# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

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

data_UMV_14
_audit_block_doi                 10.5517/ccdc.csd.cc1p0sq6
_database_code_depnum_ccdc_archive 'CCDC 1549898'
_audit_update_record             
;
2017-05-13 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;
_audit_creation_date             2015-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_systematic        
1'-((1-benzyl-1H-tetrazol-5-yl)methyl)spiro[indoline-3,3'-pyrrolidin]-2-one
_chemical_formula_moiety         'C20 H20 N6 O'
_chemical_formula_sum            'C20 H20 N6 O'
_chemical_formula_weight         360.42
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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

_symmetry_Int_Tables_number      14
_cell_length_a                   17.3115(8)
_cell_length_b                   6.3966(2)
_cell_length_c                   18.3592(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.585(6)
_cell_angle_gamma                90
_cell_volume                     1890.43(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9584
_cell_measurement_temperature    298.5
_cell_measurement_theta_max      26.3680
_cell_measurement_theta_min      3.7640
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2663
_exptl_crystal_F_000             760.2807
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.052
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34648
_diffrn_reflns_theta_full        29.6320
_diffrn_reflns_theta_max         29.63
_diffrn_reflns_theta_min         3.40
_diffrn_ambient_temperature      298.5
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0945
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9110
_diffrn_measured_fraction_theta_max 0.9071
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   83.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   57.0000   90.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   70.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   57.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega   28.00   54.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  -99.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   40.00   74.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   57.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   34.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  -99.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega  -20.00   55.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  -99.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
  7 omega   -3.00   85.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   37.0000   30.0000 88

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   88.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  178.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega  -11.00   83.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070   77.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
 10 omega  -11.00   60.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070 -109.0000 -159.0000 71

#__ type_ start__ end____ width___ exp.time_
 11 omega  -53.00   35.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -       15.8070  -37.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
 12 omega  -85.00   -1.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -      -17.5258  -57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
 13 omega  -47.00    6.00   1.0000   18.2400
omega____ theta____ kappa____ phi______ frames
    -      -17.5258   19.0000  150.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0325706000
_diffrn_orient_matrix_UB_12      -0.0034728000
_diffrn_orient_matrix_UB_13      -0.0146922000
_diffrn_orient_matrix_UB_21      -0.0291084000
_diffrn_orient_matrix_UB_22      -0.0253401000
_diffrn_orient_matrix_UB_23      -0.0377249000
_diffrn_orient_matrix_UB_31      -0.0057861000
_diffrn_orient_matrix_UB_32      0.1079002000
_diffrn_orient_matrix_UB_33      -0.0093346000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              -23
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                3554
_reflns_number_total             4822
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.8362
_refine_diff_density_min         -0.3046
_refine_diff_density_rms         0.0729
_refine_ls_d_res_high            0.7187
_refine_ls_d_res_low             5.9899
_refine_ls_goodness_of_fit_ref   1.0505
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4822
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      1.0505
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0976P)²+1.5727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2133
_refine_ls_wR_factor_ref         0.2298
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b), C20(H20a,H20b)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C22(H22), C23(H23), C24(H24), C26(H26)
;
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_refinement_flags_posn
O27 O 0.43088(14) 1.2757(4) 0.49429(13) 0.0681(6) Uani 1.000000 .
N1 N 0.45941(13) 1.4350(3) 0.39471(14) 0.0544(6) Uani 1.000000 .
H1 H 0.49856(13) 1.5168(3) 0.42262(14) 0.0653(7) Uiso 1.000000 R
N10 N 0.23421(11) 0.9829(3) 0.31799(11) 0.0389(4) Uani 1.000000 .
N15 N 0.06897(12) 0.7749(3) 0.19866(12) 0.0430(5) Uani 1.000000 .
N17 N 0.11034(14) 0.5589(4) 0.29503(15) 0.0554(6) Uani 1.000000 .
N18 N 0.06303(17) 0.4591(4) 0.22830(18) 0.0642(7) Uani 1.000000 .
N19 N 0.03770(15) 0.5866(4) 0.16996(16) 0.0586(6) Uani 1.000000 .
C2 C 0.42032(15) 1.2976(4) 0.42476(17) 0.0488(6) Uani 1.000000 .
C3 C 0.35797(14) 1.1743(4) 0.35706(15) 0.0429(6) Uani 1.000000 .
C4 C 0.36599(14) 1.2792(4) 0.28710(16) 0.0452(6) Uani 1.000000 .
C5 C 0.32617(18) 1.2475(5) 0.20752(18) 0.0600(7) Uani 1.000000 .
H5 H 0.28425(18) 1.1481(5) 0.18911(18) 0.0720(9) Uiso 1.000000 R
C6 C 0.3492(2) 1.3655(6) 0.1551(2) 0.0730(9) Uani 1.000000 .
H6 H 0.3226(2) 1.3446(6) 0.1015(2) 0.0876(11) Uiso 1.000000 R
C7 C 0.4113(2) 1.5130(6) 0.1822(2) 0.0692(8) Uani 1.000000 .
H7 H 0.427(2) 1.599(6) 0.146(2) 0.0830(10) Uiso 1.000000 R
C8 C 0.45192(18) 1.5465(4) 0.2610(2) 0.0600(8) Uani 1.000000 .
H8 H 0.49395(18) 1.6458(4) 0.2791(2) 0.0720(9) Uiso 1.000000 R
C9 C 0.42879(15) 1.4296(4) 0.31225(17) 0.0472(6) Uani 1.000000 .
C11 C 0.29899(16) 0.8243(4) 0.3479(2) 0.0612(8) Uani 1.000000 .
H11a H 0.29794(16) 0.7634(4) 0.3959(2) 0.0735(10) Uiso 1.000000 R
H11b H 0.29139(16) 0.7138(4) 0.3097(2) 0.0735(10) Uiso 1.000000 R
C12 C 0.37954(15) 0.9372(4) 0.36295(18) 0.0517(7) Uani 1.000000 .
H12a H 0.40286(15) 0.8985(4) 0.32423(18) 0.0620(8) Uiso 1.000000 R
H12b H 0.41944(15) 0.9034(4) 0.41460(18) 0.0620(8) Uiso 1.000000 R
C13 C 0.27097(14) 1.1731(4) 0.36006(16) 0.0457(6) Uani 1.000000 .
H13a H 0.23969(14) 1.2955(4) 0.33440(16) 0.0548(7) Uiso 1.000000 R
H13b H 0.27349(14) 1.1683(4) 0.41369(16) 0.0548(7) Uiso 1.000000 R
C14 C 0.15676(15) 0.9292(4) 0.32799(15) 0.0458(6) Uani 1.000000 .
H14a H 0.16866(15) 0.8884(4) 0.38193(15) 0.0549(7) Uiso 1.000000 R
H14b H 0.12086(15) 1.0509(4) 0.31690(15) 0.0549(7) Uiso 1.000000 R
C16 C 0.11326(13) 0.7556(4) 0.27523(14) 0.0406(5) Uani 1.000000 .
C20 C 0.05313(18) 0.9583(4) 0.14827(16) 0.0537(7) Uani 1.000000 .
H20a H -0.00465(18) 0.9572(4) 0.11323(16) 0.0644(8) Uiso 1.000000 R
H20b H 0.06195(18) 1.0827(4) 0.18055(16) 0.0644(8) Uiso 1.000000 R
C21 C 0.10713(17) 0.9710(4) 0.10009(14) 0.0492(6) Uani 1.000000 .
C22 C 0.1610(2) 0.8158(5) 0.0976(2) 0.0677(8) Uani 1.000000 .
H22 H 0.1655(2) 0.6949(5) 0.1271(2) 0.0812(10) Uiso 1.000000 R
C23 C 0.2089(3) 0.8374(6) 0.0515(2) 0.0839(11) Uani 1.000000 .
H23 H 0.2457(3) 0.7322(6) 0.0509(2) 0.1007(13) Uiso 1.000000 R
C24 C 0.2018(3) 1.0113(7) 0.0076(2) 0.0847(11) Uani 1.000000 .
H24 H 0.2333(3) 1.0248(7) -0.0237(2) 0.1016(14) Uiso 1.000000 R
C25 C 0.1491(3) 1.1656(7) 0.0093(2) 0.0834(12) Uani 1.000000 .
H25 H 0.142(3) 1.282(7) -0.019(3) 0.1001(15) Uiso 1.000000 R
C26 C 0.1019(2) 1.1484(5) 0.05603(19) 0.0686(9) Uani 1.000000 .
H26 H 0.0668(2) 1.2568(5) 0.05755(19) 0.0823(10) Uiso 1.000000 R


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
O27 C2 1.229(3) . ?
N1 C2 1.345(4) . ?
N1 C9 1.408(4) . ?
N10 C11 1.461(3) . ?
N10 C13 1.456(3) . ?
N10 C14 1.460(3) . ?
N15 N19 1.346(3) . ?
N15 C16 1.337(3) . ?
N15 C20 1.457(3) . ?
N17 N18 1.357(4) . ?
N17 C16 1.316(3) . ?
N18 N19 1.288(4) . ?
C2 C3 1.531(3) . ?
C3 C4 1.500(4) . ?
C3 C12 1.556(3) . ?
C3 C13 1.527(3) . ?
C4 C5 1.382(4) . ?
C4 C9 1.397(3) . ?
C5 C6 1.392(5) . ?
C6 C7 1.378(5) . ?
C7 C8 1.373(5) . ?
C8 C9 1.372(4) . ?
C11 C12 1.503(4) . ?
C14 C16 1.484(3) . ?
C20 C21 1.507(4) . ?
C21 C22 1.375(4) . ?
C21 C26 1.377(4) . ?
C22 C23 1.393(5) . ?
C23 C24 1.353(6) . ?
C24 C25 1.353(6) . ?
C25 C26 1.389(5) . ?

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
C9 N1 C2 112.2(2) . . ?
C13 N10 C11 104.79(19) . . ?
C14 N10 C11 113.7(2) . . ?
C14 N10 C13 111.86(18) . . ?
C16 N15 N19 108.8(2) . . ?
C20 N15 N19 121.2(2) . . ?
C20 N15 C16 130.1(2) . . ?
C16 N17 N18 105.8(2) . . ?
N19 N18 N17 111.2(2) . . ?
N18 N19 N15 106.0(2) . . ?
N1 C2 O27 126.5(2) . . ?
C3 C2 O27 125.1(3) . . ?
C3 C2 N1 108.3(2) . . ?
C4 C3 C2 101.8(2) . . ?
C12 C3 C2 111.5(2) . . ?
C12 C3 C4 113.6(2) . . ?
C13 C3 C2 112.5(2) . . ?
C13 C3 C4 115.9(2) . . ?
C13 C3 C12 101.94(19) . . ?
C5 C4 C3 132.2(2) . . ?
C9 C4 C3 109.3(2) . . ?
C9 C4 C5 118.4(3) . . ?
C6 C5 C4 119.5(3) . . ?
C7 C6 C5 120.4(3) . . ?
C8 C7 C6 121.1(3) . . ?
C9 C8 C7 118.2(3) . . ?
C4 C9 N1 108.1(2) . . ?
C8 C9 N1 129.4(2) . . ?
C8 C9 C4 122.5(3) . . ?
C12 C11 N10 105.5(2) . . ?
C11 C12 C3 105.83(19) . . ?
C3 C13 N10 103.27(18) . . ?
C16 C14 N10 111.28(19) . . ?
N17 C16 N15 108.3(2) . . ?
C14 C16 N15 125.1(2) . . ?
C14 C16 N17 126.7(2) . . ?
C21 C20 N15 113.8(2) . . ?
C22 C21 C20 123.7(3) . . ?
C26 C21 C20 117.9(3) . . ?
C26 C21 C22 118.3(3) . . ?
C23 C22 C21 120.7(3) . . ?
C24 C23 C22 120.0(4) . . ?
C25 C24 C23 120.0(4) . . ?
C26 C25 C24 120.8(4) . . ?
C25 C26 C21 120.1(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O27 0.8600 2.052(3) 2.887(3) 163.59(10) 3_686

_olex2_date_sample_data_collection 2015-08-25
_olex2_submission_original_sample_id UMV14
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_melting_point          201-203
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hex-AcOEt (1/1 v/v)'
####################################################################### 
# 
# 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_srl272-na160
_audit_block_doi                 10.5517/ccdc.csd.cc1p0wq9
_database_code_depnum_ccdc_archive 'CCDC 1549991'
_audit_update_record             
;
2017-05-13 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;
_audit_creation_date             2015-08-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
2-((1-(2,6-dimethylphenyl)-1H-tetrazol-5-yl)methyl)-2,3,4,9-tetrahydro-1H-2l4-pyrido[3,4-b]indole
_chemical_formula_moiety         'C21 H23 N6'
_chemical_formula_sum            'C21 H23 N6'
_chemical_formula_weight         359.45
_chemical_melting_point          467-469
_chemical_oxdiff_formula         'C21 H22 N6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.22814(16)
_cell_length_b                   32.2130(5)
_cell_length_c                   7.46549(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.201(2)
_cell_angle_gamma                90.00
_cell_volume                     1868.67(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11899
_cell_measurement_temperature    294
_cell_measurement_theta_max      76.6070
_cell_measurement_theta_min      4.0610
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            39099
_diffrn_reflns_theta_full        77.54
_diffrn_reflns_theta_max         77.54
_diffrn_reflns_theta_min         5.49
_diffrn_ambient_temperature      294
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3659
_diffrn_detector_type            Atlas
_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  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000   60.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega -117.00  -18.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -38.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
  6 omega -115.00  -60.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574 -146.0000  163.0000 55

#__ type_ start__ end____ width___ exp.time_
  7 omega   57.00  131.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -       42.3574  178.0000    0.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega   -4.00   83.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -       42.3574  -99.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
  9 omega   94.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  125.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
 10 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000   30.0000 78

#__ type_ start__ end____ width___ exp.time_
 13 omega   86.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
 14 omega   41.00  121.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00  121.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
 16 omega   86.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
 17 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
 18 omega   41.00  121.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 19 omega   38.00   91.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -30.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
 20 omega   88.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 21 omega   41.00   98.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
 22 omega   41.00  121.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000 -125.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
 23 omega   42.00  143.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -61.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 24 omega   41.00   98.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -45.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
 25 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
 26 omega   31.00  109.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000  -94.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
 27 omega   85.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
 28 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000  -90.0000 109

#__ type_ start__ end____ width___ exp.time_
 29 omega  -50.00   32.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574   38.0000 -150.0000 82

#__ type_ start__ end____ width___ exp.time_
 30 omega -115.00  -14.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -57.0000  150.0000 101

#__ type_ start__ end____ width___ exp.time_
 31 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000  -30.0000 109

#__ type_ start__ end____ width___ exp.time_
 32 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000  150.0000 109

#__ type_ start__ end____ width___ exp.time_
 33 omega -115.00  -14.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -57.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
 34 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000 -180.0000 109

#__ type_ start__ end____ width___ exp.time_
 35 omega -119.00  -10.00   1.0000    3.1050
omega____ theta____ kappa____ phi______ frames
    -      -42.3574  -77.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
 36 omega   85.00  172.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
 37 omega   85.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   61.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
 38 omega   81.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   77.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 39 omega   88.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   45.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
 40 omega   86.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   30.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
 41 omega   61.00  178.00   1.0000   12.4250
omega____ theta____ kappa____ phi______ frames
    -      114.0000   15.0000  120.0000 117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0273632000
_diffrn_orient_matrix_UB_12      0.0471783000
_diffrn_orient_matrix_UB_13      -0.0286497000
_diffrn_orient_matrix_UB_21      0.1949068000
_diffrn_orient_matrix_UB_22      0.0070549000
_diffrn_orient_matrix_UB_23      0.0930786000
_diffrn_orient_matrix_UB_31      0.0238822000
_diffrn_orient_matrix_UB_32      -0.0035312000
_diffrn_orient_matrix_UB_33      -0.1955799000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3450
_reflns_number_total             3980
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0003(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.054
_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)+(0.0724P)²+0.5077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1433
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C22(H22), C23(H23), C24(H24), N11(H11)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_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
C2 C 0.6118(2) 0.08246(5) 0.7511(2) 0.0477(4) Uani 1 d . . .
H2A H 0.6392 0.1106 0.7973 0.057 Uiso 1 calc . . R
H2B H 0.5477 0.0839 0.6165 0.057 Uiso 1 calc . . R
C3 C 0.7786(2) 0.05864(5) 0.7797(2) 0.0485(4) Uani 1 d . . .
H3A H 0.8305 0.0675 0.6867 0.058 Uiso 1 calc . . R
H3B H 0.8592 0.0643 0.9051 0.058 Uiso 1 calc . . R
C4 C 0.74121(19) 0.01327(5) 0.7587(2) 0.0434(3) Uani 1 d . . .
C5 C 0.8455(2) -0.02100(5) 0.7385(2) 0.0450(3) Uani 1 d . . .
C6 C 1.0093(2) -0.02426(6) 0.7225(3) 0.0575(4) Uani 1 d . . .
H6 H 1.0758 -0.0007 0.7267 0.069 Uiso 1 calc . . R
C7 C 1.0706(3) -0.06310(7) 0.7004(3) 0.0668(5) Uani 1 d . . .
H7 H 1.1796 -0.0656 0.6896 0.080 Uiso 1 calc . . R
C8 C 0.9730(3) -0.09856(6) 0.6939(3) 0.0630(5) Uani 1 d . . .
H8 H 1.0188 -0.1243 0.6808 0.076 Uiso 1 calc . . R
C9 C 0.8098(2) -0.09648(5) 0.7064(2) 0.0554(4) Uani 1 d . . .
H9 H 0.7443 -0.1203 0.7003 0.067 Uiso 1 calc . . R
C10 C 0.7465(2) -0.05726(5) 0.7287(2) 0.0447(3) Uani 1 d . . .
C12 C 0.58856(19) -0.00278(5) 0.75839(19) 0.0405(3) Uani 1 d . . .
C13 C 0.44028(19) 0.02199(4) 0.7717(2) 0.0411(3) Uani 1 d . . .
H13A H 0.3547 0.0250 0.6469 0.049 Uiso 1 calc . . R
H13B H 0.3871 0.0080 0.8533 0.049 Uiso 1 calc . . R
C14 C 0.35790(19) 0.08977(5) 0.8410(2) 0.0455(4) Uani 1 d . . .
H14A H 0.2761 0.0745 0.8841 0.055 Uiso 1 calc . . R
H14B H 0.3002 0.0982 0.7108 0.055 Uiso 1 calc . . R
C19 C 0.41671(19) 0.12749(5) 0.9622(2) 0.0435(3) Uani 1 d . . .
C20 C 0.2410(2) 0.18263(5) 0.7393(2) 0.0476(4) Uani 1 d . . .
C21 C 0.0668(2) 0.18146(5) 0.7180(3) 0.0532(4) Uani 1 d . . .
C22 C -0.0471(3) 0.19710(6) 0.5501(3) 0.0650(5) Uani 1 d . . .
H22 H -0.1648 0.1965 0.5302 0.078 Uiso 1 calc . . R
C23 C 0.0125(3) 0.21351(6) 0.4125(3) 0.0719(6) Uani 1 d . . .
H23 H -0.0654 0.2239 0.3010 0.086 Uiso 1 calc . . R
C24 C 0.1859(3) 0.21467(6) 0.4386(3) 0.0678(5) Uani 1 d . . .
H24 H 0.2238 0.2259 0.3445 0.081 Uiso 1 calc . . R
C25 C 0.3054(2) 0.19938(5) 0.6037(3) 0.0556(4) Uani 1 d . . .
C26 C 0.4951(3) 0.20124(7) 0.6334(4) 0.0753(6) Uani 1 d . . .
H26A H 0.5558 0.2097 0.7613 0.113 Uiso 1 calc . . GR
H26B H 0.5159 0.2209 0.5467 0.113 Uiso 1 calc . . GR
H26C H 0.5348 0.1743 0.6112 0.113 Uiso 1 calc . . GR
C27 C 0.0040(3) 0.16480(7) 0.8714(3) 0.0732(6) Uani 1 d . . .
H27A H 0.0298 0.1357 0.8884 0.110 Uiso 1 calc . . GR
H27B H -0.1181 0.1688 0.8360 0.110 Uiso 1 calc . . GR
H27C H 0.0603 0.1792 0.9879 0.110 Uiso 1 calc . . GR
N1 N 0.50335(16) 0.06302(4) 0.84986(18) 0.0412(3) Uani 1 d . . .
H1 H 0.5681 0.0597 0.9739 0.049 Uiso 1 calc . . R
N11 N 0.58873(17) -0.04546(4) 0.73898(18) 0.0452(3) Uani 1 d . . .
H11 H 0.5049 -0.0618 0.7342 0.054 Uiso 1 calc . . R
N15 N 0.36166(17) 0.16643(4) 0.9124(2) 0.0471(3) Uani 1 d . . .
N16 N 0.4417(2) 0.19183(5) 1.0607(2) 0.0618(4) Uani 1 d . . .
N17 N 0.5406(2) 0.16846(5) 1.1920(2) 0.0635(4) Uani 1 d . . .
N18 N 0.52790(19) 0.12809(4) 1.1355(2) 0.0541(4) Uani 1 d . . .


_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
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.525(2) . ?
C2 N1 1.471(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.491(2) . ?
C4 C5 1.436(2) . ?
C4 C12 1.358(2) . ?
C5 C6 1.395(2) . ?
C5 C10 1.412(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.397(2) . ?
C10 N11 1.379(2) . ?
C12 C13 1.488(2) . ?
C12 N11 1.3826(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 N1 1.4689(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C19 1.497(2) . ?
C14 N1 1.4584(19) . ?
C19 N15 1.3437(19) . ?
C19 N18 1.316(2) . ?
C20 C21 1.390(2) . ?
C20 C25 1.396(2) . ?
C20 N15 1.444(2) . ?
C21 C22 1.389(3) . ?
C21 C27 1.502(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.389(3) . ?
C25 C26 1.504(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 H1 0.9100 . ?
N11 H11 0.8600 . ?
N15 N16 1.3601(19) . ?
N16 N17 1.290(2) . ?
N17 N18 1.361(2) . ?

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
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
N1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
N1 C2 C3 112.45(13) . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 109.46(13) . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C5 C4 C3 130.89(14) . . ?
C12 C4 C3 122.16(14) . . ?
C12 C4 C5 106.95(14) . . ?
C6 C5 C4 133.94(16) . . ?
C6 C5 C10 119.34(15) . . ?
C10 C5 C4 106.69(14) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 C5 118.70(18) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.36(18) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.55(17) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 121.2 . . ?
C8 C9 C10 117.51(18) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 C5 121.53(16) . . ?
N11 C10 C5 107.85(13) . . ?
N11 C10 C9 130.59(16) . . ?
C4 C12 C13 125.04(14) . . ?
C4 C12 N11 110.24(13) . . ?
N11 C12 C13 124.70(13) . . ?
C12 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
N1 C13 C12 108.58(12) . . ?
N1 C13 H13A 110.0 . . ?
N1 C13 H13B 110.0 . . ?
H14A C14 H14B 108.1 . . ?
C19 C14 H14A 109.5 . . ?
C19 C14 H14B 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 C19 110.78(12) . . ?
N15 C19 C14 125.30(14) . . ?
N18 C19 C14 125.99(14) . . ?
N18 C19 N15 108.69(14) . . ?
C21 C20 C25 123.40(16) . . ?
C21 C20 N15 118.17(15) . . ?
C25 C20 N15 118.42(15) . . ?
C20 C21 C27 121.53(17) . . ?
C22 C21 C20 117.24(18) . . ?
C22 C21 C27 121.22(18) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.71(19) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.7 . . ?
C24 C23 C22 120.69(19) . . ?
C24 C23 H23 119.7 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 120.97(19) . . ?
C25 C24 H24 119.5 . . ?
C20 C25 C26 122.08(18) . . ?
C24 C25 C20 116.98(18) . . ?
C24 C25 C26 120.94(18) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 C27 H27A 109.5 . . ?
C21 C27 H27B 109.5 . . ?
C21 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 N1 H1 108.2 . . ?
C13 N1 C2 112.14(12) . . ?
C13 N1 H1 108.2 . . ?
C14 N1 C2 110.49(12) . . ?
C14 N1 C13 109.64(11) . . ?
C14 N1 H1 108.2 . . ?
C10 N11 C12 108.26(13) . . ?
C10 N11 H11 125.9 . . ?
C12 N11 H11 125.9 . . ?
C19 N15 C20 130.93(13) . . ?
C19 N15 N16 107.91(13) . . ?
N16 N15 C20 121.16(13) . . ?
N17 N16 N15 106.42(14) . . ?
N16 N17 N18 110.95(14) . . ?
C19 N18 N17 106.03(14) . . ?

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
C2 C3 C4 C5 167.26(15) . . . . ?
C2 C3 C4 C12 -13.7(2) . . . . ?
C3 C2 N1 C13 -65.37(17) . . . . ?
C3 C2 N1 C14 172.00(13) . . . . ?
C3 C4 C5 C6 -3.6(3) . . . . ?
C3 C4 C5 C10 178.61(16) . . . . ?
C3 C4 C12 C13 2.2(2) . . . . ?
C3 C4 C12 N11 -179.33(14) . . . . ?
C4 C5 C6 C7 -178.55(18) . . . . ?
C4 C5 C10 C9 179.27(14) . . . . ?
C4 C5 C10 N11 0.99(17) . . . . ?
C4 C12 C13 N1 -19.43(19) . . . . ?
C4 C12 N11 C10 0.69(17) . . . . ?
C5 C4 C12 C13 -178.50(13) . . . . ?
C5 C4 C12 N11 -0.06(17) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C5 C10 N11 C12 -1.04(17) . . . . ?
C6 C5 C10 C9 1.1(2) . . . . ?
C6 C5 C10 N11 -177.18(14) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C8 C9 C10 C5 -0.2(2) . . . . ?
C8 C9 C10 N11 177.67(16) . . . . ?
C9 C10 N11 C12 -179.10(16) . . . . ?
C10 C5 C6 C7 -1.0(3) . . . . ?
C12 C4 C5 C6 177.22(18) . . . . ?
C12 C4 C5 C10 -0.57(17) . . . . ?
C12 C13 N1 C2 49.44(16) . . . . ?
C12 C13 N1 C14 172.56(12) . . . . ?
C13 C12 N11 C10 179.13(13) . . . . ?
C14 C19 N15 C20 -1.2(3) . . . . ?
C14 C19 N15 N16 178.77(15) . . . . ?
C14 C19 N18 N17 -178.95(16) . . . . ?
C19 C14 N1 C2 -70.28(16) . . . . ?
C19 C14 N1 C13 165.63(13) . . . . ?
C19 N15 N16 N17 0.3(2) . . . . ?
C20 C21 C22 C23 -0.8(3) . . . . ?
C20 N15 N16 N17 -179.70(15) . . . . ?
C21 C20 C25 C24 -1.4(3) . . . . ?
C21 C20 C25 C26 178.27(17) . . . . ?
C21 C20 N15 C19 84.7(2) . . . . ?
C21 C20 N15 N16 -95.34(19) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C20 0.6(3) . . . . ?
C23 C24 C25 C26 -179.07(19) . . . . ?
C25 C20 C21 C22 1.5(3) . . . . ?
C25 C20 C21 C27 -177.31(18) . . . . ?
C25 C20 N15 C19 -96.6(2) . . . . ?
C25 C20 N15 N16 83.4(2) . . . . ?
C27 C21 C22 C23 177.98(19) . . . . ?
N1 C2 C3 C4 43.72(18) . . . . ?
N1 C14 C19 N15 136.74(15) . . . . ?
N1 C14 C19 N18 -44.5(2) . . . . ?
N11 C12 C13 N1 162.36(13) . . . . ?
N15 C19 N18 N17 -0.05(18) . . . . ?
N15 C20 C21 C22 -179.82(15) . . . . ?
N15 C20 C21 C27 1.4(2) . . . . ?
N15 C20 C25 C24 179.95(15) . . . . ?
N15 C20 C25 C26 -0.4(2) . . . . ?
N15 N16 N17 N18 -0.3(2) . . . . ?
N16 N17 N18 C19 0.2(2) . . . . ?
N18 C19 N15 C20 179.85(16) . . . . ?
N18 C19 N15 N16 -0.14(19) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a glass fiber'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hex-AcOEt (7/3 v/v)'
