# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_exp_10603
_database_code_depnum_ccdc_archive 'CCDC 1056239'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2015-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.09 svn.r3130 for OlexSys, GUI svn.r4987)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H6 N4'
_chemical_formula_sum            'C14 H6 N4'
_chemical_formula_weight         230.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N H'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9562(4)
_cell_length_b                   8.6030(4)
_cell_length_c                   10.0638(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.584(7)
_cell_angle_gamma                90
_cell_volume                     582.86(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1722
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.6570
_cell_measurement_theta_min      7.0050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76216
_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    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             236
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4575
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.142
_diffrn_reflns_theta_min         6.867
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega   46.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   28.00  103.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397    0.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega   -3.00   75.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
  6 omega   -6.00   23.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397    0.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega   11.00   86.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -99.0000  150.0000 75

#__ type_ start__ end____ width___ exp.time_
  8 omega   60.00   87.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   83.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00  133.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -63.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   99.00  137.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794  138.0000   39.0000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega  142.00  178.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794  138.0000   39.0000 36

#__ type_ start__ end____ width___ exp.time_
 13 omega   86.00  115.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   91.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000    0.0000 51

#__ type_ start__ end____ width___ exp.time_
 15 omega   78.00  104.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  126.00  153.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794  111.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega  107.00  132.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega  134.00  171.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
 19 omega   45.00   80.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 20 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
 21 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
 22 omega   25.00  126.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 23 omega  -15.00   86.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 24 omega   25.00  126.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 25 omega   25.00  126.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
 26 omega   34.00  124.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
 27 omega   25.00  126.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 28 omega   41.00  123.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -77.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
 29 omega   39.00  178.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794   12.0000 -150.0000 139

#__ type_ start__ end____ width___ exp.time_
 30 omega   77.00  178.00   1.0000    3.3400
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000  -30.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0085367000
_diffrn_orient_matrix_UB_12      0.1769221000
_diffrn_orient_matrix_UB_13      -0.0241623000
_diffrn_orient_matrix_UB_21      0.0142523000
_diffrn_orient_matrix_UB_22      0.0269014000
_diffrn_orient_matrix_UB_23      0.1534895000
_diffrn_orient_matrix_UB_31      0.2283416000
_diffrn_orient_matrix_UB_32      0.0050180000
_diffrn_orient_matrix_UB_33      0.0294664000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                951
_reflns_number_total             1140
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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         0.186
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039
_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     82
_refine_ls_number_reflns         1140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0782P)²+0.0550P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1345
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7313(3) -0.01571(18) 0.4406(2) 0.0938(6) Uani 1 1 d . . . . .
N2 N 0.1805(2) 0.1953(2) 0.21488(18) 0.0798(5) Uani 1 1 d . . . . .
C1 C 0.9843(2) 0.34103(17) 0.47567(17) 0.0551(4) Uani 1 1 d . . . . .
H1 H 0.9747 0.2346 0.4589 0.066 Uiso 1 1 calc R . . . .
C2 C 0.8168(2) 0.43511(16) 0.43189(15) 0.0484(4) Uani 1 1 d . . . . .
C3 C 0.8369(2) 0.59538(16) 0.45679(16) 0.0530(4) Uani 1 1 d . . . . .
H3 H 0.7271 0.6598 0.4270 0.064 Uiso 1 1 calc R . . . .
C4 C 0.6197(2) 0.38007(17) 0.36241(16) 0.0522(4) Uani 1 1 d . . . . .
H4 H 0.5311 0.4575 0.3216 0.063 Uiso 1 1 calc R . . . .
C5 C 0.5448(2) 0.23536(17) 0.34759(16) 0.0521(4) Uani 1 1 d . . . . .
C6 C 0.6512(3) 0.09654(17) 0.40068(18) 0.0620(5) Uani 1 1 d . . . . .
C7 C 0.3419(3) 0.21154(18) 0.27388(17) 0.0601(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.137(2) . ?
N2 C7 1.139(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.396(2) . ?
C1 C3 1.372(2) 3_766 ?
C2 C3 1.4021(19) . ?
C2 C4 1.452(2) . ?
C3 C1 1.372(2) 3_766 ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.343(2) . ?
C5 C6 1.435(2) . ?
C5 C7 1.434(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
C2 C1 H1 119.8 . . ?
C3 C1 H1 119.8 3_766 . ?
C3 C1 C2 120.38(13) 3_766 . ?
C1 C2 C3 118.42(13) . . ?
C1 C2 C4 125.07(14) . . ?
C3 C2 C4 116.51(13) . . ?
C1 C3 C2 121.19(13) 3_766 . ?
C1 C3 H3 119.4 3_766 . ?
C2 C3 H3 119.4 . . ?
C2 C4 H4 114.8 . . ?
C5 C4 C2 130.41(14) . . ?
C5 C4 H4 114.8 . . ?
C4 C5 C6 125.50(15) . . ?
C4 C5 C7 119.57(14) . . ?
C7 C5 C6 114.92(14) . . ?
N1 C6 C5 178.2(2) . . ?
N2 C7 C5 178.81(18) . . ?

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
C1 C2 C3 C1 -1.0(3) . . . 3_766 ?
C1 C2 C4 C5 13.8(3) . . . . ?
C2 C4 C5 C6 -0.1(3) . . . . ?
C2 C4 C5 C7 179.60(15) . . . . ?
C3 C1 C2 C3 1.0(3) 3_766 . . . ?
C3 C1 C2 C4 -178.58(14) 3_766 . . . ?
C3 C2 C4 C5 -165.74(16) . . . . ?
C4 C2 C3 C1 178.61(14) . . . 3_766 ?

_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_exp_10854
_database_code_depnum_ccdc_archive 'CCDC 1056280'
_audit_update_record             
;
2015-03-26 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2015-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H14 N4 O4'
_chemical_formula_sum            'C18 H12 N4 O4'
_chemical_formula_weight         348.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C O N H'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1736(3)
_cell_length_b                   4.9312(2)
_cell_length_c                   17.7827(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.441(4)
_cell_angle_gamma                90
_cell_volume                     886.49(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2292
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9580
_cell_measurement_theta_min      4.8090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75961
_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    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             360
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.253
_diffrn_reflns_theta_min         4.373
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   27.00   67.00   1.0000    2.6800
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega  -30.00   -3.00   1.0000    2.6800
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00   25.00   1.0000    2.6800
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   28.00   1.0000    2.6800
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   43.00  113.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -       55.5397 -125.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  6 omega  -15.00   73.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -37.0000  120.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega   -1.00   98.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -19.0000    0.0000 99

#__ type_ start__ end____ width___ exp.time_
  8 omega   45.00  104.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -50.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega   56.00   90.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   64.00   92.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   94.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega  130.00  156.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00  115.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000  150.0000 75

#__ type_ start__ end____ width___ exp.time_
 14 omega   86.00  126.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 15 omega   66.00   95.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 16 omega   46.00   93.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
 17 omega   45.00   84.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 18 omega   65.00   92.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega  -70.00   30.00   1.0000    2.6800
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
 20 omega  -69.00   21.00   1.0000    2.6800
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
 21 omega   34.00  124.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 22 omega  -15.00   86.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -77.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 23 omega   25.00  126.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 24 omega   34.00  124.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000 -120.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega   77.00  178.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
 26 omega   89.00  178.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794   50.0000  -90.0000 89

#__ type_ start__ end____ width___ exp.time_
 27 omega   77.00  178.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 28 omega   41.00  141.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -77.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
 29 omega   41.00  105.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -50.0000   90.0000 64

#__ type_ start__ end____ width___ exp.time_
 30 omega   77.00  178.00   1.0000   10.7100
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000  120.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0623980000
_diffrn_orient_matrix_UB_12      0.0260628000
_diffrn_orient_matrix_UB_13      0.0826991000
_diffrn_orient_matrix_UB_21      0.1360481000
_diffrn_orient_matrix_UB_22      0.0527369000
_diffrn_orient_matrix_UB_23      -0.0275000000
_diffrn_orient_matrix_UB_31      -0.0286365000
_diffrn_orient_matrix_UB_32      0.3068142000
_diffrn_orient_matrix_UB_33      -0.0022230000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1423
_reflns_number_total             1709
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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         0.144
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0614P)²+0.1548P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1161
_refine_special_details          
;
 ?
;
_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), C4(H4)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20821(9) 0.7713(2) 0.43593(7) 0.0606(4) Uani 1 1 d . . . . .
O2 O 0.36358(11) 1.1169(3) 0.43132(7) 0.0665(4) Uani 1 1 d . . . . .
N1 N -0.37980(16) 0.6226(6) 0.35991(13) 0.1157(9) Uani 1 1 d . . . . .
N2 N -0.12566(16) 0.0672(3) 0.26079(9) 0.0705(4) Uani 1 1 d . . . . .
C1 C 0.12592(13) 1.1034(3) 0.51954(8) 0.0454(3) Uani 1 1 d . . . . .
H1 H 0.2102 1.1743 0.5321 0.055 Uiso 1 1 calc R . . . .
C2 C 0.10831(13) 0.8932(3) 0.46841(8) 0.0439(3) Uani 1 1 d . . . . .
C3 C -0.01925(12) 0.7872(3) 0.44699(7) 0.0412(3) Uani 1 1 d . . . . .
C4 C -0.03231(13) 0.5694(3) 0.39200(7) 0.0441(3) Uani 1 1 d . . . . .
H4 H 0.0469 0.4913 0.3816 0.053 Uiso 1 1 calc R . . . .
C5 C -0.14140(14) 0.4633(3) 0.35380(8) 0.0466(4) Uani 1 1 d . . . . .
C6 C -0.13148(15) 0.2438(3) 0.30181(8) 0.0519(4) Uani 1 1 d . . . . .
C7 C -0.27396(16) 0.5553(4) 0.35791(11) 0.0686(5) Uani 1 1 d . . . . .
C8 C 0.34156(14) 0.8608(4) 0.45699(11) 0.0604(5) Uani 1 1 d . . . . .
H8A H 0.3929(16) 0.719(3) 0.4330(9) 0.054(4) Uiso 1 1 d . . . . .
H8B H 0.3597(17) 0.865(4) 0.5121(10) 0.060(5) Uiso 1 1 d . . . . .
C9 C 0.3550(2) 1.1363(5) 0.35082(12) 0.0878(6) Uani 1 1 d . . . . .
H9A H 0.2651 1.1079 0.3295 0.132 Uiso 1 1 calc GR . . . .
H9B H 0.4106 1.0010 0.3319 0.132 Uiso 1 1 calc GR . . . .
H9C H 0.3836 1.3131 0.3369 0.132 Uiso 1 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 C2 1.3635(16) . ?
O1 C8 1.4357(18) . ?
O2 C8 1.370(2) . ?
O2 C9 1.428(2) . ?
N1 C7 1.131(2) . ?
N2 C6 1.142(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(2) . ?
C1 C3 1.4027(18) 3_576 ?
C2 C3 1.4111(18) . ?
C3 C1 1.4027(18) 3_576 ?
C3 C4 1.4488(19) . ?
C4 H4 0.9300 . ?
C4 C5 1.3408(19) . ?
C5 C6 1.434(2) . ?
C5 C7 1.432(2) . ?
C8 H8A 0.998(17) . ?
C8 H8B 0.976(18) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C2 O1 C8 118.78(12) . . ?
C8 O2 C9 113.70(16) . . ?
C2 C1 H1 119.3 . . ?
C2 C1 C3 121.33(13) . 3_576 ?
C3 C1 H1 119.3 3_576 . ?
O1 C2 C1 124.29(12) . . ?
O1 C2 C3 115.41(12) . . ?
C1 C2 C3 120.29(12) . . ?
C1 C3 C2 118.36(13) 3_576 . ?
C1 C3 C4 123.69(12) 3_576 . ?
C2 C3 C4 117.95(12) . . ?
C3 C4 H4 115.1 . . ?
C5 C4 C3 129.73(13) . . ?
C5 C4 H4 115.1 . . ?
C4 C5 C6 120.45(13) . . ?
C4 C5 C7 125.53(14) . . ?
C7 C5 C6 113.99(13) . . ?
N2 C6 C5 178.76(17) . . ?
N1 C7 C5 178.2(2) . . ?
O1 C8 H8A 101.4(10) . . ?
O1 C8 H8B 109.6(10) . . ?
O2 C8 O1 112.42(14) . . ?
O2 C8 H8A 113.1(9) . . ?
O2 C8 H8B 107.2(11) . . ?
H8A C8 H8B 113.2(14) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C2 C3 C1 177.67(12) . . . 3_576 ?
O1 C2 C3 C4 -1.80(19) . . . . ?
C1 C2 C3 C1 -1.6(2) . . . 3_576 ?
C1 C2 C3 C4 178.93(13) . . . . ?
C1 C3 C4 C5 12.1(2) 3_576 . . . ?
C2 O1 C8 O2 -68.93(19) . . . . ?
C2 C3 C4 C5 -168.43(14) . . . . ?
C3 C1 C2 O1 -177.55(13) 3_576 . . . ?
C3 C1 C2 C3 1.6(2) 3_576 . . . ?
C3 C4 C5 C6 -179.48(14) . . . . ?
C3 C4 C5 C7 2.4(3) . . . . ?
C8 O1 C2 C1 1.5(2) . . . . ?
C8 O1 C2 C3 -177.69(13) . . . . ?
C9 O2 C8 O1 -66.04(19) . . . . ?

_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_exp_11409
_database_code_depnum_ccdc_archive 'CCDC 1403124'
_audit_update_record             
;
2015-05-26 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2015-05-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H10 N4 O2'
_chemical_formula_sum            'C16 H10 N4 O2'
_chemical_formula_weight         290.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.9933(4)
_cell_length_b                   16.4932(9)
_cell_length_c                   10.7618(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.630(6)
_cell_angle_gamma                90
_cell_volume                     707.37(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2330
_cell_measurement_theta_min      5.3750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72989
_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    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             300
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6759
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.196
_diffrn_reflns_theta_min         4.914
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    6.00   42.00   1.0000    2.1000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   18.00   68.00   1.0000    2.1000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega   71.00  101.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397 -125.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega    6.00   72.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000   90.0000 66

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   65.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
  6 omega  -11.00   88.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397    0.0000  -60.0000 99

#__ type_ start__ end____ width___ exp.time_
  7 omega   56.00   83.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   62.00   94.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   89.00  177.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   50.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
 10 omega  110.00  149.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  179.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
 11 omega   56.00  105.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  179.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00   70.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00   88.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
 14 omega   47.00  140.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -77.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
 15 omega  -21.00   69.00   1.0000    2.1000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 16 omega   34.00  124.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 17 omega   25.00  126.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 18 omega   11.00  129.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   19.0000   90.0000 118

#__ type_ start__ end____ width___ exp.time_
 19 omega   77.00  178.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
 20 omega   89.00  178.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   63.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
 21 omega   81.00  178.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000    0.0000 97

#__ type_ start__ end____ width___ exp.time_
 22 omega   77.00  178.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 23 omega  100.00  178.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  111.0000   30.0000 78

#__ type_ start__ end____ width___ exp.time_
 24 omega  -21.00   69.00   1.0000    2.1000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
 25 omega  -13.00   76.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 26 omega   25.00  126.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
 27 omega   25.00  126.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
 28 omega   89.00  178.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   50.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
 29 omega   89.00  178.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   63.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
 30 omega   81.00  178.00   1.0000    8.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000 -120.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1045937000
_diffrn_orient_matrix_UB_12      0.0197473000
_diffrn_orient_matrix_UB_13      0.1368994000
_diffrn_orient_matrix_UB_21      -0.0099718000
_diffrn_orient_matrix_UB_22      0.0912403000
_diffrn_orient_matrix_UB_23      -0.0306677000
_diffrn_orient_matrix_UB_31      -0.3720139000
_diffrn_orient_matrix_UB_32      0.0031489000
_diffrn_orient_matrix_UB_33      0.0298754000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1120
_reflns_number_total             1371
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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         0.152
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0772P)²+0.0700P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1314
_refine_special_details          
;
 ?
;
_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:
 C4(H4), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1895(3) 0.06651(6) 0.28855(9) 0.0674(4) Uani 1 1 d . . . . .
N1 N 0.4003(5) 0.37998(9) 0.45713(16) 0.0860(5) Uani 1 1 d . . . . .
N2 N 0.9095(5) 0.23492(9) 0.73539(15) 0.0794(5) Uani 1 1 d . . . . .
C1 C 0.4644(4) 0.31559(9) 0.48760(15) 0.0623(5) Uani 1 1 d . . . . .
C2 C 0.5476(4) 0.23474(8) 0.52972(14) 0.0526(4) Uani 1 1 d . . . . .
C3 C 0.7476(5) 0.23274(8) 0.64505(15) 0.0574(4) Uani 1 1 d . . . . .
C4 C 0.4359(4) 0.17075(8) 0.46109(13) 0.0527(4) Uani 1 1 d . . . . .
H4 H 0.3141 0.1840 0.3874 0.063 Uiso 1 1 calc R . . . .
C5 C 0.4754(4) 0.08442(8) 0.48386(12) 0.0493(4) Uani 1 1 d . . . . .
C6 C 0.3383(4) 0.03132(9) 0.39093(12) 0.0511(4) Uani 1 1 d . . . . .
C7 C 0.3658(4) -0.05158(9) 0.40831(12) 0.0527(4) Uani 1 1 d . . . . .
H7 H 0.2762 -0.0863 0.3467 0.063 Uiso 1 1 calc R . . . .
C8 C 0.0327(5) 0.01562(10) 0.19430(15) 0.0644(5) Uani 1 1 d . . . . .
H8A H -0.0857 0.0486 0.1325 0.097 Uiso 1 1 calc GR . . . .
H8B H -0.1222 -0.0203 0.2312 0.097 Uiso 1 1 calc GR . . . .
H8C H 0.2008 -0.0156 0.1560 0.097 Uiso 1 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 C6 1.3496(16) . ?
O1 C8 1.4299(17) . ?
N1 C1 1.136(2) . ?
N2 C3 1.134(2) . ?
C1 C2 1.440(2) . ?
C2 C3 1.433(2) . ?
C2 C4 1.348(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.4517(18) . ?
C5 C6 1.4133(19) . ?
C5 C7 1.3961(19) 3_656 ?
C6 C7 1.384(2) . ?
C7 C5 1.3962(19) 3_656 ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C6 O1 C8 118.49(12) . . ?
N1 C1 C2 178.40(18) . . ?
C3 C2 C1 113.50(12) . . ?
C4 C2 C1 119.38(13) . . ?
C4 C2 C3 127.12(13) . . ?
N2 C3 C2 176.73(16) . . ?
C2 C4 H4 114.8 . . ?
C2 C4 C5 130.31(13) . . ?
C5 C4 H4 114.8 . . ?
C6 C5 C4 117.08(12) . . ?
C7 C5 C4 124.02(13) 3_656 . ?
C7 C5 C6 118.89(13) 3_656 . ?
O1 C6 C5 116.23(12) . . ?
O1 C6 C7 124.22(12) . . ?
C7 C6 C5 119.54(13) . . ?
C5 C7 H7 119.2 3_656 . ?
C6 C7 C5 121.58(13) . 3_656 ?
C6 C7 H7 119.2 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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 C6 C7 C5 179.62(14) . . . 3_656 ?
C1 C2 C4 C5 -178.09(16) . . . . ?
C2 C4 C5 C6 -177.62(16) . . . . ?
C2 C4 C5 C7 3.4(3) . . . 3_656 ?
C3 C2 C4 C5 1.7(3) . . . . ?
C4 C5 C6 O1 1.3(2) . . . . ?
C4 C5 C6 C7 -179.37(14) . . . . ?
C5 C6 C7 C5 0.3(3) . . . 3_656 ?
C7 C5 C6 O1 -179.66(14) 3_656 . . . ?
C7 C5 C6 C7 -0.3(3) 3_656 . . . ?
C8 O1 C6 C5 -177.07(15) . . . . ?
C8 O1 C6 C7 3.6(2) . . . . ?

_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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1439332'
_audit_update_record             
;
2015-11-27 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H10 N4 O2'
_chemical_formula_weight         362.34

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.8800(4)
_cell_length_b                   7.8430(3)
_cell_length_c                   21.0513(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.528(4)
_cell_angle_gamma                90
_cell_volume                     1795.71(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1985
_cell_measurement_theta_min      4.1730
_cell_measurement_theta_max      69.5230

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.732
_shelx_estimated_absorpt_T_min   0.821
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_T_min  0.78434
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            3587
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.202
_diffrn_reflns_theta_max         69.779
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1651
_reflns_number_gt                1480
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+0.5090P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1651
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.12975(11) 0.20714(17) 0.14435(6) 0.0689(4) Uani 1 1 d . . . . .
C9 C 0.83469(12) 0.37820(18) -0.16835(6) 0.0449(3) Uani 1 1 d . . . . .
C5 C 0.86252(12) 0.23504(17) 0.03512(6) 0.0422(3) Uani 1 1 d . . . . .
C7 C 0.74870(12) 0.31864(18) -0.06159(6) 0.0425(3) Uani 1 1 d . . . . .
C3 C 0.98250(12) 0.21909(18) 0.06860(7) 0.0447(3) Uani 1 1 d . . . . .
N2 N 0.81971(14) 0.5378(2) -0.27526(7) 0.0731(5) Uani 1 1 d . . . . .
C8 C 0.74894(12) 0.39766(18) -0.12443(6) 0.0446(3) Uani 1 1 d . . . . .
H8 H 0.6830 0.4685 -0.1350 0.054 Uiso 1 1 calc R U . . .
C6 C 0.85784(12) 0.30346(18) -0.02588(6) 0.0449(3) Uani 1 1 d . . . . .
H6 H 0.9306 0.3406 -0.0436 0.054 Uiso 1 1 calc R U . . .
C11 C 0.82529(13) 0.4674(2) -0.22791(7) 0.0513(4) Uani 1 1 d . . . . .
C2 C 1.09534(13) 0.1744(2) 0.04059(8) 0.0575(4) Uani 1 1 d . . . . .
H2 H 1.1077 0.1541 -0.0023 0.069 Uiso 1 1 calc R U . . .
N1 N 1.02408(14) 0.1839(2) -0.15647(9) 0.0822(5) Uani 1 1 d . . . . .
C10 C 0.93933(14) 0.2680(2) -0.16111(8) 0.0546(4) Uani 1 1 d . . . . .
C4 C 1.00961(15) 0.2378(2) 0.13139(8) 0.0561(4) Uani 1 1 d . . . . .
H4 H 0.9528 0.2678 0.1617 0.067 Uiso 1 1 calc R U . . .
C1 C 1.18028(14) 0.1672(2) 0.08730(9) 0.0667(5) Uani 1 1 d . . . . .
H1 H 1.2624 0.1389 0.0819 0.080 Uiso 1 1 calc R 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
O1 C4 1.3497(19) . ?
O1 C1 1.370(2) . ?
C9 C8 1.3396(19) . ?
C9 C10 1.434(2) . ?
C9 C11 1.4369(19) . ?
C5 C6 1.3914(19) . ?
C5 C7 1.4100(19) 7_655 ?
C5 C3 1.4722(19) . ?
C7 C6 1.3934(19) . ?
C7 C5 1.4100(19) 7_655 ?
C7 C8 1.4609(19) . ?
C3 C4 1.355(2) . ?
C3 C2 1.420(2) . ?
N2 C11 1.140(2) . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C2 C1 1.333(2) . ?
C2 H2 0.9300 . ?
N1 C10 1.136(2) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C1 105.81(13) . . ?
C8 C9 C10 124.11(13) . . ?
C8 C9 C11 120.80(12) . . ?
C10 C9 C11 115.08(12) . . ?
C6 C5 C7 117.98(13) . 7_655 ?
C6 C5 C3 119.00(12) . . ?
C7 C5 C3 123.01(12) 7_655 . ?
C6 C7 C5 119.29(12) . 7_655 ?
C6 C7 C8 120.18(12) . . ?
C5 C7 C8 120.45(12) 7_655 . ?
C4 C3 C2 105.29(13) . . ?
C4 C3 C5 128.69(13) . . ?
C2 C3 C5 125.99(13) . . ?
C9 C8 C7 126.49(12) . . ?
C9 C8 H8 116.8 . . ?
C7 C8 H8 116.8 . . ?
C5 C6 C7 122.72(13) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
N2 C11 C9 178.96(16) . . ?
C1 C2 C3 107.12(15) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
N1 C10 C9 177.97(18) . . ?
O1 C4 C3 111.25(14) . . ?
O1 C4 H4 124.4 . . ?
C3 C4 H4 124.4 . . ?
C2 C1 O1 110.51(14) . . ?
C2 C1 H1 124.7 . . ?
O1 C1 H1 124.7 . . ?

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
C6 C5 C3 C4 144.75(16) . . . . ?
C7 C5 C3 C4 -36.3(2) 7_655 . . . ?
C6 C5 C3 C2 -37.4(2) . . . . ?
C7 C5 C3 C2 141.49(16) 7_655 . . . ?
C10 C9 C8 C7 2.9(2) . . . . ?
C11 C9 C8 C7 -178.32(14) . . . . ?
C6 C7 C8 C9 39.6(2) . . . . ?
C5 C7 C8 C9 -143.65(15) 7_655 . . . ?
C7 C5 C6 C7 -0.8(2) 7_655 . . . ?
C3 C5 C6 C7 178.14(13) . . . . ?
C5 C7 C6 C5 0.8(2) 7_655 . . . ?
C8 C7 C6 C5 177.61(13) . . . . ?
C4 C3 C2 C1 0.79(19) . . . . ?
C5 C3 C2 C1 -177.46(15) . . . . ?
C1 O1 C4 C3 -0.13(19) . . . . ?
C2 C3 C4 O1 -0.40(19) . . . . ?
C5 C3 C4 O1 177.78(13) . . . . ?
C3 C2 C1 O1 -0.9(2) . . . . ?
C4 O1 C1 C2 0.7(2) . . . . ?

_refine_diff_density_max         0.131
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.031

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_zhangjinnan20151014_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1439334'
_audit_update_record             
;
2015-11-27 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2015-10-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H14 N4'
_chemical_formula_sum            'C26 H14 N4'
_chemical_formula_weight         382.41
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.4262(9)
_cell_length_b                   7.2914(5)
_cell_length_c                   12.8993(8)
_cell_angle_alpha                90
_cell_angle_beta                 118.312(3)
_cell_angle_gamma                90
_cell_volume                     1028.92(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4303
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.414
_cell_measurement_theta_min      3.139
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1211 before and 0.0438 after correction.
The Ratio of minimum to maximum transmission is 0.4561.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.1036
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2967
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.511
_diffrn_reflns_theta_min         3.320
_diffrn_ambient_temperature      293
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1601
_reflns_number_total             2085
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2085
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1071P)²+0.3496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2154
_refine_ls_wR_factor_ref         0.2330
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.95887(18) 0.0842(3) 0.07266(17) 0.0314(5) Uani 1 1 d . . . . .
C2 C 0.90260(19) 0.1196(3) -0.04813(18) 0.0338(5) Uani 1 1 d . . . . .
H2 H 0.8370 0.2006 -0.0801 0.041 Uiso 1 1 calc R . . . .
C3 C 0.92250(19) 0.1834(3) 0.14950(18) 0.0344(5) Uani 1 1 d . . . . .
H3 H 0.9839 0.2064 0.2257 0.041 Uiso 1 1 calc R . . . .
C4 C 1.1209(2) -0.0874(3) 0.24957(18) 0.0363(6) Uani 1 1 d . . . . .
C5 C 1.05859(18) -0.0375(3) 0.12251(18) 0.0317(5) Uani 1 1 d . . . . .
C6 C 0.8105(2) 0.2450(3) 0.12242(19) 0.0379(6) Uani 1 1 d . . . . .
C7 C 1.2468(2) -0.0789(4) 0.3143(2) 0.0464(6) Uani 1 1 d . . . . .
H7 H 1.2927 -0.0397 0.2788 0.056 Uiso 1 1 calc R . . . .
C8 C 1.0543(3) -0.1469(4) 0.3044(2) 0.0497(7) Uani 1 1 d . . . . .
H8 H 0.9694 -0.1522 0.2621 0.060 Uiso 1 1 calc R . . . .
C9 C 0.7022(2) 0.2102(4) 0.0135(2) 0.0454(6) Uani 1 1 d . . . . .
C10 C 1.3049(3) -0.1289(4) 0.4323(2) 0.0609(8) Uani 1 1 d . . . . .
H10 H 1.3896 -0.1216 0.4758 0.073 Uiso 1 1 calc R . . . .
C11 C 0.7920(3) 0.3463(4) 0.2082(2) 0.0526(7) Uani 1 1 d . . . . .
C12 C 1.2379(3) -0.1892(4) 0.4855(3) 0.0679(10) Uani 1 1 d . . . . .
H12 H 1.2773 -0.2234 0.5644 0.082 Uiso 1 1 calc R . . . .
C13 C 1.1139(3) -0.1987(4) 0.4221(3) 0.0657(9) Uani 1 1 d . . . . .
H13 H 1.0687 -0.2401 0.4579 0.079 Uiso 1 1 calc R . . . .
N14 N 0.6147(2) 0.1850(4) -0.0715(2) 0.0703(8) Uani 1 1 d . . . . .
N1 N 0.7768(3) 0.4259(5) 0.2762(3) 0.0856(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.396(3) . ?
C1 C3 1.461(3) . ?
C1 C5 1.407(3) . ?
C2 H2 0.9300 . ?
C2 C5 1.397(3) 3_755 ?
C3 H3 0.9300 . ?
C3 C6 1.342(3) . ?
C4 C5 1.488(3) . ?
C4 C7 1.382(3) . ?
C4 C8 1.388(3) . ?
C5 C2 1.397(3) 3_755 ?
C6 C9 1.433(3) . ?
C6 C11 1.437(3) . ?
C7 H7 0.9300 . ?
C7 C10 1.389(3) . ?
C8 H8 0.9300 . ?
C8 C13 1.389(4) . ?
C9 N14 1.135(3) . ?
C10 H10 0.9300 . ?
C10 C12 1.378(5) . ?
C11 N1 1.140(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.362(5) . ?
C13 H13 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
C2 C1 C3 120.87(19) . . ?
C2 C1 C5 119.52(18) . . ?
C5 C1 C3 119.39(19) . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C5 122.28(19) . 3_755 ?
C5 C2 H2 118.9 3_755 . ?
C1 C3 H3 116.4 . . ?
C6 C3 C1 127.3(2) . . ?
C6 C3 H3 116.4 . . ?
C7 C4 C5 120.2(2) . . ?
C7 C4 C8 118.9(2) . . ?
C8 C4 C5 120.9(2) . . ?
C1 C5 C4 122.87(18) . . ?
C2 C5 C1 118.20(19) 3_755 . ?
C2 C5 C4 118.89(18) 3_755 . ?
C3 C6 C9 124.9(2) . . ?
C3 C6 C11 119.8(2) . . ?
C9 C6 C11 115.3(2) . . ?
C4 C7 H7 119.9 . . ?
C4 C7 C10 120.1(3) . . ?
C10 C7 H7 119.9 . . ?
C4 C8 H8 119.9 . . ?
C4 C8 C13 120.3(3) . . ?
C13 C8 H8 119.9 . . ?
N14 C9 C6 178.2(3) . . ?
C7 C10 H10 119.8 . . ?
C12 C10 C7 120.4(3) . . ?
C12 C10 H10 119.8 . . ?
N1 C11 C6 179.5(4) . . ?
C10 C12 H12 120.1 . . ?
C13 C12 C10 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.5(3) . . ?
C12 C13 H13 119.7 . . ?

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
C1 C3 C6 C9 5.5(4) . . . . ?
C1 C3 C6 C11 -177.8(2) . . . . ?
C2 C1 C3 C6 33.2(3) . . . . ?
C2 C1 C5 C2 -0.3(3) . . . 3_755 ?
C2 C1 C5 C4 -177.88(19) . . . . ?
C3 C1 C2 C5 175.03(19) . . . 3_755 ?
C3 C1 C5 C2 -175.09(18) . . . 3_755 ?
C3 C1 C5 C4 7.3(3) . . . . ?
C4 C7 C10 C12 0.8(4) . . . . ?
C4 C8 C13 C12 0.9(4) . . . . ?
C5 C1 C2 C5 0.3(3) . . . 3_755 ?
C5 C1 C3 C6 -152.1(2) . . . . ?
C5 C4 C7 C10 -178.8(2) . . . . ?
C5 C4 C8 C13 177.9(2) . . . . ?
C7 C4 C5 C1 -130.8(2) . . . . ?
C7 C4 C5 C2 51.6(3) . . . 3_755 ?
C7 C4 C8 C13 -0.6(4) . . . . ?
C7 C10 C12 C13 -0.5(4) . . . . ?
C8 C4 C5 C1 50.7(3) . . . . ?
C8 C4 C5 C2 -126.9(2) . . . 3_755 ?
C8 C4 C7 C10 -0.2(4) . . . . ?
C10 C12 C13 C8 -0.4(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_exp_11647
_database_code_depnum_ccdc_archive 'CCDC 1442404'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2015-12-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H14 N4 S2'
_chemical_formula_sum            'C24 H14 N4 S2'
_chemical_formula_weight         422.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         CNS
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0866(3)
_cell_length_b                   10.3527(4)
_cell_length_c                   11.6224(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.969(4)
_cell_angle_gamma                90
_cell_volume                     1056.23(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3122
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.5460
_cell_measurement_theta_min      3.9370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.423
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63861
_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    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             436
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8164
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.146
_diffrn_reflns_theta_min         5.038
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   34.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   38.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega   -3.00   32.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega   21.00   76.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega   21.00   55.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -       55.5397 -125.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega   26.00  119.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  120.0000 93

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00   69.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   -9.00   50.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -       55.5397    0.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
  9 omega   54.00   94.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
 10 omega   48.00  115.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
 11 omega   89.00  178.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000   90.0000 89

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00   78.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   85.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
 14 omega   66.00   92.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   59.00   85.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   52.00   88.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -50.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
 17 omega   45.00   70.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00   92.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
 19 omega   54.00   82.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 20 omega  -30.00   70.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
 21 omega  -72.00   26.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 22 omega   34.00  124.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
 23 omega   18.00  113.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -       55.5397 -125.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 24 omega   25.00  126.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 25 omega   30.00  128.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -       55.5397   37.0000  -60.0000 98

#__ type_ start__ end____ width___ exp.time_
 26 omega   85.00  178.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
 27 omega   77.00  178.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 28 omega   39.00  149.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -91.0000 -150.0000 110

#__ type_ start__ end____ width___ exp.time_
 29 omega   85.00  140.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
 30 omega   85.00  178.00   1.0000    4.1600
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000  -30.0000 93
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1348487000
_diffrn_orient_matrix_UB_12      0.0371376000
_diffrn_orient_matrix_UB_13      0.0509270000
_diffrn_orient_matrix_UB_21      -0.1101554000
_diffrn_orient_matrix_UB_22      -0.0708073000
_diffrn_orient_matrix_UB_23      -0.1039299000
_diffrn_orient_matrix_UB_31      0.0222039000
_diffrn_orient_matrix_UB_32      -0.1254826000
_diffrn_orient_matrix_UB_33      0.0736623000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1761
_reflns_number_total             2055
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+0.2959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1118
_refine_special_details          
;
 ?
;
_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), C4(H4), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9488(2) 0.62544(18) 0.48252(15) 0.0422(4) Uani 1 1 d . . . . .
H1 H 0.9148 0.7104 0.4713 0.051 Uiso 1 1 calc R . . . .
C2 C 0.88013(19) 0.53282(17) 0.39965(15) 0.0404(4) Uani 1 1 d . . . . .
C3 C 0.93289(19) 0.40450(17) 0.41792(15) 0.0401(4) Uani 1 1 d . . . . .
C4 C 0.8746(2) 0.30645(18) 0.32753(16) 0.0419(4) Uani 1 1 d . . . . .
H4 H 0.8521 0.3337 0.2487 0.050 Uiso 1 1 calc R . . . .
C5 C 0.8499(2) 0.18183(18) 0.34562(15) 0.0417(4) Uani 1 1 d . . . . .
C6 C 0.8643(2) 0.12678(19) 0.46176(17) 0.0474(4) Uani 1 1 d . . . . .
C7 C 0.7987(2) 0.09524(19) 0.24607(17) 0.0493(5) Uani 1 1 d . . . . .
C8 C 0.7542(2) 0.56814(18) 0.29689(15) 0.0415(4) Uani 1 1 d . . . . .
C9 C 0.6241(2) 0.5024(2) 0.24552(17) 0.0487(4) Uani 1 1 d . . . . .
H9 H 0.5987 0.4235 0.2734 0.058 Uiso 1 1 calc R . . . .
C10 C 0.5321(2) 0.5665(2) 0.14566(18) 0.0525(5) Uani 1 1 d . . . . .
H10 H 0.4399 0.5332 0.1010 0.063 Uiso 1 1 calc R . . . .
C11 C 0.5891(2) 0.6803(2) 0.12045(17) 0.0512(5) Uani 1 1 d . . . . .
C12 C 0.5259(3) 0.7713(3) 0.0189(2) 0.0723(7) Uani 1 1 d . . . . .
H12A H 0.5334 0.8584 0.0481 0.108 Uiso 1 1 calc GR . . . .
H12B H 0.4210 0.7506 -0.0166 0.108 Uiso 1 1 calc GR . . . .
H12C H 0.5829 0.7629 -0.0397 0.108 Uiso 1 1 calc GR . . . .
N1 N 0.8726(3) 0.0832(2) 0.55271(17) 0.0688(5) Uani 1 1 d . . . . .
N2 N 0.7580(3) 0.0294(2) 0.16618(18) 0.0708(6) Uani 1 1 d . . . . .
S1 S 0.76067(5) 0.71115(5) 0.22249(4) 0.05361(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.388(2) . ?
C1 C3 1.396(2) 3_766 ?
C2 C3 1.410(3) . ?
C2 C8 1.471(2) . ?
C3 C1 1.396(2) 3_766 ?
C3 C4 1.459(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.335(3) . ?
C5 C6 1.440(3) . ?
C5 C7 1.442(3) . ?
C6 N1 1.134(3) . ?
C7 N2 1.134(3) . ?
C8 C9 1.361(3) . ?
C8 S1 1.7233(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.409(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.350(3) . ?
C11 C12 1.503(3) . ?
C11 S1 1.7271(19) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C2 C1 H1 118.9 . . ?
C2 C1 C3 122.27(17) . 3_766 ?
C3 C1 H1 118.9 3_766 . ?
C1 C2 C3 118.18(15) . . ?
C1 C2 C8 120.51(16) . . ?
C3 C2 C8 121.31(16) . . ?
C1 C3 C2 119.56(16) 3_766 . ?
C1 C3 C4 120.09(16) 3_766 . ?
C2 C3 C4 120.08(15) . . ?
C3 C4 H4 116.4 . . ?
C5 C4 C3 127.12(17) . . ?
C5 C4 H4 116.4 . . ?
C4 C5 C6 123.49(17) . . ?
C4 C5 C7 120.43(17) . . ?
C6 C5 C7 116.01(17) . . ?
N1 C6 C5 178.6(2) . . ?
N2 C7 C5 178.5(2) . . ?
C2 C8 S1 120.04(13) . . ?
C9 C8 C2 129.59(18) . . ?
C9 C8 S1 110.37(14) . . ?
C8 C9 H9 123.5 . . ?
C8 C9 C10 112.92(18) . . ?
C10 C9 H9 123.5 . . ?
C9 C10 H10 122.9 . . ?
C11 C10 C9 114.21(17) . . ?
C11 C10 H10 122.9 . . ?
C10 C11 C12 128.83(19) . . ?
C10 C11 S1 109.97(14) . . ?
C12 C11 S1 121.16(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 S1 C11 92.52(9) . . ?

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
C1 C2 C3 C1 0.0(3) . . . 3_766 ?
C1 C2 C3 C4 -174.06(16) . . . . ?
C1 C2 C8 C9 -140.2(2) . . . . ?
C1 C2 C8 S1 40.5(2) . . . . ?
C1 C3 C4 C5 40.7(3) 3_766 . . . ?
C2 C3 C4 C5 -145.30(19) . . . . ?
C2 C8 C9 C10 -178.33(18) . . . . ?
C2 C8 S1 C11 178.38(15) . . . . ?
C3 C1 C2 C3 0.0(3) 3_766 . . . ?
C3 C1 C2 C8 179.07(17) 3_766 . . . ?
C3 C2 C8 C9 38.8(3) . . . . ?
C3 C2 C8 S1 -140.49(15) . . . . ?
C3 C4 C5 C6 6.3(3) . . . . ?
C3 C4 C5 C7 -176.88(18) . . . . ?
C8 C2 C3 C1 -179.06(16) . . . 3_766 ?
C8 C2 C3 C4 6.9(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C8 S1 C11 -1.00(16) . . . . ?
C9 C10 C11 C12 177.3(2) . . . . ?
C9 C10 C11 S1 -0.4(2) . . . . ?
C10 C11 S1 C8 0.77(17) . . . . ?
C12 C11 S1 C8 -177.1(2) . . . . ?
S1 C8 C9 C10 1.0(2) . . . . ?

_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_exp_11695
_database_code_depnum_ccdc_archive 'CCDC 1442948'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2015-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H28 N6 O4'
_chemical_formula_sum            'C32 H28 N6 O4'
_chemical_formula_weight         560.60
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.3875(9)
_cell_length_b                   6.9526(2)
_cell_length_c                   21.3637(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.544(3)
_cell_angle_gamma                90
_cell_volume                     3014.04(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3723
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.1850
_cell_measurement_theta_min      5.7680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91271
_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    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10227
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.315
_diffrn_reflns_theta_min         4.158
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   37.00   68.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
  3 omega   -3.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega    9.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   -4.00   96.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -99.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
  6 omega   34.00   73.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00  124.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
  8 omega   18.00   72.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -       55.5397 -125.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   63.00   89.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -50.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   63.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   67.00  132.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -63.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 12 omega   49.00  105.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -50.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega   89.00  174.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794   50.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00   91.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 15 omega   46.00   90.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
 16 omega   57.00  172.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -12.0000  -30.0000 115

#__ type_ start__ end____ width___ exp.time_
 17 omega  -21.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 18 omega  -69.00   21.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 19 omega  -13.00   76.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
 20 omega   25.00  126.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  -90.0000 101

#__ type_ start__ end____ width___ exp.time_
 21 omega   34.00  124.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
 22 omega   25.00  126.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
 23 omega   39.00  116.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000   30.0000 77

#__ type_ start__ end____ width___ exp.time_
 24 omega   77.00  116.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
 25 omega  100.00  178.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  111.0000  -30.0000 78

#__ type_ start__ end____ width___ exp.time_
 26 omega   85.00  178.00   1.0000   23.1800
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000  120.0000 93
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0195514000
_diffrn_orient_matrix_UB_12      -0.0598046000
_diffrn_orient_matrix_UB_13      -0.0687102000
_diffrn_orient_matrix_UB_21      0.0332103000
_diffrn_orient_matrix_UB_22      0.1824896000
_diffrn_orient_matrix_UB_23      -0.0229515000
_diffrn_orient_matrix_UB_31      0.0654197000
_diffrn_orient_matrix_UB_32      -0.1105107000
_diffrn_orient_matrix_UB_33      -0.0007760000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2260
_reflns_number_total             2929
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0580P)²+0.9480P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1208
_refine_special_details          
;
 ?
;
_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:
 C4(H4), C7(H7), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38835(7) 0.24724(17) 0.26715(5) 0.0674(4) Uani 1 1 d . . . . .
O2 O 0.42033(7) 0.01854(16) 0.33835(5) 0.0664(4) Uani 1 1 d . . . . .
N1 N 0.20403(9) 0.1888(3) 0.41616(10) 0.0993(6) Uani 1 1 d . . . . .
N2 N 0.31629(10) -0.3446(3) 0.44771(12) 0.1095(8) Uani 1 1 d . . . . .
N3 N 0.44738(7) 0.33340(18) 0.35552(6) 0.0546(4) Uani 1 1 d . . . . .
C1 C 0.25328(9) 0.1152(3) 0.43008(9) 0.0688(5) Uani 1 1 d . . . . .
C2 C 0.31648(9) -0.1810(3) 0.44786(10) 0.0718(5) Uani 1 1 d . . . . .
C3 C 0.31599(8) 0.0254(2) 0.44728(8) 0.0558(4) Uani 1 1 d . . . . .
C4 C 0.37020(8) 0.1330(2) 0.45881(7) 0.0506(4) Uani 1 1 d . . . . .
H4 H 0.3652 0.2652 0.4539 0.061 Uiso 1 1 calc R . . . .
C5 C 0.43646(7) 0.0626(2) 0.47832(6) 0.0442(3) Uani 1 1 d . . . . .
C6 C 0.49176(7) 0.1499(2) 0.45531(6) 0.0436(3) Uani 1 1 d . . . . .
C7 C 0.55380(7) 0.0849(2) 0.47766(6) 0.0455(3) Uani 1 1 d . . . . .
H7 H 0.5905 0.1420 0.4627 0.055 Uiso 1 1 calc R . . . .
C8 C 0.48723(8) 0.3164(2) 0.41267(7) 0.0481(4) Uani 1 1 d . . . . .
C9 C 0.51812(10) 0.4879(2) 0.42310(8) 0.0638(5) Uani 1 1 d . . . . .
H9 H 0.5481 0.5175 0.4573 0.077 Uiso 1 1 calc R . . . .
C10 C 0.49724(12) 0.6137(3) 0.37355(10) 0.0779(6) Uani 1 1 d . . . . .
H10 H 0.5105 0.7408 0.3697 0.093 Uiso 1 1 calc R . . . .
C11 C 0.45519(11) 0.5187(3) 0.33299(9) 0.0731(5) Uani 1 1 d . . . . .
H11 H 0.4345 0.5683 0.2958 0.088 Uiso 1 1 calc R . . . .
C12 C 0.41781(8) 0.1810(2) 0.32051(7) 0.0530(4) Uani 1 1 d . . . . .
C13 C 0.35721(9) 0.1132(3) 0.21901(7) 0.0656(5) Uani 1 1 d . . . . .
C14 C 0.33369(12) 0.2514(4) 0.16671(9) 0.0951(8) Uani 1 1 d . . . . .
H14A H 0.3038 0.3427 0.1821 0.143 Uiso 1 1 calc GR . . . .
H14B H 0.3116 0.1808 0.1323 0.143 Uiso 1 1 calc GR . . . .
H14C H 0.3708 0.3180 0.1527 0.143 Uiso 1 1 calc GR . . . .
C15 C 0.40762(11) -0.0227(3) 0.19802(10) 0.0855(6) Uani 1 1 d . . . . .
H15A H 0.4445 0.0490 0.1857 0.128 Uiso 1 1 calc GR . . . .
H15B H 0.3885 -0.0966 0.1629 0.128 Uiso 1 1 calc GR . . . .
H15C H 0.4222 -0.1077 0.2320 0.128 Uiso 1 1 calc GR . . . .
C16 C 0.30065(12) 0.0132(4) 0.24494(12) 0.1004(8) Uani 1 1 d . . . . .
H16A H 0.3172 -0.0808 0.2754 0.151 Uiso 1 1 calc GR . . . .
H16B H 0.2741 -0.0495 0.2114 0.151 Uiso 1 1 calc GR . . . .
H16C H 0.2744 0.1057 0.2646 0.151 Uiso 1 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 C12 1.3191(18) . ?
O1 C13 1.484(2) . ?
O2 C12 1.1916(18) . ?
N1 C1 1.141(2) . ?
N2 C2 1.137(2) . ?
N3 C8 1.4046(19) . ?
N3 C11 1.390(2) . ?
N3 C12 1.400(2) . ?
C1 C3 1.438(2) . ?
C2 C3 1.435(3) . ?
C3 C4 1.338(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.459(2) . ?
C5 C6 1.410(2) . ?
C5 C7 1.393(2) 5_656 ?
C6 C7 1.384(2) . ?
C6 C8 1.4706(19) . ?
C7 C5 1.393(2) 5_656 ?
C7 H7 0.9300 . ?
C8 C9 1.357(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.407(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.333(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.516(3) . ?
C13 C15 1.496(3) . ?
C13 C16 1.498(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C12 O1 C13 120.54(14) . . ?
C11 N3 C8 107.64(14) . . ?
C11 N3 C12 125.07(14) . . ?
C12 N3 C8 125.73(12) . . ?
N1 C1 C3 178.9(2) . . ?
N2 C2 C3 179.2(2) . . ?
C2 C3 C1 116.19(16) . . ?
C4 C3 C1 120.19(16) . . ?
C4 C3 C2 123.54(16) . . ?
C3 C4 H4 116.9 . . ?
C3 C4 C5 126.22(15) . . ?
C5 C4 H4 116.9 . . ?
C6 C5 C4 120.37(13) . . ?
C7 C5 C4 120.49(13) 5_656 . ?
C7 C5 C6 119.06(13) 5_656 . ?
C5 C6 C8 123.39(13) . . ?
C7 C6 C5 118.31(13) . . ?
C7 C6 C8 118.12(13) . . ?
C5 C7 H7 118.7 5_656 . ?
C6 C7 C5 122.63(13) . 5_656 ?
C6 C7 H7 118.7 . . ?
N3 C8 C6 126.95(13) . . ?
C9 C8 N3 106.80(13) . . ?
C9 C8 C6 126.15(14) . . ?
C8 C9 H9 125.6 . . ?
C8 C9 C10 108.72(16) . . ?
C10 C9 H9 125.6 . . ?
C9 C10 H10 126.0 . . ?
C11 C10 C9 108.05(16) . . ?
C11 C10 H10 126.0 . . ?
N3 C11 H11 125.6 . . ?
C10 C11 N3 108.79(16) . . ?
C10 C11 H11 125.6 . . ?
O1 C12 N3 109.53(13) . . ?
O2 C12 O1 127.55(15) . . ?
O2 C12 N3 122.93(14) . . ?
O1 C13 C14 101.33(17) . . ?
O1 C13 C15 110.11(15) . . ?
O1 C13 C16 109.17(15) . . ?
C15 C13 C14 110.91(17) . . ?
C15 C13 C16 113.1(2) . . ?
C16 C13 C14 111.52(18) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
N3 C8 C9 C10 1.0(2) . . . . ?
C1 C3 C4 C5 178.19(15) . . . . ?
C2 C3 C4 C5 -5.1(3) . . . . ?
C3 C4 C5 C6 142.48(16) . . . . ?
C3 C4 C5 C7 -40.9(2) . . . 5_656 ?
C4 C5 C6 C7 176.65(13) . . . . ?
C4 C5 C6 C8 1.7(2) . . . . ?
C5 C6 C7 C5 0.1(2) . . . 5_656 ?
C5 C6 C8 N3 -52.5(2) . . . . ?
C5 C6 C8 C9 123.33(19) . . . . ?
C6 C8 C9 C10 -175.55(16) . . . . ?
C7 C5 C6 C7 -0.1(2) 5_656 . . . ?
C7 C5 C6 C8 -175.02(13) 5_656 . . . ?
C7 C6 C8 N3 132.55(16) . . . . ?
C7 C6 C8 C9 -51.6(2) . . . . ?
C8 N3 C11 C10 -0.2(2) . . . . ?
C8 N3 C12 O1 -175.02(15) . . . . ?
C8 N3 C12 O2 5.0(3) . . . . ?
C8 C6 C7 C5 175.29(13) . . . 5_656 ?
C8 C9 C10 C11 -1.1(2) . . . . ?
C9 C10 C11 N3 0.8(2) . . . . ?
C11 N3 C8 C6 176.01(16) . . . . ?
C11 N3 C8 C9 -0.46(19) . . . . ?
C11 N3 C12 O1 -11.0(2) . . . . ?
C11 N3 C12 O2 168.97(18) . . . . ?
C12 O1 C13 C14 -177.41(16) . . . . ?
C12 O1 C13 C15 -60.0(2) . . . . ?
C12 O1 C13 C16 64.8(2) . . . . ?
C12 N3 C8 C6 -17.7(3) . . . . ?
C12 N3 C8 C9 165.84(16) . . . . ?
C12 N3 C11 C10 -166.65(18) . . . . ?
C13 O1 C12 O2 -4.5(3) . . . . ?
C13 O1 C12 N3 175.47(14) . . . . ?

_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_exp_11699
_database_code_depnum_ccdc_archive 'CCDC 1443616'
_audit_update_record             
;
2015-12-21 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2015-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C19 H21 N2 O Si)'
_chemical_formula_sum            'C38 H42 N4 O2 Si2'
_chemical_formula_weight         642.93
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C Si O'
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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7516(5)
_cell_length_b                   12.8129(6)
_cell_length_c                   16.8155(9)
_cell_angle_alpha                106.782(5)
_cell_angle_beta                 99.248(5)
_cell_angle_gamma                90.870(4)
_cell_volume                     1981.19(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5653
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.5880
_cell_measurement_theta_min      4.6380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63225
_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    1.078
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             684
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22046
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.272
_diffrn_reflns_theta_min         3.611
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   13.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00   63.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -56.00  -23.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -        0.0000  138.0000  -36.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega  -20.00    9.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  5 omega   30.00   69.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -13.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000   30.0000 87

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega   17.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -99.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
  9 omega  -15.00   36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -19.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
 10 omega    6.00   57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
 11 omega   34.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397 -125.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
 12 omega   19.00  121.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   19.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
 13 omega   52.00   93.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega   86.00  113.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   49.00   94.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
 16 omega   89.00  114.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00   86.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 18 omega   63.00  177.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   12.0000 -150.0000 114

#__ type_ start__ end____ width___ exp.time_
 19 omega   45.00   88.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
 20 omega   57.00   94.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 21 omega   42.00   91.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
 22 omega   96.00  178.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
 23 omega   40.00   71.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 24 omega   41.00  136.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -77.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 25 omega   41.00   87.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
 26 omega   62.00  103.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 27 omega   82.00  148.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  179.0000 -150.0000 66

#__ type_ start__ end____ width___ exp.time_
 28 omega   48.00  106.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 29 omega   44.00  140.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -77.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
 30 omega  -44.00   73.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000  150.0000 117

#__ type_ start__ end____ width___ exp.time_
 31 omega   -4.00   42.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 32 omega  -69.00   21.00   1.0000    7.5200
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 33 omega   25.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 34 omega   25.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 35 omega   25.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
 36 omega   25.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
 37 omega   25.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
 38 omega   25.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 39 omega   25.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
 40 omega  -13.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
 41 omega   34.00  124.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
 42 omega   39.00  164.00   1.0000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   12.0000   60.0000 125
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0972218000
_diffrn_orient_matrix_UB_12      -0.1046085000
_diffrn_orient_matrix_UB_13      -0.0372112000
_diffrn_orient_matrix_UB_21      -0.0131737000
_diffrn_orient_matrix_UB_22      -0.0016384000
_diffrn_orient_matrix_UB_23      0.0897150000
_diffrn_orient_matrix_UB_31      -0.1268980000
_diffrn_orient_matrix_UB_32      0.0699492000
_diffrn_orient_matrix_UB_33      -0.0019801000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4723
_reflns_number_total             7606
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         7606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0993P)²+1.4385P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2009
_refine_ls_wR_factor_ref         0.2412
_refine_special_details          
;
 ?
;
_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:
 C11(H11), C14(H14), C24(H24), C28(H28), C30(H30), C31(H31), C40(H40),
 C41(H41), C44(H44), C45(H45), C48(H48), C4AA(H4AA)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C5AA(H5AA,H5AB,
 H5AC), C2AA(H2AA,H2AB,H2AC), C3AA(H3AA,H3AB,H3AC), C27(H27A,H27B,H27C),
 C29(H29A,H29B,H29C), C1AA(H1AA,H1AB,H1AC), C6AA(H6AA,H6AB,H6AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si2 Si 0.09728(16) 1.11814(10) 0.35586(8) 0.1020(5) Uani 1 1 d . . . . .
Si3 Si 0.3860(2) 0.56835(12) 0.32869(9) 0.1225(6) Uani 1 1 d . . . . .
O1 O 0.3292(3) 0.52080(19) 0.22567(16) 0.0813(7) Uani 1 1 d . . . . .
O4 O 0.0022(3) 1.0337(2) 0.2709(2) 0.1032(10) Uani 1 1 d . . . . .
C6 C 0.0193(3) 0.6053(2) 0.0609(2) 0.0540(7) Uani 1 1 d . . . . .
C7 C 0.0693(3) 0.1043(2) 0.0424(2) 0.0521(7) Uani 1 1 d . . . . .
C10 C 0.1183(3) 0.0331(2) -0.0259(2) 0.0535(7) Uani 1 1 d . . . . .
C11 C -0.0480(3) 0.0688(2) 0.0666(2) 0.0537(7) Uani 1 1 d . . . . .
H11 H -0.0815 0.1150 0.1119 0.064 Uiso 1 1 calc R . . . .
C14 C 0.2731(3) 0.6062(2) 0.0519(2) 0.0580(8) Uani 1 1 d . . . . .
H14 H 0.3032 0.6402 0.1092 0.070 Uiso 1 1 calc R . . . .
C16 C 0.1311(3) 0.5552(2) 0.0256(2) 0.0538(7) Uani 1 1 d . . . . .
N18 N 0.6099(3) 0.6978(3) 0.0594(3) 0.0906(11) Uani 1 1 d . . . . .
C19 C 0.3627(3) 0.6074(2) -0.0003(2) 0.0622(8) Uani 1 1 d . . . . .
C22 C 0.1391(3) 0.2135(2) 0.0908(2) 0.0550(7) Uani 1 1 d . . . . .
C24 C -0.1108(3) 0.5481(2) 0.0333(2) 0.0568(7) Uani 1 1 d . . . . .
H24 H -0.1871 0.5802 0.0550 0.068 Uiso 1 1 calc R . . . .
C26 C 0.0282(3) 0.7158(2) 0.1217(2) 0.0575(7) Uani 1 1 d . . . . .
C28 C 0.1124(3) 0.8019(3) 0.1169(2) 0.0608(8) Uani 1 1 d . . . . .
H28 H 0.1709 0.7888 0.0770 0.073 Uiso 1 1 calc R . . . .
C30 C 0.0602(3) 0.3019(2) 0.1188(2) 0.0604(8) Uani 1 1 d . . . . .
H30 H -0.0364 0.2925 0.1063 0.073 Uiso 1 1 calc R . . . .
C31 C 0.2336(3) 0.0671(3) -0.0611(2) 0.0611(8) Uani 1 1 d . . . . .
H31 H 0.2389 0.1391 -0.0624 0.073 Uiso 1 1 calc R . . . .
C34 C 0.5011(3) 0.6581(3) 0.0331(3) 0.0693(9) Uani 1 1 d . . . . .
C36 C 0.2668(4) 0.4178(3) 0.1829(2) 0.0669(9) Uani 1 1 d . . . . .
C37 C 0.3320(3) 0.0029(3) -0.0915(2) 0.0689(9) Uani 1 1 d . . . . .
C40 C 0.2830(3) 0.2302(3) 0.1113(2) 0.0661(9) Uani 1 1 d . . . . .
H40 H 0.3379 0.1719 0.0941 0.079 Uiso 1 1 calc R . . . .
C41 C -0.0563(3) 0.7389(3) 0.1829(2) 0.0719(9) Uani 1 1 d . . . . .
H41 H -0.1106 0.6825 0.1892 0.086 Uiso 1 1 calc R . . . .
C44 C 0.1106(3) 0.9062(3) 0.1702(2) 0.0684(9) Uani 1 1 d . . . . .
H44 H 0.1708 0.9618 0.1678 0.082 Uiso 1 1 calc R . . . .
C45 C 0.3464(4) 0.3318(3) 0.1568(2) 0.0709(9) Uani 1 1 d . . . . .
H45 H 0.4430 0.3416 0.1695 0.085 Uiso 1 1 calc R . . . .
C48 C 0.1228(4) 0.4037(3) 0.1649(2) 0.0682(9) Uani 1 1 d . . . . .
H48 H 0.0687 0.4620 0.1837 0.082 Uiso 1 1 calc R . . . .
N50 N 0.3611(4) -0.1902(3) -0.0785(4) 0.1236(16) Uani 1 1 d . . . . .
C52 C 0.3273(4) 0.5639(3) -0.0902(3) 0.0773(11) Uani 1 1 d . . . . .
C54 C 0.0204(4) 0.9281(3) 0.2264(3) 0.0761(10) Uani 1 1 d . . . . .
C2 C 0.3458(4) -0.1048(3) -0.0845(3) 0.0833(12) Uani 1 1 d . . . . .
N3 N 0.5257(5) 0.0625(4) -0.1587(4) 0.163(2) Uani 1 1 d . . . . .
C4AA C -0.0612(4) 0.8437(3) 0.2343(3) 0.0831(11) Uani 1 1 d . . . . .
H4AA H -0.1195 0.8577 0.2743 0.100 Uiso 1 1 calc R . . . .
N8 N 0.2989(5) 0.5298(4) -0.1612(3) 0.1150(14) Uani 1 1 d . . . . .
C9 C 0.4387(4) 0.0395(3) -0.1289(3) 0.0990(15) Uani 1 1 d . . . . .
C12 C 0.4534(6) 0.7094(4) 0.3502(3) 0.1156(17) Uani 1 1 d . . . . .
C13 C 0.4986(8) 0.7607(6) 0.4463(4) 0.181(3) Uani 1 1 d . . . . .
H13A H 0.4213 0.7558 0.4742 0.271 Uiso 1 1 calc GR . . . .
H13B H 0.5291 0.8360 0.4580 0.271 Uiso 1 1 calc GR . . . .
H13C H 0.5736 0.7222 0.4665 0.271 Uiso 1 1 calc GR . . . .
C15 C 0.2479(11) 0.5506(8) 0.3866(5) 0.262(7) Uani 1 1 d . . . . .
H15A H 0.1746 0.5972 0.3773 0.392 Uiso 1 1 calc GR . . . .
H15B H 0.2851 0.5695 0.4457 0.392 Uiso 1 1 calc GR . . . .
H15C H 0.2115 0.4759 0.3670 0.392 Uiso 1 1 calc GR . . . .
C18 C 0.2540(6) 1.1692(5) 0.3256(4) 0.149(2) Uani 1 1 d . . . . .
H18A H 0.3117 1.1099 0.3076 0.223 Uiso 1 1 calc GR . . . .
H18B H 0.3052 1.2242 0.3732 0.223 Uiso 1 1 calc GR . . . .
H18C H 0.2261 1.2001 0.2803 0.223 Uiso 1 1 calc GR . . . .
C5AA C 0.0566(11) 1.3171(5) 0.4694(5) 0.202(4) Uani 1 1 d . . . . .
H5AA H 0.0789 1.2859 0.5149 0.303 Uiso 1 1 calc GR . . . .
H5AB H -0.0024 1.3763 0.4851 0.303 Uiso 1 1 calc GR . . . .
H5AC H 0.1408 1.3440 0.4571 0.303 Uiso 1 1 calc GR . . . .
C0AA C -0.0204(8) 1.2285(4) 0.3899(4) 0.133(2) Uani 1 1 d . . . . .
C2AA C 0.5716(8) 0.7122(6) 0.3018(6) 0.190(4) Uani 1 1 d . . . . .
H2AA H 0.6454 0.6710 0.3197 0.285 Uiso 1 1 calc GR . . . .
H2AB H 0.6058 0.7865 0.3127 0.285 Uiso 1 1 calc GR . . . .
H2AC H 0.5381 0.6810 0.2426 0.285 Uiso 1 1 calc GR . . . .
C3AA C 0.1486(8) 1.0455(5) 0.4348(4) 0.157(3) Uani 1 1 d . . . . .
H3AA H 0.0707 1.0002 0.4368 0.235 Uiso 1 1 calc GR . . . .
H3AB H 0.1780 1.0976 0.4892 0.235 Uiso 1 1 calc GR . . . .
H3AC H 0.2239 1.0008 0.4195 0.235 Uiso 1 1 calc GR . . . .
C27 C -0.1507(9) 1.1783(7) 0.4123(6) 0.211(4) Uani 1 1 d . . . . .
H27A H -0.1907 1.1165 0.3660 0.316 Uiso 1 1 calc GR . . . .
H27B H -0.2182 1.2322 0.4228 0.316 Uiso 1 1 calc GR . . . .
H27C H -0.1233 1.1554 0.4617 0.316 Uiso 1 1 calc GR . . . .
C29 C 0.3331(11) 0.7736(6) 0.3210(6) 0.241(5) Uani 1 1 d . . . . .
H29A H 0.3205 0.7586 0.2609 0.362 Uiso 1 1 calc GR . . . .
H29B H 0.3547 0.8504 0.3475 0.362 Uiso 1 1 calc GR . . . .
H29C H 0.2490 0.7518 0.3365 0.362 Uiso 1 1 calc GR . . . .
C1AA C 0.5376(10) 0.4810(6) 0.3562(5) 0.213(4) Uani 1 1 d . . . . .
H1AA H 0.5021 0.4230 0.3743 0.319 Uiso 1 1 calc GR . . . .
H1AB H 0.6064 0.5262 0.4006 0.319 Uiso 1 1 calc GR . . . .
H1AC H 0.5792 0.4505 0.3072 0.319 Uiso 1 1 calc GR . . . .
C6AA C -0.0665(10) 1.2812(6) 0.3207(5) 0.188(3) Uani 1 1 d . . . . .
H6AA H 0.0138 1.3083 0.3047 0.282 Uiso 1 1 calc GR . . . .
H6AB H -0.1230 1.3405 0.3411 0.282 Uiso 1 1 calc GR . . . .
H6AC H -0.1196 1.2280 0.2727 0.282 Uiso 1 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
Si2 O4 1.650(3) . ?
Si2 C18 1.853(5) . ?
Si2 C0AA 1.854(6) . ?
Si2 C3AA 1.842(6) . ?
Si3 O1 1.659(3) . ?
Si3 C12 1.827(5) . ?
Si3 C15 1.831(7) . ?
Si3 C1AA 1.945(8) . ?
O1 C36 1.383(4) . ?
O4 C54 1.374(4) . ?
C6 C16 1.401(4) . ?
C6 C24 1.396(4) . ?
C6 C26 1.480(4) . ?
C7 C10 1.402(4) . ?
C7 C11 1.386(4) . ?
C7 C22 1.489(4) . ?
C10 C11 1.396(4) 2 ?
C10 C31 1.466(4) . ?
C11 C10 1.396(4) 2 ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C14 C16 1.467(4) . ?
C14 C19 1.338(4) . ?
C16 C24 1.394(4) 2_565 ?
N18 C34 1.132(4) . ?
C19 C34 1.441(4) . ?
C19 C52 1.434(6) . ?
C22 C30 1.389(4) . ?
C22 C40 1.389(4) . ?
C24 C16 1.394(4) 2_565 ?
C24 H24 0.9300 . ?
C26 C28 1.394(4) . ?
C26 C41 1.388(4) . ?
C28 H28 0.9300 . ?
C28 C44 1.379(5) . ?
C30 H30 0.9300 . ?
C30 C48 1.384(4) . ?
C31 H31 0.9300 . ?
C31 C37 1.341(4) . ?
C36 C45 1.367(5) . ?
C36 C48 1.386(5) . ?
C37 C2 1.425(6) . ?
C37 C9 1.436(5) . ?
C40 H40 0.9300 . ?
C40 C45 1.382(4) . ?
C41 H41 0.9300 . ?
C41 C4AA 1.378(5) . ?
C44 H44 0.9300 . ?
C44 C54 1.367(5) . ?
C45 H45 0.9300 . ?
C48 H48 0.9300 . ?
N50 C2 1.137(5) . ?
C52 N8 1.132(5) . ?
C54 C4AA 1.382(5) . ?
N3 C9 1.129(5) . ?
C4AA H4AA 0.9300 . ?
C12 C13 1.545(7) . ?
C12 C2AA 1.520(8) . ?
C12 C29 1.540(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C5AA H5AA 0.9600 . ?
C5AA H5AB 0.9600 . ?
C5AA H5AC 0.9600 . ?
C5AA C0AA 1.554(9) . ?
C0AA C27 1.561(9) . ?
C0AA C6AA 1.518(9) . ?
C2AA H2AA 0.9600 . ?
C2AA H2AB 0.9600 . ?
C2AA H2AC 0.9600 . ?
C3AA H3AA 0.9600 . ?
C3AA H3AB 0.9600 . ?
C3AA H3AC 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C1AA H1AA 0.9600 . ?
C1AA H1AB 0.9600 . ?
C1AA H1AC 0.9600 . ?
C6AA H6AA 0.9600 . ?
C6AA H6AB 0.9600 . ?
C6AA H6AC 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
O4 Si2 C18 108.7(2) . . ?
O4 Si2 C0AA 103.2(3) . . ?
O4 Si2 C3AA 109.5(3) . . ?
C18 Si2 C0AA 111.8(3) . . ?
C3AA Si2 C18 110.2(4) . . ?
C3AA Si2 C0AA 113.2(3) . . ?
O1 Si3 C12 107.0(2) . . ?
O1 Si3 C15 110.1(3) . . ?
O1 Si3 C1AA 107.3(3) . . ?
C12 Si3 C15 115.0(4) . . ?
C12 Si3 C1AA 109.3(3) . . ?
C15 Si3 C1AA 107.8(5) . . ?
C36 O1 Si3 126.0(2) . . ?
C54 O4 Si2 131.1(3) . . ?
C16 C6 C26 124.8(2) . . ?
C24 C6 C16 117.0(3) . . ?
C24 C6 C26 118.1(3) . . ?
C10 C7 C22 123.3(2) . . ?
C11 C7 C10 117.5(3) . . ?
C11 C7 C22 119.2(3) . . ?
C7 C10 C31 121.5(3) . . ?
C11 C10 C7 119.5(2) 2 . ?
C11 C10 C31 118.8(3) 2 . ?
C7 C11 C10 123.0(3) . 2 ?
C7 C11 H11 118.5 . . ?
C10 C11 H11 118.5 2 . ?
C16 C14 H14 117.6 . . ?
C19 C14 H14 117.6 . . ?
C19 C14 C16 124.8(3) . . ?
C6 C16 C14 121.7(3) . . ?
C24 C16 C6 120.4(2) 2_565 . ?
C24 C16 C14 117.9(3) 2_565 . ?
C14 C19 C34 119.9(3) . . ?
C14 C19 C52 123.3(3) . . ?
C52 C19 C34 116.7(3) . . ?
C30 C22 C7 120.3(3) . . ?
C40 C22 C7 121.9(3) . . ?
C40 C22 C30 117.9(3) . . ?
C6 C24 H24 118.7 . . ?
C16 C24 C6 122.6(3) 2_565 . ?
C16 C24 H24 118.7 2_565 . ?
C28 C26 C6 122.4(3) . . ?
C41 C26 C6 120.1(3) . . ?
C41 C26 C28 117.4(3) . . ?
C26 C28 H28 119.3 . . ?
C44 C28 C26 121.3(3) . . ?
C44 C28 H28 119.3 . . ?
C22 C30 H30 119.4 . . ?
C48 C30 C22 121.2(3) . . ?
C48 C30 H30 119.4 . . ?
C10 C31 H31 117.3 . . ?
C37 C31 C10 125.4(3) . . ?
C37 C31 H31 117.3 . . ?
N18 C34 C19 179.9(5) . . ?
O1 C36 C48 119.2(3) . . ?
C45 C36 O1 120.3(3) . . ?
C45 C36 C48 120.4(3) . . ?
C31 C37 C2 123.1(3) . . ?
C31 C37 C9 122.8(3) . . ?
C2 C37 C9 114.0(3) . . ?
C22 C40 H40 119.3 . . ?
C45 C40 C22 121.3(3) . . ?
C45 C40 H40 119.3 . . ?
C26 C41 H41 119.4 . . ?
C4AA C41 C26 121.3(3) . . ?
C4AA C41 H41 119.4 . . ?
C28 C44 H44 119.9 . . ?
C54 C44 C28 120.1(3) . . ?
C54 C44 H44 119.9 . . ?
C36 C45 C40 119.8(3) . . ?
C36 C45 H45 120.1 . . ?
C40 C45 H45 120.1 . . ?
C30 C48 C36 119.3(3) . . ?
C30 C48 H48 120.3 . . ?
C36 C48 H48 120.3 . . ?
N8 C52 C19 179.7(6) . . ?
O4 C54 C4AA 119.2(4) . . ?
C44 C54 O4 120.9(3) . . ?
C44 C54 C4AA 119.7(3) . . ?
N50 C2 C37 177.9(4) . . ?
C41 C4AA C54 120.0(3) . . ?
C41 C4AA H4AA 120.0 . . ?
C54 C4AA H4AA 120.0 . . ?
N3 C9 C37 176.0(5) . . ?
C13 C12 Si3 109.4(5) . . ?
C2AA C12 Si3 109.7(4) . . ?
C2AA C12 C13 112.5(6) . . ?
C2AA C12 C29 110.0(7) . . ?
C29 C12 Si3 107.6(5) . . ?
C29 C12 C13 107.5(6) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si3 C15 H15A 109.5 . . ?
Si3 C15 H15B 109.5 . . ?
Si3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Si2 C18 H18A 109.5 . . ?
Si2 C18 H18B 109.5 . . ?
Si2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H5AA C5AA H5AB 109.5 . . ?
H5AA C5AA H5AC 109.5 . . ?
H5AB C5AA H5AC 109.5 . . ?
C0AA C5AA H5AA 109.5 . . ?
C0AA C5AA H5AB 109.5 . . ?
C0AA C5AA H5AC 109.5 . . ?
C5AA C0AA Si2 109.4(6) . . ?
C5AA C0AA C27 109.2(6) . . ?
C27 C0AA Si2 108.5(4) . . ?
C6AA C0AA Si2 111.2(4) . . ?
C6AA C0AA C5AA 109.0(6) . . ?
C6AA C0AA C27 109.5(7) . . ?
C12 C2AA H2AA 109.5 . . ?
C12 C2AA H2AB 109.5 . . ?
C12 C2AA H2AC 109.5 . . ?
H2AA C2AA H2AB 109.5 . . ?
H2AA C2AA H2AC 109.5 . . ?
H2AB C2AA H2AC 109.5 . . ?
Si2 C3AA H3AA 109.5 . . ?
Si2 C3AA H3AB 109.5 . . ?
Si2 C3AA H3AC 109.5 . . ?
H3AA C3AA H3AB 109.5 . . ?
H3AA C3AA H3AC 109.5 . . ?
H3AB C3AA H3AC 109.5 . . ?
C0AA C27 H27A 109.5 . . ?
C0AA C27 H27B 109.5 . . ?
C0AA C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C12 C29 H29A 109.5 . . ?
C12 C29 H29B 109.5 . . ?
C12 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Si3 C1AA H1AA 109.5 . . ?
Si3 C1AA H1AB 109.5 . . ?
Si3 C1AA H1AC 109.5 . . ?
H1AA C1AA H1AB 109.5 . . ?
H1AA C1AA H1AC 109.5 . . ?
H1AB C1AA H1AC 109.5 . . ?
C0AA C6AA H6AA 109.5 . . ?
C0AA C6AA H6AB 109.5 . . ?
C0AA C6AA H6AC 109.5 . . ?
H6AA C6AA H6AB 109.5 . . ?
H6AA C6AA H6AC 109.5 . . ?
H6AB C6AA H6AC 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
Si2 O4 C54 C44 -79.6(5) . . . . ?
Si2 O4 C54 C4AA 105.2(4) . . . . ?
Si3 O1 C36 C45 -85.5(4) . . . . ?
Si3 O1 C36 C48 96.3(4) . . . . ?
O1 Si3 C12 C13 176.1(4) . . . . ?
O1 Si3 C12 C2AA -60.1(5) . . . . ?
O1 Si3 C12 C29 59.6(6) . . . . ?
O1 C36 C45 C40 -177.5(3) . . . . ?
O1 C36 C48 C30 177.0(3) . . . . ?
O4 Si2 C0AA C5AA -178.7(4) . . . . ?
O4 Si2 C0AA C27 62.1(6) . . . . ?
O4 Si2 C0AA C6AA -58.3(6) . . . . ?
O4 C54 C4AA C41 172.3(4) . . . . ?
C6 C26 C28 C44 174.8(3) . . . . ?
C6 C26 C41 C4AA -172.9(3) . . . . ?
C7 C10 C31 C37 143.9(4) . . . . ?
C7 C22 C30 C48 179.0(3) . . . . ?
C7 C22 C40 C45 -179.5(3) . . . . ?
C10 C7 C11 C10 -0.2(5) . . . 2 ?
C10 C7 C22 C30 141.4(3) . . . . ?
C10 C7 C22 C40 -40.3(5) . . . . ?
C10 C31 C37 C2 -7.5(6) . . . . ?
C10 C31 C37 C9 177.0(4) . . . . ?
C11 C7 C10 C11 0.2(5) . . . 2 ?
C11 C7 C10 C31 174.2(3) . . . . ?
C11 C7 C22 C30 -40.2(4) . . . . ?
C11 C7 C22 C40 138.2(3) . . . . ?
C11 C10 C31 C37 -42.0(5) 2 . . . ?
C16 C6 C24 C16 1.2(5) . . . 2_565 ?
C16 C6 C26 C28 36.5(5) . . . . ?
C16 C6 C26 C41 -148.1(3) . . . . ?
C16 C14 C19 C34 -178.6(3) . . . . ?
C16 C14 C19 C52 3.8(5) . . . . ?
C19 C14 C16 C6 -139.0(3) . . . . ?
C19 C14 C16 C24 44.1(4) . . . 2_565 ?
C22 C7 C10 C11 178.6(3) . . . 2 ?
C22 C7 C10 C31 -7.3(5) . . . . ?
C22 C7 C11 C10 -178.7(3) . . . 2 ?
C22 C30 C48 C36 0.6(5) . . . . ?
C22 C40 C45 C36 0.5(5) . . . . ?
C24 C6 C16 C14 -178.0(3) . . . . ?
C24 C6 C16 C24 -1.2(5) . . . 2_565 ?
C24 C6 C26 C28 -140.3(3) . . . . ?
C24 C6 C26 C41 35.1(4) . . . . ?
C26 C6 C16 C14 5.2(5) . . . . ?
C26 C6 C16 C24 -178.0(3) . . . 2_565 ?
C26 C6 C24 C16 178.3(3) . . . 2_565 ?
C26 C28 C44 C54 -3.1(5) . . . . ?
C26 C41 C4AA C54 -0.9(6) . . . . ?
C28 C26 C41 C4AA 2.8(5) . . . . ?
C28 C44 C54 O4 -170.2(3) . . . . ?
C28 C44 C54 C4AA 5.0(6) . . . . ?
C30 C22 C40 C45 -1.2(5) . . . . ?
C40 C22 C30 C48 0.6(5) . . . . ?
C41 C26 C28 C44 -0.7(5) . . . . ?
C44 C54 C4AA C41 -3.0(6) . . . . ?
C45 C36 C48 C30 -1.2(5) . . . . ?
C48 C36 C45 C40 0.7(5) . . . . ?
C12 Si3 O1 C36 -178.3(3) . . . . ?
C15 Si3 O1 C36 -52.7(5) . . . . ?
C15 Si3 C12 C13 53.4(7) . . . . ?
C15 Si3 C12 C2AA 177.2(6) . . . . ?
C15 Si3 C12 C29 -63.1(7) . . . . ?
C18 Si2 O4 C54 74.9(5) . . . . ?
C18 Si2 C0AA C5AA -62.1(5) . . . . ?
C18 Si2 C0AA C27 178.8(5) . . . . ?
C18 Si2 C0AA C6AA 58.3(6) . . . . ?
C0AA Si2 O4 C54 -166.3(4) . . . . ?
C3AA Si2 O4 C54 -45.5(5) . . . . ?
C3AA Si2 C0AA C5AA 63.0(6) . . . . ?
C3AA Si2 C0AA C27 -56.1(6) . . . . ?
C3AA Si2 C0AA C6AA -176.6(5) . . . . ?
C1AA Si3 O1 C36 64.4(4) . . . . ?
C1AA Si3 C12 C13 -68.0(6) . . . . ?
C1AA Si3 C12 C2AA 55.8(6) . . . . ?
C1AA Si3 C12 C29 175.5(6) . . . . ?

_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_exp_11784
_database_code_depnum_ccdc_archive 'CCDC 1472574'
_audit_update_record             
;
2016-04-06 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2015-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H18 N4 O2'
_chemical_formula_sum            'C28 H18 N4 O2'
_chemical_formula_weight         442.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         CON
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.7023(2)
_cell_length_b                   14.1338(4)
_cell_length_c                   12.7266(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.447(3)
_cell_angle_gamma                90
_cell_volume                     1185.58(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3621
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9270
_cell_measurement_theta_min      8.7080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43449
_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_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             460
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11146
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.228
_diffrn_reflns_theta_min         4.719
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   24.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00    7.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   74.00  122.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
  4 omega    2.00   70.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000  -90.0000 68

#__ type_ start__ end____ width___ exp.time_
  5 omega   62.00  112.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  6 omega   -2.00   93.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -99.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega   48.00   82.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   46.00   94.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  9 omega   89.00  161.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00  133.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -77.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   75.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   92.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
 13 omega   47.00  115.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
 14 omega  -26.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   37.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
 15 omega   34.00  124.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
 16 omega   34.00  124.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 17 omega  -13.00   76.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
 18 omega   34.00  124.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
 19 omega   77.00  178.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 20 omega   77.00  178.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
 21 omega   85.00  178.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
 22 omega   39.00   92.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 23 omega   81.00  178.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000  150.0000 97

#__ type_ start__ end____ width___ exp.time_
 24 omega   39.00   92.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 25 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 26 omega   25.00  126.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
 27 omega   18.00  113.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397 -125.0000  -90.0000 95

#__ type_ start__ end____ width___ exp.time_
 28 omega   25.00  126.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 29 omega   25.00  126.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000    0.0000 101

#__ type_ start__ end____ width___ exp.time_
 30 omega   39.00  116.00   1.0000    3.5800
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000 -120.0000 77
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0875140000
_diffrn_orient_matrix_UB_12      -0.0184299000
_diffrn_orient_matrix_UB_13      -0.1187259000
_diffrn_orient_matrix_UB_21      0.0070471000
_diffrn_orient_matrix_UB_22      -0.1073512000
_diffrn_orient_matrix_UB_23      0.0213110000
_diffrn_orient_matrix_UB_31      -0.2166327000
_diffrn_orient_matrix_UB_32      0.0039347000
_diffrn_orient_matrix_UB_33      0.0245406000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1890
_reflns_number_total             2302
_reflns_odcompleteness_completeness 99.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0716P)²+0.2304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1373
_refine_special_details          ?
_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), C3(H3), C4(H4), C6(H6), C8(H8), C10(H10)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3033(2) 0.67797(11) 0.80451(11) 0.0761(5) Uani 1 1 d . . . . .
N1 N 0.4929(3) 0.61324(14) 0.24285(17) 0.0786(6) Uani 1 1 d . . . . .
N2 N 0.9355(3) 0.70136(13) 0.05520(12) 0.0718(5) Uani 1 1 d . . . . .
C1 C 0.6516(3) 0.63176(13) 0.79947(13) 0.0537(5) Uani 1 1 d . . . . .
H1 H 0.6940 0.6431 0.8721 0.064 Uiso 1 1 calc R . . . .
C2 C 0.4529(3) 0.64855(13) 0.75177(14) 0.0520(4) Uani 1 1 d . . . . .
C3 C 0.3931(3) 0.63623(12) 0.64269(14) 0.0491(4) Uani 1 1 d . . . . .
H3 H 0.2611 0.6507 0.6099 0.059 Uiso 1 1 calc R . . . .
C4 C 0.5291(2) 0.60255(11) 0.58293(12) 0.0427(4) Uani 1 1 d . . . . .
H4 H 0.4878 0.5945 0.5097 0.051 Uiso 1 1 calc R . . . .
C5 C 0.7279(2) 0.58026(11) 0.63009(11) 0.0388(4) Uani 1 1 d . . . . .
C6 C 0.7875(3) 0.59789(12) 0.73841(12) 0.0465(4) Uani 1 1 d . . . . .
H6 H 0.9213 0.5867 0.7707 0.056 Uiso 1 1 calc R . . . .
C7 C 0.8675(2) 0.53850(11) 0.56447(11) 0.0374(3) Uani 1 1 d . . . . .
C8 C 0.8794(2) 0.57655(11) 0.46535(11) 0.0390(4) Uani 1 1 d . . . . .
H8 H 0.7986 0.6284 0.4412 0.047 Uiso 1 1 calc R . . . .
C9 C 1.0077(2) 0.54006(11) 0.40042(11) 0.0381(4) Uani 1 1 d . . . . .
C10 C 1.0237(2) 0.58684(11) 0.29977(11) 0.0412(4) Uani 1 1 d . . . . .
H10 H 1.1527 0.5910 0.2828 0.049 Uiso 1 1 calc R . . . .
C11 C 0.8704(2) 0.62439(11) 0.22935(12) 0.0429(4) Uani 1 1 d . . . . .
C12 C 0.6606(3) 0.61805(12) 0.23841(13) 0.0509(4) Uani 1 1 d . . . . .
C13 C 0.9083(3) 0.66873(13) 0.13300(13) 0.0517(4) Uani 1 1 d . . . . .
C14 C 0.3529(4) 0.6865(2) 0.9168(2) 0.1069(10) Uani 1 1 d . . . . .
H14A H 0.4599 0.7320 0.9352 0.160 Uiso 1 1 calc GR . . . .
H14B H 0.3968 0.6263 0.9474 0.160 Uiso 1 1 calc GR . . . .
H14C H 0.2356 0.7071 0.9440 0.160 Uiso 1 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 C2 1.368(2) . ?
O1 C14 1.412(3) . ?
N1 C12 1.138(2) . ?
N2 C13 1.136(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.385(2) . ?
C2 C3 1.384(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(2) . ?
C5 C6 1.386(2) . ?
C5 C7 1.485(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(2) . ?
C7 C9 1.413(2) 3_766 ?
C8 H8 0.9300 . ?
C8 C9 1.3951(19) . ?
C9 C7 1.413(2) 3_766 ?
C9 C10 1.463(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.344(2) . ?
C11 C12 1.435(2) . ?
C11 C13 1.440(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C2 O1 C14 117.60(17) . . ?
C2 C1 H1 120.2 . . ?
C2 C1 C6 119.51(15) . . ?
C6 C1 H1 120.2 . . ?
O1 C2 C1 124.81(16) . . ?
O1 C2 C3 115.19(17) . . ?
C1 C2 C3 120.01(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.91(16) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.19(14) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C7 119.88(13) . . ?
C6 C5 C4 117.90(14) . . ?
C6 C5 C7 122.22(14) . . ?
C1 C6 C5 121.31(16) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C5 120.23(13) . . ?
C8 C7 C9 117.64(13) . 3_766 ?
C9 C7 C5 122.13(13) 3_766 . ?
C7 C8 H8 118.7 . . ?
C7 C8 C9 122.59(14) . . ?
C9 C8 H8 118.7 . . ?
C7 C9 C10 119.93(13) 3_766 . ?
C8 C9 C7 119.76(13) . 3_766 ?
C8 C9 C10 120.17(13) . . ?
C9 C10 H10 116.8 . . ?
C11 C10 C9 126.44(14) . . ?
C11 C10 H10 116.8 . . ?
C10 C11 C12 124.30(14) . . ?
C10 C11 C13 120.56(15) . . ?
C12 C11 C13 114.98(14) . . ?
N1 C12 C11 178.26(19) . . ?
N2 C13 C11 177.9(2) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 C2 C3 C4 -176.91(16) . . . . ?
C1 C2 C3 C4 3.4(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -3.4(2) . . . . ?
C3 C4 C5 C7 176.28(14) . . . . ?
C4 C5 C6 C1 3.4(2) . . . . ?
C4 C5 C7 C8 45.8(2) . . . . ?
C4 C5 C7 C9 -134.35(15) . . . 3_766 ?
C5 C7 C8 C9 -179.93(14) . . . . ?
C6 C1 C2 O1 177.01(17) . . . . ?
C6 C1 C2 C3 -3.3(3) . . . . ?
C6 C5 C7 C8 -134.53(16) . . . . ?
C6 C5 C7 C9 45.3(2) . . . 3_766 ?
C7 C5 C6 C1 -176.21(15) . . . . ?
C7 C8 C9 C7 -0.3(2) . . . 3_766 ?
C7 C8 C9 C10 -176.00(13) . . . . ?
C7 C9 C10 C11 143.70(17) 3_766 . . . ?
C8 C9 C10 C11 -40.6(2) . . . . ?
C9 C7 C8 C9 0.3(2) 3_766 . . . ?
C9 C10 C11 C12 -4.9(3) . . . . ?
C9 C10 C11 C13 179.88(15) . . . . ?
C14 O1 C2 C1 -3.9(3) . . . . ?
C14 O1 C2 C3 176.5(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_exp_12595
_database_code_depnum_ccdc_archive 'CCDC 1499316'
_audit_update_record             
;
2016-08-16 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2016-08-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         '0.09(C28 H18 N4 O2)'
_chemical_formula_sum            'C2.545 H1.636 N0.364 O0.182'
_chemical_formula_weight         40.23
_chemical_oxdiff_formula         'C O N'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      2
_cell_length_a                   6.5174(4)
_cell_length_b                   9.8469(5)
_cell_length_c                   10.3476(5)
_cell_angle_alpha                113.309(5)
_cell_angle_beta                 95.997(5)
_cell_angle_gamma                104.217(5)
_cell_volume                     575.82(7)
_cell_formula_units_Z            11
_cell_measurement_reflns_used    4977
_cell_measurement_theta_max      72.4360
_cell_measurement_theta_min      8.4320
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65460
_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    1.2759
_exptl_crystal_F_000             230.7271
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10627
_diffrn_reflns_theta_full        72.6743
_diffrn_reflns_theta_max         72.67
_diffrn_reflns_theta_min         4.78
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.9851
_diffrn_measured_fraction_theta_max 0.9851
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   78.00  103.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  152.0000  136.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  -14.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  -19.0000 -150.0000 109

#__ type_ start__ end____ width___ exp.time_
  7 omega    3.00   76.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  -57.0000   30.0000 73

#__ type_ start__ end____ width___ exp.time_
  8 omega   63.00  127.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   37.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  9 omega  -12.00   78.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  -77.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 10 omega   25.00   98.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  -99.0000  -60.0000 73

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -25.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega  146.00  172.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   50.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   49.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -37.0000  -90.0000 46

#__ type_ start__ end____ width___ exp.time_
 14 omega   73.00  128.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -77.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 15 omega   90.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   50.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega   92.00  149.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   50.0000  -30.0000 57

#__ type_ start__ end____ width___ exp.time_
 17 omega   54.00   96.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -25.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
 18 omega   56.00  106.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -50.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00  115.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044 -111.0000   90.0000 73

#__ type_ start__ end____ width___ exp.time_
 20 omega   46.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044 -111.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
 21 omega   44.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -37.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 22 omega   51.00  139.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -12.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
 23 omega   55.00   81.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega  104.00  141.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -77.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 25 omega   78.00  149.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -91.0000  -90.0000 71

#__ type_ start__ end____ width___ exp.time_
 26 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 27 omega  -74.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  152.0000  136.0000 60

#__ type_ start__ end____ width___ exp.time_
 28 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
 29 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
 30 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000  150.0000 100

#__ type_ start__ end____ width___ exp.time_
 31 omega   17.00  113.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522 -124.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
 32 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
 33 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 34 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000 -180.0000 96

#__ type_ start__ end____ width___ exp.time_
 35 omega   89.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   63.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 36 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  -90.0000 96

#__ type_ start__ end____ width___ exp.time_
 37 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
 38 omega   90.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   50.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
 39 omega   39.00  115.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044 -111.0000    0.0000 76

#__ type_ start__ end____ width___ exp.time_
 40 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
 41 omega   40.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   12.0000 -180.0000 138

#__ type_ start__ end____ width___ exp.time_
 42 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
 43 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  -60.0000 96

#__ type_ start__ end____ width___ exp.time_
 44 omega  -21.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
 45 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
 46 omega   17.00  113.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522 -124.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
 47 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
 48 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
 49 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000  120.0000 100

#__ type_ start__ end____ width___ exp.time_
 50 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
 51 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 52 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000   60.0000 96

#__ type_ start__ end____ width___ exp.time_
 53 omega   56.00  150.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  179.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 54 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  150.0000 96

#__ type_ start__ end____ width___ exp.time_
 55 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  -30.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0887718000
_diffrn_orient_matrix_UB_12      0.1792574000
_diffrn_orient_matrix_UB_13      0.0713465000
_diffrn_orient_matrix_UB_21      0.0096852000
_diffrn_orient_matrix_UB_22      -0.0027547000
_diffrn_orient_matrix_UB_23      -0.1491073000
_diffrn_orient_matrix_UB_31      -0.2338852000
_diffrn_orient_matrix_UB_32      0.0075853000
_diffrn_orient_matrix_UB_33      -0.0194477000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              -12
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2024
_reflns_number_total             2254
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(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  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.1426
_refine_diff_density_min         -0.2216
_refine_diff_density_rms         0.0432
_refine_ls_d_res_high            0.8076
_refine_ls_d_res_low             9.2561
_refine_ls_goodness_of_fit_ref   1.0717
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.0717
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.0929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1177
_olex2_refinement_description    
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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:
 C9(H9), C13(H13), C11(H11), C10(H10), C7(H7), C4(H4)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
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_refinement_flags_posn
C1 C -0.4147(2) 0.56371(15) 0.86745(16) 0.0545(3) Uani 1.000000 .
C2 C -0.1724(2) 0.40530(14) 0.82205(15) 0.0495(3) Uani 1.000000 .
C3 C -0.1987(2) 0.55621(13) 0.86133(13) 0.0432(3) Uani 1.000000 .
C4 C -0.0263(2) 0.67879(13) 0.88877(13) 0.0427(3) Uani 1.000000 .
H4 H 0.1030(2) 0.65792(13) 0.87330(13) 0.0513(4) Uiso 1.000000 R
C5 C -0.01879(19) 0.84166(13) 0.94033(13) 0.0408(3) Uani 1.000000 .
C6 C 0.11689(19) 0.94020(13) 0.89375(13) 0.0410(3) Uani 1.000000 .
C7 C 0.1311(2) 1.09690(13) 0.95499(13) 0.0427(3) Uani 1.000000 .
H7 H 0.2189(2) 1.16315(13) 0.92488(13) 0.0513(3) Uiso 1.000000 R
C8 C 0.2385(2) 0.88243(13) 0.78138(13) 0.0428(3) Uani 1.000000 .
C9 C 0.1451(2) 0.74262(15) 0.65708(15) 0.0563(4) Uani 1.000000 .
H9 H 0.0036(2) 0.68255(15) 0.64496(15) 0.0676(4) Uiso 1.000000 R
C10 C 0.4489(2) 0.96916(14) 0.79374(14) 0.0486(3) Uani 1.000000 .
H10 H 0.5148(2) 1.06295(14) 0.87557(14) 0.0584(4) Uiso 1.000000 R
C11 C 0.5633(2) 0.92042(16) 0.68817(16) 0.0543(3) Uani 1.000000 .
H11 H 0.7038(2) 0.98115(16) 0.69894(16) 0.0652(4) Uiso 1.000000 R
C12 C 0.4672(2) 0.78045(16) 0.56624(16) 0.0566(4) Uani 1.000000 .
C13 C 0.2580(3) 0.69184(17) 0.55208(17) 0.0671(4) Uani 1.000000 .
H13 H 0.1933(3) 0.59723(17) 0.47092(17) 0.0805(5) Uiso 1.000000 R
C14 C 0.7474(3) 0.8239(2) 0.4431(2) 0.0822(5) Uani 1.000000 .
H14a H 0.7922(16) 0.7699(6) 0.3567(9) 0.1232(8) Uiso 1.000000 GR
H14b H 0.7099(8) 0.9106(10) 0.4388(17) 0.1232(8) Uiso 1.000000 GR
H14c H 0.8642(9) 0.8609(14) 0.5255(9) 0.1232(8) Uiso 1.000000 GR
N1 N -0.5857(2) 0.56818(18) 0.8731(2) 0.0837(5) Uani 1.000000 .
N2 N -0.1434(2) 0.28844(14) 0.79284(17) 0.0715(4) Uani 1.000000 .
O1 O 0.5643(2) 0.72095(14) 0.45541(13) 0.0806(4) Uani 1.000000 .


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
C1 C3 1.4337(18) . ?
C1 N1 1.1330(18) . ?
C2 C3 1.4371(16) . ?
C2 N2 1.1378(17) . ?
C3 C4 1.3403(17) . ?
C4 C5 1.4622(16) . ?
C5 C6 1.4120(17) . ?
C5 C7 1.3925(17) 2_577 ?
C6 C7 1.3910(16) . ?
C6 C8 1.4815(16) . ?
C8 C9 1.3942(17) . ?
C8 C10 1.3880(18) . ?
C9 C13 1.3749(19) . ?
C10 C11 1.3825(18) . ?
C11 C12 1.385(2) . ?
C12 C13 1.383(2) . ?
C12 O1 1.3643(16) . ?
C14 O1 1.417(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
N1 C1 C3 179.04(16) . . ?
N2 C2 C3 177.45(15) . . ?
C2 C3 C1 116.08(11) . . ?
C4 C3 C1 124.27(11) . . ?
C4 C3 C2 119.65(11) . . ?
C5 C4 C3 127.23(11) . . ?
C6 C5 C4 120.13(11) . . ?
C7 C5 C4 119.85(11) 2_577 . ?
C7 C5 C6 119.78(11) 2_577 . ?
C7 C6 C5 117.71(11) . . ?
C8 C6 C5 122.68(10) . . ?
C8 C6 C7 119.59(11) . . ?
C6 C7 C5 122.51(11) . 2_577 ?
C9 C8 C6 121.80(11) . . ?
C10 C8 C6 120.87(11) . . ?
C10 C8 C9 117.29(12) . . ?
C13 C9 C8 121.28(12) . . ?
C11 C10 C8 122.04(12) . . ?
C12 C11 C10 119.49(12) . . ?
C13 C12 C11 119.41(13) . . ?
O1 C12 C11 124.58(13) . . ?
O1 C12 C13 116.01(13) . . ?
C12 C13 C9 120.49(13) . . ?
C14 O1 C12 117.87(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
