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

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

data_oche386
_database_code_depnum_ccdc_archive 'CCDC 1428562'
_audit_update_record             
;
2015-09-29 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_audit_creation_date             2014-10-31
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:32:32, GUI svn.r4372)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H14 N6 O6'
_chemical_formula_sum            'C12 H14 N6 O6'
_chemical_formula_weight         338.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H14N6O6
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.22642(18)
_cell_length_b                   9.71725(18)
_cell_length_c                   18.0546(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.6053(19)
_cell_angle_gamma                90.00
_cell_volume                     1585.60(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5140
_cell_measurement_temperature    150
_cell_measurement_theta_max      32.4960
_cell_measurement_theta_min      2.2550
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12718
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         32.93
_diffrn_reflns_theta_min         2.30
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2705
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.8942
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   76.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000  120.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   48.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega    8.00   91.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000 -120.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   86.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega   54.00   81.00   1.0000   22.5000
omega____ theta____ kappa____ phi______ frames
    -       23.6868   77.0000  -60.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0215862000
_diffrn_orient_matrix_UB_12      -0.0533919000
_diffrn_orient_matrix_UB_13      -0.0222791000
_diffrn_orient_matrix_UB_21      0.0540696000
_diffrn_orient_matrix_UB_22      -0.0220351000
_diffrn_orient_matrix_UB_23      0.0314503000
_diffrn_orient_matrix_UB_31      -0.0526615000
_diffrn_orient_matrix_UB_32      -0.0445825000
_diffrn_orient_matrix_UB_33      0.0111169000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4247
_reflns_number_total             5307
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0535P)²+0.4688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1201
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H9 of C9, {H3A,H3B} of C3, H5 of C5
 At 1.5 times of:
  {H4A,H4B,H4C} of C4, {H8A,H8B,H8C} of C8, {H12A,H12B,H12C} of C12
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.47502(9) 0.30228(9) 0.12599(5) 0.02435(18) Uani 1 1 d . . .
O1 O 0.40551(11) 0.51846(10) 0.08815(5) 0.0316(2) Uani 1 1 d . . .
C6 C 0.32225(12) 0.41786(11) 0.19193(6) 0.01804(19) Uani 1 1 d . . .
C5 C 0.33093(11) 0.32585(11) 0.25008(6) 0.01740(19) Uani 1 1 d . . .
H5 H 0.3913 0.2461 0.2598 0.021 Uiso 1 1 calc R . .
N2 N 0.16667(11) 0.49119(10) 0.25858(6) 0.0230(2) Uani 1 1 d . . .
N4 N 0.25163(10) 0.39721(10) 0.42401(5) 0.01982(18) Uani 1 1 d . . .
N6 N 0.36250(11) 0.42060(12) 0.53942(6) 0.0270(2) Uani 1 1 d . . .
C1 C 0.19065(12) 0.31829(11) 0.35710(6) 0.0184(2) Uani 1 1 d . . .
N5 N 0.32241(11) 0.32889(11) 0.48690(6) 0.0252(2) Uani 1 1 d . . .
O3 O 0.42423(11) 0.67387(11) 0.62102(5) 0.0357(2) Uani 1 1 d . . .
N1 N 0.23382(10) 0.37484(9) 0.29032(5) 0.01761(18) Uani 1 1 d . . .
O6 O -0.02922(10) 0.24565(10) 0.28005(5) 0.0298(2) Uani 1 1 d . . .
C10 C 0.31867(12) 0.54754(13) 0.51088(6) 0.0229(2) Uani 1 1 d . . .
O4 O 0.31685(11) 0.78599(10) 0.51522(5) 0.0338(2) Uani 1 1 d . . .
C7 C 0.40384(12) 0.42122(12) 0.12954(6) 0.0208(2) Uani 1 1 d . . .
O5 O -0.04876(10) 0.35227(11) 0.38900(5) 0.0330(2) Uani 1 1 d . . .
C2 C 0.02082(13) 0.30951(11) 0.34476(6) 0.0211(2) Uani 1 1 d . . .
N3 N 0.22175(11) 0.51768(10) 0.19901(6) 0.0233(2) Uani 1 1 d . . .
C9 C 0.24683(13) 0.53338(12) 0.43710(6) 0.0229(2) Uani 1 1 d . . .
H9 H 0.2036 0.6035 0.4030 0.027 Uiso 1 1 calc R . .
C8 C 0.55428(15) 0.28967(16) 0.06445(8) 0.0333(3) Uani 1 1 d . . .
H8A H 0.4873 0.3109 0.0164 0.050 Uiso 1 1 calc R . .
H8B H 0.5914 0.1954 0.0629 0.050 Uiso 1 1 calc R . .
H8C H 0.6376 0.3542 0.0725 0.050 Uiso 1 1 calc R . .
C11 C 0.35906(13) 0.67307(14) 0.55612(7) 0.0269(2) Uani 1 1 d . . .
C3 C -0.18940(16) 0.22772(16) 0.25545(10) 0.0397(3) Uani 1 1 d . . .
H3A H -0.2258 0.2835 0.2096 0.048 Uiso 1 1 calc R . .
H3B H -0.2404 0.2591 0.2957 0.048 Uiso 1 1 calc R . .
C12 C 0.3617(2) 0.91441(17) 0.55378(10) 0.0510(4) Uani 1 1 d . . .
H12A H 0.3328 0.9913 0.5188 0.077 Uiso 1 1 calc R . .
H12B H 0.4693 0.9149 0.5715 0.077 Uiso 1 1 calc R . .
H12C H 0.3133 0.9239 0.5971 0.077 Uiso 1 1 calc R . .
C4 C -0.22166(19) 0.08083(16) 0.23895(11) 0.0470(4) Uani 1 1 d . . .
H4A H -0.1681 0.0496 0.2003 0.070 Uiso 1 1 calc R . .
H4B H -0.3282 0.0687 0.2204 0.070 Uiso 1 1 calc R . .
H4C H -0.1900 0.0267 0.2852 0.070 Uiso 1 1 calc R . .
H1 H 0.2286(15) 0.2271(15) 0.3636(8) 0.018(3) 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
O2 C7 1.3373(14) . ?
O2 C8 1.4530(14) . ?
O1 C7 1.2067(14) . ?
C6 C5 1.3690(14) . ?
C6 C7 1.4757(14) . ?
C6 N3 1.3656(14) . ?
C5 N1 1.3488(13) . ?
N2 N1 1.3593(13) . ?
N2 N3 1.3042(13) . ?
N4 C1 1.4459(14) . ?
N4 N5 1.3631(13) . ?
N4 C9 1.3465(15) . ?
N6 N5 1.2997(15) . ?
N6 C10 1.3663(17) . ?
C1 N1 1.4517(13) . ?
C1 C2 1.5400(16) . ?
O3 C11 1.2048(15) . ?
O6 C2 1.3213(14) . ?
O6 C3 1.4655(16) . ?
C10 C9 1.3702(16) . ?
C10 C11 1.4736(17) . ?
O4 C11 1.3360(17) . ?
O4 C12 1.4482(18) . ?
O5 C2 1.1955(14) . ?
C3 C4 1.476(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C8 115.92(10) . . ?
C5 C6 C7 129.77(10) . . ?
N3 C6 C5 109.16(9) . . ?
N3 C6 C7 121.07(10) . . ?
N1 C5 C6 103.88(9) . . ?
N3 N2 N1 106.96(9) . . ?
N5 N4 C1 118.58(9) . . ?
C9 N4 C1 130.30(10) . . ?
C9 N4 N5 111.08(9) . . ?
N5 N6 C10 108.95(10) . . ?
N4 C1 N1 111.56(9) . . ?
N4 C1 C2 111.34(9) . . ?
N1 C1 C2 110.00(9) . . ?
N6 N5 N4 106.98(10) . . ?
C5 N1 N2 111.24(9) . . ?
C5 N1 C1 129.55(9) . . ?
N2 N1 C1 119.15(9) . . ?
C2 O6 C3 118.39(10) . . ?
N6 C10 C9 108.94(11) . . ?
N6 C10 C11 121.04(10) . . ?
C9 C10 C11 129.86(12) . . ?
C11 O4 C12 114.76(11) . . ?
O2 C7 C6 110.38(9) . . ?
O1 C7 O2 125.42(10) . . ?
O1 C7 C6 124.20(11) . . ?
O6 C2 C1 108.56(9) . . ?
O5 C2 C1 123.48(11) . . ?
O5 C2 O6 127.94(11) . . ?
N2 N3 C6 108.76(9) . . ?
N4 C9 C10 104.05(10) . . ?
O3 C11 C10 124.44(13) . . ?
O3 C11 O4 124.42(12) . . ?
O4 C11 C10 111.13(10) . . ?
O6 C3 C4 109.04(12) . . ?

_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_oche523
_database_code_depnum_ccdc_archive 'CCDC 1428563'
_audit_update_record             
;
2015-09-29 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_audit_creation_date             2015-04-19
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:32:32, GUI svn.r4372)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C31 H25 N9 O6'
_chemical_formula_sum            'C31 H25 N9 O6'
_chemical_formula_weight         619.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         C31H25N9O6
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6712(4)
_cell_length_b                   12.4890(8)
_cell_length_c                   17.0137(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.677(4)
_cell_angle_gamma                90.00
_cell_volume                     2986.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5926
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.0790
_cell_measurement_theta_min      2.4950
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16696
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         29.53
_diffrn_reflns_theta_min         2.05
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2705
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.8353
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   12.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805  -57.0000  150.0000 60

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   82.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805   77.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega   28.00   65.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805 -124.0000 -142.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   24.00   1.0000  125.0000
omega____ theta____ kappa____ phi______ frames
    -       15.2805  -77.0000  -90.0000 74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0468092000
_diffrn_orient_matrix_UB_12      -0.0121332000
_diffrn_orient_matrix_UB_13      0.0011600000
_diffrn_orient_matrix_UB_21      0.0089439000
_diffrn_orient_matrix_UB_22      -0.0552926000
_diffrn_orient_matrix_UB_23      -0.0037715000
_diffrn_orient_matrix_UB_31      0.0165672000
_diffrn_orient_matrix_UB_32      -0.0044561000
_diffrn_orient_matrix_UB_33      0.0433489000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4764
_reflns_number_total             6959
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0531P)²+0.9768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1298
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H22 of C22, H12 of C12, H19 of C19, H8 of C8, H10 of C10, H9 of C9, H11 of
  C11, H1 of C1, H2 of C2, {H25A,H25B} of C25, {H5A,H5B} of C5, H7 of C7, H29
  of C29, H31 of C31, H30 of C30, {H15A,H15B} of C15, H28 of C28, H27 of C27,
  H17 of C17, H21 of C21, H20 of C20, H18 of C18
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C5(H5A,H5B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C22(H22), C11(H11), C2(H2), C7(H7), C29(H29), C31(H31), C30(H30),
 C28(H28), C27(H27), C17(H17), C21(H21), C20(H20), C18(H18), C19(H19), C8(H8),
 C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O4 O 0.21725(9) 0.17554(10) 0.01857(7) 0.0499(3) Uani 1 1 d . . .
N7 N 0.21501(9) 0.42704(11) 0.17643(8) 0.0355(3) Uani 1 1 d . . .
N4 N 0.22461(9) 0.60826(10) 0.13613(8) 0.0353(3) Uani 1 1 d . . .
N1 N 0.08295(9) 0.54605(11) 0.16282(8) 0.0355(3) Uani 1 1 d . . .
O2 O -0.22456(8) 0.60815(11) 0.09796(8) 0.0509(3) Uani 1 1 d . . .
N8 N 0.27449(11) 0.37960(12) 0.24399(8) 0.0476(4) Uani 1 1 d . . .
C13 C 0.26291(12) 0.69835(13) 0.04406(11) 0.0399(4) Uani 1 1 d . . .
O5 O 0.31824(10) 0.82289(11) -0.03782(9) 0.0633(4) Uani 1 1 d . . .
C12 C 0.19728(12) 0.62812(13) 0.05533(10) 0.0386(4) Uani 1 1 d . . .
H12 H 0.1451 0.6001 0.0159 0.046 Uiso 1 1 calc R . .
C22 C 0.20140(12) 0.36342(13) 0.11020(10) 0.0378(4) Uani 1 1 d . . .
H22 H 0.1652 0.3776 0.0567 0.045 Uiso 1 1 calc R . .
O6 O 0.20722(11) 0.69990(11) -0.09616(8) 0.0584(4) Uani 1 1 d . . .
N3 N -0.05887(10) 0.52571(14) 0.08584(9) 0.0528(4) Uani 1 1 d . . .
N6 N 0.32804(11) 0.71773(13) 0.11779(10) 0.0537(4) Uani 1 1 d . . .
C24 C 0.26379(12) 0.17357(14) 0.09799(10) 0.0400(4) Uani 1 1 d . . .
O3 O 0.30946(11) 0.09887(10) 0.13347(8) 0.0610(4) Uani 1 1 d . . .
N9 N 0.29616(11) 0.28665(12) 0.22078(9) 0.0495(4) Uani 1 1 d . . .
N2 N 0.02814(11) 0.49518(15) 0.09533(10) 0.0558(4) Uani 1 1 d . . .
C26 C 0.14152(14) 0.01408(16) -0.05267(12) 0.0514(5) Uani 1 1 d . . .
C3 C -0.06061(11) 0.59603(13) 0.14619(9) 0.0363(4) Uani 1 1 d . . .
C23 C 0.25234(11) 0.27393(13) 0.13912(9) 0.0359(4) Uani 1 1 d . . .
C1 C 0.18588(11) 0.53622(12) 0.18516(9) 0.0349(4) Uani 1 1 d . . .
H1 H 0.2115 0.5569 0.2429 0.042 Uiso 1 1 calc R . .
N5 N 0.30565(10) 0.66290(13) 0.17409(10) 0.0504(4) Uani 1 1 d . . .
C14 C 0.26789(13) 0.74907(14) -0.03293(12) 0.0468(4) Uani 1 1 d . . .
C6 C -0.38442(12) 0.63538(15) 0.01695(11) 0.0454(4) Uani 1 1 d . . .
C11 C -0.43973(14) 0.72063(18) -0.02085(14) 0.0614(5) Uani 1 1 d . . .
H11 H -0.4357 0.7856 0.0067 0.074 Uiso 1 1 calc R . .
C2 C 0.02973(12) 0.60980(13) 0.19534(10) 0.0395(4) Uani 1 1 d . . .
H2 H 0.0500 0.6536 0.2412 0.047 Uiso 1 1 calc R . .
C25 C 0.22847(15) 0.08238(17) -0.03029(12) 0.0582(5) Uani 1 1 d . . .
H25A H 0.2822 0.0401 0.0007 0.070 Uiso 1 1 calc R . .
H25B H 0.2419 0.1067 -0.0800 0.070 Uiso 1 1 calc R . .
C5 C -0.31737(13) 0.64742(19) 0.10107(12) 0.0563(5) Uani 1 1 d . . .
H5A H -0.3129 0.7220 0.1177 0.068 Uiso 1 1 calc R . .
H5B H -0.3396 0.6062 0.1403 0.068 Uiso 1 1 calc R . .
C7 C -0.39298(14) 0.53965(18) -0.02416(14) 0.0597(5) Uani 1 1 d . . .
H7 H -0.3574 0.4809 0.0009 0.072 Uiso 1 1 calc R . .
O1 O -0.15029(10) 0.71102(12) 0.20519(9) 0.0633(4) Uani 1 1 d . . .
C4 C -0.14908(12) 0.64523(14) 0.15423(10) 0.0409(4) Uani 1 1 d . . .
C29 C -0.0155(3) -0.1134(3) -0.1061(3) 0.1187(15) Uani 1 1 d . . .
H29 H -0.0678 -0.1583 -0.1250 0.142 Uiso 1 1 calc R . .
C31 C 0.07697(18) 0.0283(2) -0.12921(15) 0.0804(7) Uani 1 1 d . . .
H31 H 0.0872 0.0824 -0.1633 0.097 Uiso 1 1 calc R . .
C16 C 0.14565(15) 0.66584(15) -0.23973(11) 0.0491(5) Uani 1 1 d . . .
C30 C -0.0009(2) -0.0352(4) -0.1554(2) 0.1171(13) Uani 1 1 d . . .
H30 H -0.0437 -0.0247 -0.2070 0.141 Uiso 1 1 calc R . .
C15 C 0.19826(18) 0.74489(18) -0.17689(12) 0.0671(6) Uani 1 1 d . . .
H15A H 0.2608 0.7585 -0.1835 0.081 Uiso 1 1 calc R . .
H15B H 0.1637 0.8121 -0.1834 0.081 Uiso 1 1 calc R . .
C28 C 0.0454(3) -0.1290(2) -0.0279(3) 0.1133(13) Uani 1 1 d . . .
H28 H 0.0333 -0.1821 0.0062 0.136 Uiso 1 1 calc R . .
C27 C 0.12603(19) -0.06261(18) -0.00137(18) 0.0748(7) Uani 1 1 d . . .
H27 H 0.1682 -0.0712 0.0507 0.090 Uiso 1 1 calc R . .
C17 C 0.19392(16) 0.58423(17) -0.26503(14) 0.0608(5) Uani 1 1 d . . .
H17 H 0.2592 0.5771 -0.2416 0.073 Uiso 1 1 calc R . .
C21 C 0.04943(18) 0.67353(18) -0.27559(16) 0.0730(7) Uani 1 1 d . . .
H21 H 0.0153 0.7277 -0.2592 0.088 Uiso 1 1 calc R . .
C20 C 0.0025(2) 0.6027(2) -0.33530(19) 0.0929(9) Uani 1 1 d . . .
H20 H -0.0628 0.6093 -0.3590 0.111 Uiso 1 1 calc R . .
C18 C 0.1464(2) 0.51297(18) -0.32477(16) 0.0748(7) Uani 1 1 d . . .
H18 H 0.1795 0.4579 -0.3412 0.090 Uiso 1 1 calc R . .
C19 C 0.0509(2) 0.5236(2) -0.35958(16) 0.0839(8) Uani 1 1 d . . .
H19 H 0.0189 0.4760 -0.4002 0.101 Uiso 1 1 calc R . .
C8 C -0.45412(17) 0.5298(2) -0.10259(16) 0.0780(7) Uani 1 1 d . . .
H8 H -0.4592 0.4650 -0.1304 0.094 Uiso 1 1 calc R . .
C10 C -0.50069(17) 0.7107(2) -0.09874(15) 0.0774(7) Uani 1 1 d . . .
H10 H -0.5374 0.7688 -0.1236 0.093 Uiso 1 1 calc R . .
C9 C -0.50732(16) 0.6166(3) -0.13917(15) 0.0811(8) Uani 1 1 d . . .
H9 H -0.5481 0.6104 -0.1921 0.097 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
O4 C24 1.328(2) . ?
O4 C25 1.466(2) . ?
N7 N8 1.3632(18) . ?
N7 C22 1.346(2) . ?
N7 C1 1.449(2) . ?
N4 C12 1.340(2) . ?
N4 C1 1.449(2) . ?
N4 N5 1.3623(18) . ?
N1 N2 1.3560(18) . ?
N1 C1 1.453(2) . ?
N1 C2 1.341(2) . ?
O2 C5 1.462(2) . ?
O2 C4 1.323(2) . ?
N8 N9 1.295(2) . ?
C13 C12 1.356(2) . ?
C13 N6 1.363(2) . ?
C13 C14 1.476(3) . ?
O5 C14 1.199(2) . ?
C12 H12 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.356(2) . ?
O6 C14 1.333(2) . ?
O6 C15 1.455(2) . ?
N3 N2 1.297(2) . ?
N3 C3 1.357(2) . ?
N6 N5 1.294(2) . ?
C24 O3 1.205(2) . ?
C24 C23 1.468(2) . ?
N9 C23 1.362(2) . ?
C26 C25 1.490(3) . ?
C26 C31 1.384(3) . ?
C26 C27 1.358(3) . ?
C3 C2 1.360(2) . ?
C3 C4 1.477(2) . ?
C1 H1 0.9800 . ?
C6 C11 1.381(3) . ?
C6 C5 1.494(3) . ?
C6 C7 1.373(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.375(3) . ?
C2 H2 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.383(3) . ?
O1 C4 1.198(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.344(5) . ?
C29 C28 1.388(5) . ?
C31 H31 0.9300 . ?
C31 C30 1.356(4) . ?
C16 C15 1.497(3) . ?
C16 C17 1.379(3) . ?
C16 C21 1.371(3) . ?
C30 H30 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C28 H28 0.9300 . ?
C28 C27 1.409(4) . ?
C27 H27 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.380(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.374(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.349(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.362(4) . ?
C19 H19 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.376(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.351(4) . ?
C9 H9 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
C24 O4 C25 116.97(14) . . ?
N8 N7 C1 117.31(12) . . ?
C22 N7 N8 110.77(13) . . ?
C22 N7 C1 131.60(13) . . ?
C12 N4 C1 130.85(13) . . ?
C12 N4 N5 110.91(14) . . ?
N5 N4 C1 118.11(13) . . ?
N2 N1 C1 120.08(13) . . ?
C2 N1 N2 110.71(13) . . ?
C2 N1 C1 128.82(13) . . ?
C4 O2 C5 116.82(14) . . ?
N9 N8 N7 106.63(13) . . ?
C12 C13 N6 108.87(15) . . ?
C12 C13 C14 128.40(16) . . ?
N6 C13 C14 122.73(15) . . ?
N4 C12 C13 104.43(14) . . ?
N4 C12 H12 127.8 . . ?
C13 C12 H12 127.8 . . ?
N7 C22 H22 127.8 . . ?
N7 C22 C23 104.41(14) . . ?
C23 C22 H22 127.8 . . ?
C14 O6 C15 116.27(15) . . ?
N2 N3 C3 109.12(14) . . ?
N5 N6 C13 109.11(14) . . ?
O4 C24 C23 111.93(14) . . ?
O3 C24 O4 125.01(16) . . ?
O3 C24 C23 123.05(16) . . ?
N8 N9 C23 109.29(13) . . ?
N3 N2 N1 106.91(14) . . ?
C31 C26 C25 118.1(2) . . ?
C27 C26 C25 121.9(2) . . ?
C27 C26 C31 120.0(2) . . ?
N3 C3 C2 108.69(15) . . ?
N3 C3 C4 123.17(14) . . ?
C2 C3 C4 128.13(15) . . ?
C22 C23 C24 131.08(15) . . ?
C22 C23 N9 108.87(14) . . ?
N9 C23 C24 120.03(14) . . ?
N7 C1 N1 111.57(12) . . ?
N7 C1 H1 108.1 . . ?
N4 C1 N7 110.44(13) . . ?
N4 C1 N1 110.29(12) . . ?
N4 C1 H1 108.1 . . ?
N1 C1 H1 108.1 . . ?
N6 N5 N4 106.66(14) . . ?
O5 C14 C13 125.46(18) . . ?
O5 C14 O6 125.46(18) . . ?
O6 C14 C13 109.08(15) . . ?
C11 C6 C5 120.41(18) . . ?
C7 C6 C11 118.61(18) . . ?
C7 C6 C5 120.98(18) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
N1 C2 C3 104.56(14) . . ?
N1 C2 H2 127.7 . . ?
C3 C2 H2 127.7 . . ?
O4 C25 C26 111.83(16) . . ?
O4 C25 H25A 109.3 . . ?
O4 C25 H25B 109.3 . . ?
C26 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
O2 C5 C6 107.20(15) . . ?
O2 C5 H5A 110.3 . . ?
O2 C5 H5B 110.3 . . ?
C6 C5 H5A 110.3 . . ?
C6 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.5(2) . . ?
C8 C7 H7 119.7 . . ?
O2 C4 C3 111.26(14) . . ?
O1 C4 O2 125.50(16) . . ?
O1 C4 C3 123.23(16) . . ?
C30 C29 H29 119.1 . . ?
C30 C29 C28 121.8(3) . . ?
C28 C29 H29 119.1 . . ?
C26 C31 H31 119.4 . . ?
C30 C31 C26 121.2(3) . . ?
C30 C31 H31 119.4 . . ?
C17 C16 C15 120.3(2) . . ?
C21 C16 C15 121.7(2) . . ?
C21 C16 C17 117.9(2) . . ?
C29 C30 C31 119.3(4) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
O6 C15 C16 107.94(16) . . ?
O6 C15 H15A 110.1 . . ?
O6 C15 H15B 110.1 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
C29 C28 H28 120.8 . . ?
C29 C28 C27 118.3(3) . . ?
C27 C28 H28 120.8 . . ?
C26 C27 C28 119.3(3) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C21 H21 119.4 . . ?
C16 C21 C20 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.5(2) . . ?
C9 C8 H8 120.2 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
