# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mjj2001
_database_code_depnum_ccdc_archive 'CCDC 2102632'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-08-11 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_audit_creation_date             2020-10-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H8 N2 O'
_chemical_formula_sum            'C6 H8 N2 O'
_chemical_formula_weight         124.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H8 N2 O'
_chemical_oxdiff_usercomment     'Michael James WOW-01-001-4'
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'
O O 0.0106 0.0060 '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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   18.1149(5)
_cell_length_b                   7.9429(2)
_cell_length_c                   18.0218(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2593.05(12)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3508
_cell_measurement_temperature    111(3)
_cell_measurement_theta_max      31.8620
_cell_measurement_theta_min      4.0920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.786
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1056
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0082
0 0 1 0.0169
-1 0 0 0.0397
1 0 0 0.0630
2 1 0 0.1582
-1 -1 0 0.1693
-1 1 0 0.1925
1 -1 0 0.1851

_exptl_crystal_recrystallization_method 
'Crystallisationfrom dichloromethane and hexane'
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.025
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
0.0001 0.0000 -0.9999 -0.0353 -0.0172 0.0031
-0.0001 -0.0000 0.9999 0.0353 0.0172 -0.0031
-1.0000 0.0000 -0.0000 0.0149 -0.0263 0.0249
1.0000 -0.0000 0.0000 -0.0149 0.0263 -0.0249
2.0000 0.9999 -0.0000 -0.0500 0.1061 0.0189
-1.0000 -0.9999 0.0000 0.0351 -0.0798 -0.0437
-1.0001 1.0000 -0.0001 -0.0052 0.0273 0.0935
1.0001 -1.0000 0.0001 0.0052 -0.0273 -0.0935

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15188
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.078
_diffrn_reflns_theta_min         3.189
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      111(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_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    -47.00  81.00   1.00  100.00    --   25.64   0.00-180.00  128
  2  ω      8.00  77.00   1.00  100.00    --   25.64  57.00  30.00   69
  3  ω    -88.00 -59.00   1.00  100.00    --  -25.95 178.00-180.00   29
  4  ω   -102.00 -59.00   1.00  100.00    --  -25.95 178.00 -30.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0149270000
_diffrn_orient_matrix_UB_12      -0.0201425000
_diffrn_orient_matrix_UB_13      0.0352803000
_diffrn_orient_matrix_UB_21      0.0262712000
_diffrn_orient_matrix_UB_22      0.0535371000
_diffrn_orient_matrix_UB_23      0.0172193000
_diffrn_orient_matrix_UB_31      -0.0248567000
_diffrn_orient_matrix_UB_32      0.0686043000
_diffrn_orient_matrix_UB_33      -0.0030637000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2957
_reflns_number_total             3802
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3802
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.063
_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+1.2103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1261
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.47736(7) -0.05769(17) 0.63445(7) 0.0194(3) Uani 1 1 d . . . . .
H1 H 0.5152(9) 0.024(2) 0.6203(10) 0.025(4) Uiso 1 1 d . . . . .
C2 C 0.39997(7) -0.01373(16) 0.62955(7) 0.0185(3) Uani 1 1 d . . . . .
C3 C 0.33893(8) -0.08426(19) 0.66364(8) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.3406(9) -0.179(2) 0.6966(10) 0.026(4) Uiso 1 1 d . . . . .
C4 C 0.27670(8) 0.00989(19) 0.64220(9) 0.0261(3) Uani 1 1 d . . . . .
H4 H 0.2271(10) -0.007(2) 0.6583(10) 0.034(5) Uiso 1 1 d . . . . .
C5 C 0.30107(8) 0.13440(19) 0.59569(9) 0.0256(3) Uani 1 1 d . . . . .
H5 H 0.2737(10) 0.219(2) 0.5702(10) 0.030(5) Uiso 1 1 d . . . . .
C6 C 0.41983(10) 0.2252(2) 0.53862(10) 0.0312(3) Uani 1 1 d . . . . .
H6A H 0.3912(16) 0.311(4) 0.5143(16) 0.083(9) Uiso 1 1 d . . . . .
H6B H 0.4603(15) 0.281(3) 0.5662(15) 0.072(8) Uiso 1 1 d . . . . .
H6C H 0.4423(16) 0.159(4) 0.5025(16) 0.081(9) Uiso 1 1 d . . . . .
N1 N 0.49657(6) -0.20234(15) 0.65899(6) 0.0194(2) Uani 1 1 d . . . . .
N2 N 0.37573(6) 0.12102(14) 0.58792(7) 0.0210(2) Uani 1 1 d . . . . .
O1 O 0.57366(5) -0.21664(13) 0.66348(6) 0.0239(2) Uani 1 1 d . . . . .
H1A H 0.5808(12) -0.320(3) 0.6867(13) 0.048(6) Uiso 1 1 d . . . . .
C7 C 0.61800(7) 0.34396(17) 0.72137(8) 0.0185(3) Uani 1 1 d . . . . .
H7 H 0.6316(10) 0.255(2) 0.7567(10) 0.029(4) Uiso 1 1 d . . . . .
C8 C 0.62664(7) 0.31273(17) 0.64255(8) 0.0185(3) Uani 1 1 d . . . . .
C9 C 0.59657(8) 0.39696(19) 0.58239(8) 0.0241(3) Uani 1 1 d . . . . .
H9 H 0.5631(11) 0.492(2) 0.5853(11) 0.035(5) Uiso 1 1 d . . . . .
C10 C 0.62202(10) 0.3171(2) 0.51779(9) 0.0298(3) Uani 1 1 d . . . . .
H10 H 0.6084(11) 0.348(3) 0.4692(12) 0.044(6) Uiso 1 1 d . . . . .
C11 C 0.66663(9) 0.18684(19) 0.53948(8) 0.0265(3) Uani 1 1 d . . . . .
H11 H 0.6955(11) 0.105(2) 0.5117(11) 0.038(5) Uiso 1 1 d . . . . .
C12 C 0.71524(9) 0.0682(2) 0.65782(10) 0.0307(3) Uani 1 1 d . . . . .
H12A H 0.6844(14) -0.005(3) 0.6858(14) 0.058(7) Uiso 1 1 d . . . . .
H12B H 0.7477(14) 0.127(3) 0.6889(13) 0.062(7) Uiso 1 1 d . . . . .
H12C H 0.7432(15) -0.001(3) 0.6229(14) 0.069(7) Uiso 1 1 d . . . . .
N3 N 0.59220(6) 0.48655(14) 0.74220(6) 0.0181(2) Uani 1 1 d . . . . .
N4 N 0.66970(6) 0.18392(14) 0.61508(7) 0.0211(2) Uani 1 1 d . . . . .
O2 O 0.58338(6) 0.49659(13) 0.81914(5) 0.0224(2) Uani 1 1 d . . . . .
H2 H 0.5592(12) 0.593(3) 0.8243(11) 0.041(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
C1 H1 0.979(17) . ?
C1 C2 1.4475(18) . ?
C1 N1 1.2793(18) . ?
C2 C3 1.3834(19) . ?
C2 N2 1.3788(17) . ?
C3 H3 0.957(19) . ?
C3 C4 1.407(2) . ?
C4 H4 0.954(19) . ?
C4 C5 1.369(2) . ?
C5 H5 0.954(19) . ?
C5 N2 1.3638(19) . ?
C6 H6A 0.96(3) . ?
C6 H6B 0.99(3) . ?
C6 H6C 0.93(3) . ?
C6 N2 1.453(2) . ?
N1 O1 1.4034(14) . ?
O1 H1A 0.93(2) . ?
C7 H7 0.982(18) . ?
C7 C8 1.4504(19) . ?
C7 N3 1.2814(17) . ?
C8 C9 1.3857(19) . ?
C8 N4 1.3785(17) . ?
C9 H9 0.97(2) . ?
C9 C10 1.403(2) . ?
C10 H10 0.94(2) . ?
C10 C11 1.370(2) . ?
C11 H11 0.97(2) . ?
C11 N4 1.3638(19) . ?
C12 H12A 0.95(2) . ?
C12 H12B 0.94(3) . ?
C12 H12C 0.98(3) . ?
C12 N4 1.456(2) . ?
N3 O2 1.3981(14) . ?
O2 H2 0.89(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.2(10) . . ?
N1 C1 H1 119.7(10) . . ?
N1 C1 C2 120.08(12) . . ?
C3 C2 C1 130.49(13) . . ?
N2 C2 C1 121.93(12) . . ?
N2 C2 C3 107.54(12) . . ?
C2 C3 H3 124.6(10) . . ?
C2 C3 C4 107.65(13) . . ?
C4 C3 H3 127.8(10) . . ?
C3 C4 H4 126.6(11) . . ?
C5 C4 C3 107.08(13) . . ?
C5 C4 H4 126.3(11) . . ?
C4 C5 H5 129.6(11) . . ?
N2 C5 C4 109.04(13) . . ?
N2 C5 H5 121.4(11) . . ?
H6A C6 H6B 108(2) . . ?
H6A C6 H6C 108(2) . . ?
H6B C6 H6C 106(2) . . ?
N2 C6 H6A 112.7(17) . . ?
N2 C6 H6B 110.7(15) . . ?
N2 C6 H6C 110.2(17) . . ?
C1 N1 O1 111.30(11) . . ?
C2 N2 C6 126.84(12) . . ?
C5 N2 C2 108.69(12) . . ?
C5 N2 C6 124.29(13) . . ?
N1 O1 H1A 103.6(13) . . ?
C8 C7 H7 119.0(11) . . ?
N3 C7 H7 122.5(11) . . ?
N3 C7 C8 118.52(12) . . ?
C9 C8 C7 129.89(12) . . ?
N4 C8 C7 122.67(12) . . ?
N4 C8 C9 107.44(12) . . ?
C8 C9 H9 125.4(12) . . ?
C8 C9 C10 107.57(13) . . ?
C10 C9 H9 127.0(12) . . ?
C9 C10 H10 124.6(13) . . ?
C11 C10 C9 107.35(14) . . ?
C11 C10 H10 128.0(13) . . ?
C10 C11 H11 132.4(12) . . ?
N4 C11 C10 108.78(13) . . ?
N4 C11 H11 118.8(12) . . ?
H12A C12 H12B 111(2) . . ?
H12A C12 H12C 108(2) . . ?
H12B C12 H12C 110(2) . . ?
N4 C12 H12A 109.5(15) . . ?
N4 C12 H12B 110.8(15) . . ?
N4 C12 H12C 108.0(15) . . ?
C7 N3 O2 112.50(11) . . ?
C8 N4 C12 126.83(13) . . ?
C11 N4 C8 108.85(12) . . ?
C11 N4 C12 124.22(13) . . ?
N3 O2 H2 102.1(13) . . ?

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
O1 H1A N3 0.93(2) 1.84(2) 2.7718(15) 174(2) 1_545 yes
O2 H2 N1 0.89(2) 1.93(2) 2.8235(16) 176(2) 3_666 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
C1 C2 C3 C4 177.80(14) . . . . ?
C1 C2 N2 C5 -178.17(12) . . . . ?
C1 C2 N2 C6 6.6(2) . . . . ?
C2 C1 N1 O1 -176.51(11) . . . . ?
C2 C3 C4 C5 0.17(17) . . . . ?
C3 C2 N2 C5 -0.10(15) . . . . ?
C3 C2 N2 C6 -175.37(15) . . . . ?
C3 C4 C5 N2 -0.24(17) . . . . ?
C4 C5 N2 C2 0.22(16) . . . . ?
C4 C5 N2 C6 175.63(14) . . . . ?
N1 C1 C2 C3 18.2(2) . . . . ?
N1 C1 C2 N2 -164.23(13) . . . . ?
N2 C2 C3 C4 -0.04(16) . . . . ?
C7 C8 C9 C10 -179.98(14) . . . . ?
C7 C8 N4 C11 179.87(12) . . . . ?
C7 C8 N4 C12 -3.6(2) . . . . ?
C8 C7 N3 O2 177.05(11) . . . . ?
C8 C9 C10 C11 0.07(18) . . . . ?
C9 C8 N4 C11 -0.15(15) . . . . ?
C9 C8 N4 C12 176.34(14) . . . . ?
C9 C10 C11 N4 -0.16(18) . . . . ?
C10 C11 N4 C8 0.19(17) . . . . ?
C10 C11 N4 C12 -176.41(14) . . . . ?
N3 C7 C8 C9 -16.3(2) . . . . ?
N3 C7 C8 N4 163.67(12) . . . . ?
N4 C8 C9 C10 0.04(16) . . . . ?

_olex2_date_sample_data_collection 2020-10-12
_olex2_date_sample_submission    2020-10-12
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id WOW-01-001-4
_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 1.172
_oxdiff_exptl_absorpt_empirical_full_min 0.912
####################################################################### 
# 
# 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_mjj21001
_database_code_depnum_ccdc_archive 'CCDC 2102633'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-08-11 deposited with the CCDC.	2021-10-20 downloaded from the CCDC.
;
_audit_creation_date             2021-06-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H31 N3 O'
_chemical_formula_sum            'C23 H31 N3 O'
_chemical_formula_weight         365.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H31 N3 O1'
_chemical_oxdiff_usercomment     'Andrew Greener AJG-02-010-3'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5000(3)
_cell_length_b                   11.7569(3)
_cell_length_c                   18.0932(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.562(3)
_cell_angle_gamma                90
_cell_volume                     1979.83(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3909
_cell_measurement_temperature    109.9(6)
_cell_measurement_theta_max      70.8510
_cell_measurement_theta_min      4.5020
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -1 0.0541
0 -1 1 0.0410
0 1 1 0.0521
0 -1 -1 0.0425
1 -6 -7 0.0332
-2 1 -2 0.0918
2 -2 1 0.0975
2 -2 -1 0.1014
-1 1 1 0.1329
2 0 1 0.1066
-2 0 -1 0.1197
0 1 2 0.0570
-1 -5 9 0.0457
1 1 0 0.1051

_exptl_crystal_recrystallization_method 'Crystallisation from DMSO'
_exptl_crystal_size_max          0.276
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.095
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 0.9975 -1.0064 -0.0020 0.1573 0.0032
-0.0003 -0.9975 1.0064 0.0020 -0.1573 -0.0032
0.0015 1.0038 0.9945 0.0465 0.0591 0.1383
-0.0015 -1.0038 -0.9945 -0.0465 -0.0591 -0.1383
0.9909 -6.0254 -6.9676 -0.1407 -0.3213 -0.9242
-2.0007 0.9933 -2.0071 -0.3515 0.2380 -0.0104
1.9993 -1.9971 1.0125 0.3050 -0.2971 -0.1279
1.9981 -2.0034 -0.9884 0.2564 -0.1989 -0.2630
-0.9987 1.0033 0.9944 -0.1161 0.0749 0.1653
2.0010 0.0042 1.0007 0.3494 -0.0807 0.0136
-2.0010 -0.0042 -1.0007 -0.3494 0.0807 -0.0136
0.0021 1.0070 1.9950 0.0708 0.0100 0.2058
-0.9992 -4.9751 9.0335 -0.0552 -0.9668 0.2811
1.0011 1.0011 -0.0058 0.1848 0.0924 0.0438

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.513
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  30.00   1.00    1.00    --    0.00 -77.00 -60.00   49
  2  ω    -20.00   6.00   1.00    1.00    --    0.00 -77.00 150.00   26
  3  ω    -19.00  13.00   1.00    1.00    --    0.00 -77.00  60.00   32
  4  ω     38.00  65.00   1.00    3.00    --   54.00  57.00 -90.00   27
  5  ω     37.00 123.00   1.00    3.00    --   54.00  57.00 -60.00   86
  6  ω     43.00 118.00   1.00    3.00    --   54.00  57.00  60.00   75
  7  ω    -13.00  65.00   1.00    3.00    --   54.00 -57.00 150.00   78
  8  ω     97.00 141.00   1.00    3.00    --  108.00 -25.00 120.00   44
  9  ω     38.00  78.00   1.00    3.00    --  108.00 -25.00 120.00   40
 10  ω     38.00  89.00   1.00    3.00    --  108.00 -50.00-180.00   51
 11  ω     99.00 126.00   1.00    3.00    --  108.00 -50.00 -90.00   27
 12  ω     61.00 106.00   1.00    3.00    --  108.00 -91.00-120.00   45
 13  ω    114.00 149.00   1.00    3.00    --  108.00 111.00-150.00   35
 14  ω     42.00  84.00   1.00    3.00    --  108.00 -50.00 -90.00   42
 15  ω    115.00 177.00   1.00    3.00    --  108.00 111.00-180.00   62
 16  ω     42.00  69.00   1.00    3.00    --  108.00 -91.00-180.00   27
 17  ω     99.00 126.00   1.00    3.00    --  108.00 -50.00-180.00   27
 18  ω     36.00 176.00   1.00    3.00    --  108.00   0.00  30.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1625227000
_diffrn_orient_matrix_UB_12      0.0222189000
_diffrn_orient_matrix_UB_13      0.0240974000
_diffrn_orient_matrix_UB_21      -0.0158482000
_diffrn_orient_matrix_UB_22      0.1078357000
_diffrn_orient_matrix_UB_23      -0.0493920000
_diffrn_orient_matrix_UB_31      -0.0270161000
_diffrn_orient_matrix_UB_32      0.0711158000
_diffrn_orient_matrix_UB_33      0.0673008000
_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                3032
_reflns_number_total             3538
_reflns_odcompleteness_completeness 99.92
_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 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00040(12)
_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   1.021
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.021
_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)+(0.0436P)²+0.5760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0928
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.46959(13) 0.49287(10) 0.31920(7) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.42809(14) 0.57896(11) 0.36372(7) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.4812(16) 0.6545(13) 0.3709(8) 0.031(4) Uiso 1 1 d . . . . .
C3 C 0.31330(13) 0.56103(11) 0.39886(7) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.23824(13) 0.45729(11) 0.38812(7) 0.0221(3) Uani 1 1 d . . . . .
C5 C 0.11728(14) 0.43143(12) 0.42836(8) 0.0265(3) Uani 1 1 d . . . . .
H5A H 0.0454(17) 0.3811(14) 0.3954(9) 0.034(4) Uiso 1 1 d . . . . .
H5B H 0.0673(16) 0.5048(13) 0.4368(8) 0.027(4) Uiso 1 1 d . . . . .
C6 C 0.16755(16) 0.37265(13) 0.50494(8) 0.0315(3) Uani 1 1 d . . . . .
H6A H 0.0786(18) 0.3510(14) 0.5247(9) 0.037(4) Uiso 1 1 d . . . . .
H6B H 0.2223(17) 0.4315(14) 0.5414(9) 0.037(4) Uiso 1 1 d . . . . .
C7 C 0.25867(17) 0.26643(13) 0.50298(8) 0.0321(3) Uani 1 1 d . . . . .
H7A H 0.3573(17) 0.2879(13) 0.4926(8) 0.030(4) Uiso 1 1 d . . . . .
H7B H 0.2779(18) 0.2337(15) 0.5548(10) 0.044(5) Uiso 1 1 d . . . . .
C8 C 0.19159(17) 0.17334(13) 0.44735(9) 0.0325(3) Uani 1 1 d . . . . .
H8A H 0.2126(18) 0.0968(15) 0.4719(10) 0.042(5) Uiso 1 1 d . . . . .
H8B H 0.0851(19) 0.1824(15) 0.4363(9) 0.040(5) Uiso 1 1 d . . . . .
C9 C 0.24650(16) 0.16899(12) 0.37351(8) 0.0284(3) Uani 1 1 d . . . . .
H9A H 0.2096(16) 0.0997(13) 0.3457(8) 0.028(4) Uiso 1 1 d . . . . .
H9B H 0.3558(17) 0.1642(13) 0.3855(8) 0.032(4) Uiso 1 1 d . . . . .
C10 C 0.20428(14) 0.26740(12) 0.31800(8) 0.0257(3) Uani 1 1 d . . . . .
H10A H 0.2246(15) 0.2455(12) 0.2679(8) 0.025(4) Uiso 1 1 d . . . . .
H10B H 0.0968(17) 0.2805(14) 0.3102(9) 0.036(4) Uiso 1 1 d . . . . .
C11 C 0.28223(13) 0.37874(11) 0.33941(7) 0.0213(3) Uani 1 1 d . . . . .
C12 C 0.60532(15) 0.42572(11) 0.22600(8) 0.0245(3) Uani 1 1 d . . . . .
H12A H 0.5497(16) 0.4600(13) 0.1768(9) 0.032(4) Uiso 1 1 d . . . . .
H12B H 0.5634(17) 0.3518(14) 0.2337(9) 0.036(4) Uiso 1 1 d . . . . .
C13 C 0.76151(15) 0.41096(11) 0.22096(8) 0.0254(3) Uani 1 1 d . . . . .
H13A H 0.8146(16) 0.3704(14) 0.2680(9) 0.031(4) Uiso 1 1 d . . . . .
H13B H 0.7683(16) 0.3634(13) 0.1767(9) 0.031(4) Uiso 1 1 d . . . . .
C14 C 0.81507(15) 0.59366(12) 0.27568(8) 0.0254(3) Uani 1 1 d . . . . .
H14A H 0.8701(17) 0.5572(14) 0.3246(9) 0.035(4) Uiso 1 1 d . . . . .
H14B H 0.8580(16) 0.6653(14) 0.2686(8) 0.030(4) Uiso 1 1 d . . . . .
C15 C 0.65999(15) 0.60991(11) 0.28223(8) 0.0259(3) Uani 1 1 d . . . . .
H15A H 0.6094(15) 0.6485(12) 0.2365(8) 0.025(4) Uiso 1 1 d . . . . .
H15B H 0.6612(17) 0.6551(13) 0.3289(9) 0.034(4) Uiso 1 1 d . . . . .
C16 C 0.98095(14) 0.50997(12) 0.20723(8) 0.0289(3) Uani 1 1 d . . . . .
H16A H 1.0202(15) 0.5872(12) 0.2046(7) 0.020(3) Uiso 1 1 d . . . . .
H16B H 1.0355(17) 0.4735(14) 0.2562(9) 0.037(4) Uiso 1 1 d . . . . .
C17 C 1.00606(18) 0.44120(14) 0.14072(11) 0.0393(4) Uani 1 1 d . . . . .
H17A H 0.9552(19) 0.4744(16) 0.0906(10) 0.046(5) Uiso 1 1 d . . . . .
H17B H 1.105(2) 0.4434(16) 0.1394(10) 0.050(5) Uiso 1 1 d . . . . .
H17C H 0.980(2) 0.3626(17) 0.1453(10) 0.055(5) Uiso 1 1 d . . . . .
C18 C 0.27241(13) 0.65496(11) 0.44623(7) 0.0213(3) Uani 1 1 d . . . . .
C19 C 0.33236(16) 0.66215(12) 0.52277(8) 0.0302(3) Uani 1 1 d . . . . .
H19 H 0.3970(19) 0.6028(16) 0.5449(10) 0.047(5) Uiso 1 1 d . . . . .
C20 C 0.29959(15) 0.75123(12) 0.56659(8) 0.0299(3) Uani 1 1 d . . . . .
H20 H 0.3442(18) 0.7552(14) 0.6204(10) 0.044(5) Uiso 1 1 d . . . . .
C21 C 0.20526(13) 0.83605(11) 0.53424(7) 0.0228(3) Uani 1 1 d . . . . .
C22 C 0.14469(15) 0.82971(12) 0.45782(8) 0.0276(3) Uani 1 1 d . . . . .
H22 H 0.0800(19) 0.8920(15) 0.4370(9) 0.043(5) Uiso 1 1 d . . . . .
C23 C 0.17869(15) 0.74043(12) 0.41455(7) 0.0267(3) Uani 1 1 d . . . . .
H23 H 0.1382(16) 0.7377(13) 0.3607(9) 0.034(4) Uiso 1 1 d . . . . .
N1 N 0.39501(11) 0.39540(9) 0.30591(6) 0.0214(2) Uani 1 1 d . . . . .
N2 N 0.59294(12) 0.50044(9) 0.28869(6) 0.0222(2) Uani 1 1 d . . . . .
N3 N 0.82796(11) 0.52133(9) 0.21146(6) 0.0218(2) Uani 1 1 d . . . . .
O1 O 0.16798(10) 0.92553(8) 0.57369(5) 0.0292(2) Uani 1 1 d . . . . .
H1 H 0.229(2) 0.9312(17) 0.6240(12) 0.060(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
C1 C2 1.3986(17) . ?
C1 N1 1.3434(16) . ?
C1 N2 1.3948(16) . ?
C2 H2 1.017(16) . ?
C2 C3 1.3842(18) . ?
C3 C4 1.4065(18) . ?
C3 C18 1.4961(17) . ?
C4 C5 1.5093(18) . ?
C4 C11 1.3972(18) . ?
C5 H5A 1.004(16) . ?
C5 H5B 1.011(15) . ?
C5 C6 1.536(2) . ?
C6 H6A 1.013(16) . ?
C6 H6B 1.023(17) . ?
C6 C7 1.524(2) . ?
C7 H7A 1.024(15) . ?
C7 H7B 0.996(18) . ?
C7 C8 1.536(2) . ?
C8 H8A 1.006(18) . ?
C8 H8B 0.997(17) . ?
C8 C9 1.529(2) . ?
C9 H9A 0.984(16) . ?
C9 H9B 1.019(16) . ?
C9 C10 1.532(2) . ?
C10 H10A 0.998(14) . ?
C10 H10B 1.014(16) . ?
C10 C11 1.5156(18) . ?
C11 N1 1.3468(16) . ?
C12 H12A 1.023(16) . ?
C12 H12B 0.977(17) . ?
C12 C13 1.5147(18) . ?
C12 N2 1.4580(16) . ?
C13 H13A 1.017(16) . ?
C13 H13B 0.990(16) . ?
C13 N3 1.4682(16) . ?
C14 H14A 1.026(16) . ?
C14 H14B 0.956(16) . ?
C14 C15 1.5135(19) . ?
C14 N3 1.4648(16) . ?
C15 H15A 0.981(15) . ?
C15 H15B 0.996(16) . ?
C15 N2 1.4512(16) . ?
C16 H16A 0.986(14) . ?
C16 H16B 1.026(17) . ?
C16 C17 1.508(2) . ?
C16 N3 1.4767(16) . ?
C17 H17A 1.017(18) . ?
C17 H17B 0.947(19) . ?
C17 H17C 0.96(2) . ?
C18 C19 1.3904(18) . ?
C18 C23 1.3879(18) . ?
C19 H19 0.962(19) . ?
C19 C20 1.3860(19) . ?
C20 H20 0.982(18) . ?
C20 C21 1.3891(19) . ?
C21 C22 1.3891(18) . ?
C21 O1 1.3575(15) . ?
C22 H22 0.981(18) . ?
C22 C23 1.3859(19) . ?
C23 H23 0.974(16) . ?
O1 H1 0.98(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.41(11) . . ?
N1 C1 N2 116.00(11) . . ?
N2 C1 C2 122.55(11) . . ?
C1 C2 H2 121.1(9) . . ?
C3 C2 C1 119.56(12) . . ?
C3 C2 H2 119.4(8) . . ?
C2 C3 C4 119.53(11) . . ?
C2 C3 C18 118.01(11) . . ?
C4 C3 C18 122.45(11) . . ?
C3 C4 C5 121.46(11) . . ?
C11 C4 C3 116.93(11) . . ?
C11 C4 C5 121.60(12) . . ?
C4 C5 H5A 109.0(9) . . ?
C4 C5 H5B 109.1(8) . . ?
C4 C5 C6 113.36(11) . . ?
H5A C5 H5B 107.9(12) . . ?
C6 C5 H5A 108.8(9) . . ?
C6 C5 H5B 108.5(8) . . ?
C5 C6 H6A 107.5(9) . . ?
C5 C6 H6B 107.7(9) . . ?
H6A C6 H6B 107.2(12) . . ?
C7 C6 C5 115.03(12) . . ?
C7 C6 H6A 108.6(9) . . ?
C7 C6 H6B 110.5(9) . . ?
C6 C7 H7A 110.3(9) . . ?
C6 C7 H7B 107.0(10) . . ?
C6 C7 C8 115.85(13) . . ?
H7A C7 H7B 105.5(13) . . ?
C8 C7 H7A 109.3(9) . . ?
C8 C7 H7B 108.4(10) . . ?
C7 C8 H8A 109.2(10) . . ?
C7 C8 H8B 109.1(10) . . ?
H8A C8 H8B 106.7(13) . . ?
C9 C8 C7 115.27(12) . . ?
C9 C8 H8A 106.5(9) . . ?
C9 C8 H8B 109.8(10) . . ?
C8 C9 H9A 109.0(9) . . ?
C8 C9 H9B 109.1(9) . . ?
C8 C9 C10 117.21(12) . . ?
H9A C9 H9B 107.8(12) . . ?
C10 C9 H9A 105.7(9) . . ?
C10 C9 H9B 107.6(9) . . ?
C9 C10 H10A 109.2(8) . . ?
C9 C10 H10B 109.2(9) . . ?
H10A C10 H10B 106.6(12) . . ?
C11 C10 C9 115.75(11) . . ?
C11 C10 H10A 106.3(8) . . ?
C11 C10 H10B 109.4(9) . . ?
C4 C11 C10 122.65(11) . . ?
N1 C11 C4 123.60(12) . . ?
N1 C11 C10 113.74(11) . . ?
H12A C12 H12B 108.7(12) . . ?
C13 C12 H12A 109.5(8) . . ?
C13 C12 H12B 109.8(9) . . ?
N2 C12 H12A 109.4(9) . . ?
N2 C12 H12B 109.0(9) . . ?
N2 C12 C13 110.40(11) . . ?
C12 C13 H13A 109.3(9) . . ?
C12 C13 H13B 109.7(9) . . ?
H13A C13 H13B 108.1(12) . . ?
N3 C13 C12 110.81(11) . . ?
N3 C13 H13A 111.1(9) . . ?
N3 C13 H13B 107.7(9) . . ?
H14A C14 H14B 109.0(13) . . ?
C15 C14 H14A 108.7(9) . . ?
C15 C14 H14B 110.3(9) . . ?
N3 C14 H14A 109.4(9) . . ?
N3 C14 H14B 107.4(9) . . ?
N3 C14 C15 111.89(11) . . ?
C14 C15 H15A 108.2(8) . . ?
C14 C15 H15B 106.7(9) . . ?
H15A C15 H15B 112.9(12) . . ?
N2 C15 C14 110.13(11) . . ?
N2 C15 H15A 109.2(9) . . ?
N2 C15 H15B 109.6(9) . . ?
H16A C16 H16B 107.2(12) . . ?
C17 C16 H16A 109.5(8) . . ?
C17 C16 H16B 109.3(9) . . ?
N3 C16 H16A 107.7(8) . . ?
N3 C16 H16B 109.0(9) . . ?
N3 C16 C17 113.86(12) . . ?
C16 C17 H17A 112.5(10) . . ?
C16 C17 H17B 108.8(11) . . ?
C16 C17 H17C 111.2(11) . . ?
H17A C17 H17B 105.3(14) . . ?
H17A C17 H17C 111.1(15) . . ?
H17B C17 H17C 107.6(16) . . ?
C19 C18 C3 120.92(11) . . ?
C23 C18 C3 121.10(11) . . ?
C23 C18 C19 117.91(12) . . ?
C18 C19 H19 118.0(11) . . ?
C20 C19 C18 121.43(13) . . ?
C20 C19 H19 120.6(11) . . ?
C19 C20 H20 120.1(10) . . ?
C19 C20 C21 120.09(12) . . ?
C21 C20 H20 119.8(10) . . ?
C22 C21 C20 118.97(12) . . ?
O1 C21 C20 123.30(12) . . ?
O1 C21 C22 117.72(12) . . ?
C21 C22 H22 116.4(10) . . ?
C23 C22 C21 120.40(13) . . ?
C23 C22 H22 123.2(10) . . ?
C18 C23 H23 118.8(9) . . ?
C22 C23 C18 121.19(12) . . ?
C22 C23 H23 120.0(9) . . ?
C1 N1 C11 118.81(11) . . ?
C1 N2 C12 118.34(10) . . ?
C1 N2 C15 120.37(10) . . ?
C15 N2 C12 111.51(10) . . ?
C13 N3 C16 112.14(10) . . ?
C14 N3 C13 108.30(10) . . ?
C14 N3 C16 109.47(10) . . ?
C21 O1 H1 112.0(12) . . ?

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
O1 H1 N3 0.98(2) 1.76(2) 2.7193(14) 165.3(18) 4_576 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
C1 C2 C3 C4 -1.23(18) . . . . ?
C1 C2 C3 C18 179.80(11) . . . . ?
C2 C1 N1 C11 -3.28(18) . . . . ?
C2 C1 N2 C12 -161.79(12) . . . . ?
C2 C1 N2 C15 -18.77(18) . . . . ?
C2 C3 C4 C5 176.84(12) . . . . ?
C2 C3 C4 C11 -2.24(18) . . . . ?
C2 C3 C18 C19 -90.28(16) . . . . ?
C2 C3 C18 C23 86.71(16) . . . . ?
C3 C4 C5 C6 -90.09(15) . . . . ?
C3 C4 C11 C10 -175.31(11) . . . . ?
C3 C4 C11 N1 3.22(19) . . . . ?
C3 C18 C19 C20 177.44(13) . . . . ?
C3 C18 C23 C22 -177.66(13) . . . . ?
C4 C3 C18 C19 90.77(16) . . . . ?
C4 C3 C18 C23 -92.23(16) . . . . ?
C4 C5 C6 C7 -52.64(17) . . . . ?
C4 C11 N1 C1 -0.47(18) . . . . ?
C5 C4 C11 C10 5.61(19) . . . . ?
C5 C4 C11 N1 -175.86(12) . . . . ?
C5 C6 C7 C8 -54.97(17) . . . . ?
C6 C7 C8 C9 101.07(15) . . . . ?
C7 C8 C9 C10 -69.33(17) . . . . ?
C8 C9 C10 C11 74.35(16) . . . . ?
C9 C10 C11 C4 -84.19(16) . . . . ?
C9 C10 C11 N1 97.15(14) . . . . ?
C10 C11 N1 C1 178.17(11) . . . . ?
C11 C4 C5 C6 88.95(15) . . . . ?
C12 C13 N3 C14 58.45(14) . . . . ?
C12 C13 N3 C16 179.34(11) . . . . ?
C13 C12 N2 C1 -157.47(11) . . . . ?
C13 C12 N2 C15 56.43(14) . . . . ?
C14 C15 N2 C1 159.17(11) . . . . ?
C14 C15 N2 C12 -55.51(14) . . . . ?
C15 C14 N3 C13 -58.31(14) . . . . ?
C15 C14 N3 C16 179.15(11) . . . . ?
C17 C16 N3 C13 62.40(16) . . . . ?
C17 C16 N3 C14 -177.38(12) . . . . ?
C18 C3 C4 C5 -4.23(18) . . . . ?
C18 C3 C4 C11 176.69(11) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?
C19 C18 C23 C22 -0.6(2) . . . . ?
C19 C20 C21 C22 0.2(2) . . . . ?
C19 C20 C21 O1 179.82(13) . . . . ?
C20 C21 C22 C23 -0.4(2) . . . . ?
C21 C22 C23 C18 0.6(2) . . . . ?
C23 C18 C19 C20 0.3(2) . . . . ?
N1 C1 C2 C3 4.14(18) . . . . ?
N1 C1 N2 C12 20.81(16) . . . . ?
N1 C1 N2 C15 163.83(11) . . . . ?
N2 C1 C2 C3 -173.12(11) . . . . ?
N2 C1 N1 C11 174.15(10) . . . . ?
N2 C12 C13 N3 -58.20(14) . . . . ?
N3 C14 C15 N2 57.24(15) . . . . ?
O1 C21 C22 C23 179.93(13) . . . . ?

_olex2_date_sample_data_collection 2021-06-14
_olex2_date_sample_submission    2021-06-11
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id AJG-020-010-3
_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 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.783


### End
