# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_4h
_database_code_depnum_ccdc_archive 'CCDC 2194495'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_vrf_PLAT911_4h                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600          5 Report
RESPONSE: Four reflections (1 1 2, 2 0 4, 1 0 4, 2 0 4)  were not observed
 due to the presence of the beam-stop. The fixed kappa geometry of the
 instrument does not allow collecting all inequivalent reflections.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1-Benzyl-N-(4-methylphenyl)-1H-1,2,4-triazol-3-amine
_chemical_name_common            ?
_chemical_melting_point          414-416
_chemical_formula_moiety         'C16 H16 N4'
_chemical_formula_sum            'C16 H16 N4'
_chemical_formula_weight         264.33
# grown from CH2Cl2/hexane (slow evaporation of a sample
# solution in methylene chloride in a hexane vapor atmosphere)
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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9515(3)
_cell_length_b                   6.05280(10)
_cell_length_c                   20.1410(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.8980(10)
_cell_angle_gamma                90
_cell_volume                     1332.00(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9840
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      36.30
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7133
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            46205
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.864
_diffrn_reflns_theta_max         33.148
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5081
_reflns_number_gt                4375
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.4699P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5081
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_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_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
N2 N 0.64173(7) 0.51072(12) 0.55766(3) 0.01526(13) Uani 1 1 d . . . . .
N3 N 0.62771(7) 0.81332(12) 0.49024(3) 0.01598(13) Uani 1 1 d . . . . .
N1 N 0.72682(6) 0.50386(11) 0.51046(3) 0.01481(13) Uani 1 1 d . . . . .
N4 N 0.49019(7) 0.78741(12) 0.57554(3) 0.01539(13) Uani 1 1 d . . . . .
C1 C 0.58456(7) 0.70047(13) 0.54309(4) 0.01331(14) Uani 1 1 d . . . . .
C2 C 0.71620(8) 0.68195(14) 0.47158(4) 0.01577(15) Uani 1 1 d . . . . .
H2 H 0.7686(12) 0.705(2) 0.4361(6) 0.021(3) Uiso 1 1 d . . . . .
C3 C 0.43787(7) 0.70405(13) 0.63179(4) 0.01339(14) Uani 1 1 d . . . . .
C4 C 0.46378(7) 0.49543(13) 0.65927(4) 0.01452(14) Uani 1 1 d . . . . .
H4 H 0.5196(11) 0.398(2) 0.6376(6) 0.019(3) Uiso 1 1 d . . . . .
C5 C 0.40819(8) 0.42939(13) 0.71635(4) 0.01495(14) Uani 1 1 d . . . . .
H5 H 0.4286(12) 0.283(2) 0.7354(6) 0.021(3) Uiso 1 1 d . . . . .
C6 C 0.32685(7) 0.56484(14) 0.74766(4) 0.01544(14) Uani 1 1 d . . . . .
C7 C 0.30045(8) 0.77176(15) 0.71904(4) 0.01707(15) Uani 1 1 d . . . . .
H7 H 0.2414(13) 0.869(2) 0.7397(7) 0.028(3) Uiso 1 1 d . . . . .
C8 C 0.35429(8) 0.84047(14) 0.66221(4) 0.01595(15) Uani 1 1 d . . . . .
H8 H 0.3384(12) 0.987(2) 0.6440(7) 0.024(3) Uiso 1 1 d . . . . .
C9 C 0.27169(9) 0.49525(17) 0.81082(4) 0.02097(17) Uani 1 1 d . . . . .
H9A H 0.1810(16) 0.512(3) 0.8076(8) 0.046(5) Uiso 1 1 d . . . . .
H9B H 0.3063(15) 0.581(3) 0.8497(8) 0.047(5) Uiso 1 1 d . . . . .
H9C H 0.2902(14) 0.337(3) 0.8209(8) 0.038(4) Uiso 1 1 d . . . . .
C10 C 0.80738(8) 0.31552(14) 0.50658(4) 0.01629(15) Uani 1 1 d . . . . .
H10A H 0.8507(11) 0.336(2) 0.4654(6) 0.020(3) Uiso 1 1 d . . . . .
H10B H 0.7539(11) 0.182(2) 0.5021(6) 0.020(3) Uiso 1 1 d . . . . .
C11 C 0.89919(7) 0.29383(13) 0.56587(4) 0.01439(14) Uani 1 1 d . . . . .
C12 C 0.95744(8) 0.09074(14) 0.57685(4) 0.01623(15) Uani 1 1 d . . . . .
H12 H 0.9345(12) -0.036(2) 0.5471(6) 0.023(3) Uiso 1 1 d . . . . .
C13 C 1.04524(8) 0.06305(15) 0.62958(4) 0.01876(16) Uani 1 1 d . . . . .
H13 H 1.0878(12) -0.078(2) 0.6355(7) 0.025(3) Uiso 1 1 d . . . . .
C14 C 1.07457(8) 0.23808(16) 0.67239(5) 0.02051(17) Uani 1 1 d . . . . .
H14 H 1.1364(13) 0.221(2) 0.7102(7) 0.031(4) Uiso 1 1 d . . . . .
C15 C 1.01536(9) 0.43982(16) 0.66258(5) 0.02129(17) Uani 1 1 d . . . . .
H15 H 1.0359(13) 0.564(2) 0.6931(7) 0.031(4) Uiso 1 1 d . . . . .
C16 C 0.92798(8) 0.46803(14) 0.60948(4) 0.01838(16) Uani 1 1 d . . . . .
H16 H 0.8845(12) 0.609(2) 0.6033(7) 0.025(3) Uiso 1 1 d . . . . .
H4A H 0.4584(12) 0.916(2) 0.5584(7) 0.027(3) 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
N2 C1 1.3313(10) . ?
N2 N1 1.3763(10) . ?
N3 C2 1.3275(11) . ?
N3 C1 1.3753(10) . ?
N1 C2 1.3327(10) . ?
N1 C10 1.4469(11) . ?
N4 C1 1.3652(10) . ?
N4 C3 1.3982(10) . ?
N4 H4A 0.912(14) . ?
C2 H2 0.957(13) . ?
C3 C4 1.4000(11) . ?
C3 C8 1.4040(11) . ?
C4 C5 1.3954(11) . ?
C4 H4 0.973(12) . ?
C5 C6 1.3926(11) . ?
C5 H5 0.983(13) . ?
C6 C7 1.4006(12) . ?
C6 C9 1.5051(12) . ?
C7 C8 1.3866(11) . ?
C7 H7 0.986(14) . ?
C8 H8 0.974(14) . ?
C9 H9A 0.996(17) . ?
C9 H9B 0.993(17) . ?
C9 H9C 0.998(16) . ?
C10 C11 1.5137(12) . ?
C10 H10A 0.992(13) . ?
C10 H10B 0.998(13) . ?
C11 C16 1.3946(12) . ?
C11 C12 1.3956(11) . ?
C12 C13 1.3934(12) . ?
C12 H12 0.993(13) . ?
C13 C14 1.3896(13) . ?
C13 H13 0.976(14) . ?
C14 C15 1.3904(13) . ?
C14 H14 0.990(14) . ?
C15 C16 1.3963(12) . ?
C15 H15 0.988(15) . ?
C16 H16 0.980(14) . ?

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 N2 N1 101.78(6) . . ?
C2 N3 C1 102.56(7) . . ?
C2 N1 N2 110.20(7) . . ?
C2 N1 C10 129.40(7) . . ?
N2 N1 C10 120.33(7) . . ?
C1 N4 C3 127.88(7) . . ?
C1 N4 H4A 115.5(9) . . ?
C3 N4 H4A 116.6(9) . . ?
N2 C1 N4 125.95(7) . . ?
N2 C1 N3 114.70(7) . . ?
N4 C1 N3 119.35(7) . . ?
N3 C2 N1 110.76(7) . . ?
N3 C2 H2 127.6(8) . . ?
N1 C2 H2 121.6(8) . . ?
N4 C3 C4 124.24(7) . . ?
N4 C3 C8 117.17(7) . . ?
C4 C3 C8 118.59(7) . . ?
C5 C4 C3 119.74(7) . . ?
C5 C4 H4 121.3(7) . . ?
C3 C4 H4 119.0(7) . . ?
C6 C5 C4 122.18(8) . . ?
C6 C5 H5 119.2(7) . . ?
C4 C5 H5 118.6(7) . . ?
C5 C6 C7 117.43(7) . . ?
C5 C6 C9 121.58(8) . . ?
C7 C6 C9 120.97(8) . . ?
C8 C7 C6 121.36(8) . . ?
C8 C7 H7 119.8(8) . . ?
C6 C7 H7 118.8(8) . . ?
C7 C8 C3 120.68(7) . . ?
C7 C8 H8 120.7(8) . . ?
C3 C8 H8 118.6(8) . . ?
C6 C9 H9A 111.8(10) . . ?
C6 C9 H9B 111.6(10) . . ?
H9A C9 H9B 108.8(13) . . ?
C6 C9 H9C 110.7(9) . . ?
H9A C9 H9C 107.6(13) . . ?
H9B C9 H9C 106.2(13) . . ?
N1 C10 C11 113.61(7) . . ?
N1 C10 H10A 105.9(7) . . ?
C11 C10 H10A 109.9(7) . . ?
N1 C10 H10B 106.6(7) . . ?
C11 C10 H10B 110.8(7) . . ?
H10A C10 H10B 109.8(10) . . ?
C16 C11 C12 119.00(8) . . ?
C16 C11 C10 122.74(7) . . ?
C12 C11 C10 118.26(7) . . ?
C13 C12 C11 120.73(8) . . ?
C13 C12 H12 120.0(8) . . ?
C11 C12 H12 119.3(8) . . ?
C14 C13 C12 119.97(8) . . ?
C14 C13 H13 120.2(8) . . ?
C12 C13 H13 119.8(8) . . ?
C13 C14 C15 119.70(8) . . ?
C13 C14 H14 120.9(8) . . ?
C15 C14 H14 119.4(9) . . ?
C14 C15 C16 120.33(8) . . ?
C14 C15 H15 119.8(8) . . ?
C16 C15 H15 119.9(8) . . ?
C11 C16 C15 120.25(8) . . ?
C11 C16 H16 119.4(8) . . ?
C15 C16 H16 120.4(8) . . ?

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
C1 N2 N1 C2 -0.25(9) . . . . ?
C1 N2 N1 C10 -177.50(7) . . . . ?
N1 N2 C1 N4 179.96(8) . . . . ?
N1 N2 C1 N3 -0.08(9) . . . . ?
C3 N4 C1 N2 3.30(14) . . . . ?
C3 N4 C1 N3 -176.66(7) . . . . ?
C2 N3 C1 N2 0.37(9) . . . . ?
C2 N3 C1 N4 -179.66(7) . . . . ?
C1 N3 C2 N1 -0.52(9) . . . . ?
N2 N1 C2 N3 0.51(10) . . . . ?
C10 N1 C2 N3 177.44(8) . . . . ?
C1 N4 C3 C4 -9.47(13) . . . . ?
C1 N4 C3 C8 170.41(8) . . . . ?
N4 C3 C4 C5 178.83(8) . . . . ?
C8 C3 C4 C5 -1.04(12) . . . . ?
C3 C4 C5 C6 -0.11(12) . . . . ?
C4 C5 C6 C7 1.02(12) . . . . ?
C4 C5 C6 C9 -177.37(8) . . . . ?
C5 C6 C7 C8 -0.78(12) . . . . ?
C9 C6 C7 C8 177.63(8) . . . . ?
C6 C7 C8 C3 -0.37(13) . . . . ?
N4 C3 C8 C7 -178.60(8) . . . . ?
C4 C3 C8 C7 1.28(12) . . . . ?
C2 N1 C10 C11 115.63(9) . . . . ?
N2 N1 C10 C11 -67.71(10) . . . . ?
N1 C10 C11 C16 -17.79(12) . . . . ?
N1 C10 C11 C12 162.47(7) . . . . ?
C16 C11 C12 C13 -1.52(12) . . . . ?
C10 C11 C12 C13 178.22(8) . . . . ?
C11 C12 C13 C14 0.77(13) . . . . ?
C12 C13 C14 C15 0.45(13) . . . . ?
C13 C14 C15 C16 -0.88(14) . . . . ?
C12 C11 C16 C15 1.08(13) . . . . ?
C10 C11 C16 C15 -178.65(8) . . . . ?
C14 C15 C16 C11 0.11(14) . . . . ?

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
_geom_hbond_publ_flag
N4 H4A N3 0.912(14) 2.099(14) 3.0050(10) 172.6(13) 3_676 yes

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_9f
_database_code_depnum_ccdc_archive 'CCDC 2194497'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT089_9f                  
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       6.91 Note  
RESPONSE: The data were collected using Cu Ka radiation. Due to poor
 crystal qualitynd weak diffraction ability, the use of Mo Ka radiation
 was unresonable. Moreover, a part of the molecule is disordered.
 The real data (3060) to parameters (269) ratio is 11.37. The reported
 ratio by the web version of CheckCIF  is provided for a centrosymmetric
 space group but not for the real chiral one.
;
_vrf_PLAT340_9f                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.007 Ang.  
RESPONSE: This is likely due to poor crystal quality for all
 provided crystals.
;
_vrf_PLAT915_9f                  
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         64 %     
RESPONSE:  The used strategy provided an average redundancy of 6.0
 for all non-equivalent reflections for the found space group - P3(1).
 However, the strategy covered only 76.5% of Friedel pairs. This issue
 likely arised from the poor crystal quality and the presence of some
 minor domains for all crystals in provided specimens. Despite this,
 the absolute structure was undoubtedly determined.
;
_audit_creation_date             2022-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
1-Benzyl-N,3-diphenyl-1H-1,2,4-triazol-5-amine
_chemical_formula_moiety         'C21 H18 N4'
_chemical_formula_sum            'C21 H18 N4'
_chemical_formula_weight         326.39
_chemical_absolute_configuration ad
_chemical_melting_point          423-425
_chemical_oxdiff_usercomment     JA-N27
# grown from CH2Cl2/hexane (slow evaporation of a sample
# solution in methylene chloride in a hexane vapor atmosphere)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   10.5968(2)
_cell_length_b                   10.5968(2)
_cell_length_c                   13.4314(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1306.17(6)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    12961
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5040
_cell_measurement_theta_min      4.7870
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.667
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             516
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.4093
0 0 1 0.3295
-2 1 0 0.0526
1 -1 0 0.0641
-1 1 0 0.0388
-2 3 0 0.0422
1 -3 0 0.0628
0 -1 0 0.0627
0 1 0 0.0513
1 0 0 0.0444
-1 0 0 0.0600

_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0003 0.0000 -0.9998 0.0004 -0.0240 0.1121
0.0003 -0.0000 0.9998 -0.0004 0.0240 -0.1121
-1.9995 0.9999 0.0002 -0.0300 0.2830 0.0606
0.9997 -0.9998 0.0001 0.0984 -0.1330 -0.0288
-0.9997 0.9998 -0.0001 -0.0984 0.1330 0.0288
-1.9992 2.9992 -0.0005 -0.3636 0.2490 0.0545
0.9994 -2.9991 0.0008 0.4320 -0.0990 -0.0227
-0.0001 -0.9997 0.0004 0.1668 0.0170 0.0030
0.0001 0.9997 -0.0004 -0.1668 -0.0170 -0.0030
0.9998 -0.0001 -0.0003 -0.0684 -0.1500 -0.0318
-0.9998 0.0001 0.0003 0.0684 0.1500 0.0318

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18357
_diffrn_reflns_point_group_measured_fraction_full 0.832
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.907
_diffrn_reflns_theta_min         4.819
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00 -38.00   0.50    0.45    --  -48.43 -16.00   5.00  168
  2  ω    -25.00  26.00   0.50    0.45    --  -48.43  16.00 175.00  102
  3  ω    -25.00  25.00   0.50    0.45    --   48.43 -16.00   5.00  100
  4  ω   -161.00 -76.00   0.50    1.80    --  -86.25 -16.00   5.00  170
  5  ω     98.00 178.00   0.50    1.80    --  107.75  16.00 175.00  160
  6  ω    -26.00  26.00   0.50    0.45    --  -48.43  19.00 -30.00  104
  7  ω    -86.00 -13.00   0.50    0.45    --  -48.43 125.00-120.00  146
  8  ω     38.00 122.00   0.50    0.45    --   48.43  16.00 175.00  168
  9  ω    -25.00  26.00   0.50    0.45    --   48.43 -19.00-120.00  102
 10  ω    -51.00 -14.00   0.50    1.80    --  -86.25  45.00 150.00   74
 11  ω     36.00 109.00   0.50    1.80    --  107.75-112.00-144.93  146
 12  ω     36.00 105.00   0.50    1.80    --  107.75 -77.00-120.00  138
 13  ω     36.00 107.00   0.50    1.80    --  107.75-102.00 117.68  142
 14  ω     36.00  71.00   0.50    1.80    --  107.75 -61.00-120.00   70
 15  ω     93.00 178.00   0.50    1.80    --  107.75  61.00  30.00  170
 16  ω     86.00 178.00   0.50    1.80    --  107.75  77.00-150.00  184
 17  ω     97.00 178.00   0.50    1.80    --  107.75  30.00  90.00  162
 18  ω     95.00 178.00   0.50    1.80    --  107.75 125.00 -30.00  166
 19  ω     60.00 104.00   0.50    1.80    --  107.75 -95.00-120.00   88
 20  ω     62.00  96.00   0.50    1.80    --  107.75 -77.00  60.00   68
 21  ω     39.00 105.00   0.50    1.80    --  107.75 -95.00-150.00  132
 22  ω     42.00  70.00   0.50    1.80    --  107.75 -61.00  60.00   56
 23  ω     97.00 178.00   0.50    1.80    --  107.75  45.00 120.00  162
 24  ω    100.00 177.00   0.50    1.80    --  107.75  15.00-150.00  154
 25  ω    130.00 156.00   0.50    1.80    --  107.75  30.00 -60.00   52
 26  ω     43.00  69.00   0.50    1.80    --  107.75 -95.00  60.00   52
 27  ω     36.00  72.00   0.50    1.80    --  107.75-105.00 171.50   72
 28  ω     37.00  88.00   0.50    1.80    --  107.75 -77.00 -60.00  102
 29  ω     37.00  62.00   0.50    1.80    --  107.75 -95.00 -90.00   50
 30  ω     80.00 105.00   0.50    1.80    --  107.75 -95.00 -90.00   50
 31  ω     99.00 177.00   0.50    1.80    --  107.75  30.00-120.00  156
 32  ω     38.00  63.00   0.50    1.80    --  107.75 -86.00 131.78   50
 33  ω     93.00 129.00   0.50    1.80    --  107.75 -86.00 131.78   72
 34  ω     59.00  85.00   0.50    1.80    --  107.75-105.00 178.77   52
 35  ω     38.00  71.00   0.50    1.80    --  107.75 -61.00 -60.00   66
 36  ω    112.00 138.00   0.50    1.80    --  107.75  61.00 -60.00   52
 37  ω     81.00 107.00   0.50    1.80    --  107.75-176.00 123.00   52
 38  ω     56.00  82.00   0.50    1.80    --  107.75 -95.00 120.00   52
 39  ω     58.00  84.00   0.50    1.80    --  107.75-125.00  60.00   52
 40  ω     49.00  75.00   0.50    1.80    --  107.75 -77.00 -90.00   52
 41  ω    -78.00 -53.00   0.50    1.80    --  -86.25 132.00-139.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684484000
_diffrn_orient_matrix_UB_12      -0.1668486000
_diffrn_orient_matrix_UB_13      -0.0004216000
_diffrn_orient_matrix_UB_21      -0.1500296000
_diffrn_orient_matrix_UB_22      -0.0169707000
_diffrn_orient_matrix_UB_23      0.0240404000
_diffrn_orient_matrix_UB_31      -0.0318408000
_diffrn_orient_matrix_UB_32      -0.0030751000
_diffrn_orient_matrix_UB_33      -0.1121278000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.665
_reflns_Friedel_fraction_max     0.642
_reflns_number_gt                3023
_reflns_number_total             3060
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1103 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0050(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.029
_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)+(0.0424P)²+0.9234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1332
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N4-H4
 0.85 with sigma of 0.02
 C4-C5 \\sim C4-C5A \\sim C5-C6 \\sim C5A-C6A \\sim C6-C7 \\sim C6A-C7A \\sim
C7-C8 \\sim C7A-C8A \\sim C8-C9
 \\sim C8A-C9A \\sim C4-C9 \\sim C4-C9A
 with sigma of 0.003
 N3-C10 \\sim N3-C10A
 with sigma of 0.003
 C10-C11 \\sim C10A-C11A
 with sigma of 0.003
 C11-C12 \\sim C11A-C12A \\sim C12-C13 \\sim C12A-C13A \\sim C13-C14 \\sim
C13A-C14A \\sim C14-C15 ~
 C14A-C15A \\sim C15-C16 \\sim C15A-C16A \\sim C11-C16 \\sim C11A-C16A
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9: within 2A with sigma of 0.006 and sigma
for terminal atoms of 0.012 within 2A
C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16: within 2A with sigma of
0.006 and sigma for terminal atoms of 0.012 within 2A
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
Uanis(C7) = Uanis(C7A)
Uanis(C8) = Uanis(C8A)
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
4. Others
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=
 Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=
 Sof(H9)=FVAR(1)
 Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=
 Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=1-FVAR(2)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=
 Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10A(H10C,H10D)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C5A(H5A), C6A(H6A), C7A(H7A),
 C8A(H8A), C9A(H9A), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C16A(H16A), C18(H18), C19(H19),
  C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2805(3) 0.3213(3) 0.4923(3) 0.0381(7) Uani 1 1 d . . . . .
C1 C 0.2070(4) 0.3526(4) 0.4195(3) 0.0390(8) Uani 1 1 d . . . . .
N2 N 0.2017(3) 0.4715(4) 0.4340(3) 0.0402(7) Uani 1 1 d . . . . .
N3 N 0.2781(4) 0.5238(3) 0.5236(3) 0.0396(7) Uani 1 1 d D . . . .
C3 C 0.3200(4) 0.4294(4) 0.5548(3) 0.0385(8) Uani 1 1 d . . . . .
C4 C 0.1380(4) 0.2551(4) 0.3335(3) 0.0418(9) Uani 1 1 d D . . . .
C5 C 0.1967(13) 0.1693(14) 0.3052(10) 0.053(2) Uani 0.662(13) 1 d D U P A 1
H5 H 0.283216 0.181876 0.335518 0.064 Uiso 0.662(13) 1 calc R U P A 1
C6 C 0.1270(9) 0.0649(10) 0.2319(7) 0.0584(19) Uani 0.662(13) 1 d D U P A 1
H6 H 0.166306 0.005749 0.211596 0.070 Uiso 0.662(13) 1 calc R U P A 1
C7 C 0.0006(9) 0.0463(9) 0.1882(7) 0.0564(18) Uani 0.662(13) 1 d D U P A 1
H7 H -0.045870 -0.024810 0.137549 0.068 Uiso 0.662(13) 1 calc R U P A 1
C8 C -0.0587(11) 0.1309(10) 0.2180(9) 0.0491(18) Uani 0.662(13) 1 d D U P A 1
H8 H -0.146378 0.116759 0.188657 0.059 Uiso 0.662(13) 1 calc R U P A 1
C9 C 0.0106(18) 0.236(3) 0.2908(17) 0.0436(14) Uani 0.662(13) 1 d D U P A 1
H9 H -0.028919 0.295133 0.311240 0.052 Uiso 0.662(13) 1 calc R U P A 1
C5A C 0.209(3) 0.190(3) 0.2885(17) 0.053(2) Uani 0.338(13) 1 d D . P A 2
H5A H 0.293478 0.199392 0.319583 0.064 Uiso 0.338(13) 1 calc R U P A 2
C6A C 0.1620(18) 0.1111(19) 0.2006(13) 0.0584(19) Uani 0.338(13) 1 d D . P A 2
H6A H 0.214620 0.069117 0.172213 0.070 Uiso 0.338(13) 1 calc R U P A 2
C7A C 0.0375(17) 0.0946(18) 0.1547(14) 0.0564(18) Uani 0.338(13) 1 d D . P A 2
H7A H 0.000366 0.037546 0.096034 0.068 Uiso 0.338(13) 1 calc R U P A 2
C8A C -0.031(2) 0.1636(19) 0.1968(16) 0.0491(18) Uani 0.338(13) 1 d D . P A 2
H8A H -0.113119 0.158356 0.163865 0.059 Uiso 0.338(13) 1 calc R U P A 2
C9A C 0.015(4) 0.240(5) 0.286(3) 0.0436(14) Uani 0.338(13) 1 d D . P A 2
H9A H -0.036871 0.282621 0.313679 0.052 Uiso 0.338(13) 1 calc R U P A 2
N4 N 0.3963(4) 0.4517(4) 0.6408(3) 0.0418(7) Uani 1 1 d D . . . .
H4 H 0.417(5) 0.536(3) 0.669(4) 0.053(13) Uiso 1 1 d D . . . .
C10 C 0.305(2) 0.6648(7) 0.5598(12) 0.039(2) Uani 0.572(4) 1 d D . P B 1
H10A H 0.349905 0.681433 0.626813 0.047 Uiso 0.572(4) 1 calc R U P B 1
H10B H 0.210745 0.661509 0.567070 0.047 Uiso 0.572(4) 1 calc R U P B 1
C11 C 0.4030(8) 0.7920(8) 0.4942(7) 0.0366(15) Uani 0.572(4) 1 d D U P B 1
C12 C 0.3708(9) 0.8997(7) 0.4691(6) 0.0531(14) Uani 0.572(4) 1 d D U P B 1
H12 H 0.279927 0.890786 0.486949 0.064 Uiso 0.572(4) 1 calc R U P B 1
C13 C 0.4742(9) 1.0205(9) 0.4174(8) 0.0637(18) Uani 0.572(4) 1 d D U P B 1
H13 H 0.456605 1.098535 0.404616 0.076 Uiso 0.572(4) 1 calc R U P B 1
C14 C 0.6027(9) 1.0308(9) 0.3839(7) 0.0639(19) Uani 0.572(4) 1 d D U P B 1
H14 H 0.670051 1.111977 0.345434 0.077 Uiso 0.572(4) 1 calc R U P B 1
C15 C 0.6308(8) 0.9200(7) 0.4076(6) 0.0593(16) Uani 0.572(4) 1 d D U P B 1
H15 H 0.719369 0.926272 0.386603 0.071 Uiso 0.572(4) 1 calc R U P B 1
C16 C 0.5309(6) 0.8003(8) 0.4618(6) 0.0468(13) Uani 0.572(4) 1 d D U P B 1
H16 H 0.550183 0.723881 0.476734 0.056 Uiso 0.572(4) 1 calc R U P B 1
C10A C 0.275(4) 0.6454(11) 0.5713(15) 0.039(2) Uani 0.428(4) 1 d D . P B 2
H10C H 0.324967 0.665994 0.636384 0.047 Uiso 0.428(4) 1 calc R U P B 2
H10D H 0.172119 0.619106 0.583593 0.047 Uiso 0.428(4) 1 calc R U P B 2
C11A C 0.3475(9) 0.7796(12) 0.5068(10) 0.0366(15) Uani 0.428(4) 1 d D . P B 2
C12A C 0.2551(11) 0.8328(10) 0.4847(8) 0.0531(14) Uani 0.428(4) 1 d D . P B 2
H12A H 0.158432 0.785949 0.509947 0.064 Uiso 0.428(4) 1 calc R U P B 2
C13A C 0.3057(12) 0.9554(10) 0.4251(9) 0.0637(18) Uani 0.428(4) 1 d D . P B 2
H13A H 0.243355 0.992800 0.408857 0.076 Uiso 0.428(4) 1 calc R U P B 2
C14A C 0.4470(11) 1.0235(14) 0.3892(11) 0.0639(19) Uani 0.428(4) 1 d D . P B 2
H14A H 0.479232 1.104174 0.345395 0.077 Uiso 0.428(4) 1 calc R U P B 2
C15A C 0.5422(12) 0.9756(11) 0.4163(9) 0.0593(16) Uani 0.428(4) 1 d D . P B 2
H15A H 0.641110 1.027104 0.395483 0.071 Uiso 0.428(4) 1 calc R U P B 2
C16A C 0.4907(9) 0.8513(10) 0.4742(7) 0.0468(13) Uani 0.428(4) 1 d D . P B 2
H16A H 0.553730 0.815210 0.491581 0.056 Uiso 0.428(4) 1 calc R U P B 2
C17 C 0.4458(4) 0.3589(4) 0.6802(4) 0.0406(8) Uani 1 1 d . . . . .
C18 C 0.5340(4) 0.4114(4) 0.7648(4) 0.0450(9) Uani 1 1 d . . . . .
H18 H 0.554392 0.501737 0.793185 0.054 Uiso 1 1 calc R U . . .
C19 C 0.5913(5) 0.3333(5) 0.8069(4) 0.0516(10) Uani 1 1 d . . . . .
H19 H 0.650474 0.369980 0.864644 0.062 Uiso 1 1 calc R U . . .
C20 C 0.5645(6) 0.2025(5) 0.7670(4) 0.0585(12) Uani 1 1 d . . . . .
H20 H 0.607053 0.150385 0.795322 0.070 Uiso 1 1 calc R U . . .
C21 C 0.4745(6) 0.1487(5) 0.6849(4) 0.0603(13) Uani 1 1 d . . . . .
H21 H 0.454102 0.057847 0.657451 0.072 Uiso 1 1 calc R U . . .
C22 C 0.4127(5) 0.2251(5) 0.6413(4) 0.0496(10) Uani 1 1 d . . . . .
H22 H 0.349023 0.185563 0.585868 0.060 Uiso 1 1 calc R U . . .


_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 1.389(5) . ?
N1 C3 1.309(5) . ?
C1 N2 1.304(5) . ?
C1 C4 1.476(5) . ?
N2 N3 1.400(4) . ?
N3 C3 1.348(5) . ?
N3 C10 1.456(5) . ?
N3 C10A 1.456(6) . ?
C3 N4 1.362(5) . ?
C4 C5 1.387(3) . ?
C4 C9 1.386(3) . ?
C4 C5A 1.386(3) . ?
C4 C9A 1.386(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9500 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.386(4) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.386(4) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.386(4) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.386(4) . ?
C9A H9A 0.9500 . ?
N4 H4 0.90(2) . ?
N4 C17 1.427(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.508(7) . ?
C11 C12 1.386(4) . ?
C11 C16 1.384(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9500 . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.507(8) . ?
C11A C12A 1.384(4) . ?
C11A C16A 1.386(4) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.385(4) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.384(4) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.385(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.385(4) . ?
C16A H16A 0.9500 . ?
C17 C18 1.398(6) . ?
C17 C22 1.382(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.369(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.377(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.399(6) . ?
C22 H22 0.9500 . ?

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
C3 N1 C1 102.4(3) . . ?
N1 C1 C4 121.6(3) . . ?
N2 C1 N1 115.1(3) . . ?
N2 C1 C4 123.2(4) . . ?
C1 N2 N3 102.5(3) . . ?
N2 N3 C10 118.2(10) . . ?
N2 N3 C10A 117.6(15) . . ?
C3 N3 N2 108.2(3) . . ?
C3 N3 C10 133.4(11) . . ?
C3 N3 C10A 133.1(13) . . ?
N1 C3 N3 111.8(3) . . ?
N1 C3 N4 126.7(4) . . ?
N3 C3 N4 121.5(3) . . ?
C5 C4 C1 116.5(5) . . ?
C9 C4 C1 122.0(6) . . ?
C9 C4 C5 121.0(8) . . ?
C5A C4 C1 119.2(9) . . ?
C9A C4 C1 123.4(11) . . ?
C9A C4 C5A 116.7(15) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.9(7) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(8) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.3(8) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.7(10) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 H9 120.2 . . ?
C8 C9 C4 119.6(10) . . ?
C8 C9 H9 120.2 . . ?
C4 C5A H5A 118.2 . . ?
C6A C5A C4 123.6(16) . . ?
C6A C5A H5A 118.2 . . ?
C5A C6A H6A 120.5 . . ?
C7A C6A C5A 119.0(16) . . ?
C7A C6A H6A 120.5 . . ?
C6A C7A H7A 121.0 . . ?
C6A C7A C8A 118.0(16) . . ?
C8A C7A H7A 121.0 . . ?
C7A C8A H8A 118.9 . . ?
C9A C8A C7A 122(2) . . ?
C9A C8A H8A 118.9 . . ?
C4 C9A H9A 119.8 . . ?
C8A C9A C4 120(2) . . ?
C8A C9A H9A 119.8 . . ?
C3 N4 H4 111(3) . . ?
C3 N4 C17 125.9(3) . . ?
C17 N4 H4 123(3) . . ?
N3 C10 H10A 108.6 . . ?
N3 C10 H10B 108.6 . . ?
N3 C10 C11 114.7(5) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C12 C11 C10 122.5(9) . . ?
C16 C11 C10 116.9(8) . . ?
C16 C11 C12 120.6(7) . . ?
C11 C12 H12 120.8 . . ?
C11 C12 C13 118.4(7) . . ?
C13 C12 H12 120.8 . . ?
C12 C13 H13 119.1 . . ?
C12 C13 C14 121.8(8) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.6(8) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(7) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.9(7) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N3 C10A H10C 109.5 . . ?
N3 C10A H10D 109.5 . . ?
N3 C10A C11A 110.7(8) . . ?
H10C C10A H10D 108.1 . . ?
C11A C10A H10C 109.5 . . ?
C11A C10A H10D 109.5 . . ?
C12A C11A C10A 112.0(14) . . ?
C12A C11A C16A 120.8(10) . . ?
C16A C11A C10A 127.1(14) . . ?
C11A C12A H12A 120.5 . . ?
C11A C12A C13A 119.0(10) . . ?
C13A C12A H12A 120.5 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A C12A 120.0(10) . . ?
C14A C13A H13A 120.0 . . ?
C13A C14A H14A 119.5 . . ?
C13A C14A C15A 120.9(11) . . ?
C15A C14A H14A 119.5 . . ?
C14A C15A H15A 120.6 . . ?
C16A C15A C14A 118.9(11) . . ?
C16A C15A H15A 120.6 . . ?
C11A C16A H16A 119.9 . . ?
C15A C16A C11A 120.1(10) . . ?
C15A C16A H16A 119.9 . . ?
C18 C17 N4 115.5(4) . . ?
C22 C17 N4 125.1(4) . . ?
C22 C17 C18 119.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.1(4) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.7 . . ?
C19 C20 C21 118.6(4) . . ?
C21 C20 H20 120.7 . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.5(4) . . ?
C22 C21 H21 119.3 . . ?
C17 C22 C21 118.9(4) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?

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
_geom_hbond_publ_flag
N4 H4 N2 0.90(2) 2.22(3) 3.070(5) 158(4) 2_665 yes

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 N2 N3 0.1(4) . . . . ?
N1 C1 C4 C5 -25.9(9) . . . . ?
N1 C1 C4 C9 146.2(15) . . . . ?
N1 C1 C4 C5A -39.3(16) . . . . ?
N1 C1 C4 C9A 150(3) . . . . ?
N1 C3 N4 C17 -1.2(6) . . . . ?
C1 N1 C3 N3 -1.2(4) . . . . ?
C1 N1 C3 N4 179.9(4) . . . . ?
C1 N2 N3 C3 -0.9(4) . . . . ?
C1 N2 N3 C10 175.0(7) . . . . ?
C1 N2 N3 C10A -170.6(8) . . . . ?
C1 C4 C5 C6 173.2(9) . . . . ?
C1 C4 C9 C8 -172.4(14) . . . . ?
C1 C4 C5A C6A -172(2) . . . . ?
C1 C4 C9A C8A 171(3) . . . . ?
N2 C1 C4 C5 155.4(8) . . . . ?
N2 C1 C4 C9 -32.5(16) . . . . ?
N2 C1 C4 C5A 142.0(16) . . . . ?
N2 C1 C4 C9A -29(3) . . . . ?
N2 N3 C3 N1 1.4(4) . . . . ?
N2 N3 C3 N4 -179.7(3) . . . . ?
N2 N3 C10 C11 -65(2) . . . . ?
N2 N3 C10A C11A -64(3) . . . . ?
N3 C3 N4 C17 -179.9(3) . . . . ?
N3 C10 C11 C12 134.3(14) . . . . ?
N3 C10 C11 C16 -48(2) . . . . ?
N3 C10A C11A C12A 123(2) . . . . ?
N3 C10A C11A C16A -60(3) . . . . ?
C3 N1 C1 N2 0.7(4) . . . . ?
C3 N1 C1 C4 -178.1(3) . . . . ?
C3 N3 C10 C11 109.9(14) . . . . ?
C3 N3 C10A C11A 129.4(15) . . . . ?
C3 N4 C17 C18 174.1(4) . . . . ?
C3 N4 C17 C22 -6.0(6) . . . . ?
C4 C1 N2 N3 178.9(3) . . . . ?
C4 C5 C6 C7 -0.3(17) . . . . ?
C4 C5A C6A C7A -1(4) . . . . ?
C5 C4 C9 C8 -1(3) . . . . ?
C5 C6 C7 C8 -0.7(14) . . . . ?
C6 C7 C8 C9 1.1(18) . . . . ?
C7 C8 C9 C4 0(3) . . . . ?
C9 C4 C5 C6 1(2) . . . . ?
C5A C4 C9A C8A 0(6) . . . . ?
C5A C6A C7A C8A 3(3) . . . . ?
C6A C7A C8A C9A -4(3) . . . . ?
C7A C8A C9A C4 3(6) . . . . ?
C9A C4 C5A C6A -1(4) . . . . ?
N4 C17 C18 C19 -178.0(4) . . . . ?
N4 C17 C22 C21 177.0(4) . . . . ?
C10 N3 C3 N1 -173.6(7) . . . . ?
C10 N3 C3 N4 5.4(8) . . . . ?
C10 C11 C12 C13 173.1(12) . . . . ?
C10 C11 C16 C15 -175.1(11) . . . . ?
C11 C12 C13 C14 5.1(15) . . . . ?
C12 C11 C16 C15 2.9(13) . . . . ?
C12 C13 C14 C15 -3.5(15) . . . . ?
C13 C14 C15 C16 1.4(14) . . . . ?
C14 C15 C16 C11 -1.2(13) . . . . ?
C16 C11 C12 C13 -4.7(13) . . . . ?
C10A N3 C3 N1 168.8(13) . . . . ?
C10A N3 C3 N4 -12.3(14) . . . . ?
C10A C11A C12A C13A -179.4(13) . . . . ?
C10A C11A C16A C15A -178.9(14) . . . . ?
C11A C12A C13A C14A -0.5(18) . . . . ?
C12A C11A C16A C15A -2(2) . . . . ?
C12A C13A C14A C15A -4(2) . . . . ?
C13A C14A C15A C16A 5(2) . . . . ?
C14A C15A C16A C11A -2.1(19) . . . . ?
C16A C11A C12A C13A 3.1(19) . . . . ?
C17 C18 C19 C20 0.5(7) . . . . ?
C18 C17 C22 C21 -3.1(6) . . . . ?
C18 C19 C20 C21 -2.0(7) . . . . ?
C19 C20 C21 C22 1.0(8) . . . . ?
C20 C21 C22 C17 1.6(7) . . . . ?
C22 C17 C18 C19 2.1(6) . . . . ?

_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 1.374
_oxdiff_exptl_absorpt_empirical_full_min 0.499
####################################################################### 
# 
# 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_4u
_database_code_depnum_ccdc_archive 'CCDC 2194496'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_vrf_PLAT911_4u                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600          5 Report
RESPONSE: Four reflections (1 1 0, -1 0 1, 0 1 2, -1 2 4)  were not observed
 due to the presence of the beam-stop. The fixed kappa geometry of the
 instrument does not allow collecting all inequivalent reflections.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1-tert-Butyl-N-[2,6-di(propan-2-yl)phenyl]-1H-1,2,4-triazol-3-amine
_chemical_name_common            ?
_chemical_melting_point          386-388
_chemical_formula_moiety         'C18 H28 N4'
_chemical_formula_sum            'C18 H28 N4'
_chemical_formula_weight         300.44
# grown from CH2Cl2/hexane (slow evaporation of a sample
# solution in methylene chloride in a hexane vapor atmosphere)
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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8745(2)
_cell_length_b                   9.8920(2)
_cell_length_c                   11.1653(3)
_cell_angle_alpha                91.1400(10)
_cell_angle_beta                 104.8090(10)
_cell_angle_gamma                113.3590(10)
_cell_volume                     861.78(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      35.63
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.47
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7440
_exptl_absorpt_correction_T_max  0.8023
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            55140
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.904
_diffrn_reflns_theta_max         33.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6773
_reflns_number_gt                5997
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;
_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²+0.2012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6773
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40138(7) 0.13626(6) 0.64814(5) 0.01355(10) Uani 1 1 d . . . . .
N2 N 0.56321(7) 0.24772(6) 0.69945(5) 0.01425(10) Uani 1 1 d . . . . .
N3 N 0.41702(7) 0.31251(6) 0.52811(5) 0.01459(11) Uani 1 1 d . . . . .
N4 N 0.69898(7) 0.48578(6) 0.63747(5) 0.01346(10) Uani 1 1 d . . . . .
H4 H 0.6725(16) 0.5506(14) 0.5951(11) 0.025(3) Uiso 1 1 d . . . . .
C1 C 0.56446(8) 0.35078(7) 0.62422(6) 0.01176(11) Uani 1 1 d . . . . .
C2 C 0.32021(8) 0.17755(7) 0.54763(6) 0.01534(12) Uani 1 1 d . . . . .
H2 H 0.2049(17) 0.1153(14) 0.4969(12) 0.029(3) Uiso 1 1 d . . . . .
C3 C 0.35009(8) -0.00858(7) 0.69660(6) 0.01525(12) Uani 1 1 d . . . . .
C4 C 0.41818(11) 0.02031(9) 0.83904(7) 0.02172(14) Uani 1 1 d . . . . .
H4A H 0.3810(18) -0.0747(15) 0.8709(12) 0.032(3) Uiso 1 1 d . . . . .
H4B H 0.5454(16) 0.0689(14) 0.8684(11) 0.025(3) Uiso 1 1 d . . . . .
H4C H 0.3708(16) 0.0828(14) 0.8728(12) 0.026(3) Uiso 1 1 d . . . . .
C5 C 0.42625(10) -0.10057(8) 0.64112(7) 0.02095(14) Uani 1 1 d . . . . .
H5A H 0.3963(17) -0.1974(15) 0.6738(12) 0.030(3) Uiso 1 1 d . . . . .
H5B H 0.3778(17) -0.1187(14) 0.5494(12) 0.030(3) Uiso 1 1 d . . . . .
H5C H 0.5551(18) -0.0475(15) 0.6642(12) 0.032(3) Uiso 1 1 d . . . . .
C6 C 0.15469(10) -0.08753(9) 0.65687(8) 0.02231(14) Uani 1 1 d . . . . .
H6A H 0.1201(17) -0.1805(15) 0.6929(12) 0.032(3) Uiso 1 1 d . . . . .
H6B H 0.1034(18) -0.0271(15) 0.6874(13) 0.035(3) Uiso 1 1 d . . . . .
H6C H 0.1051(17) -0.1107(15) 0.5626(13) 0.034(3) Uiso 1 1 d . . . . .
C7 C 0.84581(8) 0.54121(7) 0.74479(6) 0.01203(11) Uani 1 1 d . . . . .
C8 C 0.97104(8) 0.48467(7) 0.75974(6) 0.01286(11) Uani 1 1 d . . . . .
C9 C 1.11437(8) 0.54246(7) 0.86504(6) 0.01495(11) Uani 1 1 d . . . . .
H9 H 1.2000(16) 0.5018(13) 0.8768(11) 0.024(3) Uiso 1 1 d . . . . .
C10 C 1.13686(8) 0.65603(8) 0.95180(6) 0.01587(12) Uani 1 1 d . . . . .
H10 H 1.2367(16) 0.6948(13) 1.0267(11) 0.025(3) Uiso 1 1 d . . . . .
C11 C 1.01447(9) 0.71420(7) 0.93402(6) 0.01563(12) Uani 1 1 d . . . . .
H11 H 1.0316(16) 0.7964(14) 0.9971(11) 0.025(3) Uiso 1 1 d . . . . .
C12 C 0.86670(8) 0.65720(7) 0.83230(6) 0.01348(11) Uani 1 1 d . . . . .
C13 C 0.95913(9) 0.36576(7) 0.66504(6) 0.01508(11) Uani 1 1 d . . . . .
H13 H 0.8543(14) 0.3432(12) 0.5945(10) 0.018(2) Uiso 1 1 d . . . . .
C14 C 1.11569(10) 0.42232(9) 0.61447(7) 0.02102(14) Uani 1 1 d . . . . .
H14A H 1.0969(17) 0.3520(15) 0.5419(12) 0.032(3) Uiso 1 1 d . . . . .
H14B H 1.1375(18) 0.5203(15) 0.5850(13) 0.035(3) Uiso 1 1 d . . . . .
H14C H 1.2206(18) 0.4348(15) 0.6776(13) 0.035(3) Uiso 1 1 d . . . . .
C15 C 0.94107(10) 0.22237(8) 0.72180(7) 0.02040(13) Uani 1 1 d . . . . .
H15A H 0.9250(18) 0.1398(16) 0.6561(13) 0.037(3) Uiso 1 1 d . . . . .
H15B H 1.0502(17) 0.2391(14) 0.7921(12) 0.028(3) Uiso 1 1 d . . . . .
H15C H 0.8438(17) 0.1860(14) 0.7572(12) 0.028(3) Uiso 1 1 d . . . . .
C16 C 0.72689(9) 0.71251(8) 0.82063(7) 0.01765(12) Uani 1 1 d . . . . .
H16 H 0.6739(17) 0.7106(14) 0.7316(12) 0.030(3) Uiso 1 1 d . . . . .
C17 C 0.79397(12) 0.87215(9) 0.88327(9) 0.02624(16) Uani 1 1 d . . . . .
H17A H 0.6954(18) 0.9046(15) 0.8655(13) 0.035(3) Uiso 1 1 d . . . . .
H17B H 0.8368(19) 0.8818(16) 0.9774(14) 0.039(4) Uiso 1 1 d . . . . .
H17C H 0.891(2) 0.9444(17) 0.8530(14) 0.043(4) Uiso 1 1 d . . . . .
C18 C 0.58839(11) 0.60905(10) 0.87579(10) 0.02784(17) Uani 1 1 d . . . . .
H18A H 0.493(2) 0.6436(17) 0.8632(15) 0.048(4) Uiso 1 1 d . . . . .
H18B H 0.539(2) 0.4999(17) 0.8359(14) 0.045(4) Uiso 1 1 d . . . . .
H18C H 0.6338(18) 0.6174(15) 0.9653(13) 0.034(3) 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
N1 C2 1.3354(8) . ?
N1 N2 1.3802(7) . ?
N1 C3 1.4807(8) . ?
N2 C1 1.3322(8) . ?
N3 C2 1.3288(8) . ?
N3 C1 1.3712(8) . ?
N4 C1 1.3667(8) . ?
N4 C7 1.4295(8) . ?
N4 H4 0.875(13) . ?
C2 H2 0.968(13) . ?
C3 C4 1.5263(10) . ?
C3 C6 1.5273(10) . ?
C3 C5 1.5323(10) . ?
C4 H4A 0.972(13) . ?
C4 H4B 0.994(13) . ?
C4 H4C 0.989(13) . ?
C5 H5A 0.992(13) . ?
C5 H5B 0.986(13) . ?
C5 H5C 1.009(14) . ?
C6 H6A 0.977(13) . ?
C6 H6B 0.984(14) . ?
C6 H6C 1.014(14) . ?
C7 C8 1.4063(9) . ?
C7 C12 1.4141(9) . ?
C8 C9 1.3997(9) . ?
C8 C13 1.5190(9) . ?
C9 C10 1.3858(10) . ?
C9 H9 0.975(12) . ?
C10 C11 1.3928(10) . ?
C10 H10 0.985(12) . ?
C11 C12 1.3980(9) . ?
C11 H11 1.002(12) . ?
C12 C16 1.5212(10) . ?
C13 C15 1.5319(10) . ?
C13 C14 1.5361(10) . ?
C13 H13 0.995(11) . ?
C14 H14A 0.992(13) . ?
C14 H14B 0.990(14) . ?
C14 H14C 0.974(14) . ?
C15 H15A 1.027(14) . ?
C15 H15B 1.030(13) . ?
C15 H15C 0.982(13) . ?
C16 C17 1.5281(11) . ?
C16 C18 1.5336(12) . ?
C16 H16 0.981(13) . ?
C17 H17A 1.022(14) . ?
C17 H17B 1.011(15) . ?
C17 H17C 1.017(16) . ?
C18 H18A 1.013(16) . ?
C18 H18B 1.030(15) . ?
C18 H18C 0.966(14) . ?

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 N1 N2 109.24(5) . . ?
C2 N1 C3 129.86(6) . . ?
N2 N1 C3 120.46(5) . . ?
C1 N2 N1 102.15(5) . . ?
C2 N3 C1 102.18(5) . . ?
C1 N4 C7 123.11(5) . . ?
C1 N4 H4 114.2(8) . . ?
C7 N4 H4 117.7(8) . . ?
N2 C1 N4 124.72(6) . . ?
N2 C1 N3 114.90(5) . . ?
N4 C1 N3 120.38(6) . . ?
N3 C2 N1 111.53(6) . . ?
N3 C2 H2 125.5(8) . . ?
N1 C2 H2 123.0(8) . . ?
N1 C3 C4 108.44(5) . . ?
N1 C3 C6 108.73(6) . . ?
C4 C3 C6 109.87(6) . . ?
N1 C3 C5 108.16(6) . . ?
C4 C3 C5 111.10(6) . . ?
C6 C3 C5 110.47(6) . . ?
C3 C4 H4A 108.3(8) . . ?
C3 C4 H4B 112.2(7) . . ?
H4A C4 H4B 107.9(11) . . ?
C3 C4 H4C 109.8(7) . . ?
H4A C4 H4C 108.9(10) . . ?
H4B C4 H4C 109.7(10) . . ?
C3 C5 H5A 109.9(8) . . ?
C3 C5 H5B 108.9(8) . . ?
H5A C5 H5B 108.9(10) . . ?
C3 C5 H5C 111.0(8) . . ?
H5A C5 H5C 108.1(11) . . ?
H5B C5 H5C 110.0(11) . . ?
C3 C6 H6A 109.0(8) . . ?
C3 C6 H6B 111.5(8) . . ?
H6A C6 H6B 107.6(11) . . ?
C3 C6 H6C 112.0(8) . . ?
H6A C6 H6C 108.9(11) . . ?
H6B C6 H6C 107.7(11) . . ?
C8 C7 C12 120.71(6) . . ?
C8 C7 N4 119.97(6) . . ?
C12 C7 N4 119.27(6) . . ?
C9 C8 C7 118.64(6) . . ?
C9 C8 C13 118.60(6) . . ?
C7 C8 C13 122.75(6) . . ?
C10 C9 C8 121.41(6) . . ?
C10 C9 H9 119.7(7) . . ?
C8 C9 H9 118.9(7) . . ?
C9 C10 C11 119.42(6) . . ?
C9 C10 H10 121.1(7) . . ?
C11 C10 H10 119.5(7) . . ?
C10 C11 C12 121.27(6) . . ?
C10 C11 H11 119.0(7) . . ?
C12 C11 H11 119.7(7) . . ?
C11 C12 C7 118.50(6) . . ?
C11 C12 C16 120.55(6) . . ?
C7 C12 C16 120.85(6) . . ?
C8 C13 C15 111.16(6) . . ?
C8 C13 C14 110.63(6) . . ?
C15 C13 C14 110.61(6) . . ?
C8 C13 H13 107.5(6) . . ?
C15 C13 H13 108.0(7) . . ?
C14 C13 H13 108.7(7) . . ?
C13 C14 H14A 110.0(8) . . ?
C13 C14 H14B 112.4(8) . . ?
H14A C14 H14B 106.9(11) . . ?
C13 C14 H14C 112.3(8) . . ?
H14A C14 H14C 108.9(11) . . ?
H14B C14 H14C 106.2(11) . . ?
C13 C15 H15A 111.1(8) . . ?
C13 C15 H15B 110.7(7) . . ?
H15A C15 H15B 106.5(11) . . ?
C13 C15 H15C 111.9(8) . . ?
H15A C15 H15C 108.4(11) . . ?
H15B C15 H15C 107.9(10) . . ?
C12 C16 C17 113.31(6) . . ?
C12 C16 C18 109.87(6) . . ?
C17 C16 C18 109.57(7) . . ?
C12 C16 H16 108.6(8) . . ?
C17 C16 H16 107.0(8) . . ?
C18 C16 H16 108.3(8) . . ?
C16 C17 H17A 109.0(8) . . ?
C16 C17 H17B 112.4(8) . . ?
H17A C17 H17B 105.5(11) . . ?
C16 C17 H17C 112.6(9) . . ?
H17A C17 H17C 109.3(12) . . ?
H17B C17 H17C 107.7(12) . . ?
C16 C18 H18A 109.2(9) . . ?
C16 C18 H18B 112.3(9) . . ?
H18A C18 H18B 109.6(13) . . ?
C16 C18 H18C 110.1(9) . . ?
H18A C18 H18C 105.2(12) . . ?
H18B C18 H18C 110.2(12) . . ?

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 N1 N2 C1 1.03(7) . . . . ?
C3 N1 N2 C1 174.19(6) . . . . ?
N1 N2 C1 N4 179.22(6) . . . . ?
N1 N2 C1 N3 -0.93(7) . . . . ?
C7 N4 C1 N2 -9.41(10) . . . . ?
C7 N4 C1 N3 170.74(6) . . . . ?
C2 N3 C1 N2 0.46(8) . . . . ?
C2 N3 C1 N4 -179.67(6) . . . . ?
C1 N3 C2 N1 0.25(8) . . . . ?
N2 N1 C2 N3 -0.84(8) . . . . ?
C3 N1 C2 N3 -173.15(6) . . . . ?
C2 N1 C3 C4 -147.14(7) . . . . ?
N2 N1 C3 C4 41.29(8) . . . . ?
C2 N1 C3 C6 -27.71(10) . . . . ?
N2 N1 C3 C6 160.72(6) . . . . ?
C2 N1 C3 C5 92.28(8) . . . . ?
N2 N1 C3 C5 -79.30(7) . . . . ?
C1 N4 C7 C8 75.91(8) . . . . ?
C1 N4 C7 C12 -106.72(7) . . . . ?
C12 C7 C8 C9 1.90(9) . . . . ?
N4 C7 C8 C9 179.24(6) . . . . ?
C12 C7 C8 C13 -176.79(6) . . . . ?
N4 C7 C8 C13 0.54(9) . . . . ?
C7 C8 C9 C10 -1.85(10) . . . . ?
C13 C8 C9 C10 176.90(6) . . . . ?
C8 C9 C10 C11 -0.05(10) . . . . ?
C9 C10 C11 C12 1.96(10) . . . . ?
C10 C11 C12 C7 -1.88(10) . . . . ?
C10 C11 C12 C16 174.47(6) . . . . ?
C8 C7 C12 C11 -0.08(9) . . . . ?
N4 C7 C12 C11 -177.43(6) . . . . ?
C8 C7 C12 C16 -176.42(6) . . . . ?
N4 C7 C12 C16 6.23(9) . . . . ?
C9 C8 C13 C15 65.77(8) . . . . ?
C7 C8 C13 C15 -115.54(7) . . . . ?
C9 C8 C13 C14 -57.54(8) . . . . ?
C7 C8 C13 C14 121.16(7) . . . . ?
C11 C12 C16 C17 28.13(9) . . . . ?
C7 C12 C16 C17 -155.62(7) . . . . ?
C11 C12 C16 C18 -94.81(8) . . . . ?
C7 C12 C16 C18 81.45(8) . . . . ?

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
_geom_hbond_publ_flag
N4 H4 N3 0.875(13) 2.173(13) 3.0433(8) 172.6(11) 2_666 yes

_refine_diff_density_max         0.501
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.047

