# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_tiy014trans2
_database_code_depnum_ccdc_archive 'CCDC 2248771'
loop_
_audit_author_name
_audit_author_address
'Evgeny Bulatov'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_audit_creation_date             2023-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H44 N4 O2'
_chemical_formula_sum            'C32 H44 N4 O2'
_chemical_formula_weight         516.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4551(8)
_cell_length_b                   10.5908(7)
_cell_length_c                   14.0367(9)
_cell_angle_alpha                97.348(5)
_cell_angle_beta                 110.905(7)
_cell_angle_gamma                92.790(6)
_cell_volume                     1432.54(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1955
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      71.2160
_cell_measurement_theta_min      3.3770
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.587
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -5 0.0200
1 0 5 0.0200
1 5 -5 0.0220
-1 -5 5 0.0220
2 5 2 0.0262
-2 -5 -2 0.0262
-5 1 4 0.0084
5 -1 -4 0.0084

_exptl_crystal_size_max          0.058
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.017
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8838
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.521
_diffrn_reflns_theta_min         3.412
_diffrn_ambient_temperature      120.01
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00   15.00    --  -41.90 125.00-180.00   81
  2  ω    -66.00  32.00   1.00   15.00    --  -41.90  37.00 120.00   98
  3  ω   -108.00 -18.00   1.00   15.00    --  -41.90 -37.00 -60.00   90
  4  ω    103.00 149.00   1.00   30.00    --  103.21  77.00-120.00   46
  5  ω     77.00 157.00   1.00   30.00    --  103.21  45.00 120.00   80
  6  ω     59.00 136.00   1.00   30.00    --  103.21 -77.00  30.00   77
  7  ω     72.00 178.00   1.00   30.00    --  103.21  15.00-150.00  106
  8  ω     75.00 112.00   1.00   30.00    --  103.21-125.00 -60.00   37
  9  ω    113.00 140.00   1.00   30.00    --  103.21 125.00 -30.00   27
 10  ω     39.00 106.00   1.00   30.00    --  103.21 -94.00-180.00   67
 11  ω     36.00 106.00   1.00   30.00    --  103.21 -94.00 -30.00   70
 12  ω     33.00 129.00   1.00   30.00    --  103.21 -45.00 -60.00   96
 13  ω     44.00 126.00   1.00   30.00    --  103.21 -45.00-180.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3763
_reflns_number_total             5395
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      1.046
_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)+(0.0510P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1265
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2B), C3(H3A), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O -0.06936(17) 0.23634(15) -0.08331(11) 0.0250(4) Uani 1 1 d . . . . .
H1A H 0.015(3) 0.260(3) -0.083(2) 0.035(8) Uiso 1 1 d . . . . .
O2 O 0.74513(17) 1.15361(16) 0.58930(12) 0.0279(4) Uani 1 1 d . . . . .
H2A H 0.762(3) 1.069(4) 0.583(3) 0.056(10) Uiso 1 1 d . . . . .
N1 N -0.02410(19) 0.73401(17) 0.26511(14) 0.0194(4) Uani 1 1 d . . . . .
H1 H 0.053(3) 0.764(3) 0.318(2) 0.035(7) Uiso 1 1 d . . . . .
N2 N 0.23111(18) 0.58635(17) 0.24211(14) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.191(3) 0.633(2) 0.1909(19) 0.024(6) Uiso 1 1 d . . . . .
N3 N 0.39694(19) 0.85656(17) 0.24810(14) 0.0206(4) Uani 1 1 d . . . . .
H3 H 0.373(3) 0.850(3) 0.304(2) 0.033(7) Uiso 1 1 d . . . . .
N4 N 0.12329(18) 1.00228(17) 0.23498(14) 0.0197(4) Uani 1 1 d . . . . .
H4 H 0.111(3) 0.939(3) 0.181(2) 0.048(9) Uiso 1 1 d . . . . .
C1 C -0.1148(2) 0.8114(2) 0.20986(16) 0.0202(4) Uani 1 1 d . . . . .
C2 C -0.2111(2) 0.7343(2) 0.12658(16) 0.0232(5) Uani 1 1 d . . . . .
H2B H -0.286430 0.761704 0.074680 0.028 Uiso 1 1 calc R . . . .
C3 C -0.1780(2) 0.6063(2) 0.13178(16) 0.0224(5) Uani 1 1 d . . . . .
H3A H -0.227839 0.532799 0.084223 0.027 Uiso 1 1 calc R . . . .
C4 C -0.0612(2) 0.6074(2) 0.21776(16) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.0143(2) 0.4997(2) 0.26482(16) 0.0199(4) Uani 1 1 d . . . . .
C6 C 0.1688(2) 0.52584(19) 0.29761(16) 0.0186(4) Uani 1 1 d . . . . .
C7 C 0.2708(2) 0.4861(2) 0.37687(16) 0.0220(5) Uani 1 1 d . . . . .
H7 H 0.258376 0.441386 0.427922 0.026 Uiso 1 1 calc R . . . .
C8 C 0.3984(2) 0.5234(2) 0.36940(17) 0.0232(5) Uani 1 1 d . . . . .
H8 H 0.486698 0.507908 0.414379 0.028 Uiso 1 1 calc R . . . .
C9 C 0.3718(2) 0.58615(19) 0.28541(16) 0.0197(4) Uani 1 1 d . . . . .
C10 C 0.4681(2) 0.6315(2) 0.23591(16) 0.0215(5) Uani 1 1 d . . . . .
C11 C 0.4318(2) 0.7550(2) 0.19346(16) 0.0198(4) Uani 1 1 d . . . . .
C12 C 0.4414(2) 0.7962(2) 0.10739(17) 0.0235(5) Uani 1 1 d . . . . .
H12 H 0.463599 0.746548 0.055157 0.028 Uiso 1 1 calc R . . . .
C13 C 0.4126(2) 0.9251(2) 0.10980(17) 0.0237(5) Uani 1 1 d . . . . .
H13 H 0.412682 0.977575 0.059775 0.028 Uiso 1 1 calc R . . . .
C14 C 0.3844(2) 0.9613(2) 0.19704(16) 0.0202(4) Uani 1 1 d . . . . .
C15 C 0.3552(2) 1.0903(2) 0.24021(17) 0.0217(5) Uani 1 1 d . . . . .
C16 C 0.2449(2) 1.07984(19) 0.28580(16) 0.0204(4) Uani 1 1 d . . . . .
C17 C 0.2343(2) 1.1473(2) 0.37271(17) 0.0249(5) Uani 1 1 d . . . . .
H17 H 0.302261 1.208708 0.422696 0.030 Uiso 1 1 calc R . . . .
C18 C 0.1035(2) 1.1083(2) 0.37394(17) 0.0249(5) Uani 1 1 d . . . . .
H18 H 0.068444 1.139081 0.425388 0.030 Uiso 1 1 calc R . . . .
C19 C 0.0359(2) 1.0186(2) 0.28825(17) 0.0219(5) Uani 1 1 d . . . . .
C20 C -0.1087(2) 0.9527(2) 0.24793(18) 0.0241(5) Uani 1 1 d . . . . .
C21 C -0.0211(2) 0.4815(2) 0.36031(17) 0.0261(5) Uani 1 1 d . . . . .
H21A H 0.021109 0.407394 0.389008 0.039 Uiso 1 1 calc GR . . . .
H21B H -0.121215 0.467202 0.340038 0.039 Uiso 1 1 calc GR . . . .
H21C H 0.014331 0.558303 0.412510 0.039 Uiso 1 1 calc GR . . . .
C22 C 0.6169(2) 0.6531(2) 0.31617(18) 0.0272(5) Uani 1 1 d . . . . .
H22A H 0.680117 0.678435 0.283016 0.041 Uiso 1 1 calc GR . . . .
H22B H 0.642108 0.573632 0.343861 0.041 Uiso 1 1 calc GR . . . .
H22C H 0.622679 0.720795 0.372529 0.041 Uiso 1 1 calc GR . . . .
C23 C 0.4630(3) 0.5261(2) 0.14747(19) 0.0289(5) Uani 1 1 d . . . . .
H23A H 0.369391 0.511315 0.095474 0.043 Uiso 1 1 calc GR . . . .
H23B H 0.489024 0.446804 0.175088 0.043 Uiso 1 1 calc GR . . . .
H23C H 0.527141 0.553317 0.115669 0.043 Uiso 1 1 calc GR . . . .
C24 C 0.3048(2) 1.1712(2) 0.15196(18) 0.0281(5) Uani 1 1 d . . . . .
H24A H 0.220417 1.127384 0.098090 0.042 Uiso 1 1 calc GR . . . .
H24B H 0.376059 1.182237 0.122606 0.042 Uiso 1 1 calc GR . . . .
H24C H 0.286185 1.255243 0.179301 0.042 Uiso 1 1 calc GR . . . .
C25 C -0.1682(3) 0.9676(2) 0.3335(2) 0.0388(6) Uani 1 1 d . . . . .
H25A H -0.261578 0.923610 0.307284 0.058 Uiso 1 1 calc GR . . . .
H25B H -0.171168 1.058630 0.355589 0.058 Uiso 1 1 calc GR . . . .
H25C H -0.109966 0.929983 0.392345 0.058 Uiso 1 1 calc GR . . . .
C26 C -0.1994(2) 1.0163(2) 0.1574(2) 0.0338(6) Uani 1 1 d . . . . .
H26A H -0.166142 1.002454 0.100258 0.051 Uiso 1 1 calc GR . . . .
H26B H -0.194638 1.108307 0.180430 0.051 Uiso 1 1 calc GR . . . .
H26C H -0.294946 0.978333 0.134194 0.051 Uiso 1 1 calc GR . . . .
C27 C -0.0360(2) 0.3724(2) 0.18813(16) 0.0218(5) Uani 1 1 d . . . . .
H27A H 0.008746 0.302694 0.224137 0.026 Uiso 1 1 calc R . . . .
H27B H -0.136279 0.354807 0.170577 0.026 Uiso 1 1 calc R . . . .
C28 C -0.0096(2) 0.3663(2) 0.08725(16) 0.0215(5) Uani 1 1 d . . . . .
H28A H -0.051135 0.436869 0.050755 0.026 Uiso 1 1 calc R . . . .
H28B H 0.090738 0.377118 0.102699 0.026 Uiso 1 1 calc R . . . .
C29 C -0.0709(2) 0.2393(2) 0.01879(16) 0.0222(5) Uani 1 1 d . . . . .
H29A H -0.018539 0.170429 0.050759 0.027 Uiso 1 1 calc R . . . .
H29B H -0.167122 0.221992 0.014037 0.027 Uiso 1 1 calc R . . . .
C30 C 0.4892(2) 1.1655(2) 0.32108(17) 0.0236(5) Uani 1 1 d . . . . .
H30A H 0.555487 1.177151 0.286416 0.028 Uiso 1 1 calc R . . . .
H30B H 0.467134 1.251655 0.343030 0.028 Uiso 1 1 calc R . . . .
C31 C 0.5609(2) 1.1067(2) 0.41789(17) 0.0235(5) Uani 1 1 d . . . . .
H31A H 0.495247 1.090069 0.452193 0.028 Uiso 1 1 calc R . . . .
H31B H 0.592343 1.023968 0.398449 0.028 Uiso 1 1 calc R . . . .
C32 C 0.6829(2) 1.1961(2) 0.49160(17) 0.0248(5) Uani 1 1 d . . . . .
H32A H 0.752699 1.204296 0.459556 0.030 Uiso 1 1 calc R . . . .
H32B H 0.652600 1.281968 0.503150 0.030 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 H1A 0.90(3) . ?
O1 C29 1.436(3) . ?
O2 H2A 0.92(4) . ?
O2 C32 1.434(3) . ?
N1 H1 0.89(3) . ?
N1 C1 1.373(3) . ?
N1 C4 1.389(3) . ?
N2 H2 0.91(3) . ?
N2 C6 1.375(3) . ?
N2 C9 1.377(3) . ?
N3 H3 0.91(3) . ?
N3 C11 1.380(3) . ?
N3 C14 1.382(3) . ?
N4 H4 0.92(3) . ?
N4 C16 1.379(3) . ?
N4 C19 1.376(3) . ?
C1 C2 1.372(3) . ?
C1 C20 1.513(3) . ?
C2 H2B 0.9500 . ?
C2 C3 1.420(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.375(3) . ?
C4 C5 1.506(3) . ?
C5 C6 1.513(3) . ?
C5 C21 1.544(3) . ?
C5 C27 1.552(3) . ?
C6 C7 1.367(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.416(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.376(3) . ?
C9 C10 1.505(3) . ?
C10 C11 1.516(3) . ?
C10 C22 1.545(3) . ?
C10 C23 1.543(3) . ?
C11 C12 1.370(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.411(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.372(3) . ?
C14 C15 1.513(3) . ?
C15 C16 1.511(3) . ?
C15 C24 1.548(3) . ?
C15 C30 1.553(3) . ?
C16 C17 1.375(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.416(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.373(3) . ?
C19 C20 1.510(3) . ?
C20 C25 1.533(3) . ?
C20 C26 1.545(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.530(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.514(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.527(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.512(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?

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
C29 O1 H1A 112.5(18) . . ?
C32 O2 H2A 113(2) . . ?
C1 N1 H1 123.1(18) . . ?
C1 N1 C4 110.21(18) . . ?
C4 N1 H1 126.1(18) . . ?
C6 N2 H2 127.2(16) . . ?
C6 N2 C9 110.26(18) . . ?
C9 N2 H2 121.8(16) . . ?
C11 N3 H3 123.6(18) . . ?
C11 N3 C14 109.91(18) . . ?
C14 N3 H3 125.8(18) . . ?
C16 N4 H4 123(2) . . ?
C19 N4 H4 125(2) . . ?
C19 N4 C16 110.40(19) . . ?
N1 C1 C20 122.27(19) . . ?
C2 C1 N1 107.33(19) . . ?
C2 C1 C20 130.1(2) . . ?
C1 C2 H2B 126.1 . . ?
C1 C2 C3 107.83(19) . . ?
C3 C2 H2B 126.1 . . ?
C2 C3 H3A 126.0 . . ?
C4 C3 C2 108.02(19) . . ?
C4 C3 H3A 126.0 . . ?
N1 C4 C5 122.05(18) . . ?
C3 C4 N1 106.60(19) . . ?
C3 C4 C5 131.2(2) . . ?
C4 C5 C6 112.57(17) . . ?
C4 C5 C21 108.10(18) . . ?
C4 C5 C27 110.48(17) . . ?
C6 C5 C21 109.03(17) . . ?
C6 C5 C27 109.41(17) . . ?
C21 C5 C27 107.09(17) . . ?
N2 C6 C5 123.35(18) . . ?
C7 C6 N2 107.19(19) . . ?
C7 C6 C5 129.2(2) . . ?
C6 C7 H7 126.0 . . ?
C6 C7 C8 107.93(19) . . ?
C8 C7 H7 126.0 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.81(19) . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C10 123.14(19) . . ?
C8 C9 N2 106.80(19) . . ?
C8 C9 C10 129.5(2) . . ?
C9 C10 C11 112.59(17) . . ?
C9 C10 C22 109.52(18) . . ?
C9 C10 C23 108.52(18) . . ?
C11 C10 C22 108.58(18) . . ?
C11 C10 C23 109.33(18) . . ?
C23 C10 C22 108.21(18) . . ?
N3 C11 C10 122.12(19) . . ?
C12 C11 N3 107.01(19) . . ?
C12 C11 C10 130.4(2) . . ?
C11 C12 H12 125.9 . . ?
C11 C12 C13 108.1(2) . . ?
C13 C12 H12 125.9 . . ?
C12 C13 H13 126.0 . . ?
C14 C13 C12 108.0(2) . . ?
C14 C13 H13 126.0 . . ?
N3 C14 C15 122.89(19) . . ?
C13 C14 N3 106.94(19) . . ?
C13 C14 C15 130.0(2) . . ?
C14 C15 C24 108.88(18) . . ?
C14 C15 C30 110.64(18) . . ?
C16 C15 C14 112.63(18) . . ?
C16 C15 C24 107.72(18) . . ?
C16 C15 C30 110.63(18) . . ?
C24 C15 C30 106.06(18) . . ?
N4 C16 C15 121.92(19) . . ?
C17 C16 N4 107.1(2) . . ?
C17 C16 C15 130.7(2) . . ?
C16 C17 H17 126.3 . . ?
C16 C17 C18 107.38(19) . . ?
C18 C17 H17 126.3 . . ?
C17 C18 H18 125.8 . . ?
C19 C18 C17 108.5(2) . . ?
C19 C18 H18 125.8 . . ?
N4 C19 C20 122.54(19) . . ?
C18 C19 N4 106.6(2) . . ?
C18 C19 C20 130.7(2) . . ?
C1 C20 C25 108.45(19) . . ?
C1 C20 C26 108.51(19) . . ?
C19 C20 C1 112.46(18) . . ?
C19 C20 C25 109.8(2) . . ?
C19 C20 C26 108.97(18) . . ?
C25 C20 C26 108.6(2) . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C5 C27 H27A 108.1 . . ?
C5 C27 H27B 108.1 . . ?
H27A C27 H27B 107.3 . . ?
C28 C27 C5 116.80(18) . . ?
C28 C27 H27A 108.1 . . ?
C28 C27 H27B 108.1 . . ?
C27 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C29 C28 C27 110.36(18) . . ?
C29 C28 H28A 109.6 . . ?
C29 C28 H28B 109.6 . . ?
O1 C29 C28 112.61(18) . . ?
O1 C29 H29A 109.1 . . ?
O1 C29 H29B 109.1 . . ?
C28 C29 H29A 109.1 . . ?
C28 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
C15 C30 H30A 108.0 . . ?
C15 C30 H30B 108.0 . . ?
H30A C30 H30B 107.3 . . ?
C31 C30 C15 117.08(18) . . ?
C31 C30 H30A 108.0 . . ?
C31 C30 H30B 108.0 . . ?
C30 C31 H31A 109.6 . . ?
C30 C31 H31B 109.6 . . ?
H31A C31 H31B 108.1 . . ?
C32 C31 C30 110.24(18) . . ?
C32 C31 H31A 109.6 . . ?
C32 C31 H31B 109.6 . . ?
O2 C32 C31 113.05(19) . . ?
O2 C32 H32A 109.0 . . ?
O2 C32 H32B 109.0 . . ?
C31 C32 H32A 109.0 . . ?
C31 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?

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
N1 H1 O2 0.89(3) 2.11(3) 2.981(3) 165(3) 2_676 yes
N2 H2 O1 0.91(3) 2.27(3) 3.169(2) 169(2) 2_565 yes
N3 H3 O2 0.91(3) 2.26(3) 3.145(3) 164(2) 2_676 yes
N4 H4 O1 0.92(3) 2.08(3) 2.977(2) 164(3) 2_565 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
N1 C1 C2 C3 0.2(2) . . . . ?
N1 C1 C20 C19 45.7(3) . . . . ?
N1 C1 C20 C25 -75.9(3) . . . . ?
N1 C1 C20 C26 166.3(2) . . . . ?
N1 C4 C5 C6 -49.4(3) . . . . ?
N1 C4 C5 C21 71.1(3) . . . . ?
N1 C4 C5 C27 -172.00(18) . . . . ?
N2 C6 C7 C8 0.0(2) . . . . ?
N2 C9 C10 C11 43.9(3) . . . . ?
N2 C9 C10 C22 164.78(19) . . . . ?
N2 C9 C10 C23 -77.3(2) . . . . ?
N3 C11 C12 C13 0.3(2) . . . . ?
N3 C14 C15 C16 -43.7(3) . . . . ?
N3 C14 C15 C24 -163.09(19) . . . . ?
N3 C14 C15 C30 80.7(2) . . . . ?
N4 C16 C17 C18 0.3(2) . . . . ?
N4 C19 C20 C1 47.5(3) . . . . ?
N4 C19 C20 C25 168.3(2) . . . . ?
N4 C19 C20 C26 -72.9(3) . . . . ?
C1 N1 C4 C3 -0.5(2) . . . . ?
C1 N1 C4 C5 -175.94(19) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C1 C20 C19 -141.9(2) . . . . ?
C2 C1 C20 C25 96.6(3) . . . . ?
C2 C1 C20 C26 -21.3(3) . . . . ?
C2 C3 C4 N1 0.6(2) . . . . ?
C2 C3 C4 C5 175.5(2) . . . . ?
C3 C4 C5 C6 136.4(2) . . . . ?
C3 C4 C5 C21 -103.1(3) . . . . ?
C3 C4 C5 C27 13.8(3) . . . . ?
C4 N1 C1 C2 0.2(2) . . . . ?
C4 N1 C1 C20 174.09(19) . . . . ?
C4 C5 C6 N2 -38.0(3) . . . . ?
C4 C5 C6 C7 149.2(2) . . . . ?
C4 C5 C27 C28 63.6(2) . . . . ?
C5 C6 C7 C8 173.7(2) . . . . ?
C5 C27 C28 C29 -177.04(18) . . . . ?
C6 N2 C9 C8 0.4(2) . . . . ?
C6 N2 C9 C10 172.76(18) . . . . ?
C6 C5 C27 C28 -60.9(2) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 N2 -0.4(2) . . . . ?
C7 C8 C9 C10 -172.1(2) . . . . ?
C8 C9 C10 C11 -145.7(2) . . . . ?
C8 C9 C10 C22 -24.8(3) . . . . ?
C8 C9 C10 C23 93.2(3) . . . . ?
C9 N2 C6 C5 -174.46(18) . . . . ?
C9 N2 C6 C7 -0.3(2) . . . . ?
C9 C10 C11 N3 44.0(3) . . . . ?
C9 C10 C11 C12 -144.8(2) . . . . ?
C10 C11 C12 C13 -172.0(2) . . . . ?
C11 N3 C14 C13 -0.4(2) . . . . ?
C11 N3 C14 C15 -176.33(19) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C12 C13 C14 N3 0.5(2) . . . . ?
C12 C13 C14 C15 176.1(2) . . . . ?
C13 C14 C15 C16 141.4(2) . . . . ?
C13 C14 C15 C24 22.0(3) . . . . ?
C13 C14 C15 C30 -94.2(3) . . . . ?
C14 N3 C11 C10 173.09(19) . . . . ?
C14 N3 C11 C12 0.1(2) . . . . ?
C14 C15 C16 N4 -46.1(3) . . . . ?
C14 C15 C16 C17 141.1(2) . . . . ?
C14 C15 C30 C31 -62.5(3) . . . . ?
C15 C16 C17 C18 173.9(2) . . . . ?
C15 C30 C31 C32 -175.84(19) . . . . ?
C16 N4 C19 C18 0.2(2) . . . . ?
C16 N4 C19 C20 175.96(19) . . . . ?
C16 C15 C30 C31 63.1(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 N4 0.0(2) . . . . ?
C17 C18 C19 C20 -175.3(2) . . . . ?
C18 C19 C20 C1 -137.9(2) . . . . ?
C18 C19 C20 C25 -17.1(3) . . . . ?
C18 C19 C20 C26 101.8(3) . . . . ?
C19 N4 C16 C15 -174.62(18) . . . . ?
C19 N4 C16 C17 -0.3(2) . . . . ?
C20 C1 C2 C3 -173.1(2) . . . . ?
C21 C5 C6 N2 -157.95(19) . . . . ?
C21 C5 C6 C7 29.2(3) . . . . ?
C21 C5 C27 C28 -178.92(18) . . . . ?
C22 C10 C11 N3 -77.5(2) . . . . ?
C22 C10 C11 C12 93.7(3) . . . . ?
C23 C10 C11 N3 164.66(19) . . . . ?
C23 C10 C11 C12 -24.1(3) . . . . ?
C24 C15 C16 N4 74.0(2) . . . . ?
C24 C15 C16 C17 -98.8(3) . . . . ?
C24 C15 C30 C31 179.62(19) . . . . ?
C27 C5 C6 N2 85.2(2) . . . . ?
C27 C5 C6 C7 -87.6(3) . . . . ?
C27 C28 C29 O1 170.33(17) . . . . ?
C30 C15 C16 N4 -170.51(18) . . . . ?
C30 C15 C16 C17 16.7(3) . . . . ?
C30 C31 C32 O2 173.03(18) . . . . ?

# start Validation Reply Form
_vrf_PLAT420_GLOBAL              
;
PROBLEM: D-H Bond Without Acceptor  O2--H2A . Please Check
RESPONSE: There is no hydrogen bond acceptor atom in the
proximity to O2. Location of H2A is supported by the density difference map.  
;
# end Validation Reply Form

_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
;
####################################################################### 
# 
# 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_mo_UPME5S1S2_0m
_database_code_depnum_ccdc_archive 'CCDC 2248774'
loop_
_audit_author_name
_audit_author_address
'Evgeny Bulatov'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H50 N6 O4'
_chemical_formula_weight         774.94

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.5102(9)
_cell_length_b                   12.6105(6)
_cell_length_c                   20.3179(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.4282(19)
_cell_angle_gamma                90
_cell_volume                     4131.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2256
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      29.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7091
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            13641
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         29.140
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5358
_reflns_number_gt                3388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker APEX2 v2014.9-0'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.8502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5358
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1311
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17008(8) 0.52954(11) 0.00853(6) 0.0317(3) Uani 1 1 d . . . . .
O2 O 0.43199(7) 0.39289(10) 0.06469(6) 0.0282(3) Uani 1 1 d . . . . .
N1 N 0.42641(8) 0.88742(11) -0.20524(7) 0.0195(3) Uani 1 1 d . . . . .
H1 H 0.399345 0.867357 -0.245458 0.025(5) Uiso 1 1 calc R . . . .
N2 N 0.43710(8) 0.61553(10) -0.19147(7) 0.0174(3) Uani 1 1 d . . . . .
H2 H 0.483324 0.627950 -0.161686 0.021 Uiso 1 1 calc R U . . .
N3 N 0.30861(9) 0.48363(11) 0.03080(7) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.48337(10) 0.96894(13) -0.19311(9) 0.0206(4) Uani 1 1 d . . . . .
C2 C 0.51097(11) 0.97571(14) -0.12470(9) 0.0257(4) Uani 1 1 d . . . . .
H2A H 0.550485 1.024958 -0.101398 0.031 Uiso 1 1 calc R U . . .
C3 C 0.46975(11) 0.89555(14) -0.09468(9) 0.0258(4) Uani 1 1 d . . . . .
H3 H 0.476995 0.881894 -0.047787 0.031 Uiso 1 1 calc R U . . .
C4 C 0.41788(10) 0.84178(13) -0.14542(8) 0.0192(4) Uani 1 1 d . . . . .
C5 C 0.35584(10) 0.75388(13) -0.14410(8) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.37293(10) 0.70906(13) -0.07160(8) 0.0199(4) Uani 1 1 d . . . . .
H6A H 0.433133 0.695011 -0.057095 0.024 Uiso 1 1 calc R U . . .
H6AB H 0.358629 0.764288 -0.041380 0.024 Uiso 1 1 calc R U . . .
C7 C 0.32612(11) 0.60756(13) -0.06196(8) 0.0220(4) Uani 1 1 d . . . . .
H7A H 0.265920 0.617229 -0.079971 0.026 Uiso 1 1 calc R U . . .
H7AB H 0.345566 0.547963 -0.086262 0.026 Uiso 1 1 calc R U . . .
C8 C 0.34261(12) 0.58406(14) 0.01284(9) 0.0259(4) Uani 1 1 d . . . . .
H8A H 0.403332 0.583687 0.030672 0.031 Uiso 1 1 calc R U . . .
H8AB H 0.319098 0.642374 0.035491 0.031 Uiso 1 1 calc R U . . .
C9 C 0.35710(11) 0.39754(14) 0.05771(8) 0.0224(4) Uani 1 1 d . . . . .
C10 C 0.29952(11) 0.31771(14) 0.07594(8) 0.0231(4) Uani 1 1 d . . . . .
C11 C 0.31641(13) 0.21924(14) 0.10524(9) 0.0291(4) Uani 1 1 d . . . . .
H11 H 0.371024 0.190978 0.115332 0.035 Uiso 1 1 calc R U . . .
C12 C 0.24954(14) 0.16351(16) 0.11924(9) 0.0361(5) Uani 1 1 d . . . . .
H12 H 0.258554 0.095502 0.139617 0.043 Uiso 1 1 calc R U . . .
C13 C 0.16964(14) 0.20513(17) 0.10405(10) 0.0387(5) Uani 1 1 d . . . . .
H13 H 0.125311 0.164744 0.114185 0.046 Uiso 1 1 calc R U . . .
C14 C 0.15305(12) 0.30454(17) 0.07436(10) 0.0342(5) Uani 1 1 d . . . . .
H14 H 0.098553 0.333170 0.064155 0.041 Uiso 1 1 calc R U . . .
C15 C 0.22032(11) 0.35976(14) 0.06039(8) 0.0246(4) Uani 1 1 d . . . . .
C16 C 0.22442(11) 0.46685(14) 0.02982(8) 0.0234(4) Uani 1 1 d . . . . .
C17 C 0.26751(10) 0.80093(14) -0.16228(9) 0.0216(4) Uani 1 1 d . . . . .
H17A H 0.226878 0.745052 -0.160222 0.032 Uiso 1 1 calc R U . . .
H17B H 0.257305 0.830389 -0.207962 0.032 Uiso 1 1 calc R U . . .
H17C H 0.262265 0.857235 -0.130213 0.032 Uiso 1 1 calc R U . . .
C18 C 0.36361(10) 0.66849(13) -0.19459(8) 0.0170(3) Uani 1 1 d . . . . .
C19 C 0.30712(10) 0.62680(13) -0.24756(8) 0.0204(4) Uani 1 1 d . . . . .
H19 H 0.250873 0.648031 -0.261918 0.025 Uiso 1 1 calc R U . . .
C20 C 0.34771(10) 0.54579(13) -0.27738(8) 0.0211(4) Uani 1 1 d . . . . .
H20 H 0.323420 0.503427 -0.315149 0.025 Uiso 1 1 calc R U . . .
C21 C 0.42803(10) 0.54014(13) -0.24172(8) 0.0173(3) Uani 1 1 d . . . . .
C22 C 0.500000 0.47055(18) -0.250000 0.0185(5) Uani 1 2 d S T P . .
C23 C 0.47339(11) 0.39975(13) -0.31238(9) 0.0239(4) Uani 1 1 d . . . . .
H23A H 0.518549 0.350881 -0.315547 0.036 Uiso 1 1 calc R U . . .
H23B H 0.460595 0.444106 -0.352903 0.036 Uiso 1 1 calc R U . . .
H23C H 0.424052 0.359079 -0.308520 0.036 Uiso 1 1 calc R U . . .
C24 C 0.42405(11) 1.10765(14) -0.27647(10) 0.0283(4) Uani 1 1 d . . . . .
H24A H 0.434826 1.152590 -0.313001 0.042 Uiso 1 1 calc R U . . .
H24B H 0.413527 1.152449 -0.239796 0.042 Uiso 1 1 calc R U . . .
H24C H 0.375448 1.063039 -0.293479 0.042 Uiso 1 1 calc R U . . .
C25 C 0.500000 1.03676(18) -0.250000 0.0214(5) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C16 1.204(2) . ?
O2 C9 1.215(2) . ?
N1 C4 1.379(2) . ?
N1 C1 1.379(2) . ?
N2 C18 1.374(2) . ?
N2 C21 1.379(2) . ?
N3 C9 1.389(2) . ?
N3 C16 1.402(2) . ?
N3 C8 1.463(2) . ?
C1 C2 1.369(2) . ?
C1 C25 1.510(2) . ?
C2 C3 1.427(2) . ?
C3 C4 1.370(2) . ?
C4 C5 1.514(2) . ?
C5 C18 1.512(2) . ?
C5 C17 1.544(2) . ?
C5 C6 1.546(2) . ?
C6 C7 1.529(2) . ?
C7 C8 1.514(2) . ?
C9 C10 1.485(2) . ?
C10 C11 1.379(3) . ?
C10 C15 1.383(2) . ?
C11 C12 1.389(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.393(3) . ?
C14 C15 1.391(2) . ?
C15 C16 1.494(3) . ?
C18 C19 1.369(2) . ?
C19 C20 1.426(2) . ?
C20 C21 1.369(2) . ?
C21 C22 1.515(2) . ?
C22 C23 1.535(2) 2_654 ?
C22 C23 1.535(2) . ?
C24 C25 1.540(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
C4 N1 C1 110.41(14) . . ?
C18 N2 C21 110.29(14) . . ?
C9 N3 C16 111.92(14) . . ?
C9 N3 C8 123.72(15) . . ?
C16 N3 C8 124.02(15) . . ?
C2 C1 N1 107.04(14) . . ?
C2 C1 C25 131.78(15) . . ?
N1 C1 C25 120.99(15) . . ?
C1 C2 C3 107.74(15) . . ?
C4 C3 C2 107.90(15) . . ?
C3 C4 N1 106.91(14) . . ?
C3 C4 C5 131.69(15) . . ?
N1 C4 C5 121.28(15) . . ?
C18 C5 C4 110.67(12) . . ?
C18 C5 C17 108.98(13) . . ?
C4 C5 C17 108.80(13) . . ?
C18 C5 C6 111.19(13) . . ?
C4 C5 C6 107.41(13) . . ?
C17 C5 C6 109.75(12) . . ?
C7 C6 C5 115.74(14) . . ?
C8 C7 C6 107.80(14) . . ?
N3 C8 C7 115.08(15) . . ?
O2 C9 N3 124.70(16) . . ?
O2 C9 C10 128.91(16) . . ?
N3 C9 C10 106.39(14) . . ?
C11 C10 C15 122.49(16) . . ?
C11 C10 C9 129.56(17) . . ?
C15 C10 C9 107.92(15) . . ?
C10 C11 C12 116.63(19) . . ?
C11 C12 C13 121.41(19) . . ?
C14 C13 C12 121.64(17) . . ?
C15 C14 C13 116.60(19) . . ?
C10 C15 C14 121.24(18) . . ?
C10 C15 C16 108.44(14) . . ?
C14 C15 C16 130.31(18) . . ?
O1 C16 N3 124.45(17) . . ?
O1 C16 C15 130.23(16) . . ?
N3 C16 C15 105.31(14) . . ?
C19 C18 N2 107.16(14) . . ?
C19 C18 C5 131.63(15) . . ?
N2 C18 C5 121.20(14) . . ?
C18 C19 C20 107.83(15) . . ?
C21 C20 C19 107.61(15) . . ?
C20 C21 N2 107.11(14) . . ?
C20 C21 C22 131.65(14) . . ?
N2 C21 C22 121.24(13) . . ?
C21 C22 C21 109.23(18) 2_654 . ?
C21 C22 C23 109.67(9) 2_654 2_654 ?
C21 C22 C23 109.69(8) . 2_654 ?
C21 C22 C23 109.69(8) 2_654 . ?
C21 C22 C23 109.67(9) . . ?
C23 C22 C23 108.88(19) 2_654 . ?
C1 C25 C1 111.00(18) . 2_654 ?
C1 C25 C24 109.27(10) . 2_654 ?
C1 C25 C24 109.13(9) 2_654 2_654 ?
C1 C25 C24 109.13(9) . . ?
C1 C25 C24 109.27(10) 2_654 . ?
C24 C25 C24 109.0(2) 2_654 . ?

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
C4 N1 C1 C2 -0.42(18) . . . . ?
C4 N1 C1 C25 -175.95(13) . . . . ?
N1 C1 C2 C3 0.29(19) . . . . ?
C25 C1 C2 C3 175.15(15) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 N1 -0.19(19) . . . . ?
C2 C3 C4 C5 -176.12(16) . . . . ?
C1 N1 C4 C3 0.38(18) . . . . ?
C1 N1 C4 C5 176.83(13) . . . . ?
C3 C4 C5 C18 -135.47(18) . . . . ?
N1 C4 C5 C18 49.08(19) . . . . ?
C3 C4 C5 C17 104.8(2) . . . . ?
N1 C4 C5 C17 -70.63(18) . . . . ?
C3 C4 C5 C6 -13.9(2) . . . . ?
N1 C4 C5 C6 170.63(14) . . . . ?
C18 C5 C6 C7 -49.35(18) . . . . ?
C4 C5 C6 C7 -170.57(13) . . . . ?
C17 C5 C6 C7 71.30(17) . . . . ?
C5 C6 C7 C8 -173.14(14) . . . . ?
C9 N3 C8 C7 111.53(19) . . . . ?
C16 N3 C8 C7 -75.7(2) . . . . ?
C6 C7 C8 N3 -174.53(14) . . . . ?
C16 N3 C9 O2 -179.23(16) . . . . ?
C8 N3 C9 O2 -5.7(3) . . . . ?
C16 N3 C9 C10 -0.07(18) . . . . ?
C8 N3 C9 C10 173.48(14) . . . . ?
O2 C9 C10 C11 0.1(3) . . . . ?
N3 C9 C10 C11 -178.96(17) . . . . ?
O2 C9 C10 C15 178.12(17) . . . . ?
N3 C9 C10 C15 -0.99(18) . . . . ?
C15 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 177.18(16) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C9 C10 C15 C14 -177.48(16) . . . . ?
C11 C10 C15 C16 179.75(15) . . . . ?
C9 C10 C15 C16 1.60(18) . . . . ?
C13 C14 C15 C10 -0.5(3) . . . . ?
C13 C14 C15 C16 -179.37(17) . . . . ?
C9 N3 C16 O1 -179.54(16) . . . . ?
C8 N3 C16 O1 6.9(3) . . . . ?
C9 N3 C16 C15 1.01(18) . . . . ?
C8 N3 C16 C15 -172.51(14) . . . . ?
C10 C15 C16 O1 178.97(17) . . . . ?
C14 C15 C16 O1 -2.1(3) . . . . ?
C10 C15 C16 N3 -1.62(18) . . . . ?
C14 C15 C16 N3 177.34(17) . . . . ?
C21 N2 C18 C19 -0.27(17) . . . . ?
C21 N2 C18 C5 178.59(13) . . . . ?
C4 C5 C18 C19 -123.13(18) . . . . ?
C17 C5 C18 C19 -3.5(2) . . . . ?
C6 C5 C18 C19 117.57(19) . . . . ?
C4 C5 C18 N2 58.32(19) . . . . ?
C17 C5 C18 N2 177.93(13) . . . . ?
C6 C5 C18 N2 -60.97(18) . . . . ?
N2 C18 C19 C20 0.13(17) . . . . ?
C5 C18 C19 C20 -178.56(15) . . . . ?
C18 C19 C20 C21 0.04(18) . . . . ?
C19 C20 C21 N2 -0.20(17) . . . . ?
C19 C20 C21 C22 -179.48(15) . . . . ?
C18 N2 C21 C20 0.29(17) . . . . ?
C18 N2 C21 C22 179.66(13) . . . . ?
C20 C21 C22 C21 123.11(19) . . . 2_654 ?
N2 C21 C22 C21 -56.08(11) . . . 2_654 ?
C20 C21 C22 C23 -116.66(17) . . . 2_654 ?
N2 C21 C22 C23 64.14(19) . . . 2_654 ?
C20 C21 C22 C23 2.9(2) . . . . ?
N2 C21 C22 C23 -176.32(13) . . . . ?
C2 C1 C25 C1 135.7(2) . . . 2_654 ?
N1 C1 C25 C1 -50.03(11) . . . 2_654 ?
C2 C1 C25 C24 15.3(2) . . . 2_654 ?
N1 C1 C25 C24 -170.43(14) . . . 2_654 ?
C2 C1 C25 C24 -103.82(19) . . . . ?
N1 C1 C25 C24 70.45(19) . . . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_tiy-015-cis-6_a
_database_code_depnum_ccdc_archive 'CCDC 2248772'
loop_
_audit_author_name
_audit_author_address
'Evgeny Bulatov'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_audit_creation_date             2023-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(Cl), 2(C32 H44 N4 O2), 0.5(C4 H12 O2), 2(C4 H12 N)'
_chemical_formula_sum            'C74 H118 Cl2 N10 O5'
_chemical_formula_weight         1298.68
_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'
Cl Cl 0.3639 0.7018 '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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.0787(9)
_cell_length_b                   18.1527(5)
_cell_length_c                   22.8772(12)
_cell_angle_alpha                90
_cell_angle_beta                 108.690(5)
_cell_angle_gamma                90
_cell_volume                     7111.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8894
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.4350
_cell_measurement_theta_min      3.1580
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    1.263
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2824
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 5 0.0520
1 5 -2 0.0542
0 -5 1 0.0477
1 0 -5 0.0390
0 5 -1 0.0510
5 0 -1 0.0473
-1 -5 -1 0.0531
1 5 1 0.0531
-11 0 2 0.0581

_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.091
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18056
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.581
_diffrn_reflns_theta_min         3.176
_diffrn_ambient_temperature      120.01
_diffrn_detector_area_resol_mean 5.1947
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -24.00   1.00    6.00    --  -41.92 -37.00-150.00   86
  2  ω   -114.00 -19.00   1.00    6.00    --  -41.92 -37.00 120.00   95
  3  ω    -86.00 -54.00   1.00    6.00    --  -41.92 125.00  30.00   32
  4  ω     55.00  82.00   1.00    6.00    --   41.92-122.00 137.00   27
  5  ω     36.00 109.00   1.00   30.00    --  112.00-111.00-180.00   73
  6  ω     59.00 109.00   1.00   30.00    --  112.00-111.00-150.00   50
  7  ω     87.00 139.00   1.00   30.00    --  112.00 178.00 -30.00   52
  8  ω     60.00 177.00   1.00   30.00    --  112.00  15.00 -30.00  117
  9  ω    103.00 177.00   1.00   30.00    --  112.00  30.00  30.00   74
 10  ω     83.00 109.00   1.00   30.00    --  112.00-111.00 120.00   26
 11  ω     52.00  91.00   1.00   30.00    --  112.00 -45.00 -60.00   39
 12  ω    111.00 138.00   1.00   30.00    --  112.00 -45.00 -60.00   27
 13  ω     83.00 134.00   1.00   30.00    --  112.00 178.00-150.00   51
 14  ω     36.00  76.00   1.00   30.00    --  112.00-111.00-120.00   40
 15  ω     41.00  94.00   1.00   30.00    --  112.00 -61.00-120.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6502
_reflns_number_total             7343
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.901
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.00015(3)
_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   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         7343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0954
_refine_ls_restrained_S_all      1.144
_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)+(0.0617P)²+42.9873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2272
_refine_ls_wR_factor_ref         0.2306
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C26A) = Uanis(C26)
3. Others
 Fixed Sof: H1B(0.5) H1A(0.5) H2B(0.5) H2A(0.5) H25A(0.5) H25B(0.5) H25C(0.5)
 H25D(0.5) C26(0.5) H26A(0.5) H26B(0.5) C26A(0.5) H26C(0.5) H26D(0.5) H1S(0.5)
 C1S(0.5) H1SA(0.5) H1SB(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5) H2SC(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C25(H25C,H25D), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B), C26(H26A,H26B), C26A(H26C,H26D), C1S(H1SA,H1SB)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2C), C3(H3A), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17), C18(H18)
4.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C2S(H2SA,H2SB,H2SC), C1A(H1AA,
 H1AB,H1AC), C2A(H2AA,H2AB,H2AC), C3A(H3AA,H3AB,H3AC), C4A(H4AA,H4AB,H4AC)
4.d Idealised tetrahedral OH refined with everything fixed:
 O1(H1A)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1B), O2(H2B), O2(H2A), O1S(H1S)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.35924(5) 0.35806(5) 0.75374(4) 0.0322(2) Uani 1 1 d . . . . .
O1 O 0.3873(2) 0.2804(3) 0.89480(18) 0.0659(11) Uani 1 1 d . . . . .
H1B H 0.395579 0.301121 0.864632 0.099 Uiso 0.5 1 calc GR . . A 2
H1A H 0.374528 0.239712 0.906147 0.099 Uiso 0.5 1 calc . . . B 1
O2 O 0.2045(2) 0.33763(19) 0.59070(15) 0.0502(8) Uani 1 1 d . . . . .
H2B H 0.176069 0.310267 0.604090 0.075 Uiso 0.5 1 calc GR . . C 4
H2A H 0.217308 0.312473 0.564658 0.075 Uiso 0.5 1 calc GR . . D 3
N1 N 0.49597(19) 0.44833(17) 0.86276(14) 0.0283(7) Uani 1 1 d . . . . .
H1 H 0.465(3) 0.428(3) 0.836(2) 0.035(12) Uiso 1 1 d . . . . .
N2 N 0.54309(18) 0.35739(17) 0.75238(14) 0.0278(6) Uani 1 1 d . . . . .
H2 H 0.493(3) 0.359(2) 0.751(2) 0.033(12) Uiso 1 1 d . . . . .
N3 N 0.40809(18) 0.45353(17) 0.64462(14) 0.0279(6) Uani 1 1 d . . . . .
H3 H 0.395(3) 0.424(3) 0.670(2) 0.046(14) Uiso 1 1 d . . . . .
N4 N 0.35796(18) 0.54077(17) 0.75626(14) 0.0270(6) Uani 1 1 d . . . . .
H4 H 0.357(3) 0.490(3) 0.753(2) 0.035(12) Uiso 1 1 d . . . . .
C1 C 0.4841(2) 0.5140(2) 0.88885(17) 0.0303(8) Uani 1 1 d . . . . .
C2 C 0.5551(3) 0.5339(3) 0.9293(2) 0.0483(12) Uani 1 1 d . . . . .
H2C H 0.565836 0.577261 0.953787 0.058 Uiso 1 1 calc R . . . .
C3 C 0.6099(3) 0.4783(3) 0.9281(2) 0.0517(13) Uani 1 1 d . . . . .
H3A H 0.663700 0.478053 0.951952 0.062 Uiso 1 1 calc R . . . .
C4 C 0.5721(2) 0.4251(2) 0.88667(17) 0.0319(8) Uani 1 1 d . . . . .
C5 C 0.6007(2) 0.3527(2) 0.86970(17) 0.0307(8) Uani 1 1 d . . . . .
C6 C 0.6076(2) 0.35537(19) 0.80530(17) 0.0290(8) Uani 1 1 d . . . . .
C7 C 0.6718(2) 0.3558(2) 0.78607(19) 0.0343(9) Uani 1 1 d . . . . .
H7 H 0.724634 0.354835 0.812152 0.041 Uiso 1 1 calc R . . . .
C8 C 0.6464(2) 0.3578(2) 0.72068(19) 0.0331(8) Uani 1 1 d . . . . .
H8 H 0.679034 0.358538 0.695366 0.040 Uiso 1 1 calc R . . . .
C9 C 0.5663(2) 0.35843(19) 0.70044(17) 0.0279(7) Uani 1 1 d . . . . .
C10 C 0.5087(2) 0.3607(2) 0.63574(17) 0.0286(7) Uani 1 1 d . . . . .
C11 C 0.4679(2) 0.4348(2) 0.62232(16) 0.0270(7) Uani 1 1 d . . . . .
C12 C 0.4781(2) 0.4936(2) 0.58754(18) 0.0314(8) Uani 1 1 d . . . . .
H12 H 0.515630 0.496711 0.566533 0.038 Uiso 1 1 calc R . . . .
C13 C 0.4229(2) 0.5484(2) 0.58862(18) 0.0321(8) Uani 1 1 d . . . . .
H13 H 0.416739 0.594864 0.568473 0.038 Uiso 1 1 calc R . . . .
C14 C 0.3794(2) 0.5224(2) 0.62416(16) 0.0278(7) Uani 1 1 d . . . . .
C15 C 0.3116(2) 0.5563(2) 0.63951(17) 0.0295(8) Uani 1 1 d . . . . .
C16 C 0.3375(2) 0.5860(2) 0.70512(17) 0.0282(7) Uani 1 1 d . . . . .
C17 C 0.3471(2) 0.6576(2) 0.72588(19) 0.0324(8) Uani 1 1 d . . . . .
H17 H 0.337651 0.700584 0.700931 0.039 Uiso 1 1 calc R . . . .
C18 C 0.3736(2) 0.6555(2) 0.79134(19) 0.0341(8) Uani 1 1 d . . . . .
H18 H 0.384865 0.697060 0.817965 0.041 Uiso 1 1 calc R . . . .
C19 C 0.3800(2) 0.5835(2) 0.80947(17) 0.0285(8) Uani 1 1 d . . . . .
C20 C 0.4049(2) 0.5503(2) 0.87338(17) 0.0299(8) Uani 1 1 d . . . . .
C21 C 0.4101(2) 0.6116(2) 0.92043(18) 0.0378(9) Uani 1 1 d . . . . .
H21A H 0.450366 0.647083 0.919034 0.057 Uiso 1 1 calc GR . . . .
H21B H 0.423567 0.590340 0.961885 0.057 Uiso 1 1 calc GR . . . .
H21C H 0.359578 0.636806 0.910473 0.057 Uiso 1 1 calc GR . . . .
C22 C 0.3442(2) 0.4931(2) 0.87922(18) 0.0354(9) Uani 1 1 d . . . . .
H22A H 0.292722 0.516496 0.868780 0.053 Uiso 1 1 calc GR . . . .
H22B H 0.359439 0.474642 0.921678 0.053 Uiso 1 1 calc GR . . . .
H22C H 0.341955 0.452052 0.850911 0.053 Uiso 1 1 calc GR . . . .
C23 C 0.6825(2) 0.3375(2) 0.9156(2) 0.0384(10) Uani 1 1 d . . . . .
H23A H 0.702789 0.291350 0.904508 0.058 Uiso 1 1 calc GR . . . .
H23B H 0.679185 0.333379 0.957430 0.058 Uiso 1 1 calc GR . . . .
H23C H 0.717661 0.378065 0.914196 0.058 Uiso 1 1 calc GR . . . .
C24 C 0.5447(2) 0.2885(2) 0.87260(17) 0.0325(8) Uani 1 1 d . . . . .
H24A H 0.493862 0.297130 0.840296 0.039 Uiso 1 1 calc R . . . .
H24B H 0.566391 0.242221 0.861891 0.039 Uiso 1 1 calc R . . . .
C25 C 0.5294(3) 0.2766(4) 0.9338(2) 0.0581(14) Uani 1 1 d . . . . .
H25A H 0.530551 0.222878 0.941723 0.070 Uiso 0.5 1 calc R . . E 1
H25B H 0.573253 0.298757 0.966909 0.070 Uiso 0.5 1 calc R . . E 1
H25C H 0.572803 0.245621 0.959432 0.070 Uiso 0.5 1 calc R . . F 2
H25D H 0.535285 0.325308 0.954172 0.070 Uiso 0.5 1 calc R . . F 2
C27 C 0.5537(3) 0.3490(2) 0.58958(19) 0.0365(9) Uani 1 1 d . . . . .
H27A H 0.517162 0.350802 0.547397 0.055 Uiso 1 1 calc GR . . . .
H27B H 0.579587 0.300852 0.596953 0.055 Uiso 1 1 calc GR . . . .
H27C H 0.592980 0.387844 0.595029 0.055 Uiso 1 1 calc GR . . . .
C28 C 0.4476(2) 0.2990(2) 0.62673(18) 0.0315(8) Uani 1 1 d . . . . .
H28A H 0.418986 0.305522 0.656239 0.047 Uiso 1 1 calc GR . . . .
H28B H 0.473908 0.251029 0.633630 0.047 Uiso 1 1 calc GR . . . .
H28C H 0.410911 0.301044 0.584593 0.047 Uiso 1 1 calc GR . . . .
C29 C 0.2792(3) 0.6208(2) 0.59525(19) 0.0382(9) Uani 1 1 d . . . . .
H29A H 0.320248 0.657710 0.600046 0.057 Uiso 1 1 calc GR . . . .
H29B H 0.235079 0.643071 0.604816 0.057 Uiso 1 1 calc GR . . . .
H29C H 0.261653 0.602637 0.552652 0.057 Uiso 1 1 calc GR . . . .
C30 C 0.2461(2) 0.4975(2) 0.63168(17) 0.0305(8) Uani 1 1 d . . . . .
H30A H 0.267453 0.456280 0.660542 0.037 Uiso 1 1 calc R . . . .
H30B H 0.203004 0.519936 0.643414 0.037 Uiso 1 1 calc R . . . .
C31 C 0.2130(3) 0.4665(3) 0.56644(19) 0.0434(10) Uani 1 1 d . . . . .
H31A H 0.182901 0.505702 0.538918 0.052 Uiso 1 1 calc R . . . .
H31B H 0.256972 0.452710 0.551684 0.052 Uiso 1 1 calc R . . . .
C32 C 0.1608(3) 0.4001(3) 0.5611(2) 0.0470(11) Uani 1 1 d . . . . .
H32A H 0.120137 0.411390 0.580259 0.056 Uiso 1 1 calc R . . . .
H32B H 0.134358 0.388787 0.517007 0.056 Uiso 1 1 calc R . . . .
C26 C 0.4546(5) 0.3066(5) 0.9396(4) 0.0406(13) Uani 0.5 1 d . . . G 1
H26A H 0.451808 0.293751 0.980879 0.049 Uiso 0.5 1 calc R . . G 1
H26B H 0.455579 0.360974 0.936812 0.049 Uiso 0.5 1 calc R . . G 1
C26A C 0.4654(5) 0.2480(5) 0.9385(4) 0.0406(13) Uani 0.5 1 d . . . G 2
H26C H 0.465889 0.254168 0.981649 0.049 Uiso 0.5 1 calc R . . G 2
H26D H 0.466006 0.194417 0.930532 0.049 Uiso 0.5 1 calc R . . G 2
O1S O 0.250000 0.2743(3) 0.500000 0.0653(15) Uani 1 2 d S T P . .
H1S H 0.243026 0.289761 0.464033 0.098 Uiso 0.5 1 calc GR . . H -1
C1S C 0.2852(6) 0.1998(5) 0.5068(6) 0.053(2) Uani 0.5 1 d . . . I -1
H1SA H 0.329482 0.196377 0.545673 0.063 Uiso 0.5 1 calc R . . I -1
H1SB H 0.304540 0.188926 0.471858 0.063 Uiso 0.5 1 calc R . . I -1
C2S C 0.2224(7) 0.1467(6) 0.5076(6) 0.060(3) Uani 0.5 1 d . . . I -1
H2SA H 0.177062 0.153859 0.470628 0.090 Uiso 0.5 1 calc GR . . I -1
H2SB H 0.207196 0.155206 0.544467 0.090 Uiso 0.5 1 calc GR . . I -1
H2SC H 0.241891 0.096235 0.508204 0.090 Uiso 0.5 1 calc GR . . I -1
N1A N 0.6203(2) 0.6142(2) 0.76299(17) 0.0444(9) Uani 1 1 d . . . . .
C1A C 0.5426(4) 0.6297(5) 0.7643(4) 0.086(2) Uani 1 1 d . . . . .
H1AA H 0.529431 0.681157 0.752597 0.129 Uiso 1 1 calc GR . . . .
H1AB H 0.540386 0.621228 0.806017 0.129 Uiso 1 1 calc GR . . . .
H1AC H 0.505153 0.597221 0.735168 0.129 Uiso 1 1 calc GR . . . .
C2A C 0.6797(4) 0.6484(4) 0.8191(3) 0.077(2) Uani 1 1 d . . . . .
H2AA H 0.732279 0.641965 0.816218 0.115 Uiso 1 1 calc GR . . . .
H2AB H 0.676637 0.624360 0.856565 0.115 Uiso 1 1 calc GR . . . .
H2AC H 0.668657 0.701116 0.820656 0.115 Uiso 1 1 calc GR . . . .
C3A C 0.6307(4) 0.6523(3) 0.7075(3) 0.0651(15) Uani 1 1 d . . . . .
H3AA H 0.624012 0.705502 0.710870 0.098 Uiso 1 1 calc GR . . . .
H3AB H 0.591601 0.633880 0.669875 0.098 Uiso 1 1 calc GR . . . .
H3AC H 0.683111 0.642145 0.705614 0.098 Uiso 1 1 calc GR . . . .
C4A C 0.6389(5) 0.5371(3) 0.7602(3) 0.081(2) Uani 1 1 d . . . . .
H4AA H 0.596130 0.512476 0.728631 0.121 Uiso 1 1 calc GR . . . .
H4AB H 0.646095 0.514059 0.800385 0.121 Uiso 1 1 calc GR . . . .
H4AC H 0.687129 0.532360 0.749629 0.121 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
O1 H1B 0.8400 . ?
O1 H1A 0.8400 . ?
O1 C26 1.398(9) . ?
O1 C26A 1.561(10) . ?
O2 H2B 0.8400 . ?
O2 H2A 0.8400 . ?
O2 C32 1.423(6) . ?
N1 H1 0.79(5) . ?
N1 C1 1.379(5) . ?
N1 C4 1.375(5) . ?
N2 H2 0.89(5) . ?
N2 C6 1.387(4) . ?
N2 C9 1.381(5) . ?
N3 H3 0.86(5) . ?
N3 C11 1.379(5) . ?
N3 C14 1.377(5) . ?
N4 H4 0.93(5) . ?
N4 C16 1.379(5) . ?
N4 C19 1.390(5) . ?
C1 C2 1.368(5) . ?
C1 C20 1.512(5) . ?
C2 H2C 0.9500 . ?
C2 C3 1.421(6) . ?
C3 H3A 0.9500 . ?
C3 C4 1.373(6) . ?
C4 C5 1.507(5) . ?
C5 C6 1.519(6) . ?
C5 C23 1.540(5) . ?
C5 C24 1.560(5) . ?
C6 C7 1.367(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.418(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.372(5) . ?
C9 C10 1.513(5) . ?
C10 C11 1.517(5) . ?
C10 C27 1.540(5) . ?
C10 C28 1.542(5) . ?
C11 C12 1.378(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.417(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(5) . ?
C14 C15 1.510(5) . ?
C15 C16 1.521(5) . ?
C15 C29 1.536(5) . ?
C15 C30 1.561(5) . ?
C16 C17 1.375(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.419(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.364(5) . ?
C19 C20 1.511(5) . ?
C20 C21 1.531(5) . ?
C20 C22 1.547(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.527(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 H25C 0.9900 . ?
C25 H25D 0.9900 . ?
C25 C26 1.503(10) . ?
C25 C26A 1.303(10) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.526(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.511(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26A H26C 0.9900 . ?
C26A H26D 0.9900 . ?
O1S H1S 0.8400 . ?
O1S C1S 1.481(10) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S C2S 1.492(13) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
N1A C1A 1.442(7) . ?
N1A C2A 1.518(7) . ?
N1A C3A 1.510(7) . ?
N1A C4A 1.446(7) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 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
C26 O1 H1A 109.5 . . ?
C26A O1 H1B 109.5 . . ?
C32 O2 H2B 109.5 . . ?
C32 O2 H2A 109.5 . . ?
C1 N1 H1 126(3) . . ?
C4 N1 H1 123(3) . . ?
C4 N1 C1 111.6(3) . . ?
C6 N2 H2 126(3) . . ?
C9 N2 H2 124(3) . . ?
C9 N2 C6 110.4(3) . . ?
C11 N3 H3 120(3) . . ?
C14 N3 H3 129(3) . . ?
C14 N3 C11 110.7(3) . . ?
C16 N4 H4 122(3) . . ?
C16 N4 C19 109.5(3) . . ?
C19 N4 H4 128(3) . . ?
N1 C1 C20 122.8(3) . . ?
C2 C1 N1 106.2(3) . . ?
C2 C1 C20 131.0(4) . . ?
C1 C2 H2C 126.0 . . ?
C1 C2 C3 108.0(4) . . ?
C3 C2 H2C 126.0 . . ?
C2 C3 H3A 125.8 . . ?
C4 C3 C2 108.5(4) . . ?
C4 C3 H3A 125.8 . . ?
N1 C4 C5 123.2(3) . . ?
C3 C4 N1 105.8(3) . . ?
C3 C4 C5 131.0(4) . . ?
C4 C5 C6 111.3(3) . . ?
C4 C5 C23 108.3(3) . . ?
C4 C5 C24 111.1(3) . . ?
C6 C5 C23 107.9(3) . . ?
C6 C5 C24 108.7(3) . . ?
C23 C5 C24 109.4(3) . . ?
N2 C6 C5 122.7(3) . . ?
C7 C6 N2 106.4(3) . . ?
C7 C6 C5 130.9(3) . . ?
C6 C7 H7 125.7 . . ?
C6 C7 C8 108.5(3) . . ?
C8 C7 H7 125.7 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.9(4) . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C10 122.6(3) . . ?
C8 C9 N2 106.8(3) . . ?
C8 C9 C10 130.6(4) . . ?
C9 C10 C11 111.1(3) . . ?
C9 C10 C27 108.6(3) . . ?
C9 C10 C28 110.5(3) . . ?
C11 C10 C27 108.3(3) . . ?
C11 C10 C28 109.6(3) . . ?
C27 C10 C28 108.7(3) . . ?
N3 C11 C10 122.2(3) . . ?
C12 C11 N3 106.8(3) . . ?
C12 C11 C10 131.0(3) . . ?
C11 C12 H12 126.0 . . ?
C11 C12 C13 108.0(3) . . ?
C13 C12 H12 126.0 . . ?
C12 C13 H13 126.1 . . ?
C14 C13 C12 107.9(3) . . ?
C14 C13 H13 126.1 . . ?
N3 C14 C13 106.7(3) . . ?
N3 C14 C15 122.4(3) . . ?
C13 C14 C15 130.9(3) . . ?
C14 C15 C16 110.9(3) . . ?
C14 C15 C29 108.8(3) . . ?
C14 C15 C30 109.8(3) . . ?
C16 C15 C29 108.2(3) . . ?
C16 C15 C30 109.8(3) . . ?
C29 C15 C30 109.3(3) . . ?
N4 C16 C15 122.7(3) . . ?
C17 C16 N4 107.4(3) . . ?
C17 C16 C15 129.9(3) . . ?
C16 C17 H17 126.2 . . ?
C16 C17 C18 107.6(3) . . ?
C18 C17 H17 126.2 . . ?
C17 C18 H18 125.9 . . ?
C19 C18 C17 108.3(3) . . ?
C19 C18 H18 125.9 . . ?
N4 C19 C20 122.5(3) . . ?
C18 C19 N4 107.2(3) . . ?
C18 C19 C20 130.3(3) . . ?
C1 C20 C21 108.2(3) . . ?
C1 C20 C22 109.4(3) . . ?
C19 C20 C1 111.5(3) . . ?
C19 C20 C21 108.8(3) . . ?
C19 C20 C22 110.6(3) . . ?
C21 C20 C22 108.2(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C5 C23 H23A 109.5 . . ?
C5 C23 H23B 109.5 . . ?
C5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 C24 H24A 108.0 . . ?
C5 C24 H24B 108.0 . . ?
H24A C24 H24B 107.3 . . ?
C25 C24 C5 117.1(4) . . ?
C25 C24 H24A 108.0 . . ?
C25 C24 H24B 108.0 . . ?
C24 C25 H25A 107.9 . . ?
C24 C25 H25B 107.9 . . ?
C24 C25 H25C 106.3 . . ?
C24 C25 H25D 106.3 . . ?
H25A C25 H25B 107.2 . . ?
H25C C25 H25D 106.4 . . ?
C26 C25 C24 117.5(5) . . ?
C26 C25 H25A 107.9 . . ?
C26 C25 H25B 107.9 . . ?
C26A C25 C24 124.0(6) . . ?
C26A C25 H25C 106.3 . . ?
C26A C25 H25D 106.3 . . ?
C10 C27 H27A 109.5 . . ?
C10 C27 H27B 109.5 . . ?
C10 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C10 C28 H28A 109.5 . . ?
C10 C28 H28B 109.5 . . ?
C10 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C15 C29 H29A 109.5 . . ?
C15 C29 H29B 109.5 . . ?
C15 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C15 C30 H30A 108.7 . . ?
C15 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C31 C30 C15 114.2(3) . . ?
C31 C30 H30A 108.7 . . ?
C31 C30 H30B 108.7 . . ?
C30 C31 H31A 108.7 . . ?
C30 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
C32 C31 C30 114.3(4) . . ?
C32 C31 H31A 108.7 . . ?
C32 C31 H31B 108.7 . . ?
O2 C32 C31 111.1(4) . . ?
O2 C32 H32A 109.4 . . ?
O2 C32 H32B 109.4 . . ?
C31 C32 H32A 109.4 . . ?
C31 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
O1 C26 C25 114.1(7) . . ?
O1 C26 H26A 108.7 . . ?
O1 C26 H26B 108.7 . . ?
C25 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
O1 C26A H26C 108.2 . . ?
O1 C26A H26D 108.2 . . ?
C25 C26A O1 116.2(7) . . ?
C25 C26A H26C 108.2 . . ?
C25 C26A H26D 108.2 . . ?
H26C C26A H26D 107.4 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S H1SA 110.4 . . ?
O1S C1S H1SB 110.4 . . ?
O1S C1S C2S 106.8(8) . . ?
H1SA C1S H1SB 108.6 . . ?
C2S C1S H1SA 110.4 . . ?
C2S C1S H1SB 110.4 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1A N1A C2A 109.4(5) . . ?
C1A N1A C3A 108.2(5) . . ?
C1A N1A C4A 115.6(6) . . ?
C3A N1A C2A 106.1(5) . . ?
C4A N1A C2A 108.8(4) . . ?
C4A N1A C3A 108.2(5) . . ?
N1A C1A H1AA 109.5 . . ?
N1A C1A H1AB 109.5 . . ?
N1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N1A C2A H2AA 109.5 . . ?
N1A C2A H2AB 109.5 . . ?
N1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
N1A C3A H3AA 109.5 . . ?
N1A C3A H3AB 109.5 . . ?
N1A C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
N1A C4A H4AA 109.5 . . ?
N1A C4A H4AB 109.5 . . ?
N1A C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?

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 H1B Cl1 0.84 2.62 3.407(4) 156.4 . yes
O1 H1A O2 0.84 2.02 2.795(5) 152.9 7_556 yes
O2 H2B O1 0.84 2.01 2.795(5) 155.0 7_556 yes
O2 H2A O1S 0.84 1.89 2.720(4) 168.6 . yes
N1 H1 Cl1 0.79(5) 2.54(5) 3.326(3) 176(5) . yes
N2 H2 Cl1 0.89(5) 2.44(5) 3.334(3) 177(4) . yes
N3 H3 Cl1 0.86(5) 2.53(5) 3.380(3) 170(5) . yes
N4 H4 Cl1 0.93(5) 2.39(5) 3.317(3) 175(4) . yes

_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
;
####################################################################### 
# 
# 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_mo_CP002_0m
_database_code_depnum_ccdc_archive 'CCDC 2248773'
loop_
_audit_author_name
_audit_author_address
'Evgeny Bulatov'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N3 O2'
_chemical_formula_weight         347.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   8.9833(6)
_cell_length_b                   8.8691(5)
_cell_length_c                   22.8632(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.4001(18)
_cell_angle_gamma                90
_cell_volume                     1813.51(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1928
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      33.98

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7024
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   SADABS-2014/4
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            33726
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.789
_diffrn_reflns_theta_max         34.965
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7532
_reflns_number_gt                5861
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2 v2014.9-0'
_computing_cell_refinement       'Bruker APEX2 v2014.9-0'
_computing_data_reduction        'Bruker APEX2 v2014.9-0'
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0716P)²+0.3389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7532
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_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_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
N1 N 0.40483(9) 0.40735(9) 0.12386(3) 0.01628(15) Uani 1 1 d . . . . .
N2 N 0.70290(8) 0.81853(9) 0.08130(3) 0.01581(14) Uani 1 1 d . . . . .
H1N H 0.720655 0.778847 0.047373 0.019 Uiso 1 1 calc R U . . .
N3 N 1.11811(9) 0.77861(10) 0.15273(4) 0.01882(16) Uani 1 1 d . . . . .
H2N H 1.105301 0.812549 0.188078 0.023 Uiso 1 1 calc R U . . .
O1 O 0.40696(9) 0.41755(9) 0.22482(3) 0.02310(15) Uani 1 1 d . . . . .
O2 O 0.34759(9) 0.34574(10) 0.02640(3) 0.02632(17) Uani 1 1 d . . . . .
C18 C 0.76324(9) 0.76861(10) 0.13521(4) 0.01363(15) Uani 1 1 d . . . . .
C13 C 1.01990(10) 0.68668(10) 0.11996(4) 0.01477(15) Uani 1 1 d . . . . .
C2 C 0.21425(10) 0.28008(10) 0.16353(4) 0.01674(16) Uani 1 1 d . . . . .
C7 C 0.19692(10) 0.25725(10) 0.10308(4) 0.01721(16) Uani 1 1 d . . . . .
C12 C 0.87250(9) 0.63799(10) 0.14175(4) 0.01449(15) Uani 1 1 d . . . . .
C9 C 0.53421(10) 0.50334(10) 0.11641(4) 0.01692(16) Uani 1 1 d . . . . .
H9A H 0.538785 0.585395 0.145887 0.020 Uiso 1 1 calc R U . . .
H9B H 0.522424 0.549911 0.076897 0.020 Uiso 1 1 calc R U . . .
C8 C 0.31987(10) 0.33859(10) 0.07739(4) 0.01748(17) Uani 1 1 d . . . . .
C16 C 1.23941(11) 0.81009(12) 0.12242(5) 0.0238(2) Uani 1 1 d . . . . .
H16 H 1.322225 0.871668 0.135807 0.029 Uiso 1 1 calc R U . . .
C10 C 0.67961(11) 0.41374(11) 0.12347(5) 0.02042(18) Uani 1 1 d . . . . .
H10A H 0.666165 0.320239 0.099906 0.025 Uiso 1 1 calc R U . . .
H10B H 0.699931 0.383899 0.165178 0.025 Uiso 1 1 calc R U . . .
C14 C 1.08115(11) 0.65894(12) 0.06796(5) 0.02201(19) Uani 1 1 d . . . . .
H14 H 1.038362 0.598268 0.036504 0.026 Uiso 1 1 calc R U . . .
C19 C 0.70868(10) 0.86122(10) 0.17689(4) 0.01702(16) Uani 1 1 d . . . . .
H19 H 0.731128 0.853809 0.218228 0.020 Uiso 1 1 calc R U . . .
C11 C 0.81629(10) 0.49879(10) 0.10476(4) 0.01809(17) Uani 1 1 d . . . . .
H11A H 0.792634 0.532467 0.063655 0.022 Uiso 1 1 calc R U . . .
H11B H 0.900049 0.426195 0.104938 0.022 Uiso 1 1 calc R U . . .
C20 C 0.61286(10) 0.96967(11) 0.14684(4) 0.01998(18) Uani 1 1 d . . . . .
H20 H 0.560340 1.048150 0.164323 0.024 Uiso 1 1 calc R U . . .
C17 C 0.89731(11) 0.59444(11) 0.20682(4) 0.02086(18) Uani 1 1 d . . . . .
H17A H 0.965024 0.507736 0.211397 0.031 Uiso 1 1 calc R U . . .
H17B H 0.801280 0.567965 0.221183 0.031 Uiso 1 1 calc R U . . .
H17C H 0.941483 0.679794 0.229494 0.031 Uiso 1 1 calc R U . . .
C5 C -0.02236(11) 0.11374(12) 0.11329(5) 0.0253(2) Uani 1 1 d . . . . .
H5 H -0.104845 0.056084 0.096629 0.030 Uiso 1 1 calc R U . . .
C21 C 0.61059(10) 0.93973(11) 0.08813(4) 0.01953(17) Uani 1 1 d . . . . .
H21 H 0.554979 0.993264 0.057401 0.023 Uiso 1 1 calc R U . . .
C3 C 0.11489(11) 0.22043(11) 0.20021(5) 0.02178(19) Uani 1 1 d . . . . .
H3 H 0.127694 0.235290 0.241523 0.026 Uiso 1 1 calc R U . . .
C6 C 0.07943(11) 0.17323(11) 0.07648(5) 0.02235(19) Uani 1 1 d . . . . .
H6 H 0.068309 0.156675 0.035245 0.027 Uiso 1 1 calc R U . . .
C15 C 1.21988(11) 0.73728(12) 0.06971(5) 0.0247(2) Uani 1 1 d . . . . .
H15 H 1.286365 0.738579 0.039764 0.030 Uiso 1 1 calc R U . . .
C1 C 0.34965(10) 0.37513(10) 0.17730(4) 0.01630(16) Uani 1 1 d . . . . .
C4 C -0.00504(11) 0.13738(12) 0.17348(5) 0.0254(2) Uani 1 1 d . . . . .
H4 H -0.076409 0.096134 0.197127 0.031 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
N1 C8 1.3895(12) . ?
N1 C1 1.3908(12) . ?
N1 C9 1.4635(11) . ?
N2 C18 1.3722(12) . ?
N2 C21 1.3755(12) . ?
N3 C13 1.3712(12) . ?
N3 C16 1.3739(12) . ?
O1 C1 1.2171(11) . ?
O2 C8 1.2164(12) . ?
C18 C19 1.3823(12) . ?
C18 C12 1.5166(12) . ?
C13 C14 1.3784(13) . ?
C13 C12 1.5205(12) . ?
C2 C3 1.3858(13) . ?
C2 C7 1.3911(13) . ?
C2 C1 1.4891(12) . ?
C7 C6 1.3850(13) . ?
C7 C8 1.4857(13) . ?
C12 C17 1.5330(13) . ?
C12 C11 1.5537(13) . ?
C9 C10 1.5245(13) . ?
C16 C15 1.3641(16) . ?
C10 C11 1.5357(13) . ?
C14 C15 1.4241(14) . ?
C19 C20 1.4236(14) . ?
C20 C21 1.3666(14) . ?
C5 C4 1.3863(17) . ?
C5 C6 1.4027(15) . ?
C3 C4 1.3974(15) . ?

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
C8 N1 C1 111.47(7) . . ?
C8 N1 C9 123.47(8) . . ?
C1 N1 C9 125.05(8) . . ?
C18 N2 C21 109.98(8) . . ?
C13 N3 C16 110.20(8) . . ?
N2 C18 C19 106.96(8) . . ?
N2 C18 C12 122.16(8) . . ?
C19 C18 C12 130.85(8) . . ?
N3 C13 C14 106.79(8) . . ?
N3 C13 C12 121.69(8) . . ?
C14 C13 C12 131.49(8) . . ?
C3 C2 C7 121.83(9) . . ?
C3 C2 C1 130.39(9) . . ?
C7 C2 C1 107.78(8) . . ?
C6 C7 C2 121.60(9) . . ?
C6 C7 C8 130.68(9) . . ?
C2 C7 C8 107.71(8) . . ?
C18 C12 C13 109.04(7) . . ?
C18 C12 C17 108.77(7) . . ?
C13 C12 C17 109.75(7) . . ?
C18 C12 C11 112.28(7) . . ?
C13 C12 C11 107.20(7) . . ?
C17 C12 C11 109.76(7) . . ?
N1 C9 C10 111.49(7) . . ?
O2 C8 N1 124.24(9) . . ?
O2 C8 C7 129.12(9) . . ?
N1 C8 C7 106.63(8) . . ?
C15 C16 N3 107.89(9) . . ?
C9 C10 C11 114.46(8) . . ?
C13 C14 C15 107.94(9) . . ?
C18 C19 C20 107.83(8) . . ?
C10 C11 C12 117.79(8) . . ?
C21 C20 C19 107.17(8) . . ?
C4 C5 C6 121.34(9) . . ?
C20 C21 N2 108.05(9) . . ?
C2 C3 C4 116.78(10) . . ?
C7 C6 C5 116.86(10) . . ?
C16 C15 C14 107.17(9) . . ?
O1 C1 N1 124.39(8) . . ?
O1 C1 C2 129.22(9) . . ?
N1 C1 C2 106.39(8) . . ?
C5 C4 C3 121.58(9) . . ?

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
C21 N2 C18 C19 -0.50(10) . . . . ?
C21 N2 C18 C12 -178.65(7) . . . . ?
C16 N3 C13 C14 0.34(11) . . . . ?
C16 N3 C13 C12 -177.78(8) . . . . ?
C3 C2 C7 C6 -0.18(15) . . . . ?
C1 C2 C7 C6 -179.60(9) . . . . ?
C3 C2 C7 C8 178.84(9) . . . . ?
C1 C2 C7 C8 -0.58(10) . . . . ?
N2 C18 C12 C13 69.75(10) . . . . ?
C19 C18 C12 C13 -107.91(10) . . . . ?
N2 C18 C12 C17 -170.59(8) . . . . ?
C19 C18 C12 C17 11.75(12) . . . . ?
N2 C18 C12 C11 -48.91(10) . . . . ?
C19 C18 C12 C11 133.43(9) . . . . ?
N3 C13 C12 C18 76.00(10) . . . . ?
C14 C13 C12 C18 -101.59(12) . . . . ?
N3 C13 C12 C17 -43.05(11) . . . . ?
C14 C13 C12 C17 139.36(11) . . . . ?
N3 C13 C12 C11 -162.21(8) . . . . ?
C14 C13 C12 C11 20.20(14) . . . . ?
C8 N1 C9 C10 -93.96(11) . . . . ?
C1 N1 C9 C10 87.16(11) . . . . ?
C1 N1 C8 O2 -177.77(10) . . . . ?
C9 N1 C8 O2 3.21(15) . . . . ?
C1 N1 C8 C7 1.25(11) . . . . ?
C9 N1 C8 C7 -177.77(8) . . . . ?
C6 C7 C8 O2 -2.50(18) . . . . ?
C2 C7 C8 O2 178.60(11) . . . . ?
C6 C7 C8 N1 178.54(10) . . . . ?
C2 C7 C8 N1 -0.36(11) . . . . ?
C13 N3 C16 C15 -0.31(12) . . . . ?
N1 C9 C10 C11 168.85(8) . . . . ?
N3 C13 C14 C15 -0.24(11) . . . . ?
C12 C13 C14 C15 177.63(9) . . . . ?
N2 C18 C19 C20 0.00(10) . . . . ?
C12 C18 C19 C20 177.93(8) . . . . ?
C9 C10 C11 C12 66.71(12) . . . . ?
C18 C12 C11 C10 -68.42(10) . . . . ?
C13 C12 C11 C10 171.84(8) . . . . ?
C17 C12 C11 C10 52.70(11) . . . . ?
C18 C19 C20 C21 0.50(10) . . . . ?
C19 C20 C21 N2 -0.79(11) . . . . ?
C18 N2 C21 C20 0.82(10) . . . . ?
C7 C2 C3 C4 -0.72(14) . . . . ?
C1 C2 C3 C4 178.56(10) . . . . ?
C2 C7 C6 C5 0.76(15) . . . . ?
C8 C7 C6 C5 -178.01(10) . . . . ?
C4 C5 C6 C7 -0.45(15) . . . . ?
N3 C16 C15 C14 0.15(12) . . . . ?
C13 C14 C15 C16 0.06(12) . . . . ?
C8 N1 C1 O1 177.40(9) . . . . ?
C9 N1 C1 O1 -3.60(15) . . . . ?
C8 N1 C1 C2 -1.60(10) . . . . ?
C9 N1 C1 C2 177.40(8) . . . . ?
C3 C2 C1 O1 3.03(17) . . . . ?
C7 C2 C1 O1 -177.61(10) . . . . ?
C3 C2 C1 N1 -178.04(10) . . . . ?
C7 C2 C1 N1 1.32(10) . . . . ?
C6 C5 C4 C3 -0.46(16) . . . . ?
C2 C3 C4 C5 1.03(15) . . . . ?

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_tiy-013cis
_database_code_depnum_ccdc_archive 'CCDC 2248776'
loop_
_audit_author_name
_audit_author_address
'Evgeny Bulatov'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_audit_creation_date             2023-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H44 N4 O2, C H2 O0.25'
_chemical_formula_sum            'C33 H46 N4 O2.25'
_chemical_formula_weight         534.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   34.4880(3)
_cell_length_b                   34.4880(3)
_cell_length_c                   10.29560(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     12245.8(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    5201
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      72.2980
_cell_measurement_theta_min      2.5370
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             4640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0244
0 -1 0 0.0049
2 5 1 0.0779
0 1 0 0.0367
0 0 1 0.1260
0 0 -1 0.1068
-1 0 0 0.0244

_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9771
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.482
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00   60.00    --  -41.90 125.00 150.00   81
  2  ω    114.00 178.00   1.00  180.00    --  103.21  77.00   0.00   64
  3  ω     33.00  93.00   1.00  180.00    --  103.21-125.00  90.00   60
  4  ω    113.00 178.00   1.00  180.00    --  103.21  77.00 150.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4668
_reflns_number_total             5356
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.296
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         5356
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.059
_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)+(0.1202P)²+14.2548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1770
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1S-C1S
 1.42 with sigma of 0.02
 C1S-C2S
 1.52 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1S \\sim C1S \\sim C2S: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(O1S) \\sim Ueq, Uanis(C1S) \\sim Ueq, Uanis(C2S) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C1S(0.5) H1SA(0.5) H1SB(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,
 H31B), C32(H32A,H32B), C1S(H1SA,H1SB), C2S(H2SA,H2SB)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2B), C3(H3A), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17), C18(H18)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
5.d Idealised tetrahedral OH refined with riding coordinates:
 O1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.58649(4) 0.64285(5) 0.4513(2) 0.0397(4) Uani 1 1 d . . . . .
H1A H 0.590355 0.634251 0.526495 0.27(5) Uiso 1 1 calc R . . . .
O2 O 0.21401(4) 0.63638(4) 1.04729(14) 0.0234(3) Uani 1 1 d . . . . .
H2A H 0.2098(9) 0.6104(10) 1.061(3) 0.049(8) Uiso 1 1 d . . . . .
N1 N 0.37831(4) 0.59551(5) 0.57690(15) 0.0185(4) Uani 1 1 d . . . . .
H1 H 0.3810(6) 0.5727(7) 0.626(2) 0.019(5) Uiso 1 1 d . . . . .
N2 N 0.33060(4) 0.60508(5) 0.85987(15) 0.0166(3) Uani 1 1 d . . . . .
H2 H 0.3466(7) 0.6270(8) 0.846(2) 0.028(6) Uiso 1 1 d . . . . .
N3 N 0.41200(4) 0.59041(4) 1.01606(15) 0.0168(3) Uani 1 1 d . . . . .
H3 H 0.4047(8) 0.5693(8) 0.960(3) 0.032(7) Uiso 1 1 d . . . . .
N4 N 0.46045(4) 0.59625(5) 0.73872(15) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.4475(8) 0.6184(8) 0.757(3) 0.034(7) Uiso 1 1 d . . . . .
C1 C 0.40803(5) 0.61594(6) 0.51820(18) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.39308(6) 0.65089(6) 0.47993(19) 0.0238(4) Uani 1 1 d . . . . .
H2B H 0.406840 0.670964 0.436689 0.029 Uiso 1 1 calc R . . . .
C3 C 0.35335(6) 0.65185(6) 0.51632(19) 0.0248(4) Uani 1 1 d . . . . .
H3A H 0.335826 0.672647 0.501543 0.030 Uiso 1 1 calc R . . . .
C4 C 0.34481(6) 0.61755(6) 0.57635(18) 0.0204(4) Uani 1 1 d . . . . .
C5 C 0.30656(5) 0.60213(6) 0.62777(19) 0.0219(4) Uani 1 1 d . . . . .
C6 C 0.31051(5) 0.58597(6) 0.76372(19) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.29406(6) 0.55366(6) 0.8198(2) 0.0233(4) Uani 1 1 d . . . . .
H7 H 0.278539 0.534851 0.776874 0.028 Uiso 1 1 calc R . . . .
C8 C 0.30447(5) 0.55352(6) 0.9532(2) 0.0216(4) Uani 1 1 d . . . . .
H8 H 0.297047 0.534636 1.015588 0.026 Uiso 1 1 calc R . . . .
C9 C 0.32714(5) 0.58544(5) 0.97595(18) 0.0172(4) Uani 1 1 d . . . . .
C10 C 0.34401(5) 0.60124(5) 1.09983(18) 0.0181(4) Uani 1 1 d . . . . .
C11 C 0.38571(5) 0.61346(5) 1.08097(17) 0.0171(4) Uani 1 1 d . . . . .
C12 C 0.40571(6) 0.64470(6) 1.12893(19) 0.0219(4) Uani 1 1 d . . . . .
H12 H 0.395074 0.665333 1.178628 0.026 Uiso 1 1 calc R . . . .
C13 C 0.44500(6) 0.64079(6) 1.09133(19) 0.0213(4) Uani 1 1 d . . . . .
H13 H 0.465420 0.658325 1.110935 0.026 Uiso 1 1 calc R . . . .
C14 C 0.44821(5) 0.60724(5) 1.02180(18) 0.0182(4) Uani 1 1 d . . . . .
C15 C 0.48371(5) 0.58722(6) 0.96849(18) 0.0206(4) Uani 1 1 d . . . . .
C16 C 0.47778(5) 0.57318(6) 0.83104(18) 0.0183(4) Uani 1 1 d . . . . .
C17 C 0.49003(6) 0.54007(6) 0.7698(2) 0.0237(4) Uani 1 1 d . . . . .
H17 H 0.503247 0.518961 0.809214 0.028 Uiso 1 1 calc R . . . .
C18 C 0.47944(6) 0.54299(6) 0.63727(19) 0.0233(4) Uani 1 1 d . . . . .
H18 H 0.484268 0.524174 0.571836 0.028 Uiso 1 1 calc R . . . .
C19 C 0.46097(5) 0.57781(6) 0.62029(18) 0.0184(4) Uani 1 1 d . . . . .
C20 C 0.44783(5) 0.59805(6) 0.49832(18) 0.0194(4) Uani 1 1 d . . . . .
C21 C 0.29154(6) 0.57017(7) 0.5362(2) 0.0328(5) Uani 1 1 d . . . . .
H21A H 0.266089 0.561244 0.566159 0.049 Uiso 1 1 calc GR . . . .
H21B H 0.309763 0.548373 0.536165 0.049 Uiso 1 1 calc GR . . . .
H21C H 0.289202 0.580573 0.447944 0.049 Uiso 1 1 calc GR . . . .
C22 C 0.27671(6) 0.63531(7) 0.6308(2) 0.0315(5) Uani 1 1 d . . . . .
H22A H 0.286356 0.656275 0.686360 0.047 Uiso 1 1 calc GR . . . .
H22B H 0.252086 0.625619 0.665446 0.047 Uiso 1 1 calc GR . . . .
H22C H 0.272701 0.645164 0.542541 0.047 Uiso 1 1 calc GR . . . .
C23 C 0.34297(6) 0.56974(6) 1.2059(2) 0.0251(4) Uani 1 1 d . . . . .
H23A H 0.357797 0.547104 1.176922 0.038 Uiso 1 1 calc GR . . . .
H23B H 0.316037 0.562119 1.222341 0.038 Uiso 1 1 calc GR . . . .
H23C H 0.354412 0.579975 1.286048 0.038 Uiso 1 1 calc GR . . . .
C24 C 0.49389(7) 0.55246(7) 1.0560(2) 0.0304(5) Uani 1 1 d . . . . .
H24A H 0.498466 0.561570 1.144848 0.046 Uiso 1 1 calc GR . . . .
H24B H 0.517329 0.539766 1.023054 0.046 Uiso 1 1 calc GR . . . .
H24C H 0.472343 0.533935 1.055775 0.046 Uiso 1 1 calc GR . . . .
C25 C 0.51764(6) 0.61599(7) 0.9712(2) 0.0314(5) Uani 1 1 d . . . . .
H25A H 0.511480 0.638353 0.916172 0.047 Uiso 1 1 calc GR . . . .
H25B H 0.541090 0.603251 0.938482 0.047 Uiso 1 1 calc GR . . . .
H25C H 0.522011 0.624741 1.060525 0.047 Uiso 1 1 calc GR . . . .
C26 C 0.44543(6) 0.56879(6) 0.38559(19) 0.0247(4) Uani 1 1 d . . . . .
H26A H 0.426467 0.548600 0.406808 0.037 Uiso 1 1 calc GR . . . .
H26B H 0.470924 0.556903 0.372026 0.037 Uiso 1 1 calc GR . . . .
H26C H 0.437385 0.582247 0.306213 0.037 Uiso 1 1 calc GR . . . .
C27 C 0.47702(5) 0.63075(6) 0.46368(19) 0.0224(4) Uani 1 1 d . . . . .
H27A H 0.469873 0.641590 0.377932 0.027 Uiso 1 1 calc R . . . .
H27B H 0.474363 0.651790 0.528480 0.027 Uiso 1 1 calc R . . . .
C28 C 0.51947(6) 0.61823(7) 0.4590(3) 0.0322(5) Uani 1 1 d . . . . .
H28A H 0.526352 0.605558 0.542151 0.039 Uiso 1 1 calc R . . . .
H28B H 0.522887 0.598925 0.388748 0.039 Uiso 1 1 calc R . . . .
C29 C 0.54652(6) 0.65179(7) 0.4359(2) 0.0329(5) Uani 1 1 d . . . . .
H29A H 0.542338 0.661591 0.346580 0.039 Uiso 1 1 calc R . . . .
H29B H 0.539715 0.672933 0.496760 0.039 Uiso 1 1 calc R . . . .
C30 C 0.32066(5) 0.63731(6) 1.14668(19) 0.0215(4) Uani 1 1 d . . . . .
H30A H 0.330668 0.645105 1.232949 0.026 Uiso 1 1 calc R . . . .
H30B H 0.325801 0.658969 1.085964 0.026 Uiso 1 1 calc R . . . .
C31 C 0.27655(6) 0.63186(6) 1.1573(2) 0.0244(4) Uani 1 1 d . . . . .
H31A H 0.271006 0.604386 1.178113 0.029 Uiso 1 1 calc R . . . .
H31B H 0.266743 0.647878 1.230014 0.029 Uiso 1 1 calc R . . . .
C32 C 0.25490(5) 0.64281(6) 1.0344(2) 0.0242(4) Uani 1 1 d . . . . .
H32A H 0.259639 0.670500 1.014589 0.029 Uiso 1 1 calc R . . . .
H32B H 0.264931 0.627243 0.960890 0.029 Uiso 1 1 calc R . . . .
O1S O 0.500000 0.750000 0.625000 0.366(10) Uani 1 4 d DS TU P . .
C1S C 0.5285(5) 0.7563(5) 0.5035(14) 0.172(6) Uani 0.5 1 d D U . . .
H1SA H 0.542863 0.780428 0.523878 0.206 Uiso 0.5 1 calc R . . . .
H1SB H 0.547709 0.735094 0.510126 0.206 Uiso 0.5 1 calc R . . . .
C2S C 0.5200(2) 0.7591(2) 0.3683(12) 0.093(3) Uani 0.5 1 d D U . . .
H2SA H 0.538557 0.744079 0.314930 0.111 Uiso 0.5 1 calc R . . . .
H2SB H 0.519362 0.786327 0.338140 0.111 Uiso 0.5 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 H1A 0.8400 . ?
O1 C29 1.421(3) . ?
O2 H2A 0.92(3) . ?
O2 C32 1.434(2) . ?
N1 H1 0.94(3) . ?
N1 C1 1.383(2) . ?
N1 C4 1.383(3) . ?
N2 H2 0.95(3) . ?
N2 C6 1.376(2) . ?
N2 C9 1.379(2) . ?
N3 H3 0.96(3) . ?
N3 C11 1.379(2) . ?
N3 C14 1.378(2) . ?
N4 H4 0.91(3) . ?
N4 C16 1.376(2) . ?
N4 C19 1.375(2) . ?
C1 C2 1.369(3) . ?
C1 C20 1.519(3) . ?
C2 H2B 0.9500 . ?
C2 C3 1.421(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.367(3) . ?
C4 C5 1.518(3) . ?
C5 C6 1.513(3) . ?
C5 C21 1.540(3) . ?
C5 C22 1.540(3) . ?
C6 C7 1.377(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.420(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(3) . ?
C9 C10 1.504(3) . ?
C10 C11 1.511(3) . ?
C10 C23 1.541(3) . ?
C10 C30 1.558(3) . ?
C11 C12 1.371(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.416(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.365(3) . ?
C14 C15 1.509(3) . ?
C15 C16 1.510(3) . ?
C15 C24 1.540(3) . ?
C15 C25 1.534(3) . ?
C16 C17 1.371(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.416(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.371(3) . ?
C19 C20 1.506(3) . ?
C20 C26 1.540(3) . ?
C20 C27 1.553(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.527(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.506(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.537(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.517(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
O1S C1S 1.606(13) 12_767 ?
O1S C1S 1.606(13) 6_564 ?
O1S C1S 1.606(13) 15_566 ?
O1S C1S 1.606(13) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S C2S 1.426(14) . ?
C2S C2S 1.513(16) 6_564 ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?

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
C29 O1 H1A 109.5 . . ?
C32 O2 H2A 108.6(19) . . ?
C1 N1 H1 125.9(14) . . ?
C1 N1 C4 109.72(16) . . ?
C4 N1 H1 123.2(14) . . ?
C6 N2 H2 124.4(15) . . ?
C6 N2 C9 110.14(16) . . ?
C9 N2 H2 125.2(16) . . ?
C11 N3 H3 123.6(16) . . ?
C14 N3 H3 125.6(16) . . ?
C14 N3 C11 109.41(16) . . ?
C16 N4 H4 123.8(18) . . ?
C19 N4 H4 125.7(18) . . ?
C19 N4 C16 109.85(16) . . ?
N1 C1 C20 121.45(17) . . ?
C2 C1 N1 107.18(17) . . ?
C2 C1 C20 131.25(18) . . ?
C1 C2 H2B 126.0 . . ?
C1 C2 C3 107.92(17) . . ?
C3 C2 H2B 126.0 . . ?
C2 C3 H3A 126.1 . . ?
C4 C3 C2 107.87(17) . . ?
C4 C3 H3A 126.1 . . ?
N1 C4 C5 122.15(17) . . ?
C3 C4 N1 107.31(17) . . ?
C3 C4 C5 130.42(18) . . ?
C4 C5 C21 109.24(16) . . ?
C4 C5 C22 109.13(17) . . ?
C6 C5 C4 111.94(15) . . ?
C6 C5 C21 109.46(17) . . ?
C6 C5 C22 108.38(16) . . ?
C22 C5 C21 108.62(17) . . ?
N2 C6 C5 122.30(17) . . ?
N2 C6 C7 107.07(17) . . ?
C7 C6 C5 130.45(18) . . ?
C6 C7 H7 126.1 . . ?
C6 C7 C8 107.70(17) . . ?
C8 C7 H7 126.1 . . ?
C7 C8 H8 126.1 . . ?
C9 C8 C7 107.88(17) . . ?
C9 C8 H8 126.1 . . ?
N2 C9 C10 121.55(16) . . ?
C8 C9 N2 107.21(16) . . ?
C8 C9 C10 131.06(17) . . ?
C9 C10 C11 111.11(15) . . ?
C9 C10 C23 109.67(16) . . ?
C9 C10 C30 110.60(15) . . ?
C11 C10 C23 108.05(15) . . ?
C11 C10 C30 107.99(15) . . ?
C23 C10 C30 109.35(15) . . ?
N3 C11 C10 121.84(16) . . ?
C12 C11 N3 107.26(16) . . ?
C12 C11 C10 130.66(17) . . ?
C11 C12 H12 126.0 . . ?
C11 C12 C13 107.94(17) . . ?
C13 C12 H12 126.0 . . ?
C12 C13 H13 126.2 . . ?
C14 C13 C12 107.57(17) . . ?
C14 C13 H13 126.2 . . ?
N3 C14 C15 121.79(17) . . ?
C13 C14 N3 107.81(16) . . ?
C13 C14 C15 130.13(17) . . ?
C14 C15 C16 112.20(15) . . ?
C14 C15 C24 109.17(16) . . ?
C14 C15 C25 108.44(16) . . ?
C16 C15 C24 109.25(16) . . ?
C16 C15 C25 109.12(16) . . ?
C25 C15 C24 108.61(18) . . ?
N4 C16 C15 121.40(17) . . ?
C17 C16 N4 107.32(17) . . ?
C17 C16 C15 131.03(17) . . ?
C16 C17 H17 126.1 . . ?
C16 C17 C18 107.73(17) . . ?
C18 C17 H17 126.1 . . ?
C17 C18 H18 126.1 . . ?
C19 C18 C17 107.75(17) . . ?
C19 C18 H18 126.1 . . ?
N4 C19 C20 121.41(16) . . ?
C18 C19 N4 107.34(16) . . ?
C18 C19 C20 130.69(18) . . ?
C1 C20 C26 108.62(15) . . ?
C1 C20 C27 108.77(16) . . ?
C19 C20 C1 110.35(15) . . ?
C19 C20 C26 109.93(16) . . ?
C19 C20 C27 109.43(15) . . ?
C26 C20 C27 109.72(16) . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 C22 H22A 109.5 . . ?
C5 C22 H22B 109.5 . . ?
C5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23A 109.5 . . ?
C10 C23 H23B 109.5 . . ?
C10 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C25 H25A 109.5 . . ?
C15 C25 H25B 109.5 . . ?
C15 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C20 C27 H27A 108.5 . . ?
C20 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C28 C27 C20 115.04(17) . . ?
C28 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
C27 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 C27 112.44(18) . . ?
C29 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
O1 C29 C28 114.62(19) . . ?
O1 C29 H29A 108.6 . . ?
O1 C29 H29B 108.6 . . ?
C28 C29 H29A 108.6 . . ?
C28 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C10 C30 H30A 108.3 . . ?
C10 C30 H30B 108.3 . . ?
H30A C30 H30B 107.4 . . ?
C31 C30 C10 115.84(16) . . ?
C31 C30 H30A 108.3 . . ?
C31 C30 H30B 108.3 . . ?
C30 C31 H31A 108.9 . . ?
C30 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C32 C31 C30 113.41(17) . . ?
C32 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
O2 C32 C31 111.60(16) . . ?
O2 C32 H32A 109.3 . . ?
O2 C32 H32B 109.3 . . ?
C31 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
H32A C32 H32B 108.0 . . ?
C1S O1S C1S 127.4(8) 12_767 . ?
C1S O1S C1S 77.6(13) 12_767 15_566 ?
C1S O1S C1S 77.6(13) 6_564 . ?
C1S O1S C1S 127.4(8) 15_566 . ?
C1S O1S C1S 127.4(8) 15_566 6_564 ?
C1S O1S C1S 127.4(8) 12_767 6_564 ?
O1S C1S H1SA 104.8 . . ?
O1S C1S H1SB 104.8 . . ?
H1SA C1S H1SB 105.8 . . ?
C2S C1S O1S 130.0(13) . . ?
C2S C1S H1SA 104.8 . . ?
C2S C1S H1SB 104.8 . . ?
C1S C2S C2S 99.2(8) . 6_564 ?
C1S C2S H2SA 111.9 . . ?
C1S C2S H2SB 111.9 . . ?
C2S C2S H2SA 111.9 6_564 . ?
C2S C2S H2SB 111.9 6_564 . ?
H2SA C2S H2SB 109.6 . . ?

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
N1 H1 O2 0.94(3) 2.18(3) 3.073(2) 158(2) 4_454 yes
N2 H2 O1 0.95(3) 2.09(3) 3.011(2) 164(2) 15_566 yes
N3 H3 O2 0.96(3) 2.13(3) 3.062(2) 164(2) 4_454 yes
N4 H4 O1 0.91(3) 2.48(3) 3.346(2) 160(2) 15_566 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
N1 C1 C2 C3 0.1(2) . . . . ?
N1 C1 C20 C19 -45.7(2) . . . . ?
N1 C1 C20 C26 74.9(2) . . . . ?
N1 C1 C20 C27 -165.74(17) . . . . ?
N1 C4 C5 C6 52.3(2) . . . . ?
N1 C4 C5 C21 -69.1(2) . . . . ?
N1 C4 C5 C22 172.27(17) . . . . ?
N2 C6 C7 C8 0.2(2) . . . . ?
N2 C9 C10 C11 -49.2(2) . . . . ?
N2 C9 C10 C23 -168.60(16) . . . . ?
N2 C9 C10 C30 70.7(2) . . . . ?
N3 C11 C12 C13 0.6(2) . . . . ?
N3 C14 C15 C16 50.8(2) . . . . ?
N3 C14 C15 C24 -70.4(2) . . . . ?
N3 C14 C15 C25 171.42(17) . . . . ?
N4 C16 C17 C18 -0.7(2) . . . . ?
N4 C19 C20 C1 -51.3(2) . . . . ?
N4 C19 C20 C26 -171.10(16) . . . . ?
N4 C19 C20 C27 68.3(2) . . . . ?
C1 N1 C4 C3 0.4(2) . . . . ?
C1 N1 C4 C5 176.74(17) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C20 C27 C28 171.94(18) . . . . ?
C2 C1 C20 C19 139.0(2) . . . . ?
C2 C1 C20 C26 -100.5(2) . . . . ?
C2 C1 C20 C27 18.9(3) . . . . ?
C2 C3 C4 N1 -0.4(2) . . . . ?
C2 C3 C4 C5 -176.24(19) . . . . ?
C3 C4 C5 C6 -132.3(2) . . . . ?
C3 C4 C5 C21 106.3(2) . . . . ?
C3 C4 C5 C22 -12.4(3) . . . . ?
C4 N1 C1 C2 -0.3(2) . . . . ?
C4 N1 C1 C20 -176.67(17) . . . . ?
C4 C5 C6 N2 45.0(2) . . . . ?
C4 C5 C6 C7 -140.6(2) . . . . ?
C5 C6 C7 C8 -174.81(18) . . . . ?
C6 N2 C9 C8 -0.2(2) . . . . ?
C6 N2 C9 C10 -175.85(16) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 N2 0.3(2) . . . . ?
C7 C8 C9 C10 175.41(18) . . . . ?
C8 C9 C10 C11 136.3(2) . . . . ?
C8 C9 C10 C23 16.9(3) . . . . ?
C8 C9 C10 C30 -103.8(2) . . . . ?
C9 N2 C6 C5 175.49(16) . . . . ?
C9 N2 C6 C7 0.0(2) . . . . ?
C9 C10 C11 N3 -45.5(2) . . . . ?
C9 C10 C11 C12 141.0(2) . . . . ?
C9 C10 C30 C31 51.9(2) . . . . ?
C10 C11 C12 C13 174.79(18) . . . . ?
C10 C30 C31 C32 -91.5(2) . . . . ?
C11 N3 C14 C13 0.5(2) . . . . ?
C11 N3 C14 C15 175.09(16) . . . . ?
C11 C10 C30 C31 173.64(16) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 N3 -0.2(2) . . . . ?
C12 C13 C14 C15 -174.12(19) . . . . ?
C13 C14 C15 C16 -136.0(2) . . . . ?
C13 C14 C15 C24 102.8(2) . . . . ?
C13 C14 C15 C25 -15.4(3) . . . . ?
C14 N3 C11 C10 -175.53(16) . . . . ?
C14 N3 C11 C12 -0.7(2) . . . . ?
C14 C15 C16 N4 44.6(2) . . . . ?
C14 C15 C16 C17 -142.0(2) . . . . ?
C15 C16 C17 C18 -174.76(19) . . . . ?
C16 N4 C19 C18 -1.1(2) . . . . ?
C16 N4 C19 C20 -173.33(16) . . . . ?
C16 C17 C18 C19 0.0(2) . . . . ?
C17 C18 C19 N4 0.6(2) . . . . ?
C17 C18 C19 C20 171.90(19) . . . . ?
C18 C19 C20 C1 138.5(2) . . . . ?
C18 C19 C20 C26 18.7(3) . . . . ?
C18 C19 C20 C27 -101.9(2) . . . . ?
C19 N4 C16 C15 175.86(16) . . . . ?
C19 N4 C16 C17 1.1(2) . . . . ?
C19 C20 C27 C28 51.3(2) . . . . ?
C20 C1 C2 C3 175.95(19) . . . . ?
C20 C27 C28 C29 -175.29(18) . . . . ?
C21 C5 C6 N2 166.31(17) . . . . ?
C21 C5 C6 C7 -19.3(3) . . . . ?
C22 C5 C6 N2 -75.4(2) . . . . ?
C22 C5 C6 C7 99.0(2) . . . . ?
C23 C10 C11 N3 74.9(2) . . . . ?
C23 C10 C11 C12 -98.6(2) . . . . ?
C23 C10 C30 C31 -69.0(2) . . . . ?
C24 C15 C16 N4 165.83(17) . . . . ?
C24 C15 C16 C17 -20.8(3) . . . . ?
C25 C15 C16 N4 -75.6(2) . . . . ?
C25 C15 C16 C17 97.8(2) . . . . ?
C26 C20 C27 C28 -69.4(2) . . . . ?
C27 C28 C29 O1 170.4(2) . . . . ?
C30 C10 C11 N3 -166.97(16) . . . . ?
C30 C10 C11 C12 19.5(3) . . . . ?
C30 C31 C32 O2 178.54(16) . . . . ?
O1S C1S C2S C2S -18.5(17) . . . 6_564 ?
C1S O1S C1S C2S 8.2(8) 6_564 . . . ?
C1S O1S C1S C2S 136.1(9) 15_566 . . . ?
C1S O1S C1S C2S -119.7(8) 12_767 . . . ?

# start Validation Reply Form
_vrf_PLAT097_GLOBAL              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.30 eA-3
RESPONSE: The residual electron density is associated with the disordered
solvent molecule. The most sensible model of solvent molecule was applied
which does not match perfectly with the electron density.
The 4:1 THF solvate was supported by 1H NMR analysis of the crystal.
;
_vrf_PLAT420_GLOBAL              
;
PROBLEM: D-H Bond Without Acceptor  O1--H1A . Please Check
RESPONSE: There is no hydrogen bond acceptor atom in the
proximity to O1. Location of H1A is supported by the density difference map.
;
# end Validation Reply Form

_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
;
####################################################################### 
# 
# 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_upm-c01
_database_code_depnum_ccdc_archive 'CCDC 2248775'
loop_
_audit_author_name
_audit_author_address
'Evgeny Bulatov'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-03-15 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H59 N9 O4'
_chemical_formula_weight         898.10

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   10.3501(3)
_cell_length_b                   14.2207(3)
_cell_length_c                   33.7063(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.456(3)
_cell_angle_gamma                90
_cell_volume                     4907.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13447
_cell_measurement_theta_min      1.8740
_cell_measurement_theta_max      25.3070

_exptl_crystal_description       Block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             1912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            52031
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         1.882
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             9711
_reflns_number_gt                6953
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    Sir2019
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'shelXle (Hübschle, Sheldrick and Dittirch, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0790P)²+7.1634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9711
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_ref         0.2188
_refine_ls_wR_factor_gt          0.2049
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_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_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 0.4482(3) 0.7200(2) 0.76573(9) 0.0237(7) Uani 1 1 d . . . . .
O1 O 0.6801(3) 0.5779(2) 0.49745(9) 0.0603(8) Uani 1 1 d . . . . .
N1 N 0.5579(2) 0.66511(17) 0.77554(7) 0.0241(6) Uani 1 1 d . . . . .
H1 H 0.558397 0.604722 0.774223 0.029 Uiso 1 1 calc R U . . .
N2 N 0.8380(2) 0.69572(16) 0.72678(7) 0.0215(5) Uani 1 1 d . . . . .
H2N H 0.806128 0.751679 0.725110 0.026 Uiso 1 1 calc R U . . .
O2 O 1.1158(3) 0.6349(2) 0.50518(8) 0.0517(7) Uani 1 1 d . . . . .
C2 C 0.4890(3) 0.8118(2) 0.77146(9) 0.0268(7) Uani 1 1 d . . . . .
H2 H 0.436566 0.865009 0.767097 0.032 Uiso 1 1 calc R U . . .
N3 N 0.9026(3) 0.6022(2) 0.51121(8) 0.0336(7) Uani 1 1 d . . . . .
O3 O 0.1135(3) 0.5712(2) 0.89531(9) 0.0618(8) Uani 1 1 d . . . . .
C3 C 0.6253(3) 0.8110(2) 0.78518(10) 0.0270(7) Uani 1 1 d . . . . .
H3 H 0.677630 0.863626 0.791386 0.032 Uiso 1 1 calc R U . . .
N4 N 0.6407(2) 0.69450(17) 0.62927(7) 0.0239(6) Uani 1 1 d . . . . .
H4 H 0.637277 0.634778 0.625246 0.029 Uiso 1 1 calc R U . . .
O4 O 0.5524(3) 0.5391(3) 0.89691(10) 0.0685(9) Uani 1 1 d . . . . .
C4 C 0.6668(3) 0.7194(2) 0.78773(9) 0.0223(6) Uani 1 1 d . . . . .
N5 N 0.3668(2) 0.70506(18) 0.68056(7) 0.0252(6) Uani 1 1 d . . . . .
H5 H 0.406910 0.757008 0.687054 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8006(3) 0.6746(2) 0.79862(9) 0.0248(7) Uani 1 1 d . . . . .
C6 C 0.7935(3) 0.5918(2) 0.82756(10) 0.0310(8) Uani 1 1 d . . . . .
H6A H 0.879393 0.566327 0.835323 0.047 Uiso 1 1 calc R U . . .
H6B H 0.737148 0.544002 0.814482 0.047 Uiso 1 1 calc R U . . .
H6C H 0.759568 0.613463 0.850963 0.047 Uiso 1 1 calc R U . . .
N6 N 0.3265(3) 0.5417(2) 0.88724(9) 0.0457(8) Uani 1 1 d . . . . .
C7 C 0.8985(3) 0.7476(2) 0.81958(10) 0.0298(7) Uani 1 1 d . . . . .
H7A H 0.979930 0.717144 0.829091 0.045 Uiso 1 1 calc R U . . .
H7B H 0.863769 0.774991 0.841810 0.045 Uiso 1 1 calc R U . . .
H7C H 0.912537 0.796048 0.800829 0.045 Uiso 1 1 calc R U . . .
C8 C 0.8478(3) 0.6398(2) 0.76054(9) 0.0221(6) Uani 1 1 d . . . . .
C9 C 0.9033(3) 0.5567(2) 0.75117(9) 0.0253(7) Uani 1 1 d . . . . .
H9 H 0.921950 0.505453 0.768193 0.030 Uiso 1 1 calc R U . . .
C10 C 0.9274(3) 0.5629(2) 0.71075(9) 0.0240(7) Uani 1 1 d . . . . .
H10 H 0.964594 0.516287 0.696708 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8862(3) 0.6497(2) 0.69608(9) 0.0214(6) Uani 1 1 d . . . . .
C13 C 0.9074(3) 0.6191(2) 0.62465(9) 0.0234(7) Uani 1 1 d . . . . .
H13A H 0.993660 0.592525 0.632532 0.028 Uiso 1 1 calc R U . . .
H13B H 0.844236 0.569076 0.625758 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8840(3) 0.6960(2) 0.65522(9) 0.0218(6) Uani 1 1 d . . . . .
C14 C 0.8970(3) 0.6536(2) 0.58167(10) 0.0317(8) Uani 1 1 d . . . . .
H14A H 0.960571 0.703084 0.580078 0.038 Uiso 1 1 calc R U . . .
H14B H 0.810668 0.679687 0.573301 0.038 Uiso 1 1 calc R U . . .
C15 C 0.9213(4) 0.5731(2) 0.55360(10) 0.0356(8) Uani 1 1 d . . . . .
H15A H 1.009777 0.550142 0.560999 0.043 Uiso 1 1 calc R U . . .
H15B H 0.861996 0.521799 0.556912 0.043 Uiso 1 1 calc R U . . .
C16 C 0.7806(4) 0.6006(3) 0.48682(11) 0.0403(9) Uani 1 1 d . . . . .
C17 C 0.8074(4) 0.6321(2) 0.44645(11) 0.0388(9) Uani 1 1 d . . . . .
C18 C 0.7226(5) 0.6411(3) 0.41063(12) 0.0524(11) Uani 1 1 d . . . . .
H18 H 0.633371 0.630248 0.409191 0.063 Uiso 1 1 calc R U . . .
C19 C 0.7776(5) 0.6669(3) 0.37720(12) 0.0545(12) Uani 1 1 d . . . . .
H19 H 0.723927 0.673408 0.352689 0.065 Uiso 1 1 calc R U . . .
C1A C 0.5919(3) 0.5115(2) 0.69380(10) 0.0326(8) Uani 1 1 d . . . . .
H1AA H 0.617294 0.465868 0.675436 0.049 Uiso 1 1 calc R U . . .
H1AB H 0.657115 0.559863 0.698311 0.049 Uiso 1 1 calc R U . . .
H1AC H 0.509720 0.538904 0.682667 0.049 Uiso 1 1 calc R U . . .
N1A N 0.5670(3) 0.4321(2) 0.76159(10) 0.0439(8) Uani 1 1 d . . . . .
C20 C 0.9092(5) 0.6833(3) 0.37920(12) 0.0531(12) Uani 1 1 d . . . . .
H20 H 0.942628 0.699813 0.356012 0.064 Uiso 1 1 calc R U . . .
C21 C 0.9939(4) 0.6757(3) 0.41536(12) 0.0477(10) Uani 1 1 d . . . . .
H21 H 1.082868 0.687718 0.416940 0.057 Uiso 1 1 calc R U . . .
C22 C 0.9391(4) 0.6494(2) 0.44865(10) 0.0357(8) Uani 1 1 d . . . . .
C23 C 1.0026(4) 0.6300(2) 0.49091(11) 0.0350(8) Uani 1 1 d . . . . .
C24 C 0.9937(3) 0.7706(2) 0.65787(9) 0.0238(7) Uani 1 1 d . . . . .
H24A H 0.985473 0.805459 0.633233 0.036 Uiso 1 1 calc R U . . .
H24B H 1.077189 0.739950 0.662340 0.036 Uiso 1 1 calc R U . . .
H24C H 0.986446 0.812768 0.679684 0.036 Uiso 1 1 calc R U . . .
C25 C 0.7531(3) 0.7435(2) 0.64315(9) 0.0209(6) Uani 1 1 d . . . . .
C26 C 0.7173(3) 0.8360(2) 0.64563(10) 0.0307(7) Uani 1 1 d . . . . .
H26 H 0.772964 0.885802 0.654014 0.037 Uiso 1 1 calc R U . . .
C27 C 0.5811(3) 0.8422(2) 0.63320(10) 0.0324(8) Uani 1 1 d . . . . .
H27 H 0.531538 0.896966 0.632320 0.039 Uiso 1 1 calc R U . . .
C28 C 0.5342(3) 0.7542(2) 0.62268(9) 0.0257(7) Uani 1 1 d . . . . .
C29 C 0.3976(3) 0.7182(2) 0.60840(10) 0.0301(7) Uani 1 1 d . . . . .
C30 C 0.3971(4) 0.6523(3) 0.57227(10) 0.0434(9) Uani 1 1 d . . . . .
H30A H 0.308765 0.635435 0.561904 0.065 Uiso 1 1 calc R U . . .
H30B H 0.446122 0.596610 0.580530 0.065 Uiso 1 1 calc R U . . .
H30C H 0.436061 0.683811 0.551787 0.065 Uiso 1 1 calc R U . . .
C2A C 0.5791(3) 0.4663(2) 0.73131(11) 0.0316(8) Uani 1 1 d . . . . .
N2A N -0.1090(4) 0.6186(3) 0.99657(13) 0.0720(11) Uani 1 1 d . . . . .
C31 C 0.3051(4) 0.8023(3) 0.59535(11) 0.0419(9) Uani 1 1 d . . . . .
H31A H 0.218344 0.779245 0.586722 0.063 Uiso 1 1 calc R U . . .
H31B H 0.335618 0.835213 0.573665 0.063 Uiso 1 1 calc R U . . .
H31C H 0.304285 0.844248 0.617616 0.063 Uiso 1 1 calc R U . . .
C32 C 0.3480(3) 0.6672(2) 0.64245(9) 0.0261(7) Uani 1 1 d . . . . .
C33 C 0.2796(3) 0.5854(2) 0.64454(10) 0.0295(7) Uani 1 1 d . . . . .
H33 H 0.252455 0.544807 0.623310 0.035 Uiso 1 1 calc R U . . .
C34 C 0.2575(3) 0.5734(2) 0.68474(10) 0.0287(7) Uani 1 1 d . . . . .
H34 H 0.213462 0.523508 0.694521 0.034 Uiso 1 1 calc R U . . .
C35 C 0.3124(3) 0.6483(2) 0.70672(9) 0.0258(7) Uani 1 1 d . . . . .
C36 C 0.3156(3) 0.6780(2) 0.75037(9) 0.0266(7) Uani 1 1 d . . . . .
C37 C 0.2895(3) 0.5896(2) 0.77514(10) 0.0309(7) Uani 1 1 d . . . . .
H37A H 0.202625 0.566030 0.765508 0.037 Uiso 1 1 calc R U . . .
H37B H 0.351599 0.540890 0.770798 0.037 Uiso 1 1 calc R U . . .
C38 C 0.3005(4) 0.6090(2) 0.81966(10) 0.0363(8) Uani 1 1 d . . . . .
H38A H 0.227110 0.647467 0.824594 0.044 Uiso 1 1 calc R U . . .
H38B H 0.379802 0.644318 0.828242 0.044 Uiso 1 1 calc R U . . .
C39 C 0.3026(4) 0.5194(3) 0.84450(11) 0.0473(10) Uani 1 1 d . . . . .
H39A H 0.219605 0.487092 0.838187 0.057 Uiso 1 1 calc R U . . .
H39B H 0.370694 0.477919 0.837895 0.057 Uiso 1 1 calc R U . . .
C40 C 0.2285(4) 0.5695(3) 0.90844(12) 0.0458(10) Uani 1 1 d . . . . .
C3A C -0.1199(4) 0.5681(3) 0.96964(14) 0.0522(10) Uani 1 1 d . . . . .
N3A N 0.3630(3) 0.5337(3) 0.40063(11) 0.0559(9) Uani 1 1 d . . . . .
C41 C 0.2972(4) 0.5973(2) 0.94959(11) 0.0401(9) Uani 1 1 d . . . . .
C42 C 0.2455(5) 0.6263(3) 0.98268(13) 0.0530(11) Uani 1 1 d . . . . .
H42 H 0.155938 0.632275 0.982424 0.064 Uiso 1 1 calc R U . . .
C43 C 0.3358(5) 0.6466(3) 1.01716(12) 0.0517(11) Uani 1 1 d . . . . .
H43 H 0.305358 0.664913 1.040595 0.062 Uiso 1 1 calc R U . . .
C44 C 0.4684(5) 0.6396(3) 1.01673(13) 0.0518(11) Uani 1 1 d . . . . .
H44 H 0.525643 0.654741 1.039781 0.062 Uiso 1 1 calc R U . . .
C45 C 0.5186(5) 0.6107(3) 0.98286(12) 0.0510(11) Uani 1 1 d . . . . .
H45 H 0.608159 0.606175 0.982624 0.061 Uiso 1 1 calc R U . . .
C46 C 0.4291(4) 0.5888(2) 0.94924(11) 0.0428(9) Uani 1 1 d . . . . .
C47 C 0.4531(4) 0.5542(3) 0.90926(12) 0.0454(10) Uani 1 1 d . . . . .
C48 C 0.2081(3) 0.7521(2) 0.75267(10) 0.0312(7) Uani 1 1 d . . . . .
H48A H 0.123895 0.723741 0.745025 0.047 Uiso 1 1 calc R U . . .
H48B H 0.218819 0.803107 0.734795 0.047 Uiso 1 1 calc R U . . .
H48C H 0.214524 0.775451 0.779605 0.047 Uiso 1 1 calc R U . . .
C4A C -0.1325(5) 0.5040(3) 0.93579(13) 0.0581(12) Uani 1 1 d . . . . .
H4AA H -0.222321 0.501059 0.923616 0.087 Uiso 1 1 calc R U . . .
H4AB H -0.103613 0.442496 0.944873 0.087 Uiso 1 1 calc R U . . .
H4AC H -0.080039 0.526079 0.916470 0.087 Uiso 1 1 calc R U . . .
C5A C 0.3720(4) 0.5818(3) 0.42759(12) 0.0462(10) Uani 1 1 d . . . . .
C6A C 0.3847(5) 0.6415(4) 0.46276(15) 0.0722(15) Uani 1 1 d . . . . .
H6AA H 0.398659 0.705307 0.455118 0.108 Uiso 1 1 calc R U . . .
H6AB H 0.457642 0.620853 0.481710 0.108 Uiso 1 1 calc R U . . .
H6AC H 0.306351 0.637882 0.474780 0.108 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
C1 C2 1.378(4) . ?
C1 N1 1.378(4) . ?
C1 C36 1.516(4) . ?
O1 C16 1.194(5) . ?
N1 C4 1.378(4) . ?
N1 H1 0.8600 . ?
N2 C11 1.378(4) . ?
N2 C8 1.380(4) . ?
N2 H2N 0.8600 . ?
O2 C23 1.201(4) . ?
C2 C3 1.418(5) . ?
C2 H2 0.9300 . ?
N3 C23 1.380(5) . ?
N3 C16 1.402(5) . ?
N3 C15 1.472(4) . ?
O3 C40 1.208(5) . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
N4 C25 1.377(4) . ?
N4 C28 1.384(4) . ?
N4 H4 0.8600 . ?
O4 C47 1.184(5) . ?
C4 C5 1.519(4) . ?
N5 C35 1.376(4) . ?
N5 C32 1.380(4) . ?
N5 H5 0.8600 . ?
C5 C8 1.521(4) . ?
C5 C6 1.538(4) . ?
C5 C7 1.547(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N6 C40 1.381(5) . ?
N6 C47 1.419(5) . ?
N6 C39 1.460(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.371(4) . ?
C9 C10 1.423(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.524(4) . ?
C13 C14 1.518(4) . ?
C13 C12 1.546(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 C25 1.516(4) . ?
C12 C24 1.547(4) . ?
C14 C15 1.530(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.497(5) . ?
C17 C22 1.376(5) . ?
C17 C18 1.391(5) . ?
C18 C19 1.385(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(6) . ?
C19 H19 0.9300 . ?
C1A C2A 1.441(5) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
N1A C2A 1.154(4) . ?
C20 C21 1.397(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.504(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.372(4) . ?
C26 C27 1.414(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.514(5) . ?
C29 C32 1.510(5) . ?
C29 C30 1.536(5) . ?
C29 C31 1.554(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
N2A C3A 1.150(6) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.369(5) . ?
C33 C34 1.417(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.371(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.527(4) . ?
C36 C48 1.542(4) . ?
C36 C37 1.555(4) . ?
C37 C38 1.514(5) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.522(5) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.515(5) . ?
C3A C4A 1.451(6) . ?
N3A C5A 1.131(5) . ?
C41 C42 1.370(6) . ?
C41 C46 1.372(6) . ?
C42 C43 1.410(6) . ?
C42 H42 0.9300 . ?
C43 C44 1.378(6) . ?
C43 H43 0.9300 . ?
C44 C45 1.384(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.390(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.489(6) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C4A H4AA 0.9600 . ?
C4A H4AB 0.9600 . ?
C4A H4AC 0.9600 . ?
C5A C6A 1.448(6) . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 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
C2 C1 N1 106.2(3) . . ?
C2 C1 C36 131.7(3) . . ?
N1 C1 C36 122.1(3) . . ?
C4 N1 C1 111.3(2) . . ?
C4 N1 H1 124.3 . . ?
C1 N1 H1 124.3 . . ?
C11 N2 C8 110.8(2) . . ?
C11 N2 H2N 124.6 . . ?
C8 N2 H2N 124.6 . . ?
C1 C2 C3 107.9(3) . . ?
C1 C2 H2 126.1 . . ?
C3 C2 H2 126.1 . . ?
C23 N3 C16 113.0(3) . . ?
C23 N3 C15 124.1(3) . . ?
C16 N3 C15 122.9(3) . . ?
C4 C3 C2 108.5(3) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C25 N4 C28 110.9(3) . . ?
C25 N4 H4 124.5 . . ?
C28 N4 H4 124.5 . . ?
C3 C4 N1 106.1(3) . . ?
C3 C4 C5 132.8(3) . . ?
N1 C4 C5 120.9(3) . . ?
C35 N5 C32 110.7(3) . . ?
C35 N5 H5 124.7 . . ?
C32 N5 H5 124.7 . . ?
C4 C5 C8 109.1(2) . . ?
C4 C5 C6 110.3(3) . . ?
C8 C5 C6 109.7(2) . . ?
C4 C5 C7 110.0(2) . . ?
C8 C5 C7 109.5(3) . . ?
C6 C5 C7 108.3(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C40 N6 C47 112.6(3) . . ?
C40 N6 C39 122.8(3) . . ?
C47 N6 C39 123.5(3) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N2 106.8(3) . . ?
C9 C8 C5 132.2(3) . . ?
N2 C8 C5 121.0(3) . . ?
C8 C9 C10 107.8(3) . . ?
C8 C9 H9 126.1 . . ?
C10 C9 H9 126.1 . . ?
C11 C10 C9 108.1(3) . . ?
C11 C10 H10 125.9 . . ?
C9 C10 H10 125.9 . . ?
C10 C11 N2 106.5(3) . . ?
C10 C11 C12 132.5(3) . . ?
N2 C11 C12 120.9(2) . . ?
C14 C13 C12 114.3(2) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C25 C12 C11 109.2(2) . . ?
C25 C12 C13 111.0(2) . . ?
C11 C12 C13 108.3(2) . . ?
C25 C12 C24 109.2(2) . . ?
C11 C12 C24 109.4(2) . . ?
C13 C12 C24 109.8(2) . . ?
C13 C14 C15 110.6(3) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 C14 112.3(3) . . ?
N3 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
N3 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
O1 C16 N3 125.3(4) . . ?
O1 C16 C17 129.8(4) . . ?
N3 C16 C17 104.9(3) . . ?
C22 C17 C18 121.6(4) . . ?
C22 C17 C16 108.6(3) . . ?
C18 C17 C16 129.7(4) . . ?
C19 C18 C17 116.6(4) . . ?
C19 C18 H18 121.7 . . ?
C17 C18 H18 121.7 . . ?
C20 C19 C18 121.9(4) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C19 C20 C21 121.3(4) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 116.7(4) . . ?
C22 C21 H21 121.6 . . ?
C20 C21 H21 121.6 . . ?
C17 C22 C21 121.8(4) . . ?
C17 C22 C23 108.1(3) . . ?
C21 C22 C23 130.1(4) . . ?
O2 C23 N3 125.2(3) . . ?
O2 C23 C22 129.3(3) . . ?
N3 C23 C22 105.5(3) . . ?
C12 C24 H24A 109.5 . . ?
C12 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C12 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 N4 106.5(3) . . ?
C26 C25 C12 130.5(3) . . ?
N4 C25 C12 122.8(3) . . ?
C25 C26 C27 108.0(3) . . ?
C25 C26 H26 126.0 . . ?
C27 C26 H26 126.0 . . ?
C28 C27 C26 108.6(3) . . ?
C28 C27 H27 125.7 . . ?
C26 C27 H27 125.7 . . ?
C27 C28 N4 106.0(3) . . ?
C27 C28 C29 132.1(3) . . ?
N4 C28 C29 121.9(3) . . ?
C32 C29 C28 109.1(3) . . ?
C32 C29 C30 110.4(3) . . ?
C28 C29 C30 110.6(3) . . ?
C32 C29 C31 108.7(3) . . ?
C28 C29 C31 109.7(3) . . ?
C30 C29 C31 108.3(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N1A C2A C1A 178.3(4) . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 N5 106.7(3) . . ?
C33 C32 C29 133.1(3) . . ?
N5 C32 C29 120.2(3) . . ?
C32 C33 C34 108.0(3) . . ?
C32 C33 H33 126.0 . . ?
C34 C33 H33 126.0 . . ?
C35 C34 C33 108.1(3) . . ?
C35 C34 H34 125.9 . . ?
C33 C34 H34 125.9 . . ?
C34 C35 N5 106.6(3) . . ?
C34 C35 C36 133.2(3) . . ?
N5 C35 C36 120.1(3) . . ?
C1 C36 C35 109.2(3) . . ?
C1 C36 C48 109.8(3) . . ?
C35 C36 C48 108.9(3) . . ?
C1 C36 C37 110.8(3) . . ?
C35 C36 C37 108.2(3) . . ?
C48 C36 C37 110.0(3) . . ?
C38 C37 C36 113.0(3) . . ?
C38 C37 H37A 109.0 . . ?
C36 C37 H37A 109.0 . . ?
C38 C37 H37B 109.0 . . ?
C36 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
C37 C38 C39 112.7(3) . . ?
C37 C38 H38A 109.1 . . ?
C39 C38 H38A 109.1 . . ?
C37 C38 H38B 109.1 . . ?
C39 C38 H38B 109.1 . . ?
H38A C38 H38B 107.8 . . ?
N6 C39 C38 110.4(3) . . ?
N6 C39 H39A 109.6 . . ?
C38 C39 H39A 109.6 . . ?
N6 C39 H39B 109.6 . . ?
C38 C39 H39B 109.6 . . ?
H39A C39 H39B 108.1 . . ?
O3 C40 N6 125.1(4) . . ?
O3 C40 C41 129.4(4) . . ?
N6 C40 C41 105.5(3) . . ?
N2A C3A C4A 179.5(5) . . ?
C42 C41 C46 122.8(4) . . ?
C42 C41 C40 129.6(4) . . ?
C46 C41 C40 107.6(3) . . ?
C41 C42 C43 116.2(4) . . ?
C41 C42 H42 121.9 . . ?
C43 C42 H42 121.9 . . ?
C44 C43 C42 121.2(4) . . ?
C44 C43 H43 119.4 . . ?
C42 C43 H43 119.4 . . ?
C43 C44 C45 121.7(4) . . ?
C43 C44 H44 119.2 . . ?
C45 C44 H44 119.2 . . ?
C44 C45 C46 116.9(4) . . ?
C44 C45 H45 121.5 . . ?
C46 C45 H45 121.5 . . ?
C41 C46 C45 121.2(4) . . ?
C41 C46 C47 109.6(3) . . ?
C45 C46 C47 129.2(4) . . ?
O4 C47 N6 125.2(4) . . ?
O4 C47 C46 130.3(4) . . ?
N6 C47 C46 104.5(4) . . ?
C36 C48 H48A 109.5 . . ?
C36 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C36 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C3A C4A H4AA 109.5 . . ?
C3A C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
C3A C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
N3A C5A C6A 178.5(5) . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 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
C2 C1 N1 C4 0.7(3) . . . . ?
C36 C1 N1 C4 178.4(3) . . . . ?
N1 C1 C2 C3 -0.4(3) . . . . ?
C36 C1 C2 C3 -177.9(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 N1 0.4(3) . . . . ?
C2 C3 C4 C5 176.9(3) . . . . ?
C1 N1 C4 C3 -0.6(3) . . . . ?
C1 N1 C4 C5 -177.7(3) . . . . ?
C3 C4 C5 C8 -104.2(4) . . . . ?
N1 C4 C5 C8 71.9(3) . . . . ?
C3 C4 C5 C6 135.2(4) . . . . ?
N1 C4 C5 C6 -48.7(4) . . . . ?
C3 C4 C5 C7 15.8(5) . . . . ?
N1 C4 C5 C7 -168.0(3) . . . . ?
C11 N2 C8 C9 0.1(3) . . . . ?
C11 N2 C8 C5 -179.8(3) . . . . ?
C4 C5 C8 C9 -133.8(3) . . . . ?
C6 C5 C8 C9 -12.8(5) . . . . ?
C7 C5 C8 C9 105.9(4) . . . . ?
C4 C5 C8 N2 46.0(4) . . . . ?
C6 C5 C8 N2 167.0(3) . . . . ?
C7 C5 C8 N2 -74.3(3) . . . . ?
N2 C8 C9 C10 0.0(3) . . . . ?
C5 C8 C9 C10 179.8(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 N2 0.0(3) . . . . ?
C9 C10 C11 C12 -178.7(3) . . . . ?
C8 N2 C11 C10 -0.1(3) . . . . ?
C8 N2 C11 C12 178.9(2) . . . . ?
C10 C11 C12 C25 135.1(3) . . . . ?
N2 C11 C12 C25 -43.5(4) . . . . ?
C10 C11 C12 C13 14.2(4) . . . . ?
N2 C11 C12 C13 -164.4(3) . . . . ?
C10 C11 C12 C24 -105.4(4) . . . . ?
N2 C11 C12 C24 76.0(3) . . . . ?
C14 C13 C12 C25 55.5(3) . . . . ?
C14 C13 C12 C11 175.3(3) . . . . ?
C14 C13 C12 C24 -65.4(3) . . . . ?
C12 C13 C14 C15 -179.9(3) . . . . ?
C23 N3 C15 C14 96.1(4) . . . . ?
C16 N3 C15 C14 -86.5(4) . . . . ?
C13 C14 C15 N3 175.8(3) . . . . ?
C23 N3 C16 O1 179.0(4) . . . . ?
C15 N3 C16 O1 1.4(6) . . . . ?
C23 N3 C16 C17 -0.6(4) . . . . ?
C15 N3 C16 C17 -178.2(3) . . . . ?
O1 C16 C17 C22 -179.1(4) . . . . ?
N3 C16 C17 C22 0.5(4) . . . . ?
O1 C16 C17 C18 -1.6(7) . . . . ?
N3 C16 C17 C18 177.9(4) . . . . ?
C22 C17 C18 C19 0.9(6) . . . . ?
C16 C17 C18 C19 -176.3(4) . . . . ?
C17 C18 C19 C20 -0.2(6) . . . . ?
C18 C19 C20 C21 -0.8(6) . . . . ?
C19 C20 C21 C22 1.1(6) . . . . ?
C18 C17 C22 C21 -0.6(5) . . . . ?
C16 C17 C22 C21 177.1(3) . . . . ?
C18 C17 C22 C23 -178.0(3) . . . . ?
C16 C17 C22 C23 -0.3(4) . . . . ?
C20 C21 C22 C17 -0.4(5) . . . . ?
C20 C21 C22 C23 176.3(3) . . . . ?
C16 N3 C23 O2 -178.4(3) . . . . ?
C15 N3 C23 O2 -0.8(5) . . . . ?
C16 N3 C23 C22 0.4(4) . . . . ?
C15 N3 C23 C22 178.0(3) . . . . ?
C17 C22 C23 O2 178.7(4) . . . . ?
C21 C22 C23 O2 1.6(6) . . . . ?
C17 C22 C23 N3 -0.1(4) . . . . ?
C21 C22 C23 N3 -177.1(3) . . . . ?
C28 N4 C25 C26 0.3(3) . . . . ?
C28 N4 C25 C12 176.5(3) . . . . ?
C11 C12 C25 C26 99.1(4) . . . . ?
C13 C12 C25 C26 -141.6(3) . . . . ?
C24 C12 C25 C26 -20.4(4) . . . . ?
C11 C12 C25 N4 -76.1(3) . . . . ?
C13 C12 C25 N4 43.2(4) . . . . ?
C24 C12 C25 N4 164.4(3) . . . . ?
N4 C25 C26 C27 0.3(4) . . . . ?
C12 C25 C26 C27 -175.5(3) . . . . ?
C25 C26 C27 C28 -0.8(4) . . . . ?
C26 C27 C28 N4 1.0(4) . . . . ?
C26 C27 C28 C29 178.1(3) . . . . ?
C25 N4 C28 C27 -0.8(3) . . . . ?
C25 N4 C28 C29 -178.3(3) . . . . ?
C27 C28 C29 C32 -104.0(4) . . . . ?
N4 C28 C29 C32 72.8(4) . . . . ?
C27 C28 C29 C30 134.4(4) . . . . ?
N4 C28 C29 C30 -48.8(4) . . . . ?
C27 C28 C29 C31 14.9(5) . . . . ?
N4 C28 C29 C31 -168.3(3) . . . . ?
C35 N5 C32 C33 0.5(3) . . . . ?
C35 N5 C32 C29 179.0(3) . . . . ?
C28 C29 C32 C33 -138.1(4) . . . . ?
C30 C29 C32 C33 -16.3(5) . . . . ?
C31 C29 C32 C33 102.3(4) . . . . ?
C28 C29 C32 N5 43.8(4) . . . . ?
C30 C29 C32 N5 165.6(3) . . . . ?
C31 C29 C32 N5 -75.8(4) . . . . ?
N5 C32 C33 C34 -0.4(3) . . . . ?
C29 C32 C33 C34 -178.7(3) . . . . ?
C32 C33 C34 C35 0.2(4) . . . . ?
C33 C34 C35 N5 0.1(3) . . . . ?
C33 C34 C35 C36 176.4(3) . . . . ?
C32 N5 C35 C34 -0.4(3) . . . . ?
C32 N5 C35 C36 -177.3(3) . . . . ?
C2 C1 C36 C35 101.6(4) . . . . ?
N1 C1 C36 C35 -75.5(3) . . . . ?
C2 C1 C36 C48 -17.7(5) . . . . ?
N1 C1 C36 C48 165.2(3) . . . . ?
C2 C1 C36 C37 -139.3(3) . . . . ?
N1 C1 C36 C37 43.6(4) . . . . ?
C34 C35 C36 C1 142.6(3) . . . . ?
N5 C35 C36 C1 -41.5(4) . . . . ?
C34 C35 C36 C48 -97.5(4) . . . . ?
N5 C35 C36 C48 78.4(3) . . . . ?
C34 C35 C36 C37 22.0(5) . . . . ?
N5 C35 C36 C37 -162.1(3) . . . . ?
C1 C36 C37 C38 56.0(4) . . . . ?
C35 C36 C37 C38 175.7(3) . . . . ?
C48 C36 C37 C38 -65.5(4) . . . . ?
C36 C37 C38 C39 -168.3(3) . . . . ?
C40 N6 C39 C38 83.0(4) . . . . ?
C47 N6 C39 C38 -84.7(4) . . . . ?
C37 C38 C39 N6 174.3(3) . . . . ?
C47 N6 C40 O3 175.2(4) . . . . ?
C39 N6 C40 O3 6.2(6) . . . . ?
C47 N6 C40 C41 -3.9(4) . . . . ?
C39 N6 C40 C41 -172.9(3) . . . . ?
O3 C40 C41 C42 4.0(7) . . . . ?
N6 C40 C41 C42 -176.9(4) . . . . ?
O3 C40 C41 C46 -176.0(4) . . . . ?
N6 C40 C41 C46 3.0(4) . . . . ?
C46 C41 C42 C43 -0.6(6) . . . . ?
C40 C41 C42 C43 179.4(4) . . . . ?
C41 C42 C43 C44 1.7(6) . . . . ?
C42 C43 C44 C45 -1.4(6) . . . . ?
C43 C44 C45 C46 -0.1(6) . . . . ?
C42 C41 C46 C45 -0.9(6) . . . . ?
C40 C41 C46 C45 179.2(3) . . . . ?
C42 C41 C46 C47 178.9(3) . . . . ?
C40 C41 C46 C47 -1.1(4) . . . . ?
C44 C45 C46 C41 1.2(5) . . . . ?
C44 C45 C46 C47 -178.5(4) . . . . ?
C40 N6 C47 O4 -176.8(4) . . . . ?
C39 N6 C47 O4 -8.0(6) . . . . ?
C40 N6 C47 C46 3.3(4) . . . . ?
C39 N6 C47 C46 172.1(3) . . . . ?
C41 C46 C47 O4 178.9(4) . . . . ?
C45 C46 C47 O4 -1.4(7) . . . . ?
C41 C46 C47 N6 -1.2(4) . . . . ?
C45 C46 C47 N6 178.5(4) . . . . ?

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.064

