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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_IBS_A_114K_WET
_database_code_depnum_ccdc_archive 'CCDC 1999410'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2023-06-05 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2020-04-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_PLAT029_IBS_A_114K_WET      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.935 Why?  
RESPONSE: This slight defect must be due to the tiny size and high aspect
          ratio of the measured crystal. Also, no strong scatterer was 
          present in this compound.		  
;
_chemical_name_common            SR47436-A
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 N6 O, 1[H2O]'
_chemical_formula_sum            'C25 H28 N6 O'
_chemical_formula_weight         428.53
_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   37.2565(10)
_cell_length_b                   37.2565(10)
_cell_length_c                   9.6925(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11651.2(7)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    114(2)
_cell_measurement_theta_max      66.242
_cell_measurement_theta_min      2.372
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.808
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V2012/1 (Bruker AXS Inc.) was used for absorption correction.
wR2(int) was 0.1579 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.867.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             4104
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            35318
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.182
_diffrn_reflns_theta_max         67.182
_diffrn_reflns_theta_min         2.372
_diffrn_ambient_temperature      114.0
_diffrn_detector_area_resol_mean 8.3333
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX_DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3641
_reflns_number_total             4329
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2016.5.0.1'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4329
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.051
_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)+(0.0652P)²+11.2591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1241
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2T1-C1 \\sim C2T2-C1 \\sim C2T1-C3T1 \\sim C2T2-C3T2 \\sim C4T1-C3T1 \\sim
C4T2-C3T2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2T1 \\sim C2T2 \\sim C3T1 \\sim C3T2 \\sim C4T1 \\sim C4T2: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(H1BC)=Sof(H1BD)=Sof(C2T2)=Sof(H2TC)=Sof(H2TD)=Sof(C3T2)=Sof(H3TC)=
 Sof(H3TD)=Sof(C4T2)=Sof(H4TD)=Sof(H4TE)=Sof(H4TF)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C2T1)=Sof(H2TA)=Sof(H2TB)=Sof(C3T1)=Sof(H3TA)=
 Sof(H3TB)=Sof(C4T1)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=FVAR(1)
 Sof(H1N)=1-FVAR(2)
 Sof(H1)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1M(H1MA,H1MB), C2T1(H2TA,H2TB), C2T2(H2TC,
 H2TD), C3T1(H3TA,H3TB), C3T2(H3TC,H3TD), C6N(H6NA,H6NB), C7N(H7NA,H7NB),
 C8N(H8NA,H8NB), C9N(H9NA,H9NB)
5.b Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C3P(H3P), C4P(H4P), C5B(H5B), C5P(H5P), C6B(H6B), C6P(H6P)
5.c Idealised Me refined as rotating group:
 C4T1(H4TA,H4TB,H4TC), C4T2(H4TD,H4TE,H4TF)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O1N O 0.63793(4) 0.72516(4) -0.19427(13) 0.0371(3) Uani 1 1 d . . . . .
N1 N 0.57303(4) 0.48364(4) 0.01409(16) 0.0281(3) Uani 1 1 d . . . . .
H1 H 0.5838(7) 0.4957(7) -0.073(3) 0.034 Uiso 0.82(3) 1 d . U P A 1
N1N N 0.58196(4) 0.73156(4) 0.09157(16) 0.0304(3) Uani 1 1 d . . . . .
H1N H 0.570(3) 0.741(3) 0.145(13) 0.036 Uiso 0.18(3) 1 d . U P A 2
N2 N 0.53412(4) 0.45100(4) 0.02019(16) 0.0313(3) Uani 1 1 d . . . . .
N3 N 0.52841(4) 0.43741(4) 0.14590(16) 0.0333(4) Uani 1 1 d . . . . .
N3N N 0.58298(4) 0.68430(4) -0.04969(14) 0.0271(3) Uani 1 1 d . . . . .
N4 N 0.56296(4) 0.46040(4) 0.22341(15) 0.0324(3) Uani 1 1 d . . . . .
C1 C 0.52757(5) 0.65997(5) 0.13358(19) 0.0345(4) Uani 1 1 d D U . . .
H1AA H 0.526739 0.669119 0.228830 0.041 Uiso 0.940(3) 1 calc R U P B 1
H1AB H 0.529499 0.634452 0.139383 0.041 Uiso 0.940(3) 1 calc R U P B 1
H1BC H 0.538008 0.652511 0.216367 0.041 Uiso 0.060(3) 1 calc R U P B 2
H1BD H 0.516115 0.635490 0.072061 0.041 Uiso 0.060(3) 1 calc R U P B 2
C1B C 0.63312(5) 0.58276(5) 0.08186(17) 0.0262(4) Uani 1 1 d . . . . .
C1M C 0.57258(5) 0.64373(5) -0.10740(18) 0.0291(4) Uani 1 1 d . . . . .
H1MA H 0.579915 0.647190 -0.206572 0.035 Uiso 1 1 calc R U . . .
H1MB H 0.542260 0.624923 -0.100220 0.035 Uiso 1 1 calc R U . . .
C1P C 0.65407(5) 0.56151(5) 0.14449(17) 0.0271(4) Uani 1 1 d . . . . .
C2B C 0.65312(5) 0.61328(5) -0.01799(18) 0.0290(4) Uani 1 1 d . . . . .
H2B H 0.680220 0.620296 -0.046906 0.035 Uiso 1 1 calc R U . . .
C2N C 0.56488(5) 0.69277(5) 0.06207(18) 0.0285(4) Uani 1 1 d . . . . .
C2P C 0.63372(5) 0.51887(5) 0.17626(17) 0.0283(4) Uani 1 1 d . . . . .
C2T1 C 0.48774(6) 0.65028(6) 0.0591(2) 0.0406(5) Uani 0.940(3) 1 d D U P B 1
H2TA H 0.487079 0.637949 -0.032052 0.049 Uiso 0.940(3) 1 calc R U P B 1
H2TB H 0.487477 0.676395 0.043151 0.049 Uiso 0.940(3) 1 calc R U P B 1
C2T2 C 0.4908(6) 0.6634(8) 0.182(4) 0.045(4) Uani 0.060(3) 1 d D U P B 2
H2TC H 0.479417 0.670994 0.101989 0.054 Uiso 0.060(3) 1 calc R U P B 2
H2TD H 0.500583 0.686200 0.249822 0.054 Uiso 0.060(3) 1 calc R U P B 2
C3B C 0.63419(5) 0.63362(5) -0.07601(18) 0.0294(4) Uani 1 1 d . . . . .
H3B H 0.648588 0.654563 -0.143227 0.035 Uiso 1 1 calc R U . . .
C3P C 0.65516(5) 0.50194(5) 0.24164(19) 0.0346(4) Uani 1 1 d . . . . .
H3P H 0.640957 0.473333 0.264828 0.042 Uiso 1 1 calc R U . . .
C3T1 C 0.44925(6) 0.62050(7) 0.1405(3) 0.0530(7) Uani 0.940(3) 1 d D U P B 1
H3TA H 0.451206 0.595827 0.166299 0.064 Uiso 0.940(3) 1 calc R U P B 1
H3TB H 0.448152 0.634205 0.226585 0.064 Uiso 0.940(3) 1 calc R U P B 1
C3T2 C 0.4559(9) 0.6244(8) 0.247(4) 0.049(5) Uani 0.060(3) 1 d D U P B 2
H3TC H 0.467822 0.612897 0.313124 0.059 Uiso 0.060(3) 1 calc R U P B 2
H3TD H 0.441290 0.603397 0.174389 0.059 Uiso 0.060(3) 1 calc R U P B 2
C4B C 0.59432(5) 0.62369(5) -0.03685(18) 0.0272(4) Uani 1 1 d . . . . .
C4N C 0.61518(5) 0.72126(5) -0.09838(18) 0.0290(4) Uani 1 1 d . . . . .
C4P C 0.69671(5) 0.52606(6) 0.2733(2) 0.0371(4) Uani 1 1 d . . . . .
H4P H 0.710955 0.514169 0.318201 0.044 Uiso 1 1 calc R U . . .
C4T1 C 0.40953(7) 0.60669(9) 0.0590(4) 0.0821(10) Uani 0.940(3) 1 d D U P B 1
H4TA H 0.385725 0.586890 0.113952 0.123 Uiso 0.940(3) 1 calc R U P B 1
H4TB H 0.410626 0.593446 -0.027035 0.123 Uiso 0.940(3) 1 calc R U P B 1
H4TC H 0.406665 0.630847 0.037570 0.123 Uiso 0.940(3) 1 calc R U P B 1
C4T2 C 0.4248(11) 0.6325(12) 0.323(5) 0.067(10) Uani 0.060(3) 1 d D U P B 2
H4TD H 0.439603 0.658602 0.373585 0.100 Uiso 0.060(3) 1 calc R U P B 2
H4TE H 0.408703 0.609735 0.387090 0.100 Uiso 0.060(3) 1 calc R U P B 2
H4TF H 0.406076 0.634251 0.255454 0.100 Uiso 0.060(3) 1 calc R U P B 2
C5 C 0.59031(5) 0.48893(5) 0.13915(17) 0.0269(4) Uani 1 1 d . . . . .
C5B C 0.57438(5) 0.59347(5) 0.06418(18) 0.0278(4) Uani 1 1 d . . . . .
H5B H 0.547191 0.586318 0.092434 0.033 Uiso 1 1 calc R U . . .
C5N C 0.61530(5) 0.75460(5) -0.00905(17) 0.0275(4) Uani 1 1 d . . . . .
C5P C 0.71740(5) 0.56766(5) 0.23908(18) 0.0328(4) Uani 1 1 d . . . . .
H5P H 0.746138 0.584319 0.258464 0.039 Uiso 1 1 calc R U . . .
C6B C 0.59356(5) 0.57369(5) 0.12403(17) 0.0271(4) Uani 1 1 d . . . . .
H6B H 0.579694 0.553738 0.194541 0.033 Uiso 1 1 calc R U . . .
C6N C 0.60752(5) 0.78541(5) -0.09032(19) 0.0317(4) Uani 1 1 d . . . . .
H6NA H 0.623855 0.793906 -0.176782 0.038 Uiso 1 1 calc R U . . .
H6NB H 0.577778 0.773210 -0.113167 0.038 Uiso 1 1 calc R U . . .
C6P C 0.69627(5) 0.58506(5) 0.17657(17) 0.0295(4) Uani 1 1 d . . . . .
H6P H 0.710814 0.613776 0.154879 0.035 Uiso 1 1 calc R U . . .
C7N C 0.62179(5) 0.82220(5) 0.00802(19) 0.0334(4) Uani 1 1 d . . . . .
H7NA H 0.598811 0.818256 0.069199 0.040 Uiso 1 1 calc R U . . .
H7NB H 0.631664 0.848301 -0.044295 0.040 Uiso 1 1 calc R U . . .
C8N C 0.65730(5) 0.82338(5) 0.09254(19) 0.0316(4) Uani 1 1 d . . . . .
H8NA H 0.684170 0.847541 0.065508 0.038 Uiso 1 1 calc R U . . .
H8NB H 0.652898 0.825415 0.192301 0.038 Uiso 1 1 calc R U . . .
C9N C 0.65695(5) 0.78294(5) 0.0611(2) 0.0348(4) Uani 1 1 d . . . . .
H9NA H 0.659516 0.770133 0.147318 0.042 Uiso 1 1 calc R U . . .
H9NB H 0.680195 0.788158 -0.000831 0.042 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
O1N C4N 1.217(2) . ?
N1 H1 0.94(3) . ?
N1 N2 1.3494(18) . ?
N1 C5 1.340(2) . ?
N1N H1N 0.86(12) . ?
N1N C2N 1.287(2) . ?
N1N C5N 1.471(2) . ?
N2 N3 1.296(2) . ?
N3 N4 1.361(2) . ?
N3N C1M 1.470(2) . ?
N3N C2N 1.393(2) . ?
N3N C4N 1.381(2) . ?
N4 C5 1.324(2) . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 C2N 1.486(2) . ?
C1 C2T1 1.523(3) . ?
C1 C2T2 1.513(8) . ?
C1B C1P 1.491(2) . ?
C1B C2B 1.392(2) . ?
C1B C6B 1.398(2) . ?
C1M H1MA 0.9900 . ?
C1M H1MB 0.9900 . ?
C1M C4B 1.512(2) . ?
C1P C2P 1.410(2) . ?
C1P C6P 1.400(2) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.386(2) . ?
C2P C3P 1.393(2) . ?
C2P C5 1.478(2) . ?
C2T1 H2TA 0.9900 . ?
C2T1 H2TB 0.9900 . ?
C2T1 C3T1 1.523(3) . ?
C2T2 H2TC 0.9900 . ?
C2T2 H2TD 0.9900 . ?
C2T2 C3T2 1.520(8) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.392(2) . ?
C3P H3P 0.9500 . ?
C3P C4P 1.381(2) . ?
C3T1 H3TA 0.9900 . ?
C3T1 H3TB 0.9900 . ?
C3T1 C4T1 1.522(3) . ?
C3T2 H3TC 0.9900 . ?
C3T2 H3TD 0.9900 . ?
C3T2 C4T2 1.520(8) . ?
C4B C5B 1.394(2) . ?
C4N C5N 1.512(2) . ?
C4P H4P 0.9500 . ?
C4P C5P 1.383(3) . ?
C4T1 H4TA 0.9800 . ?
C4T1 H4TB 0.9800 . ?
C4T1 H4TC 0.9800 . ?
C4T2 H4TD 0.9800 . ?
C4T2 H4TE 0.9800 . ?
C4T2 H4TF 0.9800 . ?
C5B H5B 0.9500 . ?
C5B C6B 1.384(2) . ?
C5N C6N 1.534(2) . ?
C5N C9N 1.532(2) . ?
C5P H5P 0.9500 . ?
C5P C6P 1.385(2) . ?
C6B H6B 0.9500 . ?
C6N H6NA 0.9900 . ?
C6N H6NB 0.9900 . ?
C6N C7N 1.530(2) . ?
C6P H6P 0.9500 . ?
C7N H7NA 0.9900 . ?
C7N H7NB 0.9900 . ?
C7N C8N 1.538(2) . ?
C8N H8NA 0.9900 . ?
C8N H8NB 0.9900 . ?
C8N C9N 1.531(2) . ?
C9N H9NA 0.9900 . ?
C9N H9NB 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
N2 N1 H1 118.6(14) . . ?
C5 N1 H1 132.6(14) . . ?
C5 N1 N2 108.28(14) . . ?
C2N N1N H1N 122(7) . . ?
C2N N1N C5N 107.90(14) . . ?
C5N N1N H1N 128(7) . . ?
N3 N2 N1 106.61(13) . . ?
N2 N3 N4 110.75(13) . . ?
C2N N3N C1M 128.32(13) . . ?
C4N N3N C1M 123.11(14) . . ?
C4N N3N C2N 108.51(13) . . ?
C5 N4 N3 105.73(14) . . ?
H1AA C1 H1AB 107.9 . . ?
H1BC C1 H1BD 106.2 . . ?
C2N C1 H1AA 109.2 . . ?
C2N C1 H1AB 109.2 . . ?
C2N C1 H1BC 105.8 . . ?
C2N C1 H1BD 105.8 . . ?
C2N C1 C2T1 111.94(15) . . ?
C2N C1 C2T2 126.2(9) . . ?
C2T1 C1 H1AA 109.2 . . ?
C2T1 C1 H1AB 109.2 . . ?
C2T2 C1 H1BC 105.8 . . ?
C2T2 C1 H1BD 105.8 . . ?
C2B C1B C1P 120.55(14) . . ?
C2B C1B C6B 118.01(15) . . ?
C6B C1B C1P 121.41(15) . . ?
N3N C1M H1MA 108.8 . . ?
N3N C1M H1MB 108.8 . . ?
N3N C1M C4B 113.87(13) . . ?
H1MA C1M H1MB 107.7 . . ?
C4B C1M H1MA 108.8 . . ?
C4B C1M H1MB 108.8 . . ?
C2P C1P C1B 123.90(14) . . ?
C6P C1P C1B 118.67(14) . . ?
C6P C1P C2P 117.41(15) . . ?
C1B C2B H2B 119.4 . . ?
C3B C2B C1B 121.18(15) . . ?
C3B C2B H2B 119.4 . . ?
N1N C2N N3N 113.80(15) . . ?
N1N C2N C1 123.66(16) . . ?
N3N C2N C1 122.42(14) . . ?
C1P C2P C5 124.47(15) . . ?
C3P C2P C1P 120.15(15) . . ?
C3P C2P C5 115.32(14) . . ?
C1 C2T1 H2TA 109.2 . . ?
C1 C2T1 H2TB 109.2 . . ?
C1 C2T1 C3T1 112.21(18) . . ?
H2TA C2T1 H2TB 107.9 . . ?
C3T1 C2T1 H2TA 109.2 . . ?
C3T1 C2T1 H2TB 109.2 . . ?
C1 C2T2 H2TC 108.5 . . ?
C1 C2T2 H2TD 108.5 . . ?
C1 C2T2 C3T2 115.3(16) . . ?
H2TC C2T2 H2TD 107.5 . . ?
C3T2 C2T2 H2TC 108.5 . . ?
C3T2 C2T2 H2TD 108.5 . . ?
C2B C3B H3B 119.6 . . ?
C2B C3B C4B 120.73(16) . . ?
C4B C3B H3B 119.6 . . ?
C2P C3P H3P 119.5 . . ?
C4P C3P C2P 121.09(16) . . ?
C4P C3P H3P 119.5 . . ?
C2T1 C3T1 H3TA 109.1 . . ?
C2T1 C3T1 H3TB 109.1 . . ?
H3TA C3T1 H3TB 107.9 . . ?
C4T1 C3T1 C2T1 112.3(2) . . ?
C4T1 C3T1 H3TA 109.1 . . ?
C4T1 C3T1 H3TB 109.1 . . ?
C2T2 C3T2 H3TC 109.1 . . ?
C2T2 C3T2 H3TD 109.1 . . ?
C2T2 C3T2 C4T2 113(2) . . ?
H3TC C3T2 H3TD 107.8 . . ?
C4T2 C3T2 H3TC 109.1 . . ?
C4T2 C3T2 H3TD 109.1 . . ?
C3B C4B C1M 120.63(15) . . ?
C3B C4B C5B 118.24(15) . . ?
C5B C4B C1M 121.06(14) . . ?
O1N C4N N3N 125.88(15) . . ?
O1N C4N C5N 128.59(15) . . ?
N3N C4N C5N 105.53(14) . . ?
C3P C4P H4P 120.3 . . ?
C3P C4P C5P 119.43(16) . . ?
C5P C4P H4P 120.3 . . ?
C3T1 C4T1 H4TA 109.5 . . ?
C3T1 C4T1 H4TB 109.5 . . ?
C3T1 C4T1 H4TC 109.5 . . ?
H4TA C4T1 H4TB 109.5 . . ?
H4TA C4T1 H4TC 109.5 . . ?
H4TB C4T1 H4TC 109.5 . . ?
C3T2 C4T2 H4TD 109.5 . . ?
C3T2 C4T2 H4TE 109.5 . . ?
C3T2 C4T2 H4TF 109.5 . . ?
H4TD C4T2 H4TE 109.5 . . ?
H4TD C4T2 H4TF 109.5 . . ?
H4TE C4T2 H4TF 109.5 . . ?
N1 C5 C2P 126.52(15) . . ?
N4 C5 N1 108.63(14) . . ?
N4 C5 C2P 124.64(15) . . ?
C4B C5B H5B 119.5 . . ?
C6B C5B C4B 121.07(15) . . ?
C6B C5B H5B 119.5 . . ?
N1N C5N C4N 104.20(13) . . ?
N1N C5N C6N 110.91(13) . . ?
N1N C5N C9N 112.12(14) . . ?
C4N C5N C6N 113.35(14) . . ?
C4N C5N C9N 113.96(13) . . ?
C9N C5N C6N 102.56(13) . . ?
C4P C5P H5P 120.0 . . ?
C4P C5P C6P 120.07(15) . . ?
C6P C5P H5P 120.0 . . ?
C1B C6B H6B 119.6 . . ?
C5B C6B C1B 120.73(15) . . ?
C5B C6B H6B 119.6 . . ?
C5N C6N H6NA 111.0 . . ?
C5N C6N H6NB 111.0 . . ?
H6NA C6N H6NB 109.0 . . ?
C7N C6N C5N 103.86(14) . . ?
C7N C6N H6NA 111.0 . . ?
C7N C6N H6NB 111.0 . . ?
C1P C6P H6P 119.1 . . ?
C5P C6P C1P 121.80(15) . . ?
C5P C6P H6P 119.1 . . ?
C6N C7N H7NA 110.7 . . ?
C6N C7N H7NB 110.7 . . ?
C6N C7N C8N 105.41(13) . . ?
H7NA C7N H7NB 108.8 . . ?
C8N C7N H7NA 110.7 . . ?
C8N C7N H7NB 110.7 . . ?
C7N C8N H8NA 110.4 . . ?
C7N C8N H8NB 110.4 . . ?
H8NA C8N H8NB 108.6 . . ?
C9N C8N C7N 106.40(13) . . ?
C9N C8N H8NA 110.4 . . ?
C9N C8N H8NB 110.4 . . ?
C5N C9N H9NA 110.6 . . ?
C5N C9N H9NB 110.6 . . ?
C8N C9N C5N 105.88(13) . . ?
C8N C9N H9NA 110.6 . . ?
C8N C9N H9NB 110.6 . . ?
H9NA C9N H9NB 108.7 . . ?

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 N1N 0.94(3) 1.80(3) 2.741(2) 177(2) 8_654 yes
N1N H1N N1 0.86(12) 2.06(13) 2.741(2) 136(10) 6_565 yes
C1M H1MB N3 0.99 2.53 3.473(2) 158.8 10_665 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
O1N C4N C5N N1N -178.32(16) . . . . ?
O1N C4N C5N C6N 61.0(2) . . . . ?
O1N C4N C5N C9N -55.8(2) . . . . ?
N1 N2 N3 N4 -0.18(17) . . . . ?
N1N C5N C6N C7N 79.72(16) . . . . ?
N1N C5N C9N C8N -85.42(17) . . . . ?
N2 N1 C5 N4 -0.28(17) . . . . ?
N2 N1 C5 C2P 174.62(15) . . . . ?
N2 N3 N4 C5 0.01(18) . . . . ?
N3 N4 C5 N1 0.16(17) . . . . ?
N3 N4 C5 C2P -174.85(15) . . . . ?
N3N C1M C4B C3B -84.65(19) . . . . ?
N3N C1M C4B C5B 98.41(17) . . . . ?
N3N C4N C5N N1N 2.29(16) . . . . ?
N3N C4N C5N C6N -118.39(15) . . . . ?
N3N C4N C5N C9N 124.80(15) . . . . ?
C1 C2T1 C3T1 C4T1 -173.1(2) . . . . ?
C1 C2T2 C3T2 C4T2 167(3) . . . . ?
C1B C1P C2P C3P -176.48(16) . . . . ?
C1B C1P C2P C5 6.5(3) . . . . ?
C1B C1P C6P C5P 177.82(15) . . . . ?
C1B C2B C3B C4B -0.7(3) . . . . ?
C1M N3N C2N N1N 177.25(15) . . . . ?
C1M N3N C2N C1 -6.5(2) . . . . ?
C1M N3N C4N O1N 1.7(3) . . . . ?
C1M N3N C4N C5N -178.92(14) . . . . ?
C1M C4B C5B C6B 176.86(15) . . . . ?
C1P C1B C2B C3B -179.28(15) . . . . ?
C1P C1B C6B C5B -179.52(15) . . . . ?
C1P C2P C3P C4P -1.7(3) . . . . ?
C1P C2P C5 N1 50.6(2) . . . . ?
C1P C2P C5 N4 -135.27(18) . . . . ?
C2B C1B C1P C2P -140.96(17) . . . . ?
C2B C1B C1P C6P 40.3(2) . . . . ?
C2B C1B C6B C5B 2.4(2) . . . . ?
C2B C3B C4B C1M -175.65(15) . . . . ?
C2B C3B C4B C5B 1.4(2) . . . . ?
C2N N1N C5N C4N -2.34(17) . . . . ?
C2N N1N C5N C6N 119.96(15) . . . . ?
C2N N1N C5N C9N -126.06(15) . . . . ?
C2N N3N C1M C4B -85.92(19) . . . . ?
C2N N3N C4N O1N 179.10(16) . . . . ?
C2N N3N C4N C5N -1.49(17) . . . . ?
C2N C1 C2T1 C3T1 -173.19(16) . . . . ?
C2N C1 C2T2 C3T2 178(2) . . . . ?
C2P C1P C6P C5P -1.0(2) . . . . ?
C2P C3P C4P C5P -0.2(3) . . . . ?
C2T1 C1 C2N N1N 93.0(2) . . . . ?
C2T1 C1 C2N N3N -82.81(19) . . . . ?
C2T2 C1 C2N N1N 38.0(19) . . . . ?
C2T2 C1 C2N N3N -137.8(18) . . . . ?
C3B C4B C5B C6B -0.2(2) . . . . ?
C3P C2P C5 N1 -126.53(18) . . . . ?
C3P C2P C5 N4 47.6(2) . . . . ?
C3P C4P C5P C6P 1.5(3) . . . . ?
C4B C5B C6B C1B -1.8(2) . . . . ?
C4N N3N C1M C4B 90.98(19) . . . . ?
C4N N3N C2N N1N -0.01(19) . . . . ?
C4N N3N C2N C1 176.21(15) . . . . ?
C4N C5N C6N C7N -163.48(13) . . . . ?
C4N C5N C9N C8N 156.53(15) . . . . ?
C4P C5P C6P C1P -0.9(3) . . . . ?
C5 N1 N2 N3 0.28(17) . . . . ?
C5 C2P C3P C4P 175.57(17) . . . . ?
C5N N1N C2N N3N 1.56(19) . . . . ?
C5N N1N C2N C1 -174.61(15) . . . . ?
C5N C6N C7N C8N 31.60(17) . . . . ?
C6B C1B C1P C2P 41.0(2) . . . . ?
C6B C1B C1P C6P -137.75(16) . . . . ?
C6B C1B C2B C3B -1.2(2) . . . . ?
C6N C5N C9N C8N 33.61(17) . . . . ?
C6N C7N C8N C9N -10.68(18) . . . . ?
C6P C1P C2P C3P 2.3(2) . . . . ?
C6P C1P C2P C5 -174.74(15) . . . . ?
C7N C8N C9N C5N -14.36(19) . . . . ?
C9N C5N C6N C7N -40.15(17) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.450 550.0 58.9 '6 water'
2 0.333 0.667 -0.855 550.0 58.9 '6 water'
3 0.667 0.333 -0.188 550.0 58.9 '6 water'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ibs_a_231k_zwitter
_database_code_depnum_ccdc_archive 'CCDC 1999412'
loop_
_audit_author_name
_audit_author_address
'Philippe Ochsenbein'
;Analytical Science Department, Sanofi Avensis, Montpellier
France
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2020-04-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_THETM01_ibs_a_231k_zwitter  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was very thin and small and weakly-diffracting,
          perhaps also because of [001] channels in the structure. But
		  the defect is very minor and the quality of the structure is
		  certainly very good. 
;
_chemical_name_common            SR47436-A
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 N6 O, 0.4[H2O]'
_chemical_formula_sum            'C25 H28 N6 O'
_chemical_formula_weight         428.53
_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   37.3328(5)
_cell_length_b                   37.3328(5)
_cell_length_c                   9.7877(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11813.9(4)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    231(1)
_cell_measurement_theta_max      54.19
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    0.550
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V2012/1 (Bruker AXS Inc.) was used for absorption correction.
wR2(int) was 0.1579 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.867.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             4104
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.016
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            38412
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        54.811
_diffrn_reflns_theta_max         54.811
_diffrn_reflns_theta_min         2.367
_diffrn_ambient_temperature      231(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX_DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2874
_reflns_number_total             3273
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker Instrument Service v2016.5.0.1'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.000037(9)
_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   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.198
_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)+(0.0543P)²+9.9024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1021
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2T1-C1 \\sim C2T2-C1 \\sim C2T1-C3T1 \\sim C2T2-C3T2 \\sim C4T1-C3T1 \\sim
C4T2-C3T2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2T1 \\sim C2T2 \\sim C3T1 \\sim C3T2 \\sim C4T1 \\sim C4T2: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(H1BC)=Sof(H1BD)=Sof(C2T2)=Sof(H2TC)=Sof(H2TD)=Sof(C3T2)=Sof(H3TC)=
 Sof(H3TD)=Sof(C4T2)=Sof(H4TD)=Sof(H4TE)=Sof(H4TF)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C2T1)=Sof(H2TA)=Sof(H2TB)=Sof(C3T1)=Sof(H3TA)=
 Sof(H3TB)=Sof(C4T1)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=FVAR(1)
 Sof(H1N)=1-FVAR(2)
 Sof(H1)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1M(H1MA,H1MB), C2T1(H2TA,H2TB), C2T2(H2TC,
 H2TD), C3T1(H3TA,H3TB), C3T2(H3TC,H3TD), C6N(H6NA,H6NB), C7N(H7NA,H7NB),
 C8N(H8NA,H8NB), C9N(H9NA,H9NB)
5.b Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C3P(H3P), C4P(H4P), C5B(H5B), C5P(H5P), C6B(H6B), C6P(H6P)
5.c Idealised Me refined as rotating group:
 C4T1(H4TA,H4TB,H4TC), C4T2(H4TD,H4TE,H4TF)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O1N O 0.39161(4) 0.42018(4) 0.52002(14) 0.0602(4) Uani 1 1 d . . . . .
N1 N 0.15049(4) 0.24210(4) 0.32052(16) 0.0414(4) Uani 1 1 d . . . . .
H1 H 0.1632(7) 0.2428(6) 0.401(3) 0.037(8) Uiso 0.79(4) 1 d . . P A 1
N1N N 0.39540(5) 0.48245(5) 0.24234(16) 0.0443(4) Uani 1 1 d . . . . .
H1N H 0.403(3) 0.496(3) 0.179(12) 0.053 Uiso 0.21(4) 1 d . U P A 2
N2 N 0.11838(5) 0.24895(5) 0.31734(16) 0.0498(4) Uani 1 1 d . . . . .
N3 N 0.10513(5) 0.24263(5) 0.19277(16) 0.0551(4) Uani 1 1 d . . . . .
N3N N 0.34956(4) 0.43347(4) 0.38209(13) 0.0372(4) Uani 1 1 d . . . . .
N4 N 0.12783(5) 0.23156(5) 0.11376(15) 0.0513(4) Uani 1 1 d . . . . .
C1 C 0.32312(6) 0.46342(7) 0.2052(2) 0.0600(5) Uani 1 1 d D U . . .
H1AA H 0.297102 0.437122 0.213586 0.072 Uiso 0.555(4) 1 calc R U P B 1
H1AB H 0.329372 0.469318 0.107755 0.072 Uiso 0.555(4) 1 calc R U P B 1
H1BC H 0.315094 0.445665 0.124069 0.072 Uiso 0.445(4) 1 calc R U P B 2
H1BD H 0.299349 0.451201 0.267280 0.072 Uiso 0.445(4) 1 calc R U P B 2
C1B C 0.24925(5) 0.28224(5) 0.24891(16) 0.0345(4) Uani 1 1 d . . . . .
C1M C 0.30975(5) 0.40266(5) 0.44109(18) 0.0433(5) Uani 1 1 d . . . . .
H1MA H 0.290735 0.413573 0.437953 0.052 Uiso 1 1 calc R U . . .
H1MB H 0.313989 0.398518 0.537320 0.052 Uiso 1 1 calc R U . . .
C1P C 0.22821(5) 0.24044(5) 0.18576(16) 0.0360(4) Uani 1 1 d . . . . .
C2B C 0.27957(5) 0.29258(5) 0.34821(17) 0.0410(4) Uani 1 1 d . . . . .
H2B H 0.286558 0.272727 0.375815 0.049 Uiso 1 1 calc R U . . .
C2N C 0.35700(6) 0.46017(5) 0.27331(17) 0.0409(4) Uani 1 1 d . . . . .
C2P C 0.18572(5) 0.21837(5) 0.15517(16) 0.0397(4) Uani 1 1 d . . . . .
C2T1 C 0.31866(14) 0.49734(14) 0.2701(5) 0.0783(12) Uani 0.555(4) 1 d D U P B 1
H2TA H 0.346051 0.522127 0.277243 0.094 Uiso 0.555(4) 1 calc R U P B 1
H2TB H 0.307883 0.488917 0.363006 0.094 Uiso 0.555(4) 1 calc R U P B 1
C2T2 C 0.32880(17) 0.50317(15) 0.1617(7) 0.0778(13) Uani 0.445(4) 1 d D U P B 2
H2TC H 0.351887 0.515504 0.096903 0.093 Uiso 0.445(4) 1 calc R U P B 2
H2TD H 0.336777 0.521401 0.241557 0.093 Uiso 0.445(4) 1 calc R U P B 2
C3B C 0.29957(5) 0.33136(6) 0.40694(17) 0.0419(5) Uani 1 1 d . . . . .
H3B H 0.320062 0.337553 0.473301 0.050 Uiso 1 1 calc R U . . .
C3P C 0.16902(6) 0.18053(6) 0.08815(19) 0.0539(5) Uani 1 1 d . . . . .
H3P H 0.140772 0.166322 0.065485 0.065 Uiso 1 1 calc R U . . .
C3T1 C 0.29056(18) 0.50798(18) 0.1928(7) 0.1027(14) Uani 0.555(4) 1 d D U P B 1
H3TA H 0.303680 0.521004 0.106004 0.123 Uiso 0.555(4) 1 calc R U P B 1
H3TB H 0.264729 0.482463 0.171928 0.123 Uiso 0.555(4) 1 calc R U P B 1
C3T2 C 0.2918(2) 0.5022(2) 0.0958(9) 0.0967(17) Uani 0.445(4) 1 d D U P B 2
H3TC H 0.282773 0.482944 0.018591 0.116 Uiso 0.445(4) 1 calc R U P B 2
H3TD H 0.269139 0.491633 0.162161 0.116 Uiso 0.445(4) 1 calc R U P B 2
C4B C 0.28986(5) 0.36135(5) 0.36940(16) 0.0360(4) Uani 1 1 d . . . . .
C4N C 0.38686(5) 0.43891(5) 0.42720(18) 0.0411(4) Uani 1 1 d . . . . .
C4P C 0.19322(7) 0.16348(6) 0.0543(2) 0.0587(6) Uani 1 1 d . . . . .
H4P H 0.181527 0.137891 0.008936 0.070 Uiso 1 1 calc R U . . .
C4T1 C 0.2810(3) 0.5358(2) 0.2686(10) 0.183(3) Uani 0.555(4) 1 d D U P B 1
H4TA H 0.265947 0.544694 0.210161 0.275 Uiso 0.555(4) 1 calc R U P B 1
H4TB H 0.306554 0.559780 0.298492 0.275 Uiso 0.555(4) 1 calc R U P B 1
H4TC H 0.264266 0.521519 0.347647 0.275 Uiso 0.555(4) 1 calc R U P B 1
C4T2 C 0.2998(3) 0.5427(2) 0.0468(10) 0.150(3) Uani 0.445(4) 1 d D U P B 2
H4TD H 0.320623 0.552393 -0.024585 0.225 Uiso 0.445(4) 1 calc R U P B 2
H4TE H 0.309702 0.562264 0.121940 0.225 Uiso 0.445(4) 1 calc R U P B 2
H4TF H 0.274486 0.540189 0.010725 0.225 Uiso 0.445(4) 1 calc R U P B 2
C5 C 0.15607(5) 0.23162(5) 0.19522(17) 0.0384(4) Uani 1 1 d . . . . .
C5B C 0.26008(5) 0.35138(5) 0.26904(17) 0.0389(4) Uani 1 1 d . . . . .
H5B H 0.253102 0.371260 0.241717 0.047 Uiso 1 1 calc R U . . .
C5N C 0.41930(5) 0.47252(5) 0.33894(16) 0.0389(4) Uani 1 1 d . . . . .
C5P C 0.23425(6) 0.18406(6) 0.08732(19) 0.0509(5) Uani 1 1 d . . . . .
H5P H 0.250701 0.172261 0.066496 0.061 Uiso 1 1 calc R U . . .
C6B C 0.24051(5) 0.31282(5) 0.20860(17) 0.0377(4) Uani 1 1 d . . . . .
H6B H 0.220977 0.307113 0.139164 0.045 Uiso 1 1 calc R U . . .
C6N C 0.44973(6) 0.51099(6) 0.41994(19) 0.0503(5) Uani 1 1 d . . . . .
H6NA H 0.437668 0.528439 0.440347 0.060 Uiso 1 1 calc R U . . .
H6NB H 0.457484 0.503199 0.505899 0.060 Uiso 1 1 calc R U . . .
C6P C 0.25169(6) 0.22206(6) 0.15099(17) 0.0427(5) Uani 1 1 d . . . . .
H6P H 0.280091 0.235972 0.171554 0.051 Uiso 1 1 calc R U . . .
C7N C 0.48682(6) 0.53323(6) 0.3264(2) 0.0563(5) Uani 1 1 d . . . . .
H7NA H 0.483335 0.551970 0.264858 0.068 Uiso 1 1 calc R U . . .
H7NB H 0.512154 0.549356 0.379777 0.068 Uiso 1 1 calc R U . . .
C8N C 0.48897(6) 0.49977(6) 0.2461(2) 0.0520(5) Uani 1 1 d . . . . .
H8NA H 0.511717 0.496150 0.279421 0.062 Uiso 1 1 calc R U . . .
H8NB H 0.493533 0.507062 0.148964 0.062 Uiso 1 1 calc R U . . .
C9N C 0.44778(6) 0.46029(6) 0.2666(2) 0.0545(5) Uani 1 1 d . . . . .
H9NA H 0.451481 0.440567 0.322336 0.065 Uiso 1 1 calc R U . . .
H9NB H 0.436005 0.447389 0.178312 0.065 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
O1N C4N 1.213(2) . ?
N1 H1 0.92(3) . ?
N1 N2 1.345(2) . ?
N1 C5 1.335(2) . ?
N1N H1N 0.77(12) . ?
N1N C2N 1.283(2) . ?
N1N C5N 1.469(2) . ?
N2 N3 1.292(2) . ?
N3 N4 1.355(2) . ?
N3N C1M 1.468(2) . ?
N3N C2N 1.388(2) . ?
N3N C4N 1.376(2) . ?
N4 C5 1.321(2) . ?
C1 H1AA 0.9800 . ?
C1 H1AB 0.9800 . ?
C1 H1BC 0.9800 . ?
C1 H1BD 0.9800 . ?
C1 C2N 1.488(3) . ?
C1 C2T1 1.499(4) . ?
C1 C2T2 1.454(5) . ?
C1B C1P 1.486(2) . ?
C1B C2B 1.392(2) . ?
C1B C6B 1.392(2) . ?
C1M H1MA 0.9800 . ?
C1M H1MB 0.9800 . ?
C1M C4B 1.509(2) . ?
C1P C2P 1.406(2) . ?
C1P C6P 1.399(2) . ?
C2B H2B 0.9400 . ?
C2B C3B 1.379(2) . ?
C2P C3P 1.391(2) . ?
C2P C5 1.474(2) . ?
C2T1 H2TA 0.9800 . ?
C2T1 H2TB 0.9800 . ?
C2T1 C3T1 1.499(5) . ?
C2T2 H2TC 0.9800 . ?
C2T2 H2TD 0.9800 . ?
C2T2 C3T2 1.508(6) . ?
C3B H3B 0.9400 . ?
C3B C4B 1.388(2) . ?
C3P H3P 0.9400 . ?
C3P C4P 1.380(3) . ?
C3T1 H3TA 0.9800 . ?
C3T1 H3TB 0.9800 . ?
C3T1 C4T1 1.459(6) . ?
C3T2 H3TC 0.9800 . ?
C3T2 H3TD 0.9800 . ?
C3T2 C4T2 1.466(6) . ?
C4B C5B 1.388(2) . ?
C4N C5N 1.506(2) . ?
C4P H4P 0.9400 . ?
C4P C5P 1.365(3) . ?
C4T1 H4TA 0.9700 . ?
C4T1 H4TB 0.9700 . ?
C4T1 H4TC 0.9700 . ?
C4T2 H4TD 0.9700 . ?
C4T2 H4TE 0.9700 . ?
C4T2 H4TF 0.9700 . ?
C5B H5B 0.9400 . ?
C5B C6B 1.380(2) . ?
C5N C6N 1.533(2) . ?
C5N C9N 1.525(3) . ?
C5P H5P 0.9400 . ?
C5P C6P 1.379(3) . ?
C6B H6B 0.9400 . ?
C6N H6NA 0.9800 . ?
C6N H6NB 0.9800 . ?
C6N C7N 1.515(3) . ?
C6P H6P 0.9400 . ?
C7N H7NA 0.9800 . ?
C7N H7NB 0.9800 . ?
C7N C8N 1.512(3) . ?
C8N H8NA 0.9800 . ?
C8N H8NB 0.9800 . ?
C8N C9N 1.520(3) . ?
C9N H9NA 0.9800 . ?
C9N H9NB 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
N2 N1 H1 120.8(13) . . ?
C5 N1 H1 130.4(13) . . ?
C5 N1 N2 108.59(15) . . ?
C2N N1N H1N 123(7) . . ?
C2N N1N C5N 107.88(15) . . ?
C5N N1N H1N 129(7) . . ?
N3 N2 N1 106.46(14) . . ?
N2 N3 N4 110.69(14) . . ?
C2N N3N C1M 128.69(14) . . ?
C4N N3N C1M 122.87(14) . . ?
C4N N3N C2N 108.40(14) . . ?
C5 N4 N3 105.97(14) . . ?
H1AA C1 H1AB 108.2 . . ?
H1BC C1 H1BD 106.8 . . ?
C2N C1 H1AA 109.7 . . ?
C2N C1 H1AB 109.7 . . ?
C2N C1 H1BC 107.0 . . ?
C2N C1 H1BD 107.0 . . ?
C2N C1 C2T1 109.7(2) . . ?
C2T1 C1 H1AA 109.7 . . ?
C2T1 C1 H1AB 109.7 . . ?
C2T2 C1 H1BC 107.0 . . ?
C2T2 C1 H1BD 107.0 . . ?
C2T2 C1 C2N 121.2(3) . . ?
C2B C1B C1P 120.74(14) . . ?
C2B C1B C6B 117.51(15) . . ?
C6B C1B C1P 121.71(15) . . ?
N3N C1M H1MA 108.8 . . ?
N3N C1M H1MB 108.8 . . ?
N3N C1M C4B 113.96(13) . . ?
H1MA C1M H1MB 107.7 . . ?
C4B C1M H1MA 108.8 . . ?
C4B C1M H1MB 108.8 . . ?
C2P C1P C1B 123.56(14) . . ?
C6P C1P C1B 118.97(15) . . ?
C6P C1P C2P 117.45(16) . . ?
C1B C2B H2B 119.3 . . ?
C3B C2B C1B 121.36(16) . . ?
C3B C2B H2B 119.3 . . ?
N1N C2N N3N 113.86(16) . . ?
N1N C2N C1 124.12(16) . . ?
N3N C2N C1 121.96(16) . . ?
C1P C2P C5 124.29(15) . . ?
C3P C2P C1P 119.79(16) . . ?
C3P C2P C5 115.86(16) . . ?
C1 C2T1 H2TA 108.9 . . ?
C1 C2T1 H2TB 108.9 . . ?
C1 C2T1 C3T1 113.4(4) . . ?
H2TA C2T1 H2TB 107.7 . . ?
C3T1 C2T1 H2TA 108.9 . . ?
C3T1 C2T1 H2TB 108.9 . . ?
C1 C2T2 H2TC 108.3 . . ?
C1 C2T2 H2TD 108.3 . . ?
C1 C2T2 C3T2 115.9(4) . . ?
H2TC C2T2 H2TD 107.4 . . ?
C3T2 C2T2 H2TC 108.3 . . ?
C3T2 C2T2 H2TD 108.3 . . ?
C2B C3B H3B 119.5 . . ?
C2B C3B C4B 120.91(16) . . ?
C4B C3B H3B 119.5 . . ?
C2P C3P H3P 119.4 . . ?
C4P C3P C2P 121.15(18) . . ?
C4P C3P H3P 119.4 . . ?
C2T1 C3T1 H3TA 109.1 . . ?
C2T1 C3T1 H3TB 109.1 . . ?
H3TA C3T1 H3TB 107.8 . . ?
C4T1 C3T1 C2T1 112.6(6) . . ?
C4T1 C3T1 H3TA 109.1 . . ?
C4T1 C3T1 H3TB 109.1 . . ?
C2T2 C3T2 H3TC 108.8 . . ?
C2T2 C3T2 H3TD 108.8 . . ?
H3TC C3T2 H3TD 107.7 . . ?
C4T2 C3T2 C2T2 113.8(6) . . ?
C4T2 C3T2 H3TC 108.8 . . ?
C4T2 C3T2 H3TD 108.8 . . ?
C3B C4B C1M 120.51(15) . . ?
C5B C4B C1M 121.49(15) . . ?
C5B C4B C3B 117.93(16) . . ?
O1N C4N N3N 125.78(16) . . ?
O1N C4N C5N 128.44(16) . . ?
N3N C4N C5N 105.78(14) . . ?
C3P C4P H4P 120.3 . . ?
C5P C4P C3P 119.50(18) . . ?
C5P C4P H4P 120.3 . . ?
C3T1 C4T1 H4TA 109.5 . . ?
C3T1 C4T1 H4TB 109.5 . . ?
C3T1 C4T1 H4TC 109.5 . . ?
H4TA C4T1 H4TB 109.5 . . ?
H4TA C4T1 H4TC 109.5 . . ?
H4TB C4T1 H4TC 109.5 . . ?
C3T2 C4T2 H4TD 109.5 . . ?
C3T2 C4T2 H4TE 109.5 . . ?
C3T2 C4T2 H4TF 109.5 . . ?
H4TD C4T2 H4TE 109.5 . . ?
H4TD C4T2 H4TF 109.5 . . ?
H4TE C4T2 H4TF 109.5 . . ?
N1 C5 C2P 126.60(15) . . ?
N4 C5 N1 108.29(15) . . ?
N4 C5 C2P 124.87(15) . . ?
C4B C5B H5B 119.4 . . ?
C6B C5B C4B 121.24(16) . . ?
C6B C5B H5B 119.4 . . ?
N1N C5N C4N 104.03(14) . . ?
N1N C5N C6N 110.83(14) . . ?
N1N C5N C9N 112.29(15) . . ?
C4N C5N C6N 113.23(14) . . ?
C4N C5N C9N 114.05(15) . . ?
C9N C5N C6N 102.68(14) . . ?
C4P C5P H5P 119.8 . . ?
C4P C5P C6P 120.38(17) . . ?
C6P C5P H5P 119.8 . . ?
C1B C6B H6B 119.5 . . ?
C5B C6B C1B 121.00(16) . . ?
C5B C6B H6B 119.5 . . ?
C5N C6N H6NA 110.9 . . ?
C5N C6N H6NB 110.9 . . ?
H6NA C6N H6NB 108.9 . . ?
C7N C6N C5N 104.30(14) . . ?
C7N C6N H6NA 110.9 . . ?
C7N C6N H6NB 110.9 . . ?
C1P C6P H6P 119.2 . . ?
C5P C6P C1P 121.68(17) . . ?
C5P C6P H6P 119.2 . . ?
C6N C7N H7NA 110.6 . . ?
C6N C7N H7NB 110.6 . . ?
H7NA C7N H7NB 108.7 . . ?
C8N C7N C6N 105.84(15) . . ?
C8N C7N H7NA 110.6 . . ?
C8N C7N H7NB 110.6 . . ?
C7N C8N H8NA 110.4 . . ?
C7N C8N H8NB 110.4 . . ?
C7N C8N C9N 106.65(15) . . ?
H8NA C8N H8NB 108.6 . . ?
C9N C8N H8NA 110.4 . . ?
C9N C8N H8NB 110.4 . . ?
C5N C9N H9NA 110.4 . . ?
C5N C9N H9NB 110.4 . . ?
C8N C9N C5N 106.84(15) . . ?
C8N C9N H9NA 110.4 . . ?
C8N C9N H9NB 110.4 . . ?
H9NA C9N H9NB 108.6 . . ?

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 N1N 0.92(3) 1.86(3) 2.766(2) 172(2) 5 yes
N1N H1N N1 0.77(12) 2.03(12) 2.766(2) 160(10) 9_554 yes
C1M H1MA N3 0.98 2.58 3.527(2) 163.4 16 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
O1N C4N C5N N1N 178.33(18) . . . . ?
O1N C4N C5N C6N -61.3(2) . . . . ?
O1N C4N C5N C9N 55.7(2) . . . . ?
N1 N2 N3 N4 0.3(2) . . . . ?
N1N C5N C6N C7N -82.97(18) . . . . ?
N1N C5N C9N C8N 90.52(18) . . . . ?
N2 N1 C5 N4 -0.35(19) . . . . ?
N2 N1 C5 C2P -174.89(16) . . . . ?
N2 N3 N4 C5 -0.5(2) . . . . ?
N3 N4 C5 N1 0.5(2) . . . . ?
N3 N4 C5 C2P 175.15(16) . . . . ?
N3N C1M C4B C3B 87.07(19) . . . . ?
N3N C1M C4B C5B -95.96(18) . . . . ?
N3N C4N C5N N1N -2.16(17) . . . . ?
N3N C4N C5N C6N 118.24(16) . . . . ?
N3N C4N C5N C9N -124.82(16) . . . . ?
C1 C2T1 C3T1 C4T1 170.3(5) . . . . ?
C1 C2T2 C3T2 C4T2 -176.7(7) . . . . ?
C1B C1P C2P C3P 175.92(16) . . . . ?
C1B C1P C2P C5 -7.1(3) . . . . ?
C1B C1P C6P C5P -177.44(15) . . . . ?
C1B C2B C3B C4B 0.5(3) . . . . ?
C1M N3N C2N N1N -177.34(15) . . . . ?
C1M N3N C2N C1 5.4(3) . . . . ?
C1M N3N C4N O1N -1.4(3) . . . . ?
C1M N3N C4N C5N 179.03(14) . . . . ?
C1M C4B C5B C6B -176.75(15) . . . . ?
C1P C1B C2B C3B 179.50(15) . . . . ?
C1P C1B C6B C5B 179.47(15) . . . . ?
C1P C2P C3P C4P 1.9(3) . . . . ?
C1P C2P C5 N1 -52.1(3) . . . . ?
C1P C2P C5 N4 134.25(19) . . . . ?
C2B C1B C1P C2P 140.30(17) . . . . ?
C2B C1B C1P C6P -41.4(2) . . . . ?
C2B C1B C6B C5B -2.5(2) . . . . ?
C2B C3B C4B C1M 175.73(15) . . . . ?
C2B C3B C4B C5B -1.3(2) . . . . ?
C2N N1N C5N C4N 2.32(18) . . . . ?
C2N N1N C5N C6N -119.68(16) . . . . ?
C2N N1N C5N C9N 126.13(16) . . . . ?
C2N N3N C1M C4B 85.4(2) . . . . ?
C2N N3N C4N O1N -179.17(17) . . . . ?
C2N N3N C4N C5N 1.30(17) . . . . ?
C2N C1 C2T1 C3T1 169.8(4) . . . . ?
C2N C1 C2T2 C3T2 -179.1(5) . . . . ?
C2P C1P C6P C5P 0.9(2) . . . . ?
C2P C3P C4P C5P 0.1(3) . . . . ?
C2T1 C1 C2N N1N -84.4(3) . . . . ?
C2T1 C1 C2N N3N 92.6(3) . . . . ?
C2T2 C1 C2N N1N -36.7(4) . . . . ?
C2T2 C1 C2N N3N 140.2(4) . . . . ?
C3B C4B C5B C6B 0.3(2) . . . . ?
C3P C2P C5 N1 125.03(19) . . . . ?
C3P C2P C5 N4 -48.6(2) . . . . ?
C3P C4P C5P C6P -1.5(3) . . . . ?
C4B C5B C6B C1B 1.7(2) . . . . ?
C4N N3N C1M C4B -91.83(19) . . . . ?
C4N N3N C2N N1N 0.2(2) . . . . ?
C4N N3N C2N C1 -177.03(16) . . . . ?
C4N C5N C6N C7N 160.58(16) . . . . ?
C4N C5N C9N C8N -151.46(16) . . . . ?
C4P C5P C6P C1P 1.0(3) . . . . ?
C5 N1 N2 N3 0.06(19) . . . . ?
C5 C2P C3P C4P -175.32(18) . . . . ?
C5N N1N C2N N3N -1.7(2) . . . . ?
C5N N1N C2N C1 175.50(16) . . . . ?
C5N C6N C7N C8N -32.1(2) . . . . ?
C6B C1B C1P C2P -41.8(2) . . . . ?
C6B C1B C1P C6P 136.53(16) . . . . ?
C6B C1B C2B C3B 1.5(2) . . . . ?
C6N C5N C9N C8N -28.56(19) . . . . ?
C6N C7N C8N C9N 14.1(2) . . . . ?
C6P C1P C2P C3P -2.4(2) . . . . ?
C6P C1P C2P C5 174.63(15) . . . . ?
C7N C8N C9N C5N 9.3(2) . . . . ?
C9N C5N C6N C7N 37.13(19) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.376 590.6 25.9 '2.4 water'
2 0.333 0.667 -0.683 590.6 25.9 '2.4 water'
3 0.667 0.333 -0.017 590.6 25.9 '2.4 water'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ibs-a-temp_06_90_00
_database_code_depnum_ccdc_archive 'CCDC 2266410'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2023-05-30 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2023-05-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_contact_author            'Farzaneh Fadaei Tirani'
# start Validation Reply Form
_vrf_PLAT601_ibs-a-temp_06_90_00 
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        510 Ang**3
RESPONSE: There are [001]-channels in this structure. They can be filled with
          water, contain no solvent at all or even be partially filled with
		  water and other solvents. The contents varies with time, and in 
		  this crystal it so happens that there is no solvent whatsoever,
		  yet the structure is not affected. This is part of the 
		  metastabillity of the structure we discuss in the paper.
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 N6 O'
_chemical_formula_sum            'C25 H28 N6 O'
_chemical_formula_weight         428.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H28 O N6'
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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   37.2454(8)
_cell_length_b                   37.2454(8)
_cell_length_c                   9.65133(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11594.8(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    7457
_cell_measurement_temperature    89.9(6)
_cell_measurement_theta_max      73.4430
_cell_measurement_theta_min      2.3540
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.799
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             4104
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0303
-1 0 0 0.0043
1 -1 0 0.0245
-1 1 0 0.0055
0 0 -1 0.1650
0 0 1 0.2520
0 1 0 0.0222
0 -1 0 0.0062

_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0060 -0.0167 -0.0044 0.0345 -0.0324 -0.0056
-1.0060 0.0167 0.0044 -0.0345 0.0324 0.0056
0.9881 -1.0044 -0.0094 0.0457 0.0129 0.0039
-0.9881 1.0044 0.0094 -0.0457 -0.0129 -0.0039
-0.1014 0.1058 -0.9841 -0.0043 -0.0312 0.1540
0.1014 -0.1058 0.9841 0.0043 0.0312 -0.1540
0.0179 0.9877 0.0050 -0.0112 -0.0453 -0.0095
-0.0179 -0.9877 -0.0050 0.0112 0.0453 0.0095

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            30151
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.719
_diffrn_reflns_theta_min         2.373
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      89.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -36.00   0.50    2.00    --  -74.55 146.00  41.00  138
  2  ω     64.00 103.00   0.50    2.00    --   79.85-112.00-150.00   78
  3  ω     82.00 121.00   0.50    2.00    --   79.85 145.00-178.00   78
  4  ω     65.00  91.00   0.50    2.00    --   59.56  30.00-180.00   52
  5  ω     10.00  36.00   0.50    2.00    --   59.56 -30.00 -90.00   52
  6  ω     49.00  83.00   0.50    2.00    --   73.45 -95.00 -90.00   68
  7  ω   -122.00 -83.00   0.50    2.00    --  -74.55 -30.00-120.00   78
  8  ω   -112.00 -82.00   0.50    2.00    --  -75.95 -30.00 -90.00   60
  9  ω     82.00 118.00   0.50    2.00    --   79.85  30.00   0.00   72
 10  ω     35.00  66.00   0.50    2.00    --   79.85-111.00 -60.00   62
 11  ω     61.00  94.00   0.50    2.00    --   79.85-111.00 -90.00   66
 12  ω     38.00  71.00   0.50    2.00    --   79.85-111.00  30.00   66
 13  ω     56.00  81.00   0.50    2.00    --   79.85 -95.00  90.00   50
 14  ω     49.00  74.00   0.50    2.00    --   79.85 -95.00 -30.00   50
 15  ω     90.00 127.00   0.50    2.00    --   79.85  30.00-150.00   74
 16  ω     72.00 115.00   0.50    2.00    --   79.85  15.00  30.00   86
 17  ω     70.00 111.00   0.50    2.00    --   79.85  15.00 120.00   82
 18  ω     86.00 111.00   0.50    2.00    --   79.85  30.00 -90.00   50
 19  ω     36.00  69.00   0.50    2.00    --   79.85-111.00  60.00   66
 20  ω     78.00 103.00   0.50    2.00    --   79.85-111.00-120.00   50
 21  ω     63.00  96.00   0.50    2.00    --   79.85 156.00 154.00   66
 22  ω     46.00  71.00   0.50    2.00    --   79.85 -95.00 -90.00   50
 23  ω     45.00  70.00   0.50    2.00    --   79.85 -95.00 150.00   50
 24  ω     37.00 103.00   0.50    2.00    --   79.85-111.00 -30.00  132
 25  ω     84.00 114.00   0.50    2.00    --   79.85-136.00 -35.00   60
 26  ω     79.00 104.00   0.50    2.00    --   79.85 136.00  29.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0340493667
_diffrn_orient_matrix_UB_12      -0.0119892667
_diffrn_orient_matrix_UB_13      -0.0004634667
_diffrn_orient_matrix_UB_21      -0.0328340000
_diffrn_orient_matrix_UB_22      -0.0454059000
_diffrn_orient_matrix_UB_23      0.0301780000
_diffrn_orient_matrix_UB_31      -0.0064033333
_diffrn_orient_matrix_UB_32      -0.0086707667
_diffrn_orient_matrix_UB_33      -0.1567802667
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4121
_reflns_number_total             5233
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.000047(8)
_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   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5233
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²+12.5545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1027
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2T1-C1 = C3T1-C2T1 = C4T1-C3T1 = C2T2-C1 = C3T2-C2T2 = C4T2-C3T2
 1.54 with sigma of 0.02
 C1-C3T2 = C2T2-C4T2
 2.54 with sigma of 0.02
 C1-C3T1 = C2T1-C4T1
 2.54 with sigma of 0.02
 C4T2-C3T2
 1.54 with sigma of 0.01
 C4T1-C3T1
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2T1 \\sim C2T2 \\sim C3T1 \\sim C3T2 \\sim C4T1 \\sim C4T2: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(H1BC)=Sof(H1BD)=Sof(C2T2)=Sof(H2TC)=Sof(H2TD)=Sof(C3T2)=Sof(H3TC)=
 Sof(H3TD)=Sof(C4T2)=Sof(H4TD)=Sof(H4TE)=Sof(H4TF)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C2T1)=Sof(H2TA)=Sof(H2TB)=Sof(C3T1)=Sof(H3TA)=
 Sof(H3TB)=Sof(C4T1)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1M(H1MA,H1MB), C2T1(H2TA,H2TB), C2T2(H2TC,
 H2TD), C3T1(H3TA,H3TB), C3T2(H3TC,H3TD), C6N(H6NA,H6NB), C7N(H7NA,H7NB),
 C8N(H8NA,H8NB), C9N(H9NA,H9NB)
5.b Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C3P(H3P), C4P(H4P), C5B(H5B), C5P(H5P), C6B(H6B), C6P(H6P)
5.c Idealised Me refined as rotating group:
 C4T1(H4TA,H4TB,H4TC), C4T2(H4TD,H4TE,H4TF)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O1N O 0.27488(3) 0.36189(3) 0.30429(11) 0.0251(3) Uani 1 1 d . . . . .
N1 N 0.51648(4) 0.42725(4) 0.51429(13) 0.0183(3) Uani 1 1 d . . . . .
H1 H 0.5035(5) 0.4160(5) 0.4247(17) 0.022 Uiso 1 1 d . U . . .
N1N N 0.26799(4) 0.41768(4) 0.59144(12) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.54925(4) 0.46619(4) 0.52053(13) 0.0206(3) Uani 1 1 d . . . . .
N3 N 0.56289(4) 0.47172(4) 0.64676(13) 0.0224(3) Uani 1 1 d . . . . .
N3N N 0.31560(4) 0.41697(4) 0.44986(12) 0.0175(3) Uani 1 1 d . . . . .
N4 N 0.53988(4) 0.43707(4) 0.72455(13) 0.0215(3) Uani 1 1 d . . . . .
C1 C 0.33957(5) 0.47216(5) 0.63473(16) 0.0230(3) Uani 1 1 d D U . . .
H1AA H 0.365018 0.470149 0.641922 0.028 Uiso 0.964(2) 1 calc R U P A 1
H1AB H 0.330101 0.473039 0.729873 0.028 Uiso 0.964(2) 1 calc R U P A 1
H1BC H 0.363955 0.484122 0.572459 0.028 Uiso 0.036(2) 1 calc R U P A 2
H1BD H 0.347374 0.461629 0.716810 0.028 Uiso 0.036(2) 1 calc R U P A 2
C1B C 0.41740(4) 0.36706(5) 0.58210(14) 0.0164(3) Uani 1 1 d . . . . .
C1M C 0.35610(5) 0.42746(5) 0.39228(15) 0.0189(3) Uani 1 1 d . . . . .
H1MA H 0.374856 0.457791 0.399603 0.023 Uiso 1 1 calc R U . . .
H1MB H 0.352707 0.420144 0.292665 0.023 Uiso 1 1 calc R U . . .
C1P C 0.43855(5) 0.34610(5) 0.64408(14) 0.0168(3) Uani 1 1 d . . . . .
C2B C 0.38661(5) 0.34694(5) 0.48170(15) 0.0190(3) Uani 1 1 d . . . . .
H2B H 0.379540 0.319799 0.452841 0.023 Uiso 1 1 calc R U . . .
C2N C 0.30689(5) 0.43485(5) 0.56207(14) 0.0173(3) Uani 1 1 d . . . . .
C2P C 0.48115(5) 0.36651(5) 0.67612(14) 0.0174(3) Uani 1 1 d . . . . .
C2T1 C 0.34964(5) 0.51214(5) 0.55901(18) 0.0267(4) Uani 0.964(2) 1 d D U P A 1
H2TA H 0.362187 0.512729 0.467999 0.032 Uiso 0.964(2) 1 calc R U P A 1
H2TB H 0.323643 0.512567 0.542045 0.032 Uiso 0.964(2) 1 calc R U P A 1
C2T2 C 0.3357(10) 0.5084(9) 0.686(5) 0.031(2) Uani 0.036(2) 1 d D U P A 2
H2TC H 0.312779 0.498176 0.753834 0.037 Uiso 0.036(2) 1 calc R U P A 2
H2TD H 0.328197 0.520266 0.606496 0.037 Uiso 0.036(2) 1 calc R U P A 2
C3B C 0.36625(5) 0.36579(5) 0.42358(15) 0.0189(3) Uani 1 1 d . . . . .
H3B H 0.345300 0.351382 0.356078 0.023 Uiso 1 1 calc R U . . .
C3P C 0.49819(5) 0.34486(5) 0.74096(16) 0.0233(3) Uani 1 1 d . . . . .
H3P H 0.526827 0.359056 0.763983 0.028 Uiso 1 1 calc R U . . .
C3T1 C 0.37936(6) 0.55052(6) 0.6414(2) 0.0359(5) Uani 0.964(2) 1 d D U P A 1
H3TA H 0.365571 0.551436 0.727948 0.043 Uiso 0.964(2) 1 calc R U P A 1
H3TB H 0.404003 0.548487 0.667337 0.043 Uiso 0.964(2) 1 calc R U P A 1
C3T2 C 0.3755(11) 0.5428(9) 0.753(5) 0.034(3) Uani 0.036(2) 1 d D U P A 2
H3TC H 0.398731 0.552701 0.686695 0.041 Uiso 0.036(2) 1 calc R U P A 2
H3TD H 0.382464 0.531534 0.835307 0.041 Uiso 0.036(2) 1 calc R U P A 2
C4B C 0.37619(4) 0.40578(5) 0.46320(14) 0.0168(3) Uani 1 1 d . . . . .
C4N C 0.27851(5) 0.38464(5) 0.40075(15) 0.0186(3) Uani 1 1 d . . . . .
C4P C 0.47416(5) 0.30321(5) 0.77217(16) 0.0244(3) Uani 1 1 d . . . . .
H4P H 0.486058 0.288878 0.816676 0.029 Uiso 1 1 calc R U . . .
C4T1 C 0.39333(8) 0.59045(6) 0.5609(3) 0.0588(7) Uani 0.964(2) 1 d D U P A 1
H4TA H 0.369141 0.593059 0.537414 0.088 Uiso 0.964(2) 1 calc R U P A 1
H4TB H 0.407337 0.589884 0.475684 0.088 Uiso 0.964(2) 1 calc R U P A 1
H4TC H 0.412525 0.614142 0.617825 0.088 Uiso 0.964(2) 1 calc R U P A 1
C4T2 C 0.3698(14) 0.5794(10) 0.798(6) 0.040(6) Uani 0.036(2) 1 d D U P A 2
H4TD H 0.347473 0.569785 0.866474 0.060 Uiso 0.036(2) 1 calc R U P A 2
H4TE H 0.362591 0.590340 0.716720 0.060 Uiso 0.036(2) 1 calc R U P A 2
H4TF H 0.395633 0.601213 0.838477 0.060 Uiso 0.036(2) 1 calc R U P A 2
C5 C 0.51115(5) 0.40997(5) 0.63972(14) 0.0173(3) Uani 1 1 d . . . . .
C5B C 0.40653(5) 0.42572(5) 0.56434(15) 0.0176(3) Uani 1 1 d . . . . .
H5B H 0.413767 0.452958 0.592570 0.021 Uiso 1 1 calc R U . . .
C5N C 0.24513(5) 0.38439(5) 0.49034(14) 0.0175(3) Uani 1 1 d . . . . .
C5P C 0.43251(5) 0.28266(5) 0.73767(15) 0.0214(3) Uani 1 1 d . . . . .
H5P H 0.415833 0.253885 0.756655 0.026 Uiso 1 1 calc R U . . .
C6B C 0.42629(5) 0.40653(4) 0.62435(14) 0.0169(3) Uani 1 1 d . . . . .
H6B H 0.446194 0.420401 0.695317 0.020 Uiso 1 1 calc R U . . .
C6N C 0.21422(5) 0.39195(5) 0.40888(15) 0.0208(3) Uani 1 1 d . . . . .
H6NA H 0.226392 0.421640 0.385073 0.025 Uiso 1 1 calc R U . . .
H6NB H 0.205573 0.375385 0.322531 0.025 Uiso 1 1 calc R U . . .
C6P C 0.41503(5) 0.30380(5) 0.67572(15) 0.0185(3) Uani 1 1 d . . . . .
H6P H 0.386306 0.289230 0.654030 0.022 Uiso 1 1 calc R U . . .
C7N C 0.17759(5) 0.37796(5) 0.50815(15) 0.0213(3) Uani 1 1 d . . . . .
H7NA H 0.151399 0.367991 0.456067 0.026 Uiso 1 1 calc R U . . .
H7NB H 0.181673 0.401064 0.569200 0.026 Uiso 1 1 calc R U . . .
C8N C 0.17660(5) 0.34251(5) 0.59365(15) 0.0205(3) Uani 1 1 d . . . . .
H8NA H 0.174966 0.347175 0.693867 0.025 Uiso 1 1 calc R U . . .
H8NB H 0.152286 0.315591 0.567664 0.025 Uiso 1 1 calc R U . . .
C9N C 0.21697(5) 0.34268(5) 0.56042(17) 0.0235(3) Uani 1 1 d . . . . .
H9NA H 0.229954 0.339966 0.646315 0.028 Uiso 1 1 calc R U . . .
H9NB H 0.211545 0.319495 0.497546 0.028 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
O1N C4N 1.2198(18) . ?
N1 H1 0.977(17) . ?
N1 N2 1.3516(17) . ?
N1 C5 1.3384(18) . ?
N1N C2N 1.2890(19) . ?
N1N C5N 1.4693(18) . ?
N2 N3 1.2963(17) . ?
N3 N4 1.3629(18) . ?
N3N C1M 1.4655(18) . ?
N3N C2N 1.3921(18) . ?
N3N C4N 1.3855(19) . ?
N4 C5 1.3246(19) . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 C2N 1.488(2) . ?
C1 C2T1 1.528(2) . ?
C1 C2T2 1.509(18) . ?
C1B C1P 1.484(2) . ?
C1B C2B 1.399(2) . ?
C1B C6B 1.396(2) . ?
C1M H1MA 0.9900 . ?
C1M H1MB 0.9900 . ?
C1M C4B 1.511(2) . ?
C1P C2P 1.409(2) . ?
C1P C6P 1.401(2) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.384(2) . ?
C2P C3P 1.399(2) . ?
C2P C5 1.477(2) . ?
C2T1 H2TA 0.9900 . ?
C2T1 H2TB 0.9900 . ?
C2T1 C3T1 1.523(2) . ?
C2T2 H2TC 0.9900 . ?
C2T2 H2TD 0.9900 . ?
C2T2 C3T2 1.539(19) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.397(2) . ?
C3P H3P 0.9500 . ?
C3P C4P 1.382(2) . ?
C3T1 H3TA 0.9900 . ?
C3T1 H3TB 0.9900 . ?
C3T1 C4T1 1.521(3) . ?
C3T2 H3TC 0.9900 . ?
C3T2 H3TD 0.9900 . ?
C3T2 C4T2 1.540(9) . ?
C4B C5B 1.394(2) . ?
C4N C5N 1.511(2) . ?
C4P H4P 0.9500 . ?
C4P C5P 1.384(2) . ?
C4T1 H4TA 0.9800 . ?
C4T1 H4TB 0.9800 . ?
C4T1 H4TC 0.9800 . ?
C4T2 H4TD 0.9800 . ?
C4T2 H4TE 0.9800 . ?
C4T2 H4TF 0.9800 . ?
C5B H5B 0.9500 . ?
C5B C6B 1.384(2) . ?
C5N C6N 1.532(2) . ?
C5N C9N 1.530(2) . ?
C5P H5P 0.9500 . ?
C5P C6P 1.383(2) . ?
C6B H6B 0.9500 . ?
C6N H6NA 0.9900 . ?
C6N H6NB 0.9900 . ?
C6N C7N 1.530(2) . ?
C6P H6P 0.9500 . ?
C7N H7NA 0.9900 . ?
C7N H7NB 0.9900 . ?
C7N C8N 1.542(2) . ?
C8N H8NA 0.9900 . ?
C8N H8NB 0.9900 . ?
C8N C9N 1.534(2) . ?
C9N H9NA 0.9900 . ?
C9N H9NB 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
N2 N1 H1 119.2(10) . . ?
C5 N1 H1 132.2(10) . . ?
C5 N1 N2 108.24(12) . . ?
C2N N1N C5N 107.82(12) . . ?
N3 N2 N1 106.51(12) . . ?
N2 N3 N4 110.88(12) . . ?
C2N N3N C1M 128.50(12) . . ?
C4N N3N C1M 123.23(12) . . ?
C4N N3N C2N 108.20(12) . . ?
C5 N4 N3 105.49(12) . . ?
H1AA C1 H1AB 107.9 . . ?
H1BC C1 H1BD 106.2 . . ?
C2N C1 H1AA 109.2 . . ?
C2N C1 H1AB 109.2 . . ?
C2N C1 H1BC 105.8 . . ?
C2N C1 H1BD 105.8 . . ?
C2N C1 C2T1 111.88(13) . . ?
C2N C1 C2T2 126.1(11) . . ?
C2T1 C1 H1AA 109.2 . . ?
C2T1 C1 H1AB 109.2 . . ?
C2T2 C1 H1BC 105.8 . . ?
C2T2 C1 H1BD 105.8 . . ?
C2B C1B C1P 120.39(13) . . ?
C6B C1B C1P 121.82(13) . . ?
C6B C1B C2B 117.76(14) . . ?
N3N C1M H1MA 108.8 . . ?
N3N C1M H1MB 108.8 . . ?
N3N C1M C4B 113.85(12) . . ?
H1MA C1M H1MB 107.7 . . ?
C4B C1M H1MA 108.8 . . ?
C4B C1M H1MB 108.8 . . ?
C2P C1P C1B 123.73(13) . . ?
C6P C1P C1B 118.80(13) . . ?
C6P C1P C2P 117.46(14) . . ?
C1B C2B H2B 119.4 . . ?
C3B C2B C1B 121.29(14) . . ?
C3B C2B H2B 119.4 . . ?
N1N C2N N3N 114.00(13) . . ?
N1N C2N C1 123.46(13) . . ?
N3N C2N C1 122.42(13) . . ?
C1P C2P C5 124.73(13) . . ?
C3P C2P C1P 120.02(14) . . ?
C3P C2P C5 115.17(13) . . ?
C1 C2T1 H2TA 109.2 . . ?
C1 C2T1 H2TB 109.2 . . ?
H2TA C2T1 H2TB 107.9 . . ?
C3T1 C2T1 C1 111.97(15) . . ?
C3T1 C2T1 H2TA 109.2 . . ?
C3T1 C2T1 H2TB 109.2 . . ?
C1 C2T2 H2TC 108.9 . . ?
C1 C2T2 H2TD 108.9 . . ?
C1 C2T2 C3T2 113.6(18) . . ?
H2TC C2T2 H2TD 107.7 . . ?
C3T2 C2T2 H2TC 108.9 . . ?
C3T2 C2T2 H2TD 108.9 . . ?
C2B C3B H3B 119.7 . . ?
C2B C3B C4B 120.65(14) . . ?
C4B C3B H3B 119.7 . . ?
C2P C3P H3P 119.4 . . ?
C4P C3P C2P 121.24(15) . . ?
C4P C3P H3P 119.4 . . ?
C2T1 C3T1 H3TA 109.1 . . ?
C2T1 C3T1 H3TB 109.1 . . ?
H3TA C3T1 H3TB 107.8 . . ?
C4T1 C3T1 C2T1 112.58(17) . . ?
C4T1 C3T1 H3TA 109.1 . . ?
C4T1 C3T1 H3TB 109.1 . . ?
C2T2 C3T2 H3TC 109.5 . . ?
C2T2 C3T2 H3TD 109.5 . . ?
C2T2 C3T2 C4T2 110.7(16) . . ?
H3TC C3T2 H3TD 108.1 . . ?
C4T2 C3T2 H3TC 109.5 . . ?
C4T2 C3T2 H3TD 109.5 . . ?
C3B C4B C1M 120.51(13) . . ?
C5B C4B C1M 121.24(13) . . ?
C5B C4B C3B 118.17(14) . . ?
O1N C4N N3N 125.52(14) . . ?
O1N C4N C5N 128.86(14) . . ?
N3N C4N C5N 105.62(12) . . ?
C3P C4P H4P 120.5 . . ?
C3P C4P C5P 119.08(15) . . ?
C5P C4P H4P 120.5 . . ?
C3T1 C4T1 H4TA 109.5 . . ?
C3T1 C4T1 H4TB 109.5 . . ?
C3T1 C4T1 H4TC 109.5 . . ?
H4TA C4T1 H4TB 109.5 . . ?
H4TA C4T1 H4TC 109.5 . . ?
H4TB C4T1 H4TC 109.5 . . ?
C3T2 C4T2 H4TD 109.5 . . ?
C3T2 C4T2 H4TE 109.5 . . ?
C3T2 C4T2 H4TF 109.5 . . ?
H4TD C4T2 H4TE 109.5 . . ?
H4TD C4T2 H4TF 109.5 . . ?
H4TE C4T2 H4TF 109.5 . . ?
N1 C5 C2P 126.22(13) . . ?
N4 C5 N1 108.88(13) . . ?
N4 C5 C2P 124.63(13) . . ?
C4B C5B H5B 119.4 . . ?
C6B C5B C4B 121.13(14) . . ?
C6B C5B H5B 119.4 . . ?
N1N C5N C4N 104.30(12) . . ?
N1N C5N C6N 110.96(12) . . ?
N1N C5N C9N 112.15(12) . . ?
C4N C5N C6N 113.39(12) . . ?
C4N C5N C9N 113.77(13) . . ?
C9N C5N C6N 102.53(12) . . ?
C4P C5P H5P 119.8 . . ?
C6P C5P C4P 120.37(14) . . ?
C6P C5P H5P 119.8 . . ?
C1B C6B H6B 119.5 . . ?
C5B C6B C1B 120.95(14) . . ?
C5B C6B H6B 119.5 . . ?
C5N C6N H6NA 111.0 . . ?
C5N C6N H6NB 111.0 . . ?
H6NA C6N H6NB 109.0 . . ?
C7N C6N C5N 103.89(12) . . ?
C7N C6N H6NA 111.0 . . ?
C7N C6N H6NB 111.0 . . ?
C1P C6P H6P 119.1 . . ?
C5P C6P C1P 121.79(14) . . ?
C5P C6P H6P 119.1 . . ?
C6N C7N H7NA 110.7 . . ?
C6N C7N H7NB 110.7 . . ?
C6N C7N C8N 105.20(12) . . ?
H7NA C7N H7NB 108.8 . . ?
C8N C7N H7NA 110.7 . . ?
C8N C7N H7NB 110.7 . . ?
C7N C8N H8NA 110.5 . . ?
C7N C8N H8NB 110.5 . . ?
H8NA C8N H8NB 108.7 . . ?
C9N C8N C7N 106.31(12) . . ?
C9N C8N H8NA 110.5 . . ?
C9N C8N H8NB 110.5 . . ?
C5N C9N C8N 105.62(12) . . ?
C5N C9N H9NA 110.6 . . ?
C5N C9N H9NB 110.6 . . ?
C8N C9N H9NA 110.6 . . ?
C8N C9N H9NB 110.6 . . ?
H9NA C9N H9NB 108.7 . . ?

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 N1N 0.977(17) 1.758(17) 2.7335(17) 176.1(17) 9_554 yes
C1M H1MA N3 0.99 2.53 3.466(2) 158.5 10_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1N C4N C5N N1N 178.12(15) . . . . ?
O1N C4N C5N C6N -61.1(2) . . . . ?
O1N C4N C5N C9N 55.6(2) . . . . ?
N1 N2 N3 N4 0.24(16) . . . . ?
N1N C5N C6N C7N -79.03(15) . . . . ?
N1N C5N C9N C8N 84.63(15) . . . . ?
N2 N1 C5 N4 -0.23(17) . . . . ?
N2 N1 C5 C2P -174.41(14) . . . . ?
N2 N3 N4 C5 -0.38(17) . . . . ?
N3 N4 C5 N1 0.36(16) . . . . ?
N3 N4 C5 C2P 174.65(14) . . . . ?
N3N C1M C4B C3B 84.57(17) . . . . ?
N3N C1M C4B C5B -98.76(16) . . . . ?
N3N C4N C5N N1N -2.21(15) . . . . ?
N3N C4N C5N C6N 118.61(13) . . . . ?
N3N C4N C5N C9N -124.72(13) . . . . ?
C1 C2T1 C3T1 C4T1 173.82(17) . . . . ?
C1 C2T2 C3T2 C4T2 178(4) . . . . ?
C1B C1P C2P C3P 176.73(13) . . . . ?
C1B C1P C2P C5 -6.6(2) . . . . ?
C1B C1P C6P C5P -177.90(13) . . . . ?
C1B C2B C3B C4B 0.5(2) . . . . ?
C1M N3N C2N N1N -177.33(13) . . . . ?
C1M N3N C2N C1 6.5(2) . . . . ?
C1M N3N C4N O1N -1.4(2) . . . . ?
C1M N3N C4N C5N 178.89(12) . . . . ?
C1M C4B C5B C6B -176.86(13) . . . . ?
C1P C1B C2B C3B 179.38(13) . . . . ?
C1P C1B C6B C5B 179.37(13) . . . . ?
C1P C2P C3P C4P 1.4(2) . . . . ?
C1P C2P C5 N1 -50.7(2) . . . . ?
C1P C2P C5 N4 135.95(16) . . . . ?
C2B C1B C1P C2P 141.41(15) . . . . ?
C2B C1B C1P C6P -40.0(2) . . . . ?
C2B C1B C6B C5B -2.8(2) . . . . ?
C2B C3B C4B C1M 175.60(13) . . . . ?
C2B C3B C4B C5B -1.2(2) . . . . ?
C2N N1N C5N C4N 2.18(15) . . . . ?
C2N N1N C5N C6N -120.25(13) . . . . ?
C2N N1N C5N C9N 125.74(14) . . . . ?
C2N N3N C1M C4B 85.80(18) . . . . ?
C2N N3N C4N O1N -178.81(14) . . . . ?
C2N N3N C4N C5N 1.51(15) . . . . ?
C2N C1 C2T1 C3T1 173.41(14) . . . . ?
C2N C1 C2T2 C3T2 -178(3) . . . . ?
C2P C1P C6P C5P 0.8(2) . . . . ?
C2P C3P C4P C5P 0.3(2) . . . . ?
C2T1 C1 C2N N1N -93.76(18) . . . . ?
C2T1 C1 C2N N3N 82.08(18) . . . . ?
C2T2 C1 C2N N1N -37(2) . . . . ?
C2T2 C1 C2N N3N 139(2) . . . . ?
C3B C4B C5B C6B -0.1(2) . . . . ?
C3P C2P C5 N1 126.04(16) . . . . ?
C3P C2P C5 N4 -47.3(2) . . . . ?
C3P C4P C5P C6P -1.5(2) . . . . ?
C4B C5B C6B C1B 2.1(2) . . . . ?
C4N N3N C1M C4B -91.03(17) . . . . ?
C4N N3N C2N N1N -0.13(17) . . . . ?
C4N N3N C2N C1 -176.32(13) . . . . ?
C4N C5N C6N C7N 163.98(12) . . . . ?
C4N C5N C9N C8N -157.29(12) . . . . ?
C4P C5P C6P C1P 0.9(2) . . . . ?
C5 N1 N2 N3 -0.01(16) . . . . ?
C5 C2P C3P C4P -175.57(14) . . . . ?
C5N N1N C2N N3N -1.37(17) . . . . ?
C5N N1N C2N C1 174.78(13) . . . . ?
C5N C6N C7N C8N -31.74(15) . . . . ?
C6B C1B C1P C2P -40.8(2) . . . . ?
C6B C1B C1P C6P 137.85(15) . . . . ?
C6B C1B C2B C3B 1.5(2) . . . . ?
C6N C5N C9N C8N -34.45(15) . . . . ?
C6N C7N C8N C9N 10.29(16) . . . . ?
C6P C1P C2P C3P -1.9(2) . . . . ?
C6P C1P C2P C5 174.72(13) . . . . ?
C7N C8N C9N C5N 15.08(16) . . . . ?
C9N C5N C6N C7N 40.88(15) . . . . ?

_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.375
_oxdiff_exptl_absorpt_empirical_full_min 0.522
####################################################################### 
# 
# 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_ibs_a_293k_zwitter
_database_code_depnum_ccdc_archive 'CCDC 1999413'
loop_
_audit_author_name
_audit_author_address
'Philippe Ochsenbein'
;Analytical Science Department, Sanofi Avensis, Montpellier
France
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2020-04-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_THETM01_ibs_a_293k_zwitter  
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was very thin and small and weakly-diffracting,
          perhaps also because of [001] channels in the structure. But
		  the defect is very minor and the quality of the structure is
		  certainly very good.
;
_chemical_name_common            SR47436-A
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 N6 O, 0.4[H2O]'
_chemical_formula_sum            'C25 H28 N6 O'
_chemical_formula_weight         428.52
_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   37.4596(7)
_cell_length_b                   37.4596(7)
_cell_length_c                   9.8361(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11953.1(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      57.3
_cell_measurement_theta_min      2.359
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.773
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  0.7513
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V2012/1 (Bruker AXS Inc.) was used for absorption correction.
wR2(int) was 0.1579 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.867.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             4104
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.016
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            37052
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        57.461
_diffrn_reflns_theta_max         57.461
_diffrn_reflns_theta_min         2.359
_diffrn_ambient_temperature      293(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX_DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec microsource'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3145
_reflns_number_total             3621
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'Bruker Instrument Service v2016.5.0.1'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.000036(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     170
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.116
_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)+(0.0754P)²+5.7706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1229
_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,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2T2-C1 \\sim C3T2-C2T2 \\sim C3T2-C4T2 \\sim C2T1-C1 \\sim C2T1-C3T1 \\sim
C4T1-C3T1
 with sigma of 0.01
 C1-C3T2 \\sim C4T2-C2T2 \\sim C1-C3T1 \\sim C4T1-C2T1
 with sigma of 0.01
 C2T2-C1 \\sim C2GT-C1 \\sim C3GT-C2GT \\sim C4GT-C3GT
 with sigma of 0.01
 C1-C3GT \\sim C4GT-C2GT
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2GT \\sim C2T1 \\sim C2T2 \\sim C3GT \\sim C3T1 \\sim C3T2 \\sim C4GT
\\sim C4T1 \\sim C4T2: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 1*[Sof(H1AA)+Sof(H1AB)+Sof(C2T2)+Sof(H2TC)+Sof(H2TD)+Sof(C3T2)+Sof(H3TC)+
 Sof(H3TD)+Sof(C4T2)+Sof(H4TD)+Sof(H4TE)+Sof(H4TF)]+1*[Sof(H1BC)+Sof(H1BD)+
 Sof(C2T1)+Sof(H2TA)+Sof(H2TB)+Sof(C3T1)+Sof(H3TA)+Sof(H3TB)+Sof(C4T1)+
 Sof(H4TA)+Sof(H4TB)+Sof(H4TC)]+1*[Sof(H1CE)+Sof(H1CF)+Sof(C2GT)+Sof(H2GA)+
 Sof(H2GB)+Sof(C3GT)+Sof(H3GA)+Sof(H3GB)+Sof(C4GT)+Sof(H4GA)+Sof(H4GB)+
 Sof(H4GC)]=1 with esd of 0.001
 Sof(H1AA)=Sof(H1AB)=Sof(C2T2)=Sof(H2TC)=Sof(H2TD)=Sof(C3T2)=Sof(H3TC)=
 Sof(H3TD)=Sof(C4T2)=Sof(H4TD)=Sof(H4TE)=Sof(H4TF)=FVAR(1)
 Sof(H1BC)=Sof(H1BD)=Sof(C2T1)=Sof(H2TA)=Sof(H2TB)=Sof(C3T1)=Sof(H3TA)=
 Sof(H3TB)=Sof(C4T1)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=FVAR(2)
 Sof(H1CE)=Sof(H1CF)=Sof(C2GT)=Sof(H2GA)=Sof(H2GB)=Sof(C3GT)=Sof(H3GA)=
 Sof(H3GB)=Sof(C4GT)=Sof(H4GA)=Sof(H4GB)=Sof(H4GC)=FVAR(3)
 Sof(H1N)=1-FVAR(4)
 Sof(H1)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1(H1CE,H1CF), C1M(H1MA,H1MB), C2GT(H2GA,H2GB),
 C2T1(H2TA,H2TB), C2T2(H2TC,H2TD), C3GT(H3GA,H3GB), C3T1(H3TA,H3TB), C3T2(H3TC,
 H3TD), C6N(H6NA,H6NB), C7N(H7NA,H7NB), C8N(H8NA,H8NB), C9N(H9NA,H9NB)
5.b Me refined with riding coordinates:
 C4GT(H4GA,H4GB,H4GC), C4T1(H4TA,H4TB,H4TC), C4T2(H4TD,H4TE,H4TF)
5.c Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C3P(H3P), C4P(H4P), C5B(H5B), C5P(H5P), C6B(H6B), C6P(H6P)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O1N O 0.72397(4) 0.63729(4) 0.68221(14) 0.0781(4) Uani 1 1 d . . . . .
N1 N 0.48418(4) 0.57596(4) 0.48599(16) 0.0534(4) Uani 1 1 d . . . . .
H1 H 0.4952(8) 0.5869(7) 0.568(3) 0.064 Uiso 0.79(3) 1 d . U P A 1
N1N N 0.72735(5) 0.57863(5) 0.40703(16) 0.0551(4) Uani 1 1 d . . . . .
H1N H 0.736(3) 0.577(3) 0.339(12) 0.066 Uiso 0.21(3) 1 d . U P A 2
N2 N 0.45229(4) 0.53704(4) 0.48346(16) 0.0636(4) Uani 1 1 d . . . . .
N3 N 0.43943(5) 0.52984(5) 0.35994(17) 0.0713(5) Uani 1 1 d . . . . .
N3N N 0.68184(4) 0.58206(4) 0.54596(13) 0.0490(4) Uani 1 1 d . . . . .
N4 N 0.46206(5) 0.56326(5) 0.28029(15) 0.0664(4) Uani 1 1 d . . . . .
C1 C 0.65530(6) 0.52572(6) 0.3702(2) 0.0744(6) Uani 1 1 d D U . . .
H1AA H 0.631963 0.513980 0.431874 0.089 Uiso 0.469(5) 1 calc R U P B 1
H1AB H 0.647111 0.535336 0.291046 0.089 Uiso 0.469(5) 1 calc R U P B 1
H1BC H 0.629216 0.524649 0.385889 0.089 Uiso 0.405(6) 1 calc R U P B 2
H1BD H 0.660181 0.527394 0.272976 0.089 Uiso 0.405(6) 1 calc R U P B 2
H1CE H 0.631605 0.529291 0.357204 0.089 Uiso 0.126(4) 1 calc R U P B 3
H1CF H 0.664382 0.521862 0.281881 0.089 Uiso 0.126(4) 1 calc R U P B 3
C1B C 0.58265(4) 0.63365(4) 0.41320(15) 0.0448(4) Uani 1 1 d . . . . .
C1M C 0.64232(5) 0.57339(5) 0.60491(17) 0.0558(4) Uani 1 1 d . . . . .
H1MA H 0.646610 0.581755 0.699591 0.067 Uiso 1 1 calc R U . . .
H1MB H 0.623423 0.543885 0.602174 0.067 Uiso 1 1 calc R U . . .
C1P C 0.56191(5) 0.65441(5) 0.35010(15) 0.0472(4) Uani 1 1 d . . . . .
C2B C 0.61275(5) 0.65334(5) 0.51188(17) 0.0529(4) Uani 1 1 d . . . . .
H2B H 0.619723 0.679828 0.539098 0.064 Uiso 1 1 calc R U . . .
C2GT C 0.6442(7) 0.4900(6) 0.456(3) 0.105(4) Uani 0.126(4) 1 d D U P B 3
H2GA H 0.635567 0.495753 0.542256 0.126 Uiso 0.126(4) 1 calc R U P B 3
H2GB H 0.619818 0.467335 0.415336 0.126 Uiso 0.126(4) 1 calc R U P B 3
C2N C 0.68908(5) 0.56266(5) 0.43820(16) 0.0514(4) Uani 1 1 d . . . . .
C2P C 0.51954(5) 0.63435(5) 0.32059(16) 0.0515(4) Uani 1 1 d . . . . .
C2T1 C 0.6535(2) 0.48811(15) 0.4250(10) 0.097(2) Uani 0.405(6) 1 d D U P B 2
H2TA H 0.680976 0.491741 0.418520 0.116 Uiso 0.405(6) 1 calc R U P B 2
H2TB H 0.646850 0.486448 0.520893 0.116 Uiso 0.405(6) 1 calc R U P B 2
C2T2 C 0.66159(16) 0.49229(14) 0.3257(8) 0.0917(16) Uani 0.469(5) 1 d D U P B 1
H2TC H 0.671376 0.483479 0.402860 0.110 Uiso 0.469(5) 1 calc R U P B 1
H2TD H 0.683405 0.503193 0.258231 0.110 Uiso 0.469(5) 1 calc R U P B 1
C3B C 0.63255(5) 0.63453(5) 0.57049(17) 0.0545(4) Uani 1 1 d . . . . .
H3B H 0.652785 0.648601 0.635750 0.065 Uiso 1 1 calc R U . . .
C3GT C 0.6713(6) 0.4743(6) 0.488(3) 0.124(4) Uani 0.126(4) 1 d D U P B 3
H3GA H 0.690655 0.492762 0.555470 0.149 Uiso 0.126(4) 1 calc R U P B 3
H3GB H 0.687166 0.477309 0.406713 0.149 Uiso 0.126(4) 1 calc R U P B 3
C3P C 0.50299(6) 0.65532(6) 0.2536(2) 0.0705(5) Uani 1 1 d . . . . .
H3P H 0.475111 0.641549 0.231568 0.085 Uiso 1 1 calc R U . . .
C3T1 C 0.6250(3) 0.44859(17) 0.3638(10) 0.125(2) Uani 0.405(6) 1 d D U P B 2
H3TA H 0.598895 0.447639 0.350577 0.151 Uiso 0.405(6) 1 calc R U P B 2
H3TB H 0.635491 0.447704 0.274406 0.151 Uiso 0.405(6) 1 calc R U P B 2
C3T2 C 0.6257(2) 0.45548(18) 0.2673(10) 0.127(2) Uani 0.469(5) 1 d D U P B 1
H3TC H 0.604397 0.443539 0.336209 0.152 Uiso 0.469(5) 1 calc R U P B 1
H3TD H 0.615001 0.464313 0.192791 0.152 Uiso 0.469(5) 1 calc R U P B 1
C4B C 0.62267(4) 0.59486(5) 0.53337(15) 0.0464(4) Uani 1 1 d . . . . .
C4GT C 0.6566(11) 0.4327(7) 0.538(4) 0.215(10) Uani 0.126(4) 1 d D U P B 3
H4GA H 0.679588 0.428555 0.552727 0.322 Uiso 0.126(4) 1 calc R U P B 3
H4GB H 0.641946 0.428754 0.621589 0.322 Uiso 0.126(4) 1 calc R U P B 3
H4GC H 0.638428 0.413173 0.471601 0.322 Uiso 0.126(4) 1 calc R U P B 3
C4N C 0.71912(5) 0.61378(5) 0.59056(17) 0.0536(4) Uani 1 1 d . . . . .
C4P C 0.52728(7) 0.69632(6) 0.2190(2) 0.0772(6) Uani 1 1 d . . . . .
H4P H 0.515848 0.710043 0.173897 0.093 Uiso 1 1 calc R U . . .
C4T1 C 0.6170(4) 0.4119(2) 0.4354(14) 0.228(6) Uani 0.405(6) 1 d D U P B 2
H4TA H 0.597839 0.388124 0.384474 0.342 Uiso 0.405(6) 1 calc R U P B 2
H4TB H 0.642317 0.411592 0.446606 0.342 Uiso 0.405(6) 1 calc R U P B 2
H4TC H 0.605569 0.411526 0.523094 0.342 Uiso 0.405(6) 1 calc R U P B 2
C4T2 C 0.6334(3) 0.4238(2) 0.2179(13) 0.214(5) Uani 0.469(5) 1 d D U P B 1
H4TD H 0.608259 0.401377 0.182247 0.322 Uiso 0.469(5) 1 calc R U P B 1
H4TE H 0.653760 0.434812 0.147243 0.322 Uiso 0.469(5) 1 calc R U P B 1
H4TF H 0.643127 0.413982 0.291052 0.322 Uiso 0.469(5) 1 calc R U P B 1
C5 C 0.48987(5) 0.59154(5) 0.36148(16) 0.0492(4) Uani 1 1 d . . . . .
C5B C 0.59313(5) 0.57541(5) 0.43374(16) 0.0508(4) Uani 1 1 d . . . . .
H5B H 0.586119 0.548874 0.407006 0.061 Uiso 1 1 calc R U . . .
C5N C 0.75136(5) 0.61228(5) 0.50292(15) 0.0493(4) Uani 1 1 d . . . . .
C5P C 0.56811(7) 0.71655(6) 0.25144(19) 0.0677(5) Uani 1 1 d . . . . .
H5P H 0.584390 0.744376 0.230523 0.081 Uiso 1 1 calc R U . . .
C6B C 0.57378(5) 0.59440(5) 0.37295(16) 0.0497(4) Uani 1 1 d . . . . .
H6B H 0.554609 0.580833 0.304318 0.060 Uiso 1 1 calc R U . . .
C6N C 0.78122(6) 0.60373(6) 0.58426(19) 0.0662(5) Uani 1 1 d . . . . .
H6NA H 0.788083 0.618209 0.670525 0.079 Uiso 1 1 calc R U . . .
H6NB H 0.769351 0.574453 0.601325 0.079 Uiso 1 1 calc R U . . .
C6P C 0.58542(5) 0.69610(5) 0.31496(17) 0.0563(4) Uani 1 1 d . . . . .
H6P H 0.613432 0.710332 0.335015 0.068 Uiso 1 1 calc R U . . .
C7N C 0.81887(6) 0.61963(7) 0.4944(2) 0.0763(6) Uani 1 1 d . . . . .
H7NA H 0.843448 0.628628 0.549178 0.092 Uiso 1 1 calc R U . . .
H7NB H 0.816230 0.598187 0.433003 0.092 Uiso 1 1 calc R U . . .
C8N C 0.82143(6) 0.65509(6) 0.4161(2) 0.0706(5) Uani 1 1 d . . . . .
H8NA H 0.827174 0.653152 0.321084 0.085 Uiso 1 1 calc R U . . .
H8NB H 0.843228 0.680980 0.452083 0.085 Uiso 1 1 calc R U . . .
C9N C 0.78004(5) 0.65275(6) 0.4310(2) 0.0662(5) Uani 1 1 d . . . . .
H9NA H 0.769066 0.653468 0.342416 0.079 Uiso 1 1 calc R U . . .
H9NB H 0.782917 0.675867 0.484110 0.079 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
O1N C4N 1.209(2) . ?
N1 H1 0.91(3) . ?
N1 N2 1.3460(19) . ?
N1 C5 1.327(2) . ?
N1N H1N 0.75(12) . ?
N1N C2N 1.284(2) . ?
N1N C5N 1.468(2) . ?
N2 N3 1.285(2) . ?
N3 N4 1.356(2) . ?
N3N C1M 1.467(2) . ?
N3N C2N 1.387(2) . ?
N3N C4N 1.377(2) . ?
N4 C5 1.320(2) . ?
C1 H1AA 0.9700 . ?
C1 H1AB 0.9700 . ?
C1 H1BC 0.9700 . ?
C1 H1BD 0.9700 . ?
C1 H1CE 0.9700 . ?
C1 H1CF 0.9700 . ?
C1 C2GT 1.454(8) . ?
C1 C2N 1.487(2) . ?
C1 C2T1 1.478(5) . ?
C1 C2T2 1.453(4) . ?
C1B C1P 1.483(2) . ?
C1B C2B 1.388(2) . ?
C1B C6B 1.393(2) . ?
C1M H1MA 0.9700 . ?
C1M H1MB 0.9700 . ?
C1M C4B 1.508(2) . ?
C1P C2P 1.406(2) . ?
C1P C6P 1.399(2) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.379(2) . ?
C2GT H2GA 0.9700 . ?
C2GT H2GB 0.9700 . ?
C2GT C3GT 1.442(8) . ?
C2P C3P 1.387(2) . ?
C2P C5 1.478(2) . ?
C2T1 H2TA 0.9700 . ?
C2T1 H2TB 0.9700 . ?
C2T1 C3T1 1.454(7) . ?
C2T2 H2TC 0.9700 . ?
C2T2 H2TD 0.9700 . ?
C2T2 C3T2 1.477(6) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.389(2) . ?
C3GT H3GA 0.9700 . ?
C3GT H3GB 0.9700 . ?
C3GT C4GT 1.453(8) . ?
C3P H3P 0.9300 . ?
C3P C4P 1.380(3) . ?
C3T1 H3TA 0.9700 . ?
C3T1 H3TB 0.9700 . ?
C3T1 C4T1 1.436(7) . ?
C3T2 H3TC 0.9700 . ?
C3T2 H3TD 0.9700 . ?
C3T2 C4T2 1.438(7) . ?
C4B C5B 1.382(2) . ?
C4GT H4GA 0.9600 . ?
C4GT H4GB 0.9600 . ?
C4GT H4GC 0.9600 . ?
C4N C5N 1.508(2) . ?
C4P H4P 0.9300 . ?
C4P C5P 1.362(3) . ?
C4T1 H4TA 0.9600 . ?
C4T1 H4TB 0.9600 . ?
C4T1 H4TC 0.9600 . ?
C4T2 H4TD 0.9600 . ?
C4T2 H4TE 0.9600 . ?
C4T2 H4TF 0.9600 . ?
C5B H5B 0.9300 . ?
C5B C6B 1.380(2) . ?
C5N C6N 1.534(2) . ?
C5N C9N 1.524(2) . ?
C5P H5P 0.9300 . ?
C5P C6P 1.377(3) . ?
C6B H6B 0.9300 . ?
C6N H6NA 0.9700 . ?
C6N H6NB 0.9700 . ?
C6N C7N 1.511(3) . ?
C6P H6P 0.9300 . ?
C7N H7NA 0.9700 . ?
C7N H7NB 0.9700 . ?
C7N C8N 1.496(3) . ?
C8N H8NA 0.9700 . ?
C8N H8NB 0.9700 . ?
C8N C9N 1.515(3) . ?
C9N H9NA 0.9700 . ?
C9N H9NB 0.9700 . ?

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
N2 N1 H1 117.6(15) . . ?
C5 N1 H1 133.3(15) . . ?
C5 N1 N2 108.65(14) . . ?
C2N N1N H1N 126(8) . . ?
C2N N1N C5N 107.99(14) . . ?
C5N N1N H1N 123(8) . . ?
N3 N2 N1 106.35(14) . . ?
N2 N3 N4 110.90(13) . . ?
C2N N3N C1M 128.77(14) . . ?
C4N N3N C1M 122.75(14) . . ?
C4N N3N C2N 108.44(13) . . ?
C5 N4 N3 105.65(14) . . ?
H1AA C1 H1AB 106.8 . . ?
H1BC C1 H1BD 108.2 . . ?
H1CE C1 H1CF 108.4 . . ?
C2GT C1 H1CE 110.0 . . ?
C2GT C1 H1CF 110.0 . . ?
C2GT C1 C2N 108.3(12) . . ?
C2N C1 H1AA 107.2 . . ?
C2N C1 H1AB 107.2 . . ?
C2N C1 H1BC 109.8 . . ?
C2N C1 H1BD 109.8 . . ?
C2N C1 H1CE 110.0 . . ?
C2N C1 H1CF 110.0 . . ?
C2T1 C1 H1BC 109.8 . . ?
C2T1 C1 H1BD 109.8 . . ?
C2T1 C1 C2N 109.6(3) . . ?
C2T2 C1 H1AA 107.2 . . ?
C2T2 C1 H1AB 107.2 . . ?
C2T2 C1 C2N 120.6(3) . . ?
C2B C1B C1P 120.89(14) . . ?
C2B C1B C6B 117.48(15) . . ?
C6B C1B C1P 121.60(14) . . ?
N3N C1M H1MA 108.8 . . ?
N3N C1M H1MB 108.8 . . ?
N3N C1M C4B 113.88(12) . . ?
H1MA C1M H1MB 107.7 . . ?
C4B C1M H1MA 108.8 . . ?
C4B C1M H1MB 108.8 . . ?
C2P C1P C1B 123.62(13) . . ?
C6P C1P C1B 119.10(14) . . ?
C6P C1P C2P 117.27(15) . . ?
C1B C2B H2B 119.3 . . ?
C3B C2B C1B 121.49(15) . . ?
C3B C2B H2B 119.3 . . ?
C1 C2GT H2GA 106.2 . . ?
C1 C2GT H2GB 106.2 . . ?
H2GA C2GT H2GB 106.4 . . ?
C3GT C2GT C1 124.6(18) . . ?
C3GT C2GT H2GA 106.2 . . ?
C3GT C2GT H2GB 106.2 . . ?
N1N C2N N3N 113.80(15) . . ?
N1N C2N C1 123.95(16) . . ?
N3N C2N C1 122.21(15) . . ?
C1P C2P C5 124.00(14) . . ?
C3P C2P C1P 120.02(15) . . ?
C3P C2P C5 115.93(15) . . ?
C1 C2T1 H2TA 107.6 . . ?
C1 C2T1 H2TB 107.6 . . ?
H2TA C2T1 H2TB 107.1 . . ?
C3T1 C2T1 C1 118.7(6) . . ?
C3T1 C2T1 H2TA 107.6 . . ?
C3T1 C2T1 H2TB 107.6 . . ?
C1 C2T2 H2TC 108.0 . . ?
C1 C2T2 H2TD 108.0 . . ?
C1 C2T2 C3T2 117.3(5) . . ?
H2TC C2T2 H2TD 107.2 . . ?
C3T2 C2T2 H2TC 108.0 . . ?
C3T2 C2T2 H2TD 108.0 . . ?
C2B C3B H3B 119.6 . . ?
C2B C3B C4B 120.89(15) . . ?
C4B C3B H3B 119.6 . . ?
C2GT C3GT H3GA 106.6 . . ?
C2GT C3GT H3GB 106.6 . . ?
C2GT C3GT C4GT 123(2) . . ?
H3GA C3GT H3GB 106.5 . . ?
C4GT C3GT H3GA 106.6 . . ?
C4GT C3GT H3GB 106.6 . . ?
C2P C3P H3P 119.5 . . ?
C4P C3P C2P 120.99(18) . . ?
C4P C3P H3P 119.5 . . ?
C2T1 C3T1 H3TA 107.8 . . ?
C2T1 C3T1 H3TB 107.8 . . ?
H3TA C3T1 H3TB 107.2 . . ?
C4T1 C3T1 C2T1 117.8(8) . . ?
C4T1 C3T1 H3TA 107.8 . . ?
C4T1 C3T1 H3TB 107.8 . . ?
C2T2 C3T2 H3TC 108.3 . . ?
C2T2 C3T2 H3TD 108.3 . . ?
H3TC C3T2 H3TD 107.4 . . ?
C4T2 C3T2 C2T2 116.0(6) . . ?
C4T2 C3T2 H3TC 108.3 . . ?
C4T2 C3T2 H3TD 108.3 . . ?
C3B C4B C1M 120.53(15) . . ?
C5B C4B C1M 121.69(14) . . ?
C5B C4B C3B 117.72(15) . . ?
C3GT C4GT H4GA 109.5 . . ?
C3GT C4GT H4GB 109.5 . . ?
C3GT C4GT H4GC 109.5 . . ?
H4GA C4GT H4GB 109.5 . . ?
H4GA C4GT H4GC 109.5 . . ?
H4GB C4GT H4GC 109.5 . . ?
O1N C4N N3N 125.77(16) . . ?
O1N C4N C5N 128.48(16) . . ?
N3N C4N C5N 105.75(14) . . ?
C3P C4P H4P 120.2 . . ?
C5P C4P C3P 119.58(18) . . ?
C5P C4P H4P 120.2 . . ?
C3T1 C4T1 H4TA 109.5 . . ?
C3T1 C4T1 H4TB 109.5 . . ?
C3T1 C4T1 H4TC 109.5 . . ?
H4TA C4T1 H4TB 109.5 . . ?
H4TA C4T1 H4TC 109.5 . . ?
H4TB C4T1 H4TC 109.5 . . ?
C3T2 C4T2 H4TD 109.5 . . ?
C3T2 C4T2 H4TE 109.5 . . ?
C3T2 C4T2 H4TF 109.5 . . ?
H4TD C4T2 H4TE 109.5 . . ?
H4TD C4T2 H4TF 109.5 . . ?
H4TE C4T2 H4TF 109.5 . . ?
N1 C5 C2P 126.61(14) . . ?
N4 C5 N1 108.45(14) . . ?
N4 C5 C2P 124.72(15) . . ?
C4B C5B H5B 119.2 . . ?
C6B C5B C4B 121.60(15) . . ?
C6B C5B H5B 119.2 . . ?
N1N C5N C4N 103.95(13) . . ?
N1N C5N C6N 110.72(14) . . ?
N1N C5N C9N 112.37(14) . . ?
C4N C5N C6N 113.02(14) . . ?
C4N C5N C9N 114.05(14) . . ?
C9N C5N C6N 102.99(14) . . ?
C4P C5P H5P 119.8 . . ?
C4P C5P C6P 120.45(17) . . ?
C6P C5P H5P 119.8 . . ?
C1B C6B H6B 119.6 . . ?
C5B C6B C1B 120.76(15) . . ?
C5B C6B H6B 119.6 . . ?
C5N C6N H6NA 110.9 . . ?
C5N C6N H6NB 110.9 . . ?
H6NA C6N H6NB 108.9 . . ?
C7N C6N C5N 104.30(14) . . ?
C7N C6N H6NA 110.9 . . ?
C7N C6N H6NB 110.9 . . ?
C1P C6P H6P 119.2 . . ?
C5P C6P C1P 121.63(17) . . ?
C5P C6P H6P 119.2 . . ?
C6N C7N H7NA 110.4 . . ?
C6N C7N H7NB 110.4 . . ?
H7NA C7N H7NB 108.6 . . ?
C8N C7N C6N 106.49(16) . . ?
C8N C7N H7NA 110.4 . . ?
C8N C7N H7NB 110.4 . . ?
C7N C8N H8NA 110.4 . . ?
C7N C8N H8NB 110.4 . . ?
C7N C8N C9N 106.80(15) . . ?
H8NA C8N H8NB 108.6 . . ?
C9N C8N H8NA 110.4 . . ?
C9N C8N H8NB 110.4 . . ?
C5N C9N H9NA 110.3 . . ?
C5N C9N H9NB 110.3 . . ?
C8N C9N C5N 107.13(14) . . ?
C8N C9N H9NA 110.3 . . ?
C8N C9N H9NB 110.3 . . ?
H9NA C9N H9NB 108.5 . . ?

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
N1 H1 N1N 0.91(3) 1.87(3) 2.775(2) 176(2) 6_565 yes
N1N H1N N1 0.75(12) 2.02(12) 2.775(2) 177(10) 8_654 yes
C1M H1MB N3 0.97 2.61 3.551(2) 163.8 10_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1N C4N C5N N1N -178.03(18) . . . . ?
O1N C4N C5N C6N 61.9(2) . . . . ?
O1N C4N C5N C9N -55.3(2) . . . . ?
N1 N2 N3 N4 -0.2(2) . . . . ?
N1N C5N C6N C7N 85.31(18) . . . . ?
N1N C5N C9N C8N -92.94(18) . . . . ?
N2 N1 C5 N4 0.27(19) . . . . ?
N2 N1 C5 C2P 175.09(16) . . . . ?
N2 N3 N4 C5 0.3(2) . . . . ?
N3 N4 C5 N1 -0.37(19) . . . . ?
N3 N4 C5 C2P -175.31(16) . . . . ?
N3N C1M C4B C3B -87.23(18) . . . . ?
N3N C1M C4B C5B 95.70(18) . . . . ?
N3N C4N C5N N1N 2.47(16) . . . . ?
N3N C4N C5N C6N -117.63(16) . . . . ?
N3N C4N C5N C9N 125.18(15) . . . . ?
C1 C2GT C3GT C4GT -161(3) . . . . ?
C1 C2T1 C3T1 C4T1 -166.7(10) . . . . ?
C1 C2T2 C3T2 C4T2 177.0(8) . . . . ?
C1B C1P C2P C3P -175.88(16) . . . . ?
C1B C1P C2P C5 6.6(2) . . . . ?
C1B C1P C6P C5P 177.50(15) . . . . ?
C1B C2B C3B C4B -0.6(2) . . . . ?
C1M N3N C2N N1N 177.22(15) . . . . ?
C1M N3N C2N C1 -5.1(3) . . . . ?
C1M N3N C4N O1N 1.3(3) . . . . ?
C1M N3N C4N C5N -179.21(13) . . . . ?
C1M C4B C5B C6B 176.88(14) . . . . ?
C1P C1B C2B C3B -179.39(14) . . . . ?
C1P C1B C6B C5B -179.41(14) . . . . ?
C1P C2P C3P C4P -2.3(3) . . . . ?
C1P C2P C5 N1 53.2(2) . . . . ?
C1P C2P C5 N4 -132.78(18) . . . . ?
C2B C1B C1P C2P -139.65(16) . . . . ?
C2B C1B C1P C6P 41.6(2) . . . . ?
C2B C1B C6B C5B 2.7(2) . . . . ?
C2B C3B C4B C1M -175.68(14) . . . . ?
C2B C3B C4B C5B 1.5(2) . . . . ?
C2GT C1 C2N N1N 99.6(10) . . . . ?
C2GT C1 C2N N3N -77.8(10) . . . . ?
C2N N1N C5N C4N -2.78(17) . . . . ?
C2N N1N C5N C6N 118.87(15) . . . . ?
C2N N1N C5N C9N -126.59(15) . . . . ?
C2N N3N C1M C4B -85.6(2) . . . . ?
C2N N3N C4N O1N 179.11(17) . . . . ?
C2N N3N C4N C5N -1.38(17) . . . . ?
C2N C1 C2GT C3GT -64(3) . . . . ?
C2N C1 C2T1 C3T1 -174.5(7) . . . . ?
C2N C1 C2T2 C3T2 176.0(5) . . . . ?
C2P C1P C6P C5P -1.4(2) . . . . ?
C2P C3P C4P C5P -0.1(3) . . . . ?
C2T1 C1 C2N N1N 79.1(4) . . . . ?
C2T1 C1 C2N N3N -98.3(4) . . . . ?
C2T2 C1 C2N N1N 35.9(4) . . . . ?
C2T2 C1 C2N N3N -141.5(4) . . . . ?
C3B C4B C5B C6B -0.3(2) . . . . ?
C3P C2P C5 N1 -124.41(19) . . . . ?
C3P C2P C5 N4 49.6(2) . . . . ?
C3P C4P C5P C6P 1.8(3) . . . . ?
C4B C5B C6B C1B -1.9(2) . . . . ?
C4N N3N C1M C4B 91.81(18) . . . . ?
C4N N3N C2N N1N -0.45(19) . . . . ?
C4N N3N C2N C1 177.21(16) . . . . ?
C4N C5N C6N C7N -158.53(16) . . . . ?
C4N C5N C9N C8N 149.08(15) . . . . ?
C4P C5P C6P C1P -1.0(3) . . . . ?
C5 N1 N2 N3 -0.05(19) . . . . ?
C5 C2P C3P C4P 175.46(18) . . . . ?
C5N N1N C2N N3N 2.12(19) . . . . ?
C5N N1N C2N C1 -175.49(16) . . . . ?
C5N C6N C7N C8N 31.3(2) . . . . ?
C6B C1B C1P C2P 42.5(2) . . . . ?
C6B C1B C1P C6P -136.25(16) . . . . ?
C6B C1B C2B C3B -1.5(2) . . . . ?
C6N C5N C9N C8N 26.23(19) . . . . ?
C6N C7N C8N C9N -14.8(2) . . . . ?
C6P C1P C2P C3P 2.9(2) . . . . ?
C6P C1P C2P C5 -174.59(15) . . . . ?
C7N C8N C9N C5N -7.5(2) . . . . ?
C9N C5N C6N C7N -35.00(19) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.803 475.7 21.9 '2.4 water'
2 0.333 0.667 -0.288 475.7 21.9 '2.4 water'
3 0.667 0.333 -0.621 475.7 21.9 '2.4 water'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ibs_a_114k_wet_ind_ox
_database_code_depnum_ccdc_archive 'CCDC 2268210'
loop_
_audit_author_name
_audit_author_address
'Farzaneh Fadaei Tirani'
;EPFL
Switzerland
;
_audit_update_record             
;
2024-02-25 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2024-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
# start Validation Reply Form
_vrf_CHEMW01_ibs_a_114k_wet_ind_ox 
;
PROBLEM: The difference between the given and expected weight for
RESPONSE: ...
;
_vrf_PLAT029_ibs_a_114k_wet_ind_ox 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.935 Why?  
RESPONSE: This slight defect must be due to the tiny size and high aspect
          ratio of the measured crystal. Also, no strong scatterer was 
          present in this compound.
;
_vrf_PLAT041_ibs_a_114k_wet_ind_ox 
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: This difference is due to the fact that we indicated water in the
          sum formula, but we were unable to locate the correspoding
		  hydrogens in difference maps.
;
_vrf_PLAT042_ibs_a_114k_wet_ind_ox 
;
PROBLEM: Calc. and Reported MoietyFormula Strings  Differ     Please Check 
RESPONSE: This difference is due to the fact that we indicated water in the
          sum formula, but we were unable to locate the correspoding
		  hydrogens in difference maps.
;
_chemical_name_common            SR47436-A
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 N6 O1, H2O'
_chemical_formula_sum            'C25 H30 N6 O2'
_chemical_formula_weight         444.53
_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   37.2565(10)
_cell_length_b                   37.2565(10)
_cell_length_c                   9.6925(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11651.2(7)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    114(2)
_cell_measurement_theta_max      66.242
_cell_measurement_theta_min      2.372
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.794
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V2012/1 (Bruker AXS Inc.) was used for absorption correction.
wR2(int) was 0.1579 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.867.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             4248
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            35318
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.182
_diffrn_reflns_theta_max         67.182
_diffrn_reflns_theta_min         2.372
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.934
_diffrn_ambient_temperature      114.00
_diffrn_detector_area_resol_mean 8.3333
_diffrn_detector_type            'APEX II'
_diffrn_measurement_device_type  'Bruker APEX_DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3641
_reflns_number_total             4329
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2016.5.0.1'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4329
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.046
_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)+(0.0607P)²+11.9114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1200
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2T1-C1 \\sim C2T2-C1 \\sim C2T1-C3T1 \\sim C2T2-C3T2 \\sim C4T1-C3T1 \\sim
C4T2-C3T2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2T1 \\sim C2T2 \\sim C3T1 \\sim C3T2 \\sim C4T1 \\sim C4T2: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 O2, O5, O6, O4, O1, O3, O7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 1*[Sof(O1)]+1*[Sof(O2)]+1*[Sof(O4)]+1*[Sof(O5)]+1*[Sof(O6)]+1*[Sof(O7)]+1*
 [Sof(O3)]=1 with esd of 0.001
 Sof(H1BC)=Sof(H1BD)=Sof(C2T2)=Sof(H2TC)=Sof(H2TD)=Sof(C3T2)=Sof(H3TC)=
 Sof(H3TD)=Sof(C4T2)=Sof(H4TD)=Sof(H4TE)=Sof(H4TF)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C2T1)=Sof(H2TA)=Sof(H2TB)=Sof(C3T1)=Sof(H3TA)=
 Sof(H3TB)=Sof(C4T1)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1M(H1MA,H1MB), C2T1(H2TA,H2TB), C2T2(H2TC,
 H2TD), C3T1(H3TA,H3TB), C3T2(H3TC,H3TD), C6N(H6NA,H6NB), C7N(H7NA,H7NB),
 C8N(H8NA,H8NB), C9N(H9NA,H9NB)
6.b Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C3P(H3P), C4P(H4P), C5B(H5B), C5P(H5P), C6B(H6B), C6P(H6P)
6.c Idealised Me refined as rotating group:
 C4T1(H4TA,H4TB,H4TC), C4T2(H4TD,H4TE,H4TF)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.4538(7) 0.7157(6) -0.169(2) 0.179(11) Uiso 0.224(13) 1 d . . P A 3
O3 O 0.4336(11) 0.7068(10) -0.303(4) 0.18(2) Uiso 0.137(16) 1 d . . P B 9
O4 O 0.408(2) 0.707(2) -0.094(6) 0.30(3) Uiso 0.16(2) 1 d . . P C 5
O7 O 0.3825(18) 0.641(3) -0.393(7) 0.56(4) Uiso 0.30(2) 1 d . . P D 8
O1N O 0.63792(4) 0.72515(4) -0.19434(13) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.57303(4) 0.48363(4) 0.01430(16) 0.0281(3) Uani 1 1 d . . . . .
H1 H 0.5837(6) 0.4959(6) -0.072(2) 0.034 Uiso 1 1 d . U . . .
N1N N 0.58195(4) 0.73157(4) 0.09166(15) 0.0303(3) Uani 1 1 d . . . . .
N2 N 0.53412(4) 0.45098(4) 0.02020(15) 0.0313(3) Uani 1 1 d . . . . .
N3 N 0.52840(4) 0.43740(4) 0.14581(16) 0.0336(4) Uani 1 1 d . . . . .
N3N N 0.58299(4) 0.68431(4) -0.04971(14) 0.0272(3) Uani 1 1 d . . . . .
N4 N 0.56294(4) 0.46039(4) 0.22352(15) 0.0324(3) Uani 1 1 d . . . . .
C1 C 0.52752(5) 0.65991(5) 0.13348(19) 0.0346(4) Uani 1 1 d D U . . .
H1AA H 0.526684 0.668997 0.228834 0.042 Uiso 0.941(3) 1 calc R U P E 1
H1AB H 0.529416 0.634381 0.138996 0.042 Uiso 0.941(3) 1 calc R U P E 1
H1BC H 0.537927 0.652155 0.215634 0.042 Uiso 0.059(3) 1 calc R U P E 2
H1BD H 0.515839 0.635577 0.071309 0.042 Uiso 0.059(3) 1 calc R U P E 2
C1B C 0.63310(5) 0.58275(5) 0.08198(17) 0.0262(4) Uani 1 1 d . . . . .
C1M C 0.57256(5) 0.64374(5) -0.10740(18) 0.0292(4) Uani 1 1 d . . . . .
H1MA H 0.579872 0.647189 -0.206593 0.035 Uiso 1 1 calc R U . . .
H1MB H 0.542247 0.624944 -0.100123 0.035 Uiso 1 1 calc R U . . .
C1P C 0.65407(5) 0.56153(5) 0.14445(17) 0.0269(4) Uani 1 1 d . . . . .
C2B C 0.65309(5) 0.61326(5) -0.01796(18) 0.0293(4) Uani 1 1 d . . . . .
H2B H 0.680193 0.620269 -0.046885 0.035 Uiso 1 1 calc R U . . .
C2N C 0.56488(5) 0.69279(5) 0.06208(17) 0.0283(4) Uani 1 1 d . . . . .
C2P C 0.63371(5) 0.51889(5) 0.17618(17) 0.0283(4) Uani 1 1 d . . . . .
C2T1 C 0.48774(5) 0.65033(6) 0.0591(2) 0.0408(5) Uani 0.941(3) 1 d D U P E 1
H2TA H 0.487079 0.638071 -0.032139 0.049 Uiso 0.941(3) 1 calc R U P E 1
H2TB H 0.487502 0.676470 0.043517 0.049 Uiso 0.941(3) 1 calc R U P E 1
C2T2 C 0.4910(6) 0.6636(8) 0.183(4) 0.044(4) Uani 0.059(3) 1 d D U P E 2
H2TC H 0.479417 0.671313 0.103980 0.053 Uiso 0.059(3) 1 calc R U P E 2
H2TD H 0.500830 0.686159 0.251917 0.053 Uiso 0.059(3) 1 calc R U P E 2
C3B C 0.63417(5) 0.63361(5) -0.07606(18) 0.0293(4) Uani 1 1 d . . . . .
H3B H 0.648565 0.654550 -0.143295 0.035 Uiso 1 1 calc R U . . .
C3P C 0.65518(5) 0.50197(5) 0.24173(19) 0.0347(4) Uani 1 1 d . . . . .
H3P H 0.640975 0.473367 0.265010 0.042 Uiso 1 1 calc R U . . .
C3T1 C 0.44925(6) 0.62051(7) 0.1404(3) 0.0534(7) Uani 0.941(3) 1 d D U P E 1
H3TA H 0.451230 0.595840 0.166120 0.064 Uiso 0.941(3) 1 calc R U P E 1
H3TB H 0.448129 0.634177 0.226548 0.064 Uiso 0.941(3) 1 calc R U P E 1
C3T2 C 0.4568(9) 0.6239(8) 0.247(5) 0.049(5) Uani 0.059(3) 1 d D U P E 2
H3TC H 0.468942 0.614098 0.318357 0.059 Uiso 0.059(3) 1 calc R U P E 2
H3TD H 0.444212 0.602269 0.175139 0.059 Uiso 0.059(3) 1 calc R U P E 2
C4B C 0.59434(5) 0.62368(5) -0.03687(17) 0.0271(4) Uani 1 1 d . . . . .
C4N C 0.61518(5) 0.72126(5) -0.09845(18) 0.0289(4) Uani 1 1 d . . . . .
C4P C 0.69672(5) 0.52609(6) 0.2733(2) 0.0371(4) Uani 1 1 d . . . . .
H4P H 0.710977 0.514204 0.318239 0.045 Uiso 1 1 calc R U . . .
C4T1 C 0.40952(7) 0.60668(9) 0.0589(4) 0.0815(10) Uani 0.941(3) 1 d D U P E 1
H4TA H 0.385688 0.587168 0.114338 0.122 Uiso 0.941(3) 1 calc R U P E 1
H4TB H 0.410456 0.593096 -0.026543 0.122 Uiso 0.941(3) 1 calc R U P E 1
H4TC H 0.406838 0.630879 0.036354 0.122 Uiso 0.941(3) 1 calc R U P E 1
C4T2 C 0.4234(10) 0.6305(12) 0.312(5) 0.062(9) Uani 0.059(3) 1 d D U P E 2
H4TD H 0.435186 0.649575 0.390434 0.093 Uiso 0.059(3) 1 calc R U P E 2
H4TE H 0.400724 0.603819 0.344843 0.093 Uiso 0.059(3) 1 calc R U P E 2
H4TF H 0.412843 0.642176 0.243741 0.093 Uiso 0.059(3) 1 calc R U P E 2
C5 C 0.59030(5) 0.48894(5) 0.13902(17) 0.0268(4) Uani 1 1 d . . . . .
C5B C 0.57438(5) 0.59346(5) 0.06414(17) 0.0278(4) Uani 1 1 d . . . . .
H5B H 0.547176 0.586302 0.092294 0.033 Uiso 1 1 calc R U . . .
C5N C 0.61530(5) 0.75459(5) -0.00899(17) 0.0275(4) Uani 1 1 d . . . . .
C5P C 0.71738(5) 0.56765(5) 0.23912(18) 0.0328(4) Uani 1 1 d . . . . .
H5P H 0.746119 0.584301 0.258568 0.039 Uiso 1 1 calc R U . . .
C6B C 0.59360(5) 0.57370(5) 0.12417(17) 0.0271(4) Uani 1 1 d . . . . .
H6B H 0.579747 0.553774 0.194772 0.033 Uiso 1 1 calc R U . . .
C6N C 0.60753(5) 0.78543(5) -0.09024(19) 0.0317(4) Uani 1 1 d . . . . .
H6NA H 0.623870 0.793942 -0.176684 0.038 Uiso 1 1 calc R U . . .
H6NB H 0.577788 0.773233 -0.113127 0.038 Uiso 1 1 calc R U . . .
C6P C 0.69632(5) 0.58513(5) 0.17654(17) 0.0294(4) Uani 1 1 d . . . . .
H6P H 0.710889 0.613840 0.154828 0.035 Uiso 1 1 calc R U . . .
C7N C 0.62176(5) 0.82220(5) 0.00803(19) 0.0332(4) Uani 1 1 d . . . . .
H7NA H 0.598785 0.818222 0.069253 0.040 Uiso 1 1 calc R U . . .
H7NB H 0.631601 0.848287 -0.044289 0.040 Uiso 1 1 calc R U . . .
C8N C 0.65734(5) 0.82343(5) 0.09256(19) 0.0317(4) Uani 1 1 d . . . . .
H8NA H 0.684200 0.847597 0.065443 0.038 Uiso 1 1 calc R U . . .
H8NB H 0.652961 0.825477 0.192334 0.038 Uiso 1 1 calc R U . . .
C9N C 0.65698(5) 0.78294(5) 0.0611(2) 0.0348(4) Uani 1 1 d . . . . .
H9NA H 0.659577 0.770149 0.147215 0.042 Uiso 1 1 calc R U . . .
H9NB H 0.680204 0.788163 -0.000999 0.042 Uiso 1 1 calc R U . . .
O2 O 0.3948(14) 0.6306(13) 0.468(4) 0.12(2) Uiso 0.081(16) 1 d . . P F 4
O5 O 0.333333 0.666667 0.166667 0.50(8) Uiso 0.39(8) 6 d S . P G 6
O6 O 0.333333 0.666667 0.00(2) 0.40(17) Uiso 0.09(4) 3 d S . P H 7


_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
O1N C4N 1.216(2) . ?
N1 H1 0.94(2) . ?
N1 N2 1.3496(18) . ?
N1 C5 1.337(2) . ?
N1N C2N 1.287(2) . ?
N1N C5N 1.472(2) . ?
N2 N3 1.295(2) . ?
N3 N4 1.362(2) . ?
N3N C1M 1.470(2) . ?
N3N C2N 1.394(2) . ?
N3N C4N 1.380(2) . ?
N4 C5 1.326(2) . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 C2N 1.487(2) . ?
C1 C2T1 1.521(3) . ?
C1 C2T2 1.512(8) . ?
C1B C1P 1.490(2) . ?
C1B C2B 1.392(2) . ?
C1B C6B 1.397(2) . ?
C1M H1MA 0.9900 . ?
C1M H1MB 0.9900 . ?
C1M C4B 1.514(2) . ?
C1P C2P 1.410(2) . ?
C1P C6P 1.401(2) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.387(2) . ?
C2P C3P 1.395(2) . ?
C2P C5 1.479(2) . ?
C2T1 H2TA 0.9900 . ?
C2T1 H2TB 0.9900 . ?
C2T1 C3T1 1.522(3) . ?
C2T2 H2TC 0.9900 . ?
C2T2 H2TD 0.9900 . ?
C2T2 C3T2 1.519(9) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.391(2) . ?
C3P H3P 0.9500 . ?
C3P C4P 1.381(2) . ?
C3T1 H3TA 0.9900 . ?
C3T1 H3TB 0.9900 . ?
C3T1 C4T1 1.523(3) . ?
C3T2 H3TC 0.9900 . ?
C3T2 H3TD 0.9900 . ?
C3T2 C4T2 1.520(9) . ?
C4B C5B 1.393(2) . ?
C4N C5N 1.513(2) . ?
C4P H4P 0.9500 . ?
C4P C5P 1.382(2) . ?
C4T1 H4TA 0.9800 . ?
C4T1 H4TB 0.9800 . ?
C4T1 H4TC 0.9800 . ?
C4T2 H4TD 0.9800 . ?
C4T2 H4TE 0.9800 . ?
C4T2 H4TF 0.9800 . ?
C5B H5B 0.9500 . ?
C5B C6B 1.386(2) . ?
C5N C6N 1.535(2) . ?
C5N C9N 1.532(2) . ?
C5P H5P 0.9500 . ?
C5P C6P 1.385(2) . ?
C6B H6B 0.9500 . ?
C6N H6NA 0.9900 . ?
C6N H6NB 0.9900 . ?
C6N C7N 1.529(2) . ?
C6P H6P 0.9500 . ?
C7N H7NA 0.9900 . ?
C7N H7NB 0.9900 . ?
C7N C8N 1.539(2) . ?
C8N H8NA 0.9900 . ?
C8N H8NB 0.9900 . ?
C8N C9N 1.532(2) . ?
C9N H9NA 0.9900 . ?
C9N H9NB 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
N2 N1 H1 118.5(11) . . ?
C5 N1 H1 132.7(11) . . ?
C5 N1 N2 108.40(14) . . ?
C2N N1N C5N 107.82(13) . . ?
N3 N2 N1 106.55(13) . . ?
N2 N3 N4 110.81(13) . . ?
C2N N3N C1M 128.30(13) . . ?
C4N N3N C1M 123.12(14) . . ?
C4N N3N C2N 108.52(13) . . ?
C5 N4 N3 105.58(14) . . ?
H1AA C1 H1AB 107.9 . . ?
H1BC C1 H1BD 106.2 . . ?
C2N C1 H1AA 109.2 . . ?
C2N C1 H1AB 109.2 . . ?
C2N C1 H1BC 105.8 . . ?
C2N C1 H1BD 105.8 . . ?
C2N C1 C2T1 111.94(15) . . ?
C2N C1 C2T2 126.0(9) . . ?
C2T1 C1 H1AA 109.2 . . ?
C2T1 C1 H1AB 109.2 . . ?
C2T2 C1 H1BC 105.8 . . ?
C2T2 C1 H1BD 105.8 . . ?
C2B C1B C1P 120.50(14) . . ?
C2B C1B C6B 118.02(15) . . ?
C6B C1B C1P 121.45(14) . . ?
N3N C1M H1MA 108.8 . . ?
N3N C1M H1MB 108.8 . . ?
N3N C1M C4B 113.87(13) . . ?
H1MA C1M H1MB 107.7 . . ?
C4B C1M H1MA 108.8 . . ?
C4B C1M H1MB 108.8 . . ?
C2P C1P C1B 123.85(14) . . ?
C6P C1P C1B 118.68(14) . . ?
C6P C1P C2P 117.46(15) . . ?
C1B C2B H2B 119.4 . . ?
C3B C2B C1B 121.21(15) . . ?
C3B C2B H2B 119.4 . . ?
N1N C2N N3N 113.85(14) . . ?
N1N C2N C1 123.69(15) . . ?
N3N C2N C1 122.34(14) . . ?
C1P C2P C5 124.49(15) . . ?
C3P C2P C1P 120.10(15) . . ?
C3P C2P C5 115.34(14) . . ?
C1 C2T1 H2TA 109.2 . . ?
C1 C2T1 H2TB 109.2 . . ?
C1 C2T1 C3T1 112.19(18) . . ?
H2TA C2T1 H2TB 107.9 . . ?
C3T1 C2T1 H2TA 109.2 . . ?
C3T1 C2T1 H2TB 109.2 . . ?
C1 C2T2 H2TC 108.9 . . ?
C1 C2T2 H2TD 108.9 . . ?
C1 C2T2 C3T2 113.4(15) . . ?
H2TC C2T2 H2TD 107.7 . . ?
C3T2 C2T2 H2TC 108.9 . . ?
C3T2 C2T2 H2TD 108.9 . . ?
C2B C3B H3B 119.7 . . ?
C2B C3B C4B 120.67(15) . . ?
C4B C3B H3B 119.7 . . ?
C2P C3P H3P 119.4 . . ?
C4P C3P C2P 121.10(16) . . ?
C4P C3P H3P 119.4 . . ?
C2T1 C3T1 H3TA 109.1 . . ?
C2T1 C3T1 H3TB 109.1 . . ?
H3TA C3T1 H3TB 107.9 . . ?
C4T1 C3T1 C2T1 112.3(2) . . ?
C4T1 C3T1 H3TA 109.1 . . ?
C4T1 C3T1 H3TB 109.1 . . ?
C2T2 C3T2 H3TC 109.3 . . ?
C2T2 C3T2 H3TD 109.3 . . ?
C2T2 C3T2 C4T2 112(2) . . ?
H3TC C3T2 H3TD 107.9 . . ?
C4T2 C3T2 H3TC 109.3 . . ?
C4T2 C3T2 H3TD 109.3 . . ?
C3B C4B C1M 120.62(15) . . ?
C3B C4B C5B 118.31(15) . . ?
C5B C4B C1M 121.00(14) . . ?
O1N C4N N3N 125.90(15) . . ?
O1N C4N C5N 128.62(15) . . ?
N3N C4N C5N 105.48(14) . . ?
C3P C4P H4P 120.3 . . ?
C3P C4P C5P 119.42(16) . . ?
C5P C4P H4P 120.3 . . ?
C3T1 C4T1 H4TA 109.5 . . ?
C3T1 C4T1 H4TB 109.5 . . ?
C3T1 C4T1 H4TC 109.5 . . ?
H4TA C4T1 H4TB 109.5 . . ?
H4TA C4T1 H4TC 109.5 . . ?
H4TB C4T1 H4TC 109.5 . . ?
C3T2 C4T2 H4TD 109.5 . . ?
C3T2 C4T2 H4TE 109.5 . . ?
C3T2 C4T2 H4TF 109.5 . . ?
H4TD C4T2 H4TE 109.5 . . ?
H4TD C4T2 H4TF 109.5 . . ?
H4TE C4T2 H4TF 109.5 . . ?
N1 C5 C2P 126.58(15) . . ?
N4 C5 N1 108.66(14) . . ?
N4 C5 C2P 124.55(15) . . ?
C4B C5B H5B 119.5 . . ?
C6B C5B C4B 121.03(14) . . ?
C6B C5B H5B 119.5 . . ?
N1N C5N C4N 104.28(12) . . ?
N1N C5N C6N 110.85(13) . . ?
N1N C5N C9N 112.17(14) . . ?
C4N C5N C6N 113.33(14) . . ?
C4N C5N C9N 113.95(13) . . ?
C9N C5N C6N 102.50(13) . . ?
C4P C5P H5P 119.9 . . ?
C4P C5P C6P 120.20(15) . . ?
C6P C5P H5P 119.9 . . ?
C1B C6B H6B 119.6 . . ?
C5B C6B C1B 120.71(15) . . ?
C5B C6B H6B 119.6 . . ?
C5N C6N H6NA 111.0 . . ?
C5N C6N H6NB 111.0 . . ?
H6NA C6N H6NB 109.0 . . ?
C7N C6N C5N 103.90(13) . . ?
C7N C6N H6NA 111.0 . . ?
C7N C6N H6NB 111.0 . . ?
C1P C6P H6P 119.2 . . ?
C5P C6P C1P 121.66(15) . . ?
C5P C6P H6P 119.2 . . ?
C6N C7N H7NA 110.7 . . ?
C6N C7N H7NB 110.7 . . ?
C6N C7N C8N 105.43(13) . . ?
H7NA C7N H7NB 108.8 . . ?
C8N C7N H7NA 110.7 . . ?
C8N C7N H7NB 110.7 . . ?
C7N C8N H8NA 110.5 . . ?
C7N C8N H8NB 110.5 . . ?
H8NA C8N H8NB 108.7 . . ?
C9N C8N C7N 106.32(13) . . ?
C9N C8N H8NA 110.5 . . ?
C9N C8N H8NB 110.5 . . ?
C5N C9N H9NA 110.6 . . ?
C5N C9N H9NB 110.6 . . ?
C8N C9N C5N 105.91(13) . . ?
C8N C9N H9NA 110.6 . . ?
C8N C9N H9NB 110.6 . . ?
H9NA C9N H9NB 108.7 . . ?

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 N1N 0.94(2) 1.80(2) 2.742(2) 177(2) 8_654 yes
C1M H1MB N3 0.99 2.53 3.472(2) 158.7 10_665 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
O1N C4N C5N N1N -178.35(16) . . . . ?
O1N C4N C5N C6N 61.0(2) . . . . ?
O1N C4N C5N C9N -55.7(2) . . . . ?
N1 N2 N3 N4 -0.22(17) . . . . ?
N1N C5N C6N C7N 79.66(16) . . . . ?
N1N C5N C9N C8N -85.32(16) . . . . ?
N2 N1 C5 N4 -0.30(17) . . . . ?
N2 N1 C5 C2P 174.58(15) . . . . ?
N2 N3 N4 C5 0.04(18) . . . . ?
N3 N4 C5 N1 0.16(17) . . . . ?
N3 N4 C5 C2P -174.85(15) . . . . ?
N3N C1M C4B C3B -84.58(19) . . . . ?
N3N C1M C4B C5B 98.43(17) . . . . ?
N3N C4N C5N N1N 2.22(16) . . . . ?
N3N C4N C5N C6N -118.43(15) . . . . ?
N3N C4N C5N C9N 124.85(15) . . . . ?
C1 C2T1 C3T1 C4T1 -173.0(2) . . . . ?
C1 C2T2 C3T2 C4T2 172(3) . . . . ?
C1B C1P C2P C3P -176.38(16) . . . . ?
C1B C1P C2P C5 6.6(3) . . . . ?
C1B C1P C6P C5P 177.74(15) . . . . ?
C1B C2B C3B C4B -0.7(2) . . . . ?
C1M N3N C2N N1N 177.29(14) . . . . ?
C1M N3N C2N C1 -6.5(2) . . . . ?
C1M N3N C4N O1N 1.6(3) . . . . ?
C1M N3N C4N C5N -178.92(14) . . . . ?
C1M C4B C5B C6B 176.97(15) . . . . ?
C1P C1B C2B C3B -179.31(15) . . . . ?
C1P C1B C6B C5B -179.43(15) . . . . ?
C1P C2P C3P C4P -1.8(3) . . . . ?
C1P C2P C5 N1 50.6(2) . . . . ?
C1P C2P C5 N4 -135.28(18) . . . . ?
C2B C1B C1P C2P -140.93(17) . . . . ?
C2B C1B C1P C6P 40.4(2) . . . . ?
C2B C1B C6B C5B 2.4(2) . . . . ?
C2B C3B C4B C1M -175.70(15) . . . . ?
C2B C3B C4B C5B 1.4(2) . . . . ?
C2N N1N C5N C4N -2.28(17) . . . . ?
C2N N1N C5N C6N 120.01(15) . . . . ?
C2N N1N C5N C9N -126.07(15) . . . . ?
C2N N3N C1M C4B -86.00(19) . . . . ?
C2N N3N C4N O1N 179.12(16) . . . . ?
C2N N3N C4N C5N -1.43(17) . . . . ?
C2N C1 C2T1 C3T1 -173.20(16) . . . . ?
C2N C1 C2T2 C3T2 178(2) . . . . ?
C2P C1P C6P C5P -1.0(2) . . . . ?
C2P C3P C4P C5P -0.2(3) . . . . ?
C2T1 C1 C2N N1N 92.9(2) . . . . ?
C2T1 C1 C2N N3N -82.95(19) . . . . ?
C2T2 C1 C2N N1N 37.2(18) . . . . ?
C2T2 C1 C2N N3N -138.6(18) . . . . ?
C3B C4B C5B C6B -0.1(2) . . . . ?
C3P C2P C5 N1 -126.56(18) . . . . ?
C3P C2P C5 N4 47.5(2) . . . . ?
C3P C4P C5P C6P 1.5(3) . . . . ?
C4B C5B C6B C1B -1.8(2) . . . . ?
C4N N3N C1M C4B 90.98(19) . . . . ?
C4N N3N C2N N1N -0.04(19) . . . . ?
C4N N3N C2N C1 176.15(15) . . . . ?
C4N C5N C6N C7N -163.49(13) . . . . ?
C4N C5N C9N C8N 156.48(14) . . . . ?
C4P C5P C6P C1P -0.9(3) . . . . ?
C5 N1 N2 N3 0.32(17) . . . . ?
C5 C2P C3P C4P 175.53(16) . . . . ?
C5N N1N C2N N3N 1.54(18) . . . . ?
C5N N1N C2N C1 -174.59(15) . . . . ?
C5N C6N C7N C8N 31.67(17) . . . . ?
C6B C1B C1P C2P 41.0(2) . . . . ?
C6B C1B C1P C6P -137.71(16) . . . . ?
C6B C1B C2B C3B -1.2(2) . . . . ?
C6N C5N C9N C8N 33.63(17) . . . . ?
C6N C7N C8N C9N -10.72(18) . . . . ?
C6P C1P C2P C3P 2.3(2) . . . . ?
C6P C1P C2P C5 -174.71(15) . . . . ?
C7N C8N C9N C5N -14.37(18) . . . . ?
C9N C5N C6N C7N -40.22(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ibs_a_114k_dry_zwitter
_database_code_depnum_ccdc_archive 'CCDC 1999411'
loop_
_audit_author_name
_audit_author_address
'Philippe Ochsenbein'
;Analytical Science Department, Sanofi Avensis, Montpellier
France
;
_audit_update_record             
;
2020-04-27 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2020-04-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
# start Validation Reply Form
_vrf_THETM01_ibs_a_114k_dry_zwitter 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was very thin and small and weakly-diffracting,
          perhaps also because of [001] channels in the structure. But
		  the defect is very minor and the quality of the structure is
		  certainly very good.
;
_vrf_PLAT602_ibs_a_114k_dry_zwitter 
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info  
RESPONSE: There are endless [001] channels in the structure.
;
_chemical_name_common            SR47436-A
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 N6 O'
_chemical_formula_sum            'C25 H28 N6 O'
_chemical_formula_weight         428.53
_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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   37.2303(4)
_cell_length_b                   37.2303(4)
_cell_length_c                   9.70850(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11654.0(3)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    8932
_cell_measurement_temperature    114(1)
_cell_measurement_theta_max      55.711
_cell_measurement_theta_min      2.374
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  0.7513
_exptl_absorpt_correction_T_min  0.5099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS V2012/1 (Bruker AXS Inc.) was used for absorption correction.
wR2(int) was 0.1579 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.867.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             4104
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.016
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1109
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            50223
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        57.469
_diffrn_reflns_theta_max         57.469
_diffrn_reflns_theta_min         2.373
_diffrn_ambient_temperature      114.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX_DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec microsource'
_diffrn_source_current           0.64
_diffrn_source_power             0.0285824
_diffrn_source_voltage           44.66
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2649
_reflns_number_total             3448
_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_data_collection       'Bruker Instrument Service v2016.5.0.1'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.000026(6)
_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   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.020
_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)+(0.0399P)²+29.9515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1146
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2T1-C1 \\sim C2T2-C1 \\sim C2T1-C3T1 \\sim C2T2-C3T2 \\sim C4T1-C3T1 \\sim
C4T2-C3T2
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2T1 \\sim C2T2 \\sim C3T1 \\sim C3T2 \\sim C4T1 \\sim C4T2: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(H1BC)=Sof(H1BD)=Sof(C2T2)=Sof(H2TC)=Sof(H2TD)=Sof(C3T2)=Sof(H3TC)=
 Sof(H3TD)=Sof(C4T2)=Sof(H4TD)=Sof(H4TE)=Sof(H4TF)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C2T1)=Sof(H2TA)=Sof(H2TB)=Sof(C3T1)=Sof(H3TA)=
 Sof(H3TB)=Sof(C4T1)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=FVAR(1)
 Sof(H1N)=1-FVAR(2)
 Sof(H1)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1M(H1MA,H1MB), C2T1(H2TA,H2TB), C2T2(H2TC,
 H2TD), C3T1(H3TA,H3TB), C3T2(H3TC,H3TD), C6N(H6NA,H6NB), C7N(H7NA,H7NB),
 C8N(H8NA,H8NB), C9N(H9NA,H9NB)
5.b Aromatic/amide H refined with riding coordinates:
 N1N(H1N), C2B(H2B), C3B(H3B), C3P(H3P), C4P(H4P), C5B(H5B), C5P(H5P),
 C6B(H6B), C6P(H6P)
5.c Idealised Me refined as rotating group:
 C4T1(H4TA,H4TB,H4TC), C4T2(H4TD,H4TE,H4TF)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O1N O 0.63812(5) 0.72532(5) -0.19441(18) 0.0332(5) Uani 1 1 d . . . . .
N1 N 0.57316(6) 0.48362(6) 0.0134(2) 0.0250(5) Uani 1 1 d . . . . .
H1 H 0.5840(9) 0.4971(10) -0.073(3) 0.030 Uiso 0.79(4) 1 d . U P A 1
N1N N 0.58223(6) 0.73168(6) 0.0915(2) 0.0262(5) Uani 1 1 d . . . . .
H1N H 0.575257 0.742512 0.159771 0.031 Uiso 0.21(4) 1 calc R U P . .
N2 N 0.53409(6) 0.45092(6) 0.0191(2) 0.0285(5) Uani 1 1 d . . . . .
N3 N 0.52835(6) 0.43712(6) 0.1445(2) 0.0302(5) Uani 1 1 d . . . . .
N3N N 0.58313(6) 0.68427(5) -0.0497(2) 0.0224(5) Uani 1 1 d . . . . .
N4 N 0.56289(6) 0.46016(6) 0.2229(2) 0.0287(5) Uani 1 1 d . . . . .
C1 C 0.52770(7) 0.65980(8) 0.1339(3) 0.0315(6) Uani 1 1 d D U . . .
H1AA H 0.527106 0.668821 0.229357 0.038 Uiso 0.918(3) 1 calc R U P B 1
H1AB H 0.529455 0.634158 0.138506 0.038 Uiso 0.918(3) 1 calc R U P B 1
H1BC H 0.538138 0.651774 0.215216 0.038 Uiso 0.082(3) 1 calc R U P B 2
H1BD H 0.515583 0.635512 0.071490 0.038 Uiso 0.082(3) 1 calc R U P B 2
C1B C 0.63324(7) 0.58269(7) 0.0818(2) 0.0216(6) Uani 1 1 d . . . . .
C1M C 0.57288(7) 0.64387(7) -0.1080(3) 0.0250(6) Uani 1 1 d . . . . .
H1MA H 0.580541 0.647529 -0.206736 0.030 Uiso 1 1 calc R U . . .
H1MB H 0.542524 0.625032 -0.101878 0.030 Uiso 1 1 calc R U . . .
C1P C 0.65407(7) 0.56141(7) 0.1445(2) 0.0227(6) Uani 1 1 d . . . . .
C2B C 0.65337(7) 0.61334(7) -0.0176(2) 0.0252(6) Uani 1 1 d . . . . .
H2B H 0.680552 0.620431 -0.045960 0.030 Uiso 1 1 calc R U . . .
C2N C 0.56509(7) 0.69274(7) 0.0619(2) 0.0237(6) Uani 1 1 d . . . . .
C2P C 0.63371(7) 0.51867(7) 0.1758(2) 0.0241(6) Uani 1 1 d . . . . .
C2T1 C 0.48793(8) 0.65057(9) 0.0607(3) 0.0378(8) Uani 0.918(3) 1 d D U P B 1
H2TA H 0.486931 0.638168 -0.030408 0.045 Uiso 0.918(3) 1 calc R U P B 1
H2TB H 0.487954 0.676867 0.045258 0.045 Uiso 0.918(3) 1 calc R U P B 1
C2T2 C 0.4917(7) 0.6643(8) 0.185(4) 0.039(4) Uani 0.082(3) 1 d D U P B 2
H2TC H 0.479671 0.671770 0.106424 0.047 Uiso 0.082(3) 1 calc R U P B 2
H2TD H 0.501904 0.687028 0.253127 0.047 Uiso 0.082(3) 1 calc R U P B 2
C3B C 0.63444(7) 0.63375(7) -0.0761(3) 0.0253(6) Uani 1 1 d . . . . .
H3B H 0.648824 0.654683 -0.143291 0.030 Uiso 1 1 calc R U . . .
C3P C 0.65508(7) 0.50166(8) 0.2414(3) 0.0307(6) Uani 1 1 d . . . . .
H3P H 0.640870 0.473041 0.264602 0.037 Uiso 1 1 calc R U . . .
C3T1 C 0.44950(8) 0.62109(10) 0.1427(4) 0.0501(10) Uani 0.918(3) 1 d D U P B 1
H3TA H 0.451101 0.596134 0.167462 0.060 Uiso 0.918(3) 1 calc R U P B 1
H3TB H 0.448847 0.634823 0.229177 0.060 Uiso 0.918(3) 1 calc R U P B 1
C3T2 C 0.4584(9) 0.6244(8) 0.250(5) 0.047(5) Uani 0.082(3) 1 d D U P B 2
H3TC H 0.447443 0.601638 0.181495 0.056 Uiso 0.082(3) 1 calc R U P B 2
H3TD H 0.470234 0.616533 0.327967 0.056 Uiso 0.082(3) 1 calc R U P B 2
C4B C 0.59449(7) 0.62369(7) -0.0367(2) 0.0222(6) Uani 1 1 d . . . . .
C4N C 0.61533(7) 0.72141(7) -0.0984(3) 0.0247(6) Uani 1 1 d . . . . .
C4P C 0.69676(8) 0.52595(8) 0.2731(3) 0.0329(7) Uani 1 1 d . . . . .
H4P H 0.711059 0.514095 0.317932 0.039 Uiso 1 1 calc R U . . .
C4T1 C 0.40969(10) 0.60792(12) 0.0627(5) 0.0821(14) Uani 0.918(3) 1 d D U P B 1
H4TA H 0.385830 0.588804 0.118801 0.123 Uiso 0.918(3) 1 calc R U P B 1
H4TB H 0.410048 0.594036 -0.022648 0.123 Uiso 0.918(3) 1 calc R U P B 1
H4TC H 0.407536 0.632448 0.040299 0.123 Uiso 0.918(3) 1 calc R U P B 1
C4T2 C 0.4239(10) 0.6315(11) 0.301(4) 0.058(8) Uani 0.082(3) 1 d D U P B 2
H4TD H 0.435203 0.654360 0.367170 0.087 Uiso 0.082(3) 1 calc R U P B 2
H4TE H 0.402371 0.606231 0.344958 0.087 Uiso 0.082(3) 1 calc R U P B 2
H4TF H 0.411976 0.638545 0.222386 0.087 Uiso 0.082(3) 1 calc R U P B 2
C5 C 0.59036(7) 0.48891(7) 0.1385(2) 0.0227(6) Uani 1 1 d . . . . .
C5B C 0.57458(7) 0.59349(7) 0.0635(2) 0.0235(6) Uani 1 1 d . . . . .
H5B H 0.547326 0.586292 0.091360 0.028 Uiso 1 1 calc R U . . .
C5N C 0.61552(7) 0.75477(7) -0.0094(2) 0.0229(6) Uani 1 1 d . . . . .
C5P C 0.71735(7) 0.56748(8) 0.2391(3) 0.0295(6) Uani 1 1 d . . . . .
H5P H 0.746097 0.584121 0.258675 0.035 Uiso 1 1 calc R U . . .
C6B C 0.59365(7) 0.57366(7) 0.1237(2) 0.0236(6) Uani 1 1 d . . . . .
H6B H 0.579728 0.553726 0.194171 0.028 Uiso 1 1 calc R U . . .
C6N C 0.60760(8) 0.78561(7) -0.0899(3) 0.0268(6) Uani 1 1 d . . . . .
H6NA H 0.623878 0.794198 -0.176373 0.032 Uiso 1 1 calc R U . . .
H6NB H 0.577809 0.773354 -0.112483 0.032 Uiso 1 1 calc R U . . .
C6P C 0.69649(7) 0.58502(7) 0.1768(2) 0.0261(6) Uani 1 1 d . . . . .
H6P H 0.711144 0.613755 0.155252 0.031 Uiso 1 1 calc R U . . .
C7N C 0.62181(8) 0.82226(7) 0.0082(3) 0.0301(6) Uani 1 1 d . . . . .
H7NA H 0.598825 0.818236 0.069450 0.036 Uiso 1 1 calc R U . . .
H7NB H 0.631637 0.848394 -0.043834 0.036 Uiso 1 1 calc R U . . .
C8N C 0.65746(7) 0.82348(7) 0.0925(3) 0.0274(6) Uani 1 1 d . . . . .
H8NA H 0.684337 0.847669 0.065419 0.033 Uiso 1 1 calc R U . . .
H8NB H 0.653102 0.825466 0.192124 0.033 Uiso 1 1 calc R U . . .
C9N C 0.65706(7) 0.78297(7) 0.0606(3) 0.0316(6) Uani 1 1 d . . . . .
H9NA H 0.680318 0.788235 -0.001367 0.038 Uiso 1 1 calc R U . . .
H9NB H 0.659613 0.770082 0.146424 0.038 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
O1N C4N 1.219(3) . ?
N1 H1 0.96(3) . ?
N1 N2 1.353(3) . ?
N1 C5 1.341(3) . ?
N1N H1N 0.8800 . ?
N1N C2N 1.291(3) . ?
N1N C5N 1.473(3) . ?
N2 N3 1.298(3) . ?
N3 N4 1.365(3) . ?
N3N C1M 1.468(3) . ?
N3N C2N 1.392(3) . ?
N3N C4N 1.384(3) . ?
N4 C5 1.330(3) . ?
C1 H1AA 0.9900 . ?
C1 H1AB 0.9900 . ?
C1 H1BC 0.9900 . ?
C1 H1BD 0.9900 . ?
C1 C2N 1.491(3) . ?
C1 C2T1 1.519(3) . ?
C1 C2T2 1.513(8) . ?
C1B C1P 1.488(3) . ?
C1B C2B 1.393(3) . ?
C1B C6B 1.398(3) . ?
C1M H1MA 0.9900 . ?
C1M H1MB 0.9900 . ?
C1M C4B 1.515(3) . ?
C1P C2P 1.412(3) . ?
C1P C6P 1.406(3) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.390(3) . ?
C2P C3P 1.394(3) . ?
C2P C5 1.475(3) . ?
C2T1 H2TA 0.9900 . ?
C2T1 H2TB 0.9900 . ?
C2T1 C3T1 1.521(4) . ?
C2T2 H2TC 0.9900 . ?
C2T2 H2TD 0.9900 . ?
C2T2 C3T2 1.519(9) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.393(3) . ?
C3P H3P 0.9500 . ?
C3P C4P 1.384(3) . ?
C3T1 H3TA 0.9900 . ?
C3T1 H3TB 0.9900 . ?
C3T1 C4T1 1.521(4) . ?
C3T2 H3TC 0.9900 . ?
C3T2 H3TD 0.9900 . ?
C3T2 C4T2 1.517(9) . ?
C4B C5B 1.389(3) . ?
C4N C5N 1.510(3) . ?
C4P H4P 0.9500 . ?
C4P C5P 1.379(3) . ?
C4T1 H4TA 0.9800 . ?
C4T1 H4TB 0.9800 . ?
C4T1 H4TC 0.9800 . ?
C4T2 H4TD 0.9800 . ?
C4T2 H4TE 0.9800 . ?
C4T2 H4TF 0.9800 . ?
C5B H5B 0.9500 . ?
C5B C6B 1.384(3) . ?
C5N C6N 1.535(3) . ?
C5N C9N 1.527(3) . ?
C5P H5P 0.9500 . ?
C5P C6P 1.379(3) . ?
C6B H6B 0.9500 . ?
C6N H6NA 0.9900 . ?
C6N H6NB 0.9900 . ?
C6N C7N 1.526(3) . ?
C6P H6P 0.9500 . ?
C7N H7NA 0.9900 . ?
C7N H7NB 0.9900 . ?
C7N C8N 1.540(3) . ?
C8N H8NA 0.9900 . ?
C8N H8NB 0.9900 . ?
C8N C9N 1.532(3) . ?
C9N H9NA 0.9900 . ?
C9N H9NB 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
N2 N1 H1 119.2(19) . . ?
C5 N1 H1 132.3(19) . . ?
C5 N1 N2 108.3(2) . . ?
C2N N1N H1N 126.1 . . ?
C2N N1N C5N 107.86(19) . . ?
C5N N1N H1N 126.1 . . ?
N3 N2 N1 106.54(19) . . ?
N2 N3 N4 110.94(18) . . ?
C2N N3N C1M 128.66(19) . . ?
C4N N3N C1M 123.0(2) . . ?
C4N N3N C2N 108.32(19) . . ?
C5 N4 N3 105.44(19) . . ?
H1AA C1 H1AB 107.9 . . ?
H1BC C1 H1BD 106.3 . . ?
C2N C1 H1AA 109.3 . . ?
C2N C1 H1AB 109.3 . . ?
C2N C1 H1BC 106.0 . . ?
C2N C1 H1BD 106.0 . . ?
C2N C1 C2T1 111.8(2) . . ?
C2N C1 C2T2 125.1(10) . . ?
C2T1 C1 H1AA 109.3 . . ?
C2T1 C1 H1AB 109.3 . . ?
C2T2 C1 H1BC 106.0 . . ?
C2T2 C1 H1BD 106.0 . . ?
C2B C1B C1P 120.6(2) . . ?
C2B C1B C6B 118.0(2) . . ?
C6B C1B C1P 121.3(2) . . ?
N3N C1M H1MA 108.8 . . ?
N3N C1M H1MB 108.8 . . ?
N3N C1M C4B 113.70(19) . . ?
H1MA C1M H1MB 107.7 . . ?
C4B C1M H1MA 108.8 . . ?
C4B C1M H1MB 108.8 . . ?
C2P C1P C1B 124.0(2) . . ?
C6P C1P C1B 118.7(2) . . ?
C6P C1P C2P 117.3(2) . . ?
C1B C2B H2B 119.4 . . ?
C3B C2B C1B 121.2(2) . . ?
C3B C2B H2B 119.4 . . ?
N1N C2N N3N 113.8(2) . . ?
N1N C2N C1 123.6(2) . . ?
N3N C2N C1 122.4(2) . . ?
C1P C2P C5 124.3(2) . . ?
C3P C2P C1P 120.2(2) . . ?
C3P C2P C5 115.4(2) . . ?
C1 C2T1 H2TA 109.2 . . ?
C1 C2T1 H2TB 109.2 . . ?
C1 C2T1 C3T1 112.2(3) . . ?
H2TA C2T1 H2TB 107.9 . . ?
C3T1 C2T1 H2TA 109.2 . . ?
C3T1 C2T1 H2TB 109.2 . . ?
C1 C2T2 H2TC 109.4 . . ?
C1 C2T2 H2TD 109.4 . . ?
C1 C2T2 C3T2 111.2(15) . . ?
H2TC C2T2 H2TD 108.0 . . ?
C3T2 C2T2 H2TC 109.4 . . ?
C3T2 C2T2 H2TD 109.4 . . ?
C2B C3B H3B 119.8 . . ?
C2B C3B C4B 120.4(2) . . ?
C4B C3B H3B 119.8 . . ?
C2P C3P H3P 119.6 . . ?
C4P C3P C2P 120.9(2) . . ?
C4P C3P H3P 119.6 . . ?
C2T1 C3T1 H3TA 109.2 . . ?
C2T1 C3T1 H3TB 109.2 . . ?
H3TA C3T1 H3TB 107.9 . . ?
C4T1 C3T1 C2T1 112.3(3) . . ?
C4T1 C3T1 H3TA 109.2 . . ?
C4T1 C3T1 H3TB 109.2 . . ?
C2T2 C3T2 H3TC 110.1 . . ?
C2T2 C3T2 H3TD 110.1 . . ?
H3TC C3T2 H3TD 108.4 . . ?
C4T2 C3T2 C2T2 108(2) . . ?
C4T2 C3T2 H3TC 110.1 . . ?
C4T2 C3T2 H3TD 110.1 . . ?
C3B C4B C1M 120.1(2) . . ?
C5B C4B C1M 121.4(2) . . ?
C5B C4B C3B 118.4(2) . . ?
O1N C4N N3N 125.7(2) . . ?
O1N C4N C5N 128.5(2) . . ?
N3N C4N C5N 105.8(2) . . ?
C3P C4P H4P 120.3 . . ?
C5P C4P C3P 119.5(2) . . ?
C5P C4P H4P 120.3 . . ?
C3T1 C4T1 H4TA 109.5 . . ?
C3T1 C4T1 H4TB 109.5 . . ?
C3T1 C4T1 H4TC 109.5 . . ?
H4TA C4T1 H4TB 109.5 . . ?
H4TA C4T1 H4TC 109.5 . . ?
H4TB C4T1 H4TC 109.5 . . ?
C3T2 C4T2 H4TD 109.5 . . ?
C3T2 C4T2 H4TE 109.5 . . ?
C3T2 C4T2 H4TF 109.5 . . ?
H4TD C4T2 H4TE 109.5 . . ?
H4TD C4T2 H4TF 109.5 . . ?
H4TE C4T2 H4TF 109.5 . . ?
N1 C5 C2P 126.5(2) . . ?
N4 C5 N1 108.7(2) . . ?
N4 C5 C2P 124.5(2) . . ?
C4B C5B H5B 119.4 . . ?
C6B C5B C4B 121.3(2) . . ?
C6B C5B H5B 119.4 . . ?
N1N C5N C4N 104.12(18) . . ?
N1N C5N C6N 110.79(19) . . ?
N1N C5N C9N 111.9(2) . . ?
C4N C5N C6N 113.6(2) . . ?
C4N C5N C9N 114.00(19) . . ?
C9N C5N C6N 102.67(19) . . ?
C4P C5P H5P 119.8 . . ?
C6P C5P C4P 120.5(2) . . ?
C6P C5P H5P 119.8 . . ?
C1B C6B H6B 119.7 . . ?
C5B C6B C1B 120.6(2) . . ?
C5B C6B H6B 119.7 . . ?
C5N C6N H6NA 111.0 . . ?
C5N C6N H6NB 111.0 . . ?
H6NA C6N H6NB 109.0 . . ?
C7N C6N C5N 103.92(19) . . ?
C7N C6N H6NA 111.0 . . ?
C7N C6N H6NB 111.0 . . ?
C1P C6P H6P 119.2 . . ?
C5P C6P C1P 121.6(2) . . ?
C5P C6P H6P 119.2 . . ?
C6N C7N H7NA 110.7 . . ?
C6N C7N H7NB 110.7 . . ?
C6N C7N C8N 105.45(19) . . ?
H7NA C7N H7NB 108.8 . . ?
C8N C7N H7NA 110.7 . . ?
C8N C7N H7NB 110.7 . . ?
C7N C8N H8NA 110.5 . . ?
C7N C8N H8NB 110.5 . . ?
H8NA C8N H8NB 108.7 . . ?
C9N C8N C7N 106.22(19) . . ?
C9N C8N H8NA 110.5 . . ?
C9N C8N H8NB 110.5 . . ?
C5N C9N C8N 105.96(19) . . ?
C5N C9N H9NA 110.5 . . ?
C5N C9N H9NB 110.5 . . ?
C8N C9N H9NA 110.5 . . ?
C8N C9N H9NB 110.5 . . ?
H9NA C9N H9NB 108.7 . . ?

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 N1N 0.96(3) 1.78(3) 2.739(3) 174(3) 8_654 yes
N1N H1N N1 0.88 1.92 2.739(3) 154.3 6_565 yes
C1M H1MB N3 0.99 2.53 3.473(3) 159.8 10_665 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
O1N C4N C5N N1N -178.2(2) . . . . ?
O1N C4N C5N C6N 61.2(3) . . . . ?
O1N C4N C5N C9N -56.0(3) . . . . ?
N1 N2 N3 N4 0.2(2) . . . . ?
N1N C5N C6N C7N 79.6(2) . . . . ?
N1N C5N C9N C8N -85.4(2) . . . . ?
N2 N1 C5 N4 0.1(3) . . . . ?
N2 N1 C5 C2P 174.4(2) . . . . ?
N2 N3 N4 C5 -0.2(3) . . . . ?
N3 N4 C5 N1 0.1(2) . . . . ?
N3 N4 C5 C2P -174.4(2) . . . . ?
N3N C1M C4B C3B -85.1(3) . . . . ?
N3N C1M C4B C5B 98.1(3) . . . . ?
N3N C4N C5N N1N 2.3(2) . . . . ?
N3N C4N C5N C6N -118.3(2) . . . . ?
N3N C4N C5N C9N 124.5(2) . . . . ?
C1 C2T1 C3T1 C4T1 -173.5(3) . . . . ?
C1 C2T2 C3T2 C4T2 179(3) . . . . ?
C1B C1P C2P C3P -176.5(2) . . . . ?
C1B C1P C2P C5 6.1(4) . . . . ?
C1B C1P C6P C5P 177.9(2) . . . . ?
C1B C2B C3B C4B -0.4(4) . . . . ?
C1M N3N C2N N1N 177.3(2) . . . . ?
C1M N3N C2N C1 -6.4(4) . . . . ?
C1M N3N C4N O1N 1.4(4) . . . . ?
C1M N3N C4N C5N -179.07(19) . . . . ?
C1M C4B C5B C6B 176.8(2) . . . . ?
C1P C1B C2B C3B -179.4(2) . . . . ?
C1P C1B C6B C5B -179.5(2) . . . . ?
C1P C2P C3P C4P -2.0(4) . . . . ?
C1P C2P C5 N1 51.1(4) . . . . ?
C1P C2P C5 N4 -135.4(3) . . . . ?
C2B C1B C1P C2P -140.9(2) . . . . ?
C2B C1B C1P C6P 40.0(3) . . . . ?
C2B C1B C6B C5B 2.7(3) . . . . ?
C2B C3B C4B C1M -175.7(2) . . . . ?
C2B C3B C4B C5B 1.2(3) . . . . ?
C2N N1N C5N C4N -2.4(2) . . . . ?
C2N N1N C5N C6N 120.1(2) . . . . ?
C2N N1N C5N C9N -126.0(2) . . . . ?
C2N N3N C1M C4B -85.3(3) . . . . ?
C2N N3N C4N O1N 179.0(2) . . . . ?
C2N N3N C4N C5N -1.5(2) . . . . ?
C2N C1 C2T1 C3T1 -172.7(2) . . . . ?
C2N C1 C2T2 C3T2 179(2) . . . . ?
C2P C1P C6P C5P -1.3(4) . . . . ?
C2P C3P C4P C5P -0.1(4) . . . . ?
C2T1 C1 C2N N1N 92.3(3) . . . . ?
C2T1 C1 C2N N3N -83.6(3) . . . . ?
C2T2 C1 C2N N1N 36.5(19) . . . . ?
C2T2 C1 C2N N3N -139.4(19) . . . . ?
C3B C4B C5B C6B 0.0(3) . . . . ?
C3P C2P C5 N1 -126.4(3) . . . . ?
C3P C2P C5 N4 47.2(3) . . . . ?
C3P C4P C5P C6P 1.5(4) . . . . ?
C4B C5B C6B C1B -2.0(3) . . . . ?
C4N N3N C1M C4B 91.7(3) . . . . ?
C4N N3N C2N N1N -0.1(3) . . . . ?
C4N N3N C2N C1 176.2(2) . . . . ?
C4N C5N C6N C7N -163.6(2) . . . . ?
C4N C5N C9N C8N 156.8(2) . . . . ?
C4P C5P C6P C1P -0.8(4) . . . . ?
C5 N1 N2 N3 -0.2(2) . . . . ?
C5 C2P C3P C4P 175.6(2) . . . . ?
C5N N1N C2N N3N 1.6(3) . . . . ?
C5N N1N C2N C1 -174.6(2) . . . . ?
C5N C6N C7N C8N 31.5(2) . . . . ?
C6B C1B C1P C2P 41.3(3) . . . . ?
C6B C1B C1P C6P -137.8(2) . . . . ?
C6B C1B C2B C3B -1.5(3) . . . . ?
C6N C5N C9N C8N 33.4(3) . . . . ?
C6N C7N C8N C9N -10.7(3) . . . . ?
C6P C1P C2P C3P 2.6(4) . . . . ?
C6P C1P C2P C5 -174.7(2) . . . . ?
C7N C8N C9N C5N -14.2(3) . . . . ?
C9N C5N C6N C7N -40.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
