# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_201408170
_database_code_depnum_ccdc_archive 'CCDC 1024177'
_audit_update_record             
;
2014-09-14 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;
_audit_creation_date             2014-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H14 N2 O3'
_chemical_formula_sum            'C14 H14 N2 O3'
_chemical_formula_weight         258.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 '-x, -y, -z'
4 'x, -y, z-1/2'

_cell_length_a                   12.8276(3)
_cell_length_b                   8.4882(2)
_cell_length_c                   24.8068(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.044(2)
_cell_angle_gamma                90.00
_cell_volume                     2700.61(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.7930
_cell_measurement_theta_min      3.4460
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10232
_diffrn_reflns_theta_full        72.43
_diffrn_reflns_theta_max         72.43
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -71.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega  -70.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   29.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -120.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   -4.00   26.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega  -12.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
  8 omega   14.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
  9 omega  -15.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000    0.0000 74

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00   87.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega   44.00   85.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
 13 omega   46.00   84.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 14 omega   55.00   92.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 15 omega   64.00   90.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   96.00  154.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00   97.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
 18 omega   63.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000 -180.0000 111

#__ type_ start__ end____ width___ exp.time_
 19 omega  -70.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  -30.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0904818000
_diffrn_orient_matrix_UB_12      -0.1017072000
_diffrn_orient_matrix_UB_13      0.0222185000
_diffrn_orient_matrix_UB_21      -0.0125892000
_diffrn_orient_matrix_UB_22      0.0753109000
_diffrn_orient_matrix_UB_23      0.0560047000
_diffrn_orient_matrix_UB_31      -0.0779698000
_diffrn_orient_matrix_UB_32      -0.1301402000
_diffrn_orient_matrix_UB_33      0.0150723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3823
_reflns_number_total             5224
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.026
_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)+(0.0653P)²+0.2905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1417
_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:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C1'(H1'),
 C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C9'(H9'), C10'(H10'), C11'(H11')
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C13'(H13D,H13E,H13F), C14'(H14D,
 H14E,H14F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.90201(11) 0.37593(16) 0.62853(6) 0.0751(4) Uani 1 d . . .
O2 O 0.84975(13) 0.44343(19) 0.74621(6) 0.0842(4) Uani 1 d . . .
O3 O 0.65276(11) 0.3794(2) 0.58977(6) 0.0778(4) Uani 1 d . . .
N1 N 0.80212(11) 0.16777(17) 0.65335(6) 0.0558(3) Uani 1 d . . .
N2 N 0.82307(11) 0.31256(17) 0.64863(6) 0.0537(3) Uani 1 d . . .
C1 C 0.84849(16) -0.0977(2) 0.64982(8) 0.0660(5) Uani 1 d . . .
H1 H 0.7912 -0.1145 0.6715 0.079 Uiso 1 calc . . R
C2 C 0.9092(2) -0.2243(2) 0.63466(10) 0.0781(6) Uani 1 d . . .
H2 H 0.8933 -0.3249 0.6468 0.094 Uiso 1 calc . . R
C3 C 0.99223(17) -0.2024(3) 0.60196(10) 0.0756(6) Uani 1 d . . .
H3 H 1.0337 -0.2874 0.5923 0.091 Uiso 1 calc . . R
C4 C 1.01425(17) -0.0536(3) 0.58336(10) 0.0802(6) Uani 1 d . . .
H4 H 1.0696 -0.0395 0.5601 0.096 Uiso 1 calc . . R
C5 C 0.95573(16) 0.0757(2) 0.59847(9) 0.0712(5) Uani 1 d . . .
H5 H 0.9718 0.1757 0.5858 0.085 Uiso 1 calc . . R
C6 C 0.87194(13) 0.0538(2) 0.63314(7) 0.0545(4) Uani 1 d . . .
C7 C 0.74495(14) 0.4206(2) 0.66967(8) 0.0578(4) Uani 1 d . . .
C8 C 0.76272(16) 0.4922(3) 0.71903(8) 0.0680(5) Uani 1 d . . .
C9 C 0.6930(2) 0.6058(3) 0.73639(11) 0.0886(7) Uani 1 d . . .
H9 H 0.7029 0.6558 0.7695 0.106 Uiso 1 calc . . R
C10 C 0.6089(2) 0.6428(3) 0.70347(13) 0.1006(8) Uani 1 d . . .
H10 H 0.5627 0.7199 0.7148 0.121 Uiso 1 calc . . R
C11 C 0.59042(18) 0.5712(3) 0.65480(12) 0.0899(7) Uani 1 d . . .
H11 H 0.5322 0.5983 0.6339 0.108 Uiso 1 calc . . R
C12 C 0.65946(14) 0.4580(2) 0.63710(9) 0.0668(5) Uani 1 d . . .
C13 C 0.8838(2) 0.5317(4) 0.79221(11) 0.1081(9) Uani 1 d . . .
H13A H 0.8984 0.6381 0.7816 0.162 Uiso 1 calc . . GR
H13B H 0.9458 0.4847 0.8073 0.162 Uiso 1 calc . . GR
H13C H 0.8300 0.5317 0.8186 0.162 Uiso 1 calc . . GR
C14 C 0.56824(19) 0.4155(4) 0.55360(12) 0.1068(10) Uani 1 d . . .
H14A H 0.5725 0.3501 0.5221 0.160 Uiso 1 calc . . GR
H14B H 0.5721 0.5243 0.5432 0.160 Uiso 1 calc . . GR
H14C H 0.5034 0.3964 0.5711 0.160 Uiso 1 calc . . GR
O1' O 0.73461(11) 0.12596(16) 0.45453(6) 0.0710(4) Uani 1 d . . .
O2' O 0.48954(12) 0.1315(2) 0.43700(8) 0.0979(6) Uani 1 d . . .
O3' O 0.77704(15) 0.0528(2) 0.33001(6) 0.0902(5) Uani 1 d . . .
N1' N 0.68597(12) 0.33340(18) 0.40146(6) 0.0610(4) Uani 1 d . . .
N2' N 0.68805(11) 0.18983(18) 0.41514(6) 0.0575(4) Uani 1 d . . .
C1' C 0.73060(17) 0.5976(2) 0.41172(9) 0.0696(5) Uani 1 d . . .
H1' H 0.6902 0.6137 0.3807 0.083 Uiso 1 calc . . R
C2' C 0.7785(2) 0.7236(3) 0.43638(10) 0.0888(7) Uani 1 d . . .
H2' H 0.7707 0.8241 0.4219 0.107 Uiso 1 calc . . R
C3' C 0.8376(2) 0.7019(3) 0.48217(10) 0.0866(7) Uani 1 d . . .
H3' H 0.8698 0.7874 0.4989 0.104 Uiso 1 calc . . R
C4' C 0.84912(18) 0.5544(3) 0.50328(9) 0.0773(6) Uani 1 d . . .
H4' H 0.8894 0.5406 0.5345 0.093 Uiso 1 calc . . R
C5' C 0.80234(15) 0.4251(2) 0.47928(8) 0.0661(5) Uani 1 d . . .
H5' H 0.8111 0.3252 0.4941 0.079 Uiso 1 calc . . R
C6' C 0.74165(13) 0.4462(2) 0.43241(7) 0.0542(4) Uani 1 d . . .
C7' C 0.62758(16) 0.0837(2) 0.38069(8) 0.0678(5) Uani 1 d . . .
C8' C 0.52607(19) 0.0511(3) 0.39421(11) 0.0843(7) Uani 1 d . . .
C9' C 0.4715(2) -0.0613(4) 0.36330(14) 0.1180(13) Uani 1 d . . .
H9' H 0.4027 -0.0858 0.3708 0.142 Uiso 1 calc . . R
C10' C 0.5217(4) -0.1347(4) 0.32163(15) 0.1338(15) Uani 1 d . . .
H10' H 0.4854 -0.2100 0.3016 0.161 Uiso 1 calc . . R
C11' C 0.6220(3) -0.1023(3) 0.30833(11) 0.1145(11) Uani 1 d . . .
H11' H 0.6529 -0.1542 0.2797 0.137 Uiso 1 calc . . R
C12' C 0.6775(2) 0.0096(3) 0.33820(9) 0.0801(6) Uani 1 d . . .
C13' C 0.3865(2) 0.0963(5) 0.45530(16) 0.1472(16) Uani 1 d . . .
H13D H 0.3367 0.1175 0.4269 0.221 Uiso 1 calc . . GR
H13E H 0.3713 0.1607 0.4860 0.221 Uiso 1 calc . . GR
H13F H 0.3827 -0.0128 0.4652 0.221 Uiso 1 calc . . GR
C14' C 0.8394(3) -0.0402(4) 0.29471(12) 0.1292(12) Uani 1 d . . .
H14D H 0.8073 -0.0425 0.2595 0.194 Uiso 1 calc . . GR
H14E H 0.8449 -0.1456 0.3085 0.194 Uiso 1 calc . . GR
H14F H 0.9077 0.0053 0.2925 0.194 Uiso 1 calc . . GR


_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 N2 1.2576(18) . ?
O2 C8 1.358(3) . ?
O2 C13 1.427(3) . ?
O3 C12 1.352(3) . ?
O3 C14 1.428(3) . ?
N1 N2 1.264(2) . ?
N1 C6 1.416(2) . ?
N2 C7 1.462(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(3) . ?
C1 C6 1.386(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.401(3) . ?
C7 C8 1.382(3) . ?
C7 C12 1.387(3) . ?
C8 C9 1.389(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1' N2' 1.2588(18) . ?
O2' C8' 1.353(3) . ?
O2' C13' 1.437(3) . ?
O3' C12' 1.347(3) . ?
O3' C14' 1.433(3) . ?
N1' N2' 1.265(2) . ?
N1' C6' 1.413(2) . ?
N2' C7' 1.456(2) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.372(3) . ?
C1' C6' 1.390(3) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.367(3) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.364(3) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.380(3) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.399(3) . ?
C7' C8' 1.379(3) . ?
C7' C12' 1.393(3) . ?
C8' C9' 1.403(4) . ?
C9' H9' 0.9300 . ?
C9' C10' 1.377(5) . ?
C10' H10' 0.9300 . ?
C10' C11' 1.362(5) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.393(3) . ?
C13' H13D 0.9600 . ?
C13' H13E 0.9600 . ?
C13' H13F 0.9600 . ?
C14' H14D 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H14F 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
C8 O2 C13 118.3(2) . . ?
C12 O3 C14 118.39(19) . . ?
N2 N1 C6 119.64(15) . . ?
O1 N2 N1 128.81(15) . . ?
O1 N2 C7 115.81(14) . . ?
N1 N2 C7 115.38(14) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C6 120.9(2) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.13(19) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 N1 112.72(16) . . ?
C1 C6 C5 118.64(18) . . ?
C5 C6 N1 128.61(16) . . ?
C8 C7 N2 119.28(16) . . ?
C8 C7 C12 122.09(19) . . ?
C12 C7 N2 118.38(18) . . ?
O2 C8 C7 115.25(18) . . ?
O2 C8 C9 125.8(2) . . ?
C7 C8 C9 118.9(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 H10 118.5 . . ?
C11 C10 C9 122.9(2) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.1(2) . . ?
C12 C11 H11 120.4 . . ?
O3 C12 C7 115.48(18) . . ?
O3 C12 C11 126.0(2) . . ?
C11 C12 C7 118.5(2) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8' O2' C13' 118.5(3) . . ?
C12' O3' C14' 118.9(2) . . ?
N2' N1' C6' 119.94(15) . . ?
O1' N2' N1' 129.09(15) . . ?
O1' N2' C7' 115.43(15) . . ?
N1' N2' C7' 115.48(14) . . ?
C2' C1' H1' 119.5 . . ?
C2' C1' C6' 121.0(2) . . ?
C6' C1' H1' 119.5 . . ?
C1' C2' H2' 119.9 . . ?
C3' C2' C1' 120.1(2) . . ?
C3' C2' H2' 119.9 . . ?
C2' C3' H3' 120.1 . . ?
C4' C3' C2' 119.9(2) . . ?
C4' C3' H3' 120.1 . . ?
C3' C4' H4' 119.3 . . ?
C3' C4' C5' 121.4(2) . . ?
C5' C4' H4' 119.3 . . ?
C4' C5' H5' 120.4 . . ?
C4' C5' C6' 119.18(19) . . ?
C6' C5' H5' 120.4 . . ?
C1' C6' N1' 112.25(16) . . ?
C1' C6' C5' 118.48(17) . . ?
C5' C6' N1' 129.26(17) . . ?
C8' C7' N2' 118.5(2) . . ?
C8' C7' C12' 122.9(2) . . ?
C12' C7' N2' 118.43(19) . . ?
O2' C8' C7' 115.6(2) . . ?
O2' C8' C9' 126.6(3) . . ?
C7' C8' C9' 117.8(3) . . ?
C8' C9' H9' 120.6 . . ?
C10' C9' C8' 118.9(3) . . ?
C10' C9' H9' 120.6 . . ?
C9' C10' H10' 118.4 . . ?
C11' C10' C9' 123.2(3) . . ?
C11' C10' H10' 118.4 . . ?
C10' C11' H11' 120.5 . . ?
C10' C11' C12' 119.0(3) . . ?
C12' C11' H11' 120.5 . . ?
O3' C12' C7' 116.18(18) . . ?
O3' C12' C11' 125.6(3) . . ?
C11' C12' C7' 118.2(3) . . ?
O2' C13' H13D 109.5 . . ?
O2' C13' H13E 109.5 . . ?
O2' C13' H13F 109.5 . . ?
H13D C13' H13E 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
O3' C14' H14D 109.5 . . ?
O3' C14' H14E 109.5 . . ?
O3' C14' H14F 109.5 . . ?
H14D C14' H14E 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C7 C8 -77.4(2) . . . . ?
O1 N2 C7 C12 97.1(2) . . . . ?
O2 C8 C9 C10 179.3(2) . . . . ?
N1 N2 C7 C8 102.3(2) . . . . ?
N1 N2 C7 C12 -83.2(2) . . . . ?
N2 N1 C6 C1 168.93(16) . . . . ?
N2 N1 C6 C5 -13.3(3) . . . . ?
N2 C7 C8 O2 -5.5(3) . . . . ?
N2 C7 C8 C9 173.93(18) . . . . ?
N2 C7 C12 O3 5.1(3) . . . . ?
N2 C7 C12 C11 -174.07(18) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C1 C6 N1 -179.07(18) . . . . ?
C2 C1 C6 C5 2.9(3) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 N1 -179.64(19) . . . . ?
C4 C5 C6 C1 -2.0(3) . . . . ?
C6 N1 N2 O1 -1.6(3) . . . . ?
C6 N1 N2 C7 178.67(14) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C7 C8 C9 C10 -0.1(4) . . . . ?
C8 C7 C12 O3 179.45(18) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 O3 -178.7(2) . . . . ?
C10 C11 C12 C7 0.3(3) . . . . ?
C12 C7 C8 O2 -179.86(18) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
C13 O2 C8 C7 168.4(2) . . . . ?
C13 O2 C8 C9 -11.0(3) . . . . ?
C14 O3 C12 C7 -178.24(19) . . . . ?
C14 O3 C12 C11 0.8(3) . . . . ?
O1' N2' C7' C8' 86.9(2) . . . . ?
O1' N2' C7' C12' -87.9(2) . . . . ?
O2' C8' C9' C10' -178.6(3) . . . . ?
N1' N2' C7' C8' -92.7(2) . . . . ?
N1' N2' C7' C12' 92.5(2) . . . . ?
N2' N1' C6' C1' -179.88(18) . . . . ?
N2' N1' C6' C5' -0.7(3) . . . . ?
N2' C7' C8' O2' 4.6(3) . . . . ?
N2' C7' C8' C9' -174.79(19) . . . . ?
N2' C7' C12' O3' -5.1(3) . . . . ?
N2' C7' C12' C11' 174.38(19) . . . . ?
C1' C2' C3' C4' 0.2(4) . . . . ?
C2' C1' C6' N1' 179.7(2) . . . . ?
C2' C1' C6' C5' 0.4(3) . . . . ?
C2' C3' C4' C5' 0.1(4) . . . . ?
C3' C4' C5' C6' -0.2(4) . . . . ?
C4' C5' C6' N1' -179.25(19) . . . . ?
C4' C5' C6' C1' -0.1(3) . . . . ?
C6' N1' N2' O1' 0.1(3) . . . . ?
C6' N1' N2' C7' 179.64(16) . . . . ?
C6' C1' C2' C3' -0.4(4) . . . . ?
C7' C8' C9' C10' 0.7(4) . . . . ?
C8' C7' C12' O3' -179.57(19) . . . . ?
C8' C7' C12' C11' -0.1(3) . . . . ?
C8' C9' C10' C11' -0.8(5) . . . . ?
C9' C10' C11' C12' 0.3(5) . . . . ?
C10' C11' C12' O3' 179.5(3) . . . . ?
C10' C11' C12' C7' 0.1(4) . . . . ?
C12' C7' C8' O2' 179.1(2) . . . . ?
C12' C7' C8' C9' -0.3(3) . . . . ?
C13' O2' C8' C7' -176.3(2) . . . . ?
C13' O2' C8' C9' 3.0(4) . . . . ?
C14' O3' C12' C7' 167.4(2) . . . . ?
C14' O3' C12' C11' -12.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_201409196a
_database_code_depnum_ccdc_archive 'CCDC 1026842'
_audit_update_record             
;
2014-09-30 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;
_audit_creation_date             2014-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H21 F3 N4 O6 Pd2'
_chemical_formula_sum            'C28 H21 F3 N4 O6 Pd2'
_chemical_formula_weight         779.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Pd1F3
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'
F F 0.0171 0.0103 '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'
Pd Pd -0.9988 1.0072 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.4863(4)
_cell_length_b                   17.2032(5)
_cell_length_c                   11.5651(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.969(4)
_cell_angle_gamma                90.00
_cell_volume                     2770.92(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3752
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.1690
_cell_measurement_theta_min      3.5460
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12566
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   13.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1323  -99.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   65.00   95.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104  178.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega   64.00   96.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104  178.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00   91.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104    0.0000  150.0000 134

#__ type_ start__ end____ width___ exp.time_
  5 omega  -53.00  -28.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104  -37.0000  -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0250054000
_diffrn_orient_matrix_UB_12      0.0355509000
_diffrn_orient_matrix_UB_13      -0.0162596000
_diffrn_orient_matrix_UB_21      0.0062682000
_diffrn_orient_matrix_UB_22      0.0086849000
_diffrn_orient_matrix_UB_23      0.0616507000
_diffrn_orient_matrix_UB_31      0.0439258000
_diffrn_orient_matrix_UB_32      0.0189731000
_diffrn_orient_matrix_UB_33      0.0022883000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\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                4346
_reflns_number_total             5658
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.167
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5658
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.050
_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)+(0.0739P)²+3.7033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1466
_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:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C28, F1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F2, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C28, F3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C27, O6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24)
3.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Pd1 Pd 0.65874(3) 0.55221(3) 1.01743(4) 0.04204(16) Uani 1 d . . . .
Pd2 Pd 0.74690(3) 0.60349(3) 0.81621(4) 0.03914(16) Uani 1 d . . . .
F1 F 0.4507(11) 0.5846(10) 0.5592(11) 0.287(8) Uani 1 d . . . U
F2 F 0.4455(12) 0.4765(7) 0.6249(17) 0.328(11) Uani 1 d . . . U
F3 F 0.3854(9) 0.5671(13) 0.6989(17) 0.351(11) Uani 1 d . . . U
O1 O 1.0338(3) 0.5613(3) 0.9233(4) 0.0543(12) Uani 1 d . . . .
O2 O 0.7976(4) 0.3593(3) 1.1727(5) 0.0631(13) Uani 1 d . . . .
O3 O 0.6936(3) 0.7081(2) 0.8739(4) 0.0496(10) Uani 1 d . . . .
O4 O 0.6263(3) 0.6673(3) 1.0153(4) 0.0545(11) Uani 1 d . . . .
O5 O 0.6123(3) 0.5821(3) 0.7096(4) 0.0553(12) Uani 1 d . . . .
O6 O 0.5493(3) 0.5367(3) 0.8534(4) 0.0626(13) Uani 1 d . . . U
N1 N 0.9461(3) 0.5639(3) 0.8784(4) 0.0407(11) Uani 1 d . . . .
N2 N 0.8882(3) 0.6159(3) 0.9031(4) 0.0385(11) Uani 1 d . . . .
N3 N 0.7626(3) 0.4244(3) 1.1443(5) 0.0463(12) Uani 1 d . . . .
N4 N 0.7010(3) 0.4406(3) 1.0425(5) 0.0437(12) Uani 1 d . . . .
C1 C 0.7997(4) 0.5157(4) 0.7492(5) 0.0455(14) Uani 1 d . . . .
C2 C 0.7516(5) 0.4620(5) 0.6636(7) 0.0626(19) Uani 1 d . . . .
H2 H 0.6856 0.4663 0.6301 0.075 Uiso 1 calc . . R .
C3 C 0.8024(6) 0.4012(5) 0.6277(8) 0.074(2) Uani 1 d . . . .
H3 H 0.7698 0.3654 0.5706 0.089 Uiso 1 calc . . R .
C4 C 0.8987(7) 0.3941(5) 0.6755(7) 0.071(2) Uani 1 d . . . .
H4 H 0.9309 0.3528 0.6521 0.085 Uiso 1 calc . . R .
C5 C 0.9498(5) 0.4471(4) 0.7583(6) 0.0543(17) Uani 1 d . . . .
H5 H 1.0161 0.4435 0.7899 0.065 Uiso 1 calc . . R .
C6 C 0.8973(4) 0.5059(4) 0.7916(5) 0.0423(14) Uani 1 d . . . .
C7 C 0.9303(4) 0.6761(3) 0.9878(5) 0.0386(13) Uani 1 d . . . .
C8 C 0.8813(4) 0.6947(4) 1.0714(5) 0.0425(14) Uani 1 d . . . .
H8 H 0.8262 0.6674 1.0727 0.051 Uiso 1 calc . . R .
C9 C 0.9147(5) 0.7540(4) 1.1529(6) 0.0533(16) Uani 1 d . . . .
H9 H 0.8819 0.7667 1.2090 0.064 Uiso 1 calc . . R .
C10 C 0.9960(5) 0.7939(4) 1.1512(6) 0.0528(16) Uani 1 d . . . .
H10 H 1.0184 0.8339 1.2059 0.063 Uiso 1 calc . . R .
C11 C 1.0448(5) 0.7746(4) 1.0675(6) 0.0558(17) Uani 1 d . . . .
H11 H 1.1002 0.8016 1.0667 0.067 Uiso 1 calc . . R .
C12 C 1.0123(4) 0.7164(4) 0.9863(6) 0.0480(15) Uani 1 d . . . .
H12 H 1.0453 0.7039 0.9302 0.058 Uiso 1 calc . . R .
C13 C 0.7430(4) 0.5593(4) 1.1810(5) 0.0427(14) Uani 1 d . . . .
C14 C 0.7609(5) 0.6217(4) 1.2601(6) 0.0532(16) Uani 1 d . . . .
H14 H 0.7317 0.6693 1.2347 0.064 Uiso 1 calc . . R .
C15 C 0.8209(5) 0.6151(5) 1.3758(6) 0.0603(19) Uani 1 d . . . .
H15 H 0.8325 0.6581 1.4266 0.072 Uiso 1 calc . . R .
C16 C 0.8640(6) 0.5440(5) 1.4158(7) 0.069(2) Uani 1 d . . . .
H16 H 0.9049 0.5398 1.4931 0.083 Uiso 1 calc . . R .
C17 C 0.8463(5) 0.4795(5) 1.3413(7) 0.0610(18) Uani 1 d . . . .
H17 H 0.8734 0.4314 1.3676 0.073 Uiso 1 calc . . R .
C18 C 0.7864(4) 0.4893(4) 1.2256(6) 0.0438(14) Uani 1 d . . . .
C19 C 0.6721(4) 0.3780(4) 0.9578(6) 0.0471(15) Uani 1 d . . . .
C20 C 0.5777(5) 0.3553(5) 0.9305(7) 0.071(2) Uani 1 d . . . .
H20 H 0.5354 0.3782 0.9678 0.085 Uiso 1 calc . . R .
C21 C 0.5476(7) 0.2972(6) 0.8460(9) 0.095(3) Uani 1 d . . . .
H21 H 0.4839 0.2812 0.8260 0.114 Uiso 1 calc . . R .
C22 C 0.6103(7) 0.2622(6) 0.7905(9) 0.091(3) Uani 1 d . . . .
H22 H 0.5890 0.2224 0.7353 0.109 Uiso 1 calc . . R .
C23 C 0.7039(7) 0.2866(5) 0.8174(8) 0.078(2) Uani 1 d . . . .
H23 H 0.7461 0.2638 0.7796 0.094 Uiso 1 calc . . R .
C24 C 0.7357(5) 0.3459(5) 0.9018(7) 0.0632(19) Uani 1 d . . . .
H24 H 0.7988 0.3635 0.9199 0.076 Uiso 1 calc . . R .
C25 C 0.6487(4) 0.7189(4) 0.9494(6) 0.0456(14) Uani 1 d . . . .
C26 C 0.6158(6) 0.8016(4) 0.9672(8) 0.074(2) Uani 1 d . . . .
H26A H 0.6617 0.8255 1.0337 0.111 Uiso 1 calc . . GR .
H26B H 0.5543 0.7996 0.9834 0.111 Uiso 1 calc . . GR .
H26C H 0.6108 0.8314 0.8956 0.111 Uiso 1 calc . . GR .
C27 C 0.5455(5) 0.5547(4) 0.7484(6) 0.0489(14) Uani 1 d . . . U
C28 C 0.4516(7) 0.5424(8) 0.6541(11) 0.106(3) Uani 1 d . . . U


_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
Pd1 Pd2 3.0757(6) . ?
Pd1 O4 2.033(4) . ?
Pd1 O6 2.128(5) . ?
Pd1 N4 2.012(5) . ?
Pd1 C13 1.953(6) . ?
Pd2 O3 2.136(4) . ?
Pd2 O5 2.033(4) . ?
Pd2 N2 2.028(5) . ?
Pd2 C1 1.947(6) . ?
F1 C28 1.314(15) . ?
F2 C28 1.179(16) . ?
F3 C28 1.283(17) . ?
O1 N1 1.234(6) . ?
O2 N3 1.235(7) . ?
O3 C25 1.238(8) . ?
O4 C25 1.269(8) . ?
O5 C27 1.264(8) . ?
O6 C27 1.239(8) . ?
N1 N2 1.311(7) . ?
N1 C6 1.454(8) . ?
N2 C7 1.440(7) . ?
N3 N4 1.297(7) . ?
N3 C18 1.440(8) . ?
N4 C19 1.438(8) . ?
C1 C2 1.393(9) . ?
C1 C6 1.373(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.406(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(9) . ?
C7 C8 1.385(8) . ?
C7 C12 1.379(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(9) . ?
C13 C18 1.390(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.394(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(9) . ?
C19 C20 1.372(9) . ?
C19 C24 1.379(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(12) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(13) . ?
C22 H22 0.9300 . ?
C22 C23 1.370(12) . ?
C23 H23 0.9300 . ?
C23 C24 1.400(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.532(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.506(10) . ?

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
O4 Pd1 Pd2 81.63(12) . . ?
O4 Pd1 O6 89.9(2) . . ?
O6 Pd1 Pd2 73.97(13) . . ?
N4 Pd1 Pd2 102.10(15) . . ?
N4 Pd1 O4 172.3(2) . . ?
N4 Pd1 O6 97.5(2) . . ?
C13 Pd1 Pd2 115.89(17) . . ?
C13 Pd1 O4 91.8(2) . . ?
C13 Pd1 O6 170.1(2) . . ?
C13 Pd1 N4 80.5(2) . . ?
O3 Pd2 Pd1 75.19(12) . . ?
O5 Pd2 Pd1 83.00(13) . . ?
O5 Pd2 O3 88.45(19) . . ?
N2 Pd2 Pd1 103.17(13) . . ?
N2 Pd2 O3 99.13(18) . . ?
N2 Pd2 O5 171.21(19) . . ?
C1 Pd2 Pd1 111.67(18) . . ?
C1 Pd2 O3 173.1(2) . . ?
C1 Pd2 O5 92.0(2) . . ?
C1 Pd2 N2 80.0(2) . . ?
C25 O3 Pd2 130.6(4) . . ?
C25 O4 Pd1 126.3(4) . . ?
C27 O5 Pd2 123.5(4) . . ?
C27 O6 Pd1 131.6(4) . . ?
O1 N1 N2 125.4(5) . . ?
O1 N1 C6 121.0(5) . . ?
N2 N1 C6 113.6(5) . . ?
N1 N2 Pd2 116.0(4) . . ?
N1 N2 C7 117.6(5) . . ?
C7 N2 Pd2 126.4(4) . . ?
O2 N3 N4 124.5(6) . . ?
O2 N3 C18 121.4(5) . . ?
N4 N3 C18 114.1(5) . . ?
N3 N4 Pd1 116.2(4) . . ?
N3 N4 C19 117.1(5) . . ?
C19 N4 Pd1 126.6(4) . . ?
C2 C1 Pd2 128.6(5) . . ?
C6 C1 Pd2 115.6(4) . . ?
C6 C1 C2 115.8(6) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(7) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(7) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.3(7) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 121.8 . . ?
C4 C5 C6 116.4(7) . . ?
C6 C5 H5 121.8 . . ?
C1 C6 N1 114.8(5) . . ?
C1 C6 C5 125.6(6) . . ?
C5 C6 N1 119.6(6) . . ?
C8 C7 N2 115.9(5) . . ?
C12 C7 N2 123.9(5) . . ?
C12 C7 C8 120.1(6) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(6) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(6) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(6) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(6) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.6(6) . . ?
C11 C12 H12 120.2 . . ?
C14 C13 Pd1 129.8(5) . . ?
C14 C13 C18 116.3(6) . . ?
C18 C13 Pd1 113.8(5) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.8(7) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(7) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(7) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 121.3 . . ?
C16 C17 C18 117.5(7) . . ?
C18 C17 H17 121.3 . . ?
C13 C18 N3 115.3(5) . . ?
C13 C18 C17 124.1(6) . . ?
C17 C18 N3 120.6(6) . . ?
C20 C19 N4 117.0(6) . . ?
C20 C19 C24 122.0(7) . . ?
C24 C19 N4 120.8(6) . . ?
C19 C20 H20 121.0 . . ?
C19 C20 C21 118.0(8) . . ?
C21 C20 H20 121.0 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.5(8) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.7(8) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.7(8) . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 119.0(7) . . ?
C19 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
O3 C25 O4 126.1(6) . . ?
O3 C25 C26 118.5(6) . . ?
O4 C25 C26 115.4(6) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O5 C27 C28 115.0(7) . . ?
O6 C27 O5 127.5(6) . . ?
O6 C27 C28 117.5(8) . . ?
F1 C28 C27 109.1(10) . . ?
F2 C28 F1 108.0(16) . . ?
F2 C28 F3 115.4(16) . . ?
F2 C28 C27 108.9(12) . . ?
F3 C28 F1 108.5(16) . . ?
F3 C28 C27 106.8(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pd1 Pd2 O3 C25 -3.0(5) . . . . ?
Pd1 Pd2 O5 C27 -3.7(5) . . . . ?
Pd1 Pd2 N2 N1 109.5(4) . . . . ?
Pd1 Pd2 N2 C7 -70.9(4) . . . . ?
Pd1 Pd2 C1 C2 81.0(7) . . . . ?
Pd1 Pd2 C1 C6 -99.3(5) . . . . ?
Pd1 O4 C25 O3 0.7(9) . . . . ?
Pd1 O4 C25 C26 -179.4(5) . . . . ?
Pd1 O6 C27 O5 7.0(11) . . . . ?
Pd1 O6 C27 C28 -173.7(7) . . . . ?
Pd1 N4 C19 C20 -67.3(8) . . . . ?
Pd1 N4 C19 C24 109.0(7) . . . . ?
Pd1 C13 C14 C15 177.5(5) . . . . ?
Pd1 C13 C18 N3 0.3(7) . . . . ?
Pd1 C13 C18 C17 -177.5(5) . . . . ?
Pd2 Pd1 O4 C25 -2.1(5) . . . . ?
Pd2 Pd1 O6 C27 -6.9(6) . . . . ?
Pd2 Pd1 N4 N3 112.1(4) . . . . ?
Pd2 Pd1 N4 C19 -65.8(5) . . . . ?
Pd2 Pd1 C13 C14 86.3(6) . . . . ?
Pd2 Pd1 C13 C18 -97.9(4) . . . . ?
Pd2 O3 C25 O4 2.7(10) . . . . ?
Pd2 O3 C25 C26 -177.2(5) . . . . ?
Pd2 O5 C27 O6 0.1(10) . . . . ?
Pd2 O5 C27 C28 -179.3(7) . . . . ?
Pd2 N2 C7 C8 42.9(7) . . . . ?
Pd2 N2 C7 C12 -134.8(5) . . . . ?
Pd2 C1 C2 C3 -178.9(6) . . . . ?
Pd2 C1 C6 N1 -1.2(7) . . . . ?
Pd2 C1 C6 C5 179.0(5) . . . . ?
O1 N1 N2 Pd2 -179.0(4) . . . . ?
O1 N1 N2 C7 1.4(8) . . . . ?
O1 N1 C6 C1 179.9(5) . . . . ?
O1 N1 C6 C5 -0.3(9) . . . . ?
O2 N3 N4 Pd1 -178.2(5) . . . . ?
O2 N3 N4 C19 0.0(9) . . . . ?
O2 N3 C18 C13 179.0(5) . . . . ?
O2 N3 C18 C17 -3.1(9) . . . . ?
O3 Pd2 O5 C27 -79.0(5) . . . . ?
O3 Pd2 N2 N1 -173.7(4) . . . . ?
O3 Pd2 N2 C7 5.9(5) . . . . ?
O3 Pd2 C1 C2 -95.6(19) . . . . ?
O3 Pd2 C1 C6 84.1(19) . . . . ?
O4 Pd1 Pd2 O3 1.92(18) . . . . ?
O4 Pd1 Pd2 O5 -88.3(2) . . . . ?
O4 Pd1 Pd2 N2 98.05(19) . . . . ?
O4 Pd1 Pd2 C1 -177.7(2) . . . . ?
O4 Pd1 O6 C27 74.4(6) . . . . ?
O4 Pd1 N4 N3 -6.4(16) . . . . ?
O4 Pd1 N4 C19 175.7(12) . . . . ?
O4 Pd1 C13 C14 4.7(6) . . . . ?
O4 Pd1 C13 C18 -179.5(4) . . . . ?
O5 Pd2 O3 C25 80.1(6) . . . . ?
O5 Pd2 N2 N1 -24.4(15) . . . . ?
O5 Pd2 N2 C7 155.2(11) . . . . ?
O5 Pd2 C1 C2 -2.2(7) . . . . ?
O5 Pd2 C1 C6 177.4(5) . . . . ?
O5 C27 C28 F1 -19.3(16) . . . . ?
O5 C27 C28 F2 98.4(17) . . . . ?
O5 C27 C28 F3 -136.4(14) . . . . ?
O6 Pd1 Pd2 O3 94.2(2) . . . . ?
O6 Pd1 Pd2 O5 4.0(2) . . . . ?
O6 Pd1 Pd2 N2 -169.6(2) . . . . ?
O6 Pd1 Pd2 C1 -85.3(2) . . . . ?
O6 Pd1 O4 C25 -75.9(5) . . . . ?
O6 Pd1 N4 N3 -172.7(4) . . . . ?
O6 Pd1 N4 C19 9.4(5) . . . . ?
O6 Pd1 C13 C14 -95.3(15) . . . . ?
O6 Pd1 C13 C18 80.5(15) . . . . ?
O6 C27 C28 F1 161.2(12) . . . . ?
O6 C27 C28 F2 -81.1(18) . . . . ?
O6 C27 C28 F3 44.1(17) . . . . ?
N1 N2 C7 C8 -137.6(5) . . . . ?
N1 N2 C7 C12 44.8(8) . . . . ?
N2 Pd2 O3 C25 -104.3(5) . . . . ?
N2 Pd2 O5 C27 131.3(12) . . . . ?
N2 Pd2 C1 C2 -178.7(7) . . . . ?
N2 Pd2 C1 C6 1.0(5) . . . . ?
N2 N1 C6 C1 0.7(7) . . . . ?
N2 N1 C6 C5 -179.4(5) . . . . ?
N2 C7 C8 C9 -177.4(5) . . . . ?
N2 C7 C12 C11 177.5(6) . . . . ?
N3 N4 C19 C20 114.9(7) . . . . ?
N3 N4 C19 C24 -68.9(8) . . . . ?
N4 Pd1 Pd2 O3 -171.29(19) . . . . ?
N4 Pd1 Pd2 O5 98.5(2) . . . . ?
N4 Pd1 Pd2 N2 -75.2(2) . . . . ?
N4 Pd1 Pd2 C1 9.1(2) . . . . ?
N4 Pd1 O4 C25 117.6(14) . . . . ?
N4 Pd1 O6 C27 -107.4(6) . . . . ?
N4 Pd1 C13 C14 -174.8(6) . . . . ?
N4 Pd1 C13 C18 1.0(4) . . . . ?
N4 N3 C18 C13 -2.4(7) . . . . ?
N4 N3 C18 C17 175.5(6) . . . . ?
N4 C19 C20 C21 177.7(8) . . . . ?
N4 C19 C24 C23 -178.2(7) . . . . ?
C1 Pd2 O3 C25 173.7(17) . . . . ?
C1 Pd2 O5 C27 107.9(5) . . . . ?
C1 Pd2 N2 N1 -0.6(4) . . . . ?
C1 Pd2 N2 C7 179.0(5) . . . . ?
C1 C2 C3 C4 -0.1(13) . . . . ?
C2 C1 C6 N1 178.5(6) . . . . ?
C2 C1 C6 C5 -1.3(10) . . . . ?
C2 C3 C4 C5 -1.6(14) . . . . ?
C3 C4 C5 C6 1.7(12) . . . . ?
C4 C5 C6 N1 180.0(6) . . . . ?
C4 C5 C6 C1 -0.2(10) . . . . ?
C6 N1 N2 Pd2 0.1(6) . . . . ?
C6 N1 N2 C7 -179.6(5) . . . . ?
C6 C1 C2 C3 1.5(11) . . . . ?
C7 C8 C9 C10 -0.2(10) . . . . ?
C8 C7 C12 C11 -0.1(10) . . . . ?
C8 C9 C10 C11 -0.1(11) . . . . ?
C9 C10 C11 C12 0.4(11) . . . . ?
C10 C11 C12 C7 -0.3(11) . . . . ?
C12 C7 C8 C9 0.3(9) . . . . ?
C13 Pd1 Pd2 O3 -86.0(2) . . . . ?
C13 Pd1 Pd2 O5 -176.3(3) . . . . ?
C13 Pd1 Pd2 N2 10.1(2) . . . . ?
C13 Pd1 Pd2 C1 94.4(3) . . . . ?
C13 Pd1 O4 C25 113.8(5) . . . . ?
C13 Pd1 O6 C27 174.5(12) . . . . ?
C13 Pd1 N4 N3 -2.5(4) . . . . ?
C13 Pd1 N4 C19 179.6(5) . . . . ?
C13 C14 C15 C16 -1.0(11) . . . . ?
C14 C13 C18 N3 176.7(5) . . . . ?
C14 C13 C18 C17 -1.1(9) . . . . ?
C14 C15 C16 C17 -0.8(12) . . . . ?
C15 C16 C17 C18 1.5(12) . . . . ?
C16 C17 C18 N3 -178.3(6) . . . . ?
C16 C17 C18 C13 -0.6(11) . . . . ?
C18 N3 N4 Pd1 3.3(6) . . . . ?
C18 N3 N4 C19 -178.6(5) . . . . ?
C18 C13 C14 C15 1.8(9) . . . . ?
C19 C20 C21 C22 0.4(15) . . . . ?
C20 C19 C24 C23 -2.1(12) . . . . ?
C20 C21 C22 C23 -1.5(16) . . . . ?
C21 C22 C23 C24 0.8(15) . . . . ?
C22 C23 C24 C19 0.9(13) . . . . ?
C24 C19 C20 C21 1.4(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_201410198
_database_code_depnum_ccdc_archive 'CCDC 1030211'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;
_audit_creation_date             2014-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H18 N2 O3'
_chemical_formula_sum            'C17 H18 N2 O3'
_chemical_formula_weight         298.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.8879(9)
_cell_length_b                   8.2820(9)
_cell_length_c                   14.4023(10)
_cell_angle_alpha                104.655(8)
_cell_angle_beta                 94.121(9)
_cell_angle_gamma                91.668(10)
_cell_volume                     791.85(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1393
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.9010
_cell_measurement_theta_min      3.4030
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6560
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -77.0000  -87.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   77.0000   37.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -99.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -99.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega  -51.00   45.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -37.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   62.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -53.00   13.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -37.0000    0.0000 66
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0414562000
_diffrn_orient_matrix_UB_12      -0.0223360000
_diffrn_orient_matrix_UB_13      0.0389338000
_diffrn_orient_matrix_UB_21      -0.0942368000
_diffrn_orient_matrix_UB_22      0.0132509000
_diffrn_orient_matrix_UB_23      -0.0191225000
_diffrn_orient_matrix_UB_31      -0.0090604000
_diffrn_orient_matrix_UB_32      -0.0846744000
_diffrn_orient_matrix_UB_33      -0.0269162000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\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                2128
_reflns_number_total             3249
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.026
_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)+(0.0580P)²+0.0864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1377
_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:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -0.2149(3) 0.30110(18) 0.64377(12) 0.0890(6) Uani 1 d . . .
O2 O 0.30011(19) 0.26101(15) 0.78158(9) 0.0532(4) Uani 1 d . . .
O3 O 0.2495(2) 0.11774(17) 0.89195(10) 0.0725(5) Uani 1 d . . .
N1 N -0.1004(2) 0.25359(19) 0.70293(11) 0.0547(4) Uani 1 d . . .
N2 N -0.0561(2) 0.10517(19) 0.70119(11) 0.0521(4) Uani 1 d . . .
C1 C -0.0141(3) 0.3841(2) 0.78494(13) 0.0504(5) Uani 1 d . . .
C2 C -0.1288(3) 0.5159(2) 0.82280(15) 0.0636(6) Uani 1 d . . .
H2 H -0.2557 0.5177 0.7963 0.076 Uiso 1 calc . . R
C3 C -0.0557(4) 0.6440(3) 0.89944(15) 0.0662(6) Uani 1 d . . .
H3 H -0.1347 0.7308 0.9249 0.079 Uiso 1 calc . . R
C4 C 0.1335(4) 0.6457(2) 0.93926(14) 0.0599(5) Uani 1 d . . .
C5 C 0.2480(3) 0.5139(2) 0.89945(13) 0.0564(5) Uani 1 d . . .
H5 H 0.3763 0.5139 0.9244 0.068 Uiso 1 calc . . R
C6 C 0.1752(3) 0.3834(2) 0.82389(13) 0.0493(5) Uani 1 d . . .
C7 C 0.2157(4) 0.7880(3) 1.02138(16) 0.0783(7) Uani 1 d . . .
H7A H 0.3256 0.7520 1.0544 0.118 Uiso 1 calc . . GR
H7B H 0.1176 0.8229 1.0654 0.118 Uiso 1 calc . . GR
H7C H 0.2562 0.8799 0.9967 0.118 Uiso 1 calc . . GR
C8 C -0.1320(3) -0.0298(2) 0.62476(13) 0.0471(4) Uani 1 d . . .
C9 C -0.2333(3) -0.0265(3) 0.53774(14) 0.0585(5) Uani 1 d . . .
H9 H -0.2615 0.0750 0.5246 0.070 Uiso 1 calc . . R
C10 C -0.2908(3) -0.1739(3) 0.47193(14) 0.0615(6) Uani 1 d . . .
H10 H -0.3564 -0.1700 0.4139 0.074 Uiso 1 calc . . R
C11 C -0.2554(3) -0.3278(2) 0.48815(14) 0.0554(5) Uani 1 d . . .
C12 C -0.1565(3) -0.3296(2) 0.57509(15) 0.0641(6) Uani 1 d . . .
H12 H -0.1315 -0.4314 0.5886 0.077 Uiso 1 calc . . R
C13 C -0.0948(3) -0.1838(2) 0.64165(14) 0.0576(5) Uani 1 d . . .
H13 H -0.0269 -0.1885 0.6990 0.069 Uiso 1 calc . . R
C14 C -0.3225(3) -0.4866(3) 0.41403(16) 0.0758(7) Uani 1 d . . .
H14A H -0.4530 -0.4764 0.3887 0.114 Uiso 1 calc . . GR
H14B H -0.3198 -0.5785 0.4434 0.114 Uiso 1 calc . . GR
H14C H -0.2375 -0.5061 0.3628 0.114 Uiso 1 calc . . GR
C15 C 0.3170(3) 0.1251(2) 0.81942(14) 0.0514(5) Uani 1 d . . .
C16 C 0.4319(3) -0.0034(2) 0.75698(15) 0.0641(6) Uani 1 d . . .
H16A H 0.5541 0.0491 0.7475 0.077 Uiso 1 calc . . R
H16B H 0.3602 -0.0434 0.6944 0.077 Uiso 1 calc . . R
C17 C 0.4750(4) -0.1499(3) 0.79712(18) 0.0811(7) Uani 1 d . . .
H17A H 0.5468 -0.2279 0.7530 0.122 Uiso 1 calc . . GR
H17B H 0.3549 -0.2034 0.8062 0.122 Uiso 1 calc . . GR
H17C H 0.5509 -0.1121 0.8578 0.122 Uiso 1 calc . . GR


_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 N1 1.262(2) . ?
O2 C6 1.398(2) . ?
O2 C15 1.373(2) . ?
O3 C15 1.188(2) . ?
N1 N2 1.270(2) . ?
N1 C1 1.460(2) . ?
N2 C8 1.412(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.383(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C4 C5 1.393(3) . ?
C4 C7 1.506(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.397(3) . ?
C8 C13 1.385(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C11 C12 1.385(3) . ?
C11 C14 1.505(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.495(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.499(3) . ?
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
C15 O2 C6 117.22(14) . . ?
O1 N1 N2 127.68(17) . . ?
O1 N1 C1 116.18(15) . . ?
N2 N1 C1 116.10(16) . . ?
N1 N2 C8 120.40(16) . . ?
C2 C1 N1 117.29(19) . . ?
C6 C1 N1 123.17(17) . . ?
C6 C1 C2 119.53(18) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.0(2) . . ?
C3 C4 C7 121.1(2) . . ?
C5 C4 C7 120.8(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 O2 120.81(17) . . ?
C5 C6 O2 119.19(19) . . ?
C5 C6 C1 119.69(18) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N2 129.00(17) . . ?
C13 C8 N2 112.74(16) . . ?
C13 C8 C9 118.26(17) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.46(18) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.6 . . ?
C9 C10 C11 122.79(19) . . ?
C11 C10 H10 118.6 . . ?
C10 C11 C12 117.22(18) . . ?
C10 C11 C14 120.94(19) . . ?
C12 C11 C14 121.8(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.20(19) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 121.06(18) . . ?
C12 C13 H13 119.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 C16 109.81(16) . . ?
O3 C15 O2 122.85(17) . . ?
O3 C15 C16 127.33(18) . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C15 C16 C17 113.95(18) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 N2 C8 2.5(3) . . . . ?
O1 N1 C1 C2 35.3(3) . . . . ?
O1 N1 C1 C6 -143.0(2) . . . . ?
O2 C15 C16 C17 174.43(18) . . . . ?
O3 C15 C16 C17 -4.7(3) . . . . ?
N1 N2 C8 C9 10.5(3) . . . . ?
N1 N2 C8 C13 -170.32(16) . . . . ?
N1 C1 C2 C3 -179.29(17) . . . . ?
N1 C1 C6 O2 4.5(3) . . . . ?
N1 C1 C6 C5 178.00(16) . . . . ?
N2 N1 C1 C2 -142.56(18) . . . . ?
N2 N1 C1 C6 39.1(2) . . . . ?
N2 C8 C9 C10 178.56(18) . . . . ?
N2 C8 C13 C12 -179.64(18) . . . . ?
C1 N1 N2 C8 -179.90(15) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C1 C6 O2 -173.82(16) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C7 178.32(19) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 O2 175.00(16) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C6 O2 C15 O3 -9.1(3) . . . . ?
C6 O2 C15 C16 171.72(17) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C7 C4 C5 C6 -179.54(17) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C9 C10 C11 C14 179.6(2) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 1.0(3) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
C14 C11 C12 C13 179.4(2) . . . . ?
C15 O2 C6 C1 -96.6(2) . . . . ?
C15 O2 C6 C5 89.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
