# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_n16053_0m
_database_code_depnum_ccdc_archive 'CCDC 1560512'
_audit_update_record             
;
2017-07-05 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H16 N10 O4, 2(C2 H5.11 O), 2(C H4 O)'
_chemical_formula_sum            'C30 H34.28 N10 O8'
_chemical_formula_weight         662.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   23.096(4)
_cell_length_b                   17.557(3)
_cell_length_c                   9.0150(17)
_cell_angle_alpha                90
_cell_angle_beta                 112.545(4)
_cell_angle_gamma                90
_cell_volume                     3376.3(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      66.64
_cell_measurement_theta_min      3.26
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.696
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0645 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.8539.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1393
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.269
_exptl_crystal_size_min          0.191
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            30930
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         66.713
_diffrn_reflns_theta_min         3.260
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2645
_reflns_number_total             2938
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.877
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.114
_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)+(0.1327P)²+7.0151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2167
_refine_ls_wR_factor_ref         0.2211
_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, All O(H) groups
2. Restrained distances
 C14-C13 = C14A-C13
 1.54 with sigma of 0.02
 O3-H3
 0.84 with sigma of 0.02
 O4-C16
 1.42 with sigma of 0.01
 N4-H4B \\sim N4-H4A \\sim N5-H5B \\sim N5-H5A
 with sigma of 0.02
 C14-C13 \\sim C14A-C13
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O3, C13, C14, C14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O5, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O4, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=1-FVAR(1)
 Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=FVAR(1)
 Fixed Sof: O4(0.5) H4C(0.5) O5(0.5) H5C(0.5) C15(0.5) H15A(0.5) H15B(0.5)
 H15C(0.5) C16(0.5) H16A(0.5) H16B(0.5) H16C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14A(H14D,H14E,H14F), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
5.d Idealised tetrahedral OH refined as rotating group:
 O4(H4C), O5(H5C)
;
_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 0.32370(10) 0.36070(11) 0.4437(3) 0.0477(6) Uani 1 1 d . . . . .
O2 O 0.26277(10) 0.10288(11) 0.4089(3) 0.0459(6) Uani 1 1 d . . . . .
O3 O 0.40713(10) 0.15302(13) 0.7582(2) 0.0453(6) Uani 1 1 d D U . . .
O4 O 0.4665(6) 0.4312(7) 0.8009(15) 0.168(5) Uani 0.5 1 d D U P A -1
H4C H 0.4953 0.4334 0.8926 0.252 Uiso 0.5 1 calc GR . P A -1
O5 O 0.5043(5) 0.4538(5) 1.1178(12) 0.118(3) Uani 0.5 1 d . U P B -1
H5C H 0.4888 0.4813 1.1693 0.178 Uiso 0.5 1 calc GR . P B -1
N1 N 0.39176(9) 0.19274(12) 0.4351(2) 0.0251(5) Uani 1 1 d . . . . .
N2 N 0.41176(9) 0.18803(12) 0.1936(2) 0.0255(5) Uani 1 1 d . . . . .
N3 N 0.31104(9) 0.22582(12) 0.1855(2) 0.0240(5) Uani 1 1 d . . . . .
N4 N 0.48901(10) 0.16247(15) 0.4386(3) 0.0343(6) Uani 1 1 d D . . . .
N5 N 0.33080(10) 0.21827(14) -0.0446(2) 0.0299(5) Uani 1 1 d D . . . .
C1 C 0.29115(10) 0.23246(14) 0.4258(3) 0.0237(5) Uani 1 1 d . . . . .
C2 C 0.28593(12) 0.30680(15) 0.4719(3) 0.0288(6) Uani 1 1 d . . . . .
C3 C 0.31358(15) 0.43544(17) 0.4798(4) 0.0416(7) Uani 1 1 d . . . . .
C4 C 0.34744(15) 0.49221(18) 0.4442(4) 0.0441(7) Uani 1 1 d . . . . .
H4 H 0.3777 0.4800 0.4003 0.053 Uiso 1 1 calc R . . . .
C5 C 0.33684(15) 0.56734(18) 0.4733(4) 0.0460(8) Uani 1 1 d . . . . .
H5 H 0.3602 0.6067 0.4498 0.055 Uiso 1 1 calc R . . . .
C6 C 0.29274(15) 0.58565(18) 0.5359(4) 0.0453(8) Uani 1 1 d . . . . .
H6 H 0.2854 0.6374 0.5537 0.054 Uiso 1 1 calc R . . . .
C7 C 0.24097(15) -0.02807(17) 0.4269(4) 0.0434(7) Uani 1 1 d . . . . .
H7 H 0.2715 -0.0403 0.3839 0.052 Uiso 1 1 calc R . . . .
C8 C 0.22962(14) 0.04645(17) 0.4530(4) 0.0406(7) Uani 1 1 d . . . . .
C9 C 0.25542(12) 0.17594(14) 0.4545(3) 0.0274(6) Uani 1 1 d . . . . .
C10 C 0.33448(11) 0.21528(14) 0.3428(3) 0.0231(5) Uani 1 1 d . . . . .
C11 C 0.42996(11) 0.18163(14) 0.3536(3) 0.0253(5) Uani 1 1 d . . . . .
C12 C 0.35224(11) 0.21010(14) 0.1145(3) 0.0235(5) Uani 1 1 d . . . . .
C13 C 0.3854(3) 0.0771(2) 0.7505(6) 0.0840(14) Uani 1 1 d D U . . .
H13A H 0.3418 0.0731 0.6707 0.101 Uiso 0.556(10) 1 calc R . P C 2
H13B H 0.3861 0.0612 0.8565 0.101 Uiso 0.556(10) 1 calc R . P C 2
C14 C 0.4270(6) 0.0283(5) 0.7036(14) 0.109(4) Uani 0.556(10) 1 d D U P C 2
H14A H 0.4226 -0.0246 0.7322 0.164 Uiso 0.556(10) 1 calc GR . P C 2
H14B H 0.4705 0.0448 0.7598 0.164 Uiso 0.556(10) 1 calc GR . P C 2
H14C H 0.4156 0.0321 0.5873 0.164 Uiso 0.556(10) 1 calc GR . P C 2
C14A C 0.4009(5) 0.0245(6) 0.8699(13) 0.075(3) Uani 0.444(10) 1 d D U P C 1
H14D H 0.4424 0.0035 0.8881 0.112 Uiso 0.444(10) 1 calc GR . P C 1
H14E H 0.3698 -0.0165 0.8391 0.112 Uiso 0.444(10) 1 calc GR . P C 1
H14F H 0.4018 0.0487 0.9687 0.112 Uiso 0.444(10) 1 calc GR . P C 1
C15 C 0.5107(4) 0.3755(4) 1.1794(9) 0.0617(19) Uani 0.5 1 d . U P B -1
H15A H 0.4899 0.3710 1.2554 0.093 Uiso 0.5 1 calc GR . P B -1
H15B H 0.5552 0.3629 1.2339 0.093 Uiso 0.5 1 calc GR . P B -1
H15C H 0.4912 0.3401 1.0898 0.093 Uiso 0.5 1 calc GR . P B -1
C16 C 0.4665(5) 0.3565(7) 0.7318(16) 0.121(4) Uani 0.5 1 d D U P A -1
H16A H 0.5095 0.3423 0.7478 0.181 Uiso 0.5 1 calc GR . P A -1
H16B H 0.4407 0.3578 0.6165 0.181 Uiso 0.5 1 calc GR . P A -1
H16C H 0.4493 0.3190 0.7842 0.181 Uiso 0.5 1 calc GR . P A -1
H3 H 0.405(3) 0.168(3) 0.664(4) 0.101(18) Uiso 1 1 d D . . . .
H4A H 0.5172(13) 0.1664(18) 0.399(4) 0.040(8) Uiso 1 1 d D . . . .
H4B H 0.5022(15) 0.1597(19) 0.541(3) 0.045(9) Uiso 1 1 d D . . . .
H5A H 0.2931(11) 0.2324(19) -0.092(4) 0.046(9) Uiso 1 1 d D . . . .
H5B H 0.3545(13) 0.2069(18) -0.093(4) 0.038(8) Uiso 1 1 d 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 C2 1.375(3) . ?
O1 C3 1.393(3) . ?
O2 C8 1.400(3) . ?
O2 C9 1.377(3) . ?
O3 C13 1.416(5) . ?
O3 H3 0.87(2) . ?
O4 H4C 0.8400 . ?
O4 C16 1.452(9) . ?
O5 H5C 0.8400 . ?
O5 C15 1.468(12) . ?
N1 C10 1.325(3) . ?
N1 C11 1.361(3) . ?
N2 C11 1.344(3) . ?
N2 C12 1.340(3) . ?
N3 C10 1.323(3) . ?
N3 C12 1.363(3) . ?
N4 C11 1.326(3) . ?
N4 H4A 0.86(2) . ?
N4 H4B 0.86(2) . ?
N5 C12 1.334(3) . ?
N5 H5A 0.85(2) . ?
N5 H5B 0.85(2) . ?
C1 C2 1.389(4) . ?
C1 C9 1.377(4) . ?
C1 C10 1.492(3) . ?
C2 C9 1.389(3) 7_556 ?
C3 C4 1.379(4) . ?
C3 C8 1.388(4) 7_556 ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.393(4) 7_556 ?
C7 C6 1.393(4) 7_556 ?
C7 H7 0.9500 . ?
C7 C8 1.372(4) . ?
C8 C3 1.388(4) 7_556 ?
C9 C2 1.389(3) 7_556 ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.465(10) . ?
C13 C14A 1.358(9) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C2 O1 C3 115.5(2) . . ?
C9 O2 C8 115.5(2) . . ?
C13 O3 H3 110(4) . . ?
C16 O4 H4C 109.5 . . ?
C15 O5 H5C 109.5 . . ?
C10 N1 C11 113.7(2) . . ?
C12 N2 C11 115.46(19) . . ?
C10 N3 C12 113.74(19) . . ?
C11 N4 H4A 121(2) . . ?
C11 N4 H4B 120(2) . . ?
H4A N4 H4B 116(3) . . ?
C12 N5 H5A 117(2) . . ?
C12 N5 H5B 119(2) . . ?
H5A N5 H5B 123(3) . . ?
C2 C1 C10 119.5(2) . . ?
C9 C1 C2 119.6(2) . . ?
C9 C1 C10 120.9(2) . . ?
O1 C2 C1 117.2(2) . . ?
O1 C2 C9 122.6(2) . 7_556 ?
C9 C2 C1 120.1(2) 7_556 . ?
C4 C3 O1 117.8(3) . . ?
C4 C3 C8 120.2(3) . 7_556 ?
C8 C3 O1 122.0(3) 7_556 . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.9(3) . 7_556 ?
C7 C6 H6 120.1 7_556 . ?
C6 C7 H7 120.3 7_556 . ?
C8 C7 C6 119.3(3) . 7_556 ?
C8 C7 H7 120.3 . . ?
C3 C8 O2 121.7(3) 7_556 . ?
C7 C8 O2 117.7(3) . . ?
C7 C8 C3 120.6(3) . 7_556 ?
O2 C9 C2 122.1(2) . 7_556 ?
C1 C9 O2 117.6(2) . . ?
C1 C9 C2 120.3(2) . 7_556 ?
N1 C10 C1 116.5(2) . . ?
N3 C10 N1 127.9(2) . . ?
N3 C10 C1 115.6(2) . . ?
N2 C11 N1 124.5(2) . . ?
N4 C11 N1 117.4(2) . . ?
N4 C11 N2 118.1(2) . . ?
N2 C12 N3 124.5(2) . . ?
N5 C12 N2 119.0(2) . . ?
N5 C12 N3 116.4(2) . . ?
O3 C13 H13A 110.1 . . ?
O3 C13 H13B 110.1 . . ?
O3 C13 C14 107.8(5) . . ?
H13A C13 H13B 108.5 . . ?
C14 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
C14A C13 O3 128.3(7) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C14A H14D 109.5 . . ?
C13 C14A H14E 109.5 . . ?
C13 C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 177.7(3) . . . . ?
C2 O1 C3 C4 -176.0(3) . . . . ?
C2 O1 C3 C8 3.0(5) . . . 7_556 ?
C2 C1 C9 O2 -179.1(2) . . . . ?
C2 C1 C9 C2 0.5(4) . . . 7_556 ?
C2 C1 C10 N1 94.0(3) . . . . ?
C2 C1 C10 N3 -84.9(3) . . . . ?
C3 O1 C2 C1 175.1(2) . . . . ?
C3 O1 C2 C9 -5.9(4) . . . 7_556 ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C4 C5 C6 C7 1.1(5) . . . 7_556 ?
C6 C7 C8 O2 -177.8(3) 7_556 . . . ?
C6 C7 C8 C3 1.9(5) 7_556 . . 7_556 ?
C8 O2 C9 C1 174.6(2) . . . . ?
C8 O2 C9 C2 -4.9(4) . . . 7_556 ?
C8 C3 C4 C5 -1.3(5) 7_556 . . . ?
C9 O2 C8 C3 7.7(4) . . . 7_556 ?
C9 O2 C8 C7 -172.6(3) . . . . ?
C9 C1 C2 O1 178.6(2) . . . . ?
C9 C1 C2 C9 -0.5(4) . . . 7_556 ?
C9 C1 C10 N1 -87.3(3) . . . . ?
C9 C1 C10 N3 93.8(3) . . . . ?
C10 N1 C11 N2 -3.8(4) . . . . ?
C10 N1 C11 N4 176.9(2) . . . . ?
C10 N3 C12 N2 -1.8(4) . . . . ?
C10 N3 C12 N5 178.7(2) . . . . ?
C10 C1 C2 O1 -2.7(4) . . . . ?
C10 C1 C2 C9 178.3(2) . . . 7_556 ?
C10 C1 C9 O2 2.2(4) . . . . ?
C10 C1 C9 C2 -178.3(2) . . . 7_556 ?
C11 N1 C10 N3 1.8(4) . . . . ?
C11 N1 C10 C1 -176.9(2) . . . . ?
C11 N2 C12 N3 0.1(4) . . . . ?
C11 N2 C12 N5 179.5(2) . . . . ?
C12 N2 C11 N1 2.9(4) . . . . ?
C12 N2 C11 N4 -177.8(2) . . . . ?
C12 N3 C10 N1 0.8(4) . . . . ?
C12 N3 C10 C1 179.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_DIFMX01_n16053_0m           
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: From the SHELX .lst file:
 Electron density synthesis with coefficients Fo-Fc

 Highest peak    0.88  at  0.0000  0.1780  0.2500  [  0.42 A from H16A ]
 Deepest hole   -0.40  at  0.9773  0.0859  0.3377  [  0.45 A from O4 ]
;
_vrf_PLAT097_n16053_0m           
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.88 eA-3  
RESPONSE: From the SHELX .lst file:
 Electron density synthesis with coefficients Fo-Fc

 Highest peak    0.88  at  0.0000  0.1780  0.2500  [  0.42 A from H16A ]
 Deepest hole   -0.40  at  0.9773  0.0859  0.3377  [  0.45 A from O4 ]
;
_vrf_DIFMX02_n16053_0m           
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: From the SHELX .lst file:
 Electron density synthesis with coefficients Fo-Fc

 Highest peak    0.88  at  0.0000  0.1780  0.2500  [  0.42 A from H16A ]
 Deepest hole   -0.40  at  0.9773  0.0859  0.3377  [  0.45 A from O4 ]
;
_vrf_PLAT027_n16053_0m           
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      26.00 Degree
RESPONSE: The crystal diffracted weakly and so the data collection cut-off
was selected after careful consideration of initial images.
;
_vrf_PLAT041_n16053_0m           
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: This small difference is due to the inclusion of some partial
occupancy H-atoms on a disordered ethanol molecule. Only half of the 
-CH2- atoms could be suitably AFIXed, while the others are absent from
the model.
;
_vrf_PLAT094_n16053_0m           
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.19 Report
RESPONSE: From the SHELX .lst file:
 Electron density synthesis with coefficients Fo-Fc

 Highest peak    0.88  at  0.0000  0.1780  0.2500  [  0.42 A from H16A ]
 Deepest hole   -0.40  at  0.9773  0.0859  0.3377  [  0.45 A from O4 ]
;
_vrf_PLAT340_n16053_0m           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0045 Ang.  
RESPONSE: This may result from the generally weak diffraction produced by
this crystal.
;
_vrf_PLAT906_n16053_0m           
;
PROBLEM: Large K value in the Analysis of Variance ......      3.390 Check 
RESPONSE: This is only for the Fc/Fc(max) = 0.000; all other values of
Fc/Fc(max) range from 0.969 to 1.142.
;
_vrf_PLAT911_n16053_0m           
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.596         58 Report
RESPONSE: These may have been obstructed by the beamstop, or may have been
too weak to be observed.
;
_vrf_PLAT918_n16053_0m           
;
PROBLEM: Reflection(s) with I(obs) much Smaller I(calc) .          6 Check 
RESPONSE: This may have resulted from weak diffraction, or from partial
obstruction by the beamstop.
;
_vrf_PLAT939_n16053_0m           
;
PROBLEM: Large Value of Not (SHELXL) Weight Optimized S .      12.47       
RESPONSE: No reflections with error/esd greater than 10 were included. This
may have resulted from weak diffraction, where some essentially
unobserved reflections were included in the refinement.
;
_vrf_FORMU01_n16053_0m           
;
PROBLEM:       
RESPONSE: This small difference is due to the inclusion of some partial
occupancy H-atoms on a disordered ethanol molecule.
;
_vrf_PLAT002_n16053_0m           
;
PROBLEM:       
RESPONSE: Disordered ethanol molecules are present, and restraints
were employed in their refinement.
;
_vrf_PLAT007_n16053_0m           
;
PROBLEM:       
RESPONSE: For two partial occupancy ethanol molecules that appeared to
exhibit difficult-to-model disorder, the H-atoms were introduced in
calculated positions. There are five other donor H-atoms in this model
that were introduced in difference map positions, and allowed to refine
isotropically with same distance restraints.
;
_vrf_PLAT300_n16053_0m           
;
PROBLEM:       
RESPONSE: This is an ethanol molecule sitting adjacent to a special
position. When the structure is "grown", the symmetry related
ethanol is present. The constrained occupancy is consistent with this
symmetry operation.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_b16146_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1560513'
_audit_update_record             
;
2017-07-05 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_audit_creation_date             2017-06-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N10 O4'
_chemical_formula_sum            'C24 H16 N10 O4'
_chemical_formula_weight         508.47
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.955(2)
_cell_length_b                   9.0316(15)
_cell_length_c                   18.918(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.863(9)
_cell_angle_gamma                90
_cell_volume                     1858.4(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      34.34
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.6546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0616 before and 0.0512 after correction. The Ratio of minimum to maximum transmission is 0.8765. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.909
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.608
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.154
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38852
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.048
_diffrn_ambient_temperature      122.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2932
_reflns_number_total             3273
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     240
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0759
_refine_ls_restrained_S_all      1.080
_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)+(0.0982P)²+3.0099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2194
_refine_ls_wR_factor_ref         0.2260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C3-C2 \\sim C3A-C2 \\sim C4-C3 \\sim C4A-C3A \\sim C5-C4 \\sim C5A-C4A \\sim
C6-C5 \\sim C6A-C5A \\sim C7-C6
 \\sim C7-C6A
 with sigma of 0.02
 N4-H4A \\sim N4-H4B \\sim N5-H5A \\sim N5-H5B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C3A)
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4AA)=Sof(C5A)=Sof(H5AA)=Sof(C6A)=Sof(H6A)=1-
 FVAR(1)
 Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C3A(H3A), C4A(H4AA), C5A(H5AA), C6A(H6A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5372(2) 0.3586(3) 0.37530(12) 0.0473(6) Uani 1 1 d . U . . .
O2 O 0.3720(2) 0.6030(3) 0.37552(12) 0.0483(6) Uani 1 1 d . U . . .
N1 N 0.21316(19) 0.7074(2) 0.49906(14) 0.0294(6) Uani 1 1 d . U . . .
N2 N 0.17346(19) 0.9687(2) 0.49849(13) 0.0272(5) Uani 1 1 d . U . . .
N3 N 0.37868(18) 0.8770(2) 0.49985(13) 0.0267(5) Uani 1 1 d . U . . .
N4 N 0.0172(2) 0.7988(3) 0.49783(18) 0.0439(7) Uani 1 1 d D U . . .
H4A H -0.008(3) 0.704(3) 0.4994(19) 0.049(10) Uiso 1 1 d D . . . .
H4B H -0.034(3) 0.876(3) 0.501(2) 0.052(10) Uiso 1 1 d D . . . .
N5 N 0.3381(2) 1.1262(3) 0.49574(16) 0.0372(7) Uani 1 1 d D U . . .
H5A H 0.281(3) 1.199(3) 0.4914(19) 0.050(10) Uiso 1 1 d D . . . .
H5B H 0.420(2) 1.128(5) 0.498(2) 0.066(12) Uiso 1 1 d D . . . .
C1 C 0.5168(2) 0.4306(3) 0.43673(15) 0.0269(6) Uani 1 1 d . U . . .
C2 C 0.4666(4) 0.4069(4) 0.31435(18) 0.0536(9) Uani 1 1 d D U . . .
C7 C 0.3876(4) 0.5258(4) 0.31469(19) 0.0522(9) Uani 1 1 d D U . . .
C8 C 0.4360(2) 0.5486(3) 0.43712(15) 0.0294(6) Uani 1 1 d . U . . .
C9 C 0.4185(2) 0.6176(3) 0.50028(15) 0.0236(6) Uani 1 1 d . U . . .
C10 C 0.3304(2) 0.7437(3) 0.49978(14) 0.0242(6) Uani 1 1 d . U . . .
C11 C 0.1374(2) 0.8272(3) 0.49904(16) 0.0293(6) Uani 1 1 d . U . . .
C12 C 0.2945(2) 0.9889(3) 0.49827(15) 0.0258(6) Uani 1 1 d . U . . .
C3 C 0.503(2) 0.359(2) 0.2491(8) 0.057(3) Uani 0.36(2) 1 d D U P A 1
H3 H 0.571766 0.295530 0.248559 0.069 Uiso 0.36(2) 1 calc R . P A 1
C4 C 0.438(3) 0.406(3) 0.1859(13) 0.085(4) Uani 0.36(2) 1 d D U P A 1
H4 H 0.447325 0.355312 0.142712 0.102 Uiso 0.36(2) 1 calc R . P A 1
C5 C 0.361(3) 0.526(3) 0.1858(16) 0.086(5) Uani 0.36(2) 1 d D U P A 1
H5 H 0.331765 0.575475 0.142722 0.103 Uiso 0.36(2) 1 calc R . P A 1
C6 C 0.325(6) 0.573(8) 0.2503(11) 0.080(3) Uani 0.36(2) 1 d D U P A 1
H6 H 0.257430 0.638358 0.250380 0.096 Uiso 0.36(2) 1 calc R . P A 1
C3A C 0.4694(13) 0.3220(13) 0.2528(5) 0.057(3) Uani 0.64(2) 1 d D U P A 2
H3A H 0.521273 0.237684 0.252685 0.069 Uiso 0.64(2) 1 calc R . P A 2
C4A C 0.3946(16) 0.3641(17) 0.1920(7) 0.085(4) Uani 0.64(2) 1 d D U P A 2
H4AA H 0.396939 0.309343 0.149313 0.102 Uiso 0.64(2) 1 calc R . P A 2
C5A C 0.3166(17) 0.4841(17) 0.1922(8) 0.086(5) Uani 0.64(2) 1 d D U P A 2
H5AA H 0.263539 0.508255 0.150362 0.103 Uiso 0.64(2) 1 calc R . P A 2
C6A C 0.315(4) 0.570(4) 0.2529(7) 0.080(3) Uani 0.64(2) 1 d D U P A 2
H6A H 0.265726 0.656258 0.252272 0.096 Uiso 0.64(2) 1 calc R . P A 2


_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 1.373(3) . ?
O1 C2 1.380(4) . ?
O2 C7 1.374(4) . ?
O2 C8 1.376(4) . ?
N1 C10 1.324(3) . ?
N1 C11 1.364(3) . ?
N2 C11 1.338(3) . ?
N2 C12 1.339(3) . ?
N3 C10 1.314(3) . ?
N3 C12 1.366(3) . ?
N4 H4A 0.91(2) . ?
N4 H4B 0.90(2) . ?
N4 C11 1.339(3) . ?
N5 H5A 0.90(2) . ?
N5 H5B 0.89(2) . ?
N5 C12 1.332(4) . ?
C1 C8 1.386(4) . ?
C1 C9 1.382(4) 3_666 ?
C2 C7 1.380(5) . ?
C2 C3 1.409(13) . ?
C2 C3A 1.398(8) . ?
C7 C6 1.390(13) . ?
C7 C6A 1.390(9) . ?
C8 C9 1.381(4) . ?
C9 C10 1.493(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(15) . ?
C6 H6 0.9500 . ?
C3A H3A 0.9500 . ?
C3A C4A 1.383(9) . ?
C4A H4AA 0.9500 . ?
C4A C5A 1.381(10) . ?
C5A H5AA 0.9500 . ?
C5A C6A 1.386(15) . ?
C6A H6A 0.9500 . ?

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 O1 C2 115.2(2) . . ?
C7 O2 C8 115.3(2) . . ?
C10 N1 C11 113.1(2) . . ?
C11 N2 C12 115.1(2) . . ?
C10 N3 C12 114.0(2) . . ?
H4A N4 H4B 122(3) . . ?
C11 N4 H4A 119(2) . . ?
C11 N4 H4B 118(2) . . ?
H5A N5 H5B 133(4) . . ?
C12 N5 H5A 115(2) . . ?
C12 N5 H5B 112(3) . . ?
O1 C1 C8 122.5(2) . . ?
O1 C1 C9 117.5(2) . 3_666 ?
C9 C1 C8 120.0(3) 3_666 . ?
O1 C2 C3 116.6(11) . . ?
O1 C2 C3A 117.2(6) . . ?
C7 C2 O1 122.1(3) . . ?
C7 C2 C3 119.0(10) . . ?
C7 C2 C3A 120.5(6) . . ?
O2 C7 C2 122.6(3) . . ?
O2 C7 C6 118.8(16) . . ?
O2 C7 C6A 116.4(9) . . ?
C2 C7 C6 118.5(16) . . ?
C2 C7 C6A 120.9(9) . . ?
O2 C8 C1 122.0(3) . . ?
O2 C8 C9 117.6(2) . . ?
C9 C8 C1 120.4(3) . . ?
C1 C9 C10 120.7(2) 3_666 . ?
C8 C9 C1 119.6(2) . 3_666 ?
C8 C9 C10 119.7(2) . . ?
N1 C10 C9 115.9(2) . . ?
N3 C10 N1 128.1(2) . . ?
N3 C10 C9 116.0(2) . . ?
N2 C11 N1 125.3(2) . . ?
N2 C11 N4 118.3(2) . . ?
N4 C11 N1 116.4(2) . . ?
N2 C12 N3 124.4(2) . . ?
N5 C12 N2 119.1(2) . . ?
N5 C12 N3 116.5(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 120(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118(3) . . ?
C6 C5 H5 120.8 . . ?
C7 C6 H6 119.4 . . ?
C5 C6 C7 121(3) . . ?
C5 C6 H6 119.4 . . ?
C2 C3A H3A 120.9 . . ?
C4A C3A C2 118.2(10) . . ?
C4A C3A H3A 120.9 . . ?
C3A C4A H4AA 119.4 . . ?
C5A C4A C3A 121.3(13) . . ?
C5A C4A H4AA 119.4 . . ?
C4A C5A H5AA 119.7 . . ?
C4A C5A C6A 120.6(15) . . ?
C6A C5A H5AA 119.7 . . ?
C7 C6A H6A 120.8 . . ?
C5A C6A C7 118.4(16) . . ?
C5A C6A H6A 120.8 . . ?

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
O1 C1 C8 O2 -1.1(5) . . . . ?
O1 C1 C8 C9 -180.0(3) . . . . ?
O1 C2 C7 O2 -0.9(7) . . . . ?
O1 C2 C7 C6 176(4) . . . . ?
O1 C2 C7 C6A -178(3) . . . . ?
O1 C2 C3 C4 -178.6(14) . . . . ?
O1 C2 C3A C4A 176.8(7) . . . . ?
O2 C7 C6 C5 163(5) . . . . ?
O2 C7 C6A C5A -172(3) . . . . ?
O2 C8 C9 C1 -178.3(2) . . . 3_666 ?
O2 C8 C9 C10 1.5(4) . . . . ?
C1 O1 C2 C7 4.2(6) . . . . ?
C1 O1 C2 C3 166.6(10) . . . . ?
C1 O1 C2 C3A -169.9(8) . . . . ?
C1 C8 C9 C1 0.6(5) . . . 3_666 ?
C1 C8 C9 C10 -179.6(2) . . . . ?
C1 C9 C10 N1 -97.7(3) 3_666 . . . ?
C1 C9 C10 N3 82.5(3) 3_666 . . . ?
C2 O1 C1 C8 -3.3(5) . . . . ?
C2 O1 C1 C9 177.4(3) . . . 3_666 ?
C2 C7 C6 C5 -14(9) . . . . ?
C2 C7 C6A C5A 5(5) . . . . ?
C2 C3 C4 C5 17(3) . . . . ?
C2 C3A C4A C5A -1.7(15) . . . . ?
C7 O2 C8 C1 4.4(5) . . . . ?
C7 O2 C8 C9 -176.7(3) . . . . ?
C7 C2 C3 C4 -16(2) . . . . ?
C7 C2 C3A C4A 2.5(11) . . . . ?
C8 O2 C7 C2 -3.4(6) . . . . ?
C8 O2 C7 C6 179(4) . . . . ?
C8 O2 C7 C6A 174(2) . . . . ?
C8 C9 C10 N1 82.4(3) . . . . ?
C8 C9 C10 N3 -97.3(3) . . . . ?
C9 C1 C8 O2 178.3(3) 3_666 . . . ?
C9 C1 C8 C9 -0.6(5) 3_666 . . . ?
C10 N1 C11 N2 1.2(4) . . . . ?
C10 N1 C11 N4 179.6(3) . . . . ?
C10 N3 C12 N2 1.7(4) . . . . ?
C10 N3 C12 N5 -177.7(3) . . . . ?
C11 N1 C10 N3 -0.6(4) . . . . ?
C11 N1 C10 C9 179.7(2) . . . . ?
C11 N2 C12 N3 -1.2(4) . . . . ?
C11 N2 C12 N5 178.2(3) . . . . ?
C12 N2 C11 N1 -0.3(4) . . . . ?
C12 N2 C11 N4 -178.7(3) . . . . ?
C12 N3 C10 N1 -0.7(4) . . . . ?
C12 N3 C10 C9 179.0(2) . . . . ?
C3 C2 C7 O2 -162.9(11) . . . . ?
C3 C2 C7 C6 14(4) . . . . ?
C3 C4 C5 C6 -16(5) . . . . ?
C4 C5 C6 C7 15(9) . . . . ?
C3A C2 C7 O2 173.0(8) . . . . ?
C3A C2 C7 C6A -4(3) . . . . ?
C3A C4A C5A C6A 3(3) . . . . ?
C4A C5A C6A C7 -4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT213_b16146_0m_sq        
;
PROBLEM: Atom N4              has ADP max/min Ratio .....        3.3 prolat
RESPONSE: Main molecule exhibited some disorder. This was modeled for the
terminal pheny ring, but attempts to model the disorder in the 
diaminotriazine ring did not lead to improvement in refinement 
statistics, and so the simpler model was retained.
;
_vrf_PLAT220_b16146_0m_sq        
;
PROBLEM: Non-Solvent Resd 1   C   Ueq(max)/Ueq(min) Range        3.6 Ratio 
RESPONSE: Main molecule exhibited some disorder. This was modeled for the
terminal pheny ring, but attempts to model the disorder in the 
diaminotriazine ring did not lead to improvement in refinement 
statistics, and so the simpler model was retained.
;
_vrf_PLAT250_b16146_0m_sq        
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note  
RESPONSE: Acknowledged. Main molecule exhibited some disorder. 
This was modeled for the terminal pheny ring, but attempts to model 
the disorder in the diaminotriazine ring did not lead to improvement 
in refinement statistics, and so the simpler model was retained.
;
_vrf_PLAT340_b16146_0m_sq        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0044 Ang.  
RESPONSE: This is consistent with the significant disorder present in
the structure. 
;
_vrf_PLAT420_b16146_0m_sq        
;
PROBLEM: D-H Without Acceptor       N4     --  H4A    ...     Please Check 
RESPONSE: A solvent mask was applie; the acceptor should be a
molecule of acetonitrile, while has been accounted for using the
PLATON Squeeze routine.
;
_vrf_PLAT906_b16146_0m_sq        
;
PROBLEM: Large K value in the Analysis of Variance ......      4.832 Check 
RESPONSE: Examination of the .lst shows that this corresponds to 
Fc/Fc(max) = 0.000. For other values of Fc/Fc(max) the value of K is 
smaller.
;
_vrf_PLAT911_b16146_0m_sq        
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.595          4 Report
RESPONSE: These may have been obstructed by the beamstop.
;
_vrf_PLAT918_b16146_0m_sq        
;
PROBLEM: Reflection(s) with I(obs) much Smaller I(calc) .          2 Check 
RESPONSE: This is a very small number of reflections when compared to the
total number of reflections that were collected.
;
_vrf_PLAT002_b16146_0m_sq        
;
PROBLEM: Number of Distance or Angle Restraints on AtSite         16 Note 
RESPONSE: SADI restraints were applied to the disordered phenyl ring
distances. Separately, SADI restraints were applied to the NH bond 
distances, where H-atoms were located in difference map positions.
;
_vrf_PLAT003_b16146_0m_sq        
;
PROBLEM: Number of Uiso or Uij Restrained non-H Atoms ...         23 Report
RESPONSE: A global RIGU restraint, with default standard uncertainties, was
applied.
;
_vrf_PLAT063_b16146_0m_sq        
;
PROBLEM: Crystal Size Likely too Large for Beam Size ....       0.61 mm
RESPONSE: A suitably sized collimator was used for the data collection.
;
_vrf_PLAT171_b16146_0m_sq        
;
PROBLEM: The CIF-Embedded .res File Contains EADP Records          4 Report
RESPONSE: EADP constraints were used in the refinement of the disordered
phenyl group.
;
_vrf_PLAT176_b16146_0m_sq        
;
PROBLEM: The CIF-Embedded .res File Contains SADI Records          2 Report
RESPONSE: SADI restraints were applied to the disordered phenyl ring
distances. Separately, SADI restraints were applied to the NH bond 
distances, where H-atoms were located in difference map positions.
;
_vrf_PLAT187_b16146_0m_sq        
;
PROBLEM: The CIF-Embedded .res File Contains RIGU Records          1 Report
RESPONSE: A global RIGU restraint, with default standard uncertainties, was
applied.
;
_vrf_PLAT301_b16146_0m_sq        
;
PROBLEM: Main Residue  Disorder ..............(Resd  1)..         21 % Note  
RESPONSE: Acknowledged. Main molecule exhibited some disorder. 
This was modeled for the terminal pheny ring.
;
_vrf_PLAT606_b16146_0m_sq        
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info 
RESPONSE: PLATON Squeeze was used to apply a solvent mask to account for
electrons in the disordered solvent region.
;
_vrf_PLAT720_b16146_0m_sq        
;
PROBLEM: Number of Unusual/Non-Standard Labels ..........          2 Note 
RESPONSE: These are two H-atoms on the disordered phenyl ring. Their 
labels make sense in context, and do not violate shelx rules for
naming atoms.
;
_vrf_PLAT860_b16146_0m_sq        
;
PROBLEM: Number of Least-Squares Restraints .............        240 Note
RESPONSE: SADI and RIGU restraints were applied.
;
_vrf_PLAT869_b16146_0m_sq        
;
PROBLEM: ALERTS Related to the use of SQUEEZE Suppressed           ! Info
RESPONSE: PLATON Squeeze was used to apply a solvent mask to account for
electrons in the disordered solvent region.
;
_vrf_PLAT909_b16146_0m_sq        
;
PROBLEM: Percentage of Observed Data at Theta(Max) Still          70 % Note
RESPONSE: No issues with respect to diffraction strength was observed.
;
_vrf_PLAT933_b16146_0m_sq        
;
PROBLEM: Number of OMIT Records in Embedded .res File ...          3 Note
RESPONSE: Three reflections with error/esd greater than 10 were omitted.
;
_vrf_PLAT978_b16146_0m_sq        
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          1 Note
RESPONSE: This is an indicator of a satisfactory model.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_b16148_0m
_database_code_depnum_ccdc_archive 'CCDC 1560514'
_audit_update_record             
;
2017-07-05 deposited with the CCDC.
2017-08-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H8 N5 O2, 2(C2 H6 O S), H2 O'
_chemical_formula_sum            'C16 H22 N5 O5 S2'
_chemical_formula_weight         428.50
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.953(3)
_cell_length_b                   9.0278(18)
_cell_length_c                   20.734(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.539(9)
_cell_angle_gamma                90
_cell_volume                     1993.3(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9400
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      39.27
_cell_measurement_theta_min      3.18
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.7481
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0548 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.9177.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.559
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.132
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            126417
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         41.184
_diffrn_reflns_theta_min         2.958
_diffrn_ambient_temperature      123.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9784
_reflns_number_total             12861
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.989
_refine_diff_density_min         -1.362
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         12861
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0745P)²+0.6008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O5-H5C \\sim O5-H5D
 with sigma of 0.02
 N4-H4B \\sim N4-H4A \\sim N5-H5A \\sim N5-H5B
 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_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 0.97942(6) 0.16645(7) 0.60904(3) 0.01476(10) Uani 1 1 d . . . . .
O2 O 1.15291(6) -0.07435(7) 0.62157(3) 0.01646(11) Uani 1 1 d . . . . .
N1 N 0.70533(6) 0.20863(7) 0.48164(3) 0.01097(10) Uani 1 1 d . . . . .
N2 N 0.66829(6) 0.47039(7) 0.48316(4) 0.01151(10) Uani 1 1 d . . . . .
N3 N 0.87509(5) 0.37729(7) 0.48811(3) 0.01081(10) Uani 1 1 d . . . . .
N4 N 0.50980(6) 0.30227(8) 0.48077(4) 0.01722(13) Uani 1 1 d D . . . .
H4A H 0.4616(15) 0.3697(17) 0.4857(9) 0.032(4) Uiso 1 1 d D . . . .
H4B H 0.4823(14) 0.2158(14) 0.4771(7) 0.020(3) Uiso 1 1 d D . . . .
N5 N 0.83507(6) 0.62636(7) 0.48190(4) 0.01560(12) Uani 1 1 d D . . . .
H5A H 0.7936(14) 0.7024(15) 0.4842(8) 0.026(4) Uiso 1 1 d D . . . .
H5B H 0.9119(12) 0.6367(19) 0.4875(8) 0.026(4) Uiso 1 1 d D . . . .
C1 C 0.91556(6) 0.11734(7) 0.49365(4) 0.00923(10) Uani 1 1 d . . . . .
C2 C 0.99179(6) 0.08261(8) 0.55541(4) 0.00995(10) Uani 1 1 d . . . . .
C3 C 1.04505(7) 0.11491(9) 0.67025(4) 0.01329(12) Uani 1 1 d . . . . .
C4 C 1.02446(8) 0.18413(10) 0.72650(4) 0.01661(13) Uani 1 1 d . . . . .
H4 H 0.9665 0.2638 0.7225 0.020 Uiso 1 1 calc R . . . .
C5 C 1.08954(9) 0.13598(12) 0.78908(4) 0.02089(16) Uani 1 1 d . . . . .
H5 H 1.0760 0.1833 0.8277 0.025 Uiso 1 1 calc R . . . .
C6 C 1.17391(9) 0.01926(12) 0.79507(4) 0.02258(17) Uani 1 1 d . . . . .
H6 H 1.2180 -0.0131 0.8378 0.027 Uiso 1 1 calc R . . . .
C7 C 1.19404(8) -0.05056(11) 0.73837(4) 0.01919(15) Uani 1 1 d . . . . .
H7 H 1.2515 -0.1307 0.7423 0.023 Uiso 1 1 calc R . . . .
C8 C 1.12978(7) -0.00225(9) 0.67644(4) 0.01407(12) Uani 1 1 d . . . . .
C9 C 1.07594(6) -0.03454(8) 0.56157(4) 0.01026(10) Uani 1 1 d . . . . .
C10 C 0.82549(6) 0.24312(7) 0.48693(3) 0.00880(10) Uani 1 1 d . . . . .
C11 C 0.79063(6) 0.48936(8) 0.48434(4) 0.01022(10) Uani 1 1 d . . . . .
C12 C 0.62993(6) 0.32826(8) 0.48147(4) 0.01082(11) Uani 1 1 d . . . . .
S1 S 0.56078(3) 0.03497(4) 0.64203(2) 0.03223(7) Uani 1 1 d . . . . .
O3 O 0.59102(12) -0.04989(12) 0.70598(5) 0.0439(3) Uani 1 1 d . . . . .
C13 C 0.68388(11) 0.16648(15) 0.64796(6) 0.0296(2) Uani 1 1 d . . . . .
H13A H 0.6926 0.2242 0.6888 0.044 Uiso 1 1 calc GR . . . .
H13B H 0.6641 0.2331 0.6096 0.044 Uiso 1 1 calc GR . . . .
H13C H 0.7628 0.1146 0.6487 0.044 Uiso 1 1 calc GR . . . .
C14 C 0.43869(12) 0.1632(2) 0.64724(7) 0.0482(4) Uani 1 1 d . . . . .
H14A H 0.3617 0.1087 0.6479 0.072 Uiso 1 1 calc GR . . . .
H14B H 0.4232 0.2293 0.6087 0.072 Uiso 1 1 calc GR . . . .
H14C H 0.4644 0.2219 0.6879 0.072 Uiso 1 1 calc GR . . . .
S2 S 0.62651(2) 0.24412(3) 0.82207(2) 0.02212(6) Uani 1 1 d . . . . .
O4 O 0.64663(8) 0.35840(10) 0.87630(4) 0.02857(16) Uani 1 1 d . . . . .
C15 C 0.76090(11) 0.12631(15) 0.83882(6) 0.0313(2) Uani 1 1 d . . . . .
H15A H 0.8347 0.1828 0.8341 0.047 Uiso 1 1 calc GR . . . .
H15B H 0.7471 0.0435 0.8074 0.047 Uiso 1 1 calc GR . . . .
H15C H 0.7747 0.0879 0.8842 0.047 Uiso 1 1 calc GR . . . .
C16 C 0.51497(11) 0.11444(15) 0.83941(6) 0.0305(2) Uani 1 1 d . . . . .
H16A H 0.5465 0.0727 0.8838 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.5023 0.0346 0.8065 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.4350 0.1649 0.8374 0.046 Uiso 1 1 calc GR . . . .
O5 O 0.68486(6) -0.10686(7) 0.50658(4) 0.01886(12) Uani 1 1 d D . . . .
H5C H 0.6763(17) -0.0222(17) 0.4917(9) 0.037(5) Uiso 1 1 d D . . . .
H5D H 0.7270(15) -0.1150(19) 0.5450(7) 0.030(4) Uiso 1 1 d 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 C2 1.3778(9) . ?
O1 C3 1.3844(10) . ?
O2 C8 1.3846(10) . ?
O2 C9 1.3771(10) . ?
N1 C10 1.3317(9) . ?
N1 C12 1.3591(9) . ?
N2 C11 1.3455(10) . ?
N2 C12 1.3481(10) . ?
N3 C10 1.3254(9) . ?
N3 C11 1.3608(9) . ?
N4 H4A 0.828(13) . ?
N4 H4B 0.834(12) . ?
N4 C12 1.3332(10) . ?
N5 H5A 0.831(12) . ?
N5 H5B 0.828(12) . ?
N5 C11 1.3344(10) . ?
C1 C2 1.3910(10) . ?
C1 C9 1.3887(10) 3_756 ?
C1 C10 1.4892(9) . ?
C2 C9 1.3889(10) . ?
C3 C4 1.3874(11) . ?
C3 C8 1.3931(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.3954(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.3878(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.3961(13) . ?
C7 H7 0.9500 . ?
C7 C8 1.3824(12) . ?
C9 C1 1.3888(10) 3_756 ?
S1 O3 1.4998(12) . ?
S1 C13 1.7791(13) . ?
S1 C14 1.7912(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S2 O4 1.5038(9) . ?
S2 C15 1.7831(12) . ?
S2 C16 1.7883(13) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O5 H5C 0.821(15) . ?
O5 H5D 0.826(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 115.28(6) . . ?
C9 O2 C8 115.37(6) . . ?
C10 N1 C12 113.74(6) . . ?
C11 N2 C12 115.13(6) . . ?
C10 N3 C11 114.09(6) . . ?
H4A N4 H4B 118.2(16) . . ?
C12 N4 H4A 121.7(12) . . ?
C12 N4 H4B 120.0(10) . . ?
H5A N5 H5B 116.8(16) . . ?
C11 N5 H5A 123.6(11) . . ?
C11 N5 H5B 117.9(12) . . ?
C2 C1 C10 119.99(6) . . ?
C9 C1 C2 119.74(6) 3_756 . ?
C9 C1 C10 120.28(6) 3_756 . ?
O1 C2 C1 117.90(6) . . ?
O1 C2 C9 122.18(7) . . ?
C9 C2 C1 119.92(6) . . ?
O1 C3 C4 117.87(7) . . ?
O1 C3 C8 122.10(7) . . ?
C4 C3 C8 120.02(7) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.55(8) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.28(8) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.04(8) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.55(8) . . ?
C8 C7 H7 120.2 . . ?
O2 C8 C3 121.82(7) . . ?
C7 C8 O2 117.62(7) . . ?
C7 C8 C3 120.56(7) . . ?
O2 C9 C1 117.34(6) . 3_756 ?
O2 C9 C2 122.32(6) . . ?
C1 C9 C2 120.34(7) 3_756 . ?
N1 C10 C1 116.72(6) . . ?
N3 C10 N1 127.46(6) . . ?
N3 C10 C1 115.81(6) . . ?
N2 C11 N3 124.55(6) . . ?
N5 C11 N2 119.20(6) . . ?
N5 C11 N3 116.24(6) . . ?
N2 C12 N1 124.81(6) . . ?
N4 C12 N1 117.24(7) . . ?
N4 C12 N2 117.94(6) . . ?
O3 S1 C13 105.83(6) . . ?
O3 S1 C14 106.88(7) . . ?
C13 S1 C14 97.40(8) . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 S2 C15 107.09(6) . . ?
O4 S2 C16 106.63(6) . . ?
C15 S2 C16 98.16(7) . . ?
S2 C15 H15A 109.5 . . ?
S2 C15 H15B 109.5 . . ?
S2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S2 C16 H16A 109.5 . . ?
S2 C16 H16B 109.5 . . ?
S2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H5C O5 H5D 115.8(17) . . ?

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
O1 C2 C9 O2 -0.26(11) . . . . ?
O1 C2 C9 C1 179.26(7) . . . 3_756 ?
O1 C3 C4 C5 -179.55(8) . . . . ?
O1 C3 C8 O2 -0.23(13) . . . . ?
O1 C3 C8 C7 179.79(8) . . . . ?
C1 C2 C9 O2 -179.52(7) . . . . ?
C1 C2 C9 C1 0.00(12) . . . 3_756 ?
C2 O1 C3 C4 -172.41(7) . . . . ?
C2 O1 C3 C8 7.76(11) . . . . ?
C2 C1 C10 N1 -102.48(8) . . . . ?
C2 C1 C10 N3 76.38(9) . . . . ?
C3 O1 C2 C1 171.73(7) . . . . ?
C3 O1 C2 C9 -7.54(10) . . . . ?
C3 C4 C5 C6 -0.26(14) . . . . ?
C4 C3 C8 O2 179.94(8) . . . . ?
C4 C3 C8 C7 -0.04(13) . . . . ?
C4 C5 C6 C7 0.01(16) . . . . ?
C5 C6 C7 C8 0.23(15) . . . . ?
C6 C7 C8 O2 179.80(9) . . . . ?
C6 C7 C8 C3 -0.22(14) . . . . ?
C8 O2 C9 C1 -171.71(7) . . . 3_756 ?
C8 O2 C9 C2 7.82(11) . . . . ?
C8 C3 C4 C5 0.28(13) . . . . ?
C9 O2 C8 C3 -7.55(11) . . . . ?
C9 O2 C8 C7 172.44(8) . . . . ?
C9 C1 C2 O1 -179.29(6) 3_756 . . . ?
C9 C1 C2 C9 0.00(11) 3_756 . . . ?
C9 C1 C10 N1 77.66(9) 3_756 . . . ?
C9 C1 C10 N3 -103.49(8) 3_756 . . . ?
C10 N1 C12 N2 3.10(11) . . . . ?
C10 N1 C12 N4 -175.65(7) . . . . ?
C10 N3 C11 N2 3.53(11) . . . . ?
C10 N3 C11 N5 -176.66(7) . . . . ?
C10 C1 C2 O1 0.85(10) . . . . ?
C10 C1 C2 C9 -179.86(6) . . . . ?
C11 N2 C12 N1 0.74(11) . . . . ?
C11 N2 C12 N4 179.48(7) . . . . ?
C11 N3 C10 N1 1.04(11) . . . . ?
C11 N3 C10 C1 -177.67(6) . . . . ?
C12 N1 C10 N3 -4.11(11) . . . . ?
C12 N1 C10 C1 174.59(6) . . . . ?
C12 N2 C11 N3 -4.32(11) . . . . ?
C12 N2 C11 N5 175.88(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_DIFMN02_b16148_0m           
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*0.75
RESPONSE: The largest peak and hole are sensibly associated with the
heaviest atom in the structure. From the shelxl.lst
 Electron density synthesis with coefficients Fo-Fc

 Highest peak    0.99  at  0.0900  0.5163  0.1558  [  0.60 A from S1 ]
 Deepest hole   -1.37  at  0.0330  0.4196  0.1304  [  0.53 A from S1 ]
;
_vrf_DIFMN03_b16148_0m           
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*0.75
RESPONSE: The largest peak and hole are sensibly associated with the
heaviest atom in the structure. From the shelxl.lst
 Electron density synthesis with coefficients Fo-Fc

 Highest peak    0.99  at  0.0900  0.5163  0.1558  [  0.60 A from S1 ]
 Deepest hole   -1.37  at  0.0330  0.4196  0.1304  [  0.53 A from S1 ]
;
_vrf_PLAT098_b16148_0m           
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -1.37 eA-3  
RESPONSE: The largest peak and hole are sensibly associated with the
heaviest atom in the structure. From the shelxl.lst
 Electron density synthesis with coefficients Fo-Fc

 Highest peak    0.99  at  0.0900  0.5163  0.1558  [  0.60 A from S1 ]
 Deepest hole   -1.37  at  0.0330  0.4196  0.1304  [  0.53 A from S1 ]
;
_vrf_PLAT911_b16148_0m           
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report
RESPONSE: These reflections may have been obscured by the beamstop.
;
_vrf_PLAT002_b16148_0m           
;
PROBLEM: 
RESPONSE: N-H and O-H hydrogen atoms were introduced in difference map
positions, and refined isotropically with same distance (SADI) restraints.
;
_vrf_PLAT176_b16148_0m           
;
PROBLEM: 
RESPONSE: N-H and O-H hydrogen atoms were introduced in difference map
positions, and refined isotropically with same distance (SADI) restraints.
;
_vrf_PLAT042_b16148_0m           
;
PROBLEM: 
RESPONSE: Z value of 4 was used (Z value of 2 was expected by checkCIF/PLATON)
;
_vrf_PLAT045_b16148_0m           
;
PROBLEM: 
RESPONSE: Z value of 4 was used (Z value of 2 was expected by checkCIF/PLATON)
;
# end Validation Reply Form
