# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
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data_q24105sp_0m
_database_code_depnum_ccdc_archive 'CCDC 2540706'
_audit_update_record             
;
2026-03-24 deposited with the CCDC.	2026-04-23 downloaded from the CCDC.
;
_audit_creation_date             2024-06-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Br Mn N2 O4, C H4 O'
_chemical_formula_sum            'C23 H28 Br Mn N2 O5'
_chemical_formula_weight         547.32
_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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn -0.5299 2.8052 '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                   9.3579(2)
_cell_length_b                   17.8308(4)
_cell_length_c                   14.6057(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.3510(10)
_cell_angle_gamma                90
_cell_volume                     2436.41(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9118
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      72.391
_cell_measurement_theta_min      3.913
_shelx_estimated_absorpt_T_max   0.661
_shelx_estimated_absorpt_T_min   0.383
_exptl_absorpt_coefficient_mu    6.625
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1547 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.5340.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.068
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28966
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.384
_diffrn_reflns_theta_min         3.913
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Quest Photon III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4067
_reflns_number_total             4780
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.762
_refine_diff_density_min         -1.184
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.038
_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)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5)
;
_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
Br1 Br 0.79632(3) 0.35788(2) 0.59162(2) 0.02524(10) Uani 1 1 d . . . . .
Mn1 Mn 0.75862(4) 0.30475(2) 0.43168(3) 0.01504(10) Uani 1 1 d . . . . .
O1 O 0.59629(17) 0.45446(9) 0.35743(12) 0.0219(4) Uani 1 1 d . . . . .
H1 H 0.554104 0.492584 0.336521 0.033 Uiso 1 1 calc R U . . .
O2 O 0.9273(2) 0.43828(12) 0.38020(18) 0.0428(6) Uani 1 1 d . . . . .
O3 O 0.7567(2) 0.27109(12) 0.23512(13) 0.0330(4) Uani 1 1 d . . . . .
O4 O 1.03877(19) 0.22957(11) 0.45175(14) 0.0313(4) Uani 1 1 d . . . . .
N1 N 0.55388(19) 0.34885(11) 0.43751(13) 0.0159(4) Uani 1 1 d . . . . .
N2 N 0.6428(2) 0.21523(11) 0.47921(13) 0.0156(4) Uani 1 1 d . . . . .
C1 C 0.5079(2) 0.41616(13) 0.41080(15) 0.0166(4) Uani 1 1 d . . . . .
C2 C 0.3755(2) 0.44527(14) 0.43703(17) 0.0211(5) Uani 1 1 d . . . . .
H2 H 0.346928 0.494113 0.418172 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2876(3) 0.40249(14) 0.49026(17) 0.0229(5) Uani 1 1 d . . . . .
H3 H 0.198786 0.421766 0.509941 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3312(3) 0.33045(14) 0.51471(17) 0.0216(5) Uani 1 1 d . . . . .
H4 H 0.271406 0.299069 0.549844 0.026 Uiso 1 1 calc R U . . .
C5 C 0.4628(2) 0.30547(13) 0.48697(16) 0.0177(5) Uani 1 1 d . . . . .
C6 C 0.5144(2) 0.22868(13) 0.50435(15) 0.0178(5) Uani 1 1 d . . . . .
C7 C 0.4152(3) 0.17268(15) 0.54497(19) 0.0269(6) Uani 1 1 d . . . . .
H7A H 0.459835 0.122968 0.544726 0.040 Uiso 1 1 calc R U . . .
H7B H 0.325749 0.171245 0.508708 0.040 Uiso 1 1 calc R U . . .
H7C H 0.394882 0.187129 0.608081 0.040 Uiso 1 1 calc R U . . .
C8 C 0.6988(2) 0.13933(12) 0.48537(16) 0.0160(4) Uani 1 1 d . . . . .
C9 C 0.7702(3) 0.11618(14) 0.56641(18) 0.0235(5) Uani 1 1 d . . . . .
C10 C 0.8288(3) 0.04399(15) 0.5671(2) 0.0289(6) Uani 1 1 d . . . . .
H10 H 0.878826 0.026855 0.620411 0.035 Uiso 1 1 calc R U . . .
C11 C 0.8158(3) -0.00249(15) 0.4930(2) 0.0304(6) Uani 1 1 d . . . . .
H11 H 0.857844 -0.050977 0.495120 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7419(3) 0.02065(15) 0.41486(19) 0.0254(5) Uani 1 1 d . . . . .
H12 H 0.732724 -0.012439 0.364087 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6803(2) 0.09226(13) 0.40954(17) 0.0188(5) Uani 1 1 d . . . . .
C14 C 0.7791(3) 0.16437(17) 0.65214(19) 0.0314(6) Uani 1 1 d . . . . .
H14 H 0.737226 0.214510 0.636612 0.038 Uiso 1 1 calc R U . . .
C15 C 0.6921(4) 0.1307(2) 0.7296(2) 0.0428(8) Uani 1 1 d . . . . .
H15A H 0.591816 0.126149 0.709467 0.064 Uiso 1 1 calc R U . . .
H15B H 0.698836 0.163510 0.783376 0.064 Uiso 1 1 calc R U . . .
H15C H 0.729915 0.081046 0.745451 0.064 Uiso 1 1 calc R U . . .
C16 C 0.9338(4) 0.1767(2) 0.6848(2) 0.0462(8) Uani 1 1 d . . . . .
H16A H 0.975810 0.128667 0.703758 0.069 Uiso 1 1 calc R U . . .
H16B H 0.935772 0.211470 0.736757 0.069 Uiso 1 1 calc R U . . .
H16C H 0.988815 0.197893 0.634717 0.069 Uiso 1 1 calc R U . . .
C17 C 0.5886(2) 0.11254(15) 0.32578(16) 0.0207(5) Uani 1 1 d . . . . .
H17 H 0.565968 0.167281 0.328963 0.025 Uiso 1 1 calc R U . . .
C18 C 0.4473(3) 0.0689(2) 0.3278(2) 0.0365(7) Uani 1 1 d . . . . .
H18A H 0.466731 0.015121 0.322664 0.055 Uiso 1 1 calc R U . . .
H18B H 0.385231 0.084915 0.276484 0.055 Uiso 1 1 calc R U . . .
H18C H 0.399773 0.078952 0.385633 0.055 Uiso 1 1 calc R U . . .
C19 C 0.6613(3) 0.09746(17) 0.23476(18) 0.0297(6) Uani 1 1 d . . . . .
H19A H 0.749104 0.127222 0.231807 0.045 Uiso 1 1 calc R U . . .
H19B H 0.596484 0.111460 0.183909 0.045 Uiso 1 1 calc R U . . .
H19C H 0.684827 0.044049 0.230308 0.045 Uiso 1 1 calc R U . . .
C20 C 0.8563(3) 0.38920(15) 0.39956(19) 0.0260(5) Uani 1 1 d . . . . .
C21 C 0.7508(2) 0.28126(14) 0.31270(18) 0.0223(5) Uani 1 1 d . . . . .
C22 C 0.9289(3) 0.25790(14) 0.44403(17) 0.0211(5) Uani 1 1 d . . . . .
O5 O 1.0381(3) 0.07554(14) 0.20645(18) 0.0502(7) Uani 1 1 d . . . . .
H5 H 1.095556 0.093273 0.168755 0.075 Uiso 1 1 calc R U . . .
C23 C 1.0391(3) 0.12055(17) 0.2859(2) 0.0312(6) Uani 1 1 d . . . . .
H23A H 0.973163 0.099449 0.330260 0.047 Uiso 1 1 calc R U . . .
H23B H 1.008869 0.171574 0.269732 0.047 Uiso 1 1 calc R U . . .
H23C H 1.135894 0.121897 0.312974 0.047 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
Br1 Mn1 2.5377(4) . ?
Mn1 N1 2.0746(19) . ?
Mn1 N2 2.059(2) . ?
Mn1 C20 1.829(3) . ?
Mn1 C21 1.787(3) . ?
Mn1 C22 1.805(2) . ?
O1 H1 0.8400 . ?
O1 C1 1.337(3) . ?
O2 C20 1.138(3) . ?
O3 C21 1.150(3) . ?
O4 C22 1.149(3) . ?
N1 C1 1.330(3) . ?
N1 C5 1.370(3) . ?
N2 C6 1.287(3) . ?
N2 C8 1.453(3) . ?
C1 C2 1.405(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 C6 1.472(3) . ?
C6 C7 1.496(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.407(3) . ?
C8 C13 1.397(3) . ?
C9 C10 1.399(4) . ?
C9 C14 1.519(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.366(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.402(3) . ?
C13 C17 1.521(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.532(4) . ?
C14 C16 1.529(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 1.0000 . ?
C17 C18 1.534(4) . ?
C17 C19 1.532(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O5 H5 0.8400 . ?
O5 C23 1.411(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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 Mn1 Br1 85.94(5) . . ?
N2 Mn1 Br1 92.40(5) . . ?
N2 Mn1 N1 77.65(8) . . ?
C20 Mn1 Br1 82.49(9) . . ?
C20 Mn1 N1 99.57(9) . . ?
C20 Mn1 N2 174.38(10) . . ?
C21 Mn1 Br1 169.76(8) . . ?
C21 Mn1 N1 96.44(9) . . ?
C21 Mn1 N2 97.84(10) . . ?
C21 Mn1 C20 87.29(12) . . ?
C21 Mn1 C22 90.25(11) . . ?
C22 Mn1 Br1 88.71(8) . . ?
C22 Mn1 N1 170.26(9) . . ?
C22 Mn1 N2 94.47(9) . . ?
C22 Mn1 C20 87.77(11) . . ?
C1 O1 H1 109.5 . . ?
C1 N1 Mn1 128.50(15) . . ?
C1 N1 C5 117.60(19) . . ?
C5 N1 Mn1 113.23(15) . . ?
C6 N2 Mn1 117.00(16) . . ?
C6 N2 C8 119.57(19) . . ?
C8 N2 Mn1 123.44(14) . . ?
O1 C1 C2 122.1(2) . . ?
N1 C1 O1 115.56(19) . . ?
N1 C1 C2 122.3(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.8(2) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.9(2) . . ?
N1 C5 C6 114.22(19) . . ?
C4 C5 C6 122.8(2) . . ?
N2 C6 C5 115.4(2) . . ?
N2 C6 C7 125.5(2) . . ?
C5 C6 C7 119.0(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N2 119.2(2) . . ?
C13 C8 N2 118.2(2) . . ?
C13 C8 C9 122.6(2) . . ?
C8 C9 C14 122.9(2) . . ?
C10 C9 C8 117.0(2) . . ?
C10 C9 C14 120.1(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.7(2) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 117.4(2) . . ?
C8 C13 C17 123.5(2) . . ?
C12 C13 C17 119.0(2) . . ?
C9 C14 H14 107.8 . . ?
C9 C14 C15 111.6(2) . . ?
C9 C14 C16 111.8(3) . . ?
C15 C14 H14 107.8 . . ?
C16 C14 H14 107.8 . . ?
C16 C14 C15 110.0(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17 108.1 . . ?
C13 C17 C18 109.5(2) . . ?
C13 C17 C19 113.7(2) . . ?
C18 C17 H17 108.1 . . ?
C19 C17 H17 108.1 . . ?
C19 C17 C18 109.2(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 Mn1 174.3(2) . . ?
O3 C21 Mn1 173.2(2) . . ?
O4 C22 Mn1 178.5(2) . . ?
C23 O5 H5 109.5 . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
Mn1 N1 C1 O1 14.6(3) . . . . ?
Mn1 N1 C1 C2 -165.29(17) . . . . ?
Mn1 N1 C5 C4 167.09(19) . . . . ?
Mn1 N1 C5 C6 -15.6(2) . . . . ?
Mn1 N2 C6 C5 5.8(3) . . . . ?
Mn1 N2 C6 C7 -176.86(19) . . . . ?
Mn1 N2 C8 C9 89.9(2) . . . . ?
Mn1 N2 C8 C13 -89.6(2) . . . . ?
O1 C1 C2 C3 178.4(2) . . . . ?
N1 C1 C2 C3 -1.7(4) . . . . ?
N1 C5 C6 N2 6.7(3) . . . . ?
N1 C5 C6 C7 -170.8(2) . . . . ?
N2 C8 C9 C10 -176.6(2) . . . . ?
N2 C8 C9 C14 6.3(3) . . . . ?
N2 C8 C13 C12 176.55(19) . . . . ?
N2 C8 C13 C17 -8.2(3) . . . . ?
C1 N1 C5 C4 -4.3(3) . . . . ?
C1 N1 C5 C6 173.0(2) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C3 C4 C5 N1 1.1(4) . . . . ?
C3 C4 C5 C6 -176.0(2) . . . . ?
C4 C5 C6 N2 -175.9(2) . . . . ?
C4 C5 C6 C7 6.6(4) . . . . ?
C5 N1 C1 O1 -175.6(2) . . . . ?
C5 N1 C1 C2 4.6(3) . . . . ?
C6 N2 C8 C9 -90.1(3) . . . . ?
C6 N2 C8 C13 90.4(3) . . . . ?
C8 N2 C6 C5 -174.2(2) . . . . ?
C8 N2 C6 C7 3.1(4) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C8 C9 C14 C15 111.5(3) . . . . ?
C8 C9 C14 C16 -124.8(3) . . . . ?
C8 C13 C17 C18 -104.4(3) . . . . ?
C8 C13 C17 C19 133.1(2) . . . . ?
C9 C8 C13 C12 -2.9(3) . . . . ?
C9 C8 C13 C17 172.4(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C9 C14 C15 -65.5(3) . . . . ?
C10 C9 C14 C16 58.2(3) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C8 1.1(3) . . . . ?
C11 C12 C13 C17 -174.4(2) . . . . ?
C12 C13 C17 C18 70.8(3) . . . . ?
C12 C13 C17 C19 -51.6(3) . . . . ?
C13 C8 C9 C10 2.8(3) . . . . ?
C13 C8 C9 C14 -174.3(2) . . . . ?
C14 C9 C10 C11 176.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_15126
_database_code_depnum_ccdc_archive 'CCDC 2540715'
_audit_update_record             
;
2026-03-24 deposited with the CCDC.	2026-04-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 N2 O'
_chemical_formula_sum            'C19 H24 N2 O'
_chemical_formula_weight         296.40

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.866(2)
_cell_length_b                   12.571(3)
_cell_length_c                   15.275(3)
_cell_angle_alpha                91.980(4)
_cell_angle_beta                 100.619(4)
_cell_angle_gamma                94.830(4)
_cell_volume                     1665.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    981
_cell_measurement_theta_min      2.731
_cell_measurement_theta_max      25.783

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.507
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_process_details   
;
absorption correction based on 5388 reflections(SADABS);Rint 0.0684 before
correction and 0.0339 after.
;


_exptl_special_details           
; 

One of the isopropyl groups of one of the molecules is disordered and the 
methyl atoms have been split. 
  
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13003
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6446
_reflns_number_gt                4344
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0676P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6446
_refine_ls_number_parameters     427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_restrained_S_all      0.932
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47716(15) 0.58690(10) 0.57720(8) 0.0354(3) Uani 1 1 d . . .
N1 N 0.61748(16) 0.63379(11) 0.47145(9) 0.0239(3) Uani 1 1 d . . .
H1 H 0.5978 0.5686 0.4467 0.029 Uiso 1 1 calc R . .
N2 N 0.75917(16) 0.56975(11) 0.33721(9) 0.0235(3) Uani 1 1 d . . .
C1 C 0.5574(2) 0.65609(14) 0.54596(12) 0.0259(4) Uani 1 1 d . . .
C2 C 0.5936(2) 0.76346(15) 0.58292(12) 0.0316(5) Uani 1 1 d . . .
H2 H 0.5567 0.7839 0.6350 0.038 Uiso 1 1 calc R . .
C3 C 0.6789(2) 0.83614(15) 0.54532(12) 0.0327(5) Uani 1 1 d . . .
H3 H 0.7000 0.9071 0.5706 0.039 Uiso 1 1 calc R . .
C4 C 0.7370(2) 0.80770(14) 0.46892(12) 0.0287(4) Uani 1 1 d . . .
H4 H 0.7973 0.8591 0.4427 0.034 Uiso 1 1 calc R . .
C5 C 0.7061(2) 0.70628(13) 0.43311(11) 0.0233(4) Uani 1 1 d . . .
C6 C 0.7642(2) 0.67025(14) 0.35401(11) 0.0250(4) Uani 1 1 d . . .
C7 C 0.8254(2) 0.75576(15) 0.30019(13) 0.0372(5) Uani 1 1 d . . .
H7A H 0.8521 0.7229 0.2467 0.056 Uiso 1 1 calc R . .
H7B H 0.9175 0.7952 0.3361 0.056 Uiso 1 1 calc R . .
H7C H 0.7465 0.8051 0.2827 0.056 Uiso 1 1 calc R . .
C8 C 0.8148(2) 0.52893(13) 0.26229(11) 0.0237(4) Uani 1 1 d . . .
C9 C 0.9736(2) 0.53328(14) 0.26239(12) 0.0276(4) Uani 1 1 d . B .
C10 C 1.0198(2) 0.48894(15) 0.18840(13) 0.0351(5) Uani 1 1 d . . .
H10 H 1.1266 0.4915 0.1868 0.042 Uiso 1 1 calc R . .
C11 C 0.9147(2) 0.44122(16) 0.11708(13) 0.0372(5) Uani 1 1 d . . .
H11 H 0.9491 0.4123 0.0667 0.045 Uiso 1 1 calc R . .
C12 C 0.7598(2) 0.43563(15) 0.11920(12) 0.0331(5) Uani 1 1 d . . .
H12 H 0.6880 0.4019 0.0702 0.040 Uiso 1 1 calc R . .
C13 C 0.7062(2) 0.47835(14) 0.19156(12) 0.0267(4) Uani 1 1 d . . .
C14 C 0.5359(2) 0.47427(15) 0.19290(12) 0.0316(5) Uani 1 1 d . . .
H14 H 0.5248 0.4869 0.2563 0.038 Uiso 1 1 calc R . .
C15 C 0.4672(3) 0.5637(2) 0.14103(19) 0.0749(9) Uani 1 1 d . . .
H15A H 0.5190 0.6323 0.1675 0.112 Uiso 1 1 calc R . .
H15B H 0.3571 0.5614 0.1428 0.112 Uiso 1 1 calc R . .
H15C H 0.4807 0.5555 0.0790 0.112 Uiso 1 1 calc R . .
C16 C 0.4516(3) 0.3673(2) 0.1604(2) 0.0820(10) Uani 1 1 d . . .
H16A H 0.3461 0.3649 0.1717 0.123 Uiso 1 1 calc R . .
H16B H 0.5050 0.3107 0.1922 0.123 Uiso 1 1 calc R . .
H16C H 0.4487 0.3564 0.0963 0.123 Uiso 1 1 calc R . .
C17 C 1.0915(2) 0.58063(16) 0.34208(12) 0.0335(5) Uani 1 1 d . . .
H17 H 1.0382 0.6239 0.3812 0.040 Uiso 1 1 calc R A 1
C18B C 1.2184(12) 0.6544(7) 0.3110(7) 0.053(2) Uani 0.50 1 d P B 1
H18A H 1.2913 0.6865 0.3633 0.079 Uiso 0.50 1 calc PR B 1
H18B H 1.1709 0.7111 0.2763 0.079 Uiso 0.50 1 calc PR B 1
H18C H 1.2731 0.6124 0.2739 0.079 Uiso 0.50 1 calc PR B 1
C18C C 1.2495(13) 0.6099(8) 0.3258(8) 0.063(3) Uani 0.50 1 d P B 2
H18D H 1.3130 0.6460 0.3797 0.095 Uiso 0.50 1 calc PR B 2
H18E H 1.2445 0.6580 0.2764 0.095 Uiso 0.50 1 calc PR B 2
H18F H 1.2953 0.5451 0.3105 0.095 Uiso 0.50 1 calc PR B 2
C19B C 1.1614(9) 0.4933(7) 0.3941(6) 0.060(2) Uani 0.50 1 d P B 1
H19A H 1.2135 0.4501 0.3563 0.089 Uiso 0.50 1 calc PR B 1
H19B H 1.0805 0.4481 0.4144 0.089 Uiso 0.50 1 calc PR B 1
H19C H 1.2364 0.5243 0.4459 0.089 Uiso 0.50 1 calc PR B 1
C19C C 1.1000(9) 0.4987(7) 0.4188(6) 0.0513(19) Uani 0.50 1 d P B 2
H19G H 1.1314 0.4310 0.3977 0.077 Uiso 0.50 1 calc PR B 2
H19H H 0.9985 0.4863 0.4352 0.077 Uiso 0.50 1 calc PR B 2
H19I H 1.1754 0.5282 0.4709 0.077 Uiso 0.50 1 calc PR B 2
O1A O 1.12406(15) 0.92819(10) 0.47037(8) 0.0363(3) Uani 1 1 d . . .
N1A N 1.06210(16) 0.91028(11) 0.60748(9) 0.0256(4) Uani 1 1 d . . .
H1A H 1.0246 0.9730 0.6041 0.031 Uiso 1 1 calc R . .
N2A N 0.97584(18) 1.00563(12) 0.75097(9) 0.0286(4) Uani 1 1 d . . .
C1A C 1.1270(2) 0.87568(14) 0.53771(12) 0.0266(4) Uani 1 1 d . . .
C2A C 1.1952(2) 0.77676(14) 0.55045(12) 0.0298(4) Uani 1 1 d . . .
H2A H 1.2469 0.7497 0.5064 0.036 Uiso 1 1 calc R . .
C3A C 1.1877(2) 0.72133(14) 0.62346(12) 0.0321(5) Uani 1 1 d . . .
H3A H 1.2337 0.6558 0.6300 0.039 Uiso 1 1 calc R . .
C4A C 1.1130(2) 0.75880(14) 0.69014(12) 0.0304(4) Uani 1 1 d . . .
H4A H 1.1054 0.7180 0.7406 0.036 Uiso 1 1 calc R . .
C5A C 1.0516(2) 0.85422(14) 0.68179(11) 0.0251(4) Uani 1 1 d . . .
C6A C 0.9780(2) 0.90470(14) 0.75050(11) 0.0269(4) Uani 1 1 d . . .
C7A C 0.9122(2) 0.83166(15) 0.81290(13) 0.0388(5) Uani 1 1 d . . .
H7A1 H 0.8710 0.8743 0.8564 0.058 Uiso 1 1 calc R . .
H7A2 H 0.9935 0.7910 0.8442 0.058 Uiso 1 1 calc R . .
H7A3 H 0.8293 0.7821 0.7787 0.058 Uiso 1 1 calc R . .
C8A C 0.9139(2) 1.06624(14) 0.81399(11) 0.0286(4) Uani 1 1 d . . .
C9A C 1.0194(2) 1.12804(14) 0.88112(12) 0.0322(5) Uani 1 1 d . . .
C10A C 0.9615(3) 1.20062(15) 0.93369(12) 0.0391(5) Uani 1 1 d . . .
H10A H 1.0306 1.2432 0.9789 0.047 Uiso 1 1 calc R . .
C11A C 0.8067(3) 1.21236(16) 0.92200(13) 0.0435(6) Uani 1 1 d . . .
H11A H 0.7700 1.2637 0.9581 0.052 Uiso 1 1 calc R . .
C12A C 0.7046(3) 1.14972(16) 0.85802(13) 0.0407(5) Uani 1 1 d . . .
H12A H 0.5976 1.1578 0.8511 0.049 Uiso 1 1 calc R . .
C13A C 0.7548(2) 1.07516(15) 0.80355(12) 0.0334(5) Uani 1 1 d . . .
C14A C 1.1888(2) 1.11164(16) 0.89619(13) 0.0379(5) Uani 1 1 d . . .
H14A H 1.2169 1.0995 0.8364 0.045 Uiso 1 1 calc R . .
C15A C 1.2922(3) 1.2077(2) 0.94311(15) 0.0585(7) Uani 1 1 d . . .
H15D H 1.2756 1.2167 1.0045 0.088 Uiso 1 1 calc R . .
H15E H 1.2672 1.2722 0.9112 0.088 Uiso 1 1 calc R . .
H15F H 1.4003 1.1961 0.9437 0.088 Uiso 1 1 calc R . .
C16A C 1.2229(3) 1.01283(18) 0.94889(14) 0.0475(6) Uani 1 1 d . . .
H16D H 1.1920 1.0211 1.0070 0.071 Uiso 1 1 calc R . .
H16E H 1.3334 1.0044 0.9578 0.071 Uiso 1 1 calc R . .
H16F H 1.1650 0.9495 0.9158 0.071 Uiso 1 1 calc R . .
C17A C 0.6373(2) 1.00792(16) 0.73415(13) 0.0385(5) Uani 1 1 d . . .
H17A H 0.6913 0.9495 0.7108 0.046 Uiso 1 1 calc R . .
C18A C 0.5049(3) 0.95507(19) 0.77407(17) 0.0604(7) Uani 1 1 d . . .
H18G H 0.5472 0.9150 0.8254 0.091 Uiso 1 1 calc R . .
H18H H 0.4384 0.9062 0.7289 0.091 Uiso 1 1 calc R . .
H18I H 0.4447 1.0103 0.7934 0.091 Uiso 1 1 calc R . .
C19A C 0.5759(3) 1.0738(2) 0.65565(14) 0.0557(7) Uani 1 1 d . . .
H20G H 0.5241 1.1328 0.6767 0.084 Uiso 1 1 calc R . .
H19E H 0.5024 1.0283 0.6112 0.084 Uiso 1 1 calc R . .
H19F H 0.6617 1.1026 0.6286 0.084 Uiso 1 1 calc R . .


_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 C1 1.241(2) . ?
N1 C5 1.370(2) . ?
N1 C1 1.373(2) . ?
N1 H1 0.8800 . ?
N2 C6 1.276(2) . ?
N2 C8 1.423(2) . ?
C1 C2 1.432(2) . ?
C2 C3 1.348(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.355(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.470(2) . ?
C6 C7 1.501(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.401(2) . ?
C8 C9 1.404(2) . ?
C9 C10 1.386(2) . ?
C9 C17 1.518(3) . ?
C10 C11 1.379(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.510(3) . ?
C14 C15 1.504(3) . ?
C14 C16 1.504(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18C 1.486(12) . ?
C17 C19B 1.488(9) . ?
C17 C18B 1.550(10) . ?
C17 C19C 1.582(10) . ?
C17 H17 1.0000 . ?
C18B H18A 0.9800 . ?
C18B H18B 0.9800 . ?
C18B H18C 0.9800 . ?
C18C H18D 0.9800 . ?
C18C H18E 0.9800 . ?
C18C H18F 0.9800 . ?
C19B H19A 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H19C 0.9800 . ?
C19C H19G 0.9800 . ?
C19C H19H 0.9800 . ?
C19C H19I 0.9800 . ?
O1A C1A 1.239(2) . ?
N1A C5A 1.370(2) . ?
N1A C1A 1.376(2) . ?
N1A H1A 0.8800 . ?
N2A C6A 1.270(2) . ?
N2A C8A 1.422(2) . ?
C1A C2A 1.432(3) . ?
C2A C3A 1.344(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.402(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.359(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.485(2) . ?
C6A C7A 1.506(2) . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C8A C13A 1.404(3) . ?
C8A C9A 1.414(3) . ?
C9A C10A 1.386(3) . ?
C9A C14A 1.509(3) . ?
C10A C11A 1.371(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.377(3) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.386(3) . ?
C12A H12A 0.9500 . ?
C13A C17A 1.519(3) . ?
C14A C16A 1.525(3) . ?
C14A C15A 1.525(3) . ?
C14A H14A 1.0000 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
C17A C19A 1.524(3) . ?
C17A C18A 1.533(3) . ?
C17A H17A 1.0000 . ?
C18A H18G 0.9800 . ?
C18A H18H 0.9800 . ?
C18A H18I 0.9800 . ?
C19A H20G 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?

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
C5 N1 C1 124.31(15) . . ?
C5 N1 H1 117.8 . . ?
C1 N1 H1 117.8 . . ?
C6 N2 C8 120.79(14) . . ?
O1 C1 N1 121.18(16) . . ?
O1 C1 C2 123.78(16) . . ?
N1 C1 C2 115.04(15) . . ?
C3 C2 C1 121.39(17) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.53(17) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.37(16) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 N1 119.35(15) . . ?
C4 C5 C6 122.51(15) . . ?
N1 C5 C6 118.13(15) . . ?
N2 C6 C5 117.63(15) . . ?
N2 C6 C7 125.69(16) . . ?
C5 C6 C7 116.68(15) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 121.54(16) . . ?
C13 C8 N2 117.59(15) . . ?
C9 C8 N2 120.75(15) . . ?
C10 C9 C8 117.68(17) . . ?
C10 C9 C17 120.82(17) . . ?
C8 C9 C17 121.46(16) . . ?
C11 C10 C9 121.70(18) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 119.69(18) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.36(18) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 117.99(17) . . ?
C12 C13 C14 121.28(16) . . ?
C8 C13 C14 120.69(16) . . ?
C15 C14 C16 111.9(2) . . ?
C15 C14 C13 109.71(16) . . ?
C16 C14 C13 112.75(17) . . ?
C15 C14 H14 107.4 . . ?
C16 C14 H14 107.4 . . ?
C13 C14 H14 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18C C17 C19B 85.3(4) . . ?
C18C C17 C9 116.3(5) . . ?
C19B C17 C9 109.8(4) . . ?
C19B C17 C18B 110.2(5) . . ?
C9 C17 C18B 110.5(4) . . ?
C18C C17 C19C 109.1(4) . . ?
C9 C17 C19C 108.3(4) . . ?
C18B C17 C19C 131.5(5) . . ?
C18C C17 H17 124.3 . . ?
C19B C17 H17 108.8 . . ?
C9 C17 H17 108.8 . . ?
C18B C17 H17 108.8 . . ?
C19C C17 H17 84.5 . . ?
C17 C18B H18A 109.5 . . ?
C17 C18B H18B 109.5 . . ?
C17 C18B H18C 109.5 . . ?
C17 C18C H18D 109.5 . . ?
C17 C18C H18E 109.5 . . ?
H18D C18C H18E 109.5 . . ?
C17 C18C H18F 109.5 . . ?
H18D C18C H18F 109.5 . . ?
H18E C18C H18F 109.5 . . ?
C17 C19B H19A 109.5 . . ?
C17 C19B H19B 109.5 . . ?
C17 C19B H19C 109.5 . . ?
C17 C19C H19G 109.5 . . ?
C17 C19C H19H 109.5 . . ?
H19G C19C H19H 109.5 . . ?
C17 C19C H19I 109.5 . . ?
H19G C19C H19I 109.5 . . ?
H19H C19C H19I 109.5 . . ?
C5A N1A C1A 124.73(15) . . ?
C5A N1A H1A 117.6 . . ?
C1A N1A H1A 117.6 . . ?
C6A N2A C8A 123.83(15) . . ?
O1A C1A N1A 120.86(16) . . ?
O1A C1A C2A 124.56(16) . . ?
N1A C1A C2A 114.58(15) . . ?
C3A C2A C1A 121.39(17) . . ?
C3A C2A H2A 119.3 . . ?
C1A C2A H2A 119.3 . . ?
C2A C3A C4A 120.98(18) . . ?
C2A C3A H3A 119.5 . . ?
C4A C3A H3A 119.5 . . ?
C5A C4A C3A 119.25(17) . . ?
C5A C4A H4A 120.4 . . ?
C3A C4A H4A 120.4 . . ?
C4A C5A N1A 118.93(16) . . ?
C4A C5A C6A 123.94(16) . . ?
N1A C5A C6A 117.08(15) . . ?
N2A C6A C5A 116.94(15) . . ?
N2A C6A C7A 125.96(17) . . ?
C5A C6A C7A 117.11(16) . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C13A C8A C9A 120.85(17) . . ?
C13A C8A N2A 121.26(16) . . ?
C9A C8A N2A 117.42(17) . . ?
C10A C9A C8A 117.92(19) . . ?
C10A C9A C14A 121.76(18) . . ?
C8A C9A C14A 120.29(17) . . ?
C11A C10A C9A 121.59(19) . . ?
C11A C10A H10A 119.2 . . ?
C9A C10A H10A 119.2 . . ?
C10A C11A C12A 119.98(19) . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C11A C12A C13A 121.4(2) . . ?
C11A C12A H12A 119.3 . . ?
C13A C12A H12A 119.3 . . ?
C12A C13A C8A 118.22(18) . . ?
C12A C13A C17A 119.25(19) . . ?
C8A C13A C17A 122.52(16) . . ?
C9A C14A C16A 111.34(16) . . ?
C9A C14A C15A 113.40(18) . . ?
C16A C14A C15A 109.09(18) . . ?
C9A C14A H14A 107.6 . . ?
C16A C14A H14A 107.6 . . ?
C15A C14A H14A 107.6 . . ?
C14A C15A H15D 109.5 . . ?
C14A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C14A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C14A C16A H16D 109.5 . . ?
C14A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C14A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C13A C17A C19A 111.03(17) . . ?
C13A C17A C18A 112.14(17) . . ?
C19A C17A C18A 110.9(2) . . ?
C13A C17A H17A 107.5 . . ?
C19A C17A H17A 107.5 . . ?
C18A C17A H17A 107.5 . . ?
C17A C18A H18G 109.5 . . ?
C17A C18A H18H 109.5 . . ?
H18G C18A H18H 109.5 . . ?
C17A C18A H18I 109.5 . . ?
H18G C18A H18I 109.5 . . ?
H18H C18A H18I 109.5 . . ?
C17A C19A H20G 109.5 . . ?
C17A C19A H19E 109.5 . . ?
H20G C19A H19E 109.5 . . ?
C17A C19A H19F 109.5 . . ?
H20G C19A H19F 109.5 . . ?
H19E C19A H19F 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
C5 N1 C1 O1 179.62(17) . . . . ?
C5 N1 C1 C2 0.0(2) . . . . ?
O1 C1 C2 C3 -178.71(19) . . . . ?
N1 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 N1 0.7(3) . . . . ?
C3 C4 C5 C6 -179.26(17) . . . . ?
C1 N1 C5 C4 -0.8(3) . . . . ?
C1 N1 C5 C6 179.17(15) . . . . ?
C8 N2 C6 C5 -179.38(15) . . . . ?
C8 N2 C6 C7 0.3(3) . . . . ?
C4 C5 C6 N2 164.61(17) . . . . ?
N1 C5 C6 N2 -15.4(2) . . . . ?
C4 C5 C6 C7 -15.1(3) . . . . ?
N1 C5 C6 C7 164.91(16) . . . . ?
C6 N2 C8 C13 -111.00(18) . . . . ?
C6 N2 C8 C9 73.1(2) . . . . ?
C13 C8 C9 C10 2.2(3) . . . . ?
N2 C8 C9 C10 177.96(16) . . . . ?
C13 C8 C9 C17 -175.30(16) . . . . ?
N2 C8 C9 C17 0.4(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C17 C9 C10 C11 177.01(17) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 C8 0.9(3) . . . . ?
C11 C12 C13 C14 178.65(17) . . . . ?
C9 C8 C13 C12 -2.4(3) . . . . ?
N2 C8 C13 C12 -178.26(15) . . . . ?
C9 C8 C13 C14 179.81(16) . . . . ?
N2 C8 C13 C14 3.9(2) . . . . ?
C12 C13 C14 C15 -81.5(2) . . . . ?
C8 C13 C14 C15 96.3(2) . . . . ?
C12 C13 C14 C16 44.0(3) . . . . ?
C8 C13 C14 C16 -138.3(2) . . . . ?
C10 C9 C17 C18C 19.8(4) . . . . ?
C8 C9 C17 C18C -162.8(4) . . . . ?
C10 C9 C17 C19B -74.9(4) . . . . ?
C8 C9 C17 C19B 102.6(3) . . . . ?
C10 C9 C17 C18B 46.8(4) . . . . ?
C8 C9 C17 C18B -135.7(4) . . . . ?
C10 C9 C17 C19C -103.5(3) . . . . ?
C8 C9 C17 C19C 74.0(3) . . . . ?
C5A N1A C1A O1A 175.72(16) . . . . ?
C5A N1A C1A C2A -4.2(2) . . . . ?
O1A C1A C2A C3A -176.74(18) . . . . ?
N1A C1A C2A C3A 3.2(3) . . . . ?
C1A C2A C3A C4A -0.2(3) . . . . ?
C2A C3A C4A C5A -2.0(3) . . . . ?
C3A C4A C5A N1A 1.1(3) . . . . ?
C3A C4A C5A C6A -176.32(17) . . . . ?
C1A N1A C5A C4A 2.1(3) . . . . ?
C1A N1A C5A C6A 179.78(16) . . . . ?
C8A N2A C6A C5A -178.09(16) . . . . ?
C8A N2A C6A C7A 2.3(3) . . . . ?
C4A C5A C6A N2A 155.38(18) . . . . ?
N1A C5A C6A N2A -22.1(2) . . . . ?
C4A C5A C6A C7A -24.9(3) . . . . ?
N1A C5A C6A C7A 157.56(16) . . . . ?
C6A N2A C8A C13A -81.5(2) . . . . ?
C6A N2A C8A C9A 106.4(2) . . . . ?
C13A C8A C9A C10A -2.6(3) . . . . ?
N2A C8A C9A C10A 169.61(16) . . . . ?
C13A C8A C9A C14A 175.32(16) . . . . ?
N2A C8A C9A C14A -12.5(2) . . . . ?
C8A C9A C10A C11A 0.4(3) . . . . ?
C14A C9A C10A C11A -177.45(18) . . . . ?
C9A C10A C11A C12A 1.3(3) . . . . ?
C10A C11A C12A C13A -0.9(3) . . . . ?
C11A C12A C13A C8A -1.2(3) . . . . ?
C11A C12A C13A C17A 179.86(18) . . . . ?
C9A C8A C13A C12A 3.0(3) . . . . ?
N2A C8A C13A C12A -168.92(16) . . . . ?
C9A C8A C13A C17A -178.14(16) . . . . ?
N2A C8A C13A C17A 10.0(3) . . . . ?
C10A C9A C14A C16A 99.4(2) . . . . ?
C8A C9A C14A C16A -78.4(2) . . . . ?
C10A C9A C14A C15A -24.1(3) . . . . ?
C8A C9A C14A C15A 158.11(17) . . . . ?
C12A C13A C17A C19A 74.3(2) . . . . ?
C8A C13A C17A C19A -104.6(2) . . . . ?
C12A C13A C17A C18A -50.4(3) . . . . ?
C8A C13A C17A C18A 130.7(2) . . . . ?

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
N1 H1 O1 0.88 2.01 2.8617(19) 162.5 2_666
N1A H1A O1A 0.88 2.10 2.876(2) 147.0 2_776

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.048

