# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_20015_lja-6_auto
_audit_block_doi                 10.5517/ccdc.csd.cc29hxc3
_database_code_depnum_ccdc_archive 'CCDC 2130455'
loop_
_audit_author_name
_audit_author_address
'Aleksandra M. Puzyk'
;SPbSU
Russia
;
_audit_update_record             
;
2021-12-22 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H27 N3'
_chemical_formula_sum            'C19 H27 N3'
_chemical_formula_weight         297.43
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H27 N3'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.6026(2)
_cell_length_b                   12.0411(3)
_cell_length_c                   14.2206(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1644.27(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      77.1700
_cell_measurement_theta_min      5.8860
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10544
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.960
_diffrn_reflns_theta_min         5.559
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  22.00   0.50    0.30    --  -47.10  93.00  93.00  186
  2  ω   -176.00 -92.00   0.50    1.50    -- -106.00 -44.00  91.00  168
  3  ω   -139.00 -84.00   0.50    1.50    -- -106.00 -93.00 -18.00  110
  4  ω     45.00 101.00   0.50    1.50    --  113.25 -92.00-119.00  112
  5  ω    -24.00  22.00   0.50    0.30    --   47.10 -19.00-150.00   92
  6  ω    -25.00  22.00   0.50    0.30    --   47.10 -19.00 -30.00   94
  7  ω    -64.00 -35.00   0.50    1.50    -- -106.00  61.00  90.00   58
  8  ω     42.00  68.00   0.50    1.50    --  113.25 -61.00 -90.00   52
  9  ω     42.00  68.00   0.50    1.50    --  113.25 -61.00-180.00   52
 10  ω     62.00 101.00   0.50    1.50    --  113.25 -94.00 150.00   78
 11  ω     45.00  70.00   0.50    1.50    --  113.25 -61.00  60.00   50
 12  ω     43.00 111.00   0.50    1.50    --  113.25-125.00  30.00  136
 13  ω     43.00  71.00   0.50    1.50    --  113.25 -94.00 -90.00   56
 14  ω     84.00 137.00   0.50    1.50    --  113.25  92.00  -6.00  106
 15  ω    -13.00  16.00   0.50    0.30    --  -47.10  19.00-180.00   58
 16  ω   -104.00 -74.00   0.50    0.30    --  -47.10-125.00-150.00   60
 17  ω   -149.00 -99.00   0.50    1.50    -- -106.00 -77.00 -30.00  100
 18  ω   -176.00-151.00   0.50    1.50    -- -106.00 -45.00 -90.00   50
 19  ω   -172.00-120.00   0.50    1.50    -- -106.00 -45.00-180.00  104
 20  ω    -95.00 -49.00   0.50    1.50    -- -106.00  77.00  60.00   92
 21  ω   -121.00 -93.00   0.50    1.50    -- -106.00 -45.00 -90.00   56
 22  ω    -71.00 -39.00   0.50    1.50    -- -106.00  77.00  90.00   64
 23  ω   -100.00 -74.00   0.50    1.50    -- -106.00  77.00  90.00   52
 24  ω     73.00 104.00   0.50    1.50    --  113.25 -94.00-180.00   62
 25  ω     43.00  69.00   0.50    1.50    --  113.25 -61.00-150.00   52
 26  ω    149.00 176.00   0.50    1.50    --  113.25  45.00  60.00   54
 27  ω    107.00 133.00   0.50    1.50    --  113.25  45.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0852714000
_diffrn_orient_matrix_UB_12      -0.0533579000
_diffrn_orient_matrix_UB_13      0.0798354000
_diffrn_orient_matrix_UB_21      0.0205700000
_diffrn_orient_matrix_UB_22      0.1050526000
_diffrn_orient_matrix_UB_23      0.0603019000
_diffrn_orient_matrix_UB_31      -0.1342996000
_diffrn_orient_matrix_UB_32      0.0498258000
_diffrn_orient_matrix_UB_33      -0.0416151000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2876
_reflns_number_total             3091
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.052
_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)+(0.0612P)²+0.0672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0918
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C8(H8), C11(H11), C7(H7)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C19(H19A,H19B,
 H19C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N2 N 0.65103(14) 0.36767(12) 0.40469(11) 0.0206(3) Uani 1 1 d . . . . .
N3 N 0.59035(14) 0.13644(13) 0.40411(11) 0.0212(3) Uani 1 1 d . . . . .
N1 N 0.50384(16) 0.53295(13) 0.39786(11) 0.0260(3) Uani 1 1 d . . . . .
C6 C 0.61978(16) 0.14430(15) 0.50008(12) 0.0190(4) Uani 1 1 d . . . . .
C4 C 0.61511(17) 0.35734(15) 0.49861(12) 0.0189(4) Uani 1 1 d . . . . .
C5 C 0.61792(15) 0.25149(14) 0.54629(13) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.64242(18) 0.15294(16) 0.69759(13) 0.0229(4) Uani 1 1 d . . . . .
H9 H 0.6465 0.1545 0.7643 0.027 Uiso 1 1 calc R . . . .
C10 C 0.61528(16) 0.25243(15) 0.64711(13) 0.0210(4) Uani 1 1 d . . . . .
C12 C 0.55432(19) 0.44664(16) 0.64587(13) 0.0238(4) Uani 1 1 d . . . . .
H12 H 0.5212 0.5103 0.6784 0.029 Uiso 1 1 calc R . . . .
C8 C 0.66266(17) 0.05507(16) 0.65091(13) 0.0237(4) Uani 1 1 d . . . . .
H8 H 0.6864 -0.0100 0.6851 0.028 Uiso 1 1 calc R . . . .
C11 C 0.58118(18) 0.35140(16) 0.69518(12) 0.0237(4) Uani 1 1 d . . . . .
H11 H 0.5769 0.3519 0.7619 0.028 Uiso 1 1 calc R . . . .
C7 C 0.64857(18) 0.05006(15) 0.55262(13) 0.0226(4) Uani 1 1 d . . . . .
H7 H 0.6590 -0.0193 0.5216 0.027 Uiso 1 1 calc R . . . .
C3 C 0.57458(17) 0.45239(15) 0.54829(12) 0.0218(4) Uani 1 1 d . . . . .
C15 C 0.6313(2) 0.03675(16) 0.35428(13) 0.0256(4) Uani 1 1 d . . . . .
H15A H 0.7276 0.0179 0.3705 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.6242 0.0495 0.2864 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.5697 -0.0246 0.3723 0.038 Uiso 1 1 calc GR . . . .
C13 C 0.77164(18) 0.31330(16) 0.36431(13) 0.0239(4) Uani 1 1 d . . . . .
H13A H 0.8419 0.3691 0.3481 0.036 Uiso 1 1 calc GR . . . .
H13B H 0.7439 0.2729 0.3075 0.036 Uiso 1 1 calc GR . . . .
H13C H 0.8108 0.2610 0.4101 0.036 Uiso 1 1 calc GR . . . .
C2 C 0.55420(18) 0.55894(16) 0.49374(12) 0.0239(4) Uani 1 1 d . . . . .
H2 H 0.4762 0.5990 0.5256 0.029 Uiso 1 1 calc R . . . .
C16 C 0.6810(2) 0.64107(15) 0.49443(13) 0.0255(4) Uani 1 1 d . . . . .
C14 C 0.45985(18) 0.18290(16) 0.36899(12) 0.0241(4) Uani 1 1 d . . . . .
H14A H 0.3880 0.1251 0.3688 0.036 Uiso 1 1 calc GR . . . .
H14B H 0.4736 0.2106 0.3049 0.036 Uiso 1 1 calc GR . . . .
H14C H 0.4304 0.2442 0.4098 0.036 Uiso 1 1 calc GR . . . .
C1 C 0.59461(18) 0.45833(16) 0.34790(13) 0.0245(4) Uani 1 1 d . . . . .
H1A H 0.6732 0.5016 0.3217 0.029 Uiso 1 1 calc R . . . .
H1B H 0.5426 0.4261 0.2944 0.029 Uiso 1 1 calc R . . . .
C19 C 0.6601(2) 0.72969(16) 0.41890(14) 0.0302(4) Uani 1 1 d . . . . .
H19A H 0.6677 0.6955 0.3566 0.045 Uiso 1 1 calc GR . . . .
H19B H 0.7316 0.7872 0.4256 0.045 Uiso 1 1 calc GR . . . .
H19C H 0.5677 0.7632 0.4260 0.045 Uiso 1 1 calc GR . . . .
C17 C 0.8213(2) 0.58292(16) 0.47840(15) 0.0296(4) Uani 1 1 d . . . . .
H17A H 0.8312 0.5214 0.5230 0.044 Uiso 1 1 calc GR . . . .
H17B H 0.8972 0.6362 0.4879 0.044 Uiso 1 1 calc GR . . . .
H17C H 0.8252 0.5541 0.4140 0.044 Uiso 1 1 calc GR . . . .
C18 C 0.6868(3) 0.69738(18) 0.59059(15) 0.0385(5) Uani 1 1 d . . . . .
H18A H 0.5981 0.7350 0.6029 0.058 Uiso 1 1 calc GR . . . .
H18B H 0.7625 0.7519 0.5913 0.058 Uiso 1 1 calc GR . . . .
H18C H 0.7034 0.6414 0.6393 0.058 Uiso 1 1 calc GR . . . .
H1 H 0.415(3) 0.5021(19) 0.4055(16) 0.027(6) 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 C4 1.385(2) . ?
N2 C13 1.449(2) . ?
N2 C1 1.462(2) . ?
N3 C6 1.397(2) . ?
N3 C15 1.448(2) . ?
N3 C14 1.460(2) . ?
N1 C2 1.480(2) . ?
N1 C1 1.439(2) . ?
C6 C5 1.448(3) . ?
C6 C7 1.386(3) . ?
C4 C5 1.444(3) . ?
C4 C3 1.400(3) . ?
C5 C10 1.434(2) . ?
C9 C10 1.421(3) . ?
C9 C8 1.366(3) . ?
C10 C11 1.412(3) . ?
C12 C11 1.369(3) . ?
C12 C3 1.403(3) . ?
C8 C7 1.406(3) . ?
C3 C2 1.512(3) . ?
C2 C16 1.569(3) . ?
C16 C19 1.527(3) . ?
C16 C17 1.536(3) . ?
C16 C18 1.527(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N2 C13 122.73(15) . . ?
C4 N2 C1 120.50(15) . . ?
C13 N2 C1 114.50(14) . . ?
C6 N3 C15 118.64(15) . . ?
C6 N3 C14 118.80(15) . . ?
C15 N3 C14 112.53(14) . . ?
C1 N1 C2 112.87(14) . . ?
N3 C6 C5 120.08(16) . . ?
C7 C6 N3 120.75(16) . . ?
C7 C6 C5 119.16(16) . . ?
N2 C4 C5 121.83(16) . . ?
N2 C4 C3 118.84(16) . . ?
C3 C4 C5 119.33(16) . . ?
C4 C5 C6 125.01(16) . . ?
C10 C5 C6 117.45(16) . . ?
C10 C5 C4 117.53(16) . . ?
C8 C9 C10 120.52(17) . . ?
C9 C10 C5 119.69(17) . . ?
C11 C10 C5 119.65(17) . . ?
C11 C10 C9 120.63(17) . . ?
C11 C12 C3 121.47(18) . . ?
C9 C8 C7 120.42(17) . . ?
C12 C11 C10 120.18(16) . . ?
C6 C7 C8 121.33(17) . . ?
C4 C3 C12 119.82(17) . . ?
C4 C3 C2 118.08(15) . . ?
C12 C3 C2 122.11(17) . . ?
N1 C2 C3 109.61(15) . . ?
N1 C2 C16 113.12(14) . . ?
C3 C2 C16 115.55(14) . . ?
C19 C16 C2 109.52(16) . . ?
C19 C16 C17 109.22(16) . . ?
C19 C16 C18 108.92(16) . . ?
C17 C16 C2 113.13(15) . . ?
C18 C16 C2 108.28(15) . . ?
C18 C16 C17 107.67(17) . . ?
N1 C1 N2 114.70(15) . . ?

_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 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.608
####################################################################### 
# 
# 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_20081_lja-7
_audit_block_doi                 10.5517/ccdc.csd.cc29hy0s
_database_code_depnum_ccdc_archive 'CCDC 2130475'
loop_
_audit_author_name
_audit_author_address
'Aleksandra Puzyk'
;SPbU
Russia
;
_audit_update_record             
;
2021-12-22 deposited with the CCDC.	2022-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-12-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
N,N,1-trimethyl-4-(naphthalen-1-yl)-1,2,3,4-tetrahydrobenzo[h]quinazolin-10-amine
_chemical_formula_moiety         'C25 H25 N3'
_chemical_formula_sum            'C25 H25 N3'
_chemical_formula_weight         367.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H25 N3'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9740(3)
_cell_length_b                   10.1567(3)
_cell_length_c                   11.2275(3)
_cell_angle_alpha                72.713(2)
_cell_angle_beta                 89.359(2)
_cell_angle_gamma                80.928(2)
_cell_volume                     964.20(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8061
_cell_measurement_temperature    99.8(9)
_cell_measurement_theta_max      78.1100
_cell_measurement_theta_min      4.1410
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11725
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.996
_diffrn_reflns_theta_min         4.127
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00 119.00   0.50    0.18    --   47.10  57.00 -30.00  170
  2  ω     86.00 159.00   0.50    0.80    --  113.25 103.00 -80.00  146
  3  ω    100.00 177.00   0.50    0.80    --  113.25  61.00 -30.00  154
  4  ω    130.00 168.00   0.50    0.80    --  113.25  45.00   0.00   76
  5  ω    102.00 173.00   0.50    0.80    --  113.25  15.00  90.00  142
  6  ω   -104.00 -33.00   0.50    0.80    -- -106.00  77.00 120.00  142
  7  ω    -71.00 -39.00   0.50    0.80    -- -106.00  61.00  60.00   64
  8  ω    -68.00 -43.00   0.50    0.80    -- -106.00  61.00  90.00   50
  9  ω    -80.00 -34.00   0.50    0.80    -- -106.00 125.00 120.00   92
 10  ω   -108.00 -82.00   0.50    0.80    -- -106.00 125.00 120.00   52
 11  ω   -112.00 -86.00   0.50    0.80    -- -106.00 125.00  60.00   52
 12  ω    -61.00 -36.00   0.50    0.80    -- -106.00 125.00  60.00   50
 13  ω    -58.00 -33.00   0.50    0.80    -- -106.00 110.00  21.40   50
 14  ω   -108.00 -73.00   0.50    0.80    -- -106.00 110.00  21.40   70
 15  ω   -106.00 -64.00   0.50    0.80    -- -106.00 108.00 119.29   84
 16  ω   -112.00 -38.00   0.50    0.80    -- -106.00 125.00 -60.00  148
 17  ω   -109.00 -82.00   0.50    0.80    -- -106.00 125.00 -90.00   54
 18  ω    -67.00 -35.00   0.50    0.80    -- -106.00 125.00 -90.00   64
 19  ω    -61.00 -36.00   0.50    0.80    -- -106.00 106.00-159.81   50
 20  ω   -107.00 -81.00   0.50    0.80    -- -106.00 106.00-159.81   52
 21  ω   -106.00 -73.00   0.50    0.80    -- -106.00 103.00 -80.00   66
 22  ω    -64.00 -24.00   0.50    0.18    --  -47.10 103.00 -80.00   80
 23  ω   -154.00 -93.00   0.50    0.80    -- -106.00 -30.00-120.00  122
 24  ω   -174.00-119.00   0.50    0.80    -- -106.00 -45.00-150.00  110
 25  ω   -175.00-120.00   0.50    0.80    -- -106.00 -45.00 -60.00  110
 26  ω   -140.00 -85.00   0.50    0.80    -- -106.00-103.00 176.00  110
 27  ω   -105.00 -78.00   0.50    0.18    --  -47.10-125.00 -30.00   54
 28  ω   -114.00 -73.00   0.50    0.18    --  -47.10-125.00 -60.00   82
 29  ω    -22.00  25.00   0.50    0.18    --   47.10 -19.00  90.00   94
 30  ω     42.00  67.00   0.50    0.80    --  113.25 -61.00  60.00   50
 31  ω     43.00  69.00   0.50    0.80    --  113.25 -61.00   0.00   52
 32  ω     43.00  70.00   0.50    0.80    --  113.25 -61.00 -30.00   54
 33  ω    -24.00  62.00   0.50    0.18    --   47.10 -57.00-150.00  172
 34  ω     45.00 105.00   0.50    0.80    --  113.25 -77.00-180.00  120
 35  ω     46.00  71.00   0.50    0.80    --  113.25 -61.00-150.00   50
 36  ω     48.00  92.00   0.50    0.18    --   47.10-125.00-180.00   88
 37  ω     43.00 108.00   0.50    0.80    --  113.25-125.00 -60.00  130
 38  ω     43.00  82.00   0.50    0.80    --  113.25-125.00 -30.00   78
 39  ω     48.00  77.00   0.50    0.80    --  113.25 -94.00-180.00   58
 40  ω     52.00 105.00   0.50    0.80    --  113.25 -94.00   0.00  106
 41  ω     79.00 106.00   0.50    0.80    --  113.25 -94.00-180.00   54
 42  ω     70.00 108.00   0.50    0.80    --  113.25-111.00  16.51   76
 43  ω     -5.00  81.00   0.50    0.18    --   47.10-103.00 176.00  172
 44  ω     53.00  79.00   0.50    0.80    --  113.25-103.00 176.00   52
 45  ω     62.00 102.00   0.50    0.80    --  113.25 -94.00 120.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0658300000
_diffrn_orient_matrix_UB_12      -0.0772107000
_diffrn_orient_matrix_UB_13      -0.0927306000
_diffrn_orient_matrix_UB_21      -0.1142470000
_diffrn_orient_matrix_UB_22      0.0970646000
_diffrn_orient_matrix_UB_23      -0.1021161000
_diffrn_orient_matrix_UB_31      0.1134861000
_diffrn_orient_matrix_UB_32      0.1026123000
_diffrn_orient_matrix_UB_33      -0.0406702000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3214
_reflns_number_total             3647
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+0.2484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C16(H16), C21(H21), C9(H9), C5(H5), C15(H15), C6(H6), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
N2 N 0.59916(11) 0.15591(11) 0.67851(10) 0.0196(2) Uani 1 1 d . . . . .
N3 N 0.46331(12) -0.06871(11) 0.80314(10) 0.0221(2) Uani 1 1 d . . . . .
N1 N 0.71088(12) 0.35781(11) 0.58177(10) 0.0231(3) Uani 1 1 d . . . . .
H1 H 0.799(2) 0.3914(17) 0.5589(15) 0.028 Uiso 1 1 d . U . . .
C11 C 0.47675(13) 0.38118(13) 0.69232(11) 0.0192(3) Uani 1 1 d . . . . .
C13 C 0.69122(13) 0.50046(12) 0.73143(11) 0.0196(3) Uani 1 1 d . . . . .
C22 C 0.78743(13) 0.60378(12) 0.68652(12) 0.0199(3) Uani 1 1 d . . . . .
C3 C 0.34469(13) 0.17906(12) 0.76686(11) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.33588(14) 0.03113(13) 0.80539(11) 0.0205(3) Uani 1 1 d . . . . .
C17 C 0.86185(14) 0.65039(13) 0.77463(12) 0.0210(3) Uani 1 1 d . . . . .
C8 C 0.21523(14) 0.27192(13) 0.78465(11) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.47430(13) 0.23985(12) 0.71201(11) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.34931(14) 0.46805(13) 0.71818(12) 0.0216(3) Uani 1 1 d . . . . .
H10 H 0.3533 0.5639 0.7067 0.026 Uiso 1 1 calc R U . . .
C7 C 0.07882(14) 0.22208(14) 0.82650(12) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.73523(14) 0.21716(13) 0.66862(12) 0.0224(3) Uani 1 1 d . . . . .
H1A H 0.8175 0.1584 0.6394 0.027 Uiso 1 1 calc R U . . .
H1B H 0.7665 0.2204 0.7518 0.027 Uiso 1 1 calc R U . . .
C16 C 0.84041(14) 0.59288(13) 0.90399(12) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.8891 0.6241 0.9628 0.028 Uiso 1 1 calc R U . . .
C21 C 0.81137(14) 0.66457(13) 0.55740(12) 0.0231(3) Uani 1 1 d . . . . .
H21 H 0.7625 0.6358 0.4970 0.028 Uiso 1 1 calc R U . . .
C14 C 0.67583(14) 0.44744(13) 0.85768(12) 0.0221(3) Uani 1 1 d . . . . .
C12 C 0.60984(14) 0.45119(13) 0.63703(11) 0.0202(3) Uani 1 1 d . . . . .
H12 H 0.5686 0.5363 0.5673 0.024 Uiso 1 1 calc R U . . .
C9 C 0.22133(14) 0.41645(13) 0.75915(12) 0.0225(3) Uani 1 1 d . . . . .
H9 H 0.1348 0.4777 0.7709 0.027 Uiso 1 1 calc R U . . .
C5 C 0.19947(15) -0.01123(14) 0.84412(12) 0.0245(3) Uani 1 1 d . . . . .
H5 H 0.1928 -0.1079 0.8659 0.029 Uiso 1 1 calc R U . . .
C15 C 0.75057(15) 0.49338(14) 0.94450(12) 0.0248(3) Uani 1 1 d . . . . .
H15 H 0.7380 0.4547 1.0314 0.030 Uiso 1 1 calc R U . . .
C6 C 0.07088(15) 0.08337(14) 0.85237(12) 0.0262(3) Uani 1 1 d . . . . .
H6 H -0.0219 0.0509 0.8760 0.031 Uiso 1 1 calc R U . . .
C18 C 0.95583(15) 0.75312(13) 0.73141(13) 0.0254(3) Uani 1 1 d . . . . .
H18 H 1.0049 0.7844 0.7900 0.030 Uiso 1 1 calc R U . . .
C23 C 0.57049(15) 0.10894(14) 0.57065(12) 0.0247(3) Uani 1 1 d . . . . .
H23A H 0.4697 0.0826 0.5752 0.037 Uiso 1 1 calc R U . . .
H23B H 0.6464 0.0280 0.5711 0.037 Uiso 1 1 calc R U . . .
H23C H 0.5763 0.1848 0.4936 0.037 Uiso 1 1 calc R U . . .
C19 C 0.97716(15) 0.80818(14) 0.60659(14) 0.0280(3) Uani 1 1 d . . . . .
H19 H 1.0415 0.8763 0.5792 0.034 Uiso 1 1 calc R U . . .
C25 C 0.43648(17) -0.20421(13) 0.79807(13) 0.0287(3) Uani 1 1 d . . . . .
H25A H 0.4058 -0.2578 0.8799 0.043 Uiso 1 1 calc R U . . .
H25B H 0.5293 -0.2550 0.7756 0.043 Uiso 1 1 calc R U . . .
H25C H 0.3562 -0.1914 0.7353 0.043 Uiso 1 1 calc R U . . .
C24 C 0.58944(15) -0.08286(14) 0.88988(13) 0.0270(3) Uani 1 1 d . . . . .
H24A H 0.5938 0.0078 0.9027 0.041 Uiso 1 1 calc R U . . .
H24B H 0.6841 -0.1148 0.8551 0.041 Uiso 1 1 calc R U . . .
H24C H 0.5749 -0.1511 0.9699 0.041 Uiso 1 1 calc R U . . .
C20 C 0.90328(15) 0.76358(14) 0.51866(13) 0.0274(3) Uani 1 1 d . . . . .
H20 H 0.9175 0.8025 0.4321 0.033 Uiso 1 1 calc R U . . .
H14 H 0.6070(16) 0.3799(15) 0.8896(14) 0.017(3) Uiso 1 1 d . . . . .
H7 H -0.0133(19) 0.2893(18) 0.8392(16) 0.031(4) 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 C2 1.4155(16) . ?
N2 C1 1.4442(15) . ?
N2 C23 1.4661(15) . ?
N3 C4 1.4090(16) . ?
N3 C25 1.4514(16) . ?
N3 C24 1.4630(17) . ?
N1 H1 0.911(18) . ?
N1 C1 1.4552(17) . ?
N1 C12 1.4740(16) . ?
C11 C2 1.3897(17) . ?
C11 C10 1.4132(18) . ?
C11 C12 1.5186(16) . ?
C13 C22 1.4362(17) . ?
C13 C14 1.3725(18) . ?
C13 C12 1.5345(16) . ?
C22 C17 1.4288(17) . ?
C22 C21 1.4254(18) . ?
C3 C4 1.4496(17) . ?
C3 C8 1.4285(18) . ?
C3 C2 1.4484(17) . ?
C4 C5 1.3842(18) . ?
C17 C16 1.4187(18) . ?
C17 C18 1.4152(18) . ?
C8 C7 1.4201(18) . ?
C8 C9 1.4194(18) . ?
C10 H10 0.9500 . ?
C10 C9 1.3564(18) . ?
C7 C6 1.3646(19) . ?
C7 H7 1.023(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C15 1.3615(19) . ?
C21 H21 0.9500 . ?
C21 C20 1.3690(18) . ?
C14 C15 1.4148(18) . ?
C14 H14 0.982(15) . ?
C12 H12 1.0000 . ?
C9 H9 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.4016(19) . ?
C15 H15 0.9500 . ?
C6 H6 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.369(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.4122(19) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C20 H20 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
C2 N2 C1 112.35(9) . . ?
C2 N2 C23 114.79(10) . . ?
C1 N2 C23 112.72(10) . . ?
C4 N3 C25 117.33(10) . . ?
C4 N3 C24 116.76(10) . . ?
C25 N3 C24 111.24(11) . . ?
C1 N1 H1 112.9(11) . . ?
C1 N1 C12 109.28(10) . . ?
C12 N1 H1 111.0(10) . . ?
C2 C11 C10 120.28(11) . . ?
C2 C11 C12 122.77(11) . . ?
C10 C11 C12 116.88(11) . . ?
C22 C13 C12 119.10(11) . . ?
C14 C13 C22 119.08(11) . . ?
C14 C13 C12 121.81(11) . . ?
C17 C22 C13 118.94(11) . . ?
C21 C22 C13 123.31(11) . . ?
C21 C22 C17 117.74(11) . . ?
C8 C3 C4 117.28(11) . . ?
C8 C3 C2 117.57(11) . . ?
C2 C3 C4 125.15(11) . . ?
N3 C4 C3 120.95(11) . . ?
C5 C4 N3 120.11(11) . . ?
C5 C4 C3 118.94(12) . . ?
C16 C17 C22 119.47(11) . . ?
C18 C17 C22 119.45(12) . . ?
C18 C17 C16 121.08(11) . . ?
C7 C8 C3 120.91(11) . . ?
C9 C8 C3 119.99(11) . . ?
C9 C8 C7 119.09(12) . . ?
N2 C2 C3 120.34(10) . . ?
C11 C2 N2 119.64(11) . . ?
C11 C2 C3 120.02(11) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 120.92(11) . . ?
C9 C10 H10 119.5 . . ?
C8 C7 H7 120.4(9) . . ?
C6 C7 C8 120.03(12) . . ?
C6 C7 H7 119.6(9) . . ?
N2 C1 N1 110.71(10) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
C17 C16 H16 119.7 . . ?
C15 C16 C17 120.55(11) . . ?
C15 C16 H16 119.7 . . ?
C22 C21 H21 119.3 . . ?
C20 C21 C22 121.36(12) . . ?
C20 C21 H21 119.3 . . ?
C13 C14 C15 121.70(11) . . ?
C13 C14 H14 120.0(9) . . ?
C15 C14 H14 118.2(9) . . ?
N1 C12 C11 109.47(10) . . ?
N1 C12 C13 113.25(10) . . ?
N1 C12 H12 107.1 . . ?
C11 C12 C13 112.37(10) . . ?
C11 C12 H12 107.1 . . ?
C13 C12 H12 107.1 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.77(12) . . ?
C10 C9 H9 119.6 . . ?
C4 C5 H5 118.8 . . ?
C4 C5 C6 122.34(12) . . ?
C6 C5 H5 118.8 . . ?
C16 C15 C14 120.24(12) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C7 C6 C5 120.08(12) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.11(12) . . ?
C19 C18 H18 119.4 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.90(12) . . ?
C20 C19 H19 120.1 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C20 C19 120.43(12) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?

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
N3 C4 C5 C6 177.64(11) . . . . ?
C11 C10 C9 C8 4.00(19) . . . . ?
C13 C22 C17 C16 0.62(17) . . . . ?
C13 C22 C17 C18 -179.42(11) . . . . ?
C13 C22 C21 C20 179.52(12) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C22 C13 C14 C15 0.91(18) . . . . ?
C22 C13 C12 N1 74.11(14) . . . . ?
C22 C13 C12 C11 -161.20(11) . . . . ?
C22 C17 C16 C15 0.43(19) . . . . ?
C22 C17 C18 C19 -0.29(19) . . . . ?
C22 C21 C20 C19 0.0(2) . . . . ?
C3 C4 C5 C6 -2.70(18) . . . . ?
C3 C8 C7 C6 1.13(19) . . . . ?
C3 C8 C9 C10 -0.19(18) . . . . ?
C4 C3 C8 C7 -6.23(17) . . . . ?
C4 C3 C8 C9 174.45(11) . . . . ?
C4 C3 C2 N2 7.46(17) . . . . ?
C4 C3 C2 C11 -172.36(11) . . . . ?
C4 C5 C6 C7 -2.6(2) . . . . ?
C17 C22 C21 C20 0.45(19) . . . . ?
C17 C16 C15 C14 -0.8(2) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C8 C3 C4 N3 -173.43(10) . . . . ?
C8 C3 C4 C5 6.92(17) . . . . ?
C8 C3 C2 N2 -172.62(10) . . . . ?
C8 C3 C2 C11 7.55(16) . . . . ?
C8 C7 C6 C5 3.41(19) . . . . ?
C2 N2 C1 N1 -55.27(13) . . . . ?
C2 C11 C10 C9 -1.85(18) . . . . ?
C2 C11 C12 N1 13.84(16) . . . . ?
C2 C11 C12 C13 -112.91(13) . . . . ?
C2 C3 C4 N3 6.49(18) . . . . ?
C2 C3 C4 C5 -173.17(11) . . . . ?
C2 C3 C8 C7 173.85(11) . . . . ?
C2 C3 C8 C9 -5.47(17) . . . . ?
C10 C11 C2 N2 176.13(10) . . . . ?
C10 C11 C2 C3 -4.05(17) . . . . ?
C10 C11 C12 N1 -163.14(10) . . . . ?
C10 C11 C12 C13 70.12(14) . . . . ?
C7 C8 C9 C10 -179.53(11) . . . . ?
C1 N2 C2 C11 20.72(15) . . . . ?
C1 N2 C2 C3 -159.10(11) . . . . ?
C1 N1 C12 C11 -45.98(13) . . . . ?
C1 N1 C12 C13 80.26(12) . . . . ?
C16 C17 C18 C19 179.68(12) . . . . ?
C21 C22 C17 C16 179.73(11) . . . . ?
C21 C22 C17 C18 -0.30(18) . . . . ?
C14 C13 C22 C17 -1.27(17) . . . . ?
C14 C13 C22 C21 179.67(11) . . . . ?
C14 C13 C12 N1 -105.20(13) . . . . ?
C14 C13 C12 C11 19.48(16) . . . . ?
C12 N1 C1 N2 69.83(12) . . . . ?
C12 C11 C2 N2 -0.74(17) . . . . ?
C12 C11 C2 C3 179.08(10) . . . . ?
C12 C11 C10 C9 175.21(11) . . . . ?
C12 C13 C22 C17 179.40(10) . . . . ?
C12 C13 C22 C21 0.34(18) . . . . ?
C12 C13 C14 C15 -179.78(12) . . . . ?
C9 C8 C7 C6 -179.54(12) . . . . ?
C18 C17 C16 C15 -179.54(12) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C23 N2 C2 C11 -109.82(12) . . . . ?
C23 N2 C2 C3 70.36(14) . . . . ?
C23 N2 C1 N1 76.32(13) . . . . ?
C25 N3 C4 C3 -158.07(11) . . . . ?
C25 N3 C4 C5 21.58(17) . . . . ?
C24 N3 C4 C3 66.08(15) . . . . ?
C24 N3 C4 C5 -114.27(13) . . . . ?

_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 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.784
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
