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

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

data_peru_sm_31_0m
_database_code_depnum_ccdc_archive 'CCDC 1032189'
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2015-09-28 downloaded from the CCDC.
;
_audit_creation_date             2015-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '1,3,4,5-Tetraphenyl-1H-pyrazole '
_chemical_formula_moiety         'C27 H20 N2'
_chemical_formula_sum            'C27 H20 N2'
_chemical_formula_weight         372.45
_chemical_absolute_configuration ?
_chemical_melting_point          475.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.9297(3)
_cell_length_b                   9.6354(3)
_cell_length_c                   10.6037(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.080(2)
_cell_angle_gamma                90
_cell_volume                     1014.53(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6405
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.79
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0930 before and 0.0402 after correction.
The Ratio of minimum to maximum transmission is 0.9131.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20095
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.066
_diffrn_reflns_theta_min         2.808
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                4336
_reflns_number_total             5787
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5787
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.0661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1081
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C17(H17), C15(H15), C9(H9), C12(H12), C21(H21), C20(H20), C11(H11),
 C19(H19), C14(H14), C13(H13), C18(H18), C8(H8), C5(H5), C24(H24), C27(H27),
 C25(H25), C6(H6), C7(H7), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.83904(18) 0.2171(2) 0.24099(18) 0.0379(4) Uani 1 1 d . . . . .
C16 C 0.6131(2) 0.0599(2) 0.00692(19) 0.0428(4) Uani 1 1 d . . . . .
C10 C 0.8865(2) 0.2501(2) 0.00687(19) 0.0434(5) Uani 1 1 d . . . . .
C2 C 0.80809(19) 0.1948(2) 0.11444(18) 0.0412(4) Uani 1 1 d . . . . .
C3 C 0.69189(19) 0.1155(2) 0.11427(19) 0.0414(4) Uani 1 1 d . . . . .
C4 C 0.9476(2) 0.2977(2) 0.2998(2) 0.0461(5) Uani 1 1 d . . . . .
C22 C 0.5530(2) 0.0133(2) 0.29809(19) 0.0457(5) Uani 1 1 d . . . . .
C23 C 0.4784(2) 0.0711(3) 0.3948(2) 0.0593(6) Uani 1 1 d . . . . .
H23 H 0.4939 0.1623 0.4195 0.071 Uiso 1 1 calc R . . . .
C17 C 0.4743(2) 0.0797(3) 0.0003(2) 0.0556(6) Uani 1 1 d . . . . .
H17 H 0.4308 0.1314 0.0620 0.067 Uiso 1 1 calc R . . . .
C15 C 1.0250(2) 0.2296(3) -0.0006(2) 0.0570(6) Uani 1 1 d . . . . .
H15 H 1.0685 0.1768 0.0605 0.068 Uiso 1 1 calc R . . . .
C9 C 1.0215(2) 0.2393(3) 0.3963(2) 0.0596(6) Uani 1 1 d . . . . .
H9 H 1.0052 0.1483 0.4212 0.071 Uiso 1 1 calc R . . . .
C12 C 0.8997(3) 0.3842(3) -0.1843(3) 0.0675(7) Uani 1 1 d . . . . .
H12 H 0.8571 0.4359 -0.2468 0.081 Uiso 1 1 calc R . . . .
C21 C 0.6753(2) -0.0164(2) -0.0871(2) 0.0542(6) Uani 1 1 d . . . . .
H21 H 0.7682 -0.0285 -0.0854 0.065 Uiso 1 1 calc R . . . .
C20 C 0.5999(3) -0.0748(3) -0.1840(3) 0.0658(7) Uani 1 1 d . . . . .
H20 H 0.6425 -0.1271 -0.2459 0.079 Uiso 1 1 calc R . . . .
C11 C 0.8245(2) 0.3268(2) -0.0877(2) 0.0537(6) Uani 1 1 d . . . . .
H11 H 0.7317 0.3397 -0.0861 0.064 Uiso 1 1 calc R . . . .
C19 C 0.4639(3) -0.0561(3) -0.1891(3) 0.0683(8) Uani 1 1 d . . . . .
H19 H 0.4136 -0.0959 -0.2537 0.082 Uiso 1 1 calc R . . . .
C14 C 1.0983(3) 0.2871(3) -0.0980(3) 0.0677(7) Uani 1 1 d . . . . .
H14 H 1.1908 0.2725 -0.1020 0.081 Uiso 1 1 calc R . . . .
C13 C 1.0361(3) 0.3655(3) -0.1888(3) 0.0703(8) Uani 1 1 d . . . . .
H13 H 1.0863 0.4058 -0.2530 0.084 Uiso 1 1 calc R . . . .
C18 C 0.4017(3) 0.0229(3) -0.0972(3) 0.0675(7) Uani 1 1 d . . . . .
H18 H 0.3093 0.0378 -0.1014 0.081 Uiso 1 1 calc R . . . .
C8 C 1.1205(3) 0.3173(3) 0.4562(3) 0.0698(7) Uani 1 1 d . . . . .
H8 H 1.1707 0.2781 0.5212 0.084 Uiso 1 1 calc R . . . .
C5 C 0.9732(3) 0.4328(3) 0.2625(3) 0.0584(6) Uani 1 1 d . . . . .
H5 H 0.9242 0.4722 0.1968 0.070 Uiso 1 1 calc R . . . .
C24 C 0.3811(3) -0.0069(3) 0.4544(3) 0.0707(7) Uani 1 1 d . . . . .
H24 H 0.3312 0.0322 0.5195 0.085 Uiso 1 1 calc R . . . .
C27 C 0.5284(3) -0.1225(3) 0.2621(3) 0.0602(6) Uani 1 1 d . . . . .
H27 H 0.5778 -0.1619 0.1967 0.072 Uiso 1 1 calc R . . . .
C25 C 0.3570(3) -0.1421(3) 0.4185(3) 0.0714(8) Uani 1 1 d . . . . .
H25 H 0.2909 -0.1939 0.4589 0.086 Uiso 1 1 calc R . . . .
C6 C 1.0717(3) 0.5088(3) 0.3232(3) 0.0708(7) Uani 1 1 d . . . . .
H6 H 1.0885 0.5996 0.2980 0.085 Uiso 1 1 calc R . . . .
C7 C 1.1448(3) 0.4525(3) 0.4199(3) 0.0722(8) Uani 1 1 d . . . . .
H7 H 1.2103 0.5048 0.4608 0.087 Uiso 1 1 calc R . . . .
C26 C 0.4311(3) -0.1998(3) 0.3227(3) 0.0709(7) Uani 1 1 d . . . . .
H26 H 0.4156 -0.2912 0.2985 0.085 Uiso 1 1 calc R . . . .
N1 N 0.66060(18) 0.09365(19) 0.24025(17) 0.0501(4) Uani 1 1 d . . . . .
N2 N 0.75003(18) 0.1551(2) 0.31821(16) 0.0460(4) Uani 1 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
C1 C2 1.393(3) . ?
C1 C4 1.467(3) . ?
C1 N2 1.346(3) . ?
C16 C3 1.481(3) . ?
C16 C17 1.393(3) . ?
C16 C21 1.384(3) . ?
C10 C2 1.481(3) . ?
C10 C15 1.391(3) . ?
C10 C11 1.389(3) . ?
C2 C3 1.384(3) . ?
C3 N1 1.388(3) . ?
C4 C9 1.379(3) . ?
C4 C5 1.384(3) . ?
C22 C23 1.383(3) . ?
C22 C27 1.385(3) . ?
C22 N1 1.456(3) . ?
C23 C24 1.378(4) . ?
C17 C18 1.373(3) . ?
C15 C14 1.380(4) . ?
C9 C8 1.390(4) . ?
C12 C11 1.383(4) . ?
C12 C13 1.367(4) . ?
C21 C20 1.390(3) . ?
C20 C19 1.363(4) . ?
C19 C18 1.383(4) . ?
C14 C13 1.370(4) . ?
C8 C7 1.379(4) . ?
C5 C6 1.380(4) . ?
C24 C25 1.378(4) . ?
C27 C26 1.379(4) . ?
C25 C26 1.373(4) . ?
C6 C7 1.368(4) . ?
N1 N2 1.349(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
C2 C1 C4 130.69(18) . . ?
N2 C1 C2 111.93(16) . . ?
N2 C1 C4 117.36(17) . . ?
C17 C16 C3 120.70(19) . . ?
C21 C16 C3 120.70(19) . . ?
C21 C16 C17 118.6(2) . . ?
C15 C10 C2 120.90(19) . . ?
C11 C10 C2 120.98(19) . . ?
C11 C10 C15 118.1(2) . . ?
C1 C2 C10 124.81(17) . . ?
C3 C2 C1 105.62(18) . . ?
C3 C2 C10 129.56(18) . . ?
C2 C3 C16 129.82(19) . . ?
C2 C3 N1 105.69(17) . . ?
N1 C3 C16 124.48(17) . . ?
C9 C4 C1 119.3(2) . . ?
C9 C4 C5 119.9(2) . . ?
C5 C4 C1 120.8(2) . . ?
C23 C22 C27 119.4(2) . . ?
C23 C22 N1 119.5(2) . . ?
C27 C22 N1 121.0(2) . . ?
C24 C23 C22 119.8(2) . . ?
C18 C17 C16 120.1(2) . . ?
C14 C15 C10 120.5(2) . . ?
C4 C9 C8 119.6(2) . . ?
C13 C12 C11 120.5(3) . . ?
C16 C21 C20 120.5(2) . . ?
C19 C20 C21 120.5(3) . . ?
C12 C11 C10 120.6(2) . . ?
C20 C19 C18 119.2(2) . . ?
C13 C14 C15 120.6(3) . . ?
C12 C13 C14 119.6(2) . . ?
C17 C18 C19 121.0(2) . . ?
C7 C8 C9 120.4(3) . . ?
C6 C5 C4 119.7(2) . . ?
C25 C24 C23 120.7(3) . . ?
C26 C27 C22 120.3(3) . . ?
C26 C25 C24 119.6(3) . . ?
C7 C6 C5 120.9(3) . . ?
C6 C7 C8 119.4(3) . . ?
C25 C26 C27 120.2(3) . . ?
C3 N1 C22 130.67(17) . . ?
N2 N1 C3 112.03(16) . . ?
N2 N1 C22 117.26(17) . . ?
C1 N2 N1 104.73(15) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_chemical_compound_source        Synthesized
####################################################################### 
# 
# 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_peru_sm_43_0m
_database_code_depnum_ccdc_archive 'CCDC 1032190'
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2015-09-28 downloaded from the CCDC.
;
_audit_creation_date             2015-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        '1-(2-Pyridyl)-3,4,5-triphenyl-1H-pyrazole '
_chemical_formula_moiety         'C26 H19 N3'
_chemical_formula_sum            'C26 H19 N3'
_chemical_formula_weight         373.44
_chemical_absolute_configuration ?
_chemical_melting_point          447.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.7331(3)
_cell_length_b                   9.7771(3)
_cell_length_c                   10.5392(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.204(2)
_cell_angle_gamma                90
_cell_volume                     1002.92(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3269
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.14
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0558 before and 0.0431 after correction.
The Ratio of minimum to maximum transmission is 0.8797.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14531
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_min         2.854
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                3206
_reflns_number_total             4526
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.0(10)
_refine_ls_extinction_coef       0.026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4526
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²+0.0084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1186
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1611(3) -0.2708(3) -0.2401(2) 0.0433(6) Uani 1 1 d . . . . .
N2 N -0.2506(2) -0.2090(3) -0.3181(2) 0.0526(6) Uani 1 1 d . . . . .
C9 C 0.0237(4) -0.2992(4) -0.3946(3) 0.0674(9) Uani 1 1 d . . . . .
N1 N -0.3403(2) -0.1470(3) -0.2396(2) 0.0573(6) Uani 1 1 d . . . . .
C10 C -0.1119(3) -0.3052(3) -0.0046(3) 0.0481(6) Uani 1 1 d . . . . .
C16 C -0.3875(3) -0.1127(3) -0.0049(2) 0.0474(6) Uani 1 1 d . . . . .
C22 C -0.4470(3) -0.0639(3) -0.2979(3) 0.0533(7) Uani 1 1 d . . . . .
C4 C -0.0532(3) -0.3546(3) -0.2988(3) 0.0530(7) Uani 1 1 d . . . . .
C19 C -0.5396(4) 0.0037(4) 0.1902(3) 0.0740(11) Uani 1 1 d . . . . .
C13 C 0.0400(4) -0.4221(4) 0.1923(4) 0.0745(11) Uani 1 1 d . . . . .
C2 C -0.1914(3) -0.2494(3) -0.1126(2) 0.0477(6) Uani 1 1 d . . . . .
C15 C 0.0297(3) -0.2866(4) 0.0032(3) 0.0634(8) Uani 1 1 d . . . . .
C3 C -0.3084(3) -0.1685(3) -0.1130(2) 0.0486(6) Uani 1 1 d . . . . .
C21 C -0.3239(4) -0.0370(3) 0.0889(3) 0.0605(8) Uani 1 1 d . . . . .
C11 C -0.1757(4) -0.3811(3) 0.0898(3) 0.0596(8) Uani 1 1 d . . . . .
C17 C -0.5293(3) -0.1318(4) 0.0017(3) 0.0624(8) Uani 1 1 d . . . . .
C23 C -0.5252(4) -0.1178(4) -0.3943(3) 0.0671(9) Uani 1 1 d . . . . .
C20 C -0.4007(4) 0.0220(4) 0.1853(3) 0.0702(9) Uani 1 1 d . . . . .
C12 C -0.0989(5) -0.4386(4) 0.1862(4) 0.0727(10) Uani 1 1 d . . . . .
C14 C 0.1043(4) -0.3444(5) 0.1008(4) 0.0741(10) Uani 1 1 d . . . . .
C18 C -0.6035(4) -0.0740(4) 0.0998(4) 0.0740(10) Uani 1 1 d . . . . .
C5 C -0.0355(5) -0.4850(4) -0.2607(4) 0.0695(10) Uani 1 1 d . . . . .
C24 C -0.6204(4) -0.0351(5) -0.4534(4) 0.0825(11) Uani 1 1 d . . . . .
C8 C 0.1218(4) -0.3802(5) -0.4553(4) 0.0816(11) Uani 1 1 d . . . . .
N3 N -0.4600(4) 0.0673(3) -0.2573(4) 0.0860(10) Uani 1 1 d . . . . .
C25 C -0.6371(5) 0.0975(5) -0.4161(5) 0.0891(13) Uani 1 1 d . . . . .
C7 C 0.1387(5) -0.5140(5) -0.4182(4) 0.0874(12) Uani 1 1 d . . . . .
C6 C 0.0604(5) -0.5643(5) -0.3215(5) 0.0929(14) Uani 1 1 d . . . . .
C26 C -0.5572(5) 0.1464(5) -0.3184(5) 0.0953(14) Uani 1 1 d . . . . .
H9 H 0.010(3) -0.196(4) -0.423(3) 0.059(8) Uiso 1 1 d . . . . .
H6 H 0.082(6) -0.648(8) -0.300(6) 0.14(2) Uiso 1 1 d . . . . .
H7 H 0.225(5) -0.574(5) -0.464(5) 0.110(14) Uiso 1 1 d . . . . .
H8 H 0.174(4) -0.337(5) -0.525(4) 0.094(13) Uiso 1 1 d . . . . .
H5 H -0.075(5) -0.512(5) -0.211(5) 0.089(17) Uiso 1 1 d . . . . .
H13 H 0.097(4) -0.463(4) 0.265(4) 0.073(10) Uiso 1 1 d . . . . .
H12 H -0.143(4) -0.490(5) 0.248(4) 0.078(11) Uiso 1 1 d . . . . .
H14 H 0.208(5) -0.332(5) 0.111(4) 0.095(13) Uiso 1 1 d . . . . .
H15 H 0.067(4) -0.236(5) -0.063(4) 0.089(12) Uiso 1 1 d . . . . .
H11 H -0.274(5) -0.397(5) 0.083(5) 0.112(16) Uiso 1 1 d . . . . .
H20 H -0.353(4) 0.077(4) 0.252(4) 0.079(11) Uiso 1 1 d . . . . .
H17 H -0.573(3) -0.183(4) -0.066(3) 0.071(10) Uiso 1 1 d . . . . .
H21 H -0.233(4) -0.023(4) 0.086(3) 0.069(10) Uiso 1 1 d . . . . .
H19 H -0.585(4) 0.061(5) 0.258(4) 0.084(11) Uiso 1 1 d . . . . .
H18 H -0.720(7) -0.078(7) 0.096(6) 0.16(2) Uiso 1 1 d . . . . .
H23 H -0.512(3) -0.214(4) -0.418(3) 0.065(9) Uiso 1 1 d . . . . .
H25 H -0.703(5) 0.156(5) -0.462(4) 0.097(13) Uiso 1 1 d . . . . .
H26 H -0.572(5) 0.243(7) -0.293(5) 0.118(16) Uiso 1 1 d . . . . .
H24 H -0.682(5) -0.075(5) -0.512(4) 0.098(13) Uiso 1 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
C1 N2 1.340(3) . ?
C1 C4 1.471(4) . ?
C1 C2 1.392(4) . ?
N2 N1 1.349(3) . ?
C9 C4 1.371(4) . ?
C9 C8 1.397(5) . ?
N1 C22 1.453(4) . ?
N1 C3 1.386(4) . ?
C10 C2 1.478(4) . ?
C10 C15 1.393(4) . ?
C10 C11 1.389(4) . ?
C16 C3 1.482(4) . ?
C16 C21 1.380(4) . ?
C16 C17 1.394(4) . ?
C22 C23 1.372(4) . ?
C22 N3 1.358(5) . ?
C4 C5 1.347(5) . ?
C19 C20 1.365(6) . ?
C19 C18 1.366(6) . ?
C13 C12 1.363(6) . ?
C13 C14 1.379(6) . ?
C2 C3 1.387(4) . ?
C15 C14 1.378(5) . ?
C21 C20 1.389(5) . ?
C11 C12 1.379(5) . ?
C17 C18 1.384(5) . ?
C23 C24 1.377(5) . ?
C5 C6 1.374(7) . ?
C24 C25 1.364(7) . ?
C8 C7 1.375(7) . ?
N3 C26 1.380(6) . ?
C25 C26 1.375(7) . ?
C7 C6 1.366(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C4 117.2(2) . . ?
N2 C1 C2 112.7(2) . . ?
C2 C1 C4 130.1(2) . . ?
C1 N2 N1 104.28(19) . . ?
C4 C9 C8 119.2(4) . . ?
N2 N1 C22 117.1(2) . . ?
N2 N1 C3 112.3(2) . . ?
C3 N1 C22 130.5(2) . . ?
C15 C10 C2 120.8(3) . . ?
C11 C10 C2 121.0(3) . . ?
C11 C10 C15 118.1(3) . . ?
C21 C16 C3 121.0(3) . . ?
C21 C16 C17 118.6(3) . . ?
C17 C16 C3 120.4(3) . . ?
C23 C22 N1 119.5(3) . . ?
N3 C22 N1 117.5(3) . . ?
N3 C22 C23 122.9(3) . . ?
C9 C4 C1 118.8(3) . . ?
C5 C4 C1 119.5(3) . . ?
C5 C4 C9 121.6(3) . . ?
C20 C19 C18 119.7(3) . . ?
C12 C13 C14 119.0(3) . . ?
C1 C2 C10 125.1(2) . . ?
C3 C2 C1 105.0(2) . . ?
C3 C2 C10 129.8(2) . . ?
C14 C15 C10 120.6(4) . . ?
N1 C3 C16 124.7(2) . . ?
N1 C3 C2 105.7(2) . . ?
C2 C3 C16 129.6(2) . . ?
C16 C21 C20 120.4(3) . . ?
C12 C11 C10 120.2(3) . . ?
C18 C17 C16 120.1(3) . . ?
C22 C23 C24 118.7(4) . . ?
C19 C20 C21 120.6(4) . . ?
C13 C12 C11 121.4(4) . . ?
C15 C14 C13 120.6(3) . . ?
C19 C18 C17 120.7(3) . . ?
C4 C5 C6 118.8(5) . . ?
C25 C24 C23 120.6(4) . . ?
C7 C8 C9 119.4(4) . . ?
C22 N3 C26 116.6(4) . . ?
C24 C25 C26 118.6(4) . . ?
C6 C7 C8 119.2(4) . . ?
C7 C6 C5 121.7(4) . . ?
C25 C26 N3 122.6(4) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_chemical_compound_source        Synthesized
####################################################################### 
# 
# 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_preu_sm_tpp
_database_code_depnum_ccdc_archive 'CCDC 1032191'
_audit_update_record             
;
2014-10-31 deposited with the CCDC.
2015-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N2'
_chemical_formula_weight         296.36

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Fdd2 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   29.627(10)
_cell_length_b                   36.790(12)
_cell_length_c                   5.865(2)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     6393(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4601
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      21.71

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.016
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.008
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2496
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS-2008/1

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25733
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         27.88
_reflns_number_total             3652
_reflns_number_gt                2867
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT  A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0552P)²+0.9593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_number_reflns         3652
_refine_ls_number_parameters     208
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37159(5) -0.04089(4) 0.2873(3) 0.0437(3) Uani 1 1 d . . .
C2 C 0.37384(6) -0.06954(4) 0.4415(3) 0.0560(4) Uani 1 1 d . . .
H2 H 0.3868 -0.0658 0.5839 0.067 Uiso 1 1 calc R . .
C3 C 0.35709(6) -0.10342(4) 0.3866(4) 0.0642(5) Uani 1 1 d . . .
H3 H 0.3593 -0.1224 0.4909 0.077 Uiso 1 1 calc R . .
C4 C 0.33733(6) -0.10917(4) 0.1794(4) 0.0599(5) Uani 1 1 d . . .
H4 H 0.3255 -0.1319 0.1436 0.072 Uiso 1 1 calc R . .
C5 C 0.33491(6) -0.08123(5) 0.0237(3) 0.0571(4) Uani 1 1 d . . .
H5 H 0.3217 -0.0852 -0.1179 0.068 Uiso 1 1 calc R . .
C6 C 0.35199(5) -0.04733(4) 0.0760(3) 0.0492(4) Uani 1 1 d . . .
H6 H 0.3504 -0.0287 -0.0309 0.059 Uiso 1 1 calc R . .
C7 C 0.33959(5) 0.03729(4) 0.1470(3) 0.0461(4) Uani 1 1 d . . .
C8 C 0.29737(6) 0.02968(5) 0.2322(4) 0.0667(5) Uani 1 1 d . . .
H8 H 0.2938 0.0182 0.3721 0.080 Uiso 1 1 calc R . .
C9 C 0.26029(7) 0.03985(7) 0.1014(6) 0.1007(10) Uani 1 1 d . . .
H9 H 0.2314 0.0350 0.1551 0.121 Uiso 1 1 calc R . .
C10 C 0.26545(13) 0.05664(7) -0.1025(7) 0.1226(13) Uani 1 1 d . . .
H10 H 0.2403 0.0635 -0.1868 0.147 Uiso 1 1 calc R . .
C11 C 0.30827(12) 0.06346(6) -0.1844(5) 0.1040(10) Uani 1 1 d . . .
H11 H 0.3118 0.0746 -0.3256 0.125 Uiso 1 1 calc R . .
C12 C 0.34558(8) 0.05401(5) -0.0605(3) 0.0669(5) Uani 1 1 d . . .
H12 H 0.3744 0.0588 -0.1154 0.080 Uiso 1 1 calc R . .
C13 C 0.46840(5) 0.05866(4) 0.6282(3) 0.0481(4) Uani 1 1 d . . .
C14 C 0.48220(5) 0.04624(5) 0.8407(3) 0.0569(4) Uani 1 1 d . . .
H14 H 0.4686 0.0258 0.9035 0.068 Uiso 1 1 calc R . .
C15 C 0.51594(7) 0.06388(6) 0.9598(4) 0.0714(6) Uani 1 1 d . . .
H15 H 0.5253 0.0550 1.1006 0.086 Uiso 1 1 calc R . .
C16 C 0.53555(7) 0.09437(6) 0.8708(4) 0.0764(6) Uani 1 1 d U . .
H16 H 0.5583 0.1062 0.9510 0.092 Uiso 1 1 calc R . .
C17 C 0.52167(6) 0.10768(5) 0.6620(4) 0.0734(6) Uani 1 1 d U . .
H17 H 0.5349 0.1286 0.6030 0.088 Uiso 1 1 calc R . .
C18 C 0.48814(5) 0.08995(4) 0.5403(3) 0.0577(4) Uani 1 1 d . . .
H18 H 0.4789 0.0990 0.3998 0.069 Uiso 1 1 calc R . .
N1 N 0.37852(4) 0.02757(3) 0.2778(2) 0.0465(3) Uani 1 1 d . . .
N2 N 0.40435(4) 0.05499(3) 0.3652(2) 0.0483(3) Uani 1 1 d . . .
C23 C 0.39144(5) -0.00577(4) 0.3557(3) 0.0432(3) Uani 1 1 d . . .
C24 C 0.42726(5) 0.00061(4) 0.4982(3) 0.0496(4) Uani 1 1 d . . .
H24 H 0.4438 -0.0167 0.5786 0.060 Uiso 1 1 calc R . .
C25 C 0.43402(5) 0.03816(4) 0.4988(3) 0.0457(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.389(2) . ?
C1 C2 1.390(2) . ?
C1 C23 1.475(2) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.375(3) . ?
C7 C8 1.376(2) . ?
C7 N1 1.4303(19) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.355(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.389(3) . ?
C13 C18 1.391(2) . ?
C13 C25 1.477(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 C23 1.3637(19) . ?
N1 N2 1.3660(16) . ?
N2 C25 1.330(2) . ?
C23 C24 1.371(2) . ?
C24 C25 1.396(2) . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.11(14) . . ?
C6 C1 C23 123.95(14) . . ?
C2 C1 C23 117.92(15) . . ?
C3 C2 C1 121.06(17) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 120.12(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.80(16) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.53(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.37(16) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 121.98(17) . . ?
C12 C7 N1 118.84(16) . . ?
C8 C7 N1 119.18(17) . . ?
C7 C8 C9 117.6(2) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 118.7(2) . . ?
C11 C12 H12 120.7 . . ?
C7 C12 H12 120.7 . . ?
C14 C13 C18 118.77(15) . . ?
C14 C13 C25 119.75(15) . . ?
C18 C13 C25 121.46(16) . . ?
C15 C14 C13 120.82(18) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.19(18) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C23 N1 N2 112.40(12) . . ?
C23 N1 C7 129.10(12) . . ?
N2 N1 C7 117.94(11) . . ?
C25 N2 N1 104.33(12) . . ?
N1 C23 C24 105.53(12) . . ?
N1 C23 C1 125.79(13) . . ?
C24 C23 C1 128.61(13) . . ?
C23 C24 C25 106.37(13) . . ?
C23 C24 H24 126.8 . . ?
C25 C24 H24 126.8 . . ?
N2 C25 C24 111.37(13) . . ?
N2 C25 C13 121.37(13) . . ?
C24 C25 C13 127.25(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
C6 C1 C2 C3 0.0(3) . . . . ?
C23 C1 C2 C3 -178.19(16) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C23 C1 C6 C5 178.74(15) . . . . ?
C12 C7 C8 C9 -0.6(3) . . . . ?
N1 C7 C8 C9 179.35(16) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
N1 C7 C12 C11 -179.61(17) . . . . ?
C18 C13 C14 C15 -2.1(2) . . . . ?
C25 C13 C14 C15 176.67(14) . . . . ?
C13 C14 C15 C16 1.3(2) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C18 -0.8(3) . . . . ?
C16 C17 C18 C13 0.0(3) . . . . ?
C14 C13 C18 C17 1.4(2) . . . . ?
C25 C13 C18 C17 -177.27(14) . . . . ?
C12 C7 N1 C23 -121.82(18) . . . . ?
C8 C7 N1 C23 58.2(2) . . . . ?
C12 C7 N1 N2 67.5(2) . . . . ?
C8 C7 N1 N2 -112.49(17) . . . . ?
C23 N1 N2 C25 0.35(17) . . . . ?
C7 N1 N2 C25 172.58(14) . . . . ?
N2 N1 C23 C24 -0.29(18) . . . . ?
C7 N1 C23 C24 -171.43(16) . . . . ?
N2 N1 C23 C1 -177.53(14) . . . . ?
C7 N1 C23 C1 11.3(3) . . . . ?
C6 C1 C23 N1 28.8(2) . . . . ?
C2 C1 C23 N1 -153.12(16) . . . . ?
C6 C1 C23 C24 -147.77(17) . . . . ?
C2 C1 C23 C24 30.3(2) . . . . ?
N1 C23 C24 C25 0.11(18) . . . . ?
C1 C23 C24 C25 177.24(16) . . . . ?
N1 N2 C25 C24 -0.28(18) . . . . ?
N1 N2 C25 C13 -179.55(14) . . . . ?
C23 C24 C25 N2 0.11(19) . . . . ?
C23 C24 C25 C13 179.33(15) . . . . ?
C14 C13 C25 N2 146.46(15) . . . . ?
C18 C13 C25 N2 -34.8(2) . . . . ?
C14 C13 C25 C24 -32.7(2) . . . . ?
C18 C13 C25 C24 146.00(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.031
