# Electronic Supplementary Material (ESI) for RSC Mechanochemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_exp_4
_database_code_depnum_ccdc_archive 'CCDC 2287665'
loop_
_audit_author_name
_audit_author_address
'Jevgenija Martonova'
;Tallinn University of Technology
Estonia
;
_audit_update_record             
;
2023-08-09 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT041_exp_4               
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: Checked
;
_vrf_PLAT042_exp_4               
;
PROBLEM: Calc. and Reported MoietyFormula Strings  Differ     Please Check
RESPONSE: Checked
;
_vrf_PLAT077_exp_4               
;
PROBLEM: Unitcell Contains Non-integer Number of Atoms ..     Please Check
RESPONSE: Checked
;
_vrf_PLAT241_exp_4               
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C1 Check
RESPONSE: Checked
;
_vrf_PLAT260_exp_4               
;
PROBLEM: Large Average Ueq of Residue Including       C1A      0.111 Check
RESPONSE: Checked
;
_vrf_PLAT420_exp_4               
;
PROBLEM: D-H Bond Without Acceptor  N1       --H1       .     Please Check
RESPONSE: Checked
;
_vrf_PLAT906_exp_4               
;
PROBLEM: Large K Value in the Analysis of Variance ......      8.352 Check
RESPONSE: Checked
;
_vrf_PLAT911_exp_4               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.596         18 Report
RESPONSE: Checked
;
# Added during the CSD deposition process: Wednesday 09 August 2023 10:06 AM
# end Validation Reply Form

_audit_creation_date             2023-08-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20.957 N5 O1.986, C0.915 H2.84 O0.096'
_chemical_formula_sum            'C24.92 H23.81 N5 O2.09'
_chemical_formula_weight         426.71
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H21 N5 O2'
_chemical_oxdiff_usercomment     MeOH
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_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                   14.3819(4)
_cell_length_b                   15.9349(5)
_cell_length_c                   9.4755(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.199(3)
_cell_angle_gamma                90
_cell_volume                     2143.61(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3801
_cell_measurement_temperature    123.00
_cell_measurement_theta_max      64.6910
_cell_measurement_theta_min      3.1040
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
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    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_recrystallization_method 'Methanol evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13786
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.747
_diffrn_reflns_theta_max         66.747
_diffrn_reflns_theta_min         3.113
_diffrn_ambient_temperature      123.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  93.00   1.00    8.00    --    5.00  50.00  60.00   45
  2  ω    -80.00  22.00   1.00    8.00    --    5.00  50.00  60.00  102
  3  ω   -178.00-105.00   1.00   32.00    --  -90.00  60.00 107.03   73
  4  ω   -179.00  -1.00   1.00   32.00    --  -90.00  40.00-120.00  178
  5  ω   -104.00 -73.00   1.00   32.00    --  -90.00  58.00 178.52   31
  6  ω    -36.00 -10.00   1.00   32.00    --  -90.00  58.00 178.52   26
  7  ω    -45.00  -2.00   1.00   32.00    --  -90.00  60.00  38.38   43
  8  ω   -111.00 -86.00   1.00   32.00    --  -90.00  60.00 153.60   25
  9  ω    -74.00 -48.00   1.00   32.00    --  -90.00  40.00 -90.00   26
 10  ω   -174.00-136.00   1.00   32.00    --  -90.00  50.00 120.00   38
 11  ω    -92.00  -1.00   1.00   32.00    --  -90.00  50.00 120.00   91
 12  ω   -142.00-116.00   1.00   32.00    --  -90.00  60.00  -0.98   26
 13  ω    -55.00 -28.00   1.00   32.00    --  -90.00  60.00  -0.98   27
 14  ω   -144.00-102.00   1.00   32.00    --  -90.00  50.00  60.00   42
 15  ω   -152.00-118.00   1.00   32.00    --  -90.00  60.00 153.60   34
 16  ω   -167.00-140.00   1.00   32.00    --  -90.00  60.00  38.38   27
 17  ω    -66.00 -41.00   1.00   32.00    --  -90.00  10.00   0.00   25
 18  ω   -147.00-122.00   1.00   32.00    --  -90.00  40.00 -90.00   25
 19  ω    -35.00  -5.00   1.00   32.00    --  -90.00  20.00  30.00   30
 20  ω   -167.00-142.00   1.00   32.00    --  -90.00  20.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0476963000
_diffrn_orient_matrix_UB_12      0.0868588000
_diffrn_orient_matrix_UB_13      -0.0114571000
_diffrn_orient_matrix_UB_21      0.0963510000
_diffrn_orient_matrix_UB_22      0.0419938000
_diffrn_orient_matrix_UB_23      -0.0010718000
_diffrn_orient_matrix_UB_31      -0.0147065000
_diffrn_orient_matrix_UB_32      -0.0063058000
_diffrn_orient_matrix_UB_33      -0.1642973000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3220
_reflns_number_total             3753
_reflns_odcompleteness_completeness 97.99
_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 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_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         0.209
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0991P)²+0.4370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1786
_refine_ls_wR_factor_ref         0.1881
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C1A-O1A
 1.43 with sigma of 0.02
3. Others
 Sof(C1A)=Sof(H1AC)=Sof(H1AD)=Sof(H1AE)=FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(O2)=Sof(H2A)=FVAR(2)
 Sof(H1BC)=Sof(H1BD)=Sof(O1)=Sof(H1A)=FVAR(3)
 Sof(O1A)=Sof(H1AF)=FVAR(4)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1BC,H1BD), C1(H1AA,H1AB)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C10(H10), C13(H13), C14(H14), C24(H24), C4(H4), C21(H21), C6(H6),
 C17(H17), C3(H3), C18(H18), C23(H23), C7(H7), C22(H22)
4.c Tetrahedral OH refined with riding coordinates:
 O1A(H1AF)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C1A(H1AC,H1AD,H1AE)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
N4 N 0.42225(12) 1.07205(12) 0.3134(2) 0.0623(5) Uani 1 1 d . . . . .
O3 O 0.26471(13) 0.74764(12) -0.0511(2) 0.0835(5) Uani 1 1 d . . . . .
N2 N 0.38515(13) 1.02152(14) 0.0811(2) 0.0723(6) Uani 1 1 d . . . . .
H2 H 0.403372 1.015704 -0.002744 0.087 Uiso 1 1 calc R U . . .
N1 N 0.15218(15) 0.80114(14) 0.0659(3) 0.0736(6) Uani 1 1 d . . . . .
N3 N 0.53753(14) 1.05751(15) 0.1591(2) 0.0769(6) Uani 1 1 d . . . . .
N5 N 0.33104(17) 1.14534(16) 0.6855(3) 0.0883(7) Uani 1 1 d . . . . .
C19 C 0.48923(15) 1.10171(14) 0.4174(3) 0.0619(6) Uani 1 1 d . . . . .
C10 C 0.26785(15) 0.91442(16) 0.0709(2) 0.0631(6) Uani 1 1 d . . . . .
H10 H 0.314919 0.875383 0.054611 0.076 Uiso 1 1 calc R U . . .
C16 C 0.44947(15) 1.05163(15) 0.1898(2) 0.0629(6) Uani 1 1 d . . . . .
C20 C 0.45852(16) 1.12714(14) 0.5528(3) 0.0633(6) Uani 1 1 d . . . . .
C11 C 0.29078(15) 0.99853(16) 0.0909(2) 0.0629(6) Uani 1 1 d . . . . .
C5 C 0.16732(16) 0.65118(16) 0.0488(3) 0.0682(6) Uani 1 1 d . . . . .
C9 C 0.17708(15) 0.88680(16) 0.0745(2) 0.0638(6) Uani 1 1 d . . . . .
C12 C 0.22316(17) 1.05785(16) 0.1107(3) 0.0697(6) Uani 1 1 d . . . . .
C8 C 0.19966(17) 0.73672(16) 0.0155(3) 0.0674(6) Uani 1 1 d . . . . .
C13 C 0.13244(16) 1.02827(18) 0.1129(3) 0.0738(7) Uani 1 1 d . . . . .
H13 H 0.084734 1.067207 0.126877 0.089 Uiso 1 1 calc R U . . .
C14 C 0.10931(16) 0.94532(17) 0.0956(3) 0.0716(6) Uani 1 1 d . . . . .
H14 H 0.046509 0.927672 0.098178 0.086 Uiso 1 1 calc R U . . .
C24 C 0.36481(18) 1.12208(18) 0.5680(3) 0.0766(7) Uani 1 1 d . . . . .
H24 H 0.321565 1.100694 0.490007 0.092 Uiso 1 1 calc R U . . .
C4 C 0.17876(18) 0.58615(18) -0.0442(3) 0.0753(7) Uani 1 1 d . . . . .
H4 H 0.204477 0.596883 -0.128750 0.090 Uiso 1 1 calc R U . . .
C2 C 0.11678(19) 0.48724(19) 0.1105(4) 0.0844(8) Uani 1 1 d . . . . .
C21 C 0.5200(2) 1.15866(19) 0.6675(3) 0.0832(8) Uani 1 1 d . . . . .
H21 H 0.584998 1.164454 0.661386 0.100 Uiso 1 1 calc R U . . .
C6 C 0.13261(19) 0.63248(19) 0.1734(3) 0.0802(7) Uani 1 1 d . . . . .
H6 H 0.125399 0.676027 0.239287 0.096 Uiso 1 1 calc R U . . .
C17 C 0.60173(18) 1.0859(2) 0.2650(3) 0.0885(9) Uani 1 1 d . . . . .
H17 H 0.665081 1.090412 0.249050 0.106 Uiso 1 1 calc R U . . .
C3 C 0.1524(2) 0.50535(19) -0.0130(3) 0.0842(8) Uani 1 1 d . . . . .
H3 H 0.159078 0.461348 -0.078333 0.101 Uiso 1 1 calc R U . . .
C18 C 0.58151(17) 1.1087(2) 0.3951(3) 0.0825(8) Uani 1 1 d . . . . .
H18 H 0.629283 1.128818 0.468241 0.099 Uiso 1 1 calc R U . . .
C23 C 0.3927(2) 1.17382(19) 0.7943(3) 0.0868(8) Uani 1 1 d . . . . .
H23 H 0.370165 1.189651 0.879420 0.104 Uiso 1 1 calc R U . . .
C7 C 0.1084(2) 0.5514(2) 0.2028(3) 0.0893(8) Uani 1 1 d . . . . .
H7 H 0.085430 0.539891 0.289320 0.107 Uiso 1 1 calc R U . . .
C22 C 0.4873(2) 1.1816(2) 0.7901(3) 0.0911(9) Uani 1 1 d . . . . .
H22 H 0.529109 1.202338 0.870318 0.109 Uiso 1 1 calc R U . . .
C15 C 0.2440(2) 1.15006(19) 0.1265(4) 0.0921(8) Uani 1 1 d . . . . .
H15A H 0.265378 1.163247 0.227463 0.138 Uiso 1 1 calc R U . . .
H15B H 0.186733 1.182114 0.091618 0.138 Uiso 1 1 calc R U . . .
H15C H 0.293311 1.164962 0.070642 0.138 Uiso 1 1 calc R U . . .
C1 C 0.0890(3) 0.3995(3) 0.1446(5) 0.1210(14) Uani 1 1 d . . . . .
H1BC H 0.092168 0.396118 0.249635 0.145 Uiso 0.614(9) 1 calc R U P A 1
H1BD H 0.022050 0.392195 0.101949 0.145 Uiso 0.614(9) 1 calc R U P A 1
H1AA H 0.028194 0.401894 0.180838 0.145 Uiso 0.372(9) 1 calc R U P A -1
H1AB H 0.078934 0.366397 0.055064 0.145 Uiso 0.372(9) 1 calc R U P A -1
O1 O 0.1326(2) 0.3382(2) 0.1079(6) 0.098(2) Uani 0.614(9) 1 d . . P A 1
H1A H 0.112263 0.294041 0.140673 0.147 Uiso 0.614(9) 1 calc R U P A 1
O2 O 0.1509(4) 0.3595(4) 0.2398(8) 0.091(3) Uani 0.372(9) 1 d . . P A -1
H2A H 0.203979 0.360386 0.213403 0.136 Uiso 0.372(9) 1 calc R U P A -1
H1 H 0.106(2) 0.7886(18) 0.097(3) 0.080(9) Uiso 1 1 d . . . . .
C1A C -0.0401(2) 0.7602(3) 0.1251(5) 0.1106(18) Uani 0.915(10) 1 d D . P . .
H1AC H -0.069146 0.813489 0.090366 0.166 Uiso 0.915(10) 1 calc R U P . .
H1AD H -0.066114 0.714690 0.061127 0.166 Uiso 0.915(10) 1 calc R U P . .
H1AE H 0.028168 0.763407 0.127105 0.166 Uiso 0.915(10) 1 calc R U P . .
O1A O -0.059(9) 0.744(7) 0.265(6) 0.40(9) Uiso 0.10(2) 1 d D . P . .
H1AF H -0.027955 0.702324 0.299247 0.599 Uiso 0.10(2) 1 calc R U P . .


_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
N4 C19 1.348(3) . ?
N4 C16 1.334(3) . ?
O3 C8 1.222(3) . ?
N2 H2 0.8800 . ?
N2 C16 1.357(3) . ?
N2 C11 1.423(3) . ?
N1 C9 1.410(3) . ?
N1 C8 1.361(3) . ?
N1 H1 0.80(3) . ?
N3 C16 1.347(3) . ?
N3 C17 1.330(3) . ?
N5 C24 1.336(3) . ?
N5 C23 1.328(4) . ?
C19 C20 1.479(3) . ?
C19 C18 1.381(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C10 C9 1.383(3) . ?
C20 C24 1.381(3) . ?
C20 C21 1.382(3) . ?
C11 C12 1.390(3) . ?
C5 C8 1.490(4) . ?
C5 C4 1.387(4) . ?
C5 C6 1.386(4) . ?
C9 C14 1.386(3) . ?
C12 C13 1.390(4) . ?
C12 C15 1.502(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.366(4) . ?
C14 H14 0.9500 . ?
C24 H24 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.387(4) . ?
C2 C3 1.381(5) . ?
C2 C7 1.362(5) . ?
C2 C1 1.504(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.371(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.378(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.360(4) . ?
C3 H3 0.9500 . ?
C18 H18 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.373(4) . ?
C7 H7 0.9500 . ?
C22 H22 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 O1 1.241(5) . ?
C1 O2 1.325(7) . ?
O1 H1A 0.8400 . ?
O1 O2 1.281(7) . ?
O2 H2A 0.8400 . ?
C1A H1AC 0.9800 . ?
C1A H1AD 0.9800 . ?
C1A H1AE 0.9800 . ?
C1A O1A 1.42(2) . ?
O1A H1AF 0.8400 . ?

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
C16 N4 C19 116.84(19) . . ?
C16 N2 H2 117.2 . . ?
C16 N2 C11 125.63(19) . . ?
C11 N2 H2 117.2 . . ?
C9 N1 H1 116(2) . . ?
C8 N1 C9 127.8(2) . . ?
C8 N1 H1 116(2) . . ?
C17 N3 C16 115.1(2) . . ?
C23 N5 C24 117.1(2) . . ?
N4 C19 C20 116.89(19) . . ?
N4 C19 C18 120.6(2) . . ?
C18 C19 C20 122.5(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(2) . . ?
N4 C16 N2 119.52(19) . . ?
N4 C16 N3 126.2(2) . . ?
N3 C16 N2 114.3(2) . . ?
C24 C20 C19 120.5(2) . . ?
C24 C20 C21 116.9(2) . . ?
C21 C20 C19 122.7(2) . . ?
C10 C11 N2 116.6(2) . . ?
C10 C11 C12 121.3(2) . . ?
C12 C11 N2 121.9(2) . . ?
C4 C5 C8 118.4(2) . . ?
C6 C5 C8 122.9(2) . . ?
C6 C5 C4 118.4(3) . . ?
C10 C9 N1 122.6(2) . . ?
C10 C9 C14 118.5(2) . . ?
C14 C9 N1 118.8(2) . . ?
C11 C12 C13 116.7(2) . . ?
C11 C12 C15 123.1(2) . . ?
C13 C12 C15 120.2(2) . . ?
O3 C8 N1 122.8(2) . . ?
O3 C8 C5 122.0(2) . . ?
N1 C8 C5 115.1(2) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 C12 122.5(2) . . ?
C14 C13 H13 118.8 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
N5 C24 C20 124.2(2) . . ?
N5 C24 H24 117.9 . . ?
C20 C24 H24 117.9 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C3 C2 C1 121.6(3) . . ?
C7 C2 C3 118.0(3) . . ?
C7 C2 C1 120.4(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(3) . . ?
C22 C21 H21 120.0 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
N3 C17 H17 118.3 . . ?
N3 C17 C18 123.5(2) . . ?
C18 C17 H17 118.3 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C19 C18 H18 121.1 . . ?
C17 C18 C19 117.8(2) . . ?
C17 C18 H18 121.1 . . ?
N5 C23 H23 118.3 . . ?
N5 C23 C22 123.4(3) . . ?
C22 C23 H23 118.3 . . ?
C2 C7 C6 121.5(3) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C21 C22 C23 118.5(3) . . ?
C21 C22 H22 120.8 . . ?
C23 C22 H22 120.8 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C1 H1BC 107.2 . . ?
C2 C1 H1BD 107.2 . . ?
C2 C1 H1AA 108.5 . . ?
C2 C1 H1AB 108.5 . . ?
H1BC C1 H1BD 106.8 . . ?
H1BC C1 H1AA 63.6 . . ?
H1BC C1 H1AB 144.1 . . ?
H1BD C1 H1AA 44.8 . . ?
H1BD C1 H1AB 65.6 . . ?
H1AA C1 H1AB 107.5 . . ?
O1 C1 C2 120.6(4) . . ?
O1 C1 H1BC 107.2 . . ?
O1 C1 H1BD 107.2 . . ?
O1 C1 H1AA 130.0 . . ?
O1 C1 H1AB 49.6 . . ?
O1 C1 O2 59.8(4) . . ?
O2 C1 C2 114.9(4) . . ?
O2 C1 H1BC 51.1 . . ?
O2 C1 H1BD 136.6 . . ?
O2 C1 H1AA 108.5 . . ?
O2 C1 H1AB 108.5 . . ?
C1 O1 H1A 109.5 . . ?
C1 O1 O2 63.3(4) . . ?
O2 O1 H1A 83.8 . . ?
C1 O2 H2A 109.5 . . ?
O1 O2 C1 56.8(4) . . ?
O1 O2 H2A 76.6 . . ?
H1AC C1A H1AD 109.5 . . ?
H1AC C1A H1AE 109.5 . . ?
H1AD C1A H1AE 109.5 . . ?
O1A C1A H1AC 109.5 . . ?
O1A C1A H1AD 109.5 . . ?
O1A C1A H1AE 109.5 . . ?
C1A O1A H1AF 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
N4 C19 C20 C24 -1.5(3) . . . . ?
N4 C19 C20 C21 -179.9(2) . . . . ?
N4 C19 C18 C17 0.9(4) . . . . ?
N2 C11 C12 C13 177.4(2) . . . . ?
N2 C11 C12 C15 -1.4(4) . . . . ?
N1 C9 C14 C13 176.1(2) . . . . ?
N3 C17 C18 C19 0.1(5) . . . . ?
N5 C23 C22 C21 -0.1(5) . . . . ?
C19 N4 C16 N2 -179.9(2) . . . . ?
C19 N4 C16 N3 0.3(4) . . . . ?
C19 C20 C24 N5 -178.6(3) . . . . ?
C19 C20 C21 C22 179.7(3) . . . . ?
C10 C11 C12 C13 1.5(4) . . . . ?
C10 C11 C12 C15 -177.3(2) . . . . ?
C10 C9 C14 C13 -0.2(4) . . . . ?
C16 N4 C19 C20 177.9(2) . . . . ?
C16 N4 C19 C18 -1.1(4) . . . . ?
C16 N2 C11 C10 -114.6(3) . . . . ?
C16 N2 C11 C12 69.3(3) . . . . ?
C16 N3 C17 C18 -0.8(5) . . . . ?
C20 C19 C18 C17 -178.1(3) . . . . ?
C20 C21 C22 C23 -1.2(5) . . . . ?
C11 N2 C16 N4 -8.8(4) . . . . ?
C11 N2 C16 N3 171.0(2) . . . . ?
C11 C10 C9 N1 -174.9(2) . . . . ?
C11 C10 C9 C14 1.2(3) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C5 C4 C3 C2 -1.5(4) . . . . ?
C5 C6 C7 C2 -0.7(4) . . . . ?
C9 N1 C8 O3 -12.0(4) . . . . ?
C9 N1 C8 C5 167.3(2) . . . . ?
C9 C10 C11 N2 -178.1(2) . . . . ?
C9 C10 C11 C12 -2.0(4) . . . . ?
C12 C13 C14 C9 -0.2(4) . . . . ?
C8 N1 C9 C10 -19.5(4) . . . . ?
C8 N1 C9 C14 164.3(2) . . . . ?
C8 C5 C4 C3 177.7(2) . . . . ?
C8 C5 C6 C7 -176.4(2) . . . . ?
C24 N5 C23 C22 1.2(5) . . . . ?
C24 C20 C21 C22 1.3(4) . . . . ?
C4 C5 C8 O3 -28.9(3) . . . . ?
C4 C5 C8 N1 151.7(2) . . . . ?
C4 C5 C6 C7 -1.2(4) . . . . ?
C2 C1 O1 O2 102.8(5) . . . . ?
C2 C1 O2 O1 -112.2(5) . . . . ?
C21 C20 C24 N5 -0.2(4) . . . . ?
C6 C5 C8 O3 146.3(3) . . . . ?
C6 C5 C8 N1 -33.0(3) . . . . ?
C6 C5 C4 C3 2.2(4) . . . . ?
C17 N3 C16 N4 0.6(4) . . . . ?
C17 N3 C16 N2 -179.2(3) . . . . ?
C3 C2 C7 C6 1.4(4) . . . . ?
C3 C2 C1 O1 33.4(6) . . . . ?
C3 C2 C1 O2 101.7(5) . . . . ?
C18 C19 C20 C24 177.4(3) . . . . ?
C18 C19 C20 C21 -0.9(4) . . . . ?
C23 N5 C24 C20 -1.1(4) . . . . ?
C7 C2 C3 C4 -0.4(4) . . . . ?
C7 C2 C1 O1 -145.7(5) . . . . ?
C7 C2 C1 O2 -77.4(6) . . . . ?
C15 C12 C13 C14 178.4(3) . . . . ?
C1 C2 C3 C4 -179.5(3) . . . . ?
C1 C2 C7 C6 -179.4(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 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.728
