# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_Eu-DMAPA1-3
_database_code_depnum_ccdc_archive 'CCDC 2278528'
loop_
_audit_author_name
_audit_author_address
'Chao Xu'
;Harbin Engineering University
China
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_audit_creation_date             2021-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 Eu N6 O9'
_chemical_formula_sum            'C27 H27 Eu N6 O9'
_chemical_formula_weight         731.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1O1Eu1
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'
Eu Eu -0.1578 3.6682 '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      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                   14.7029(8)
_cell_length_b                   20.7207(13)
_cell_length_c                   12.2192(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.685(6)
_cell_angle_gamma                90
_cell_volume                     3546.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5505
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.3710
_cell_measurement_theta_min      3.6170
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.712
_exptl_absorpt_coefficient_mu    1.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19319
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.799
_diffrn_reflns_theta_min         3.289
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  15.00   1.00    2.00    --  -11.20 -99.00 -60.00   29
  2  ω     -5.00  21.00   1.00    2.00    --   12.61  37.00 -90.00   26
  3  ω     -3.00  25.00   1.00    2.00    --   12.61  37.00 -60.00   28
  4  ω     27.00  81.00   1.00    2.00    --   12.61  37.00 -60.00   54
  5  ω    -58.00  21.00   1.00    2.00    --   12.61 -37.00 120.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0434846000
_diffrn_orient_matrix_UB_12      0.0035346000
_diffrn_orient_matrix_UB_13      0.0131728000
_diffrn_orient_matrix_UB_21      0.0125012000
_diffrn_orient_matrix_UB_22      0.0322639000
_diffrn_orient_matrix_UB_23      0.0177641000
_diffrn_orient_matrix_UB_31      -0.0227100000
_diffrn_orient_matrix_UB_32      0.0109464000
_diffrn_orient_matrix_UB_33      -0.0567473000
_diffrn_oxdiff_digest_frames     
;
01abdf40b1725b575e98f0ba33978a39c9002282ccd
;
_diffrn_oxdiff_digest_hkl        
;
0129d883aab71872b8a9c201b12bc283d96f51
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                5842
_reflns_number_total             8428
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.908
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         8428
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.006
_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)+(0.0369P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1084
_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
2. Restrained distances
 H17C-H14
 2.1 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N4) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C21(H21), C22(H22),
 C23(H23)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C),
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_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
Eu1 Eu 0.29449(2) 0.42338(2) 0.68668(2) 0.03102(9) Uani 1 1 d . . . . .
O1 O 0.2784(2) 0.44835(16) 0.8727(3) 0.0408(8) Uani 1 1 d . . . . .
O2 O 0.3316(3) 0.43524(17) 1.0631(3) 0.0567(11) Uani 1 1 d . . . . .
O3 O 0.4424(2) 0.40195(15) 0.6400(2) 0.0348(7) Uani 1 1 d . . . . .
O4 O 0.3521(2) 0.52969(16) 0.6747(2) 0.0378(8) Uani 1 1 d . . . . .
O5 O 0.3341(3) 0.63581(18) 0.6482(4) 0.0697(12) Uani 1 1 d . . . . .
O6 O 0.1299(2) 0.39156(17) 0.6602(3) 0.0476(9) Uani 1 1 d . . . . .
O7 O 0.2347(2) 0.43235(15) 0.4795(3) 0.0375(8) Uani 1 1 d . . . . .
O8 O 0.1797(2) 0.38885(18) 0.3037(2) 0.0457(9) Uani 1 1 d . . . . .
O9 O 0.3268(2) 0.32242(15) 0.7984(2) 0.0340(7) Uani 1 1 d . . . . .
N1 N 0.4486(3) 0.42963(17) 0.8506(3) 0.0322(9) Uani 1 1 d . . . . .
N2 N 0.5902(3) 0.44095(19) 0.6646(3) 0.0392(10) Uani 1 1 d . . . . .
N3 N 0.1721(3) 0.5136(2) 0.6593(3) 0.0406(10) Uani 1 1 d . . . . .
N4 N -0.0111(4) 0.4083(3) 0.6862(6) 0.0912(18) Uani 1 1 d . U . . .
N5 N 0.2663(2) 0.31669(18) 0.5758(3) 0.0287(8) Uani 1 1 d . . . . .
N6 N 0.3879(2) 0.22196(18) 0.8178(3) 0.0329(9) Uani 1 1 d . . . . .
C1 C 0.3433(4) 0.4371(2) 0.9666(4) 0.0461(13) Uani 1 1 d . . . . .
C2 C 0.4425(4) 0.4273(2) 0.9578(4) 0.0366(11) Uani 1 1 d . . . . .
C3 C 0.5209(4) 0.4145(2) 1.0517(4) 0.0454(14) Uani 1 1 d . . . . .
H3 H 0.5158 0.4135 1.1257 0.054 Uiso 1 1 calc R . . . .
C4 C 0.6070(4) 0.4035(3) 1.0317(4) 0.0531(15) Uani 1 1 d . . . . .
H4 H 0.6610 0.3942 1.0928 0.064 Uiso 1 1 calc R . . . .
C5 C 0.6135(4) 0.4064(2) 0.9207(4) 0.0476(13) Uani 1 1 d . . . . .
H5 H 0.6712 0.3983 0.9066 0.057 Uiso 1 1 calc R . . . .
C6 C 0.5330(3) 0.4213(2) 0.8323(4) 0.0325(10) Uani 1 1 d . . . . .
C7 C 0.5209(3) 0.4221(2) 0.7050(4) 0.0321(10) Uani 1 1 d . . . . .
C8 C 0.5797(4) 0.4335(3) 0.5419(5) 0.0584(15) Uani 1 1 d . . . . .
H8A H 0.5150 0.4219 0.5013 0.088 Uiso 1 1 calc GR . . . .
H8B H 0.6220 0.4002 0.5320 0.088 Uiso 1 1 calc GR . . . .
H8C H 0.5954 0.4735 0.5121 0.088 Uiso 1 1 calc GR . . . .
C9 C 0.6810(3) 0.4704(3) 0.7338(5) 0.0556(15) Uani 1 1 d . . . . .
H9A H 0.6730 0.4887 0.8024 0.083 Uiso 1 1 calc GR . . . .
H9B H 0.6992 0.5037 0.6899 0.083 Uiso 1 1 calc GR . . . .
H9C H 0.7299 0.4379 0.7540 0.083 Uiso 1 1 calc GR . . . .
C10 C 0.3040(4) 0.5808(3) 0.6566(4) 0.0445(13) Uani 1 1 d . . . . .
C11 C 0.1983(4) 0.5731(3) 0.6461(4) 0.0456(13) Uani 1 1 d . . . . .
C12 C 0.1344(4) 0.6243(3) 0.6198(6) 0.0745(19) Uani 1 1 d . . . . .
H12 H 0.1549 0.6661 0.6125 0.089 Uiso 1 1 calc R . . . .
C13 C 0.0400(5) 0.6110(3) 0.6049(7) 0.089(2) Uani 1 1 d . . . . .
H13 H -0.0051 0.6438 0.5834 0.107 Uiso 1 1 calc R . . . .
C14 C 0.0121(4) 0.5501(3) 0.6213(7) 0.083(2) Uani 1 1 d . . . . .
H14 H -0.0518 0.5410 0.6124 0.100 Uiso 1 1 calc DR . . . .
C15 C 0.0809(4) 0.5012(3) 0.6519(5) 0.0537(14) Uani 1 1 d . . . . .
C16 C 0.0667(4) 0.4302(3) 0.6678(5) 0.0584(16) Uani 1 1 d . . . . .
C17 C -0.0836(6) 0.4483(5) 0.7178(10) 0.159(4) Uani 1 1 d . U . . .
H17A H -0.0526 0.4843 0.7637 0.239 Uiso 1 1 calc GR . . . .
H17B H -0.1150 0.4226 0.7609 0.239 Uiso 1 1 calc GR . . . .
H17C H -0.1299 0.4639 0.6493 0.239 Uiso 1 1 calc DGR . . . .
C18 C -0.0266(5) 0.3387(4) 0.6881(8) 0.120(3) Uani 1 1 d . U . . .
H18A H 0.0129 0.3170 0.6500 0.179 Uiso 1 1 calc GR . . . .
H18B H -0.0925 0.3292 0.6494 0.179 Uiso 1 1 calc GR . . . .
H18C H -0.0105 0.3241 0.7663 0.179 Uiso 1 1 calc GR . . . .
C19 C 0.2108(3) 0.3854(3) 0.4093(4) 0.0361(11) Uani 1 1 d . . . . .
C20 C 0.2191(3) 0.3182(2) 0.4628(3) 0.0313(10) Uani 1 1 d . . . . .
C21 C 0.1816(3) 0.2635(3) 0.4020(4) 0.0403(12) Uani 1 1 d . . . . .
H21 H 0.1514 0.2656 0.3233 0.048 Uiso 1 1 calc R . . . .
C22 C 0.1893(3) 0.2057(3) 0.4590(4) 0.0455(13) Uani 1 1 d . . . . .
H22 H 0.1620 0.1686 0.4199 0.055 Uiso 1 1 calc R . . . .
C23 C 0.2385(3) 0.2034(2) 0.5759(4) 0.0407(12) Uani 1 1 d . . . . .
H23 H 0.2441 0.1649 0.6166 0.049 Uiso 1 1 calc R . . . .
C24 C 0.2786(3) 0.2595(2) 0.6294(3) 0.0289(10) Uani 1 1 d . . . . .
C25 C 0.3342(3) 0.2688(2) 0.7574(3) 0.0296(10) Uani 1 1 d . . . . .
C26 C 0.4125(3) 0.1609(2) 0.7744(4) 0.0415(12) Uani 1 1 d . . . . .
H26A H 0.3743 0.1269 0.7910 0.062 Uiso 1 1 calc GR . . . .
H26B H 0.4788 0.1516 0.8107 0.062 Uiso 1 1 calc GR . . . .
H26C H 0.4005 0.1639 0.6928 0.062 Uiso 1 1 calc GR . . . .
C27 C 0.4390(3) 0.2345(2) 0.9392(3) 0.0395(11) Uani 1 1 d . . . . .
H27A H 0.5035 0.2471 0.9469 0.059 Uiso 1 1 calc GR . . . .
H27B H 0.4394 0.1960 0.9832 0.059 Uiso 1 1 calc GR . . . .
H27C H 0.4075 0.2685 0.9670 0.059 Uiso 1 1 calc GR . . . .


_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
Eu1 O1 2.412(3) . ?
Eu1 O3 2.451(3) . ?
Eu1 O4 2.380(3) . ?
Eu1 O6 2.433(3) . ?
Eu1 O7 2.422(3) . ?
Eu1 O9 2.464(3) . ?
Eu1 N1 2.531(3) . ?
Eu1 N3 2.545(4) . ?
Eu1 N5 2.560(4) . ?
Eu1 C7 3.268(4) . ?
O1 C1 1.271(6) . ?
O2 C1 1.243(6) . ?
O3 C7 1.257(5) . ?
O4 C10 1.256(6) . ?
O5 C10 1.237(6) . ?
O6 C16 1.251(6) . ?
O7 C19 1.273(5) . ?
O8 C19 1.234(5) . ?
O9 C25 1.237(5) . ?
N1 C2 1.341(6) . ?
N1 C6 1.338(6) . ?
N2 C7 1.318(6) . ?
N2 C8 1.469(6) . ?
N2 C9 1.478(6) . ?
N3 C11 1.317(6) . ?
N3 C15 1.340(6) . ?
N4 C16 1.312(7) . ?
N4 C17 1.491(9) . ?
N4 C18 1.462(9) . ?
N5 C20 1.344(5) . ?
N5 C24 1.340(5) . ?
N6 C25 1.325(5) . ?
N6 C26 1.460(6) . ?
N6 C27 1.469(5) . ?
C1 C2 1.508(8) . ?
C2 C3 1.383(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(6) . ?
C6 C7 1.512(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.528(7) . ?
C11 C12 1.388(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.362(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(7) . ?
C15 C16 1.508(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.529(7) . ?
C20 C21 1.375(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.392(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.376(6) . ?
C24 C25 1.541(6) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Eu1 O3 127.34(10) . . ?
O1 Eu1 O6 78.75(11) . . ?
O1 Eu1 O7 149.37(11) . . ?
O1 Eu1 O9 73.60(10) . . ?
O1 Eu1 N1 64.13(12) . . ?
O1 Eu1 N3 72.43(11) . . ?
O1 Eu1 N5 129.60(11) . . ?
O1 Eu1 C7 109.09(11) . . ?
O3 Eu1 O9 86.56(10) . . ?
O3 Eu1 N1 63.22(11) . . ?
O3 Eu1 N3 138.13(12) . . ?
O3 Eu1 N5 74.51(10) . . ?
O3 Eu1 C7 19.43(10) . . ?
O4 Eu1 O1 89.89(11) . . ?
O4 Eu1 O3 78.22(11) . . ?
O4 Eu1 O6 126.92(11) . . ?
O4 Eu1 O7 83.54(10) . . ?
O4 Eu1 O9 143.86(9) . . ?
O4 Eu1 N1 75.62(10) . . ?
O4 Eu1 N3 64.10(12) . . ?
O4 Eu1 N5 140.37(11) . . ?
O4 Eu1 C7 68.77(11) . . ?
O6 Eu1 O3 146.82(11) . . ?
O6 Eu1 O9 81.95(11) . . ?
O6 Eu1 N1 137.23(12) . . ?
O6 Eu1 N3 63.03(12) . . ?
O6 Eu1 N5 72.58(11) . . ?
O6 Eu1 C7 163.36(11) . . ?
O7 Eu1 O3 80.57(10) . . ?
O7 Eu1 O6 81.46(11) . . ?
O7 Eu1 O9 126.29(10) . . ?
O7 Eu1 N1 140.97(11) . . ?
O7 Eu1 N3 77.82(11) . . ?
O7 Eu1 N5 64.15(10) . . ?
O7 Eu1 C7 96.35(11) . . ?
O9 Eu1 N1 68.25(10) . . ?
O9 Eu1 N3 134.88(11) . . ?
O9 Eu1 N5 62.15(10) . . ?
O9 Eu1 C7 86.23(10) . . ?
N1 Eu1 N3 119.58(12) . . ?
N1 Eu1 N5 115.17(11) . . ?
N1 Eu1 C7 45.42(12) . . ?
N3 Eu1 N5 124.75(11) . . ?
N3 Eu1 C7 132.86(12) . . ?
N5 Eu1 C7 91.55(11) . . ?
C1 O1 Eu1 123.3(3) . . ?
C7 O3 Eu1 120.1(3) . . ?
C10 O4 Eu1 126.9(3) . . ?
C16 O6 Eu1 123.2(3) . . ?
C19 O7 Eu1 125.7(3) . . ?
C25 O9 Eu1 124.3(3) . . ?
C2 N1 Eu1 117.5(3) . . ?
C6 N1 Eu1 120.9(3) . . ?
C6 N1 C2 120.0(4) . . ?
C7 N2 C8 119.9(4) . . ?
C7 N2 C9 125.1(4) . . ?
C8 N2 C9 115.0(4) . . ?
C11 N3 Eu1 118.8(3) . . ?
C11 N3 C15 119.7(4) . . ?
C15 N3 Eu1 121.4(4) . . ?
C16 N4 C17 125.5(7) . . ?
C16 N4 C18 119.5(6) . . ?
C18 N4 C17 114.7(6) . . ?
C20 N5 Eu1 118.3(3) . . ?
C24 N5 Eu1 122.0(2) . . ?
C24 N5 C20 118.2(4) . . ?
C25 N6 C26 127.2(4) . . ?
C25 N6 C27 118.0(4) . . ?
C26 N6 C27 114.4(4) . . ?
O1 C1 C2 116.0(4) . . ?
O2 C1 O1 125.4(6) . . ?
O2 C1 C2 118.6(5) . . ?
N1 C2 C1 114.7(4) . . ?
N1 C2 C3 122.1(5) . . ?
C3 C2 C1 123.2(5) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 C2 117.6(5) . . ?
C4 C3 H3 121.2 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(5) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.6(5) . . ?
C6 C5 H5 120.7 . . ?
N1 C6 C5 121.3(4) . . ?
N1 C6 C7 110.2(4) . . ?
C5 C6 C7 128.0(5) . . ?
O3 C7 Eu1 40.4(2) . . ?
O3 C7 N2 121.8(4) . . ?
O3 C7 C6 116.4(4) . . ?
N2 C7 Eu1 149.1(3) . . ?
N2 C7 C6 121.7(4) . . ?
C6 C7 Eu1 82.5(3) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 C11 115.5(5) . . ?
O5 C10 O4 126.5(5) . . ?
O5 C10 C11 118.0(5) . . ?
N3 C11 C10 114.6(4) . . ?
N3 C11 C12 122.7(5) . . ?
C12 C11 C10 122.6(5) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 C11 117.6(6) . . ?
C13 C12 H12 121.2 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(6) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 118.9(6) . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 120.5(6) . . ?
N3 C15 C16 110.6(4) . . ?
C14 C15 C16 128.6(5) . . ?
O6 C16 N4 119.8(6) . . ?
O6 C16 C15 118.7(5) . . ?
N4 C16 C15 121.4(5) . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 C20 116.0(4) . . ?
O8 C19 O7 126.8(5) . . ?
O8 C19 C20 117.1(4) . . ?
N5 C20 C19 114.2(4) . . ?
N5 C20 C21 122.2(4) . . ?
C21 C20 C19 123.6(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(4) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 120.4 . . ?
C21 C22 C23 119.2(4) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 120.9 . . ?
C24 C23 C22 118.2(5) . . ?
C24 C23 H23 120.9 . . ?
N5 C24 C23 122.7(4) . . ?
N5 C24 C25 109.6(4) . . ?
C23 C24 C25 127.4(4) . . ?
O9 C25 N6 122.9(4) . . ?
O9 C25 C24 116.0(4) . . ?
N6 C25 C24 121.0(4) . . ?
N6 C26 H26A 109.5 . . ?
N6 C26 H26B 109.5 . . ?
N6 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N6 C27 H27A 109.5 . . ?
N6 C27 H27B 109.5 . . ?
N6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.126 -0.381 1032.7 208.5 ?

_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 2.580
_oxdiff_exptl_absorpt_empirical_full_min 0.645
####################################################################### 
# 
# 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_202209Am-DMAPA1-3
_database_code_depnum_ccdc_archive 'CCDC 2278529'
loop_
_audit_author_name
_audit_author_address
'Chao Xu'
;Harbin Engineering University
China
;
_audit_update_record             
;
2023-07-02 deposited with the CCDC.	2023-08-28 downloaded from the CCDC.
;
_audit_creation_date             2022-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 N6 O9 Am'
_chemical_formula_sum            'C27 H27 N6 O9 Am'
_chemical_formula_weight         820.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         C1H1N1OAm1
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'
Am Am -9.4100 4.3056 '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                   14.7061(12)
_cell_length_b                   19.4040(10)
_cell_length_c                   12.2732(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.682(9)
_cell_angle_gamma                90
_cell_volume                     3297.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12523
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.8960
_cell_measurement_theta_min      3.4950
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    2.382
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.794
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34461
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.893
_diffrn_reflns_theta_min         3.332
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.794
_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  38.00   0.50    2.00    --    4.33 -99.00-120.00  114
  2  ω     49.00  78.00   0.50    2.00    --    4.33  37.00-180.00   58
  3  ω     43.00  79.00   0.50    2.00    --    4.33  29.00-134.00   72
  4  ω     -7.00  28.00   0.50    2.00    --    4.33  29.00-134.00   70
  5  ω    -42.00  14.00   0.50    2.00    --    4.33 -29.00  64.00  112
  6  ω    -29.00   2.00   0.50    2.00    --   -5.89 -37.00  30.00   62
  7  ω    -20.00  25.00   0.50    2.00    --   -5.89 -99.00  30.00   90
  8  ω    -74.00 -49.00   0.50    2.00    --   -5.89 -37.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0373800000
_diffrn_orient_matrix_UB_12      -0.0116106000
_diffrn_orient_matrix_UB_13      0.0501255000
_diffrn_orient_matrix_UB_21      -0.0289645000
_diffrn_orient_matrix_UB_22      0.0079818000
_diffrn_orient_matrix_UB_23      0.0342566000
_diffrn_orient_matrix_UB_31      -0.0197918000
_diffrn_orient_matrix_UB_32      -0.0336923000
_diffrn_orient_matrix_UB_33      -0.0091679000
_diffrn_oxdiff_digest_frames     
;
01970f8ea99cd45ba3f5b38967cbf6369100628fdea
;
_diffrn_oxdiff_digest_hkl        
;
01b8a74f37555ff2258b8962b6bd4b7537fb71
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5407
_reflns_number_total             8262
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         3.752
_refine_diff_density_min         -2.230
_refine_diff_density_rms         0.199
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         8262
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1314
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C21(H21), C22(H22),
 C23(H23)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C),
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Am1 Am 0.69751(2) 0.57159(2) 0.31453(2) 0.02184(9) Uani 1 1 d . . . . .
O1 O 0.6493(4) 0.4534(2) 0.3273(4) 0.0293(11) Uani 1 1 d . . . . .
O2 O 0.6759(5) 0.3408(3) 0.3452(5) 0.0444(14) Uani 1 1 d . . . . .
O3 O 0.8637(4) 0.6099(3) 0.3418(5) 0.0364(13) Uani 1 1 d . . . . .
O4 O 0.7625(4) 0.5649(2) 0.5273(4) 0.0293(11) Uani 1 1 d . . . . .
O5 O 0.8195(4) 0.6127(3) 0.7017(4) 0.0388(14) Uani 1 1 d . . . . .
O6 O 0.6655(4) 0.6794(2) 0.2013(4) 0.0265(11) Uani 1 1 d . . . . .
O7 O 0.7079(4) 0.5430(3) 0.1261(4) 0.0314(12) Uani 1 1 d . . . . .
O8 O 0.6452(4) 0.5559(3) -0.0672(5) 0.0356(13) Uani 1 1 d . . . . .
O9 O 0.5472(4) 0.5913(3) 0.3623(4) 0.0295(11) Uani 1 1 d . . . . .
N1 N 0.8299(5) 0.4796(3) 0.3409(5) 0.0302(14) Uani 1 1 d . . . . .
N2 N 1.0061(6) 0.6004(5) 0.3234(10) 0.078(3) Uani 1 1 d . . . . .
N3 N 0.7263(4) 0.6869(3) 0.4246(5) 0.0224(12) Uani 1 1 d . . . . .
N4 N 0.6035(4) 0.7865(3) 0.1769(5) 0.0261(12) Uani 1 1 d . . . . .
N5 N 0.5374(4) 0.5689(3) 0.1474(5) 0.0223(11) Uani 1 1 d . . . . .
N6 N 0.3927(5) 0.5604(3) 0.3240(6) 0.0300(14) Uani 1 1 d . . . . .
C1 C 0.7022(6) 0.4005(4) 0.3409(6) 0.0296(16) Uani 1 1 d . . . . .
C2 C 0.8050(6) 0.4136(4) 0.3489(8) 0.0386(19) Uani 1 1 d . . . . .
C3 C 0.8722(7) 0.3615(5) 0.3703(11) 0.065(3) Uani 1 1 d . . . . .
H3 H 0.8542 0.3149 0.3748 0.078 Uiso 1 1 calc R . . . .
C4 C 0.9667(8) 0.3789(5) 0.3850(11) 0.071(3) Uani 1 1 d . . . . .
H4 H 1.0153 0.3443 0.4054 0.085 Uiso 1 1 calc R . . . .
C5 C 0.9914(7) 0.4471(5) 0.3702(10) 0.057(3) Uani 1 1 d . . . . .
H5 H 1.0556 0.4590 0.3763 0.068 Uiso 1 1 calc R . . . .
C6 C 0.9192(6) 0.4966(4) 0.3464(7) 0.0371(18) Uani 1 1 d . . . . .
C7 C 0.9293(6) 0.5723(4) 0.3363(7) 0.0332(17) Uani 1 1 d . . . . .
C8 C 1.0784(11) 0.5612(7) 0.2846(16) 0.109(5) Uani 1 1 d . U . . .
H8A H 1.1358 0.5512 0.3517 0.163 Uiso 1 1 calc GR . . . .
H8B H 1.0969 0.5891 0.2288 0.163 Uiso 1 1 calc GR . . . .
H8C H 1.0495 0.5179 0.2480 0.163 Uiso 1 1 calc GR . . . .
C9 C 1.0154(8) 0.6747(6) 0.3252(13) 0.091(4) Uani 1 1 d . U . . .
H9A H 0.9987 0.6919 0.2458 0.137 Uiso 1 1 calc GR . . . .
H9B H 1.0821 0.6876 0.3695 0.137 Uiso 1 1 calc GR . . . .
H9C H 0.9716 0.6950 0.3615 0.137 Uiso 1 1 calc GR . . . .
C10 C 0.7872(6) 0.6157(4) 0.5953(6) 0.0300(16) Uani 1 1 d . . . . .
C11 C 0.7741(5) 0.6860(4) 0.5382(6) 0.0285(16) Uani 1 1 d . . . . .
C12 C 0.8110(6) 0.7445(4) 0.6011(7) 0.0350(18) Uani 1 1 d . . . . .
H12 H 0.8411 0.7426 0.6827 0.042 Uiso 1 1 calc R . . . .
C13 C 0.8026(6) 0.8065(4) 0.5409(7) 0.0395(19) Uani 1 1 d . . . . .
H13 H 0.8306 0.8474 0.5805 0.047 Uiso 1 1 calc R . . . .
C14 C 0.7530(6) 0.8078(4) 0.4228(7) 0.0360(18) Uani 1 1 d . . . . .
H14 H 0.7464 0.8494 0.3801 0.043 Uiso 1 1 calc R . . . .
C15 C 0.7136(5) 0.7472(4) 0.3690(7) 0.0281(16) Uani 1 1 d . . . . .
C16 C 0.6581(6) 0.7373(4) 0.2419(6) 0.0298(16) Uani 1 1 d . . . . .
C17 C 0.5532(6) 0.7713(4) 0.0534(6) 0.0297(16) Uani 1 1 d . . . . .
H17A H 0.5869 0.7340 0.0288 0.045 Uiso 1 1 calc GR . . . .
H17B H 0.5527 0.8127 0.0073 0.045 Uiso 1 1 calc GR . . . .
H17C H 0.4867 0.7572 0.0420 0.045 Uiso 1 1 calc GR . . . .
C18 C 0.5769(6) 0.8510(4) 0.2178(7) 0.0400(19) Uani 1 1 d . . . . .
H18A H 0.5910 0.8484 0.3016 0.060 Uiso 1 1 calc GR . . . .
H18B H 0.5077 0.8593 0.1793 0.060 Uiso 1 1 calc GR . . . .
H18C H 0.6139 0.8887 0.2001 0.060 Uiso 1 1 calc GR . . . .
C19 C 0.6395(6) 0.5561(3) 0.0325(7) 0.0284(17) Uani 1 1 d . . . . .
C20 C 0.5408(5) 0.5742(3) 0.0423(6) 0.0239(14) Uani 1 1 d . . . . .
C21 C 0.4644(6) 0.5974(4) -0.0511(7) 0.0305(16) Uani 1 1 d . . . . .
H21 H 0.4695 0.5999 -0.1262 0.037 Uiso 1 1 calc R . . . .
C22 C 0.3819(6) 0.6164(4) -0.0327(7) 0.0335(17) Uani 1 1 d . . . . .
H22 H 0.3285 0.6334 -0.0948 0.040 Uiso 1 1 calc R . . . .
C23 C 0.3762(6) 0.6109(4) 0.0772(7) 0.0304(16) Uani 1 1 d . . . . .
H23 H 0.3194 0.6247 0.0917 0.036 Uiso 1 1 calc R . . . .
C24 C 0.4548(6) 0.5849(3) 0.1661(6) 0.0278(16) Uani 1 1 d . . . . .
C25 C 0.4661(5) 0.5788(3) 0.2910(6) 0.0256(15) Uani 1 1 d . . . . .
C26 C 0.2977(6) 0.5382(4) 0.2452(7) 0.0379(19) Uani 1 1 d . . . . .
H26A H 0.2541 0.5779 0.2246 0.057 Uiso 1 1 calc GR . . . .
H26B H 0.2709 0.5033 0.2835 0.057 Uiso 1 1 calc GR . . . .
H26C H 0.3048 0.5186 0.1749 0.057 Uiso 1 1 calc GR . . . .
C27 C 0.4008(6) 0.5632(4) 0.4446(7) 0.0340(17) Uani 1 1 d . . . . .
H27A H 0.4680 0.5726 0.4919 0.051 Uiso 1 1 calc GR . . . .
H27B H 0.3808 0.5189 0.4676 0.051 Uiso 1 1 calc GR . . . .
H27C H 0.3592 0.5999 0.4560 0.051 Uiso 1 1 calc GR . . . .


_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
Am1 O1 2.421(5) . ?
Am1 O3 2.466(5) . ?
Am1 O4 2.463(5) . ?
Am1 O6 2.468(4) . ?
Am1 O7 2.432(5) . ?
Am1 O9 2.499(5) . ?
Am1 N1 2.581(6) . ?
Am1 N3 2.574(5) . ?
Am1 N5 2.550(6) . ?
O1 C1 1.264(9) . ?
O2 C1 1.228(9) . ?
O3 C7 1.229(9) . ?
O4 C10 1.263(9) . ?
O5 C10 1.231(8) . ?
O6 C16 1.249(8) . ?
O7 C19 1.272(10) . ?
O8 C19 1.255(8) . ?
O9 C25 1.243(9) . ?
N1 C2 1.345(10) . ?
N1 C6 1.334(10) . ?
N2 C7 1.311(10) . ?
N2 C8 1.509(15) . ?
N2 C9 1.449(14) . ?
N3 C11 1.333(9) . ?
N3 C15 1.336(9) . ?
N4 C16 1.326(9) . ?
N4 C17 1.476(9) . ?
N4 C18 1.450(9) . ?
N5 C20 1.312(9) . ?
N5 C24 1.347(9) . ?
N6 C25 1.324(9) . ?
N6 C26 1.470(11) . ?
N6 C27 1.445(9) . ?
C1 C2 1.503(11) . ?
C2 C3 1.375(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(12) . ?
C6 C7 1.485(11) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.517(10) . ?
C11 C12 1.376(11) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(11) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(10) . ?
C15 C16 1.510(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.536(10) . ?
C20 C21 1.383(11) . ?
C21 H21 0.9500 . ?
C21 C22 1.358(11) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(10) . ?
C23 H23 0.9500 . ?
C23 C24 1.390(11) . ?
C24 C25 1.489(10) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
O1 Am1 O3 125.07(17) . . ?
O1 Am1 O4 84.20(16) . . ?
O1 Am1 O6 146.63(17) . . ?
O1 Am1 O7 87.66(16) . . ?
O1 Am1 O9 80.11(16) . . ?
O1 Am1 N1 63.98(18) . . ?
O1 Am1 N3 142.13(16) . . ?
O1 Am1 N5 79.72(17) . . ?
O3 Am1 O6 79.25(17) . . ?
O3 Am1 O9 146.74(17) . . ?
O3 Am1 N1 61.33(18) . . ?
O3 Am1 N3 71.75(17) . . ?
O3 Am1 N5 136.02(18) . . ?
O4 Am1 O3 81.90(17) . . ?
O4 Am1 O6 125.02(15) . . ?
O4 Am1 O9 79.48(17) . . ?
O4 Am1 N1 79.85(18) . . ?
O4 Am1 N3 63.44(16) . . ?
O4 Am1 N5 140.82(17) . . ?
O6 Am1 O9 89.23(16) . . ?
O6 Am1 N1 130.55(17) . . ?
O6 Am1 N3 61.64(16) . . ?
O6 Am1 N5 67.35(17) . . ?
O7 Am1 O3 79.69(18) . . ?
O7 Am1 O4 150.42(18) . . ?
O7 Am1 O6 73.68(16) . . ?
O7 Am1 O9 126.97(18) . . ?
O7 Am1 N1 71.04(18) . . ?
O7 Am1 N3 130.18(16) . . ?
O7 Am1 N5 64.35(18) . . ?
O9 Am1 N1 139.97(17) . . ?
O9 Am1 N3 75.31(17) . . ?
O9 Am1 N5 62.73(16) . . ?
N3 Am1 N1 123.51(19) . . ?
N5 Am1 N1 122.68(18) . . ?
N5 Am1 N3 112.59(17) . . ?
C1 O1 Am1 126.6(5) . . ?
C7 O3 Am1 125.0(5) . . ?
C10 O4 Am1 125.6(4) . . ?
C16 O6 Am1 124.3(4) . . ?
C19 O7 Am1 122.0(4) . . ?
C25 O9 Am1 121.4(4) . . ?
C2 N1 Am1 117.1(5) . . ?
C6 N1 Am1 121.5(5) . . ?
C6 N1 C2 121.4(7) . . ?
C7 N2 C8 123.8(10) . . ?
C7 N2 C9 119.5(9) . . ?
C9 N2 C8 115.7(9) . . ?
C11 N3 Am1 118.3(4) . . ?
C11 N3 C15 118.6(6) . . ?
C15 N3 Am1 121.6(4) . . ?
C16 N4 C17 117.8(6) . . ?
C16 N4 C18 126.3(6) . . ?
C18 N4 C17 115.3(6) . . ?
C20 N5 Am1 117.3(5) . . ?
C20 N5 C24 119.0(6) . . ?
C24 N5 Am1 120.0(5) . . ?
C25 N6 C26 124.7(6) . . ?
C25 N6 C27 120.6(7) . . ?
C27 N6 C26 114.7(6) . . ?
O1 C1 C2 115.6(6) . . ?
O2 C1 O1 125.7(7) . . ?
O2 C1 C2 118.7(7) . . ?
N1 C2 C1 116.6(7) . . ?
N1 C2 C3 121.1(8) . . ?
C3 C2 C1 122.1(8) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.3(9) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(9) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.9(9) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C5 120.6(8) . . ?
N1 C6 C7 111.4(7) . . ?
C5 C6 C7 127.7(8) . . ?
O3 C7 N2 119.0(8) . . ?
O3 C7 C6 118.7(7) . . ?
N2 C7 C6 122.3(7) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 C11 115.6(6) . . ?
O5 C10 O4 125.9(7) . . ?
O5 C10 C11 118.4(7) . . ?
N3 C11 C10 115.8(6) . . ?
N3 C11 C12 123.1(7) . . ?
C12 C11 C10 121.1(7) . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.7(7) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(7) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.3(7) . . ?
C15 C14 H14 120.9 . . ?
N3 C15 C14 122.7(7) . . ?
N3 C15 C16 110.5(6) . . ?
C14 C15 C16 126.7(7) . . ?
O6 C16 N4 121.6(7) . . ?
O6 C16 C15 115.9(6) . . ?
N4 C16 C15 122.5(6) . . ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 C20 117.1(6) . . ?
O8 C19 O7 126.0(7) . . ?
O8 C19 C20 116.9(7) . . ?
N5 C20 C19 114.1(6) . . ?
N5 C20 C21 123.4(7) . . ?
C21 C20 C19 122.4(6) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 C20 118.3(7) . . ?
C22 C21 H21 120.9 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.5(8) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.1(7) . . ?
C24 C23 H23 120.5 . . ?
N5 C24 C23 120.6(6) . . ?
N5 C24 C25 111.3(6) . . ?
C23 C24 C25 127.7(6) . . ?
O9 C25 N6 121.7(7) . . ?
O9 C25 C24 117.2(6) . . ?
N6 C25 C24 121.1(7) . . ?
N6 C26 H26A 109.5 . . ?
N6 C26 H26B 109.5 . . ?
N6 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N6 C27 H27A 109.5 . . ?
N6 C27 H27B 109.5 . . ?
N6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.955 -0.173 848.7 132.9 ?

_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 1.707
_oxdiff_exptl_absorpt_empirical_full_min 0.744
