# Electronic Supplementary Material (ESI) for ChemComm.
# 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_160417_hq_2_chn
_database_code_depnum_ccdc_archive 'CCDC 1486571'
_audit_update_record             
;
2016-06-18 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_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         'C13 H10 N4'
_chemical_formula_sum            'C13 H10 N4'
_chemical_formula_weight         222.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H 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'

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

_cell_length_a                   13.2896(8)
_cell_length_b                   5.5930(3)
_cell_length_c                   16.4363(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.323(6)
_cell_angle_gamma                90.00
_cell_volume                     1159.75(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2298
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.7280
_cell_measurement_theta_min      5.1470
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74282
_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_crystal_colour            ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6340
_diffrn_reflns_theta_full        66.55
_diffrn_reflns_theta_max         66.55
_diffrn_reflns_theta_min         5.16
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   16.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3677   37.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3677  -57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3677  -37.0000 -180.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega   18.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3677 -125.0000 -150.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3677  106.0000   -6.6920 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   91.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00  116.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
  8 omega   91.00  176.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00  109.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   98.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00  109.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   90.00  175.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   91.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 15 omega   16.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3677   37.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 16 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3677   57.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3677   57.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
 18 omega  -34.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.3677  -37.0000  -90.0000 89

#__ type_ start__ end____ width___ exp.time_
 19 omega   90.00  175.00   1.0000    3.0550
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0677702000
_diffrn_orient_matrix_UB_12      -0.2265632000
_diffrn_orient_matrix_UB_13      -0.0056137000
_diffrn_orient_matrix_UB_21      -0.0968418000
_diffrn_orient_matrix_UB_22      0.1564870000
_diffrn_orient_matrix_UB_23      -0.0039812000
_diffrn_orient_matrix_UB_31      -0.0306143000
_diffrn_orient_matrix_UB_32      0.0066778000
_diffrn_orient_matrix_UB_33      -0.0984854000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1688
_reflns_number_total             2050
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.132
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0036(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0681P)²+0.0966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1200
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C4(H4), C13(H13), C10(H10), C3(H3A), C11(H11), C1(H1),
 C12(H12), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N3 N 0.59365(10) 0.2651(2) 0.38241(7) 0.0558(3) Uani 1 d . . .
H3 H 0.5601 0.3633 0.4049 0.067 Uiso 1 calc . . R
N1 N 0.72278(11) -0.1532(2) 0.63913(8) 0.0630(4) Uani 1 d . . .
N2 N 0.64849(9) 0.0869(2) 0.42819(7) 0.0517(3) Uani 1 d . . .
C8 C 0.59064(10) 0.2926(2) 0.29683(8) 0.0504(3) Uani 1 d . . .
C5 C 0.71456(10) -0.1465(2) 0.55596(8) 0.0496(3) Uani 1 d . . .
C6 C 0.65208(10) 0.0531(2) 0.50702(8) 0.0487(3) Uani 1 d . . .
C9 C 0.63779(12) 0.1273(3) 0.25713(10) 0.0602(4) Uani 1 d . . .
H9 H 0.6735 -0.0039 0.2875 0.072 Uiso 1 calc . . R
C4 C 0.76192(11) -0.3143(3) 0.51738(10) 0.0575(4) Uani 1 d . . .
H4 H 0.7538 -0.3057 0.4592 0.069 Uiso 1 calc . . R
C13 C 0.53858(13) 0.4875(3) 0.25113(10) 0.0638(4) Uani 1 d . . .
H13 H 0.5073 0.5997 0.2773 0.077 Uiso 1 calc . . R
N4 N 0.54691(11) 0.3287(3) 0.57728(9) 0.0693(4) Uani 1 d . . .
C10 C 0.63136(14) 0.1587(3) 0.17267(10) 0.0678(4) Uani 1 d . . .
H10 H 0.6625 0.0472 0.1461 0.081 Uiso 1 calc . . R
C7 C 0.59544(11) 0.2036(3) 0.54938(8) 0.0530(4) Uani 1 d . . .
C3 C 0.82104(12) -0.4931(3) 0.56729(12) 0.0677(4) Uani 1 d . . .
H3A H 0.8541 -0.6073 0.5433 0.081 Uiso 1 calc . . R
C11 C 0.57955(13) 0.3526(3) 0.12682(10) 0.0695(5) Uani 1 d . . .
H11 H 0.5760 0.3731 0.0698 0.083 Uiso 1 calc . . R
C1 C 0.78041(15) -0.3307(3) 0.68556(10) 0.0738(5) Uani 1 d . . .
H1 H 0.7866 -0.3386 0.7435 0.089 Uiso 1 calc . . R
C12 C 0.53316(15) 0.5154(3) 0.16643(11) 0.0722(5) Uani 1 d . . .
H12 H 0.4976 0.6463 0.1357 0.087 Uiso 1 calc . . R
C2 C 0.83091(13) -0.5017(3) 0.65291(12) 0.0735(5) Uani 1 d . . .
H2 H 0.8709 -0.6207 0.6879 0.088 Uiso 1 calc . . R

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N3 0.0632(7) 0.0554(7) 0.0493(6) -0.0002(5) 0.0181(5) 0.0086(5)
N1 0.0783(8) 0.0600(7) 0.0477(6) 0.0003(5) 0.0154(6) 0.0000(6)
N2 0.0555(6) 0.0500(6) 0.0482(6) -0.0008(5) 0.0146(5) -0.0008(5)
C8 0.0489(7) 0.0516(7) 0.0494(7) 0.0004(6) 0.0135(5) -0.0030(6)
C5 0.0502(7) 0.0490(7) 0.0480(7) -0.0035(5) 0.0133(6) -0.0087(5)
C6 0.0503(7) 0.0500(7) 0.0457(7) -0.0050(5) 0.0150(5) -0.0058(5)
C9 0.0662(8) 0.0573(8) 0.0593(8) 0.0087(7) 0.0226(7) 0.0101(7)
C4 0.0563(8) 0.0579(8) 0.0608(8) -0.0027(7) 0.0218(6) -0.0040(6)
C13 0.0719(9) 0.0589(9) 0.0617(9) 0.0044(7) 0.0225(7) 0.0129(7)
N4 0.0710(8) 0.0752(9) 0.0653(8) -0.0032(7) 0.0267(7) 0.0081(7)
C10 0.0771(10) 0.0720(10) 0.0615(9) 0.0048(7) 0.0323(8) 0.0123(8)
C7 0.0538(7) 0.0562(8) 0.0481(7) -0.0002(6) 0.0147(6) -0.0044(6)
C3 0.0564(8) 0.0567(9) 0.0890(11) -0.0014(8) 0.0214(8) 0.0009(7)
C11 0.0733(10) 0.0847(11) 0.0536(8) 0.0130(8) 0.0246(7) 0.0069(8)
C1 0.0870(11) 0.0716(11) 0.0535(8) 0.0102(8) 0.0087(8) -0.0026(9)
C12 0.0799(10) 0.0704(10) 0.0658(9) 0.0193(8) 0.0220(8) 0.0162(8)
C2 0.0630(9) 0.0628(9) 0.0815(11) 0.0150(8) 0.0039(8) 0.0008(7)

_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
N3 H3 0.8600 . ?
N3 N2 1.3214(16) . ?
N3 C8 1.4031(17) . ?
N1 C5 1.3373(17) . ?
N1 C1 1.337(2) . ?
N2 C6 1.2953(17) . ?
C8 C9 1.389(2) . ?
C8 C13 1.380(2) . ?
C5 C6 1.4708(18) . ?
C5 C4 1.3892(19) . ?
C6 C7 1.4455(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.373(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.380(2) . ?
N4 C7 1.1409(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(2) . ?
C3 H3A 0.9300 . ?
C3 C2 1.372(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(3) . ?
C12 H12 0.9300 . ?
C2 H2 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
N2 N3 H3 120.3 . . ?
N2 N3 C8 119.37(11) . . ?
C8 N3 H3 120.3 . . ?
C1 N1 C5 116.89(14) . . ?
C6 N2 N3 121.33(12) . . ?
C9 C8 N3 121.54(13) . . ?
C13 C8 N3 118.93(12) . . ?
C13 C8 C9 119.53(13) . . ?
N1 C5 C6 115.52(12) . . ?
N1 C5 C4 123.00(13) . . ?
C4 C5 C6 121.48(12) . . ?
N2 C6 C5 119.65(12) . . ?
N2 C6 C7 122.40(12) . . ?
C7 C6 C5 117.95(11) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.68(14) . . ?
C10 C9 H9 120.2 . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.40(14) . . ?
C3 C4 H4 120.8 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.77(14) . . ?
C12 C13 H13 120.1 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.03(14) . . ?
C11 C10 H10 119.5 . . ?
N4 C7 C6 175.18(15) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 C4 119.37(15) . . ?
C2 C3 H3A 120.3 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.02(14) . . ?
C12 C11 H11 120.5 . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C2 123.90(15) . . ?
C2 C1 H1 118.0 . . ?
C13 C12 H12 119.5 . . ?
C11 C12 C13 120.97(15) . . ?
C11 C12 H12 119.5 . . ?
C3 C2 H2 120.8 . . ?
C1 C2 C3 118.44(15) . . ?
C1 C2 H2 120.8 . . ?

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 N2 C6 C5 -179.64(11) . . . . ?
N3 N2 C6 C7 1.2(2) . . . . ?
N3 C8 C9 C10 178.83(14) . . . . ?
N3 C8 C13 C12 -178.85(14) . . . . ?
N1 C5 C6 N2 173.34(12) . . . . ?
N1 C5 C6 C7 -7.42(17) . . . . ?
N1 C5 C4 C3 -0.9(2) . . . . ?
N1 C1 C2 C3 -0.8(3) . . . . ?
N2 N3 C8 C9 4.6(2) . . . . ?
N2 N3 C8 C13 -176.08(13) . . . . ?
N2 C6 C7 N4 12.9(19) . . . . ?
C8 N3 N2 C6 -179.00(12) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C8 C13 C12 C11 -0.5(3) . . . . ?
C5 N1 C1 C2 0.4(2) . . . . ?
C5 C6 C7 N4 -166.3(18) . . . . ?
C5 C4 C3 C2 0.4(2) . . . . ?
C6 C5 C4 C3 178.61(12) . . . . ?
C9 C8 C13 C12 0.5(2) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C4 C5 C6 N2 -6.23(19) . . . . ?
C4 C5 C6 C7 173.02(12) . . . . ?
C4 C3 C2 C1 0.4(2) . . . . ?
C13 C8 C9 C10 -0.5(2) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C1 N1 C5 C6 -179.05(13) . . . . ?
C1 N1 C5 C4 0.5(2) . . . . ?

_olex2_date_sample_data_collection 2009-06-15
_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_160510_haoq_1
_database_code_depnum_ccdc_archive 'CCDC 1486572'
_audit_update_record             
;
2016-06-18 deposited with the CCDC.
2017-10-23 downloaded from the CCDC.
;
_audit_creation_date             2016-05-11
_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         'C13 H10 N4'
_chemical_formula_sum            'C13 H10 N4'
_chemical_formula_weight         222.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y+1/2, z'
3 'x+1/2, -y, -z+1/2'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y-1/2, -z'
7 '-x-1/2, y, z-1/2'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   22.881(2)
_cell_length_b                   15.2104(8)
_cell_length_c                   7.5406(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2624.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1376
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4920
_cell_measurement_theta_min      4.0950
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86686
_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_crystal_colour            ?
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11874
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.50
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   55.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569  -99.0000  150.0000 160

#__ type_ start__ end____ width___ exp.time_
  2 omega  -53.00   85.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569    0.0000    0.0000 276

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00    8.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       15.8569 -108.0000  -35.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0089280000
_diffrn_orient_matrix_UB_12      0.0059976000
_diffrn_orient_matrix_UB_13      0.0892824000
_diffrn_orient_matrix_UB_21      0.0276425000
_diffrn_orient_matrix_UB_22      0.0184836000
_diffrn_orient_matrix_UB_23      0.0205629000
_diffrn_orient_matrix_UB_31      -0.0108023000
_diffrn_orient_matrix_UB_32      0.0423661000
_diffrn_orient_matrix_UB_33      -0.0216081000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1352
_reflns_number_total             2663
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2663
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      0.993
_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)+(0.0981P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.2073
_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 N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C13(H13), C2(H2), C4(H4), C9(H9), C10(H10), C3(H3A), C11(H11), C1(H1),
  C12(H12)
;
_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
N2 N 0.05871(9) 0.25700(12) 0.3448(3) 0.0616(6) Uani 1 d . . .
N3 N 0.10865(9) 0.25842(12) 0.4331(3) 0.0622(6) Uani 1 d . . .
H3 H 0.1233 0.3078 0.4664 0.075 Uiso 1 calc . . R
N1 N 0.10104(10) 0.43310(12) 0.4358(3) 0.0699(6) Uani 1 d . . .
C5 C 0.05288(12) 0.42238(14) 0.3345(3) 0.0602(7) Uani 1 d . . .
C8 C 0.13784(11) 0.17992(14) 0.4728(3) 0.0583(6) Uani 1 d . . .
C6 C 0.03326(11) 0.33165(14) 0.3017(3) 0.0607(7) Uani 1 d . . .
C13 C 0.18589(12) 0.18396(17) 0.5846(4) 0.0726(8) Uani 1 d . . .
H13 H 0.1978 0.2378 0.6305 0.087 Uiso 1 calc . . R
C2 C 0.09204(15) 0.58874(16) 0.3976(4) 0.0823(9) Uani 1 d . . .
H2 H 0.1063 0.6447 0.4216 0.099 Uiso 1 calc . . R
C7 C -0.02031(14) 0.32013(16) 0.2078(4) 0.0735(8) Uani 1 d . . .
C4 C 0.02320(12) 0.49360(15) 0.2613(4) 0.0705(8) Uani 1 d . . .
H4 H -0.0098 0.4846 0.1914 0.085 Uiso 1 calc . . R
C9 C 0.12080(12) 0.09924(15) 0.4057(4) 0.0705(7) Uani 1 d . . .
H9 H 0.0890 0.0955 0.3291 0.085 Uiso 1 calc . . R
C10 C 0.15078(13) 0.02479(15) 0.4524(4) 0.0797(8) Uani 1 d . . .
H10 H 0.1385 -0.0294 0.4089 0.096 Uiso 1 calc . . R
C3 C 0.04302(15) 0.57691(16) 0.2932(4) 0.0831(9) Uani 1 d . . .
H3A H 0.0237 0.6251 0.2452 0.100 Uiso 1 calc . . R
N4 N -0.06380(14) 0.31379(17) 0.1330(4) 0.1037(9) Uani 1 d . . .
C11 C 0.19868(14) 0.02872(18) 0.5623(4) 0.0838(9) Uani 1 d . . .
H11 H 0.2189 -0.0223 0.5915 0.101 Uiso 1 calc . . R
C1 C 0.11904(13) 0.51502(16) 0.4651(4) 0.0805(8) Uani 1 d . . .
H1 H 0.1519 0.5230 0.5357 0.097 Uiso 1 calc . . R
C12 C 0.21629(13) 0.1082(2) 0.6282(4) 0.0843(9) Uani 1 d . . .
H12 H 0.2487 0.1114 0.7024 0.101 Uiso 1 calc . . R

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0621(13) 0.0503(12) 0.0724(13) 0.0062(9) 0.0076(10) 0.0020(9)
N3 0.0596(13) 0.0463(11) 0.0806(14) 0.0041(9) 0.0044(11) 0.0000(9)
N1 0.0750(15) 0.0475(11) 0.0873(16) 0.0006(10) 0.0041(12) -0.0007(10)
C5 0.0674(16) 0.0508(14) 0.0624(15) 0.0011(11) 0.0144(13) 0.0067(11)
C8 0.0571(14) 0.0466(12) 0.0712(16) 0.0093(11) 0.0147(12) 0.0019(11)
C6 0.0654(16) 0.0477(14) 0.0691(16) 0.0023(11) 0.0074(12) 0.0060(11)
C13 0.0673(17) 0.0597(15) 0.091(2) -0.0013(13) 0.0033(15) -0.0013(13)
C2 0.096(2) 0.0435(15) 0.108(2) -0.0030(14) 0.0162(19) 0.0000(14)
C7 0.080(2) 0.0517(14) 0.089(2) -0.0016(13) -0.0071(16) 0.0067(13)
C4 0.0811(19) 0.0515(14) 0.0787(18) 0.0017(12) 0.0039(14) 0.0102(12)
C9 0.0737(18) 0.0514(14) 0.0863(19) 0.0029(12) -0.0005(14) 0.0002(12)
C10 0.086(2) 0.0475(14) 0.105(2) 0.0006(13) 0.0102(18) 0.0013(13)
C3 0.101(2) 0.0468(15) 0.102(2) 0.0063(14) 0.0068(19) 0.0122(14)
N4 0.105(2) 0.0722(16) 0.134(2) -0.0025(14) -0.0330(19) 0.0072(14)
C11 0.087(2) 0.0599(17) 0.105(2) 0.0140(15) 0.0105(18) 0.0146(15)
C1 0.0799(19) 0.0569(17) 0.105(2) -0.0041(14) 0.0005(16) -0.0049(13)
C12 0.0743(19) 0.0793(19) 0.099(2) 0.0107(16) -0.0047(16) 0.0139(16)

_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
N2 N3 1.323(2) . ?
N2 C6 1.317(3) . ?
N3 H3 0.8600 . ?
N3 C8 1.400(3) . ?
N1 C5 1.350(3) . ?
N1 C1 1.331(3) . ?
C5 C6 1.472(3) . ?
C5 C4 1.393(3) . ?
C8 C13 1.387(3) . ?
C8 C9 1.383(3) . ?
C6 C7 1.426(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.386(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C2 C1 1.378(3) . ?
C7 N4 1.148(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.367(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C3 H3A 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.368(4) . ?
C1 H1 0.9300 . ?
C12 H12 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
C6 N2 N3 119.48(19) . . ?
N2 N3 H3 119.8 . . ?
N2 N3 C8 120.36(19) . . ?
C8 N3 H3 119.8 . . ?
C1 N1 C5 117.4(2) . . ?
N1 C5 C6 117.2(2) . . ?
N1 C5 C4 121.9(2) . . ?
C4 C5 C6 120.9(3) . . ?
C13 C8 N3 118.0(2) . . ?
C9 C8 N3 123.0(2) . . ?
C9 C8 C13 119.0(2) . . ?
N2 C6 C5 129.2(2) . . ?
N2 C6 C7 113.4(2) . . ?
C7 C6 C5 117.4(2) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 117.9(2) . . ?
N4 C7 C6 177.7(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.4 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3A 120.3 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
N1 C1 C2 124.2(3) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?

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
N2 N3 C8 C13 -171.9(2) . . . . ?
N2 N3 C8 C9 8.0(3) . . . . ?
N2 C6 C7 N4 169(8) . . . . ?
N3 N2 C6 C5 1.4(4) . . . . ?
N3 N2 C6 C7 -179.7(2) . . . . ?
N3 C8 C13 C12 179.9(2) . . . . ?
N3 C8 C9 C10 -178.9(2) . . . . ?
N1 C5 C6 N2 -6.4(4) . . . . ?
N1 C5 C6 C7 174.8(2) . . . . ?
N1 C5 C4 C3 -0.4(4) . . . . ?
C5 N1 C1 C2 -0.6(4) . . . . ?
C5 C6 C7 N4 -12(8) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
C8 C13 C12 C11 -0.6(4) . . . . ?
C8 C9 C10 C11 -1.5(4) . . . . ?
C6 N2 N3 C8 -176.94(19) . . . . ?
C6 C5 C4 C3 -179.4(2) . . . . ?
C13 C8 C9 C10 1.0(4) . . . . ?
C4 C5 C6 N2 172.7(2) . . . . ?
C4 C5 C6 C7 -6.2(4) . . . . ?
C9 C8 C13 C12 0.0(4) . . . . ?
C9 C10 C11 C12 0.9(5) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C3 C2 C1 N1 0.2(4) . . . . ?
C1 N1 C5 C6 179.8(2) . . . . ?
C1 N1 C5 C4 0.7(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?

_olex2_date_sample_data_collection 2009-07-08
_olex2_submission_special_instructions 'No special instructions were received'
