# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1500638'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2017-02-02 downloaded from the CCDC.
;
_audit_creation_date             2016-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C11 H9 N2 O)'
_chemical_formula_sum            'C22 H18 N4 O2'
_chemical_formula_weight         370.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H18 N4 O2 '
_chemical_oxdiff_usercomment     'Clear, Colorless, Block'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.2801(4)
_cell_length_b                   12.0904(8)
_cell_length_c                   13.3168(8)
_cell_angle_alpha                114.646(6)
_cell_angle_beta                 103.516(5)
_cell_angle_gamma                93.852(5)
_cell_volume                     877.92(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5160
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.7750
_cell_measurement_theta_min      3.8970
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 2 13 0.0547
9 -3 0 0.0813
0 -1 17 0.0551
-9 3 6 0.0850
1 1 -17 0.0659
5 -1 -16 0.0631
-1 -17 7 0.0476
1 17 -7 0.0459
-3 -13 0 0.0638
-2 14 -14 0.0884

_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.093
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.0000 2.0000 13.0000 -0.2017 0.9717 -0.1518
9.0000 -3.0000 -0.0000 0.1172 -0.7785 -0.6879
-0.0000 -1.0000 17.0000 -0.1092 0.4752 -0.8878
-9.0000 3.0000 6.0000 -0.1779 0.9485 0.3681
1.0000 1.0000 -17.0000 0.1013 -0.5595 0.8053
5.0000 -1.0000 -16.0000 0.1851 -0.8815 0.4585
-1.0000 -17.0000 7.0000 1.0042 0.1709 0.0196
1.0000 17.0000 -7.0000 -1.0042 -0.1709 -0.0196
-3.0000 -13.0000 -0.0000 0.8397 0.1675 0.4847
-2.0000 14.0000 -14.0000 -0.7214 -0.1361 0.6558

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11863
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.10
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  47.00   1.00   30.00    --  -18.14  77.00-120.00   94
  2  ω    -37.00  54.00   1.00   30.00    --  -18.14  37.00  30.00   91
  3  ω    -83.00  -9.00   1.00   30.00    --  -18.14 137.00  27.90   74
  4  ω     -2.00  88.00   1.00   30.00    --   19.23  57.00 -90.00   90
  5  ω    -50.00  41.00   1.00   30.00    --   19.23 -57.00 120.00   91
  6  ω     10.00  61.00   1.00   30.00    --   19.23 -99.00 -60.00   51
  7  ω     -2.00  88.00   1.00   30.00    --   19.23  57.00  30.00   90
  8  ω    -10.00  87.00   1.00   30.00    --   19.23  77.00 120.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0078966000
_diffrn_orient_matrix_UB_12      -0.0627688000
_diffrn_orient_matrix_UB_13      -0.0101131000
_diffrn_orient_matrix_UB_21      -0.0843059000
_diffrn_orient_matrix_UB_22      0.0065729000
_diffrn_orient_matrix_UB_23      0.0283404000
_diffrn_orient_matrix_UB_31      -0.0825145000
_diffrn_orient_matrix_UB_32      -0.0182458000
_diffrn_orient_matrix_UB_33      -0.0532993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_number_gt                3201
_reflns_number_total             3787
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.353
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_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     253
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0398
_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     
'calc w=1/[σ²(Fo²)+(0.0363P)²+0.4698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0985
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C13(H13), C22(H22), C15(H15), C4(H4), C20(H20), C8(H8), C5(H5),
 C9(H9), C21(H21), C11(H11), C19(H19), C16(H16), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O2 O 0.40646(16) 0.12502(9) 0.39024(8) 0.0204(2) Uani 1 d . . .
O1 O 0.65147(16) 0.53562(9) 0.21655(9) 0.0237(2) Uani 1 d . . .
N3 N 0.99151(19) 0.13913(11) 0.62288(10) 0.0190(3) Uani 1 d . . .
N1 N 0.1585(2) 0.64602(11) 0.02925(10) 0.0200(3) Uani 1 d . . .
N2 N 1.2238(2) 0.45156(11) 0.36313(11) 0.0227(3) Uani 1 d . . .
N4 N -0.2573(2) 0.00339(12) 0.12256(11) 0.0251(3) Uani 1 d . . .
C1 C 0.1151(2) 0.53718(12) 0.03235(11) 0.0171(3) Uani 1 d . . .
C12 C 0.9257(2) 0.04658(12) 0.51513(11) 0.0159(3) Uani 1 d . . .
C14 C 0.5978(2) 0.12379(13) 0.46298(12) 0.0169(3) Uani 1 d . . .
C7 C 0.8221(2) 0.40731(12) 0.29414(11) 0.0174(3) Uani 1 d . . .
C18 C 0.1413(2) 0.05057(12) 0.20575(11) 0.0170(3) Uani 1 d . . .
C2 C 0.2719(2) 0.49271(12) 0.09236(11) 0.0177(3) Uani 1 d . . .
H2 H 0.2352 0.4147 0.0914 0.021 Uiso 1 calc . . R
C13 C 0.7303(2) 0.03454(12) 0.43267(12) 0.0165(3) Uani 1 d . . .
H13 H 0.6887 -0.0330 0.3576 0.020 Uiso 1 calc . . R
C22 C 0.1595(2) 0.13564(13) 0.16177(12) 0.0196(3) Uani 1 d . . .
H22 H 0.3015 0.1801 0.1744 0.024 Uiso 1 calc . . R
C6 C 0.6124(2) 0.41865(13) 0.21967(12) 0.0192(3) Uani 1 d . . .
H6A H 0.5740 0.3499 0.1407 0.023 Uiso 1 calc . . R
H6B H 0.4869 0.4148 0.2521 0.023 Uiso 1 calc . . R
C17 C 0.3427(2) 0.02598(13) 0.27385(12) 0.0186(3) Uani 1 d . . .
H17A H 0.3076 -0.0547 0.2745 0.022 Uiso 1 calc . . R
H17B H 0.4662 0.0235 0.2389 0.022 Uiso 1 calc . . R
C15 C 0.6617(2) 0.22007(13) 0.57487(12) 0.0197(3) Uani 1 d . . .
H15 H 0.5736 0.2817 0.5987 0.024 Uiso 1 calc . . R
C4 C 0.5299(2) 0.67923(13) 0.15192(12) 0.0209(3) Uani 1 d . . .
H4 H 0.6719 0.7315 0.1933 0.025 Uiso 1 calc . . R
C20 C -0.2344(2) 0.08691(13) 0.08226(12) 0.0219(3) Uani 1 d . . .
H20 H -0.3652 0.1003 0.0394 0.026 Uiso 1 calc . . R
C8 C 1.0306(2) 0.45863(13) 0.29887(12) 0.0196(3) Uani 1 d . . .
H8 H 1.0371 0.5016 0.2537 0.024 Uiso 1 calc . . R
C5 C 0.3645(2) 0.71346(13) 0.08853(12) 0.0208(3) Uani 1 d . . .
H5 H 0.3986 0.7902 0.0867 0.025 Uiso 1 calc . . R
C9 C 1.2111(2) 0.38880(13) 0.42440(13) 0.0223(3) Uani 1 d . . .
H9 H 1.3460 0.3826 0.4704 0.027 Uiso 1 calc . . R
C21 C -0.0314(2) 0.15477(13) 0.09937(12) 0.0204(3) Uani 1 d . . .
H21 H -0.0235 0.2130 0.0690 0.024 Uiso 1 calc . . R
C11 C 0.8138(2) 0.34283(13) 0.35908(12) 0.0208(3) Uani 1 d . . .
H11 H 0.6746 0.3065 0.3587 0.025 Uiso 1 calc . . R
C19 C -0.0695(2) -0.01283(14) 0.18334(12) 0.0219(3) Uani 1 d . . .
H19 H -0.0820 -0.0715 0.2128 0.026 Uiso 1 calc . . R
C3 C 0.4828(2) 0.56559(13) 0.15347(12) 0.0183(3) Uani 1 d . . .
C16 C 0.8577(2) 0.22256(13) 0.64979(12) 0.0206(3) Uani 1 d . . .
H16 H 0.9011 0.2881 0.7260 0.025 Uiso 1 calc . . R
C10 C 1.0117(2) 0.33232(13) 0.42440(12) 0.0224(3) Uani 1 d . . .
H10 H 1.0104 0.2873 0.4682 0.027 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C14 1.3610(15) . ?
O2 C17 1.4471(16) . ?
O1 C6 1.4384(16) . ?
O1 C3 1.3595(16) . ?
N3 C12 1.3429(18) . ?
N3 C16 1.3435(18) . ?
N1 C1 1.3453(17) . ?
N1 C5 1.3436(18) . ?
N2 C8 1.3424(18) . ?
N2 C9 1.3366(19) . ?
N4 C20 1.3404(19) . ?
N4 C19 1.3423(18) . ?
C1 C1 1.496(3) 2_565 ?
C1 C2 1.3997(19) . ?
C12 C12 1.497(3) 2_756 ?
C12 C13 1.3947(18) . ?
C14 C13 1.3908(19) . ?
C14 C15 1.3955(19) . ?
C7 C6 1.5047(18) . ?
C7 C8 1.3866(19) . ?
C7 C11 1.3915(19) . ?
C18 C22 1.3900(19) . ?
C18 C17 1.5001(18) . ?
C18 C19 1.3845(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.3909(19) . ?
C13 H13 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.3834(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.3812(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(2) . ?
C4 C3 1.3955(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(2) . ?
C8 H8 0.9500 . ?
C5 H5 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.386(2) . ?
C21 H21 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.387(2) . ?
C19 H19 0.9500 . ?
C16 H16 0.9500 . ?
C10 H10 0.9500 . ?

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
C14 O2 C17 116.17(10) . . ?
C3 O1 C6 118.12(11) . . ?
C12 N3 C16 116.57(11) . . ?
C5 N1 C1 116.50(12) . . ?
C9 N2 C8 116.90(13) . . ?
C20 N4 C19 116.57(12) . . ?
N1 C1 C1 116.53(15) . 2_565 ?
N1 C1 C2 123.47(12) . . ?
C2 C1 C1 120.00(15) . 2_565 ?
N3 C12 C12 116.70(14) . 2_756 ?
N3 C12 C13 123.45(12) . . ?
C13 C12 C12 119.84(15) . 2_756 ?
O2 C14 C13 124.47(12) . . ?
O2 C14 C15 116.41(12) . . ?
C13 C14 C15 119.13(12) . . ?
C8 C7 C6 121.28(12) . . ?
C8 C7 C11 117.59(13) . . ?
C11 C7 C6 121.12(12) . . ?
C22 C18 C17 121.51(12) . . ?
C19 C18 C22 117.89(12) . . ?
C19 C18 C17 120.59(12) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.36(13) . . ?
C3 C2 H2 120.8 . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.40(12) . . ?
C14 C13 H13 120.8 . . ?
C18 C22 H22 120.4 . . ?
C21 C22 C18 119.24(13) . . ?
C21 C22 H22 120.4 . . ?
O1 C6 C7 107.92(11) . . ?
O1 C6 H6A 110.1 . . ?
O1 C6 H6B 110.1 . . ?
C7 C6 H6A 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
O2 C17 C18 107.67(11) . . ?
O2 C17 H17A 110.2 . . ?
O2 C17 H17B 110.2 . . ?
C18 C17 H17A 110.2 . . ?
C18 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C14 C15 H15 121.2 . . ?
C16 C15 C14 117.62(13) . . ?
C16 C15 H15 121.2 . . ?
C5 C4 H4 120.9 . . ?
C5 C4 C3 118.11(13) . . ?
C3 C4 H4 120.9 . . ?
N4 C20 H20 118.1 . . ?
N4 C20 C21 123.89(13) . . ?
C21 C20 H20 118.1 . . ?
N2 C8 C7 124.26(13) . . ?
N2 C8 H8 117.9 . . ?
C7 C8 H8 117.9 . . ?
N1 C5 C4 124.67(13) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
N2 C9 H9 118.3 . . ?
N2 C9 C10 123.49(13) . . ?
C10 C9 H9 118.3 . . ?
C22 C21 C20 118.29(13) . . ?
C22 C21 H21 120.9 . . ?
C20 C21 H21 120.9 . . ?
C7 C11 H11 120.4 . . ?
C10 C11 C7 119.12(13) . . ?
C10 C11 H11 120.4 . . ?
N4 C19 C18 124.11(13) . . ?
N4 C19 H19 117.9 . . ?
C18 C19 H19 117.9 . . ?
O1 C3 C2 125.18(12) . . ?
O1 C3 C4 115.95(12) . . ?
C2 C3 C4 118.87(12) . . ?
N3 C16 C15 124.82(13) . . ?
N3 C16 H16 117.6 . . ?
C15 C16 H16 117.6 . . ?
C9 C10 C11 118.62(13) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?

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
O2 C14 C13 C12 178.24(12) . . . . ?
O2 C14 C15 C16 -178.67(12) . . . . ?
N3 C12 C13 C14 0.8(2) . . . . ?
N1 C1 C2 C3 1.0(2) . . . . ?
N2 C9 C10 C11 -1.1(2) . . . . ?
N4 C20 C21 C22 -0.1(2) . . . . ?
C1 N1 C5 C4 -0.6(2) . . . . ?
C1 C1 C2 C3 -178.69(15) 2_565 . . . ?
C1 C2 C3 O1 179.35(13) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C12 N3 C16 C15 -0.7(2) . . . . ?
C12 C12 C13 C14 -178.95(15) 2_756 . . . ?
C14 O2 C17 C18 -175.03(11) . . . . ?
C14 C15 C16 N3 0.0(2) . . . . ?
C7 C11 C10 C9 1.3(2) . . . . ?
C18 C22 C21 C20 -0.6(2) . . . . ?
C13 C14 C15 C16 1.1(2) . . . . ?
C22 C18 C17 O2 79.68(16) . . . . ?
C22 C18 C19 N4 -0.5(2) . . . . ?
C6 O1 C3 C2 1.1(2) . . . . ?
C6 O1 C3 C4 -179.17(12) . . . . ?
C6 C7 C8 N2 -179.79(13) . . . . ?
C6 C7 C11 C10 178.51(13) . . . . ?
C17 O2 C14 C13 -0.58(19) . . . . ?
C17 O2 C14 C15 179.12(12) . . . . ?
C17 C18 C22 C21 179.90(12) . . . . ?
C17 C18 C19 N4 -179.57(13) . . . . ?
C15 C14 C13 C12 -1.45(19) . . . . ?
C20 N4 C19 C18 -0.1(2) . . . . ?
C8 N2 C9 C10 -0.1(2) . . . . ?
C8 C7 C6 O1 -32.84(18) . . . . ?
C8 C7 C11 C10 -0.3(2) . . . . ?
C5 N1 C1 C1 179.22(14) . . . 2_565 ?
C5 N1 C1 C2 -0.5(2) . . . . ?
C5 C4 C3 O1 179.63(13) . . . . ?
C5 C4 C3 C2 -0.6(2) . . . . ?
C9 N2 C8 C7 1.2(2) . . . . ?
C11 C7 C6 O1 148.41(13) . . . . ?
C11 C7 C8 N2 -1.0(2) . . . . ?
C19 N4 C20 C21 0.4(2) . . . . ?
C19 C18 C22 C21 0.9(2) . . . . ?
C19 C18 C17 O2 -101.30(15) . . . . ?
C3 O1 C6 C7 179.88(12) . . . . ?
C3 C4 C5 N1 1.2(2) . . . . ?
C16 N3 C12 C12 -179.98(14) . . . 2_756 ?
C16 N3 C12 C13 0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.148
_oxdiff_exptl_absorpt_empirical_full_min 0.921
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1500639'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2017-02-02 downloaded from the CCDC.
;
_audit_creation_date             2016-08-06
_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         'C22 H18 N4 O2'
_chemical_formula_sum            'C22 H18 N4 O2'
_chemical_formula_weight         370.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H20 N4 O2'
_chemical_oxdiff_usercomment     'Clear, Colerless, block, 0.1 0.1 0.08'
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                   3.84500(7)
_cell_length_b                   20.0524(4)
_cell_length_c                   11.01623(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.6073(16)
_cell_angle_gamma                90
_cell_volume                     847.69(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5212
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.6600
_cell_measurement_theta_min      4.3900
_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  0.85470
_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_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8117
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.787
_diffrn_reflns_theta_min         4.410
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -70.00  -42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   57.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega -110.00  -17.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -57.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega  -63.00   28.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega  -63.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   57.0000  120.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   12.00   38.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513  -99.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  110.00  169.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
  7 omega   96.00  126.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega  117.00  164.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
  9 omega   81.00  115.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   89.00  115.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00  100.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 62

#__ type_ start__ end____ width___ exp.time_
 12 omega  108.00  139.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
 13 omega   31.00   99.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 68

#__ type_ start__ end____ width___ exp.time_
 14 omega   74.00  101.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   42.00   78.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega   64.00  139.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
 17 omega   41.00  140.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
 18 omega   52.00  108.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
 19 omega   92.00  153.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
 20 omega   40.00   96.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
 21 omega   74.00  109.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
 22 omega   43.00   71.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 23 omega  102.00  137.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -60.0000 35

#__ type_ start__ end____ width___ exp.time_
 24 omega  102.00  127.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   34.00   86.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000  150.0000 52

#__ type_ start__ end____ width___ exp.time_
 26 omega   93.00  118.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega  106.00  134.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
 28 omega   53.00   78.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega  103.00  136.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 30 omega   54.00  124.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
 31 omega  110.00  138.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
 32 omega   49.00   92.00   1.0000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000 -120.0000 43
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1141239000
_diffrn_orient_matrix_UB_12      -0.0092817000
_diffrn_orient_matrix_UB_13      -0.1305112000
_diffrn_orient_matrix_UB_21      -0.0419126000
_diffrn_orient_matrix_UB_22      -0.0760616000
_diffrn_orient_matrix_UB_23      0.0122547000
_diffrn_orient_matrix_UB_31      -0.3825596000
_diffrn_orient_matrix_UB_32      0.0055867000
_diffrn_orient_matrix_UB_33      -0.0495440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1672
_reflns_number_total             1781
_reflns_odcompleteness_completeness 96.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.2573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0906
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C10(H10), C2(H2), C3(H3), C9(H9), C8(H8)
;
_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 0.1780(2) 0.58557(4) 0.85488(7) 0.01917(19) Uani 1 1 d . . . . .
N1 N -0.1776(2) 0.44170(4) 0.60461(8) 0.0191(2) Uani 1 1 d . . . . .
N2 N 0.7452(3) 0.76854(5) 1.10683(9) 0.0230(2) Uani 1 1 d . . . . .
C11 C 0.6119(3) 0.65966(5) 1.02324(9) 0.0189(2) Uani 1 1 d . . . . .
H11 H 0.6226 0.6136 1.0331 0.023 Uiso 1 1 calc R . . . .
C5 C 0.0964(3) 0.54853(5) 0.64445(9) 0.0175(2) Uani 1 1 d . . . . .
H5 H 0.1951 0.5869 0.6140 0.021 Uiso 1 1 calc R . . . .
C7 C 0.4616(3) 0.68754(5) 0.91678(9) 0.0165(2) Uani 1 1 d . . . . .
C4 C 0.0632(3) 0.54078(5) 0.76869(9) 0.0172(2) Uani 1 1 d . . . . .
C6 C 0.3268(3) 0.64617(5) 0.81056(9) 0.0175(2) Uani 1 1 d . . . . .
H6A H 0.1511 0.6709 0.7622 0.021 Uiso 1 1 calc R . . . .
H6B H 0.5155 0.6356 0.7594 0.021 Uiso 1 1 calc R . . . .
C10 C 0.7454(3) 0.70184(6) 1.11435(10) 0.0208(2) Uani 1 1 d . . . . .
H10 H 0.8416 0.6825 1.1855 0.025 Uiso 1 1 calc R . . . .
C2 C -0.2148(3) 0.43682(5) 0.72444(10) 0.0200(2) Uani 1 1 d . . . . .
H2 H -0.3269 0.3992 0.7521 0.024 Uiso 1 1 calc R . . . .
C1 C -0.0221(3) 0.49728(5) 0.56669(9) 0.0169(2) Uani 1 1 d . . . . .
C3 C -0.0991(3) 0.48353(5) 0.80996(10) 0.0189(2) Uani 1 1 d . . . . .
H3 H -0.1284 0.4771 0.8923 0.023 Uiso 1 1 calc R . . . .
C9 C 0.6019(3) 0.79469(6) 1.00372(10) 0.0233(2) Uani 1 1 d . . . . .
H9 H 0.6001 0.8408 0.9955 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4556(3) 0.75668(5) 0.90822(10) 0.0201(2) Uani 1 1 d . . . . .
H8 H 0.3545 0.7773 0.8391 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.3603(12) . ?
O1 C6 1.4413(12) . ?
N1 C2 1.3403(14) . ?
N1 C1 1.3437(14) . ?
N2 C10 1.3402(15) . ?
N2 C9 1.3380(15) . ?
C11 C7 1.3916(14) . ?
C11 C10 1.3861(15) . ?
C5 C4 1.3913(15) . ?
C5 C1 1.3959(14) . ?
C7 C6 1.5000(14) . ?
C7 C8 1.3898(15) . ?
C4 C3 1.3962(15) . ?
C2 C3 1.3821(15) . ?
C1 C1 1.494(2) 3_566 ?
C9 C8 1.3891(15) . ?

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 C6 116.01(8) . . ?
C2 N1 C1 116.35(9) . . ?
C9 N2 C10 116.24(9) . . ?
C10 C11 C7 118.70(10) . . ?
C4 C5 C1 118.35(9) . . ?
C11 C7 C6 122.68(9) . . ?
C8 C7 C11 117.53(10) . . ?
C8 C7 C6 119.70(9) . . ?
O1 C4 C5 124.54(9) . . ?
O1 C4 C3 116.59(9) . . ?
C5 C4 C3 118.86(9) . . ?
O1 C6 C7 109.09(8) . . ?
N2 C10 C11 124.44(10) . . ?
N1 C2 C3 124.90(10) . . ?
N1 C1 C5 123.66(9) . . ?
N1 C1 C1 116.53(11) . 3_566 ?
C5 C1 C1 119.81(12) . 3_566 ?
C2 C3 C4 117.81(10) . . ?
N2 C9 C8 123.61(10) . . ?
C9 C8 C7 119.46(10) . . ?

_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_2
_database_code_depnum_ccdc_archive 'CCDC 1500637'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2017-02-02 downloaded from the CCDC.
;
_audit_creation_date             2016-07-19
_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         'C22 H18 N4 O2'
_chemical_formula_sum            'C22 H18 N4 O2'
_chemical_formula_weight         370.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H18 O2 N4'
_chemical_oxdiff_usercomment     'Colorless, Block, 0.07 0.1 0.2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   3.8257(2)
_cell_length_b                   9.9197(7)
_cell_length_c                   11.9058(5)
_cell_angle_alpha                77.653(5)
_cell_angle_beta                 89.013(4)
_cell_angle_gamma                80.097(6)
_cell_volume                     434.70(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2650
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.9830
_cell_measurement_theta_min      3.5020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             194
_exptl_crystal_size_max          0.2338
_exptl_crystal_size_mid          0.1216
_exptl_crystal_size_min          0.0601
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5155
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         3.504
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.0053
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   10.00   51.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4518   77.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   -6.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4518   77.0000 -120.0000 48

#__ type_ start__ end____ width___ exp.time_
  3 omega  -58.00   48.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4518   77.0000  -60.0000 106

#__ type_ start__ end____ width___ exp.time_
  4 omega  -59.00   50.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4518   77.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
  5 omega   24.00   51.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4518   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00   46.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.4518   77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega  -11.00   98.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       24.3893   77.0000 -180.0000 109

#__ type_ start__ end____ width___ exp.time_
  8 omega   -9.00   91.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       24.3893   77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
  9 omega  -11.00   96.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       24.3893   77.0000   60.0000 107
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0752478000
_diffrn_orient_matrix_UB_12      0.0591779000
_diffrn_orient_matrix_UB_13      0.0046504000
_diffrn_orient_matrix_UB_21      0.0400399000
_diffrn_orient_matrix_UB_22      0.0111233000
_diffrn_orient_matrix_UB_23      -0.0593150000
_diffrn_orient_matrix_UB_31      -0.1678452000
_diffrn_orient_matrix_UB_32      0.0435438000
_diffrn_orient_matrix_UB_33      -0.0134548000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1502
_reflns_number_total             1703
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.057
_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)+(0.0442P)²+0.1734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C3(H3), C9(H9), C2(H2), C10(H10), C8(H8)
;
_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 0.4681(2) 0.19150(9) 0.64975(7) 0.0205(2) Uani 1 1 d . . . . .
N2 N 0.3821(3) 0.39219(11) 0.35871(9) 0.0183(3) Uani 1 1 d . . . . .
N1 N 0.2293(3) 0.17061(11) 0.99404(9) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.3363(3) 0.31287(13) 0.56273(10) 0.0155(3) Uani 1 1 d . . . . .
H6A H 0.4220 0.3959 0.5782 0.019 Uiso 1 1 calc R . . . .
H6B H 0.0736 0.3313 0.5618 0.019 Uiso 1 1 calc R . . . .
C5 C 0.5090(3) 0.07098(13) 0.84110(10) 0.0161(3) Uani 1 1 d . . . . .
H5 H 0.6512 -0.0061 0.8176 0.019 Uiso 1 1 calc R . . . .
C1 C 0.4305(3) 0.06417(12) 0.95593(10) 0.0154(3) Uani 1 1 d . . . . .
C7 C 0.4696(3) 0.28459(13) 0.44879(10) 0.0144(3) Uani 1 1 d . . . . .
C4 C 0.3770(3) 0.19217(13) 0.76070(10) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.6661(3) 0.15687(13) 0.43812(11) 0.0176(3) Uani 1 1 d . . . . .
H11 H 0.7241 0.0831 0.5039 0.021 Uiso 1 1 calc R . . . .
C3 C 0.1679(3) 0.30318(13) 0.79724(10) 0.0174(3) Uani 1 1 d . . . . .
H3 H 0.0717 0.3873 0.7447 0.021 Uiso 1 1 calc R . . . .
C9 C 0.6885(3) 0.24792(14) 0.23616(11) 0.0203(3) Uani 1 1 d . . . . .
H9 H 0.7601 0.2386 0.1610 0.024 Uiso 1 1 calc R . . . .
C2 C 0.1063(3) 0.28503(14) 0.91457(11) 0.0200(3) Uani 1 1 d . . . . .
H2 H -0.0355 0.3606 0.9403 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7765(3) 0.13836(14) 0.33012(11) 0.0196(3) Uani 1 1 d . . . . .
H10 H 0.9107 0.0517 0.3208 0.023 Uiso 1 1 calc R . . . .
C8 C 0.4930(4) 0.37140(14) 0.25533(11) 0.0208(3) Uani 1 1 d . . . . .
H8 H 0.4329 0.4467 0.1908 0.025 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.4328(14) . ?
O1 C4 1.3615(14) . ?
N2 C7 1.3422(15) . ?
N2 C8 1.3408(16) . ?
N1 C1 1.3514(16) . ?
N1 C2 1.3331(16) . ?
C6 C7 1.5062(16) . ?
C5 C1 1.3847(17) . ?
C5 C4 1.3900(17) . ?
C1 C1 1.490(2) 2_657 ?
C7 C11 1.3871(18) . ?
C4 C3 1.3899(18) . ?
C11 C10 1.3860(17) . ?
C3 C2 1.3910(17) . ?
C9 C10 1.3831(18) . ?
C9 C8 1.3823(19) . ?

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 C6 118.28(9) . . ?
C8 N2 C7 116.87(11) . . ?
C2 N1 C1 116.39(10) . . ?
O1 C6 C7 107.69(9) . . ?
C1 C5 C4 119.10(11) . . ?
N1 C1 C5 122.90(11) . . ?
N1 C1 C1 116.83(13) . 2_657 ?
C5 C1 C1 120.27(13) . 2_657 ?
N2 C7 C6 114.79(10) . . ?
N2 C7 C11 122.79(11) . . ?
C11 C7 C6 122.42(11) . . ?
O1 C4 C5 115.70(11) . . ?
O1 C4 C3 124.98(11) . . ?
C3 C4 C5 119.33(11) . . ?
C10 C11 C7 119.05(11) . . ?
C4 C3 C2 116.71(11) . . ?
C8 C9 C10 117.75(11) . . ?
N1 C2 C3 125.57(12) . . ?
C9 C10 C11 119.04(12) . . ?
N2 C8 C9 124.50(12) . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -1 16 0.0541 0.0000 -1.0000 16.0000 0.0152 -0.9602 -0.2588
0 1 -16 0.0582 -0.0000 1.0000 -16.0000 -0.0152 0.9602 0.2588
4 -5 5 0.1038 4.0000 -5.0000 5.0000 0.0284 -0.1920 -0.9564
-4 6 1 0.0897 -4.0000 6.0000 1.0000 0.0587 -0.1527 0.9192
-5 -9 -5 0.0381 -5.0000 -9.0000 -5.0000 -0.9321 -0.0037 0.5146
5 9 5 0.0220 5.0000 9.0000 5.0000 0.9321 0.0037 -0.5146
-1 -14 -3 0.1063 -1.0000 -14.0000 -3.0000 -0.9177 -0.0178 -0.4014
0 14 2 0.0794 -0.0000 14.0000 2.0000 0.8378 0.0371 0.5827
4 -7 -8 0.1105 4.0000 -7.0000 -8.0000 -0.1505 0.5568 -0.8685


_ins_header                      
;
TITL 2 in P-1 
REM P-1 (#2 in standard setting)
CELL 0.71073   3.825671   9.919659  11.905768  77.6527  89.0131  80.0974
ZERR    1.00   0.000230   0.000703   0.000531   0.0048   0.0042   0.0055
LATT  1
SFAC C H N O
UNIT 22.00 18.00 4.00 2.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
