# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_lilh_0306_2
_database_code_depnum_ccdc_archive 'CCDC 1852258'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_audit_creation_date             2018-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H17 N5'
_chemical_formula_sum            'C13 H17 N5'
_chemical_formula_weight         243.32
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.970(2)
_cell_length_b                   7.2564(6)
_cell_length_c                   17.3888(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.224(10)
_cell_angle_gamma                90.00
_cell_volume                     2540.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1473
_cell_measurement_temperature    290.04(10)
_cell_measurement_theta_max      68.6910
_cell_measurement_theta_min      4.3910
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4434
_diffrn_reflns_theta_full        69.99
_diffrn_reflns_theta_max         69.99
_diffrn_reflns_theta_min         4.39
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.04(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  19.00   1.50    2.00    --    0.00  57.00-120.00   18
  2  ω     22.00  49.00   1.50    2.00    --    0.00  57.00-120.00   18
  3  ω     28.00 115.00   1.50    2.00    --   54.00  38.00 -30.00   58
  4  ω     88.00 178.00   1.50    4.00    --  108.00  25.00-120.00   60
  5  ω    117.00 166.50   1.50    4.00    --  108.00 111.00 -90.00   33
  6  ω    123.00 150.00   1.50    4.00    --  108.00 178.00  30.00   18
  7  ω     96.00 130.50   1.50    4.00    --  108.00  63.00 -90.00   23
  8  ω     85.00 178.00   1.50    4.00    --  108.00  38.00 -30.00   62
  9  ω     89.00 134.00   1.50    4.00    --  108.00 -38.00 -60.00   30
 10  ω     69.00 114.00   1.50    4.00    --  108.00-111.00-180.00   30
 11  ω     40.00 137.50   1.50    4.00    --  108.00 -77.00-180.00   65
 12  ω     39.00 108.00   1.50    2.00    --   54.00-125.00   0.00   46
 13  ω     40.00  70.00   1.50    4.00    --  108.00 -38.00 -60.00   20
 14  ω    -18.00  79.50   1.50    2.00    --   54.00 -38.00 150.00   65
 15  ω     32.00  63.50   1.50    2.00    --    0.00  57.00 150.00   21
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0674408000
_diffrn_orient_matrix_UB_12      -0.0066905000
_diffrn_orient_matrix_UB_13      0.0189864000
_diffrn_orient_matrix_UB_21      0.0355213000
_diffrn_orient_matrix_UB_22      0.0263321000
_diffrn_orient_matrix_UB_23      0.0896870000
_diffrn_orient_matrix_UB_31      -0.0065922000
_diffrn_orient_matrix_UB_32      0.2105332000
_diffrn_orient_matrix_UB_33      -0.0107350000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1798
_reflns_number_total             2362
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.060
_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)+(0.0521P)²+0.2389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1257
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
;
_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
N1 N 0.06896(7) 0.2811(2) -0.04821(8) 0.0390(4) Uani 1 d . . .
N2 N -0.04258(7) 0.2767(2) -0.04478(9) 0.0417(4) Uani 1 d . . .
N3 N -0.07279(7) 0.2303(2) 0.01249(10) 0.0471(4) Uani 1 d . . .
N4 N -0.03065(7) 0.1786(2) 0.07807(9) 0.0431(4) Uani 1 d . . .
N5 N 0.03064(6) 0.18839(19) 0.06495(8) 0.0322(3) Uani 1 d . . .
C1 C 0.13952(9) 0.2440(3) -0.01765(11) 0.0398(4) Uani 1 d . . .
H1A H 0.1478 0.1134 -0.0078 0.048 Uiso 1 calc . . R
H1B H 0.1588 0.3114 0.0315 0.048 Uiso 1 calc . . R
C2 C 0.16716(11) 0.3111(3) -0.08486(13) 0.0548(5) Uani 1 d . . .
H2A H 0.1791 0.4404 -0.0781 0.066 Uiso 1 calc . . R
H2B H 0.2059 0.2402 -0.0867 0.066 Uiso 1 calc . . R
C3 C 0.11035(11) 0.2808(3) -0.16002(12) 0.0506(5) Uani 1 d . . .
H3A H 0.1144 0.3614 -0.2029 0.061 Uiso 1 calc . . R
H3B H 0.1090 0.1539 -0.1779 0.061 Uiso 1 calc . . R
C4 C 0.04930(10) 0.3276(3) -0.13376(11) 0.0487(5) Uani 1 d . . .
H4A H 0.0383 0.4573 -0.1419 0.058 Uiso 1 calc . . R
H4B H 0.0114 0.2548 -0.1628 0.058 Uiso 1 calc . . R
C5 C 0.02228(8) 0.2507(2) -0.01082(9) 0.0320(4) Uani 1 d . . .
C7 C 0.08846(8) 0.1518(2) 0.13295(9) 0.0317(4) Uani 1 d . . .
H7A H 0.1245 0.1055 0.1134 0.038 Uiso 1 calc . . R
H7B H 0.0773 0.0575 0.1666 0.038 Uiso 1 calc . . R
C8 C 0.11140(9) 0.3250(2) 0.18264(11) 0.0403(4) Uani 1 d . . .
H8A H 0.1248 0.4171 0.1498 0.048 Uiso 1 calc . . R
H8B H 0.0747 0.3751 0.1998 0.048 Uiso 1 calc . . R
C9 C 0.16881(8) 0.2840(2) 0.25515(9) 0.0305(4) Uani 1 d . . .
C10 C 0.23415(9) 0.3062(2) 0.25267(10) 0.0350(4) Uani 1 d . . .
H10 H 0.2428 0.3477 0.2060 0.042 Uiso 1 calc . . R
C11 C 0.28668(8) 0.2665(2) 0.31985(11) 0.0385(4) Uani 1 d . . .
H11 H 0.3302 0.2818 0.3177 0.046 Uiso 1 calc . . R
C12 C 0.27461(9) 0.2049(2) 0.38942(10) 0.0392(4) Uani 1 d . . .
H12 H 0.3098 0.1788 0.4342 0.047 Uiso 1 calc . . R
C13 C 0.20999(10) 0.1820(2) 0.39219(10) 0.0404(4) Uani 1 d . . .
H13 H 0.2016 0.1406 0.4391 0.049 Uiso 1 calc . . R
C14 C 0.15739(9) 0.2203(2) 0.32541(10) 0.0353(4) Uani 1 d . . .
H14 H 0.1140 0.2032 0.3278 0.042 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.451(2) . ?
N1 C4 1.468(2) . ?
N1 C5 1.336(2) . ?
N2 N3 1.363(2) . ?
N2 C5 1.336(2) . ?
N3 N4 1.288(2) . ?
N4 N5 1.368(2) . ?
N5 C5 1.357(2) . ?
N5 C7 1.4620(19) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.522(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.518(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.513(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.525(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.510(2) . ?
C9 C10 1.392(2) . ?
C9 C14 1.388(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(2) . ?
C14 H14 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
C1 N1 C4 112.51(15) . . ?
C5 N1 C1 127.00(15) . . ?
C5 N1 C4 119.65(15) . . ?
C5 N2 N3 105.41(14) . . ?
N4 N3 N2 112.00(14) . . ?
N3 N4 N5 106.34(15) . . ?
N4 N5 C7 117.46(14) . . ?
C5 N5 N4 107.85(13) . . ?
C5 N5 C7 134.31(14) . . ?
N1 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
N1 C1 C2 103.15(15) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 C1 103.83(16) . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 C2 103.56(16) . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
N1 C4 C3 103.45(15) . . ?
N1 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4A 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109.0 . . ?
N1 C5 N2 123.73(16) . . ?
N1 C5 N5 127.88(15) . . ?
N2 C5 N5 108.39(15) . . ?
N5 C7 H7A 109.3 . . ?
N5 C7 H7B 109.3 . . ?
N5 C7 C8 111.57(13) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.23(14) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C10 C9 C8 120.88(16) . . ?
C14 C9 C8 120.49(16) . . ?
C14 C9 C10 118.63(15) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.28(16) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.46(16) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.54(15) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.36(16) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.72(16) . . ?
C13 C14 H14 119.6 . . ?

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 C1 C2 C3 -30.2(2) . . . . ?
N2 N3 N4 N5 -0.6(2) . . . . ?
N3 N2 C5 N1 179.87(16) . . . . ?
N3 N2 C5 N5 0.55(19) . . . . ?
N3 N4 N5 C5 0.9(2) . . . . ?
N3 N4 N5 C7 174.80(15) . . . . ?
N4 N5 C5 N1 179.82(17) . . . . ?
N4 N5 C5 N2 -0.90(19) . . . . ?
N4 N5 C7 C8 -85.90(19) . . . . ?
N5 C7 C8 C9 176.98(14) . . . . ?
C1 N1 C4 C3 10.8(2) . . . . ?
C1 N1 C5 N2 -175.25(17) . . . . ?
C1 N1 C5 N5 3.9(3) . . . . ?
C1 C2 C3 C4 37.2(2) . . . . ?
C2 C3 C4 N1 -29.3(2) . . . . ?
C4 N1 C1 C2 12.2(2) . . . . ?
C4 N1 C5 N2 -6.5(3) . . . . ?
C4 N1 C5 N5 172.64(17) . . . . ?
C5 N1 C1 C2 -178.44(18) . . . . ?
C5 N1 C4 C3 -159.43(16) . . . . ?
C5 N2 N3 N4 0.0(2) . . . . ?
C5 N5 C7 C8 86.0(2) . . . . ?
C7 N5 C5 N1 7.4(3) . . . . ?
C7 N5 C5 N2 -173.34(17) . . . . ?
C7 C8 C9 C10 93.5(2) . . . . ?
C7 C8 C9 C14 -85.4(2) . . . . ?
C8 C9 C10 C11 -179.55(15) . . . . ?
C8 C9 C14 C13 179.87(15) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C9 C14 C13 0.9(2) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C9 -0.7(3) . . . . ?
C14 C9 C10 C11 -0.6(2) . . . . ?

_olex2_date_sample_data_collection 2018-03-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.412
_oxdiff_exptl_absorpt_empirical_full_min 0.710
####################################################################### 
# 
# 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_lilh_425_1n3
_database_code_depnum_ccdc_archive 'CCDC 1852260'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_audit_creation_date             2018-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H13 N5'
_chemical_formula_sum            'C11 H13 N5'
_chemical_formula_weight         215.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   10.2177(10)
_cell_length_b                   11.0976(11)
_cell_length_c                   19.154(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2171.9(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    793
_cell_measurement_temperature    189(17)
_cell_measurement_theta_max      22.5360
_cell_measurement_theta_min      4.1740
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0947
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4742
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_temperature      189(17)
_diffrn_detector_area_resol_mean 16.0733
_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  -90.00  -61.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305    0.0000  -60.0000 115
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0370121000
_diffrn_orient_matrix_UB_12      0.0492505000
_diffrn_orient_matrix_UB_13      -0.0127770000
_diffrn_orient_matrix_UB_21      0.0122256000
_diffrn_orient_matrix_UB_22      -0.0192795000
_diffrn_orient_matrix_UB_23      -0.0347962000
_diffrn_orient_matrix_UB_31      -0.0573862000
_diffrn_orient_matrix_UB_32      -0.0358128000
_diffrn_orient_matrix_UB_33      0.0009313000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1089
_reflns_number_total             2138
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.200
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      0.983
_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)+(0.0505P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1694
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
;
_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
N1 N 0.0890(2) 0.3965(2) 0.58337(11) 0.0399(6) Uani 1 d . . .
N2 N 0.1325(2) 0.5090(2) 0.60115(14) 0.0518(7) Uani 1 d . . .
N3 N 0.1860(3) 0.5525(3) 0.54575(15) 0.0570(8) Uani 1 d . . .
N4 N 0.1793(2) 0.4742(2) 0.49119(13) 0.0492(7) Uani 1 d . . .
N5 N 0.0922(2) 0.2787(2) 0.47802(11) 0.0408(7) Uani 1 d . . .
C1 C 0.0337(3) 0.3210(3) 0.63596(13) 0.0400(7) Uani 1 d . . .
C2 C -0.0726(3) 0.3622(3) 0.67357(14) 0.0481(8) Uani 1 d . . .
H2 H -0.1085 0.4374 0.6640 0.058 Uiso 1 calc . . R
C3 C -0.1249(3) 0.2910(4) 0.72541(16) 0.0636(11) Uani 1 d . . .
H3 H -0.1958 0.3186 0.7513 0.076 Uiso 1 calc . . R
C4 C -0.0729(4) 0.1798(4) 0.73901(16) 0.0687(11) Uani 1 d . . .
H4 H -0.1093 0.1315 0.7736 0.082 Uiso 1 calc . . R
C5 C 0.0341(4) 0.1392(3) 0.70110(16) 0.0667(10) Uani 1 d . . .
H5 H 0.0696 0.0638 0.7105 0.080 Uiso 1 calc . . R
C6 C 0.0881(3) 0.2103(3) 0.64945(15) 0.0550(9) Uani 1 d . . .
H6 H 0.1603 0.1836 0.6242 0.066 Uiso 1 calc . . R
C7 C 0.1181(3) 0.3772(3) 0.51529(14) 0.0375(7) Uani 1 d . . .
C9 C -0.0146(3) 0.1945(3) 0.49096(14) 0.0503(9) Uani 1 d . . .
H9A H -0.0905 0.2354 0.5100 0.060 Uiso 1 calc . . R
H9B H 0.0120 0.1310 0.5228 0.060 Uiso 1 calc . . R
C10 C -0.0430(3) 0.1446(3) 0.41878(14) 0.0523(9) Uani 1 d . . .
H10A H -0.0740 0.0622 0.4215 0.063 Uiso 1 calc . . R
H10B H -0.1079 0.1932 0.3949 0.063 Uiso 1 calc . . R
C11 C 0.0880(3) 0.1510(3) 0.38183(15) 0.0543(9) Uani 1 d . . .
H11A H 0.1451 0.0857 0.3962 0.065 Uiso 1 calc . . R
H11B H 0.0774 0.1487 0.3315 0.065 Uiso 1 calc . . R
C12 C 0.1398(3) 0.2713(3) 0.40569(14) 0.0506(9) Uani 1 d . . .
H12A H 0.2347 0.2735 0.4039 0.061 Uiso 1 calc . . R
H12B H 0.1050 0.3364 0.3775 0.061 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.368(3) . ?
N1 C1 1.427(3) . ?
N1 C7 1.355(3) . ?
N2 N3 1.288(3) . ?
N3 N4 1.361(3) . ?
N4 C7 1.327(4) . ?
N5 C7 1.332(4) . ?
N5 C9 1.459(4) . ?
N5 C12 1.471(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.373(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(4) . ?
C6 H6 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.517(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.515(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.507(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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 N1 C1 119.3(2) . . ?
C7 N1 N2 108.2(2) . . ?
C7 N1 C1 132.4(2) . . ?
N3 N2 N1 106.0(2) . . ?
N2 N3 N4 111.8(3) . . ?
C7 N4 N3 105.9(2) . . ?
C7 N5 C9 125.7(2) . . ?
C7 N5 C12 119.0(2) . . ?
C9 N5 C12 111.8(2) . . ?
C2 C1 N1 119.0(3) . . ?
C6 C1 N1 119.8(3) . . ?
C6 C1 C2 121.1(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N4 C7 N1 108.1(3) . . ?
N4 C7 N5 124.9(3) . . ?
N5 C7 N1 127.0(3) . . ?
N5 C9 H9A 111.2 . . ?
N5 C9 H9B 111.2 . . ?
N5 C9 C10 102.8(2) . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 H9A 111.2 . . ?
C10 C9 H9B 111.2 . . ?
C9 C10 H10A 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C11 C10 C9 103.9(2) . . ?
C11 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
C10 C11 H11A 111.3 . . ?
C10 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
C12 C11 C10 102.1(2) . . ?
C12 C11 H11A 111.3 . . ?
C12 C11 H11B 111.3 . . ?
N5 C12 C11 102.7(2) . . ?
N5 C12 H12A 111.2 . . ?
N5 C12 H12B 111.2 . . ?
C11 C12 H12A 111.2 . . ?
C11 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?

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 N2 N3 N4 0.5(3) . . . . ?
N1 C1 C2 C3 -178.6(3) . . . . ?
N1 C1 C6 C5 179.2(3) . . . . ?
N2 N1 C1 C2 57.1(4) . . . . ?
N2 N1 C1 C6 -121.4(3) . . . . ?
N2 N1 C7 N4 0.6(3) . . . . ?
N2 N1 C7 N5 -180.0(3) . . . . ?
N2 N3 N4 C7 -0.1(3) . . . . ?
N3 N4 C7 N1 -0.3(3) . . . . ?
N3 N4 C7 N5 -179.8(3) . . . . ?
N5 C9 C10 C11 29.6(3) . . . . ?
C1 N1 N2 N3 175.1(2) . . . . ?
C1 N1 C7 N4 -174.4(3) . . . . ?
C1 N1 C7 N5 5.1(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C7 N1 N2 N3 -0.7(3) . . . . ?
C7 N1 C1 C2 -128.3(3) . . . . ?
C7 N1 C1 C6 53.1(4) . . . . ?
C7 N5 C9 C10 151.6(3) . . . . ?
C7 N5 C12 C11 -178.4(2) . . . . ?
C9 N5 C7 N1 26.9(5) . . . . ?
C9 N5 C7 N4 -153.8(3) . . . . ?
C9 N5 C12 C11 -18.2(3) . . . . ?
C9 C10 C11 C12 -41.0(3) . . . . ?
C10 C11 C12 N5 35.6(3) . . . . ?
C12 N5 C7 N1 -175.8(3) . . . . ?
C12 N5 C7 N4 3.5(4) . . . . ?
C12 N5 C9 C10 -7.1(4) . . . . ?

_olex2_date_sample_data_collection 2018-05-16
_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_510-4n3
_database_code_depnum_ccdc_archive 'CCDC 1852259'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_audit_creation_date             2018-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_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          ?
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      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                   10.7182(8)
_cell_length_b                   7.0388(5)
_cell_length_c                   14.6427(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.420(7)
_cell_angle_gamma                90.00
_cell_volume                     1104.66(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    761
_cell_measurement_temperature    295.05(10)
_cell_measurement_theta_max      26.1500
_cell_measurement_theta_min      3.7990
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3696
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.46
_diffrn_ambient_temperature      295.05(10)
_diffrn_detector_area_resol_mean 16.0733
_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    5.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega   54.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -128.0000   67.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000   90.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0639299000
_diffrn_orient_matrix_UB_12      -0.0001569000
_diffrn_orient_matrix_UB_13      -0.0121472000
_diffrn_orient_matrix_UB_21      0.0170443000
_diffrn_orient_matrix_UB_22      -0.0054420000
_diffrn_orient_matrix_UB_23      0.0468370000
_diffrn_orient_matrix_UB_31      -0.0010992000
_diffrn_orient_matrix_UB_32      -0.1006129000
_diffrn_orient_matrix_UB_33      -0.0025145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1401
_reflns_number_total             2163
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.248
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0699P)²+0.3366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1444
_refine_ls_wR_factor_ref         0.1808
_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
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),
 C13(H13)
;
_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
N1 N 0.8910(2) 0.2524(3) 0.51954(16) 0.0447(6) Uani 1 d . . .
N2 N 1.0144(2) 0.2623(3) 0.50452(17) 0.0480(6) Uani 1 d . . .
N3 N 1.0675(2) 0.1768(4) 0.57506(18) 0.0547(7) Uani 1 d . . .
N4 N 0.9829(2) 0.1138(3) 0.63395(17) 0.0487(6) Uani 1 d . . .
C1 C 0.7528(2) 0.1103(3) 0.63873(18) 0.0376(6) Uani 1 d . . .
C2 C 0.6663(3) 0.0091(4) 0.58721(19) 0.0460(7) Uani 1 d . . .
H2 H 0.6848 -0.0269 0.5277 0.055 Uiso 1 calc . . R
C3 C 0.5525(3) -0.0377(4) 0.6250(2) 0.0525(8) Uani 1 d . . .
H3 H 0.4940 -0.1050 0.5907 0.063 Uiso 1 calc . . R
C4 C 0.5256(3) 0.0149(4) 0.7132(2) 0.0556(8) Uani 1 d . . .
H4 H 0.4489 -0.0170 0.7383 0.067 Uiso 1 calc . . R
C5 C 0.6115(3) 0.1143(4) 0.7644(2) 0.0549(8) Uani 1 d . . .
H5 H 0.5928 0.1497 0.8240 0.066 Uiso 1 calc . . R
C6 C 0.7260(3) 0.1618(4) 0.7273(2) 0.0456(7) Uani 1 d . . .
H6 H 0.7845 0.2281 0.7620 0.055 Uiso 1 calc . . R
C7 C 0.8722(2) 0.1617(3) 0.59872(16) 0.0314(6) Uani 1 d . . .
C8 C 0.7984(2) 0.3365(3) 0.45853(17) 0.0359(6) Uani 1 d . . .
C9 C 0.7962(2) 0.2817(4) 0.36808(19) 0.0445(7) Uani 1 d . . .
H9 H 0.8530 0.1926 0.3467 0.053 Uiso 1 calc . . R
C10 C 0.7087(3) 0.3607(4) 0.3096(2) 0.0499(7) Uani 1 d . . .
H10 H 0.7063 0.3241 0.2486 0.060 Uiso 1 calc . . R
C11 C 0.6250(3) 0.4932(4) 0.3411(2) 0.0514(8) Uani 1 d . . .
H11 H 0.5658 0.5454 0.3017 0.062 Uiso 1 calc . . R
C12 C 0.6294(3) 0.5484(4) 0.4322(2) 0.0528(8) Uani 1 d . . .
H12 H 0.5733 0.6387 0.4535 0.063 Uiso 1 calc . . R
C13 C 0.7159(3) 0.4706(4) 0.4910(2) 0.0481(7) Uani 1 d . . .
H13 H 0.7188 0.5078 0.5519 0.058 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.344(3) . ?
N1 C7 1.340(3) . ?
N1 C8 1.457(3) . ?
N2 N3 1.320(3) . ?
N3 N4 1.332(3) . ?
N4 C7 1.333(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.379(4) . ?
C1 C7 1.457(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(4) . ?
C6 H6 0.9300 . ?
C8 C9 1.380(4) . ?
C8 C13 1.380(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(4) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 123.1(2) . . ?
C7 N1 N2 108.7(2) . . ?
C7 N1 C8 128.2(2) . . ?
N3 N2 N1 105.5(2) . . ?
N2 N3 N4 111.5(2) . . ?
N3 N4 C7 105.9(2) . . ?
C2 C1 C7 119.6(2) . . ?
C6 C1 C2 120.2(3) . . ?
C6 C1 C7 120.2(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N1 C7 C1 127.2(2) . . ?
N4 C7 N1 108.4(2) . . ?
N4 C7 C1 124.3(2) . . ?
C9 C8 N1 118.8(2) . . ?
C13 C8 N1 120.1(2) . . ?
C13 C8 C9 121.0(2) . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 120.4 . . ?
C12 C13 C8 119.2(3) . . ?
C12 C13 H13 120.4 . . ?

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 N2 N3 N4 -0.1(3) . . . . ?
N1 C8 C9 C10 -180.0(2) . . . . ?
N1 C8 C13 C12 179.9(2) . . . . ?
N2 N1 C7 N4 -0.1(3) . . . . ?
N2 N1 C7 C1 -176.3(2) . . . . ?
N2 N1 C8 C9 57.3(3) . . . . ?
N2 N1 C8 C13 -121.7(3) . . . . ?
N2 N3 N4 C7 0.0(3) . . . . ?
N3 N4 C7 N1 0.0(3) . . . . ?
N3 N4 C7 C1 176.3(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
C2 C1 C7 N1 52.6(4) . . . . ?
C2 C1 C7 N4 -123.0(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C6 C1 C7 N1 -127.4(3) . . . . ?
C6 C1 C7 N4 57.0(4) . . . . ?
C7 N1 N2 N3 0.1(3) . . . . ?
C7 N1 C8 C9 -125.3(3) . . . . ?
C7 N1 C8 C13 55.7(4) . . . . ?
C7 C1 C2 C3 -179.3(2) . . . . ?
C7 C1 C6 C5 179.2(2) . . . . ?
C8 N1 N2 N3 177.9(2) . . . . ?
C8 N1 C7 N4 -177.7(2) . . . . ?
C8 N1 C7 C1 6.1(4) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C9 C8 C13 C12 0.8(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C13 C8 C9 C10 -0.9(4) . . . . ?

_olex2_date_sample_data_collection 2018-05-29
_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_lilh_416_3n3
_database_code_depnum_ccdc_archive 'CCDC 1852261'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_audit_creation_date             2018-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H19 N5'
_chemical_formula_sum            'C11 H19 N5'
_chemical_formula_weight         221.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.8335(13)
_cell_length_b                   9.1979(15)
_cell_length_c                   10.0075(17)
_cell_angle_alpha                94.814(14)
_cell_angle_beta                 103.101(15)
_cell_angle_gamma                96.922(14)
_cell_volume                     604.14(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    802
_cell_measurement_temperature    292.55(10)
_cell_measurement_theta_max      24.1110
_cell_measurement_theta_min      4.0740
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3965
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.55
_diffrn_ambient_temperature      292.55(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -60.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  178.0000  120.0000 18

#__ type_ start__ end____ width___ exp.time_
  2 omega -101.00  -59.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  178.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   25.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  -99.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   42.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -57.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   52.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -77.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega  -43.00   98.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430    0.0000  -30.0000 94
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0651268000
_diffrn_orient_matrix_UB_12      -0.0269174000
_diffrn_orient_matrix_UB_13      0.0552556000
_diffrn_orient_matrix_UB_21      -0.0855843000
_diffrn_orient_matrix_UB_22      -0.0386824000
_diffrn_orient_matrix_UB_23      0.0170626000
_diffrn_orient_matrix_UB_31      0.0055574000
_diffrn_orient_matrix_UB_32      -0.0624060000
_diffrn_orient_matrix_UB_33      -0.0449705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1526
_reflns_number_total             2371
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.179
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.068
_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)+(0.0629P)²+0.0924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1699
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H9AA(0.4) H9AB(0.4) H9BC(0.6) H9BD(0.6) C10(0.4) H10A(0.4)
 H10B(0.4) C10'(0.6) H10C(0.6) H10D(0.6)
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B),
 C9(H9AA,H9AB), C9(H9BC,H9BD), C10(H10A,H10B), C10'(H10C,H10D)
;
_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
N1 N 0.4366(3) 0.6960(2) 0.44246(18) 0.0436(5) Uani 1 d . . .
N2 N 0.5793(3) 0.6716(3) 0.3703(2) 0.0603(6) Uani 1 d . . .
N3 N 0.7436(3) 0.6609(2) 0.4602(2) 0.0613(6) Uani 1 d . . .
N4 N 0.7177(3) 0.6774(2) 0.5904(2) 0.0529(6) Uani 1 d . . .
N5 N 0.4448(3) 0.7305(2) 0.68537(18) 0.0516(6) Uani 1 d B . .
C1 C 0.2395(3) 0.7342(2) 0.3708(2) 0.0428(6) Uani 1 d . . .
H1 H 0.1382 0.6997 0.4208 0.051 Uiso 1 calc . . R
C2 C 0.2513(4) 0.9009(3) 0.3745(3) 0.0560(7) Uani 1 d . . .
H2A H 0.3566 0.9385 0.3305 0.067 Uiso 1 calc . . R
H2B H 0.2868 0.9456 0.4697 0.067 Uiso 1 calc . . R
C3 C 0.0487(4) 0.9422(3) 0.3002(3) 0.0659(8) Uani 1 d . . .
H3A H -0.0531 0.9145 0.3506 0.079 Uiso 1 calc . . R
H3B H 0.0618 1.0481 0.2982 0.079 Uiso 1 calc . . R
C4 C -0.0199(5) 0.8656(3) 0.1534(3) 0.0704(8) Uani 1 d . . .
H4A H -0.1524 0.8897 0.1103 0.084 Uiso 1 calc . . R
H4B H 0.0748 0.9007 0.1002 0.084 Uiso 1 calc . . R
C5 C -0.0313(4) 0.7007(3) 0.1525(2) 0.0589(7) Uani 1 d . . .
H5A H -0.0703 0.6543 0.0578 0.071 Uiso 1 calc . . R
H5B H -0.1345 0.6648 0.1989 0.071 Uiso 1 calc . . R
C6 C 0.1725(4) 0.6584(3) 0.2246(2) 0.0537(7) Uani 1 d . . .
H6A H 0.1599 0.5523 0.2259 0.064 Uiso 1 calc . . R
H6B H 0.2738 0.6870 0.1740 0.064 Uiso 1 calc . . R
C7 C 0.5261(3) 0.7005(2) 0.5775(2) 0.0405(5) Uani 1 d . . .
C8 C 0.2307(4) 0.7046(3) 0.6862(2) 0.0538(7) Uani 1 d B . .
H8A H 0.1681 0.6074 0.6406 0.065 Uiso 1 calc . . R
H8B H 0.1581 0.7780 0.6406 0.065 Uiso 1 calc . . R
C9 C 0.2318(5) 0.7168(4) 0.8372(3) 0.0783(9) Uani 1 d . . .
H9AA H 0.2152 0.8159 0.8695 0.094 Uiso 0.40 calc A 1 R
H9AB H 0.1223 0.6482 0.8532 0.094 Uiso 0.40 calc A 1 R
H9BC H 0.1301 0.7757 0.8553 0.094 Uiso 0.60 calc A 2 R
H9BD H 0.2019 0.6197 0.8652 0.094 Uiso 0.60 calc A 2 R
C11 C 0.5730(5) 0.7320(6) 0.8254(3) 0.0815(11) Uani 1 d . . .
H11A H 0.694(6) 0.817(4) 0.838(3) 0.123(14) Uiso 1 d . . .
H11B H 0.629(7) 0.654(5) 0.836(4) 0.16(2) Uiso 1 d . . .
C10 C 0.4267(14) 0.6816(12) 0.9088(9) 0.071(2) Uani 0.40 d B 1 .
H10A H 0.4199 0.5763 0.9141 0.085 Uiso 0.40 calc B 1 R
H10B H 0.4679 0.7326 1.0017 0.085 Uiso 0.40 calc B 1 R
C10' C 0.4324(9) 0.7863(8) 0.9128(6) 0.0777(17) Uani 0.60 d B 2 .
H10C H 0.4661 0.7557 1.0048 0.093 Uiso 0.60 calc B 2 R
H10D H 0.4417 0.8928 0.9205 0.093 Uiso 0.60 calc B 2 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 N2 1.367(3) . ?
N1 C1 1.473(3) . ?
N1 C7 1.346(3) . ?
N2 N3 1.290(3) . ?
N3 N4 1.353(3) . ?
N4 C7 1.330(3) . ?
N5 C7 1.346(3) . ?
N5 C8 1.456(3) . ?
N5 C11 1.472(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.522(3) . ?
C1 C6 1.512(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.524(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.520(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.509(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.528(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.504(3) . ?
C9 H9AA 0.9700 . ?
C9 H9AB 0.9700 . ?
C9 H9BC 0.9700 . ?
C9 H9BD 0.9700 . ?
C9 C10 1.450(8) . ?
C9 C10' 1.448(6) . ?
C11 H11A 1.05(4) . ?
C11 H11B 0.86(4) . ?
C11 C10 1.497(10) . ?
C11 C10' 1.537(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?

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 N1 C1 120.00(17) . . ?
C7 N1 N2 107.30(18) . . ?
C7 N1 C1 131.86(17) . . ?
N3 N2 N1 106.62(19) . . ?
N2 N3 N4 111.53(19) . . ?
C7 N4 N3 105.58(19) . . ?
C7 N5 C8 126.67(19) . . ?
C7 N5 C11 118.0(2) . . ?
C8 N5 C11 110.6(2) . . ?
N1 C1 H1 108.0 . . ?
N1 C1 C2 109.91(18) . . ?
N1 C1 C6 111.22(17) . . ?
C2 C1 H1 108.0 . . ?
C6 C1 H1 108.0 . . ?
C6 C1 C2 111.61(19) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.56(19) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.3(2) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.7(2) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.2(2) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C1 C6 C5 110.11(18) . . ?
C1 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
N4 C7 N1 109.0(2) . . ?
N4 C7 N5 123.6(2) . . ?
N5 C7 N1 127.32(19) . . ?
N5 C8 H8A 111.0 . . ?
N5 C8 H8B 111.0 . . ?
N5 C8 C9 103.9(2) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
C8 C9 H9AA 110.5 . . ?
C8 C9 H9AB 110.5 . . ?
C8 C9 H9BC 110.3 . . ?
C8 C9 H9BD 110.3 . . ?
H9AA C9 H9AB 108.6 . . ?
H9AA C9 H9BC 37.9 . . ?
H9AA C9 H9BD 135.0 . . ?
H9AB C9 H9BC 73.8 . . ?
H9AB C9 H9BD 37.5 . . ?
H9BC C9 H9BD 108.5 . . ?
C10 C9 C8 106.4(4) . . ?
C10 C9 H9AA 110.5 . . ?
C10 C9 H9AB 110.5 . . ?
C10 C9 H9BC 138.6 . . ?
C10 C9 H9BD 75.1 . . ?
C10' C9 C8 107.3(3) . . ?
C10' C9 H9AA 74.6 . . ?
C10' C9 H9AB 137.5 . . ?
C10' C9 H9BC 110.3 . . ?
C10' C9 H9BD 110.3 . . ?
C10' C9 C10 38.5(4) . . ?
N5 C11 H11A 107(2) . . ?
N5 C11 H11B 113(3) . . ?
N5 C11 C10 104.3(4) . . ?
N5 C11 C10' 100.5(3) . . ?
H11A C11 H11B 105(4) . . ?
C10 C11 H11A 135(2) . . ?
C10 C11 H11B 91(3) . . ?
C10 C11 C10' 36.7(4) . . ?
C10' C11 H11A 106(2) . . ?
C10' C11 H11B 124(3) . . ?
C9 C10 C11 105.7(5) . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C9 C10' C11 103.8(4) . . ?
C9 C10' H10C 111.0 . . ?
C9 C10' H10D 111.0 . . ?
C11 C10' H10C 111.0 . . ?
C11 C10' H10D 111.0 . . ?
H10C C10' H10D 109.0 . . ?

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
N1 N2 N3 N4 -0.1(3) . . . . ?
N1 C1 C2 C3 179.8(2) . . . . ?
N1 C1 C6 C5 -179.6(2) . . . . ?
N2 N1 C1 C2 -90.6(2) . . . . ?
N2 N1 C1 C6 33.6(3) . . . . ?
N2 N1 C7 N4 -1.0(3) . . . . ?
N2 N1 C7 N5 175.9(2) . . . . ?
N2 N3 N4 C7 -0.5(3) . . . . ?
N3 N4 C7 N1 0.9(3) . . . . ?
N3 N4 C7 N5 -176.1(2) . . . . ?
N5 C8 C9 C10 -25.3(5) . . . . ?
N5 C8 C9 C10' 15.1(4) . . . . ?
N5 C11 C10 C9 -24.5(7) . . . . ?
N5 C11 C10' C9 36.8(6) . . . . ?
C1 N1 N2 N3 171.36(19) . . . . ?
C1 N1 C7 N4 -170.1(2) . . . . ?
C1 N1 C7 N5 6.7(4) . . . . ?
C1 C2 C3 C4 -55.3(3) . . . . ?
C2 C1 C6 C5 -56.4(3) . . . . ?
C2 C3 C4 C5 56.1(3) . . . . ?
C3 C4 C5 C6 -56.9(3) . . . . ?
C4 C5 C6 C1 57.0(3) . . . . ?
C6 C1 C2 C3 55.9(3) . . . . ?
C7 N1 N2 N3 0.7(3) . . . . ?
C7 N1 C1 C2 77.5(3) . . . . ?
C7 N1 C1 C6 -158.4(2) . . . . ?
C7 N5 C8 C9 164.6(2) . . . . ?
C7 N5 C11 C10 -148.6(5) . . . . ?
C7 N5 C11 C10' 174.0(3) . . . . ?
C8 N5 C7 N1 27.9(4) . . . . ?
C8 N5 C7 N4 -155.7(2) . . . . ?
C8 N5 C11 C10 8.7(6) . . . . ?
C8 N5 C11 C10' -28.7(5) . . . . ?
C8 C9 C10 C11 31.2(7) . . . . ?
C8 C9 C10' C11 -32.7(5) . . . . ?
C11 N5 C7 N1 -178.9(3) . . . . ?
C11 N5 C7 N4 -2.5(4) . . . . ?
C11 N5 C8 C9 9.7(3) . . . . ?
C10 C9 C10' C11 62.0(7) . . . . ?
C10 C11 C10' C9 -63.0(7) . . . . ?
C10' C9 C10 C11 -66.2(8) . . . . ?
C10' C11 C10 C9 63.9(6) . . . . ?

_olex2_date_sample_data_collection 2018-05-07
_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_lilh_0507
_database_code_depnum_ccdc_archive 'CCDC 1852262'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_audit_creation_date             2018-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H15 N5'
_chemical_formula_sum            'C13 H15 N5'
_chemical_formula_weight         241.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.0745(8)
_cell_length_b                   9.2802(7)
_cell_length_c                   11.0512(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.656(5)
_cell_angle_gamma                90.00
_cell_volume                     1229.98(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.5720
_cell_measurement_theta_min      4.0460
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4342
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_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  -99.00  -60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000    0.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000    0.0000 117
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0111350000
_diffrn_orient_matrix_UB_12      -0.0577031000
_diffrn_orient_matrix_UB_13      0.0389164000
_diffrn_orient_matrix_UB_21      -0.0045885000
_diffrn_orient_matrix_UB_22      0.0496403000
_diffrn_orient_matrix_UB_23      0.0479534000
_diffrn_orient_matrix_UB_31      -0.0579006000
_diffrn_orient_matrix_UB_32      0.0071860000
_diffrn_orient_matrix_UB_33      -0.0189690000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1913
_reflns_number_total             2421
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.140
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.116
_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)+(0.0350P)²+0.3021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1112
_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    
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C11(H11A,H11B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C7(H7), C5(H5), C2(H2), C4(H4), C3(H3)
;
_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
N1 N 0.36379(11) 0.12040(15) 0.58560(12) 0.0294(3) Uani 1 d . . .
N2 N 0.31608(12) 0.17591(17) 0.47613(13) 0.0380(4) Uani 1 d . . .
N4 N 0.49568(12) 0.22288(17) 0.49611(13) 0.0363(4) Uani 1 d . . .
C9 C 0.47464(13) 0.15044(18) 0.59557(14) 0.0281(4) Uani 1 d . . .
N5 N 0.55163(11) 0.11796(16) 0.68803(13) 0.0319(3) Uani 1 d . . .
C1 C 0.02015(13) -0.1184(2) 0.65655(16) 0.0342(4) Uani 1 d . . .
H1 H 0.0058 -0.1212 0.5721 0.041 Uiso 1 calc . . R
N3 N 0.39559(13) 0.23551(18) 0.42640(13) 0.0416(4) Uani 1 d . . .
C10 C 0.54366(13) 0.00922(19) 0.78339(15) 0.0310(4) Uani 1 d . . .
H10A H 0.5073 -0.0776 0.7499 0.037 Uiso 1 calc . . R
H10B H 0.5029 0.0462 0.8474 0.037 Uiso 1 calc . . R
C6 C 0.11956(13) -0.05734(18) 0.71027(15) 0.0293(4) Uani 1 d . . .
C8 C 0.29629(13) 0.05951(18) 0.66831(15) 0.0298(4) Uani 1 d . . .
H8 H 0.3215 0.0607 0.7511 0.036 Uiso 1 calc . . R
C7 C 0.19834(13) 0.00078(19) 0.63177(15) 0.0311(4) Uani 1 d . . .
H7 H 0.1775 -0.0040 0.5482 0.037 Uiso 1 calc . . R
C5 C 0.13859(14) -0.0556(2) 0.83746(16) 0.0349(4) Uani 1 d . . .
H5 H 0.2037 -0.0145 0.8757 0.042 Uiso 1 calc . . R
C2 C -0.05726(14) -0.1746(2) 0.72609(17) 0.0398(5) Uani 1 d . . .
H2 H -0.1234 -0.2136 0.6885 0.048 Uiso 1 calc . . R
C12 C 0.72443(15) 0.1203(2) 0.80654(18) 0.0421(5) Uani 1 d . . .
H12A H 0.7156 0.1911 0.8693 0.051 Uiso 1 calc . . R
H12B H 0.8033 0.1043 0.8025 0.051 Uiso 1 calc . . R
C11 C 0.66546(14) -0.0195(2) 0.83080(17) 0.0384(5) Uani 1 d . . .
H11A H 0.6735 -0.0414 0.9172 0.046 Uiso 1 calc . . R
H11B H 0.6949 -0.0991 0.7875 0.046 Uiso 1 calc . . R
C13 C 0.66635(13) 0.1684(2) 0.68431(17) 0.0374(4) Uani 1 d . . .
H13A H 0.6690 0.2724 0.6759 0.045 Uiso 1 calc . . R
H13B H 0.6997 0.1241 0.6177 0.045 Uiso 1 calc . . R
C4 C 0.06215(14) -0.1139(2) 0.90669(17) 0.0406(5) Uani 1 d . . .
H4 H 0.0767 -0.1136 0.9912 0.049 Uiso 1 calc . . R
C3 C -0.03630(15) -0.1730(2) 0.85137(17) 0.0420(5) Uani 1 d . . .
H3 H -0.0881 -0.2113 0.8986 0.050 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3781(18) . ?
N1 C9 1.359(2) . ?
N1 C8 1.411(2) . ?
N2 N3 1.285(2) . ?
N4 C9 1.338(2) . ?
N4 N3 1.361(2) . ?
C9 N5 1.334(2) . ?
N5 C10 1.470(2) . ?
N5 C13 1.467(2) . ?
C1 H1 0.9300 . ?
C1 C6 1.396(2) . ?
C1 C2 1.380(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.526(2) . ?
C6 C7 1.463(2) . ?
C6 C5 1.398(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.322(2) . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.376(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.519(3) . ?
C12 C13 1.515(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C3 1.385(3) . ?
C3 H3 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 N1 C8 120.27(13) . . ?
C9 N1 N2 107.58(13) . . ?
C9 N1 C8 131.82(14) . . ?
N3 N2 N1 106.21(13) . . ?
C9 N4 N3 105.52(14) . . ?
N4 C9 N1 108.39(14) . . ?
N5 C9 N1 127.46(15) . . ?
N5 C9 N4 124.14(15) . . ?
C9 N5 C10 127.34(14) . . ?
C9 N5 C13 118.87(14) . . ?
C13 N5 C10 112.31(13) . . ?
C6 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C2 C1 C6 121.42(16) . . ?
N2 N3 N4 112.29(14) . . ?
N5 C10 H10A 111.2 . . ?
N5 C10 H10B 111.2 . . ?
N5 C10 C11 103.01(13) . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
C1 C6 C7 118.91(15) . . ?
C1 C6 C5 117.74(16) . . ?
C5 C6 C7 123.34(15) . . ?
N1 C8 H8 119.0 . . ?
C7 C8 N1 122.04(15) . . ?
C7 C8 H8 119.0 . . ?
C6 C7 H7 116.9 . . ?
C8 C7 C6 126.23(16) . . ?
C8 C7 H7 116.9 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.78(16) . . ?
C4 C5 H5 119.6 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.86(16) . . ?
C3 C2 H2 120.1 . . ?
H12A C12 H12B 109.1 . . ?
C11 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
C13 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
C13 C12 C11 103.36(14) . . ?
C10 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C12 C11 C10 104.08(14) . . ?
C12 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
H11A C11 H11B 109.0 . . ?
N5 C13 C12 102.82(14) . . ?
N5 C13 H13A 111.2 . . ?
N5 C13 H13B 111.2 . . ?
C12 C13 H13A 111.2 . . ?
C12 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.45(17) . . ?
C3 C4 H4 119.8 . . ?
C2 C3 C4 119.74(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?

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 N2 N3 N4 0.4(2) . . . . ?
N1 C9 N5 C10 18.9(3) . . . . ?
N1 C9 N5 C13 -176.16(16) . . . . ?
N1 C8 C7 C6 -176.19(16) . . . . ?
N2 N1 C9 N4 0.28(18) . . . . ?
N2 N1 C9 N5 179.00(17) . . . . ?
N2 N1 C8 C7 27.5(2) . . . . ?
N4 C9 N5 C10 -162.60(16) . . . . ?
N4 C9 N5 C13 2.4(3) . . . . ?
C9 N1 N2 N3 -0.39(18) . . . . ?
C9 N1 C8 C7 -159.89(17) . . . . ?
C9 N4 N3 N2 -0.2(2) . . . . ?
C9 N5 C10 C11 159.19(17) . . . . ?
C9 N5 C13 C12 176.03(16) . . . . ?
N5 C10 C11 C12 27.45(18) . . . . ?
C1 C6 C7 C8 -178.79(17) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
N3 N4 C9 N1 -0.07(18) . . . . ?
N3 N4 C9 N5 -178.84(16) . . . . ?
C10 N5 C13 C12 -16.84(19) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C5 C4 C3 -1.3(3) . . . . ?
C8 N1 N2 N3 173.87(15) . . . . ?
C8 N1 C9 N4 -173.06(17) . . . . ?
C8 N1 C9 N5 5.7(3) . . . . ?
C7 C6 C5 C4 -178.99(17) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
C2 C1 C6 C7 -179.91(17) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C11 C12 C13 N5 33.36(19) . . . . ?
C13 N5 C10 C11 -6.60(19) . . . . ?
C13 C12 C11 C10 -38.21(19) . . . . ?

_olex2_date_sample_data_collection 2018-05-07
_olex2_submission_special_instructions 'No special instructions were received'
