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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1RR_AcNA_19srv317
_database_code_depnum_ccdc_archive 'CCDC 2222820'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_audit_creation_date             2019-10-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N6 O4, 2(C2 H3 N)'
_chemical_formula_sum            'C25 H32 N8 O4'
_chemical_formula_weight         508.58
_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 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0108 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   38.366(10)
_cell_length_b                   4.5756(11)
_cell_length_c                   15.248(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.235(7)
_cell_angle_gamma                90
_cell_volume                     2642.1(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7266
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.60
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;   
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1411 before and 0.1018 after correction. 
The Ratio of minimum to maximum transmission is 0.7337. 
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.006
_exptl_crystal_size_min          0.003
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21296
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         2.085
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Dectris Pilatus 2M'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'φ and ω rotation with 0.1 degree frames'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2855
_reflns_number_total             3862
_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 V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      1.073
_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)+(0.1230P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1924
_refine_ls_wR_factor_ref         0.2036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1 \\sim N2-H2 \\sim N3-H3
 with sigma of 0.005
3. Others
 Fixed Sof: H3A(0.5) H3B(0.5)
4.a Ternary CH refined with riding coordinates:
 C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
4.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C2S(H2SA,H2SB,H2SC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11208(3) 0.7839(2) 0.39265(7) 0.0280(3) Uani 1 1 d . . . . .
O2 O 0.02192(3) 0.2639(2) 0.35933(8) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.13755(3) 0.3551(2) 0.44456(8) 0.0233(3) Uani 1 1 d D . . . .
N2 N 0.09012(3) 0.3522(3) 0.33262(9) 0.0276(3) Uani 1 1 d D . . . .
N3 N 0.06084(3) 0.4942(3) 0.28630(9) 0.0242(3) Uani 1 1 d D . . . .
C1 C 0.11323(3) 0.5142(3) 0.39142(9) 0.0208(3) Uani 1 1 d . . . . .
C2 C 0.02834(3) 0.4416(3) 0.30379(9) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.000000 0.6274(4) 0.250000 0.0229(4) Uani 1 2 d S T P . .
H3A H -0.010900 0.754613 0.290591 0.027 Uiso 0.5 1 calc R . . . .
H3B H 0.010900 0.754613 0.209409 0.027 Uiso 0.5 1 calc R . . . .
C4 C 0.16733(4) 0.4934(3) 0.50195(9) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.158616 0.680401 0.524617 0.025 Uiso 1 1 calc R . . . .
C5 C 0.19650(4) 0.5691(4) 0.44897(10) 0.0284(3) Uani 1 1 d . . . . .
H5A H 0.205116 0.389876 0.424517 0.043 Uiso 1 1 calc GR . . . .
H5B H 0.215972 0.664666 0.487969 0.043 Uiso 1 1 calc GR . . . .
H5C H 0.187196 0.701523 0.400285 0.043 Uiso 1 1 calc GR . . . .
C6 C 0.17842(4) 0.2943(3) 0.58137(9) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.21212(4) 0.1786(3) 0.60194(10) 0.0255(3) Uani 1 1 d . . . . .
H7 H 0.229466 0.226995 0.566362 0.031 Uiso 1 1 calc R . . . .
C8 C 0.22076(4) -0.0076(4) 0.67419(11) 0.0325(4) Uani 1 1 d . . . . .
H8 H 0.243969 -0.085247 0.687782 0.039 Uiso 1 1 calc R . . . .
C9 C 0.19595(5) -0.0796(4) 0.72584(11) 0.0367(4) Uani 1 1 d . . . . .
H9 H 0.201833 -0.209308 0.774627 0.044 Uiso 1 1 calc R . . . .
C10 C 0.16218(5) 0.0372(4) 0.70677(12) 0.0380(4) Uani 1 1 d . . . . .
H10 H 0.144974 -0.010873 0.742814 0.046 Uiso 1 1 calc R . . . .
C11 C 0.15365(4) 0.2237(4) 0.63516(11) 0.0298(4) Uani 1 1 d . . . . .
H11 H 0.130583 0.304560 0.622609 0.036 Uiso 1 1 calc R . . . .
H1 H 0.1368(5) 0.165(3) 0.4371(13) 0.039(5) Uiso 1 1 d D . . . .
H2 H 0.0886(5) 0.162(3) 0.3385(14) 0.044(6) Uiso 1 1 d D . . . .
H3 H 0.0650(5) 0.609(4) 0.2429(10) 0.030(5) Uiso 1 1 d D . . . .
N1S N 0.06730(4) -0.0952(4) 0.14127(12) 0.0472(4) Uani 1 1 d . . . . .
C1S C 0.05692(4) 0.0581(4) 0.08467(11) 0.0308(4) Uani 1 1 d . . . . .
C2S C 0.04318(5) 0.2493(4) 0.01175(12) 0.0387(4) Uani 1 1 d . . . . .
H2SA H 0.041073 0.140927 -0.044296 0.058 Uiso 1 1 calc GR . . . .
H2SB H 0.059277 0.414792 0.010145 0.058 Uiso 1 1 calc GR . . . .
H2SC H 0.019884 0.321652 0.019983 0.058 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2351(16) . ?
O2 C2 1.2268(19) . ?
N1 C1 1.3469(16) . ?
N1 C4 1.4664(16) . ?
N1 H1 0.877(13) . ?
N2 N3 1.3887(15) . ?
N2 C1 1.3728(17) . ?
N2 H2 0.878(13) . ?
N3 C2 1.338(2) . ?
N3 H3 0.880(13) . ?
C2 C3 1.5138(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4 1.0000 . ?
C4 C5 1.522(2) . ?
C4 C6 1.5207(19) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.385(2) . ?
C6 C11 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(2) . ?
C11 H11 0.9500 . ?
N1S C1S 1.133(2) . ?
C1S C2S 1.446(2) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 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
C1 N1 C4 121.59(11) . . ?
C1 N1 H1 117.0(13) . . ?
C4 N1 H1 120.7(13) . . ?
N3 N2 H2 117.0(14) . . ?
C1 N2 N3 117.69(12) . . ?
C1 N2 H2 121.0(14) . . ?
N2 N3 H3 115.8(12) . . ?
C2 N3 N2 121.21(13) . . ?
C2 N3 H3 122.9(12) . . ?
O1 C1 N1 123.63(12) . . ?
O1 C1 N2 121.90(12) . . ?
N1 C1 N2 114.43(12) . . ?
O2 C2 N3 123.61(13) . . ?
O2 C2 C3 122.66(12) . . ?
N3 C2 C3 113.71(12) . . ?
C2 C3 C2 111.67(15) 2 . ?
C2 C3 H3A 109.3 2 . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 2 . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 H4 107.7 . . ?
N1 C4 C5 110.50(12) . . ?
N1 C4 C6 107.96(10) . . ?
C5 C4 H4 107.7 . . ?
C6 C4 H4 107.7 . . ?
C6 C4 C5 115.05(12) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 122.75(14) . . ?
C7 C6 C11 118.64(14) . . ?
C11 C6 C4 118.61(13) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.60(15) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.24(15) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.89(16) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.82(17) . . ?
C11 C10 H10 120.1 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.80(15) . . ?
C10 C11 H11 119.6 . . ?
N1S C1S C2S 178.9(2) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?

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 O1 0.877(13) 2.048(15) 2.8574(16) 152.9(17) 1_545 yes
N2 H2 O1 0.878(13) 2.061(15) 2.8392(16) 147.3(19) 1_545 yes
N3 H3 N1S 0.880(13) 2.069(14) 2.943(2) 171.6(17) 1_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 N2 N3 169.36(13) . . . . ?
N2 N3 C2 O2 -1.6(2) . . . . ?
N3 N2 C1 O1 -12.7(2) . . . . ?
C1 N2 N3 C2 -109.36(16) . . . . ?
C2 N3 N2 C1 -109.36(16) . . . . ?
C2 C3 C2 O2 -58.94(12) 2 . . . ?
C2 C3 C2 N3 122.39(13) 2 . . . ?
C3 C2 N3 N2 177.08(12) . . . . ?
C4 N1 C1 O1 -7.0(2) . . . . ?
C4 N1 C1 N2 170.92(13) . . . . ?
C5 C4 N1 C1 -80.74(17) . . . . ?
C5 C4 C6 C7 -2.85(19) . . . . ?
C5 C4 C6 C11 177.61(13) . . . . ?
C6 C4 N1 C1 152.65(13) . . . . ?
C7 C6 C4 N1 121.06(15) . . . . ?
C7 C6 C4 C5 -2.85(19) . . . . ?
C11 C6 C4 N1 -58.48(17) . . . . ?


_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_1RR_EtOH_d
_database_code_depnum_ccdc_archive 'CCDC 2222824'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_audit_creation_date             2022-11-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N6 O4, 0.5(C2 H6 O)'
_chemical_formula_sum            'C22 H29 N6 O4.50'
_chemical_formula_weight         449.51
_chemical_absolute_configuration unk
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.278(2)
_cell_length_b                   4.5289(10)
_cell_length_c                   22.111(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.188(5)
_cell_angle_gamma                90
_cell_volume                     1129.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    971
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      17.83
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1464 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.7040.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             478
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2458
_diffrn_reflns_av_unetI/netI     0.2980
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19132
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.607
_diffrn_ambient_temperature      120.00
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1756
_reflns_number_total             4432
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.40A (Bruker AXS, 2019)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT v8.40A (Bruker AXS, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.2428
_refine_ls_R_factor_gt           0.0792
_refine_ls_restrained_S_all      0.935
_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)+(0.0499P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1785
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(N5) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: O5(0.5) H5A(0.5) C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5)
 H23B(0.5) H23C(0.5)
4.a Ternary CH refined with riding coordinates:
 C6(H6A), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C23(H23A,H23B,H23C)
4.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2727(5) 1.1919(12) 0.6734(2) 0.0373(16) Uani 1 1 d . . . . .
O2 O 0.2964(6) 0.7667(15) 0.5429(3) 0.0514(18) Uani 1 1 d . . . . .
O3 O 0.0599(6) 0.8099(15) 0.4212(2) 0.0507(18) Uani 1 1 d . . . . .
O4 O 0.1718(5) 1.1868(12) 0.3005(2) 0.0394(16) Uani 1 1 d . . . . .
N1 N 0.3136(6) 0.7577(17) 0.7209(3) 0.0336(18) Uani 1 1 d . . . . .
H1 H 0.291547 0.573161 0.726035 0.040 Uiso 1 1 calc R U . . .
N2 N 0.1725(5) 0.7743(16) 0.6452(3) 0.0325(18) Uani 1 1 d . . . . .
H2 H 0.143255 0.602488 0.655969 0.039 Uiso 1 1 calc R U . . .
N3 N 0.1369(6) 0.9155(14) 0.5923(3) 0.0354(18) Uani 1 1 d . . . . .
H3 H 0.067881 1.006095 0.590260 0.043 Uiso 1 1 calc R U . . .
N4 N 0.2479(6) 0.9134(15) 0.4016(3) 0.039(2) Uani 1 1 d . . . . .
H4 H 0.315419 0.992624 0.413849 0.047 Uiso 1 1 calc R U . . .
N5 N 0.2415(6) 0.7678(17) 0.3458(3) 0.0360(19) Uani 1 1 d . U . . .
H5 H 0.272280 0.591425 0.340459 0.043 Uiso 1 1 calc R U . . .
N6 N 0.1488(5) 0.7453(15) 0.2533(3) 0.0331(18) Uani 1 1 d . . . . .
H6 H 0.166974 0.556421 0.254342 0.040 Uiso 1 1 calc R U . . .
C1 C 0.2564(7) 0.920(2) 0.6795(4) 0.029(2) Uani 1 1 d . . . . .
C2 C 0.2072(9) 0.914(2) 0.5446(4) 0.042(3) Uani 1 1 d . . . . .
C3 C 0.1677(9) 1.1064(19) 0.4923(3) 0.039(3) Uani 1 1 d . . . . .
H3A H 0.091165 1.201015 0.501919 0.047 Uiso 1 1 calc R U . . .
H3B H 0.226865 1.264550 0.486341 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1537(9) 0.9338(19) 0.4362(4) 0.035(2) Uani 1 1 d . . . . .
C5 C 0.1843(7) 0.918(2) 0.3002(4) 0.034(2) Uani 1 1 d . . . . .
C6 C 0.0818(7) 0.8578(19) 0.2014(3) 0.031(2) Uani 1 1 d . . . . .
H6A H 0.114468 1.056588 0.191230 0.037 Uiso 1 1 calc R U . . .
C7 C -0.0481(7) 0.898(2) 0.2179(4) 0.048(3) Uani 1 1 d . . . . .
H7A H -0.082781 0.705410 0.227238 0.072 Uiso 1 1 calc R U . . .
H7B H -0.091684 0.987039 0.183667 0.072 Uiso 1 1 calc R U . . .
H7C H -0.053110 1.027411 0.253233 0.072 Uiso 1 1 calc R U . . .
C8 C 0.1013(8) 0.6581(17) 0.1481(3) 0.025(2) Uani 1 1 d . . . . .
C9 C 0.0116(8) 0.5550(19) 0.1104(3) 0.032(2) Uani 1 1 d . . . . .
H9 H -0.067990 0.610911 0.117892 0.039 Uiso 1 1 calc R U . . .
C10 C 0.0345(8) 0.373(2) 0.0621(4) 0.038(2) Uani 1 1 d . . . . .
H10 H -0.029288 0.304585 0.037137 0.045 Uiso 1 1 calc R U . . .
C11 C 0.1479(8) 0.290(2) 0.0498(4) 0.039(2) Uani 1 1 d . . . . .
H11 H 0.163840 0.163626 0.016693 0.047 Uiso 1 1 calc R U . . .
C12 C 0.2389(7) 0.395(2) 0.0868(4) 0.038(2) Uani 1 1 d . . . . .
H12 H 0.318681 0.344346 0.078505 0.045 Uiso 1 1 calc R U . . .
C13 C 0.2149(8) 0.569(2) 0.1348(4) 0.038(2) Uani 1 1 d . . . . .
H13 H 0.278694 0.633080 0.160240 0.045 Uiso 1 1 calc R U . . .
C14 C 0.4118(7) 0.8738(19) 0.7583(4) 0.036(2) Uani 1 1 d . . . . .
H14 H 0.397560 1.089997 0.763835 0.043 Uiso 1 1 calc R U . . .
C15 C 0.5279(8) 0.840(2) 0.7250(4) 0.053(3) Uani 1 1 d . . . . .
H15A H 0.543479 0.630236 0.717880 0.080 Uiso 1 1 calc R U . . .
H15B H 0.592836 0.924862 0.749437 0.080 Uiso 1 1 calc R U . . .
H15C H 0.521968 0.943705 0.686099 0.080 Uiso 1 1 calc R U . . .
C16 C 0.4099(7) 0.7334(19) 0.8199(3) 0.027(2) Uani 1 1 d . . . . .
C17 C 0.3172(8) 0.781(3) 0.8576(4) 0.052(3) Uani 1 1 d . . . . .
H17 H 0.253829 0.902802 0.843648 0.062 Uiso 1 1 calc R U . . .
C18 C 0.3108(9) 0.661(2) 0.9144(4) 0.058(3) Uani 1 1 d . . . . .
H18 H 0.244273 0.702489 0.938677 0.070 Uiso 1 1 calc R U . . .
C19 C 0.3993(8) 0.484(2) 0.9361(4) 0.046(3) Uani 1 1 d . . . . .
H19 H 0.395761 0.401757 0.975510 0.055 Uiso 1 1 calc R U . . .
C20 C 0.4927(8) 0.428(2) 0.9002(4) 0.047(3) Uani 1 1 d . . . . .
H20 H 0.554920 0.302773 0.914502 0.057 Uiso 1 1 calc R U . . .
C21 C 0.4983(8) 0.551(2) 0.8423(4) 0.041(2) Uani 1 1 d . . . . .
H21 H 0.564547 0.508808 0.817921 0.050 Uiso 1 1 calc R U . . .
O5 O 0.5682(11) 0.820(3) 0.5592(5) 0.056(4) Uani 0.5 1 d . U P . .
H5A H 0.625062 0.859032 0.536623 0.084 Uiso 0.5 1 calc R U P . .
C22 C 0.5192(15) 0.536(5) 0.5429(8) 0.047(5) Uani 0.5 1 d . . P . .
H22A H 0.583581 0.437077 0.520754 0.056 Uiso 0.5 1 calc R U P . .
H22B H 0.457366 0.582120 0.511878 0.056 Uiso 0.5 1 calc R U P . .
C23 C 0.4669(14) 0.299(5) 0.5788(7) 0.050(5) Uani 0.5 1 d . U P . .
H23A H 0.468778 0.354611 0.621579 0.074 Uiso 0.5 1 calc R U P . .
H23B H 0.512387 0.116562 0.573394 0.074 Uiso 0.5 1 calc R U P . .
H23C H 0.384580 0.266642 0.565281 0.074 Uiso 0.5 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.253(10) . ?
O2 C2 1.209(9) . ?
O3 C4 1.236(9) . ?
O4 C5 1.224(10) . ?
N1 C1 1.330(10) . ?
N1 C14 1.466(9) . ?
N2 N3 1.384(8) . ?
N2 C1 1.371(9) . ?
N3 C2 1.333(11) . ?
N4 N5 1.398(8) . ?
N4 C4 1.325(9) . ?
N5 C5 1.368(10) . ?
N6 C5 1.354(10) . ?
N6 C6 1.454(9) . ?
C2 C3 1.507(12) . ?
C3 C4 1.473(10) . ?
C6 C7 1.528(10) . ?
C6 C8 1.505(10) . ?
C8 C9 1.379(10) . ?
C8 C13 1.380(11) . ?
C9 C10 1.377(10) . ?
C10 C11 1.366(10) . ?
C11 C12 1.383(10) . ?
C12 C13 1.354(11) . ?
C14 C15 1.524(11) . ?
C14 C16 1.504(10) . ?
C16 C17 1.366(11) . ?
C16 C21 1.378(10) . ?
C17 C18 1.370(12) . ?
C18 C19 1.361(12) . ?
C19 C20 1.356(11) . ?
C20 C21 1.400(11) . ?
O5 C22 1.44(2) . ?
C22 C23 1.47(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C14 122.7(7) . . ?
C1 N2 N3 115.5(7) . . ?
C2 N3 N2 119.9(7) . . ?
C4 N4 N5 121.0(7) . . ?
C5 N5 N4 115.4(7) . . ?
C5 N6 C6 122.9(7) . . ?
O1 C1 N1 123.2(8) . . ?
O1 C1 N2 121.0(8) . . ?
N1 C1 N2 115.7(8) . . ?
O2 C2 N3 122.5(9) . . ?
O2 C2 C3 121.9(9) . . ?
N3 C2 C3 115.6(9) . . ?
C4 C3 C2 111.4(7) . . ?
O3 C4 N4 120.4(8) . . ?
O3 C4 C3 122.8(9) . . ?
N4 C4 C3 116.8(8) . . ?
O4 C5 N5 123.0(8) . . ?
O4 C5 N6 123.1(9) . . ?
N6 C5 N5 113.8(8) . . ?
N6 C6 C7 109.8(7) . . ?
N6 C6 C8 109.1(7) . . ?
C8 C6 C7 114.5(7) . . ?
C9 C8 C6 124.0(8) . . ?
C9 C8 C13 116.4(8) . . ?
C13 C8 C6 119.5(8) . . ?
C10 C9 C8 121.6(8) . . ?
C11 C10 C9 120.7(8) . . ?
C10 C11 C12 118.3(8) . . ?
C13 C12 C11 120.3(8) . . ?
C12 C13 C8 122.6(8) . . ?
N1 C14 C15 109.7(7) . . ?
N1 C14 C16 109.6(7) . . ?
C16 C14 C15 115.2(7) . . ?
C17 C16 C14 120.7(8) . . ?
C17 C16 C21 115.6(8) . . ?
C21 C16 C14 123.7(8) . . ?
C16 C17 C18 123.5(9) . . ?
C19 C18 C17 120.2(9) . . ?
C20 C19 C18 118.6(9) . . ?
C19 C20 C21 120.6(9) . . ?
C16 C21 C20 121.4(8) . . ?
O5 C22 C23 132.3(16) . . ?

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 O1 0.88 2.09 2.804(9) 137.6 1_545 yes
N2 H2 O1 0.88 2.39 2.931(9) 120.0 1_545 yes
N3 H3 O3 0.88 2.01 2.860(10) 163.6 2_556 yes
N4 H4 O5 0.88 2.06 2.892(15) 157.7 2_656 yes
N5 H5 O4 0.88 2.32 2.918(9) 125.3 1_545 yes
N6 H6 O4 0.88 1.96 2.747(9) 147.9 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 N2 N3 -163.0(7) . . . . ?
N2 N3 C2 O2 8.2(13) . . . . ?
N3 N2 C1 O1 20.3(11) . . . . ?
N4 N5 C5 O4 22.0(12) . . . . ?
N5 N4 C4 O3 4.0(12) . . . . ?
N6 C5 N5 N4 -161.5(7) . . . . ?
C1 N2 N3 C2 76.0(9) . . . . ?
C2 C3 C4 O3 88.7(10) . . . . ?
C2 C3 C4 N4 -90.7(10) . . . . ?
C3 C2 N3 N2 -172.4(7) . . . . ?
C3 C4 N4 N5 -176.5(7) . . . . ?
C4 N4 N5 C5 74.9(10) . . . . ?
C4 C3 C2 O2 56.4(12) . . . . ?
C4 C3 C2 N3 -123.0(9) . . . . ?
C6 N6 C5 O4 -6.3(13) . . . . ?
C6 N6 C5 N5 177.2(6) . . . . ?
C7 C6 N6 C5 -77.9(9) . . . . ?
C7 C6 C8 C9 10.1(11) . . . . ?
C7 C6 C8 C13 -170.1(8) . . . . ?
C8 C6 N6 C5 155.9(7) . . . . ?
C9 C8 C6 N6 133.5(7) . . . . ?
C13 C8 C6 N6 -46.7(10) . . . . ?
C14 N1 C1 O1 -7.9(12) . . . . ?
C14 N1 C1 N2 175.5(7) . . . . ?
C15 C14 N1 C1 -86.3(9) . . . . ?
C15 C14 C16 C17 171.4(8) . . . . ?
C15 C14 C16 C21 -8.9(12) . . . . ?
C16 C14 N1 C1 146.4(7) . . . . ?
C17 C16 C14 N1 -64.4(11) . . . . ?
C21 C16 C14 N1 115.3(9) . . . . ?


# start Validation Reply Form
_vrf_RINTA01_1RR_EtOH_d          
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The diffraction from these thin needles was very weak, more 
than 90% of reflections above 0.95 Ang were unobserved (i.e. less than 
2 sigma (I)). 
Nevertheless the structure was succesfully solved and refined but some formal 
refinement criteria and precision of geometrical parameters were affected by 
such weak diffraction.
;
_vrf_PLAT020_1RR_EtOH_d          
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.246 Report
RESPONSE: The diffraction from these thin needles was very weak, more 
than 90% of reflections above 0.95 Ang were unobserved (i.e. less than 
2 sigma (I)). 
Nevertheless the structure was succesfully solved and refined but some formal 
refinement criteria and precision of geometrical parameters were affected by 
such weak diffraction.
;
_vrf_PLAT340_1RR_EtOH_d          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01206 Ang.  
RESPONSE: The diffraction from these thin needles was very weak, more 
than 90% of reflections above 0.95 Ang were unobserved (i.e. less than 
2 sigma (I)). 
Nevertheless the structure was succesfully solved and refined but some formal 
refinement criteria and precision of geometrical parameters were affected by 
such weak diffraction.
;
_vrf_PLAT420_1RR_EtOH_d          
;
PROBLEM: D-H Bond Without Acceptor  O5       --H5A      .     Please Check 
RESPONSE: The H atom belongs to OH group of half-occupied solvent ethanol
molecule and  could not be located in residual Fourier maps. The atom was 
placed in calculated position using AFIX 147. The solvent molecule is sitting 
in a void in the structure and participates in N4H...O5 hydrogen bond as an 
acceptor. 
There are no other recognisable classical acceptors of hydrogen bonds in close 
proximity of this OH group. The poor quality of the experimantal data does not 
allow to speculate on the geometry of hydrogen bonds in the crystal of studied 
compound. However, the uncertainty in the exact position of the H atom in 
solvent molecule does not affect the confomation of main molecule, determination 
of which was the principal aim of the study.    
;
# end Validation Reply Form

_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_1RR_AcNB_mix
_database_code_depnum_ccdc_archive 'CCDC 2222821'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_audit_creation_date             2022-11-21
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3


loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N6 O4, 2(C2 H3 N)'
_chemical_formula_sum            'C25 H32 N8 O4'
_chemical_formula_weight         508.58
_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 0.0019 0.0015 '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 0.0037 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0071 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.482(4)
_cell_length_b                   9.1899(15)
_cell_length_c                   17.264(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.867(4)
_cell_angle_gamma                90
_cell_volume                     2774.6(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1246
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      19.88
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.3726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1210 before and 0.0738 after correction.
The Ratio of minimum to maximum transmission is 0.5000.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.004
_exptl_crystal_size_min          0.002
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1357
_diffrn_reflns_av_unetI/netI     0.1765
_diffrn_reflns_Laue_measured_fraction_full 0.760
_diffrn_reflns_Laue_measured_fraction_max 0.760
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12165
_diffrn_reflns_point_group_measured_fraction_full 0.760
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        23.992
_diffrn_reflns_theta_max         23.992
_diffrn_reflns_theta_min         2.257
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_area_resol_mean 54.8
_diffrn_detector_type            'Dectris Pilatus 2M'
_diffrn_measured_fraction_theta_full 0.760
_diffrn_measured_fraction_theta_max 0.760
_diffrn_measurement_device       
'dual air-bearing fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'φ rotation with 0.1 degree frames'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'double crystal Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1898
_reflns_number_total             3634
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS, 2005-2017)'
_computing_data_collection       
'Diamond I19 EH1 GDA (Allan et al., 2017), DIALS (Winter et al., 2018)'
_computing_data_reduction        
'cbf_to_sfrm.py (Johnson & Probert, 2016), SAINT V8.38A (Bruker AXS, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.020(7)
_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   1.285
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.2126
_refine_ls_R_factor_gt           0.1509
_refine_ls_restrained_S_all      1.341
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3806
_refine_ls_wR_factor_ref         0.4319
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N3) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(N4) \\sim
Ueq, Uanis(N5) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(O4) \\sim Ueq: with sigma of 0.003 and sigma for terminal
atoms of 0.006
3.a Riding coordinates:
 N1(H1), N2(H2), N3(H3), N5(H5), N6(H6)
3.b Ternary CH refined with riding coordinates:
 C6(H6A), C14(H14)
3.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.d Aromatic/amide H refined with riding coordinates:
 N4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
3.e Fitted hexagon refined as free rotating group:
 C8(C9,C10,C11,C12,C13), C16(C17,C18,C19,C20,C21)
3.f Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C2S(H2SA,H2SB,H2SC), C4S(H4SA,H4SB,H4SC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8359(4) -0.0623(6) 0.7744(3) 0.0716(18) Uani 1 1 d . . . . .
O2 O 0.9793(4) 0.0811(6) 0.9217(3) 0.0666(18) Uani 1 1 d . . . . .
O3 O 1.1532(4) 0.1951(6) 0.9593(3) 0.0718(18) Uani 1 1 d . . . . .
O4 O 1.0157(3) 0.5863(6) 0.8200(3) 0.0644(16) Uani 1 1 d . U . . .
N1 N 0.7864(5) -0.0617(8) 0.8795(4) 0.074(2) Uani 1 1 d . . . . .
H1 H 0.797119 -0.078539 0.939907 0.089 Uiso 1 1 d R U . . .
N2 N 0.9028(4) -0.1705(8) 0.8965(4) 0.0668(19) Uani 1 1 d . U . . .
H2 H 0.897276 -0.234400 0.941776 0.080 Uiso 1 1 d R U . . .
N3 N 0.9735(4) -0.1547(9) 0.8844(3) 0.0649(19) Uani 1 1 d . U . . .
H3 H 0.997639 -0.239820 0.865079 0.078 Uiso 1 1 d R U . . .
N4 N 1.0747(3) 0.2210(8) 0.8274(3) 0.0594(18) Uani 1 1 d . U . . .
H4 H 1.047858 0.175949 0.782251 0.071 Uiso 1 1 calc R U . . .
N5 N 1.0788(4) 0.3731(8) 0.8280(3) 0.0618(18) Uani 1 1 d . U . . .
H5 H 1.123896 0.423066 0.818645 0.074 Uiso 1 1 d R U . . .
N6 N 0.9779(4) 0.3856(7) 0.8792(3) 0.066(2) Uani 1 1 d . . . . .
H6 H 0.995320 0.290549 0.908534 0.079 Uiso 1 1 d R U . . .
C1 C 0.8415(5) -0.0977(11) 0.8459(5) 0.068(2) Uani 1 1 d . U . . .
C2 C 1.0092(5) -0.0245(10) 0.8991(4) 0.066(2) Uani 1 1 d . . . . .
C3 C 1.0860(5) -0.0157(11) 0.8876(4) 0.063(2) Uani 1 1 d . U . . .
H3A H 1.082988 -0.054593 0.833206 0.076 Uiso 1 1 calc R U . . .
H3B H 1.123565 -0.074488 0.929994 0.076 Uiso 1 1 calc R U . . .
C4 C 1.1110(5) 0.1422(10) 0.8945(5) 0.062(2) Uani 1 1 d . U . . .
C5 C 1.0222(5) 0.4540(11) 0.8411(4) 0.059(2) Uani 1 1 d . U . . .
C6 C 0.7139(6) 0.0000(11) 0.8328(6) 0.084(3) Uani 1 1 d . . . . .
H6A H 0.722364 0.060643 0.788376 0.100 Uiso 1 1 calc R U . . .
C7 C 0.6859(8) 0.1003(13) 0.8868(7) 0.109(4) Uani 1 1 d . . . . .
H7A H 0.634680 0.136204 0.856081 0.163 Uiso 1 1 calc R U . . .
H7B H 0.720992 0.182828 0.904172 0.163 Uiso 1 1 calc R U . . .
H7C H 0.683768 0.046746 0.935144 0.163 Uiso 1 1 calc R U . . .
C8 C 0.6529(4) -0.1214(9) 0.7903(4) 0.090(3) Uani 1 1 d G . . . .
C9 C 0.6544(4) -0.2546(10) 0.8290(4) 0.100(3) Uani 1 1 d G . . . .
H9 H 0.692787 -0.273753 0.879877 0.120 Uiso 1 1 calc R U . . .
C10 C 0.5998(6) -0.3598(8) 0.7932(6) 0.118(4) Uani 1 1 d G . . . .
H10 H 0.600815 -0.450812 0.819620 0.141 Uiso 1 1 calc R U . . .
C11 C 0.5436(5) -0.3318(12) 0.7188(6) 0.132(5) Uani 1 1 d G . . . .
H11 H 0.506303 -0.403656 0.694299 0.159 Uiso 1 1 calc R U . . .
C12 C 0.5421(4) -0.1986(14) 0.6801(4) 0.128(5) Uani 1 1 d G . . . .
H12 H 0.503763 -0.179441 0.629232 0.154 Uiso 1 1 calc R U . . .
C13 C 0.5968(5) -0.0934(10) 0.7159(4) 0.124(5) Uani 1 1 d G . . . .
H13 H 0.595734 -0.002380 0.689488 0.149 Uiso 1 1 calc R U . . .
C14 C 0.9045(6) 0.4494(10) 0.8778(4) 0.072(3) Uani 1 1 d . . . . .
H14 H 0.911125 0.556583 0.887418 0.086 Uiso 1 1 calc R U . . .
C15 C 0.8813(6) 0.3807(10) 0.9468(5) 0.077(3) Uani 1 1 d . . . . .
H15A H 0.830321 0.415342 0.943817 0.115 Uiso 1 1 calc R U . . .
H15B H 0.918235 0.408151 0.999678 0.115 Uiso 1 1 calc R U . . .
H15C H 0.880412 0.274563 0.941108 0.115 Uiso 1 1 calc R U . . .
C16 C 0.8429(3) 0.4221(6) 0.7941(3) 0.069(3) Uani 1 1 d G . . . .
C17 C 0.8385(3) 0.2880(6) 0.7556(3) 0.076(3) Uani 1 1 d G . . . .
H17 H 0.872881 0.212282 0.781235 0.091 Uiso 1 1 calc R U . . .
C18 C 0.7836(4) 0.2647(6) 0.6797(3) 0.085(3) Uani 1 1 d G . . . .
H18 H 0.780596 0.173016 0.653394 0.102 Uiso 1 1 calc R U . . .
C19 C 0.7333(3) 0.3755(8) 0.6422(3) 0.085(3) Uani 1 1 d G . . . .
H19 H 0.695802 0.359534 0.590347 0.102 Uiso 1 1 calc R U . . .
C20 C 0.7377(3) 0.5096(7) 0.6807(4) 0.088(3) Uani 1 1 d G . . . .
H20 H 0.703291 0.585317 0.655141 0.105 Uiso 1 1 calc R U . . .
C21 C 0.7925(4) 0.5329(5) 0.7567(4) 0.078(3) Uani 1 1 d G . . . .
H21 H 0.795575 0.624586 0.782983 0.093 Uiso 1 1 calc R U . . .
N1S N 0.3791(11) -0.0899(19) 0.5066(8) 0.173(6) Uani 1 1 d . . . . .
C1S C 0.3396(9) 0.0039(17) 0.4711(7) 0.112(4) Uani 1 1 d . . . . .
C2S C 0.2869(8) 0.1165(14) 0.4246(7) 0.111(4) Uani 1 1 d . . . . .
H2SA H 0.272182 0.094580 0.365993 0.166 Uiso 1 1 calc R U . . .
H2SB H 0.312304 0.211519 0.435256 0.166 Uiso 1 1 calc R U . . .
H2SC H 0.241205 0.118544 0.441558 0.166 Uiso 1 1 calc R U . . .
N2S N 0.4095(8) 0.4025(14) 0.4944(7) 0.121(4) Uani 1 1 d . . . . .
C3S C 0.4628(9) 0.3595(13) 0.5426(8) 0.095(3) Uani 1 1 d . . . . .
C4S C 0.5295(8) 0.3070(19) 0.6048(8) 0.136(5) Uani 1 1 d . . . . .
H4SA H 0.555161 0.234299 0.581213 0.204 Uiso 1 1 calc R U . . .
H4SB H 0.514650 0.262472 0.648945 0.204 Uiso 1 1 calc R U . . .
H4SC H 0.564490 0.388267 0.626707 0.204 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
O1 C1 1.249(9) . ?
O2 C2 1.242(10) . ?
O3 C4 1.238(9) . ?
O4 C5 1.264(10) . ?
N1 C1 1.366(10) . ?
N1 C6 1.438(12) . ?
N2 N3 1.396(9) . ?
N2 C1 1.361(11) . ?
N3 C2 1.351(11) . ?
N4 N5 1.400(9) . ?
N4 C4 1.346(10) . ?
N5 C5 1.361(10) . ?
N6 C5 1.359(10) . ?
N6 C14 1.469(11) . ?
C2 C3 1.496(12) . ?
C3 C4 1.516(13) . ?
C6 C7 1.518(13) . ?
C6 C8 1.587(13) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C14 C15 1.526(11) . ?
C14 C16 1.544(10) . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C20 C21 1.3900 . ?
N1S C1S 1.168(18) . ?
C1S C2S 1.47(2) . ?
N2S C3S 1.134(15) . ?
C3S C4S 1.433(19) . ?

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
C1 N1 C6 123.1(6) . . ?
C1 N2 N3 118.6(7) . . ?
C2 N3 N2 119.2(7) . . ?
C4 N4 N5 121.3(7) . . ?
C5 N5 N4 120.2(7) . . ?
C5 N6 C14 120.3(7) . . ?
O1 C1 N1 121.4(8) . . ?
O1 C1 N2 123.3(7) . . ?
N2 C1 N1 115.3(7) . . ?
O2 C2 N3 120.7(8) . . ?
O2 C2 C3 122.6(8) . . ?
N3 C2 C3 116.7(8) . . ?
C2 C3 C4 108.6(7) . . ?
O3 C4 N4 124.0(9) . . ?
O3 C4 C3 122.3(7) . . ?
N4 C4 C3 113.2(7) . . ?
O4 C5 N5 118.9(7) . . ?
O4 C5 N6 124.7(7) . . ?
N6 C5 N5 116.4(8) . . ?
N1 C6 C7 109.7(9) . . ?
N1 C6 C8 112.1(8) . . ?
C7 C6 C8 112.2(9) . . ?
C9 C8 C6 119.8(7) . . ?
C9 C8 C13 120.0 . . ?
C13 C8 C6 120.2(7) . . ?
C8 C9 C10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C10 C11 C12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C12 C13 C8 120.0 . . ?
N6 C14 C15 108.2(7) . . ?
N6 C14 C16 110.4(5) . . ?
C15 C14 C16 110.7(8) . . ?
C17 C16 C14 120.2(5) . . ?
C17 C16 C21 120.0 . . ?
C21 C16 C14 119.8(5) . . ?
C18 C17 C16 120.0 . . ?
C19 C18 C17 120.0 . . ?
C20 C19 C18 120.0 . . ?
C19 C20 C21 120.0 . . ?
C20 C21 C16 120.0 . . ?
N1S C1S C2S 177.2(19) . . ?
N2S C3S C4S 178.7(14) . . ?

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 O3 1.01 2.00 2.914(8) 149.8 3_757 yes
N2 H2 O3 1.01 2.22 2.998(7) 132.3 3_757 yes
N3 H3 O4 1.01 1.85 2.841(9) 164.9 1_545 yes
N4 H4 O4 0.88 1.96 2.837(8) 176.5 2_746 yes
N5 H5 O1 1.01 1.98 2.786(8) 135.0 2_756 yes
N6 H6 O2 1.01 1.97 2.891(8) 150.2 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 N2 N3 -151.3(7) . . . . ?
N2 N3 C2 O2 -1.2(10) . . . . ?
N3 N2 C1 O1 26.9(13) . . . . ?
N4 N5 C5 O4 -161.0(6) . . . . ?
N5 N4 C4 O3 -3.9(11) . . . . ?
N6 C5 N5 N4 21.1(9) . . . . ?
C1 N2 N3 C2 67.5(9) . . . . ?
C2 C3 C4 O3 95.6(9) . . . . ?
C2 C3 C4 N4 -75.9(7) . . . . ?
C3 C2 N3 N2 178.1(6) . . . . ?
C3 C4 N4 N5 167.4(6) . . . . ?
C4 N4 N5 C5 -96.6(8) . . . . ?
C4 C3 C2 O2 -9.1(10) . . . . ?
C4 C3 C2 N3 171.6(6) . . . . ?
C6 N1 C1 O1 9.1(14) . . . . ?
C6 N1 C1 N2 -172.6(9) . . . . ?
C7 C6 N1 C1 -148.8(9) . . . . ?
C7 C6 C8 C9 -90.7(9) . . . . ?
C7 C6 C8 C13 87.5(8) . . . . ?
C8 C6 N1 C1 85.9(10) . . . . ?
C9 C8 C6 N1 33.2(8) . . . . ?
C13 C8 C6 N1 -148.6(5) . . . . ?
C14 N6 C5 O4 17.7(12) . . . . ?
C14 N6 C5 N5 -164.6(7) . . . . ?
C15 C14 N6 C5 -161.2(7) . . . . ?
C15 C14 C16 C17 -78.6(7) . . . . ?
C15 C14 C16 C21 102.4(7) . . . . ?
C16 C14 N6 C5 77.5(9) . . . . ?
C17 C16 C14 N6 41.3(8) . . . . ?
C21 C16 C14 N6 -137.7(6) . . . . ?

# start Validation Reply Form
_vrf_PLAT029_1RR_AcNB_mix        
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.760 Why?  
RESPONSE: Weakly diffracting tiny crystals of the studied compound 
decayed rapidly in the synchrotron beam and the final dataset was 
obtained by combining reflections from preliminary runs for only two 
available crystals. Naturally, these runs didn't cover the the whole sphere
of the data.
;
_vrf_PLAT084_1RR_AcNB_mix        
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.43 Report
RESPONSE: Weakly diffracting tiny crystals of the studied compound 
decayed rapidly in the synchrotron beam and the final dataset was 
obtained by combining reflections from preliminary runs for only two 
available crystals. The weak diffraction and decay affected the quality 
of data but nevertheless it was possible to confirm the chemical identity of the 
compound, which was the main aim of the study.
;
_vrf_PLAT340_1RR_AcNB_mix        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0124 Ang.  
RESPONSE: Weakly diffracting tiny crystals of the studied compound 
decayed rapidly in the synchrotron beam and the final dataset was 
obtained by combining reflections from preliminary runs for only two 
available crystals. The weak diffraction and decay affected the quality 
of data but nevertheless it was possible to confirm the chemical identity of the 
compound, which was the main aim of the study.
;
# end Validation Reply Form




_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_1RS_21srv164
_database_code_depnum_ccdc_archive 'CCDC 2222822'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_audit_creation_date             2021-03-24
_audit_creation_method           
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N6 O4'
_chemical_formula_sum            'C21 H26 N6 O4'
_chemical_formula_weight         426.48
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3484(8)
_cell_length_b                   9.2167(5)
_cell_length_c                   17.5718(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.049(2)
_cell_angle_gamma                90
_cell_volume                     2183.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6630
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      29.45
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1096 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.8585.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25558
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON III C7 MM CPAD'
_diffrn_detector_area_resol_mean 54.8
_diffrn_detector_type            'CPA sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω- and φ-scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3962
_reflns_number_total             5792
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS, 2016)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         5792
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.066
_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)+(0.0364P)²+1.2397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1256
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C5(H5A), C6(H6A), C7(H7), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47617(10) 0.41200(13) 0.30611(7) 0.0216(3) Uani 1 1 d . . . . .
O2 O 0.29784(10) 0.79804(14) 0.34560(8) 0.0254(3) Uani 1 1 d . . . . .
O3 O 0.52066(10) 0.91294(13) 0.43588(7) 0.0214(3) Uani 1 1 d . . . . .
O4 O 0.71038(10) 1.07312(14) 0.39452(7) 0.0242(3) Uani 1 1 d . . . . .
N1 N 0.51975(12) 0.60608(17) 0.39189(9) 0.0199(3) Uani 1 1 d . . . . .
N2 N 0.39477(12) 0.62412(16) 0.26769(9) 0.0211(3) Uani 1 1 d . . . . .
N3 N 0.40032(12) 0.77517(16) 0.27247(9) 0.0196(3) Uani 1 1 d . . . . .
N4 N 0.53067(11) 1.14805(17) 0.40322(9) 0.0194(3) Uani 1 1 d . . . . .
N5 N 0.61908(12) 1.16871(16) 0.46710(9) 0.0197(3) Uani 1 1 d . . . . .
N6 N 0.77995(13) 1.0933(2) 0.53116(10) 0.0285(4) Uani 1 1 d . . . . .
C1 C 0.61600(13) 0.5476(2) 0.44222(11) 0.0221(4) Uani 1 1 d . . . . .
H1A H 0.609547 0.439920 0.445428 0.027 Uiso 1 1 calc R U . . .
C2 C 0.69374(14) 0.5794(2) 0.40366(11) 0.0235(4) Uani 1 1 d . . . . .
C3 C 0.70341(15) 0.7178(2) 0.37525(13) 0.0276(4) Uani 1 1 d . . . . .
H3A H 0.662735 0.794627 0.381958 0.033 Uiso 1 1 calc R U . . .
C4 C 0.77181(16) 0.7442(2) 0.33737(14) 0.0351(5) Uani 1 1 d . . . . .
H4A H 0.776999 0.838620 0.317516 0.042 Uiso 1 1 calc R U . . .
C5 C 0.83260(16) 0.6345(3) 0.32814(14) 0.0373(5) Uani 1 1 d . . . . .
H5A H 0.879523 0.653307 0.302158 0.045 Uiso 1 1 calc R U . . .
C6 C 0.82473(16) 0.4972(3) 0.35694(15) 0.0385(5) Uani 1 1 d . . . . .
H6A H 0.866823 0.421434 0.351354 0.046 Uiso 1 1 calc R U . . .
C7 C 0.75508(15) 0.4700(2) 0.39412(13) 0.0319(5) Uani 1 1 d . . . . .
H7 H 0.749496 0.375125 0.413234 0.038 Uiso 1 1 calc R U . . .
C8 C 0.64292(15) 0.6095(2) 0.52755(12) 0.0294(4) Uani 1 1 d . . . . .
H8A H 0.649202 0.715238 0.525615 0.044 Uiso 1 1 calc R U . . .
H8B H 0.706084 0.568014 0.562214 0.044 Uiso 1 1 calc R U . . .
H8C H 0.590767 0.585180 0.549649 0.044 Uiso 1 1 calc R U . . .
C9 C 0.46612(13) 0.54220(19) 0.32183(10) 0.0179(4) Uani 1 1 d . . . . .
C10 C 0.35378(13) 0.85178(19) 0.31397(10) 0.0194(4) Uani 1 1 d . . . . .
C11 C 0.38518(14) 1.01041(19) 0.32467(11) 0.0212(4) Uani 1 1 d . . . . .
H11A H 0.390709 1.048983 0.273809 0.025 Uiso 1 1 calc R U . . .
H11B H 0.335472 1.068844 0.338707 0.025 Uiso 1 1 calc R U . . .
C12 C 0.48497(14) 1.01817(19) 0.39244(10) 0.0189(4) Uani 1 1 d . . . . .
C13 C 0.70440(14) 1.10689(19) 0.46036(11) 0.0202(4) Uani 1 1 d . . . . .
C14 C 0.88152(15) 1.0643(2) 0.53330(13) 0.0324(5) Uani 1 1 d . . . . .
H14 H 0.875742 1.017057 0.480643 0.039 Uiso 1 1 calc R U . . .
C15 C 0.93146(15) 0.9551(2) 0.59962(12) 0.0292(4) Uani 1 1 d . . . . .
C16 C 1.02629(16) 0.9735(3) 0.65430(13) 0.0379(5) Uani 1 1 d . . . . .
H16 H 1.061094 1.060535 0.652858 0.045 Uiso 1 1 calc R U . . .
C17 C 1.07197(19) 0.8686(3) 0.71112(14) 0.0432(6) Uani 1 1 d . . . . .
H17 H 1.137331 0.884202 0.747904 0.052 Uiso 1 1 calc R U . . .
C18 C 1.02331(19) 0.7421(3) 0.71459(15) 0.0445(6) Uani 1 1 d . . . . .
H18 H 1.054320 0.670324 0.753926 0.053 Uiso 1 1 calc R U . . .
C19 C 0.9285(2) 0.7202(3) 0.66014(17) 0.0528(7) Uani 1 1 d . . . . .
H19 H 0.894258 0.632744 0.661817 0.063 Uiso 1 1 calc R U . . .
C20 C 0.88336(18) 0.8259(3) 0.60296(16) 0.0455(6) Uani 1 1 d . . . . .
H20 H 0.818467 0.809455 0.565547 0.055 Uiso 1 1 calc R U . . .
C21 C 0.93804(18) 1.2039(3) 0.53746(16) 0.0475(6) Uani 1 1 d . . . . .
H21A H 0.903226 1.264273 0.490379 0.071 Uiso 1 1 calc R U . . .
H21B H 1.004876 1.181906 0.537495 0.071 Uiso 1 1 calc R U . . .
H21C H 0.942713 1.256119 0.587216 0.071 Uiso 1 1 calc R U . . .
H1 H 0.5116(16) 0.697(2) 0.3973(12) 0.029(6) Uiso 1 1 d . . . . .
H2 H 0.3647(15) 0.588(2) 0.2180(13) 0.028(6) Uiso 1 1 d . . . . .
H3 H 0.4359(17) 0.816(3) 0.2496(14) 0.041(7) Uiso 1 1 d . . . . .
H4 H 0.5039(15) 1.221(2) 0.3713(13) 0.026(6) Uiso 1 1 d . . . . .
H5 H 0.6140(15) 1.167(2) 0.5119(13) 0.027(6) Uiso 1 1 d . . . . .
H6 H 0.7689(17) 1.123(3) 0.5701(15) 0.037(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.251(2) . ?
O2 C10 1.227(2) . ?
O3 C12 1.232(2) . ?
O4 C13 1.229(2) . ?
N1 C1 1.464(2) . ?
N1 C9 1.343(2) . ?
N1 H1 0.86(2) . ?
N2 N3 1.395(2) . ?
N2 C9 1.362(2) . ?
N2 H2 0.89(2) . ?
N3 C10 1.345(2) . ?
N3 H3 0.84(2) . ?
N4 N5 1.389(2) . ?
N4 C12 1.347(2) . ?
N4 H4 0.87(2) . ?
N5 C13 1.392(2) . ?
N5 H5 0.82(2) . ?
N6 C13 1.347(2) . ?
N6 C14 1.469(3) . ?
N6 H6 0.80(2) . ?
C1 H1A 1.0000 . ?
C1 C2 1.519(3) . ?
C1 C8 1.525(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.386(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4A 0.9500 . ?
C4 C5 1.381(3) . ?
C5 H5A 0.9500 . ?
C5 C6 1.382(3) . ?
C6 H6A 0.9500 . ?
C6 C7 1.391(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 C11 1.522(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.518(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.520(3) . ?
C14 C21 1.509(3) . ?
C15 C16 1.381(3) . ?
C15 C20 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.371(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C1 N1 H1 115.4(14) . . ?
C9 N1 C1 121.17(15) . . ?
C9 N1 H1 118.3(14) . . ?
N3 N2 H2 115.2(14) . . ?
C9 N2 N3 119.82(15) . . ?
C9 N2 H2 118.2(14) . . ?
N2 N3 H3 116.8(17) . . ?
C10 N3 N2 121.83(16) . . ?
C10 N3 H3 121.3(17) . . ?
N5 N4 H4 119.4(14) . . ?
C12 N4 N5 120.08(15) . . ?
C12 N4 H4 120.4(14) . . ?
N4 N5 C13 117.48(15) . . ?
N4 N5 H5 114.7(15) . . ?
C13 N5 H5 116.7(15) . . ?
C13 N6 C14 121.18(16) . . ?
C13 N6 H6 115.0(17) . . ?
C14 N6 H6 121.7(17) . . ?
N1 C1 H1A 108.2 . . ?
N1 C1 C2 110.15(15) . . ?
N1 C1 C8 108.94(15) . . ?
C2 C1 H1A 108.2 . . ?
C2 C1 C8 112.89(15) . . ?
C8 C1 H1A 108.2 . . ?
C3 C2 C1 120.99(17) . . ?
C7 C2 C1 120.49(17) . . ?
C7 C2 C3 118.50(18) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 C2 120.47(19) . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 H5A 120.2 . . ?
C4 C5 C6 119.6(2) . . ?
C6 C5 H5A 120.2 . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 C7 119.9(2) . . ?
C7 C6 H6A 120.0 . . ?
C2 C7 C6 120.9(2) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N1 123.34(17) . . ?
O1 C9 N2 119.58(16) . . ?
N1 C9 N2 117.02(16) . . ?
O2 C10 N3 123.86(17) . . ?
O2 C10 C11 122.94(16) . . ?
N3 C10 C11 112.96(16) . . ?
C10 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 C10 107.56(15) . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
O3 C12 N4 122.26(17) . . ?
O3 C12 C11 121.94(16) . . ?
N4 C12 C11 115.79(15) . . ?
O4 C13 N5 122.07(17) . . ?
O4 C13 N6 123.51(18) . . ?
N6 C13 N5 114.36(16) . . ?
N6 C14 H14 106.8 . . ?
N6 C14 C15 110.05(17) . . ?
N6 C14 C21 110.96(19) . . ?
C15 C14 H14 106.8 . . ?
C21 C14 H14 106.8 . . ?
C21 C14 C15 115.01(18) . . ?
C16 C15 C14 123.0(2) . . ?
C16 C15 C20 117.5(2) . . ?
C20 C15 C14 119.3(2) . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.8(2) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.2(2) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 121.1(2) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.86(2) 2.09(2) 2.931(2) 166(2) . yes
N2 H2 O4 0.89(2) 1.90(2) 2.770(2) 162(2) 2_645 yes
N3 H3 O1 0.84(2) 2.04(2) 2.884(2) 179(2) 2_655 yes
N4 H4 O1 0.87(2) 2.06(2) 2.920(2) 165.8(19) 1_565 yes
N5 H5 O2 0.82(2) 2.41(2) 3.107(2) 144.4(19) 3_676 yes
N5 H5 O3 0.82(2) 2.52(2) 3.136(2) 133.7(18) 3_676 yes
N6 H6 O2 0.80(2) 2.15(2) 2.932(2) 166(2) 3_676 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 N2 N3 21.1(2) . . . . ?
N2 N3 C10 O2 -5.4(3) . . . . ?
N3 N2 C9 O1 -161.74(16) . . . . ?
N4 N5 C13 O4 21.1(2) . . . . ?
N5 N4 C12 O3 -2.8(3) . . . . ?
N6 C13 N5 N4 -161.50(16) . . . . ?
C1 N1 C9 O1 22.4(3) . . . . ?
C1 N1 C9 N2 -160.50(16) . . . . ?
C2 C1 N1 C9 73.7(2) . . . . ?
C3 C2 C1 N1 47.7(2) . . . . ?
C3 C2 C1 C8 -74.3(2) . . . . ?
C7 C2 C1 N1 -130.64(19) . . . . ?
C7 C2 C1 C8 107.3(2) . . . . ?
C8 C1 N1 C9 -161.93(16) . . . . ?
C9 N2 N3 C10 -93.4(2) . . . . ?
C10 C11 C12 O3 -10.1(2) . . . . ?
C10 C11 C12 N4 171.46(15) . . . . ?
C11 C10 N3 N2 169.12(15) . . . . ?
C11 C12 N4 N5 175.68(15) . . . . ?
C12 N4 N5 C13 74.3(2) . . . . ?
C12 C11 C10 O2 96.3(2) . . . . ?
C12 C11 C10 N3 -78.32(19) . . . . ?
C14 N6 C13 O4 12.5(3) . . . . ?
C14 N6 C13 N5 -164.90(17) . . . . ?
C15 C14 N6 C13 -139.43(19) . . . . ?
C16 C15 C14 N6 -133.3(2) . . . . ?
C16 C15 C14 C21 -7.2(3) . . . . ?
C20 C15 C14 N6 51.1(3) . . . . ?
C20 C15 C14 C21 177.3(2) . . . . ?
C21 C14 N6 C13 92.1(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_1RR_DH_19srv179
_database_code_depnum_ccdc_archive 'CCDC 2222823'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record             
;
2022-11-28 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_audit_creation_date             2019-05-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 N6 O4, 2(H2 O)'
_chemical_formula_sum            'C21 H30 N6 O6'
_chemical_formula_weight         462.51
_chemical_absolute_configuration unk
_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 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0108 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.300(3)
_cell_length_b                   4.5408(11)
_cell_length_c                   21.909(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.897(7)
_cell_angle_gamma                90
_cell_volume                     1124.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2808
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      24.15
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1353 before and 0.0469 after correction. 
The Ratio of minimum to maximum transmission is 0.4009. 
The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.5207
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.2213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         0.901
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'Dectris Pilatus 2M'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'φ and ω rotation with 0.1 degree frames'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                2685
_reflns_number_total             5176
_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_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection       'GDA 8.44; generic data acquisition software'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1761
_refine_ls_R_factor_gt           0.1179
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1410P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3080
_refine_ls_wR_factor_ref         0.3656
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.969(2)
 0.031(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3.a Free rotating group:
 O5(H5A,H5B), O6(H6A,H6B)
3.b Ternary CH refined with riding coordinates:
 C1(H1A), C7(H7)
3.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
3.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7230(6) 0.2204(13) 0.3270(3) 0.0605(17) Uani 1 1 d . . . . .
O2 O 0.7093(9) 0.644(2) 0.4583(3) 0.087(3) Uani 1 1 d . . . . .
O3 O 0.9446(9) 0.608(2) 0.5797(3) 0.090(3) Uani 1 1 d . . . . .
O4 O 0.8342(7) 0.2269(13) 0.7015(3) 0.0650(19) Uani 1 1 d . . . . .
N1 N 0.6809(7) 0.6541(17) 0.2797(3) 0.0559(18) Uani 1 1 d . . . . .
H1 H 0.702314 0.838978 0.275002 0.067 Uiso 1 1 calc R . . . .
N2 N 0.8227(8) 0.6336(19) 0.3546(3) 0.067(2) Uani 1 1 d . . . . .
H2 H 0.850708 0.805732 0.343295 0.080 Uiso 1 1 calc R . . . .
N3 N 0.8628(9) 0.4952(18) 0.4073(3) 0.067(2) Uani 1 1 d . . . . .
H3 H 0.931709 0.404938 0.407838 0.080 Uiso 1 1 calc R . . . .
N4 N 0.7571(9) 0.490(2) 0.6002(3) 0.067(2) Uani 1 1 d . . . . .
H4 H 0.691450 0.403182 0.587658 0.081 Uiso 1 1 calc R . . . .
N5 N 0.7622(8) 0.6380(18) 0.6553(3) 0.061(2) Uani 1 1 d . . . . .
H5 H 0.729724 0.812551 0.660019 0.073 Uiso 1 1 calc R . . . .
N6 N 0.8570(7) 0.6695(15) 0.7478(3) 0.0543(18) Uani 1 1 d . . . . .
H6 H 0.839326 0.858173 0.746432 0.065 Uiso 1 1 calc R . . . .
C1 C 0.5844(9) 0.540(2) 0.2417(4) 0.062(2) Uani 1 1 d . . . . .
H1A H 0.598691 0.324607 0.235710 0.074 Uiso 1 1 calc R . . . .
C2 C 0.7382(9) 0.4915(19) 0.3211(4) 0.054(2) Uani 1 1 d . . . . .
C3 C 0.7975(13) 0.499(2) 0.4566(4) 0.075(3) Uani 1 1 d . . . . .
C4 C 0.8377(15) 0.302(2) 0.5083(4) 0.084(4) Uani 1 1 d . . . . .
H4A H 0.913579 0.207112 0.497756 0.101 Uiso 1 1 calc R . . . .
H4B H 0.778307 0.145465 0.514704 0.101 Uiso 1 1 calc R . . . .
C5 C 0.8538(12) 0.482(2) 0.5669(4) 0.066(3) Uani 1 1 d . . . . .
C6 C 0.8211(8) 0.4963(19) 0.7024(4) 0.052(2) Uani 1 1 d . . . . .
C7 C 0.9253(8) 0.556(2) 0.8005(4) 0.055(2) Uani 1 1 d . . . . .
H7 H 0.893752 0.357114 0.811201 0.065 Uiso 1 1 calc R . . . .
C8 C 0.9038(8) 0.7621(17) 0.8537(4) 0.050(2) Uani 1 1 d . . . . .
C9 C 0.9944(8) 0.869(2) 0.8908(4) 0.055(2) Uani 1 1 d . . . . .
H9 H 1.074138 0.813798 0.883576 0.066 Uiso 1 1 calc R . . . .
C10 C 0.9675(11) 1.058(2) 0.9389(4) 0.064(3) Uani 1 1 d . . . . .
H10 H 1.029724 1.134783 0.963886 0.076 Uiso 1 1 calc R . . . .
C11 C 0.8568(10) 1.132(2) 0.9502(4) 0.059(2) Uani 1 1 d . . . . .
H11 H 0.841116 1.262161 0.983103 0.071 Uiso 1 1 calc R . . . .
C12 C 0.7634(9) 1.025(2) 0.9155(4) 0.064(2) Uani 1 1 d . . . . .
H12 H 0.684001 1.076520 0.924252 0.077 Uiso 1 1 calc R . . . .
C13 C 0.7900(9) 0.836(2) 0.8663(4) 0.057(2) Uani 1 1 d . . . . .
H13 H 0.727402 0.759008 0.841664 0.068 Uiso 1 1 calc R . . . .
C14 C 1.0535(10) 0.523(3) 0.7841(5) 0.075(3) Uani 1 1 d . . . . .
H14A H 1.059795 0.396505 0.748059 0.113 Uiso 1 1 calc GR . . . .
H14B H 1.097232 0.434253 0.818371 0.113 Uiso 1 1 calc GR . . . .
H14C H 1.086805 0.717334 0.775110 0.113 Uiso 1 1 calc GR . . . .
C15 C 0.4697(10) 0.573(3) 0.2765(5) 0.081(3) Uani 1 1 d . . . . .
H15A H 0.480507 0.493648 0.317864 0.122 Uiso 1 1 calc GR . . . .
H15B H 0.406497 0.463678 0.255299 0.122 Uiso 1 1 calc GR . . . .
H15C H 0.448262 0.781320 0.278821 0.122 Uiso 1 1 calc GR . . . .
C16 C 0.5862(8) 0.683(2) 0.1800(4) 0.056(2) Uani 1 1 d . . . . .
C17 C 0.6802(11) 0.637(3) 0.1433(5) 0.077(3) Uani 1 1 d . . . . .
H17 H 0.743856 0.517380 0.157628 0.092 Uiso 1 1 calc R . . . .
C18 C 0.6854(11) 0.760(3) 0.0854(5) 0.081(3) Uani 1 1 d . . . . .
H18 H 0.752657 0.724561 0.061050 0.097 Uiso 1 1 calc R . . . .
C19 C 0.5962(11) 0.931(2) 0.0630(5) 0.069(3) Uani 1 1 d . . . . .
H19 H 0.598791 1.010090 0.022887 0.083 Uiso 1 1 calc R . . . .
C20 C 0.5026(12) 0.985(3) 0.1001(6) 0.089(4) Uani 1 1 d . . . . .
H20 H 0.440422 1.109329 0.086143 0.106 Uiso 1 1 calc R . . . .
C21 C 0.4966(10) 0.861(3) 0.1577(5) 0.072(3) Uani 1 1 d . . . . .
H21 H 0.429687 0.898481 0.182261 0.086 Uiso 1 1 calc R . . . .
O5 O 0.4251(10) 0.619(3) 0.4449(5) 0.108(3) Uani 1 1 d . . . . .
H5A H 0.465469 0.617660 0.479039 0.162 Uiso 1 1 d G . . . .
H5B H 0.458213 0.484751 0.422693 0.162 Uiso 1 1 d G . . . .
O6 O 0.4611(12) 0.616(3) 0.5788(6) 0.125(4) Uani 1 1 d . . . . .
H6A H 0.492359 0.493463 0.605038 0.187 Uiso 1 1 d G . . . .
H6B H 0.385173 0.597496 0.583606 0.187 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.250(11) . ?
O2 C3 1.197(15) . ?
O3 C5 1.204(14) . ?
O4 C6 1.232(11) . ?
N1 H1 0.8800 . ?
N1 C1 1.457(11) . ?
N1 C2 1.330(11) . ?
N2 H2 0.8800 . ?
N2 N3 1.385(10) . ?
N2 C2 1.359(12) . ?
N3 H3 0.8800 . ?
N3 C3 1.318(16) . ?
N4 H4 0.8800 . ?
N4 N5 1.381(11) . ?
N4 C5 1.324(15) . ?
N5 H5 0.8800 . ?
N5 C6 1.379(11) . ?
N6 H6 0.8800 . ?
N6 C6 1.327(10) . ?
N6 C7 1.472(10) . ?
C1 H1A 1.0000 . ?
C1 C15 1.521(15) . ?
C1 C16 1.501(14) . ?
C3 C4 1.506(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.532(13) . ?
C7 H7 1.0000 . ?
C7 C8 1.517(12) . ?
C7 C14 1.505(15) . ?
C8 C9 1.385(13) . ?
C8 C13 1.362(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.398(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.323(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(14) . ?
C12 H12 0.9500 . ?
C12 C13 1.413(13) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.358(15) . ?
C16 C21 1.377(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.357(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.367(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(17) . ?
C21 H21 0.9500 . ?
O5 H5A 0.8699 . ?
O5 H5B 0.8701 . ?
O6 H6A 0.8698 . ?
O6 H6B 0.8697 . ?

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
C1 N1 H1 118.5 . . ?
C2 N1 H1 118.5 . . ?
C2 N1 C1 123.0(7) . . ?
N3 N2 H2 121.5 . . ?
C2 N2 H2 121.5 . . ?
C2 N2 N3 116.9(8) . . ?
N2 N3 H3 120.0 . . ?
C3 N3 N2 119.9(10) . . ?
C3 N3 H3 120.0 . . ?
N5 N4 H4 121.0 . . ?
C5 N4 H4 121.0 . . ?
C5 N4 N5 118.0(9) . . ?
N4 N5 H5 122.0 . . ?
C6 N5 N4 116.1(7) . . ?
C6 N5 H5 122.0 . . ?
C6 N6 H6 119.0 . . ?
C6 N6 C7 122.1(7) . . ?
C7 N6 H6 119.0 . . ?
N1 C1 H1A 107.6 . . ?
N1 C1 C15 108.4(8) . . ?
N1 C1 C16 109.8(7) . . ?
C15 C1 H1A 107.6 . . ?
C16 C1 H1A 107.6 . . ?
C16 C1 C15 115.7(8) . . ?
O1 C2 N1 123.5(8) . . ?
O1 C2 N2 120.6(8) . . ?
N1 C2 N2 115.8(8) . . ?
O2 C3 N3 120.6(10) . . ?
O2 C3 C4 123.1(11) . . ?
N3 C3 C4 116.3(12) . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C3 C4 C5 110.2(9) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
O3 C5 N4 124.6(10) . . ?
O3 C5 C4 122.5(11) . . ?
N4 C5 C4 112.8(11) . . ?
O4 C6 N5 120.6(8) . . ?
O4 C6 N6 124.4(8) . . ?
N6 C6 N5 115.0(7) . . ?
N6 C7 H7 108.4 . . ?
N6 C7 C8 107.3(7) . . ?
N6 C7 C14 110.0(8) . . ?
C8 C7 H7 108.4 . . ?
C14 C7 H7 108.4 . . ?
C14 C7 C8 114.3(8) . . ?
C9 C8 C7 122.7(9) . . ?
C13 C8 C7 118.1(8) . . ?
C13 C8 C9 119.1(9) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(9) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(9) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(9) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.7(10) . . ?
C13 C12 H12 121.1 . . ?
C8 C13 C12 121.2(8) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C15 H15A 109.5 . . ?
C1 C15 H15B 109.5 . . ?
C1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C1 119.2(9) . . ?
C17 C16 C21 117.3(10) . . ?
C21 C16 C1 123.5(10) . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.5(10) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.3(11) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 121.2 . . ?
C18 C19 C20 117.6(11) . . ?
C20 C19 H19 121.2 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.3(11) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 C20 120.9(11) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
H5A O5 H5B 104.5 . . ?
H6A O6 H6B 104.5 . . ?

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 O1 0.88 2.08 2.810(9) 139.3 1_565 yes
N2 H2 O1 0.88 2.40 2.952(10) 121.4 1_565 yes
N3 H3 O3 0.88 1.96 2.808(13) 162.2 2_746 yes
N4 H4 O5 0.88 1.97 2.825(14) 164.2 2_646 yes
N5 H5 O4 0.88 2.39 2.968(10) 123.3 1_565 yes
N6 H6 O4 0.88 1.94 2.737(9) 149.5 1_565 yes
O5 H5A O6 0.87 2.19 2.956(17) 147.0 . yes
O5 H5B O6 0.87 1.91 2.679(18) 146.8 2_646 yes
O6 H6A O5 0.87 2.23 2.65(2) 109.3 2_646 yes
O6 H6B O1 0.87 2.39 2.991(15) 126.5 2_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 N2 N3 164.4(9) . . . . ?
N2 N3 C3 O2 -7.2(16) . . . . ?
N3 N2 C2 O1 -20.3(15) . . . . ?
N4 N5 C6 O4 -22.1(15) . . . . ?
N5 N4 C5 O3 -4.0(15) . . . . ?
N6 C6 N5 N4 160.2(9) . . . . ?
C1 N1 C2 O1 7.5(16) . . . . ?
C1 N1 C2 N2 -177.3(9) . . . . ?
C2 N2 N3 C3 -77.0(12) . . . . ?
C3 C4 C5 O3 -86.6(15) . . . . ?
C3 C4 C5 N4 91.5(13) . . . . ?
C4 C3 N3 N2 170.2(9) . . . . ?
C4 C5 N4 N5 177.9(8) . . . . ?
C5 N4 N5 C6 -75.4(11) . . . . ?
C5 C4 C3 O2 -57.8(16) . . . . ?
C5 C4 C3 N3 124.9(12) . . . . ?
C7 N6 C6 O4 4.9(16) . . . . ?
C7 N6 C6 N5 -177.5(9) . . . . ?
C8 C7 N6 C6 -155.0(8) . . . . ?
C9 C8 C7 N6 -133.3(9) . . . . ?
C9 C8 C7 C14 -11.1(12) . . . . ?
C13 C8 C7 N6 49.0(11) . . . . ?
C13 C8 C7 C14 171.2(9) . . . . ?
C14 C7 N6 C6 80.2(12) . . . . ?
C15 C1 N1 C2 86.4(12) . . . . ?
C15 C1 C16 C17 -172.8(11) . . . . ?
C15 C1 C16 C21 6.8(14) . . . . ?
C16 C1 N1 C2 -146.4(9) . . . . ?
C17 C16 C1 N1 64.2(12) . . . . ?
C21 C16 C1 N1 -116.3(11) . . . . ?


# start Validation Reply Form
_vrf_PLAT084_1RR_DH_19srv179     
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.37 Report
RESPONSE:  The diffraction from these thin needles was found to be very weak 
in spite of using a synchrotron source for data collection. More than 90% of 
reflections above 0.82 Ang were unobserved (i.e. less than 2 sigma (I)). 
Nevertheless the structure was succesfully solved and refined but some formal 
refinement criteria and precision of geometrical parameters were affected by 
such weak diffraction.
;
_vrf_PLAT340_1RR_DH_19srv179     
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01444 Ang.  
RESPONSE: The diffraction from these thin needles was found to be very weak 
in spite of using a synchrotron source for data collection. More than 90% of 
reflections above 0.82 Ang were unobserved (i.e. less than 2 sigma (I)). 
Nevertheless the structure was succesfully solved and refined but some formal 
refinement criteria and precision of geometrical parameters were affected by 
such weak diffraction.
;
# end Validation Reply Form

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.969(2)
2 0.031(2)

