9300 . ?
C3 H3 0.9300 . ?
C22 C23 1.379(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N1 H7 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N4 C5 116.64(12) . . ?
C26 N5 C34 121.37(11) . . ?
C26 N5 C19 118.52(11) . . ?
C34 N5 C19 119.97(10) . . ?
O2 C16 N3 120.71(11) . . ?
O2 C16 C6 125.36(12) . . ?
N3 C16 C6 113.93(11) . . ?
C29 C28 C33 119.42(13) . . ?
C29 C28 C34 119.99(12) . . ?
C33 C28 C34 120.59(12) . . ?
O1 C34 N5 120.30(12) . . ?
O1 C34 C28 126.00(12) . . ?
N5 C34 C28 113.70(11) . . ?
C26 N6 C29 116.49(12) . . ?
C7 N3 C16 121.64(11) . . ?
C7 N3 C8 118.96(11) . . ?
C16 N3 C8 119.37(10) . . ?
C1 C6 C5 120.08(12) . . ?
C1 C6 C16 120.15(12) . . ?
C5 C6 C16 119.76(12) . . ?
C8 N2 C11 107.55(11) . . ?
C8 N2 H6 126.2 . . ?
C11 N2 H6 126.2 . . ?
C18 C19 N1 111.68(12) . . ?
C18 C19 N5 127.47(13) . . ?
N1 C19 N5 120.83(12) . . ?
C8 C9 C10 105.33(12) . . ?
C8 C9 C17 127.85(12) . . ?
C10 C9 C17 126.83(12) . . ?
C9 C8 N2 111.68(11) . . ?
C9 C8 N3 127.81(12) . . ?
N2 C8 N3 120.52(11) . . ?
C19 C18 C20 105.44(12) . . ?
C19 C18 C27 128.03(14) . . ?
C20 C18 C27 126.53(13) . . ?
N4 C7 N3 125.82(12) . . ?
N4 C7 H8 117.1 . . ?
N3 C7 H8 117.1 . . ?
C11 C10 C15 119.46(13) . . ?
C11 C10 C9 107.62(12) . . ?
C15 C10 C9 132.92(13) . . ?
N4 C5 C4 118.96(12) . . ?
N4 C5 C6 122.14(12) . . ?
C4 C5 C6 118.89(13) . . ?
C15 C14 C13 121.22(14) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C10 118.62(14) . . ?
C14 C15 H15 120.7 . . ?
C10 C15 H15 120.7 . . ?
N6 C26 N5 126.15(13) . . ?
N6 C26 H26 116.9 . . ?
N5 C26 H26 116.9 . . ?
C25 C20 C21 119.03(14) . . ?
C25 C20 C18 133.51(15) . . ?
C21 C20 C18 107.44(12) . . ?
C33 C32 C31 119.94(14) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
N6 C29 C28 122.20(13) . . ?
N6 C29 C30 118.45(13) . . ?
C28 C29 C30 119.35(13) . . ?
C18 C27 H27A 109.5 . . ?
C18 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C18 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C32 C33 C28 120.43(14) . . ?
C32 C33 H33 119.8 . . ?
C28 C33 H33 119.8 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C11 C12 130.80(14) . . ?
N2 C11 C10 107.81(12) . . ?
C12 C11 C10 121.39(13) . . ?
C2 C1 C6 119.86(14) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
N1 C21 C22 130.16(15) . . ?
N1 C21 C20 107.77(12) . . ?
C22 C21 C20 122.07(14) . . ?
C3 C4 C5 120.11(14) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C31 C30 C29 120.11(15) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C13 C12 C11 117.67(15) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C30 C31 C32 120.76(15) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C12 C13 C14 121.64(14) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C24 C25 C20 118.63(17) . . ?
C24 C25 H25 120.7 . . ?
C20 C25 H25 120.7 . . ?
C25 C24 C23 121.51(16) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C1 C2 C3 119.98(14) . . ?
C1 C2 H5 120.0 . . ?
C3 C2 H5 120.0 . . ?
C4 C3 C2 121.08(14) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C23 C22 C21 117.35(18) . . ?
C23 C22 H22 121.3 . . ?
C21 C22 H22 121.3 . . ?
C22 C23 C24 121.39(17) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C19 N1 C21 107.66(12) . . ?
C19 N1 H7 126.2 . . ?
C21 N1 H7 126.2 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.123
_database_code_depnum_ccdc_archive 'CCDC 956412'
