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

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

data_exp_5375
_database_code_depnum_ccdc_archive 'CCDC 1441369'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;
_audit_creation_date             2015-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        1f
_chemical_formula_moiety         'C14 H8 F2 N4'
_chemical_formula_sum            'C14 H8 F2 N4'
_chemical_formula_weight         270.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 N4 F2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.3750(2)
_cell_length_b                   20.1126(13)
_cell_length_c                   13.1678(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.317(6)
_cell_angle_gamma                90
_cell_volume                     1146.50(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    141(50)
_cell_measurement_theta_max      28.2380
_cell_measurement_theta_min      4.6810
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.127
_diffrn_ambient_temperature      141(50)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   10.00   37.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -38.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   -2.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -38.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   87.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   38.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
  4 omega   11.00   87.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   38.0000  -90.0000 76

#__ type_ start__ end____ width___ exp.time_
  5 omega  -79.00  100.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017    0.0000   90.0000 179

#__ type_ start__ end____ width___ exp.time_
  6 omega   19.00   78.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017 -141.0000   24.0000 59

#__ type_ start__ end____ width___ exp.time_
  7 omega  -20.00   30.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -99.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega  -67.00  -31.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  121.0000   41.0029 36

#__ type_ start__ end____ width___ exp.time_
  9 omega  -72.00  -42.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  129.0000  131.2112 30
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0607669000
_diffrn_orient_matrix_UB_12      0.0210264000
_diffrn_orient_matrix_UB_13      0.0412569000
_diffrn_orient_matrix_UB_21      -0.0368307000
_diffrn_orient_matrix_UB_22      0.0282679000
_diffrn_orient_matrix_UB_23      -0.0316549000
_diffrn_orient_matrix_UB_31      -0.1476188000
_diffrn_orient_matrix_UB_32      0.0016129000
_diffrn_orient_matrix_UB_33      0.0161270000
_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                1644
_reflns_number_total             2269
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.046
_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)+(0.0360P)²+0.7627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1153
_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:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.9860(5) 0.35192(11) 0.40702(16) 0.0247(5) Uani 1 1 d . . . . .
C2 C 0.7785(5) 0.44584(11) 0.39732(16) 0.0251(5) Uani 1 1 d . . . . .
C3 C 0.4223(5) 0.50684(11) 0.30417(17) 0.0272(5) Uani 1 1 d . . . . .
C4 C 0.4122(5) 0.44323(11) 0.25917(16) 0.0257(5) Uani 1 1 d . . . . .
C5 C 0.2102(5) 0.42702(12) 0.17236(17) 0.0311(5) Uani 1 1 d . . . . .
H5 H 0.2051 0.3838 0.1432 0.037 Uiso 1 1 calc R . . . .
C6 C 0.0156(5) 0.47707(13) 0.13005(19) 0.0364(6) Uani 1 1 d . . . . .
H6 H -0.1268 0.4681 0.0700 0.044 Uiso 1 1 calc R . . . .
C7 C 0.0237(5) 0.54043(13) 0.17349(19) 0.0364(6) Uani 1 1 d . . . . .
H7 H -0.1123 0.5737 0.1419 0.044 Uiso 1 1 calc R . . . .
C8 C 0.2243(5) 0.55620(12) 0.26128(18) 0.0319(5) Uani 1 1 d . . . . .
H8 H 0.2260 0.5993 0.2910 0.038 Uiso 1 1 calc R . . . .
C9 C 1.1954(5) 0.29708(11) 0.44367(17) 0.0258(5) Uani 1 1 d . . . . .
C10 C 1.2715(5) 0.24657(12) 0.37944(18) 0.0310(5) Uani 1 1 d . . . . .
C11 C 1.4723(5) 0.19576(12) 0.4111(2) 0.0380(6) Uani 1 1 d . . . . .
H11 H 1.5181 0.1627 0.3640 0.046 Uiso 1 1 calc R . . . .
C12 C 1.6055(5) 0.19354(13) 0.5118(2) 0.0415(6) Uani 1 1 d . . . . .
H12 H 1.7448 0.1586 0.5348 0.050 Uiso 1 1 calc R . . . .
C13 C 1.5389(6) 0.24169(12) 0.5804(2) 0.0400(6) Uani 1 1 d . . . . .
H13 H 1.6290 0.2401 0.6504 0.048 Uiso 1 1 calc R . . . .
C14 C 1.3392(5) 0.29179(11) 0.54456(17) 0.0312(5) Uani 1 1 d . . . . .
F1 F 1.1472(3) 0.24809(7) 0.27962(11) 0.0462(4) Uani 1 1 d . . . . .
F2 F 1.2768(4) 0.33851(7) 0.61321(10) 0.0435(4) Uani 1 1 d . . . . .
H4 H 0.733(6) 0.5429(14) 0.433(2) 0.051(8) Uiso 1 1 d . . . . .
N1 N 0.7718(4) 0.34564(9) 0.32459(14) 0.0270(4) Uani 1 1 d . . . . .
N2 N 0.6394(4) 0.40752(9) 0.32065(14) 0.0260(4) Uani 1 1 d . . . . .
N3 N 1.0019(4) 0.41322(9) 0.45529(14) 0.0268(4) Uani 1 1 d . . . . .
N4 N 0.6483(4) 0.50718(10) 0.39067(15) 0.0285(4) Uani 1 1 d . . . . .

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
C1 0.0271(11) 0.0249(12) 0.0218(11) -0.0006(9) 0.0031(9) -0.0035(9)
C2 0.0268(11) 0.0241(12) 0.0242(12) -0.0006(9) 0.0033(9) -0.0025(9)
C3 0.0252(10) 0.0304(13) 0.0265(12) 0.0023(10) 0.0055(9) -0.0019(9)
C4 0.0236(10) 0.0301(12) 0.0235(11) 0.0026(9) 0.0033(9) -0.0007(9)
C5 0.0297(12) 0.0342(14) 0.0280(13) 0.0009(10) -0.0006(10) -0.0029(10)
C6 0.0311(12) 0.0462(16) 0.0299(13) 0.0061(11) -0.0019(10) -0.0035(11)
C7 0.0318(12) 0.0390(15) 0.0375(15) 0.0107(11) 0.0024(11) 0.0060(11)
C8 0.0324(12) 0.0295(13) 0.0341(13) 0.0043(10) 0.0061(11) 0.0025(10)
C9 0.0244(11) 0.0233(12) 0.0294(12) 0.0031(9) 0.0029(9) -0.0041(9)
C10 0.0309(12) 0.0312(13) 0.0292(13) -0.0028(10) -0.0012(10) -0.0035(10)
C11 0.0323(12) 0.0280(13) 0.0533(17) -0.0038(12) 0.0050(12) 0.0004(10)
C12 0.0327(13) 0.0315(14) 0.0581(18) 0.0091(13) -0.0005(13) 0.0036(11)
C13 0.0382(13) 0.0358(15) 0.0426(15) 0.0098(12) -0.0057(12) -0.0015(11)
C14 0.0371(13) 0.0271(13) 0.0285(13) 0.0023(10) 0.0023(10) -0.0029(10)
F1 0.0528(9) 0.0473(9) 0.0356(9) -0.0140(7) -0.0033(7) 0.0114(7)
F2 0.0647(10) 0.0381(8) 0.0251(7) 0.0007(6) -0.0018(7) 0.0070(7)
N1 0.0296(10) 0.0234(10) 0.0270(10) 0.0005(8) 0.0010(8) -0.0001(8)
N2 0.0266(9) 0.0261(10) 0.0241(10) -0.0014(8) -0.0003(8) -0.0007(8)
N3 0.0305(10) 0.0254(10) 0.0233(10) -0.0004(8) -0.0005(8) -0.0004(8)
N4 0.0325(10) 0.0251(11) 0.0263(10) -0.0010(8) -0.0019(9) 0.0012(8)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.470(3) . ?
C1 N1 1.333(3) . ?
C1 N3 1.384(3) . ?
C2 N2 1.344(3) . ?
C2 N3 1.324(3) . ?
C2 N4 1.356(3) . ?
C3 C4 1.408(3) . ?
C3 C8 1.383(3) . ?
C3 N4 1.396(3) . ?
C4 C5 1.379(3) . ?
C4 N2 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(3) . ?
C9 C14 1.389(3) . ?
C10 C11 1.373(3) . ?
C10 F1 1.348(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.372(3) . ?
C14 F2 1.359(3) . ?
N1 N2 1.371(2) . ?
N4 H4 0.95(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C9 121.83(19) . . ?
N1 C1 N3 116.16(19) . . ?
N3 C1 C9 122.00(19) . . ?
N2 C2 N4 109.43(19) . . ?
N3 C2 N2 111.42(19) . . ?
N3 C2 N4 139.1(2) . . ?
C8 C3 C4 120.0(2) . . ?
C8 C3 N4 131.1(2) . . ?
N4 C3 C4 108.85(19) . . ?
C5 C4 C3 122.8(2) . . ?
C5 C4 N2 132.9(2) . . ?
N2 C4 C3 104.38(18) . . ?
C4 C5 H5 121.8 . . ?
C4 C5 C6 116.4(2) . . ?
C6 C5 H5 121.8 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.8(2) . . ?
C8 C7 H7 119.1 . . ?
C3 C8 C7 117.4(2) . . ?
C3 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
C10 C9 C1 122.7(2) . . ?
C14 C9 C1 123.1(2) . . ?
C14 C9 C10 114.2(2) . . ?
C11 C10 C9 123.9(2) . . ?
F1 C10 C9 118.5(2) . . ?
F1 C10 C11 117.6(2) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.3(2) . . ?
C14 C13 H13 120.9 . . ?
C13 C14 C9 124.3(2) . . ?
F2 C14 C9 118.4(2) . . ?
F2 C14 C13 117.3(2) . . ?
C1 N1 N2 100.84(17) . . ?
C2 N2 C4 110.48(18) . . ?
C2 N2 N1 110.45(17) . . ?
N1 N2 C4 139.02(18) . . ?
C2 N3 C1 101.12(18) . . ?
C2 N4 C3 106.84(19) . . ?
C2 N4 H4 121.8(17) . . ?
C3 N4 H4 130.5(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_5325
_database_code_depnum_ccdc_archive 'CCDC 1441370'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;
_audit_creation_date             2015-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        4i
_chemical_formula_moiety         'C14 H9 N3 O'
_chemical_formula_sum            'C14 H9 N3 O'
_chemical_formula_weight         235.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1'
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      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                   21.401(2)
_cell_length_b                   4.7059(5)
_cell_length_c                   10.6453(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1072.10(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    936
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      26.5310
_cell_measurement_theta_min      4.2310
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3244
_diffrn_reflns_point_group_measured_fraction_full 0.791
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.808
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   36.00   79.00   1.0000    2.5600
omega____ theta____ kappa____ phi______ frames
    -       10.7017  178.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   34.00   1.0000    2.5600
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000  -60.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00  100.00   1.0000    2.5600
omega____ theta____ kappa____ phi______ frames
    -       10.7017  178.0000 -120.0000 64
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0322416000
_diffrn_orient_matrix_UB_12      -0.0345863000
_diffrn_orient_matrix_UB_13      0.0013572000
_diffrn_orient_matrix_UB_21      -0.0066011000
_diffrn_orient_matrix_UB_22      0.1192983000
_diffrn_orient_matrix_UB_23      -0.0384539000
_diffrn_orient_matrix_UB_31      0.0038327000
_diffrn_orient_matrix_UB_32      -0.0854083000
_diffrn_orient_matrix_UB_33      -0.0544144000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.480
_reflns_Friedel_fraction_full    0.559
_reflns_Friedel_fraction_max     0.537
_reflns_number_gt                1457
_reflns_number_total             1646
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 437 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_coef       0.017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1646
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.125
_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)+(0.0507P)²+0.1363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1112
_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:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37005(15) 0.9141(7) 0.9724(4) 0.0311(8) Uani 1 1 d . . . . .
C2 C 0.29563(15) 0.7727(8) 1.0785(4) 0.0322(8) Uani 1 1 d . . . . .
C3 C 0.21535(16) 0.4875(7) 1.0823(4) 0.0311(8) Uani 1 1 d . . . . .
C4 C 0.24489(15) 0.4438(7) 0.9663(4) 0.0301(8) Uani 1 1 d . . . . .
C5 C 0.22287(17) 0.2486(8) 0.8823(4) 0.0343(9) Uani 1 1 d . . . . .
H5 H 0.2427 0.2170 0.8037 0.041 Uiso 1 1 calc R . . . .
C6 C 0.16989(16) 0.0988(8) 0.9180(4) 0.0359(9) Uani 1 1 d . . . . .
H6 H 0.1530 -0.0380 0.8618 0.043 Uiso 1 1 calc R . . . .
C7 C 0.14082(16) 0.1417(8) 1.0325(4) 0.0351(9) Uani 1 1 d . . . . .
H7 H 0.1048 0.0330 1.0531 0.042 Uiso 1 1 calc R . . . .
C8 C 0.16317(16) 0.3402(8) 1.1178(3) 0.0343(9) Uani 1 1 d . . . . .
H8 H 0.1433 0.3719 1.1964 0.041 Uiso 1 1 calc R . . . .
C9 C 0.42658(16) 1.0718(7) 0.9394(4) 0.0317(8) Uani 1 1 d . . . . .
C10 C 0.45760(17) 1.0173(8) 0.8263(4) 0.0363(9) Uani 1 1 d . . . . .
H10 H 0.4416 0.8788 0.7698 0.044 Uiso 1 1 calc R . . . .
C11 C 0.51109(18) 1.1636(8) 0.7969(4) 0.0402(10) Uani 1 1 d . . . . .
H11 H 0.5321 1.1257 0.7201 0.048 Uiso 1 1 calc R . . . .
C12 C 0.53463(17) 1.3664(8) 0.8786(4) 0.0397(10) Uani 1 1 d . . . . .
H12 H 0.5716 1.4676 0.8579 0.048 Uiso 1 1 calc R . . . .
C13 C 0.50407(16) 1.4205(8) 0.9898(4) 0.0396(10) Uani 1 1 d . . . . .
H13 H 0.5202 1.5589 1.0461 0.048 Uiso 1 1 calc R . . . .
C14 C 0.45017(17) 1.2747(8) 1.0201(4) 0.0370(9) Uani 1 1 d . . . . .
H14 H 0.4292 1.3143 1.0968 0.044 Uiso 1 1 calc R . . . .
N1 N 0.34393(12) 0.7235(6) 0.8972(3) 0.0311(7) Uani 1 1 d . . . . .
N2 N 0.29508(12) 0.6321(6) 0.9694(3) 0.0310(7) Uani 1 1 d . . . . .
N3 N 0.34086(14) 0.9513(6) 1.0893(3) 0.0355(8) Uani 1 1 d . . . . .
O1 O 0.24730(12) 0.6925(5) 1.1522(3) 0.0374(7) Uani 1 1 d . . . . .

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
C1 0.0340(17) 0.0311(17) 0.0281(19) 0.0017(18) -0.0102(17) 0.0033(15)
C2 0.0336(18) 0.0381(19) 0.0248(19) -0.0022(18) -0.0022(18) 0.0017(15)
C3 0.0355(17) 0.0310(18) 0.027(2) -0.0023(17) -0.0111(18) 0.0040(14)
C4 0.0328(17) 0.0314(17) 0.026(2) 0.0030(17) -0.0054(17) 0.0058(14)
C5 0.0396(18) 0.0366(19) 0.027(2) 0.0004(17) -0.0015(18) 0.0049(17)
C6 0.0396(19) 0.0371(19) 0.031(2) -0.0020(19) -0.0008(19) -0.0013(17)
C7 0.0347(18) 0.035(2) 0.036(2) 0.0033(17) 0.0001(18) 0.0004(16)
C8 0.0370(18) 0.043(2) 0.023(2) -0.0003(18) -0.0009(17) 0.0070(17)
C9 0.0328(16) 0.0296(17) 0.033(2) 0.0032(16) -0.0030(16) 0.0059(14)
C10 0.041(2) 0.0312(19) 0.037(2) 0.0010(18) -0.0103(19) 0.0001(16)
C11 0.044(2) 0.041(2) 0.036(2) 0.0042(19) 0.0026(19) 0.0072(18)
C12 0.0371(19) 0.035(2) 0.047(3) 0.004(2) -0.002(2) 0.0003(17)
C13 0.0385(19) 0.036(2) 0.044(3) -0.005(2) -0.0063(19) -0.0008(16)
C14 0.0386(18) 0.036(2) 0.036(2) 0.0003(18) -0.0040(19) 0.0023(17)
N1 0.0310(14) 0.0350(15) 0.0274(16) -0.0025(15) -0.0015(14) 0.0025(12)
N2 0.0351(15) 0.0344(15) 0.0235(16) 0.0000(14) -0.0026(14) 0.0031(12)
N3 0.0419(16) 0.0365(17) 0.0281(18) -0.0060(14) -0.0047(15) 0.0041(13)
O1 0.0417(13) 0.0427(15) 0.0279(14) -0.0043(13) -0.0016(12) -0.0025(13)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9 1.462(4) . ?
C1 N1 1.326(4) . ?
C1 N3 1.403(5) . ?
C2 N2 1.337(4) . ?
C2 N3 1.287(4) . ?
C2 O1 1.352(4) . ?
C3 C4 1.403(5) . ?
C3 C8 1.367(5) . ?
C3 O1 1.397(4) . ?
C4 C5 1.365(5) . ?
C4 N2 1.393(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.383(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(5) . ?
C9 C14 1.380(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.372(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(5) . ?
C14 H14 0.9500 . ?
N1 N2 1.367(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
N1 C1 C9 123.2(4) . . ?
N1 C1 N3 115.6(3) . . ?
N3 C1 C9 121.2(3) . . ?
N2 C2 O1 111.1(3) . . ?
N3 C2 N2 114.0(3) . . ?
N3 C2 O1 134.9(4) . . ?
C8 C3 C4 122.5(3) . . ?
C8 C3 O1 127.1(3) . . ?
O1 C3 C4 110.5(3) . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 N2 135.2(3) . . ?
N2 C4 C3 103.5(3) . . ?
C4 C5 H5 121.8 . . ?
C4 C5 C6 116.4(4) . . ?
C6 C5 H5 121.8 . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.3(4) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.3(3) . . ?
C8 C7 H7 119.3 . . ?
C3 C8 C7 116.2(3) . . ?
C3 C8 H8 121.9 . . ?
C7 C8 H8 121.9 . . ?
C10 C9 C1 120.4(3) . . ?
C14 C9 C1 120.3(3) . . ?
C14 C9 C10 119.3(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(4) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 120.3(4) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C1 N1 N2 101.3(3) . . ?
C2 N2 C4 110.0(3) . . ?
C2 N2 N1 109.0(3) . . ?
N1 N2 C4 140.9(3) . . ?
C2 N3 C1 100.0(3) . . ?
C2 O1 C3 105.0(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_5557
_database_code_depnum_ccdc_archive 'CCDC 1441371'
_audit_update_record             
;
2015-12-09 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;
_audit_creation_date             2015-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        4a
_chemical_formula_moiety         'C16 H14 N4'
_chemical_formula_sum            'C16 H14 N4'
_chemical_formula_weight         262.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H10N4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.9753(6)
_cell_length_b                   15.9285(17)
_cell_length_c                   13.4470(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.062(11)
_cell_angle_gamma                90
_cell_volume                     1279.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    738
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      26.3870
_cell_measurement_theta_min      3.7230
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.877
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3290
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         3.642
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.877
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -19.0000   60.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega  -69.00  -19.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -19.0000   60.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0065264000
_diffrn_orient_matrix_UB_12      0.0410949000
_diffrn_orient_matrix_UB_13      0.0201594000
_diffrn_orient_matrix_UB_21      -0.1006203000
_diffrn_orient_matrix_UB_22      -0.0070862000
_diffrn_orient_matrix_UB_23      0.0266555000
_diffrn_orient_matrix_UB_31      0.0626007000
_diffrn_orient_matrix_UB_32      -0.0156613000
_diffrn_orient_matrix_UB_33      0.0407982000
_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                1365
_reflns_number_total             2023
_reflns_odcompleteness_completeness 87.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.085
_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)+(0.0522P)²+0.1388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1324
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7504(4) 0.04119(15) 0.92980(17) 0.0230(6) Uani 1 1 d . . . . .
C2 C 0.9204(4) 0.13294(15) 1.01143(17) 0.0229(6) Uani 1 1 d . . . . .
C3 C 0.9595(4) 0.01340(15) 0.79482(16) 0.0223(6) Uani 1 1 d . . . . .
C4 C 0.7635(4) -0.03567(15) 0.79362(17) 0.0242(6) Uani 1 1 d . . . . .
C5 C 0.7270(4) -0.09100(16) 0.71646(17) 0.0270(6) Uani 1 1 d . . . . .
H5 H 0.5949 -0.1242 0.7147 0.032 Uiso 1 1 calc R . . . .
C6 C 0.8851(4) -0.09772(16) 0.64145(18) 0.0270(6) Uani 1 1 d . . . . .
C7 C 1.0823(4) -0.04892(16) 0.64373(18) 0.0277(6) Uani 1 1 d . . . . .
C8 C 1.1188(4) 0.00725(15) 0.72140(17) 0.0264(6) Uani 1 1 d . . . . .
H8 H 1.2506 0.0405 0.7236 0.032 Uiso 1 1 calc R . . . .
C9 C 0.8449(5) -0.15908(18) 0.5579(2) 0.0387(7) Uani 1 1 d . . . . .
H9A H 0.7009 -0.1873 0.5680 0.058 Uiso 1 1 calc GR . . . .
H9B H 0.9651 -0.2009 0.5571 0.058 Uiso 1 1 calc GR . . . .
H9C H 0.8424 -0.1289 0.4944 0.058 Uiso 1 1 calc GR . . . .
C10 C 1.2536(5) -0.05674(19) 0.56238(19) 0.0382(7) Uani 1 1 d . . . . .
H10A H 1.3796 -0.0191 0.5763 0.057 Uiso 1 1 calc GR . . . .
H10B H 1.1855 -0.0414 0.4986 0.057 Uiso 1 1 calc GR . . . .
H10C H 1.3075 -0.1148 0.5592 0.057 Uiso 1 1 calc GR . . . .
C11 C 0.9699(4) 0.19430(14) 1.08971(18) 0.0230(6) Uani 1 1 d . . . . .
C12 C 1.1744(4) 0.23601(16) 1.09241(19) 0.0306(7) Uani 1 1 d . . . . .
H12 H 1.2849 0.2243 1.0436 0.037 Uiso 1 1 calc R . . . .
C13 C 1.2173(5) 0.29444(16) 1.1660(2) 0.0373(7) Uani 1 1 d . . . . .
H13 H 1.3566 0.3232 1.1673 0.045 Uiso 1 1 calc R . . . .
C14 C 1.0578(5) 0.31118(17) 1.2377(2) 0.0380(7) Uani 1 1 d . . . . .
H14 H 1.0877 0.3514 1.2881 0.046 Uiso 1 1 calc R . . . .
C15 C 0.8549(5) 0.26945(16) 1.2362(2) 0.0357(7) Uani 1 1 d . . . . .
H15 H 0.7458 0.2806 1.2858 0.043 Uiso 1 1 calc R . . . .
C16 C 0.8115(4) 0.21143(15) 1.16227(19) 0.0293(6) Uani 1 1 d . . . . .
H16 H 0.6717 0.1830 1.1611 0.035 Uiso 1 1 calc R . . . .
H1 H 0.494(6) -0.0496(18) 0.906(2) 0.061(9) Uiso 1 1 d . . . . .
N1 N 0.6349(4) -0.01750(13) 0.87747(15) 0.0259(5) Uani 1 1 d . . . . .
N2 N 0.7287(3) 0.08514(13) 1.01302(14) 0.0246(5) Uani 1 1 d . . . . .
N3 N 1.0561(3) 0.12131(12) 0.93379(14) 0.0255(5) Uani 1 1 d . . . . .
N4 N 0.9412(3) 0.06068(12) 0.88211(14) 0.0235(5) Uani 1 1 d . . . . .

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
C1 0.0237(14) 0.0217(13) 0.0237(13) 0.0021(11) 0.0010(12) -0.0023(11)
C2 0.0263(13) 0.0195(13) 0.0229(12) 0.0040(10) -0.0002(11) 0.0010(11)
C3 0.0246(14) 0.0219(13) 0.0206(13) 0.0010(10) -0.0008(11) 0.0024(11)
C4 0.0283(14) 0.0247(14) 0.0197(12) 0.0036(11) -0.0001(11) 0.0031(12)
C5 0.0278(14) 0.0268(14) 0.0264(14) 0.0017(11) -0.0030(12) -0.0010(12)
C6 0.0313(15) 0.0270(15) 0.0229(13) -0.0014(11) -0.0015(12) 0.0056(12)
C7 0.0273(14) 0.0304(15) 0.0253(14) 0.0012(11) 0.0015(12) 0.0068(12)
C8 0.0254(14) 0.0283(15) 0.0254(13) 0.0007(11) 0.0009(11) 0.0010(11)
C9 0.0374(16) 0.0435(18) 0.0352(16) -0.0112(13) 0.0017(13) 0.0010(14)
C10 0.0324(16) 0.0513(19) 0.0308(15) -0.0051(13) 0.0065(13) 0.0016(14)
C11 0.0263(14) 0.0182(13) 0.0244(14) 0.0029(10) -0.0026(11) 0.0009(11)
C12 0.0308(15) 0.0286(15) 0.0325(15) 0.0020(12) 0.0005(12) -0.0044(12)
C13 0.0362(16) 0.0299(16) 0.0458(18) -0.0003(13) -0.0083(14) -0.0116(13)
C14 0.0465(18) 0.0266(16) 0.0410(17) -0.0094(12) -0.0066(15) -0.0033(14)
C15 0.0392(17) 0.0331(16) 0.0347(15) -0.0081(13) 0.0018(13) 0.0057(14)
C16 0.0288(15) 0.0260(15) 0.0331(15) -0.0016(12) -0.0006(12) -0.0037(12)
N1 0.0281(12) 0.0274(12) 0.0222(11) -0.0013(9) 0.0025(10) -0.0061(10)
N2 0.0247(11) 0.0236(12) 0.0256(11) 0.0005(9) 0.0016(9) -0.0034(10)
N3 0.0273(12) 0.0236(12) 0.0257(11) -0.0010(9) 0.0000(9) -0.0043(10)
N4 0.0244(11) 0.0229(12) 0.0233(11) -0.0009(9) 0.0011(9) -0.0027(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.358(3) . ?
C1 N2 1.327(3) . ?
C1 N4 1.345(3) . ?
C2 C11 1.466(3) . ?
C2 N2 1.375(3) . ?
C2 N3 1.336(3) . ?
C3 C4 1.408(3) . ?
C3 C8 1.376(4) . ?
C3 N4 1.399(3) . ?
C4 C5 1.378(3) . ?
C4 N1 1.396(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(4) . ?
C6 C7 1.412(4) . ?
C6 C9 1.508(3) . ?
C7 C8 1.392(3) . ?
C7 C10 1.504(4) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.392(3) . ?
C11 C16 1.387(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9500 . ?
N1 H1 1.05(3) . ?
N3 N4 1.373(3) . ?

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 C1 N1 138.6(2) . . ?
N2 C1 N4 111.4(2) . . ?
N4 C1 N1 110.0(2) . . ?
N2 C2 C11 121.7(2) . . ?
N3 C2 C11 122.1(2) . . ?
N3 C2 N2 116.2(2) . . ?
C8 C3 C4 121.9(2) . . ?
C8 C3 N4 134.0(2) . . ?
N4 C3 C4 104.0(2) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 N1 130.8(2) . . ?
N1 C4 C3 109.5(2) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 120.7(2) . . ?
C5 C6 C9 118.9(2) . . ?
C7 C6 C9 120.4(2) . . ?
C6 C7 C10 120.5(2) . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 C10 119.5(2) . . ?
C3 C8 C7 118.4(2) . . ?
C3 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C2 120.9(2) . . ?
C16 C11 C2 119.9(2) . . ?
C16 C11 C12 119.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 H16 119.7 . . ?
C1 N1 C4 106.3(2) . . ?
C1 N1 H1 123.5(16) . . ?
C4 N1 H1 129.1(17) . . ?
C1 N2 C2 101.4(2) . . ?
C2 N3 N4 100.92(19) . . ?
C1 N4 C3 110.06(19) . . ?
C1 N4 N3 110.2(2) . . ?
N3 N4 C3 139.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
