# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_cb1
_database_code_depnum_ccdc_archive 'CCDC 1409892'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18.50 N3 O3'
_chemical_formula_weight         372.90

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   Pna2(1)

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

_cell_length_a                   24.313(12)
_cell_length_b                   8.910(5)
_cell_length_c                   17.683(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3831(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1564
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26140
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.99
_reflns_number_total             6925
_reflns_number_gt                5868
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0859P)²+0.1831P] 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   0.1(8)
_refine_ls_number_reflns         6925
_refine_ls_number_parameters     529
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   0.820
_refine_ls_restrained_S_all      0.820
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23845(5) 0.43511(18) 0.58891(8) 0.0514(4) Uani 1 1 d . . .
O2 O 0.38423(5) 0.44227(16) 0.45151(8) 0.0483(4) Uani 1 1 d . . .
O3 O 0.19752(5) 0.56618(18) 0.42044(11) 0.0636(4) Uani 1 1 d . . .
O4 O -0.01621(6) 0.97326(18) 0.02184(9) 0.0566(4) Uani 1 1 d . . .
O5 O 0.13700(5) 0.94958(14) 0.15549(8) 0.0426(3) Uani 1 1 d . . .
O6 O -0.04898(6) 0.81897(19) 0.19029(10) 0.0617(4) Uani 1 1 d . . .
N1 N 0.18433(6) 0.27849(18) 0.51808(10) 0.0402(4) Uani 1 1 d . . .
C100 C 0.27074(7) 0.3376(2) 0.46519(11) 0.0363(4) Uani 1 1 d . . .
N3 N 0.42048(7) 0.2394(2) 0.50340(11) 0.0518(5) Uani 1 1 d D . .
H@4 H 0.4210(11) 0.1545(19) 0.5267(16) 0.078 Uiso 1 1 d D . .
H@3 H 0.4495(7) 0.292(3) 0.5034(16) 0.078 Uiso 1 1 d D . .
N4 N 0.31547(8) -0.0155(3) 0.54202(17) 0.0815(8) Uani 1 1 d . . .
N5 N 0.17148(6) 1.1546(2) 0.10275(11) 0.0467(4) Uani 1 1 d D . .
H@1 H 0.1712(10) 1.2414(17) 0.0828(15) 0.070 Uiso 1 1 d D . .
H@2 H 0.2015(7) 1.105(2) 0.1016(16) 0.070 Uiso 1 1 d D . .
N6 N 0.05994(8) 1.3909(3) 0.05208(16) 0.0757(7) Uani 1 1 d . . .
C1 C 0.05364(10) 0.4353(3) 0.51330(19) 0.0718(8) Uani 1 1 d . . .
H200 H 0.0240 0.4897 0.4945 0.086 Uiso 1 1 calc R . .
C2 C 0.09096(8) 0.3666(2) 0.53704(14) 0.0522(5) Uani 1 1 d . . .
C3 C 0.13644(7) 0.2784(3) 0.56767(13) 0.0502(5) Uani 1 1 d . . .
H3A H 0.1468 0.3190 0.6165 0.060 Uiso 1 1 calc R . .
H3B H 0.1243 0.1759 0.5753 0.060 Uiso 1 1 calc R . .
C4 C 0.23027(7) 0.3612(2) 0.53247(11) 0.0383(4) Uani 1 1 d . . .
C5 C 0.28860(7) 0.4861(2) 0.43229(12) 0.0398(4) Uani 1 1 d . . .
C6 C 0.24554(8) 0.5935(2) 0.40856(12) 0.0458(5) Uani 1 1 d . . .
C7 C 0.26400(9) 0.7380(3) 0.37289(17) 0.0601(6) Uani 1 1 d . . .
H7A H 0.2683 0.8130 0.4122 0.072 Uiso 1 1 calc R . .
H7B H 0.2355 0.7728 0.3387 0.072 Uiso 1 1 calc R . .
C8 C 0.31803(9) 0.7247(3) 0.32910(16) 0.0577(6) Uani 1 1 d . . .
C9 C 0.31138(13) 0.6222(3) 0.26138(16) 0.0747(8) Uani 1 1 d . . .
H9A H 0.2863 0.6669 0.2260 0.112 Uiso 1 1 calc R . .
H9B H 0.2971 0.5271 0.2777 0.112 Uiso 1 1 calc R . .
H9C H 0.3465 0.6077 0.2376 0.112 Uiso 1 1 calc R . .
C10 C 0.23582(7) 0.2478(2) 0.41100(11) 0.0379(4) Uani 1 1 d . . .
C11 C 0.24699(8) 0.1979(2) 0.33920(12) 0.0483(5) Uani 1 1 d . . .
H11 H 0.2804 0.2194 0.3161 0.058 Uiso 1 1 calc R . .
C12 C 0.20687(9) 0.1141(3) 0.30167(14) 0.0572(6) Uani 1 1 d . . .
H12 H 0.2133 0.0796 0.2528 0.069 Uiso 1 1 calc R . .
C13 C 0.15797(9) 0.0825(3) 0.33683(15) 0.0583(6) Uani 1 1 d . . .
H13 H 0.1320 0.0253 0.3112 0.070 Uiso 1 1 calc R . .
C14 C 0.14581(8) 0.1325(2) 0.40883(14) 0.0508(5) Uani 1 1 d . . .
H14 H 0.1122 0.1115 0.4316 0.061 Uiso 1 1 calc R . .
C15 C 0.18571(7) 0.2149(2) 0.44538(12) 0.0400(4) Uani 1 1 d . . .
C16 C 0.32179(7) 0.2522(2) 0.49028(12) 0.0397(4) Uani 1 1 d . . .
C17 C 0.37361(7) 0.3067(2) 0.48332(11) 0.0397(4) Uani 1 1 d . . .
C18 C 0.34115(7) 0.5262(2) 0.42417(11) 0.0425(4) Uani 1 1 d . . .
C19 C 0.36095(9) 0.6621(3) 0.38432(15) 0.0557(6) Uani 1 1 d . . .
H19A H 0.3942 0.6377 0.3567 0.067 Uiso 1 1 calc R . .
H19B H 0.3700 0.7386 0.4213 0.067 Uiso 1 1 calc R . .
C20 C 0.33684(12) 0.8782(3) 0.3018(2) 0.0831(9) Uani 1 1 d . . .
H20A H 0.3711 0.8684 0.2753 0.125 Uiso 1 1 calc R . .
H20B H 0.3417 0.9436 0.3445 0.125 Uiso 1 1 calc R . .
H20C H 0.3096 0.9197 0.2685 0.125 Uiso 1 1 calc R . .
C21 C 0.31673(8) 0.1054(3) 0.51923(14) 0.0521(5) Uani 1 1 d . . .
C22 C -0.20127(12) 1.1057(5) 0.0994(3) 0.1112(13) Uani 1 1 d . . .
H22 H -0.2354 1.0788 0.1188 0.133 Uiso 1 1 calc R . .
C23 C -0.15842(10) 1.1396(3) 0.0751(2) 0.0799(9) Uani 1 1 d . . .
C24 C -0.10496(10) 1.1854(3) 0.04782(19) 0.0680(7) Uani 1 1 d . . .
N100 N -0.06046(6) 1.1429(2) 0.09909(12) 0.0521(5) Uani 1 1 d . . .
C26 C -0.01977(7) 1.0442(2) 0.08031(12) 0.0433(5) Uani 1 1 d . . .
C27 C 0.02316(7) 1.0490(2) 0.14542(11) 0.0382(4) Uani 1 1 d . . .
C28 C 0.04174(7) 0.8961(2) 0.17149(11) 0.0389(4) Uani 1 1 d . . .
C29 C 0.09435(7) 0.8586(2) 0.17811(10) 0.0384(4) Uani 1 1 d . . .
C30 C 0.11577(8) 0.7159(2) 0.21011(14) 0.0496(5) Uani 1 1 d . . .
H30A H 0.1487 0.7370 0.2393 0.060 Uiso 1 1 calc R . .
H30B H 0.1260 0.6496 0.1689 0.060 Uiso 1 1 calc R . .
C31 C 0.07420(9) 0.6356(2) 0.26072(14) 0.0536(6) Uani 1 1 d . . .
C32 C 0.09480(13) 0.4755(3) 0.2754(2) 0.0805(9) Uani 1 1 d . . .
H32A H 0.0990 0.4238 0.2281 0.121 Uiso 1 1 calc R . .
H32B H 0.0687 0.4230 0.3063 0.121 Uiso 1 1 calc R . .
H32C H 0.1296 0.4794 0.3009 0.121 Uiso 1 1 calc R . .
C33 C 0.07298(7) 1.1356(2) 0.11610(11) 0.0382(4) Uani 1 1 d . . .
C34 C 0.12527(7) 1.0856(2) 0.12334(11) 0.0377(4) Uani 1 1 d . . .
C35 C -0.00063(8) 0.7864(2) 0.19435(12) 0.0466(5) Uani 1 1 d . . .
C36 C 0.01905(10) 0.6326(3) 0.21798(16) 0.0607(6) Uani 1 1 d . . .
H36A H 0.0230 0.5704 0.1733 0.073 Uiso 1 1 calc R . .
H36B H -0.0086 0.5868 0.2501 0.073 Uiso 1 1 calc R . .
C37 C 0.06813(12) 0.7160(3) 0.33608(15) 0.0724(7) Uani 1 1 d . . .
H37A H 0.1032 0.7199 0.3610 0.109 Uiso 1 1 calc R . .
H37B H 0.0424 0.6627 0.3673 0.109 Uiso 1 1 calc R . .
H37C H 0.0550 0.8162 0.3276 0.109 Uiso 1 1 calc R . .
C38 C 0.06519(7) 1.2759(2) 0.08143(14) 0.0485(5) Uani 1 1 d . . .
C39 C -0.00764(7) 1.1354(2) 0.20527(12) 0.0419(5) Uani 1 1 d . . .
C40 C 0.00538(9) 1.1609(3) 0.27961(13) 0.0515(5) Uani 1 1 d . . .
H40 H 0.0376 1.1227 0.3003 0.062 Uiso 1 1 calc R . .
C41 C -0.03042(11) 1.2444(3) 0.32285(16) 0.0694(7) Uani 1 1 d . . .
H41 H -0.0223 1.2621 0.3735 0.083 Uiso 1 1 calc R . .
C42 C -0.07737(11) 1.3013(3) 0.29287(18) 0.0749(8) Uani 1 1 d . . .
H42 H -0.1008 1.3573 0.3233 0.090 Uiso 1 1 calc R . .
C43 C -0.09112(10) 1.2774(3) 0.21711(18) 0.0665(7) Uani 1 1 d . . .
H43 H -0.1230 1.3176 0.1963 0.080 Uiso 1 1 calc R . .
C44 C -0.05549(8) 1.1920(2) 0.17450(14) 0.0490(5) Uani 1 1 d . . .
H100 H -0.1067(11) 1.298(4) 0.0421(17) 0.082(8) Uiso 1 1 d . . .
H101 H -0.0957(12) 1.141(3) -0.0065(17) 0.077(8) Uiso 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
O1 C4 1.212(2) . ?
O2 C17 1.357(3) . ?
O2 C18 1.375(2) . ?
O3 C6 1.211(2) . ?
O4 C26 1.215(3) . ?
O5 C34 1.369(2) . ?
O5 C29 1.376(2) . ?
O6 C35 1.213(2) . ?
N1 C4 1.362(2) . ?
N1 C15 1.405(3) . ?
N1 C3 1.458(3) . ?
C100 C5 1.509(3) . ?
C100 C10 1.510(3) . ?
C100 C16 1.522(3) . ?
C100 C4 1.558(3) . ?
N3 C17 1.336(3) . ?
N3 H@4 0.862(10) . ?
N3 H@3 0.849(10) . ?
N4 C21 1.150(3) . ?
N5 C34 1.332(2) . ?
N5 H@1 0.849(10) . ?
N5 H@2 0.853(10) . ?
N6 C38 1.155(3) . ?
C1 C2 1.172(3) . ?
C1 H200 0.9300 . ?
C2 C3 1.460(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C18 1.334(3) . ?
C5 C6 1.479(3) . ?
C6 C7 1.502(3) . ?
C7 C8 1.530(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.515(4) . ?
C8 C20 1.521(3) . ?
C8 C19 1.534(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.372(3) . ?
C10 C15 1.393(3) . ?
C11 C12 1.396(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C16 C17 1.356(3) . ?
C16 C21 1.410(3) . ?
C18 C19 1.482(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 C23 1.167(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.445(4) . ?
C24 N100 1.462(3) . ?
C24 H100 1.01(3) . ?
C24 H101 1.06(3) . ?
N100 C26 1.365(3) . ?
N100 C44 1.409(3) . ?
C26 C27 1.555(3) . ?
C27 C28 1.507(3) . ?
C27 C39 1.508(3) . ?
C27 C33 1.527(3) . ?
C28 C29 1.327(3) . ?
C28 C35 1.476(3) . ?
C29 C30 1.486(3) . ?
C30 C31 1.528(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C37 1.520(4) . ?
C31 C32 1.534(3) . ?
C31 C36 1.539(3) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.353(3) . ?
C33 C38 1.405(3) . ?
C35 C36 1.511(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C39 C40 1.371(3) . ?
C39 C44 1.380(3) . ?
C40 C41 1.377(3) . ?
C40 H40 0.9300 . ?
C41 C42 1.357(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.397(4) . ?
C42 H42 0.9300 . ?
C43 C44 1.378(3) . ?
C43 H43 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
C17 O2 C18 119.00(14) . . ?
C34 O5 C29 119.04(14) . . ?
C4 N1 C15 111.68(15) . . ?
C4 N1 C3 122.87(17) . . ?
C15 N1 C3 124.70(16) . . ?
C5 C100 C10 112.45(16) . . ?
C5 C100 C16 108.44(15) . . ?
C10 C100 C16 112.23(15) . . ?
C5 C100 C4 110.95(15) . . ?
C10 C100 C4 101.61(14) . . ?
C16 C100 C4 111.09(16) . . ?
C17 N3 H@4 122.3(18) . . ?
C17 N3 H@3 117.3(19) . . ?
H@4 N3 H@3 118(2) . . ?
C34 N5 H@1 121.7(17) . . ?
C34 N5 H@2 119.3(17) . . ?
H@1 N5 H@2 118(2) . . ?
C2 C1 H200 180.0 . . ?
C1 C2 C3 178.5(2) . . ?
N1 C3 C2 112.43(19) . . ?
N1 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O1 C4 N1 125.61(17) . . ?
O1 C4 C100 126.77(16) . . ?
N1 C4 C100 107.58(16) . . ?
C18 C5 C6 118.30(18) . . ?
C18 C5 C100 123.47(18) . . ?
C6 C5 C100 118.23(15) . . ?
O3 C6 C5 120.20(19) . . ?
O3 C6 C7 122.23(19) . . ?
C5 C6 C7 117.52(17) . . ?
C6 C7 C8 113.78(19) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C20 108.9(2) . . ?
C9 C8 C7 110.8(2) . . ?
C20 C8 C7 110.4(2) . . ?
C9 C8 C19 110.9(2) . . ?
C20 C8 C19 108.9(2) . . ?
C7 C8 C19 106.9(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 120.58(18) . . ?
C11 C10 C100 130.36(18) . . ?
C15 C10 C100 109.04(17) . . ?
C10 C11 C12 118.3(2) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 120.0(2) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 122.5(2) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
C15 C14 C13 117.0(2) . . ?
C15 C14 H14 121.5 . . ?
C13 C14 H14 121.5 . . ?
C14 C15 C10 121.6(2) . . ?
C14 C15 N1 128.84(18) . . ?
C10 C15 N1 109.60(16) . . ?
C17 C16 C21 116.51(18) . . ?
C17 C16 C100 123.51(18) . . ?
C21 C16 C100 119.91(16) . . ?
N3 C17 C16 127.4(2) . . ?
N3 C17 O2 110.32(16) . . ?
C16 C17 O2 122.23(17) . . ?
C5 C18 O2 123.11(19) . . ?
C5 C18 C19 125.52(19) . . ?
O2 C18 C19 111.36(16) . . ?
C18 C19 C8 112.27(17) . . ?
C18 C19 H19A 109.1 . . ?
C8 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C8 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C8 C20 H20A 109.5 . . ?
C8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 C16 176.4(2) . . ?
C23 C22 H22 180.0 . . ?
C22 C23 C24 177.5(4) . . ?
C23 C24 N100 112.7(2) . . ?
C23 C24 H100 106.0(16) . . ?
N100 C24 H100 110.6(17) . . ?
C23 C24 H101 112.9(16) . . ?
N100 C24 H101 107.9(16) . . ?
H100 C24 H101 107(2) . . ?
C26 N100 C44 111.60(17) . . ?
C26 N100 C24 123.5(2) . . ?
C44 N100 C24 124.8(2) . . ?
O4 C26 N100 126.44(19) . . ?
O4 C26 C27 126.64(18) . . ?
N100 C26 C27 106.78(18) . . ?
C28 C27 C39 113.30(17) . . ?
C28 C27 C33 108.84(14) . . ?
C39 C27 C33 111.97(15) . . ?
C28 C27 C26 113.75(16) . . ?
C39 C27 C26 101.57(15) . . ?
C33 C27 C26 107.16(16) . . ?
C29 C28 C35 118.79(18) . . ?
C29 C28 C27 122.91(16) . . ?
C35 C28 C27 118.22(16) . . ?
C28 C29 O5 123.53(18) . . ?
C28 C29 C30 125.93(18) . . ?
O5 C29 C30 110.54(15) . . ?
C29 C30 C31 113.07(17) . . ?
C29 C30 H30A 109.0 . . ?
C31 C30 H30A 109.0 . . ?
C29 C30 H30B 109.0 . . ?
C31 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
C37 C31 C30 110.91(19) . . ?
C37 C31 C32 108.8(2) . . ?
C30 C31 C32 108.6(2) . . ?
C37 C31 C36 110.7(2) . . ?
C30 C31 C36 107.27(19) . . ?
C32 C31 C36 110.57(19) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C38 117.45(17) . . ?
C34 C33 C27 123.13(17) . . ?
C38 C33 C27 119.40(16) . . ?
N5 C34 C33 127.93(18) . . ?
N5 C34 O5 110.27(15) . . ?
C33 C34 O5 121.79(16) . . ?
O6 C35 C28 120.1(2) . . ?
O6 C35 C36 122.69(19) . . ?
C28 C35 C36 117.09(18) . . ?
C35 C36 C31 113.32(18) . . ?
C35 C36 H36A 108.9 . . ?
C31 C36 H36A 108.9 . . ?
C35 C36 H36B 108.9 . . ?
C31 C36 H36B 108.9 . . ?
H36A C36 H36B 107.7 . . ?
C31 C37 H37A 109.5 . . ?
C31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N6 C38 C33 178.4(2) . . ?
C40 C39 C44 120.82(19) . . ?
C40 C39 C27 130.01(18) . . ?
C44 C39 C27 109.17(19) . . ?
C39 C40 C41 118.4(2) . . ?
C39 C40 H40 120.8 . . ?
C41 C40 H40 120.8 . . ?
C42 C41 C40 121.1(3) . . ?
C42 C41 H41 119.4 . . ?
C40 C41 H41 119.4 . . ?
C41 C42 C43 121.3(2) . . ?
C41 C42 H42 119.4 . . ?
C43 C42 H42 119.4 . . ?
C44 C43 C42 117.3(2) . . ?
C44 C43 H43 121.4 . . ?
C42 C43 H43 121.4 . . ?
C43 C44 C39 121.1(2) . . ?
C43 C44 N100 129.4(2) . . ?
C39 C44 N100 109.42(18) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.032
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_cb1
_database_code_depnum_ccdc_archive 'CCDC 1411963'
_audit_update_record             
;
2015-07-10 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 I N5 O2'
_chemical_formula_weight         419.68

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           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.6342(5)
_cell_length_b                   9.4462(6)
_cell_length_c                   12.1984(7)
_cell_angle_alpha                80.301(3)
_cell_angle_beta                 73.647(3)
_cell_angle_gamma                71.635(3)
_cell_volume                     798.02(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             409
_exptl_absorpt_coefficient_mu    2.023
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker APEX2'
_diffrn_measurement_method       'Bruker SAINT'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8714
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         27.18
_reflns_number_total             4877
_reflns_number_gt                4073
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0851P)²+2.3704P] 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   0.18(6)
_refine_ls_number_reflns         4877
_refine_ls_number_parameters     425
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_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
I1 I 1.06453(7) 0.30628(6) 0.33431(5) 0.0584(3) Uani 1 1 d . . .
I2 I -0.03993(7) 0.68456(6) 0.66587(5) 0.0597(3) Uani 1 1 d . . .
N104 N 0.5630(17) 0.6172(11) 0.8692(12) 0.038(3) Uani 1 1 d . . .
O2 O 0.6267(17) 0.1119(12) 0.9916(11) 0.041(3) Uani 1 1 d . . .
N100 N 0.3891(16) 0.9221(13) 0.1940(11) 0.032(3) Uani 1 1 d . . .
H212 H 0.4678 0.9752 0.1757 0.038 Uiso 1 1 calc R . .
O4 O 0.3920(13) 0.8824(10) 0.0138(9) 0.030(2) Uani 1 1 d . . .
O100 O 0.9468(15) 0.3886(10) 0.9553(10) 0.036(3) Uani 1 1 d . . .
C102 C 1.0122(18) 0.1738(13) 0.8532(14) 0.025(3) Uani 1 1 d . . .
C100 C 0.911(3) 0.2279(17) 0.4862(16) 0.043(4) Uani 1 1 d . . .
N4 N 0.6396(18) 0.0670(14) 0.8084(13) 0.048(4) Uani 1 1 d . . .
H210 H 0.5764 0.0020 0.8278 0.057 Uiso 1 1 calc R . .
C103 C 0.567(2) 0.5020(14) 0.8144(15) 0.037(3) Uani 1 1 d . . .
N6 N 1.248(3) -0.0727(19) 0.7924(16) 0.063(4) Uani 1 1 d . . .
N7 N -0.1817(17) 0.7975(14) 0.0330(14) 0.050(4) Uani 1 1 d . . .
H7A H -0.2055 0.7475 -0.0110 0.060 Uiso 1 1 calc R . .
H301 H -0.2581 0.8837 0.0508 0.060 Uiso 1 1 calc R . .
C101 C 0.089(2) 0.7331(17) 0.4091(13) 0.037(3) Uani 1 1 d . . .
O101 O 0.0813(16) 0.6095(12) 0.0419(12) 0.045(3) Uani 1 1 d . . .
N10 N 0.3207(16) 0.3990(14) 0.0758(11) 0.034(3) Uani 1 1 d . . .
H208 H 0.2980 0.3386 0.0398 0.040 Uiso 1 1 calc R . .
C1 C 1.049(2) 0.2426(14) 0.9201(14) 0.040(3) Uani 1 1 d . . .
C2 C 0.820(2) 0.2243(12) 0.8157(13) 0.035(3) Uani 1 1 d . . .
C3 C 0.8369(16) 0.2006(15) 0.6944(13) 0.033(3) Uani 1 1 d . . .
C4 C 0.925(2) 0.2602(15) 0.5939(13) 0.036(3) Uani 1 1 d . . .
H209 H 0.9962 0.3238 0.5943 0.043 Uiso 1 1 calc R . .
C5 C 0.7162(15) 0.1112(14) 0.6884(12) 0.035(3) Uani 1 1 d . . .
C6 C 0.691(3) 0.0806(19) 0.5941(18) 0.052(4) Uani 1 1 d . . .
H6 H 0.6104 0.0237 0.5953 0.062 Uiso 1 1 calc R . .
C7 C 0.794(2) 0.1396(16) 0.4898(11) 0.038(3) Uani 1 1 d . . .
C8 C 0.6708(17) 0.1297(11) 0.8843(13) 0.028(3) Uani 1 1 d . . .
C9 C 0.7934(19) 0.4485(13) 0.9075(13) 0.033(3) Uani 1 1 d . . .
N103 N 0.6925(17) 0.5942(11) 0.9261(12) 0.037(3) Uani 1 1 d . . .
H207 H 0.7098 0.6545 0.9649 0.045 Uiso 1 1 calc R . .
C11 C 0.420(3) 0.5031(16) 0.7605(19) 0.049(4) Uani 1 1 d . . .
H11A H 0.3357 0.6027 0.7557 0.073 Uiso 1 1 calc R . .
H11B H 0.3484 0.4365 0.8053 0.073 Uiso 1 1 calc R . .
H11C H 0.4770 0.4707 0.6847 0.073 Uiso 1 1 calc R . .
C12 C 0.7305(19) 0.3876(12) 0.8436(12) 0.027(3) Uani 1 1 d . . .
N105 N 1.1965(18) 0.2004(11) 0.9685(10) 0.036(3) Uani 1 1 d . . .
H10A H 1.2815 0.1162 0.9549 0.043 Uiso 1 1 calc R . .
H300 H 1.2063 0.2574 1.0131 0.043 Uiso 1 1 calc R . .
C14 C 1.137(2) 0.0439(17) 0.8153(16) 0.038(3) Uani 1 1 d . . .
C15 C 0.226(3) 0.851(2) 0.5105(19) 0.059(5) Uani 1 1 d . . .
H15 H 0.2384 0.8686 0.5805 0.071 Uiso 1 1 calc R . .
C16 C 0.323(2) 0.9087(19) 0.4093(15) 0.040(3) Uani 1 1 d . . .
H16 H 0.4017 0.9667 0.4088 0.048 Uiso 1 1 calc R . .
C17 C 0.300(2) 0.8776(13) 0.3054(11) 0.036(3) Uani 1 1 d . . .
C18 C 0.1957(17) 0.7891(11) 0.3070(10) 0.027(3) Uani 1 1 d . . .
C19 C 0.2094(14) 0.7652(13) 0.1840(10) 0.024(3) Uani 1 1 d . . .
C20 C 0.0327(19) 0.8191(15) 0.1469(13) 0.030(3) Uani 1 1 d . . .
C21 C -0.0242(16) 0.7406(13) 0.0742(12) 0.023(2) Uani 1 1 d . . .
C22 C 0.112(2) 0.7681(19) 0.5058(15) 0.037(3) Uani 1 1 d . . .
C23 C 0.3278(18) 0.8649(14) 0.1172(12) 0.030(3) Uani 1 1 d . . .
C24 C -0.112(2) 0.9588(16) 0.1808(15) 0.040(4) Uani 1 1 d . . .
N102 N -0.235(2) 1.0570(18) 0.2162(16) 0.064(5) Uani 1 1 d . . .
C26 C 0.2305(16) 0.5363(13) 0.0898(13) 0.026(3) Uani 1 1 d . . .
N101 N 0.4654(14) 0.3701(13) 0.1331(11) 0.035(3) Uani 1 1 d . . .
C28 C 0.4499(18) 0.4987(15) 0.1802(13) 0.030(3) Uani 1 1 d . . .
C29 C 0.3012(18) 0.6073(16) 0.1578(13) 0.030(3) Uani 1 1 d . . .
C30 C 0.581(3) 0.495(2) 0.253(2) 0.057(5) Uani 1 1 d . . .
H30A H 0.6889 0.4080 0.2396 0.086 Uiso 1 1 calc R . .
H30B H 0.5146 0.4912 0.3323 0.086 Uiso 1 1 calc R . .
H30C H 0.6238 0.5835 0.2328 0.086 Uiso 1 1 calc R . .
H211 H 0.779(12) 0.114(8) 0.424(7) 0.021(17) Uiso 1 1 d . . .
H150 H 0.022(9) 0.692(6) 0.404(5) 0.004(12) Uiso 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
I1 C100 2.052(19) . ?
I2 C22 2.138(19) . ?
N104 N103 1.306(17) . ?
N104 C103 1.357(18) . ?
O2 C8 1.252(18) . ?
N100 C17 1.40(2) . ?
N100 C23 1.401(14) . ?
N100 H212 0.8600 . ?
O4 C23 1.221(17) . ?
O100 C9 1.374(16) . ?
O100 C1 1.424(14) . ?
C102 C1 1.261(19) . ?
C102 C14 1.354(19) . ?
C102 C2 1.566(17) . ?
C100 C7 1.39(2) . ?
C100 C4 1.44(2) . ?
N4 C8 1.289(19) . ?
N4 C5 1.46(2) . ?
N4 H210 0.8600 . ?
C103 C11 1.45(2) . ?
C103 C12 1.456(19) . ?
N6 C14 1.18(2) . ?
N7 C21 1.353(17) . ?
N7 H7A 0.8600 . ?
N7 H301 0.8600 . ?
C101 C22 1.35(2) . ?
C101 C18 1.41(2) . ?
C101 H150 0.75(6) . ?
O101 C21 1.303(15) . ?
O101 C26 1.364(16) . ?
N10 C26 1.277(16) . ?
N10 N101 1.401(14) . ?
N10 H208 0.8600 . ?
C1 N105 1.336(19) . ?
C2 C3 1.50(2) . ?
C2 C12 1.531(15) . ?
C2 C8 1.628(18) . ?
C3 C4 1.35(2) . ?
C3 C5 1.455(14) . ?
C4 H209 0.9300 . ?
C5 C6 1.31(2) . ?
C6 C7 1.42(3) . ?
C6 H6 0.9300 . ?
C7 H211 0.92(9) . ?
C9 C12 1.306(18) . ?
C9 N103 1.370(14) . ?
N103 H207 0.8600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N105 H10A 0.8600 . ?
N105 H300 0.8600 . ?
C15 C22 1.36(2) . ?
C15 C16 1.37(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.417(18) . ?
C16 H16 0.9300 . ?
C17 C18 1.318(18) . ?
C18 C19 1.524(17) . ?
C19 C20 1.455(17) . ?
C19 C29 1.482(17) . ?
C19 C23 1.494(19) . ?
C20 C24 1.465(17) . ?
C20 C21 1.471(16) . ?
C24 N102 1.13(2) . ?
C26 C29 1.447(16) . ?
N101 C28 1.388(19) . ?
C28 C29 1.328(19) . ?
C28 C30 1.50(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
N103 N104 C103 117.5(11) . . ?
C17 N100 C23 108.0(11) . . ?
C17 N100 H212 126.0 . . ?
C23 N100 H212 126.0 . . ?
C9 O100 C1 110.6(10) . . ?
C1 C102 C14 120.2(12) . . ?
C1 C102 C2 123.6(12) . . ?
C14 C102 C2 116.1(12) . . ?
C7 C100 C4 117.2(16) . . ?
C7 C100 I1 122.0(12) . . ?
C4 C100 I1 120.7(11) . . ?
C8 N4 C5 117.1(11) . . ?
C8 N4 H210 121.5 . . ?
C5 N4 H210 121.5 . . ?
N104 C103 C11 124.1(13) . . ?
N104 C103 C12 100.6(12) . . ?
C11 C103 C12 134.6(13) . . ?
C21 N7 H7A 120.0 . . ?
C21 N7 H301 120.0 . . ?
H7A N7 H301 120.0 . . ?
C22 C101 C18 114.5(13) . . ?
C22 C101 H150 128(5) . . ?
C18 C101 H150 118(5) . . ?
C21 O101 C26 118.7(10) . . ?
C26 N10 N101 103.7(10) . . ?
C26 N10 H208 128.2 . . ?
N101 N10 H208 128.2 . . ?
C102 C1 N105 128.5(12) . . ?
C102 C1 O100 127.0(13) . . ?
N105 C1 O100 104.4(11) . . ?
C3 C2 C12 113.8(11) . . ?
C3 C2 C102 115.2(12) . . ?
C12 C2 C102 105.1(10) . . ?
C3 C2 C8 100.5(10) . . ?
C12 C2 C8 108.2(11) . . ?
C102 C2 C8 114.2(10) . . ?
C4 C3 C5 116.5(13) . . ?
C4 C3 C2 131.3(11) . . ?
C5 C3 C2 111.7(12) . . ?
C3 C4 C100 121.6(13) . . ?
C3 C4 H209 119.2 . . ?
C100 C4 H209 119.2 . . ?
C6 C5 C3 125.7(14) . . ?
C6 C5 N4 131.0(12) . . ?
C3 C5 N4 103.3(12) . . ?
C5 C6 C7 115.9(14) . . ?
C5 C6 H6 122.1 . . ?
C7 C6 H6 122.1 . . ?
C100 C7 C6 122.9(14) . . ?
C100 C7 H211 122(5) . . ?
C6 C7 H211 115(5) . . ?
O2 C8 N4 131.1(12) . . ?
O2 C8 C2 121.4(12) . . ?
N4 C8 C2 106.7(12) . . ?
C12 C9 N103 114.1(12) . . ?
C12 C9 O100 129.3(10) . . ?
N103 C9 O100 116.6(12) . . ?
N104 N103 C9 101.5(11) . . ?
N104 N103 H207 129.3 . . ?
C9 N103 H207 129.3 . . ?
C103 C11 H11A 109.5 . . ?
C103 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C103 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 C103 106.2(10) . . ?
C9 C12 C2 122.2(11) . . ?
C103 C12 C2 131.6(12) . . ?
C1 N105 H10A 120.0 . . ?
C1 N105 H300 120.0 . . ?
H10A N105 H300 120.0 . . ?
N6 C14 C102 173.8(19) . . ?
C22 C15 C16 118.2(17) . . ?
C22 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C15 C16 C17 118.3(13) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C18 C17 N100 112.4(10) . . ?
C18 C17 C16 120.3(14) . . ?
N100 C17 C16 127.1(13) . . ?
C17 C18 C101 122.8(12) . . ?
C17 C18 C19 109.0(11) . . ?
C101 C18 C19 128.2(11) . . ?
C20 C19 C29 108.8(9) . . ?
C20 C19 C23 105.3(11) . . ?
C29 C19 C23 111.7(10) . . ?
C20 C19 C18 116.3(9) . . ?
C29 C19 C18 112.8(11) . . ?
C23 C19 C18 101.6(9) . . ?
C19 C20 C24 122.9(11) . . ?
C19 C20 C21 125.0(11) . . ?
C24 C20 C21 112.0(12) . . ?
O101 C21 N7 114.9(10) . . ?
O101 C21 C20 120.8(11) . . ?
N7 C21 C20 124.3(11) . . ?
C101 C22 C15 125.7(18) . . ?
C101 C22 I2 117.5(12) . . ?
C15 C22 I2 116.8(14) . . ?
O4 C23 N100 121.0(13) . . ?
O4 C23 C19 129.6(11) . . ?
N100 C23 C19 108.6(11) . . ?
N102 C24 C20 172(2) . . ?
N10 C26 O101 121.7(10) . . ?
N10 C26 C29 114.9(11) . . ?
O101 C26 C29 123.3(11) . . ?
C28 N101 N10 109.3(11) . . ?
C29 C28 N101 109.7(11) . . ?
C29 C28 C30 130.1(15) . . ?
N101 C28 C30 120.0(13) . . ?
C28 C29 C26 102.4(12) . . ?
C28 C29 C19 136.1(12) . . ?
C26 C29 C19 121.6(11) . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        27.18
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         1.458
_refine_diff_density_min         0.0
_refine_diff_density_rms         0.116
