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

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

data_wj002
_database_code_depnum_ccdc_archive 'CCDC 1032909'
_audit_update_record             
;
2014-11-05 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_audit_creation_date             2014-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H9 N3'
_chemical_formula_sum            'C12 H9 N3'
_chemical_formula_weight         195.22
_chemical_absolute_configuration ?
_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 0.0181 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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   8.2050(5)
_cell_length_b                   10.6112(6)
_cell_length_c                   10.8283(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     942.77(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1270
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      72.3820
_cell_measurement_theta_min      7.9570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2725
_diffrn_reflns_point_group_measured_fraction_full 0.738
_diffrn_reflns_point_group_measured_fraction_max 0.748
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.978
_diffrn_reflns_theta_min         6.821
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   30.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega   70.00  178.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 108

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   91.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega   48.00  105.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
  9 omega   48.00   78.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   75.00  133.00   1.0000    6.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1876144000
_diffrn_orient_matrix_UB_12      -0.0059976000
_diffrn_orient_matrix_UB_13      0.0026478000
_diffrn_orient_matrix_UB_21      0.0079415000
_diffrn_orient_matrix_UB_22      0.1449019000
_diffrn_orient_matrix_UB_23      0.0036777000
_diffrn_orient_matrix_UB_31      -0.0036998000
_diffrn_orient_matrix_UB_32      -0.0036993000
_diffrn_orient_matrix_UB_33      0.1422615000
_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'
_reflns_Friedel_coverage         0.411
_reflns_Friedel_fraction_full    0.458
_reflns_Friedel_fraction_max     0.465
_reflns_number_gt                1205
_reflns_number_total             1259
_reflns_odcompleteness_completeness 99.80
_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 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 337 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(7)
_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     136
_refine_ls_number_reflns         1259
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.069
_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)+(0.0820P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1197
_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), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.0914(3) -0.0652(2) -0.9685(3) 0.0363(5) Uani 1 1 d . . . . .
N2 N -0.1938(3) -0.2056(2) -1.0956(3) 0.0472(6) Uani 1 1 d . . . . .
N3 N -0.2478(4) -0.0895(3) -1.1349(3) 0.0493(6) Uani 1 1 d . . . . .
C1 C -0.0179(3) -0.2951(3) -0.9338(3) 0.0378(6) Uani 1 1 d . . . . .
C2 C 0.0425(4) -0.3938(3) -1.0056(3) 0.0446(7) Uani 1 1 d . . . . .
H2 H 0.0296 -0.3919 -1.0909 0.054 Uiso 1 1 calc R . . . .
C3 C 0.1210(4) -0.4940(3) -0.9510(4) 0.0521(8) Uani 1 1 d . . . . .
H3 H 0.1589 -0.5603 -0.9993 0.063 Uiso 1 1 calc R . . . .
C4 C 0.1438(4) -0.4963(3) -0.8242(4) 0.0559(9) Uani 1 1 d . . . . .
H4 H 0.1983 -0.5634 -0.7874 0.067 Uiso 1 1 calc R . . . .
C5 C 0.0849(5) -0.3983(3) -0.7527(3) 0.0517(8) Uani 1 1 d . . . . .
H5 H 0.1005 -0.3994 -0.6677 0.062 Uiso 1 1 calc R . . . .
C6 C 0.0026(4) -0.2984(3) -0.8071(3) 0.0427(7) Uani 1 1 d . . . . .
H6 H -0.0388 -0.2337 -0.7584 0.051 Uiso 1 1 calc R . . . .
C7 C -0.1020(3) -0.1921(3) -0.9976(3) 0.0390(6) Uani 1 1 d . . . . .
C8 C -0.1840(3) -0.0058(3) -1.0586(3) 0.0393(6) Uani 1 1 d . . . . .
C9 C -0.1969(4) 0.1269(3) -1.0561(3) 0.0466(7) Uani 1 1 d . . . . .
H9 H -0.2595 0.1691 -1.1146 0.056 Uiso 1 1 calc R . . . .
C10 C -0.1170(4) 0.1915(3) -0.9674(4) 0.0498(8) Uani 1 1 d . . . . .
H10 H -0.1268 0.2787 -0.9638 0.060 Uiso 1 1 calc R . . . .
C11 C -0.0180(4) 0.1282(3) -0.8793(3) 0.0475(7) Uani 1 1 d . . . . .
H11 H 0.0391 0.1745 -0.8207 0.057 Uiso 1 1 calc R . . . .
C12 C -0.0063(4) 0.0016(3) -0.8801(3) 0.0408(7) Uani 1 1 d . . . . .
H12 H 0.0579 -0.0400 -0.8223 0.049 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
N1 C7 1.386(3) . ?
N1 C8 1.388(4) . ?
N1 C12 1.381(4) . ?
N2 N3 1.376(4) . ?
N2 C7 1.309(4) . ?
N3 C8 1.321(4) . ?
C1 C2 1.395(4) . ?
C1 C6 1.382(4) . ?
C1 C7 1.466(4) . ?
C2 C3 1.377(5) . ?
C3 C4 1.386(5) . ?
C4 C5 1.384(5) . ?
C5 C6 1.388(5) . ?
C8 C9 1.412(4) . ?
C9 C10 1.350(5) . ?
C10 C11 1.421(5) . ?
C11 C12 1.347(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 104.3(2) . . ?
C12 N1 C7 133.4(3) . . ?
C12 N1 C8 122.1(2) . . ?
C7 N2 N3 109.8(2) . . ?
C8 N3 N2 106.3(3) . . ?
C2 C1 C7 117.7(3) . . ?
C6 C1 C2 119.4(3) . . ?
C6 C1 C7 122.9(3) . . ?
C3 C2 C1 120.5(3) . . ?
C2 C3 C4 120.2(3) . . ?
C5 C4 C3 119.6(3) . . ?
C4 C5 C6 120.4(3) . . ?
C1 C6 C5 120.0(3) . . ?
N1 C7 C1 126.0(3) . . ?
N2 C7 N1 109.1(3) . . ?
N2 C7 C1 124.8(3) . . ?
N1 C8 C9 118.7(3) . . ?
N3 C8 N1 110.5(2) . . ?
N3 C8 C9 130.8(3) . . ?
C10 C9 C8 118.9(3) . . ?
C9 C10 C11 121.0(3) . . ?
C12 C11 C10 120.5(3) . . ?
C11 C12 N1 118.7(3) . . ?

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
N1 C8 C9 C10 0.9(4) . . . . ?
N2 N3 C8 N1 -1.1(3) . . . . ?
N2 N3 C8 C9 179.2(3) . . . . ?
N3 N2 C7 N1 -0.2(3) . . . . ?
N3 N2 C7 C1 -177.3(3) . . . . ?
N3 C8 C9 C10 -179.4(3) . . . . ?
C1 C2 C3 C4 -1.4(5) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C2 C1 C7 N1 -141.5(3) . . . . ?
C2 C1 C7 N2 35.1(4) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C6 C1 C7 N1 38.9(4) . . . . ?
C6 C1 C7 N2 -144.5(3) . . . . ?
C7 N1 C8 N3 1.0(3) . . . . ?
C7 N1 C8 C9 -179.3(2) . . . . ?
C7 N1 C12 C11 177.4(3) . . . . ?
C7 N2 N3 C8 0.8(4) . . . . ?
C7 C1 C2 C3 -179.3(3) . . . . ?
C7 C1 C6 C5 -179.4(3) . . . . ?
C8 N1 C7 N2 -0.4(3) . . . . ?
C8 N1 C7 C1 176.6(3) . . . . ?
C8 N1 C12 C11 2.1(4) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C9 C10 C11 C12 -2.2(5) . . . . ?
C10 C11 C12 N1 0.4(5) . . . . ?
C12 N1 C7 N2 -176.3(3) . . . . ?
C12 N1 C7 C1 0.7(5) . . . . ?
C12 N1 C8 N3 177.4(3) . . . . ?
C12 N1 C8 C9 -2.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
