# 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_x2
_database_code_depnum_ccdc_archive 'CCDC 2131274'
loop_
_audit_author_name
_audit_author_address
'Huawen Huang'
;Xiangtan University
China
;
_audit_update_record             
;
2021-12-28 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N3 O2'
_chemical_formula_sum            'C19 H19 N3 O2'
_chemical_formula_weight         321.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.5358(4)
_cell_length_b                   9.3335(3)
_cell_length_c                   20.6119(9)
_cell_angle_alpha                95.328(3)
_cell_angle_beta                 91.723(4)
_cell_angle_gamma                90.573(3)
_cell_volume                     1634.16(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3945
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.5440
_cell_measurement_theta_min      2.1760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11022
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.965
_diffrn_reflns_theta_min         4.311
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -13.00   1.00    2.00    --  -40.73 125.00   0.00   76
  2  ω   -115.00   0.00   1.00    2.00    --  -40.73 -19.00 -90.00  115
  3  ω     23.00  50.00   1.00    2.00    --   40.73-125.00-180.00   27
  4  ω     23.00  54.00   1.00    2.00    --   40.73-125.00-150.00   31
  5  ω     47.00  86.00   1.00    2.00    --   40.73-125.00 -90.00   39
  6  ω     63.00 135.00   1.00    4.00    --  107.58 -61.00   0.00   72
  7  ω     82.00 177.00   1.00    4.00    --  107.58  30.00  90.00   95
  8  ω    106.00 133.00   1.00    4.00    --  107.58 125.00   0.00   27
  9  ω    109.00 147.00   1.00    4.00    --  107.58  45.00 -30.00   38
 10  ω     57.00  84.00   1.00    4.00    --  107.58 -45.00-150.00   27
 11  ω     83.00 108.00   1.00    4.00    --  107.58 -94.00-180.00   25
 12  ω     73.00 116.00   1.00    4.00    --  107.58-125.00-180.00   43
 13  ω     35.00 131.00   1.00    4.00    --  107.58 -45.00 -90.00   96
 14  ω     63.00 109.00   1.00    4.00    --  107.58 -94.00   0.00   46
 15  ω     44.00 156.00   1.00    4.00    --  107.58 -15.00  60.00  112
 16  ω     36.00 125.00   1.00    4.00    --  107.58 -61.00 120.00   89
 17  ω     33.00  58.00   1.00    4.00    --  107.58 -94.00  90.00   25
 18  ω     26.00 107.00   1.00    4.00    --  107.58 -94.00 -90.00   81
 19  ω   -115.00 -31.00   1.00    2.00    --  -40.73 -38.00-150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0683751000
_diffrn_orient_matrix_UB_12      0.0815004000
_diffrn_orient_matrix_UB_13      -0.0558044000
_diffrn_orient_matrix_UB_21      0.0153963000
_diffrn_orient_matrix_UB_22      -0.1360239000
_diffrn_orient_matrix_UB_23      -0.0476527000
_diffrn_orient_matrix_UB_31      -0.1664216000
_diffrn_orient_matrix_UB_32      -0.0483825000
_diffrn_orient_matrix_UB_33      0.0159818000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5014
_reflns_number_total             6398
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         6398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.037
_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)+(0.0486P)²+0.3408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1219
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C18(H18A,H18B), C27(H27A,H27B), C28(H28A,H28B),
 C37(H37A,H37B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C29(H29),
  C32(H32), C33(H33), C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 1.45639(14) 0.77156(13) 0.42076(6) 0.0395(3) Uani 1 1 d . . . . .
O2 O 0.40662(14) 0.89174(16) 0.07003(6) 0.0459(3) Uani 1 1 d . . . . .
N1 N 1.16884(18) 0.92188(17) 0.27747(8) 0.0413(4) Uani 1 1 d . . . . .
N2 N 1.2072(2) 1.04762(19) 0.25662(8) 0.0465(4) Uani 1 1 d . . . . .
N3 N 1.03240(18) 0.86506(17) 0.25406(7) 0.0402(3) Uani 1 1 d . . . . .
C1 C 1.34009(17) 0.89263(16) 0.51219(8) 0.0283(3) Uani 1 1 d . . . . .
C2 C 1.23335(18) 0.99281(17) 0.53773(9) 0.0320(3) Uani 1 1 d . . . . .
H2 H 1.170776 1.042457 0.509901 0.038 Uiso 1 1 calc R U . . .
C3 C 1.22023(19) 1.01867(18) 0.60480(9) 0.0359(4) Uani 1 1 d . . . . .
H3 H 1.149384 1.086203 0.621776 0.043 Uiso 1 1 calc R U . . .
C4 C 1.3121(2) 0.94438(19) 0.64645(9) 0.0385(4) Uani 1 1 d . . . . .
H4 H 1.300957 0.960167 0.691275 0.046 Uiso 1 1 calc R U . . .
C5 C 1.4210(2) 0.84626(19) 0.62137(9) 0.0370(4) Uani 1 1 d . . . . .
H5 H 1.484229 0.797558 0.649335 0.044 Uiso 1 1 calc R U . . .
C6 C 1.43500(18) 0.82143(17) 0.55505(9) 0.0323(3) Uani 1 1 d . . . . .
H6 H 1.508704 0.756285 0.538421 0.039 Uiso 1 1 calc R U . . .
C7 C 1.35744(17) 0.85614(16) 0.44082(8) 0.0299(3) Uani 1 1 d . . . . .
C8 C 1.24731(18) 0.92241(18) 0.39322(8) 0.0316(3) Uani 1 1 d . . . . .
H8A H 1.139862 0.908843 0.405667 0.038 Uiso 1 1 calc R U . . .
H8B H 1.268389 1.025012 0.394809 0.038 Uiso 1 1 calc R U . . .
C9 C 1.2676(2) 0.8546(2) 0.32489(10) 0.0474(5) Uani 1 1 d . . . . .
H9A H 1.376522 0.863375 0.313575 0.057 Uiso 1 1 calc R U . . .
H9B H 1.241263 0.752914 0.323016 0.057 Uiso 1 1 calc R U . . .
C10 C 1.0862(2) 1.0738(2) 0.21695(9) 0.0442(4) Uani 1 1 d . . . . .
H10 H 1.076119 1.155044 0.194343 0.053 Uiso 1 1 calc R U . . .
C11 C 0.9777(2) 0.96093(19) 0.21457(8) 0.0358(4) Uani 1 1 d . . . . .
C12 C 0.8289(2) 0.93873(19) 0.17717(8) 0.0359(4) Uani 1 1 d . . . . .
C13 C 0.7989(2) 1.0107(2) 0.12164(9) 0.0389(4) Uani 1 1 d . . . . .
H13 H 0.874822 1.072527 0.108016 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6583(2) 0.9914(2) 0.08667(9) 0.0411(4) Uani 1 1 d . . . . .
H14 H 0.640890 1.039163 0.049511 0.049 Uiso 1 1 calc R U . . .
C15 C 0.5430(2) 0.9008(2) 0.10699(9) 0.0384(4) Uani 1 1 d . . . . .
C16 C 0.5704(2) 0.8268(2) 0.16143(9) 0.0411(4) Uani 1 1 d . . . . .
H16 H 0.494441 0.764784 0.174850 0.049 Uiso 1 1 calc R U . . .
C17 C 0.7130(2) 0.8467(2) 0.19570(9) 0.0400(4) Uani 1 1 d . . . . .
H17 H 0.731308 0.796779 0.232138 0.048 Uiso 1 1 calc R U . . .
C18 C 0.2781(2) 0.8139(2) 0.09319(10) 0.0461(5) Uani 1 1 d . . . . .
H18A H 0.257592 0.848501 0.137935 0.055 Uiso 1 1 calc R U . . .
H18B H 0.301410 0.712178 0.091463 0.055 Uiso 1 1 calc R U . . .
C19 C 0.1383(2) 0.8382(3) 0.04960(11) 0.0543(5) Uani 1 1 d . . . . .
H19A H 0.158683 0.800373 0.005790 0.081 Uiso 1 1 calc R U . . .
H19B H 0.118849 0.939487 0.050541 0.081 Uiso 1 1 calc R U . . .
H19C H 0.048177 0.790234 0.064624 0.081 Uiso 1 1 calc R U . . .
O3 O 0.98394(14) 0.68492(13) 0.41969(6) 0.0388(3) Uani 1 1 d . . . . .
O4 O -0.07518(14) 0.41868(16) 0.07785(7) 0.0463(3) Uani 1 1 d . . . . .
N4 N 0.70281(18) 0.46518(17) 0.27511(7) 0.0394(3) Uani 1 1 d . . . . .
N5 N 0.7355(2) 0.33118(18) 0.25333(9) 0.0478(4) Uani 1 1 d . . . . .
N6 N 0.56556(17) 0.51400(16) 0.25430(7) 0.0386(3) Uani 1 1 d . . . . .
C20 C 0.84817(17) 0.61840(16) 0.51066(8) 0.0288(3) Uani 1 1 d . . . . .
C21 C 0.73065(18) 0.53775(17) 0.53590(9) 0.0322(3) Uani 1 1 d . . . . .
H21 H 0.665617 0.478162 0.507931 0.039 Uiso 1 1 calc R U . . .
C22 C 0.71001(19) 0.54574(19) 0.60248(9) 0.0365(4) Uani 1 1 d . . . . .
H22 H 0.632001 0.490701 0.619136 0.044 Uiso 1 1 calc R U . . .
C23 C 0.8054(2) 0.63565(19) 0.64440(9) 0.0374(4) Uani 1 1 d . . . . .
H23 H 0.789334 0.643094 0.689003 0.045 Uiso 1 1 calc R U . . .
C24 C 0.9247(2) 0.71443(18) 0.61974(9) 0.0370(4) Uani 1 1 d . . . . .
H24 H 0.989990 0.773388 0.647895 0.044 Uiso 1 1 calc R U . . .
C25 C 0.94672(18) 0.70542(17) 0.55355(9) 0.0323(3) Uani 1 1 d . . . . .
H25 H 1.027685 0.757575 0.537260 0.039 Uiso 1 1 calc R U . . .
C26 C 0.87387(18) 0.61844(16) 0.43929(8) 0.0303(3) Uani 1 1 d . . . . .
C27 C 0.75896(18) 0.53820(18) 0.39128(8) 0.0333(4) Uani 1 1 d . . . . .
H27A H 0.655241 0.577999 0.397098 0.040 Uiso 1 1 calc R U . . .
H27B H 0.754327 0.437773 0.399769 0.040 Uiso 1 1 calc R U . . .
C28 C 0.8069(2) 0.5490(2) 0.32174(9) 0.0418(4) Uani 1 1 d . . . . .
H28A H 0.805439 0.649103 0.312569 0.050 Uiso 1 1 calc R U . . .
H28B H 0.913172 0.514869 0.316779 0.050 Uiso 1 1 calc R U . . .
C29 C 0.6106(2) 0.2906(2) 0.21535(10) 0.0458(4) Uani 1 1 d . . . . .
H29 H 0.596568 0.200635 0.192349 0.055 Uiso 1 1 calc R U . . .
C30 C 0.5045(2) 0.40266(19) 0.21521(8) 0.0359(4) Uani 1 1 d . . . . .
C31 C 0.3535(2) 0.41063(19) 0.17970(8) 0.0345(4) Uani 1 1 d . . . . .
C32 C 0.3155(2) 0.3141(2) 0.12566(9) 0.0388(4) Uani 1 1 d . . . . .
H32 H 0.387271 0.244420 0.111679 0.047 Uiso 1 1 calc R U . . .
C33 C 0.1728(2) 0.3205(2) 0.09252(9) 0.0405(4) Uani 1 1 d . . . . .
H33 H 0.150073 0.256051 0.056212 0.049 Uiso 1 1 calc R U . . .
C34 C 0.0628(2) 0.4230(2) 0.11321(9) 0.0372(4) Uani 1 1 d . . . . .
C35 C 0.0985(2) 0.5201(2) 0.16679(9) 0.0391(4) Uani 1 1 d . . . . .
H35 H 0.026288 0.589184 0.180988 0.047 Uiso 1 1 calc R U . . .
C36 C 0.2433(2) 0.51318(19) 0.19915(9) 0.0383(4) Uani 1 1 d . . . . .
H36 H 0.266991 0.579108 0.234829 0.046 Uiso 1 1 calc R U . . .
C37 C -0.1930(2) 0.5202(2) 0.09764(10) 0.0465(5) Uani 1 1 d . . . . .
H37A H -0.154499 0.617672 0.095232 0.056 Uiso 1 1 calc R U . . .
H37B H -0.221590 0.509726 0.142154 0.056 Uiso 1 1 calc R U . . .
C38 C -0.3325(2) 0.4894(3) 0.05180(12) 0.0573(6) Uani 1 1 d . . . . .
H38A H -0.302789 0.501061 0.008025 0.086 Uiso 1 1 calc R U . . .
H38B H -0.414807 0.555089 0.063785 0.086 Uiso 1 1 calc R U . . .
H38C H -0.368729 0.392480 0.054381 0.086 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
O1 C7 1.217(2) . ?
O2 C15 1.369(2) . ?
O2 C18 1.428(2) . ?
N1 N2 1.328(2) . ?
N1 N3 1.333(2) . ?
N1 C9 1.461(2) . ?
N2 C10 1.336(2) . ?
N3 C11 1.342(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.491(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.516(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.505(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C11 1.392(3) . ?
C11 C12 1.469(2) . ?
C12 C13 1.398(2) . ?
C12 C17 1.389(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.391(3) . ?
C15 C16 1.386(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.504(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O3 C26 1.220(2) . ?
O4 C34 1.364(2) . ?
O4 C37 1.431(2) . ?
N4 N5 1.324(2) . ?
N4 N6 1.335(2) . ?
N4 C28 1.456(2) . ?
N5 C29 1.334(2) . ?
N6 C30 1.345(2) . ?
C20 C21 1.390(2) . ?
C20 C25 1.399(2) . ?
C20 C26 1.494(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.386(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.514(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.514(3) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29 0.9300 . ?
C29 C30 1.390(3) . ?
C30 C31 1.469(2) . ?
C31 C32 1.394(2) . ?
C31 C36 1.390(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.383(2) . ?
C33 H33 0.9300 . ?
C33 C34 1.395(3) . ?
C34 C35 1.386(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.392(3) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.506(3) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

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
C15 O2 C18 117.71(14) . . ?
N2 N1 N3 115.41(15) . . ?
N2 N1 C9 121.69(16) . . ?
N3 N1 C9 122.85(16) . . ?
N1 N2 C10 103.19(15) . . ?
N1 N3 C11 104.06(15) . . ?
C2 C1 C6 118.92(16) . . ?
C2 C1 C7 123.02(14) . . ?
C6 C1 C7 118.06(14) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.00(15) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.28(16) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.05(17) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.72(16) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.00(16) . . ?
C5 C6 H6 119.5 . . ?
O1 C7 C1 120.63(15) . . ?
O1 C7 C8 120.07(16) . . ?
C1 C7 C8 119.28(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 C7 110.77(14) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
N1 C9 C8 111.91(15) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 H10 125.1 . . ?
N2 C10 C11 109.74(17) . . ?
C11 C10 H10 125.1 . . ?
N3 C11 C10 107.60(16) . . ?
N3 C11 C12 122.26(17) . . ?
C10 C11 C12 130.14(16) . . ?
C13 C12 C11 120.82(16) . . ?
C17 C12 C11 121.46(16) . . ?
C17 C12 C13 117.72(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.06(17) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.09(17) . . ?
C15 C14 H14 120.0 . . ?
O2 C15 C14 115.62(16) . . ?
O2 C15 C16 124.38(17) . . ?
C16 C15 C14 120.00(17) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.08(17) . . ?
C17 C16 H16 120.5 . . ?
C12 C17 C16 122.03(17) . . ?
C12 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
O2 C18 H18A 110.3 . . ?
O2 C18 H18B 110.3 . . ?
O2 C18 C19 106.96(16) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C34 O4 C37 118.02(15) . . ?
N5 N4 N6 115.59(15) . . ?
N5 N4 C28 121.42(15) . . ?
N6 N4 C28 122.89(16) . . ?
N4 N5 C29 103.10(15) . . ?
N4 N6 C30 103.88(15) . . ?
C21 C20 C25 119.06(16) . . ?
C21 C20 C26 123.12(15) . . ?
C25 C20 C26 117.82(14) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.29(16) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.14(16) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.93(17) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.03(16) . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.50(15) . . ?
C24 C25 H25 119.7 . . ?
O3 C26 C20 120.61(15) . . ?
O3 C26 C27 120.18(16) . . ?
C20 C26 C27 119.19(14) . . ?
C26 C27 H27A 109.4 . . ?
C26 C27 H27B 109.4 . . ?
C26 C27 C28 111.09(14) . . ?
H27A C27 H27B 108.0 . . ?
C28 C27 H27A 109.4 . . ?
C28 C27 H27B 109.4 . . ?
N4 C28 C27 111.76(15) . . ?
N4 C28 H28A 109.3 . . ?
N4 C28 H28B 109.3 . . ?
C27 C28 H28A 109.3 . . ?
C27 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
N5 C29 H29 125.0 . . ?
N5 C29 C30 109.98(17) . . ?
C30 C29 H29 125.0 . . ?
N6 C30 C29 107.44(16) . . ?
N6 C30 C31 122.56(16) . . ?
C29 C30 C31 129.98(17) . . ?
C32 C31 C30 120.86(17) . . ?
C36 C31 C30 121.29(16) . . ?
C36 C31 C32 117.85(16) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 C31 120.98(17) . . ?
C33 C32 H32 119.5 . . ?
C32 C33 H33 119.8 . . ?
C32 C33 C34 120.41(17) . . ?
C34 C33 H33 119.8 . . ?
O4 C34 C33 115.80(16) . . ?
O4 C34 C35 124.76(17) . . ?
C35 C34 C33 119.44(16) . . ?
C34 C35 H35 120.3 . . ?
C34 C35 C36 119.40(17) . . ?
C36 C35 H35 120.3 . . ?
C31 C36 C35 121.90(17) . . ?
C31 C36 H36 119.0 . . ?
C35 C36 H36 119.0 . . ?
O4 C37 H37A 110.3 . . ?
O4 C37 H37B 110.3 . . ?
O4 C37 C38 106.94(17) . . ?
H37A C37 H37B 108.6 . . ?
C38 C37 H37A 110.3 . . ?
C38 C37 H37B 110.3 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

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
O1 C7 C8 C9 7.2(2) . . . . ?
O2 C15 C16 C17 -178.96(18) . . . . ?
N1 N2 C10 C11 -0.5(2) . . . . ?
N1 N3 C11 C10 -0.6(2) . . . . ?
N1 N3 C11 C12 178.75(16) . . . . ?
N2 N1 N3 C11 0.3(2) . . . . ?
N2 N1 C9 C8 78.0(2) . . . . ?
N2 C10 C11 N3 0.7(2) . . . . ?
N2 C10 C11 C12 -178.55(18) . . . . ?
N3 N1 N2 C10 0.1(2) . . . . ?
N3 N1 C9 C8 -99.4(2) . . . . ?
N3 C11 C12 C13 -158.43(18) . . . . ?
N3 C11 C12 C17 21.9(3) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 C7 C8 C9 -171.12(15) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
C2 C1 C7 O1 177.34(15) . . . . ?
C2 C1 C7 C8 -4.3(2) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C6 C1 C2 C3 -1.2(2) . . . . ?
C6 C1 C7 O1 -3.2(2) . . . . ?
C6 C1 C7 C8 175.08(14) . . . . ?
C7 C1 C2 C3 178.18(14) . . . . ?
C7 C1 C6 C5 -177.67(15) . . . . ?
C7 C8 C9 N1 -176.89(15) . . . . ?
C9 N1 N2 C10 -177.48(17) . . . . ?
C9 N1 N3 C11 177.89(16) . . . . ?
C10 C11 C12 C13 20.8(3) . . . . ?
C10 C11 C12 C17 -158.9(2) . . . . ?
C11 C12 C13 C14 -179.27(17) . . . . ?
C11 C12 C17 C16 178.74(17) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C12 C17 C16 -0.9(3) . . . . ?
C13 C14 C15 O2 178.44(17) . . . . ?
C13 C14 C15 C16 -1.6(3) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C15 O2 C18 C19 172.02(17) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
C17 C12 C13 C14 0.4(3) . . . . ?
C18 O2 C15 C14 -172.69(17) . . . . ?
C18 O2 C15 C16 7.4(3) . . . . ?
O3 C26 C27 C28 2.6(2) . . . . ?
O4 C34 C35 C36 179.64(17) . . . . ?
N4 N5 C29 C30 0.0(2) . . . . ?
N4 N6 C30 C29 0.53(19) . . . . ?
N4 N6 C30 C31 -178.14(15) . . . . ?
N5 N4 N6 C30 -0.6(2) . . . . ?
N5 N4 C28 C27 -93.7(2) . . . . ?
N5 C29 C30 N6 -0.4(2) . . . . ?
N5 C29 C30 C31 178.18(18) . . . . ?
N6 N4 N5 C29 0.4(2) . . . . ?
N6 N4 C28 C27 82.5(2) . . . . ?
N6 C30 C31 C32 160.22(17) . . . . ?
N6 C30 C31 C36 -20.5(3) . . . . ?
C20 C21 C22 C23 0.8(2) . . . . ?
C20 C26 C27 C28 -179.03(14) . . . . ?
C21 C20 C25 C24 -1.9(2) . . . . ?
C21 C20 C26 O3 -175.98(15) . . . . ?
C21 C20 C26 C27 5.7(2) . . . . ?
C21 C22 C23 C24 -1.9(3) . . . . ?
C22 C23 C24 C25 1.2(3) . . . . ?
C23 C24 C25 C20 0.8(3) . . . . ?
C25 C20 C21 C22 1.2(2) . . . . ?
C25 C20 C26 O3 4.8(2) . . . . ?
C25 C20 C26 C27 -173.54(14) . . . . ?
C26 C20 C21 C22 -178.06(14) . . . . ?
C26 C20 C25 C24 177.35(15) . . . . ?
C26 C27 C28 N4 176.53(14) . . . . ?
C28 N4 N5 C29 176.83(17) . . . . ?
C28 N4 N6 C30 -176.99(16) . . . . ?
C29 C30 C31 C32 -18.1(3) . . . . ?
C29 C30 C31 C36 161.18(19) . . . . ?
C30 C31 C32 C33 179.37(16) . . . . ?
C30 C31 C36 C35 -178.65(16) . . . . ?
C31 C32 C33 C34 -0.9(3) . . . . ?
C32 C31 C36 C35 0.7(3) . . . . ?
C32 C33 C34 O4 -178.95(17) . . . . ?
C32 C33 C34 C35 0.9(3) . . . . ?
C33 C34 C35 C36 -0.2(3) . . . . ?
C34 O4 C37 C38 -178.65(17) . . . . ?
C34 C35 C36 C31 -0.6(3) . . . . ?
C36 C31 C32 C33 0.0(3) . . . . ?
C37 O4 C34 C33 179.11(17) . . . . ?
C37 O4 C34 C35 -0.8(3) . . . . ?

_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 1.478
_oxdiff_exptl_absorpt_empirical_full_min 0.312
