# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
# 
#######################################################################

data_160419_s4_dqh
_database_code_depnum_ccdc_archive 'CCDC 1532021'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_audit_creation_date             2016-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        DFX-H2O
_chemical_formula_moiety         'C21 H15 N3 O4, H2 O'
_chemical_formula_sum            'C21 H17 N3 O5'
_chemical_formula_weight         391.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   8.9201(2)
_cell_length_b                   29.7303(8)
_cell_length_c                   7.20740(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.790(3)
_cell_angle_gamma                90.00
_cell_volume                     1893.75(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6070
_cell_measurement_theta_min      3.4860
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8581
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -6.00   45.00   0.3000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -19.0000  -60.0000 170

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00    9.00   0.3000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   83.20   0.3000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       16.6856   19.0000  150.0000 314

#__ type_ start__ end____ width___ exp.time_
  4 omega  -87.00  -48.00   0.3000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000   90.0000 130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0065786000
_diffrn_orient_matrix_UB_12      0.0189971000
_diffrn_orient_matrix_UB_13      -0.0579106000
_diffrn_orient_matrix_UB_21      -0.0691282000
_diffrn_orient_matrix_UB_22      0.0085569000
_diffrn_orient_matrix_UB_23      0.0237603000
_diffrn_orient_matrix_UB_31      0.0402239000
_diffrn_orient_matrix_UB_32      0.0116206000
_diffrn_orient_matrix_UB_33      0.0771390000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3107
_reflns_number_total             3848
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3848
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0472P)²+0.3557P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1076
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.80640(16) 0.66452(5) 0.60367(18) 0.0307(3) Uani 1 d . . .
C2 C 0.62356(15) 0.64134(5) 0.73858(18) 0.0315(3) Uani 1 d . . .
C3 C 0.94280(16) 0.68853(5) 0.56476(18) 0.0322(3) Uani 1 d . . .
C4 C 0.93076(17) 0.73325(5) 0.50537(19) 0.0366(3) Uani 1 d . . .
C5 C 1.06112(19) 0.75661(6) 0.4808(2) 0.0454(4) Uani 1 d . . .
H5 H 1.0547 0.7866 0.4439 0.054 Uiso 1 calc . . R
C6 C 1.19970(19) 0.73578(6) 0.5105(2) 0.0496(4) Uani 1 d . . .
H6 H 1.2862 0.7517 0.4921 0.059 Uiso 1 calc . . R
C7 C 1.21206(19) 0.69140(6) 0.5674(2) 0.0487(4) Uani 1 d . . .
H7 H 1.3063 0.6775 0.5864 0.058 Uiso 1 calc . . R
C8 C 1.08385(17) 0.66786(5) 0.5959(2) 0.0398(4) Uani 1 d . . .
H8 H 1.0918 0.6381 0.6360 0.048 Uiso 1 calc . . R
C9 C 0.51692(15) 0.63638(5) 0.87516(19) 0.0335(3) Uani 1 d . . .
C10 C 0.41268(18) 0.60115(6) 0.8619(2) 0.0436(4) Uani 1 d . . .
C11 C 0.3138(2) 0.59654(7) 0.9928(3) 0.0558(5) Uani 1 d . . .
H11 H 0.2443 0.5731 0.9822 0.067 Uiso 1 calc . . R
C12 C 0.3180(2) 0.62653(7) 1.1386(2) 0.0544(5) Uani 1 d . . .
H12 H 0.2518 0.6232 1.2268 0.065 Uiso 1 calc . . R
C13 C 0.4199(2) 0.66158(6) 1.1542(2) 0.0503(4) Uani 1 d . . .
H13 H 0.4226 0.6818 1.2529 0.060 Uiso 1 calc . . R
C14 C 0.51802(18) 0.66655(6) 1.0232(2) 0.0427(4) Uani 1 d . . .
H14 H 0.5860 0.6904 1.0339 0.051 Uiso 1 calc . . R
C15 C 0.77609(16) 0.60639(5) 0.34255(19) 0.0339(3) Uani 1 d . . .
C16 C 0.86280(17) 0.62747(5) 0.2217(2) 0.0380(3) Uani 1 d . . .
H16 H 0.8977 0.6566 0.2455 0.046 Uiso 1 calc . . R
C17 C 0.89642(17) 0.60460(5) 0.0661(2) 0.0371(3) Uani 1 d . . .
H17 H 0.9571 0.6182 -0.0129 0.045 Uiso 1 calc . . R
C18 C 0.84120(17) 0.56172(5) 0.02593(19) 0.0366(3) Uani 1 d . . .
C19 C 0.7527(2) 0.54155(6) 0.1458(2) 0.0496(4) Uani 1 d . . .
H19 H 0.7140 0.5129 0.1191 0.059 Uiso 1 calc . . R
C20 C 0.7212(2) 0.56357(6) 0.3048(2) 0.0478(4) Uani 1 d . . .
H20 H 0.6632 0.5496 0.3860 0.057 Uiso 1 calc . . R
C21 C 0.87749(18) 0.53937(5) -0.1475(2) 0.0405(4) Uani 1 d . . .
N1 N 0.73423(13) 0.67322(4) 0.74844(16) 0.0328(3) Uani 1 d . . .
N2 N 0.74051(13) 0.62890(4) 0.50679(16) 0.0327(3) Uani 1 d . . .
N3 N 0.62348(14) 0.61376(4) 0.59408(16) 0.0360(3) Uani 1 d . . .
O1 O 0.78960(13) 0.75099(4) 0.47490(19) 0.0581(4) Uani 1 d . . .
H1 H 0.7897 0.7732 0.4073 0.087 Uiso 1 calc . . GR
O2 O 0.40297(15) 0.56994(5) 0.72002(19) 0.0682(4) Uani 1 d . . .
H2 H 0.4666 0.5756 0.6512 0.102 Uiso 1 calc . . GR
O3 O 0.95093(14) 0.55735(4) -0.25555(15) 0.0545(3) Uani 1 d . . .
O4 O 0.82272(18) 0.49863(4) -0.17064(18) 0.0684(4) Uani 1 d . . .
H4 H 0.8383 0.4890 -0.2729 0.103 Uiso 1 calc . . GR
O5 O 0.13744(16) 0.54359(6) 0.47342(17) 0.0668(4) Uani 1 d . . .
H5A H 0.2186 0.5499 0.5446 0.100 Uiso 1 d . . G
H5B H 0.0638 0.5434 0.5369 0.100 Uiso 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
C1 C3 1.4700(19) . ?
C1 N1 1.3237(17) . ?
C1 N2 1.3577(18) . ?
C2 C9 1.4661(19) . ?
C2 N1 1.3635(18) . ?
C2 N3 1.3254(17) . ?
C3 C4 1.396(2) . ?
C3 C8 1.391(2) . ?
C4 C5 1.386(2) . ?
C4 O1 1.3554(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(2) . ?
C9 C14 1.393(2) . ?
C10 C11 1.383(2) . ?
C10 O2 1.375(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(2) . ?
C15 C20 1.378(2) . ?
C15 N2 1.4324(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(2) . ?
C18 C19 1.384(2) . ?
C18 C21 1.489(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.381(2) . ?
C20 H20 0.9300 . ?
C21 O3 1.2084(18) . ?
C21 O4 1.308(2) . ?
N2 N3 1.3661(16) . ?
O1 H1 0.8200 . ?
O2 H2 0.8200 . ?
O4 H4 0.8200 . ?
O5 H5A 0.8499 . ?
O5 H5B 0.8501 . ?

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
N1 C1 C3 123.99(12) . . ?
N1 C1 N2 109.57(12) . . ?
N2 C1 C3 126.33(12) . . ?
N1 C2 C9 124.47(12) . . ?
N3 C2 C9 122.29(13) . . ?
N3 C2 N1 113.22(12) . . ?
C4 C3 C1 119.31(13) . . ?
C8 C3 C1 120.58(13) . . ?
C8 C3 C4 120.02(14) . . ?
C5 C4 C3 119.03(14) . . ?
O1 C4 C3 116.83(13) . . ?
O1 C4 C5 124.14(14) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.46(15) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.73(16) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.61(16) . . ?
C8 C7 H7 120.2 . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.13(15) . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C2 121.10(13) . . ?
C14 C9 C2 120.78(13) . . ?
C14 C9 C10 118.12(14) . . ?
C11 C10 C9 120.55(15) . . ?
O2 C10 C9 122.13(14) . . ?
O2 C10 C11 117.32(15) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.23(17) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.17(16) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.85(16) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.07(16) . . ?
C13 C14 H14 119.5 . . ?
C16 C15 N2 120.77(13) . . ?
C20 C15 C16 120.38(14) . . ?
C20 C15 N2 118.84(13) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.23(14) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 120.95(14) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C19 119.07(14) . . ?
C17 C18 C21 118.38(14) . . ?
C19 C18 C21 122.54(14) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.66(15) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 119.67(15) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
O3 C21 C18 122.82(15) . . ?
O3 C21 O4 123.57(15) . . ?
O4 C21 C18 113.60(14) . . ?
C1 N1 C2 104.42(11) . . ?
C1 N2 C15 131.34(12) . . ?
C1 N2 N3 108.95(11) . . ?
N3 N2 C15 119.70(12) . . ?
C2 N3 N2 103.83(11) . . ?
C4 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C21 O4 H4 109.5 . . ?
H5A O5 H5B 109.5 . . ?

_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_160513_s2_dqh
_database_code_depnum_ccdc_archive 'CCDC 1555279'
_audit_update_record             
;
2017-06-10 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_audit_creation_date             2017-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        DFX-DMF
_chemical_formula_moiety         'C21 H15 N3 O4, C3 H7 N O'
_chemical_formula_sum            'C24 H22 N4 O5'
_chemical_formula_weight         446.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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                   8.9013(4)
_cell_length_b                   33.2054(14)
_cell_length_c                   7.7293(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.210(4)
_cell_angle_gamma                90
_cell_volume                     2278.41(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2454
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0610
_cell_measurement_theta_min      3.6600
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10213
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.913
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    0.00   78.00   0.3000    3.7500
omega____ theta____ kappa____ phi______ frames
    -       16.6856   57.0000 -120.0000 260

#__ type_ start__ end____ width___ exp.time_
  2 omega   -4.00   83.00   0.3000    3.7500
omega____ theta____ kappa____ phi______ frames
    -       16.6856   77.0000    0.0000 290

#__ type_ start__ end____ width___ exp.time_
  3 omega   -7.00   35.00   0.3000    3.7500
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -38.0000   90.0000 140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0211606000
_diffrn_orient_matrix_UB_12      -0.0138747000
_diffrn_orient_matrix_UB_13      0.0671851000
_diffrn_orient_matrix_UB_21      -0.0181927000
_diffrn_orient_matrix_UB_22      -0.0162297000
_diffrn_orient_matrix_UB_23      -0.0573351000
_diffrn_orient_matrix_UB_31      0.0749021000
_diffrn_orient_matrix_UB_32      -0.0000106000
_diffrn_orient_matrix_UB_33      -0.0257873000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3429
_reflns_number_total             4661
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0688P)²+0.3401P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1280
_refine_ls_wR_factor_ref         0.1456
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.00426(15) 0.24915(5) 0.1295(2) 0.0728(5) Uani 1 1 d . . . . .
H1 H -0.0052 0.2301 0.1969 0.109 Uiso 1 1 calc GR . . . .
O2 O 0.42878(17) 0.39616(5) -0.1069(2) 0.0749(5) Uani 1 1 d . . . . .
H2 H 0.3552 0.3953 -0.0491 0.112 Uiso 1 1 calc GR . . . .
O3 O -0.14445(18) 0.41135(4) 0.81751(18) 0.0680(4) Uani 1 1 d . . . . .
O4 O -0.1088(3) 0.47042(5) 0.6961(2) 0.0988(7) Uani 1 1 d . . . . .
H4 H -0.1401 0.4788 0.7866 0.148 Uiso 1 1 calc GR . . . .
N1 N 0.05536(15) 0.31590(4) -0.14909(17) 0.0418(3) Uani 1 1 d . . . . .
N2 N 0.05159(15) 0.35478(4) 0.07820(18) 0.0427(3) Uani 1 1 d . . . . .
N3 N 0.17321(16) 0.36727(5) -0.00620(19) 0.0478(4) Uani 1 1 d . . . . .
C1 C -0.01758(18) 0.32428(5) -0.0107(2) 0.0390(4) Uani 1 1 d . . . . .
C2 C 0.17114(18) 0.34287(5) -0.1422(2) 0.0422(4) Uani 1 1 d . . . . .
C3 C -0.15558(18) 0.30380(5) 0.0377(2) 0.0397(4) Uani 1 1 d . . . . .
C4 C -0.1446(2) 0.26484(5) 0.1052(2) 0.0468(4) Uani 1 1 d . . . . .
C5 C -0.2744(2) 0.24492(6) 0.1443(2) 0.0552(5) Uani 1 1 d . . . . .
H5 H -0.2687 0.2188 0.1873 0.066 Uiso 1 1 calc R . . . .
C6 C -0.4111(2) 0.26369(7) 0.1199(3) 0.0587(5) Uani 1 1 d . . . . .
H6 H -0.4977 0.2501 0.1471 0.070 Uiso 1 1 calc R . . . .
C7 C -0.4227(2) 0.30236(7) 0.0558(3) 0.0584(5) Uani 1 1 d . . . . .
H7 H -0.5163 0.3149 0.0408 0.070 Uiso 1 1 calc R . . . .
C8 C -0.2947(2) 0.32239(6) 0.0141(2) 0.0484(4) Uani 1 1 d . . . . .
H8 H -0.3019 0.3484 -0.0299 0.058 Uiso 1 1 calc R . . . .
C9 C 0.28406(19) 0.34553(5) -0.2706(2) 0.0457(4) Uani 1 1 d . . . . .
C10 C 0.4050(2) 0.37200(6) -0.2483(3) 0.0548(5) Uani 1 1 d . . . . .
C11 C 0.5104(2) 0.37388(8) -0.3723(3) 0.0719(6) Uani 1 1 d . . . . .
H11 H 0.5917 0.3914 -0.3567 0.086 Uiso 1 1 calc R . . . .
C12 C 0.4953(3) 0.35016(8) -0.5170(3) 0.0741(7) Uani 1 1 d . . . . .
H12 H 0.5659 0.3518 -0.5996 0.089 Uiso 1 1 calc R . . . .
C13 C 0.3766(2) 0.32383(7) -0.5412(3) 0.0675(6) Uani 1 1 d . . . . .
H13 H 0.3666 0.3078 -0.6400 0.081 Uiso 1 1 calc R . . . .
C14 C 0.2726(2) 0.32133(6) -0.4184(3) 0.0565(5) Uani 1 1 d . . . . .
H14 H 0.1932 0.3032 -0.4342 0.068 Uiso 1 1 calc R . . . .
C15 C 0.01202(19) 0.37458(5) 0.2327(2) 0.0426(4) Uani 1 1 d . . . . .
C16 C 0.0324(2) 0.41555(6) 0.2492(3) 0.0576(5) Uani 1 1 d . . . . .
H16 H 0.0715 0.4303 0.1607 0.069 Uiso 1 1 calc R . . . .
C17 C -0.0063(3) 0.43437(6) 0.3992(3) 0.0625(6) Uani 1 1 d . . . . .
H17 H 0.0071 0.4620 0.4116 0.075 Uiso 1 1 calc R . . . .
C18 C -0.0649(2) 0.41246(6) 0.5317(2) 0.0476(4) Uani 1 1 d . . . . .
C19 C -0.0849(2) 0.37134(6) 0.5115(2) 0.0474(4) Uani 1 1 d . . . . .
H19 H -0.1253 0.3565 0.5990 0.057 Uiso 1 1 calc R . . . .
C20 C -0.0457(2) 0.35225(6) 0.3638(2) 0.0480(4) Uani 1 1 d . . . . .
H20 H -0.0577 0.3245 0.3520 0.058 Uiso 1 1 calc R . . . .
C21 C -0.1090(2) 0.43094(6) 0.6968(2) 0.0538(5) Uani 1 1 d . . . . .
O5 O -0.2138(3) 0.49962(6) -0.0256(3) 0.1146(8) Uani 1 1 d . . . . .
N4 N -0.3490(3) 0.48183(7) 0.1978(3) 0.0865(6) Uani 1 1 d . . . . .
C22 C -0.2922(4) 0.47471(10) 0.0494(4) 0.0958(9) Uani 1 1 d . . . . .
H22 H -0.3110 0.4498 -0.0031 0.115 Uiso 1 1 calc R . . . .
C24 C -0.4405(5) 0.45125(13) 0.2763(5) 0.1346(13) Uani 1 1 d . . . . .
H24A H -0.5425 0.4606 0.2772 0.202 Uiso 1 1 calc GR . . . .
H24B H -0.4007 0.4462 0.3932 0.202 Uiso 1 1 calc GR . . . .
H24C H -0.4384 0.4268 0.2103 0.202 Uiso 1 1 calc GR . . . .
C25 C -0.3247(5) 0.51800(11) 0.2940(5) 0.1437(15) Uani 1 1 d . . . . .
H25A H -0.2885 0.5116 0.4108 0.216 Uiso 1 1 calc GR . . . .
H25B H -0.4177 0.5326 0.2951 0.216 Uiso 1 1 calc GR . . . .
H25C H -0.2515 0.5342 0.2411 0.216 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 H1 0.8200 . ?
O1 C4 1.354(2) . ?
O2 H2 0.8200 . ?
O2 C10 1.359(2) . ?
O3 C21 1.199(2) . ?
O4 H4 0.8200 . ?
O4 C21 1.311(2) . ?
N1 C1 1.321(2) . ?
N1 C2 1.363(2) . ?
N2 N3 1.3687(18) . ?
N2 C1 1.347(2) . ?
N2 C15 1.430(2) . ?
N3 C2 1.326(2) . ?
C1 C3 1.476(2) . ?
C2 C9 1.466(2) . ?
C3 C4 1.395(2) . ?
C3 C8 1.384(2) . ?
C4 C5 1.384(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.368(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(3) . ?
C9 C14 1.394(3) . ?
C10 C11 1.391(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 C20 1.385(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(2) . ?
C18 C19 1.384(3) . ?
C18 C21 1.494(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(2) . ?
C20 H20 0.9300 . ?
O5 C22 1.251(3) . ?
N4 C22 1.309(3) . ?
N4 C24 1.461(4) . ?
N4 C25 1.421(4) . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C21 O4 H4 109.5 . . ?
C1 N1 C2 104.18(14) . . ?
N3 N2 C15 120.71(14) . . ?
C1 N2 N3 109.43(13) . . ?
C1 N2 C15 129.81(14) . . ?
C2 N3 N2 103.13(14) . . ?
N1 C1 N2 109.75(14) . . ?
N1 C1 C3 125.13(15) . . ?
N2 C1 C3 125.10(14) . . ?
N1 C2 C9 124.53(15) . . ?
N3 C2 N1 113.49(14) . . ?
N3 C2 C9 121.98(16) . . ?
C4 C3 C1 119.01(15) . . ?
C8 C3 C1 120.96(15) . . ?
C8 C3 C4 120.02(15) . . ?
O1 C4 C3 116.58(15) . . ?
O1 C4 C5 124.22(17) . . ?
C5 C4 C3 119.20(17) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.04(18) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.11(18) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.53(19) . . ?
C8 C7 H7 120.2 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.08(18) . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C2 121.12(17) . . ?
C10 C9 C14 118.39(16) . . ?
C14 C9 C2 120.49(16) . . ?
O2 C10 C9 123.10(16) . . ?
O2 C10 C11 117.04(18) . . ?
C9 C10 C11 119.84(19) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.45(19) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.19(19) . . ?
C13 C14 H14 119.4 . . ?
C16 C15 N2 119.53(15) . . ?
C16 C15 C20 120.97(16) . . ?
C20 C15 N2 119.51(16) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.00(17) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.77(18) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C21 123.42(17) . . ?
C19 C18 C17 119.07(17) . . ?
C19 C18 C21 117.51(16) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.71(17) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 H20 120.3 . . ?
C19 C20 C15 119.47(17) . . ?
C19 C20 H20 120.3 . . ?
O3 C21 O4 123.12(18) . . ?
O3 C21 C18 122.86(18) . . ?
O4 C21 C18 114.01(17) . . ?
C22 N4 C24 120.1(3) . . ?
C22 N4 C25 123.9(3) . . ?
C25 N4 C24 116.0(2) . . ?
O5 C22 N4 123.4(3) . . ?
O5 C22 H22 118.3 . . ?
N4 C22 H22 118.3 . . ?
N4 C24 H24A 109.5 . . ?
N4 C24 H24B 109.5 . . ?
N4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C25 H25A 109.5 . . ?
N4 C25 H25B 109.5 . . ?
N4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_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_161128_s2_dqh
_database_code_depnum_ccdc_archive 'CCDC 1527600'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT602_161128_s2_dqh       
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info
RESPONSE: In the process of structure solution?the solvent molecules in the lattice were deducted, because there is no strong intermolecular force between the solvent molecules and the co-crystal molecule, and their position cannot be determined.
;
# Added during the CSD deposition process: Monday 12 June 2017 07:49 AM
# end Validation Reply Form

_audit_creation_date             2017-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        DFX-2INA
_chemical_formula_moiety         'C21 H15 N3 O4, 2(C6 H6 N2 O)'
_chemical_formula_sum            'C33 H27 N7 O6'
_chemical_formula_weight         617.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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           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                   21.5782(6)
_cell_length_b                   8.4837(2)
_cell_length_c                   37.8874(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.377(3)
_cell_angle_gamma                90
_cell_volume                     6799.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6191
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8440
_cell_measurement_theta_min      3.4960
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2576
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            24099
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.883
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   52.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336   57.0000  -90.0000 360

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   79.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3523   57.0000 -120.0000 385

#__ type_ start__ end____ width___ exp.time_
  3 omega   -2.00   23.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000 -150.0000 125

#__ type_ start__ end____ width___ exp.time_
  4 omega   25.00   50.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3523 -150.0000 -104.0000 125

#__ type_ start__ end____ width___ exp.time_
  5 omega    7.00   32.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3523 -122.0000   57.0000 125

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   19.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000   60.0000 215

#__ type_ start__ end____ width___ exp.time_
  7 omega  -65.00  -40.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336 -178.0000  120.0000 125

#__ type_ start__ end____ width___ exp.time_
  8 omega  -55.00  -30.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  122.0000  138.0000 125

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   72.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       17.3523  178.0000  150.0000 180

#__ type_ start__ end____ width___ exp.time_
 10 omega  -72.00  -47.00   0.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  150.0000  -59.0000 125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0018591000
_diffrn_orient_matrix_UB_12      -0.0827772000
_diffrn_orient_matrix_UB_13      -0.0026353000
_diffrn_orient_matrix_UB_21      0.0027226000
_diffrn_orient_matrix_UB_22      -0.0111930000
_diffrn_orient_matrix_UB_23      0.0187881000
_diffrn_orient_matrix_UB_31      -0.0333800000
_diffrn_orient_matrix_UB_32      0.0037400000
_diffrn_orient_matrix_UB_33      -0.0021055000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5564
_reflns_number_total             6852
_reflns_odcompleteness_completeness 98.07
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.200
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6852
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.030
_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)+(0.0602P)²+2.8861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1281
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26),
  C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O4(H4)
;
_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 0.65749(5) -0.02956(14) 0.48846(3) 0.0442(3) Uani 1 1 d . . . . .
H1 H 0.6871 -0.0674 0.5029 0.066 Uiso 1 1 calc GR . . . .
O2 O 0.35488(6) -0.0737(2) 0.40742(4) 0.0704(4) Uani 1 1 d . . . . .
H2 H 0.3826 -0.0251 0.4211 0.106 Uiso 1 1 calc GR . . . .
O3 O 0.45984(6) 0.47140(17) 0.58754(3) 0.0580(4) Uani 1 1 d . . . . .
O4 O 0.55797(6) 0.55630(16) 0.58797(3) 0.0527(3) Uani 1 1 d . . . . .
H4 H 0.5526 0.6033 0.6060 0.079 Uiso 1 1 calc GR . . . .
O5 O 0.59544(7) 0.9207(3) 0.77507(4) 0.1002(7) Uani 1 1 d . . . . .
N1 N 0.54769(5) 0.00194(15) 0.40197(3) 0.0336(3) Uani 1 1 d . . . . .
N2 N 0.52272(5) 0.11988(14) 0.44889(3) 0.0282(3) Uani 1 1 d . . . . .
N3 N 0.46837(5) 0.04812(14) 0.43125(3) 0.0315(3) Uani 1 1 d . . . . .
N4 N 0.56620(8) 0.7159(2) 0.64981(4) 0.0553(4) Uani 1 1 d . . . . .
N5 N 0.69041(10) 0.9718(4) 0.76237(6) 0.0997(9) Uani 1 1 d . . . . .
H5A H 0.7183(14) 0.978(4) 0.7461(8) 0.120 Uiso 1 1 d R . . . .
H5B H 0.7050(12) 1.009(3) 0.7848(8) 0.097(8) Uiso 1 1 d . . . . .
C1 C 0.56967(6) 0.08945(17) 0.43062(4) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.48560(6) -0.02177(17) 0.40360(4) 0.0304(3) Uani 1 1 d . . . . .
C3 C 0.63625(6) 0.14149(17) 0.43889(4) 0.0302(3) Uani 1 1 d . . . . .
C4 C 0.67993(7) 0.07236(17) 0.46672(4) 0.0312(3) Uani 1 1 d . . . . .
C5 C 0.74332(7) 0.11139(19) 0.47076(4) 0.0365(3) Uani 1 1 d . . . . .
H5 H 0.7728 0.0651 0.4891 0.044 Uiso 1 1 calc R . . . .
C6 C 0.76306(7) 0.2179(2) 0.44796(4) 0.0405(4) Uani 1 1 d . . . . .
H6 H 0.8057 0.2430 0.4510 0.049 Uiso 1 1 calc R . . . .
C7 C 0.72019(7) 0.2878(2) 0.42062(4) 0.0409(4) Uani 1 1 d . . . . .
H7 H 0.7338 0.3605 0.4054 0.049 Uiso 1 1 calc R . . . .
C8 C 0.65690(7) 0.24911(19) 0.41602(4) 0.0368(3) Uani 1 1 d . . . . .
H8 H 0.6279 0.2953 0.3975 0.044 Uiso 1 1 calc R . . . .
C9 C 0.44239(7) -0.11943(19) 0.37781(4) 0.0359(3) Uani 1 1 d . . . . .
C10 C 0.38006(7) -0.1437(2) 0.38139(5) 0.0443(4) Uani 1 1 d . . . . .
C11 C 0.34130(9) -0.2433(3) 0.35765(6) 0.0614(5) Uani 1 1 d . . . . .
H11 H 0.3000 -0.2613 0.3604 0.074 Uiso 1 1 calc R . . . .
C12 C 0.36323(10) -0.3146(3) 0.33041(6) 0.0709(6) Uani 1 1 d . . . . .
H12 H 0.3365 -0.3794 0.3144 0.085 Uiso 1 1 calc R . . . .
C13 C 0.42476(10) -0.2917(3) 0.32632(6) 0.0752(7) Uani 1 1 d . . . . .
H13 H 0.4397 -0.3410 0.3077 0.090 Uiso 1 1 calc R . . . .
C14 C 0.46378(9) -0.1951(3) 0.35010(5) 0.0558(5) Uani 1 1 d . . . . .
H14 H 0.5054 -0.1803 0.3475 0.067 Uiso 1 1 calc R . . . .
C15 C 0.52148(6) 0.20635(16) 0.48107(4) 0.0281(3) Uani 1 1 d . . . . .
C16 C 0.57018(7) 0.30730(18) 0.49595(4) 0.0350(3) Uani 1 1 d . . . . .
H16 H 0.6051 0.3194 0.4852 0.042 Uiso 1 1 calc R . . . .
C17 C 0.56643(7) 0.38962(18) 0.52682(4) 0.0361(3) Uani 1 1 d . . . . .
H17 H 0.5996 0.4554 0.5371 0.043 Uiso 1 1 calc R . . . .
C18 C 0.51435(7) 0.37666(17) 0.54293(4) 0.0322(3) Uani 1 1 d . . . . .
C19 C 0.46597(7) 0.27419(18) 0.52768(4) 0.0342(3) Uani 1 1 d . . . . .
H19 H 0.4308 0.2631 0.5383 0.041 Uiso 1 1 calc R . . . .
C20 C 0.46937(7) 0.18900(17) 0.49715(4) 0.0320(3) Uani 1 1 d . . . . .
H20 H 0.4369 0.1202 0.4874 0.038 Uiso 1 1 calc R . . . .
C21 C 0.50748(7) 0.47081(19) 0.57511(4) 0.0381(4) Uani 1 1 d . . . . .
C22 C 0.62666(10) 0.7456(3) 0.66178(6) 0.0782(7) Uani 1 1 d . . . . .
H22 H 0.6548 0.7202 0.6470 0.094 Uiso 1 1 calc R . . . .
C23 C 0.65072(10) 0.8118(3) 0.69476(6) 0.0783(8) Uani 1 1 d . . . . .
H23 H 0.6939 0.8300 0.7019 0.094 Uiso 1 1 calc R . . . .
C24 C 0.60999(9) 0.8503(3) 0.71687(5) 0.0545(5) Uani 1 1 d . . . . .
C25 C 0.54670(9) 0.8224(3) 0.70446(5) 0.0601(5) Uani 1 1 d . . . . .
H25 H 0.5174 0.8486 0.7185 0.072 Uiso 1 1 calc R . . . .
C26 C 0.52705(9) 0.7553(3) 0.67114(5) 0.0580(5) Uani 1 1 d . . . . .
H26 H 0.4841 0.7368 0.6632 0.070 Uiso 1 1 calc R . . . .
C27 C 0.63183(10) 0.9184(3) 0.75392(5) 0.0708(7) Uani 1 1 d . . . . .
H7B H 0.1092(10) 0.463(2) 0.3641(6) 0.063(6) Uiso 1 1 d . . . . .
O6 O 0.23062(6) 0.4271(2) 0.33618(4) 0.0770(5) Uani 1 1 d . . . . .
N6 N 0.26474(7) 0.17984(17) 0.45690(4) 0.0461(3) Uani 1 1 d . . . . .
N7 N 0.13339(7) 0.4562(2) 0.34842(4) 0.0506(4) Uani 1 1 d . . . . .
H7A H 0.1187(11) 0.498(3) 0.3262(7) 0.082(7) Uiso 1 1 d . . . . .
C28 C 0.21596(7) 0.3358(2) 0.39263(4) 0.0381(4) Uani 1 1 d . . . . .
C29 C 0.27940(8) 0.3475(2) 0.40856(4) 0.0421(4) Uani 1 1 d . . . . .
H29 H 0.3067 0.4080 0.3980 0.051 Uiso 1 1 calc R . . . .
C30 C 0.30123(8) 0.2684(2) 0.44016(4) 0.0451(4) Uani 1 1 d . . . . .
H30 H 0.3439 0.2769 0.4505 0.054 Uiso 1 1 calc R . . . .
C31 C 0.20363(8) 0.1712(2) 0.44159(5) 0.0468(4) Uani 1 1 d . . . . .
H31 H 0.1773 0.1112 0.4530 0.056 Uiso 1 1 calc R . . . .
C32 C 0.17738(8) 0.2457(2) 0.41004(4) 0.0430(4) Uani 1 1 d . . . . .
H32 H 0.1344 0.2359 0.4004 0.052 Uiso 1 1 calc R . . . .
C33 C 0.19348(8) 0.4125(2) 0.35679(4) 0.0471(4) Uani 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 H1 0.8200 . ?
O1 C4 1.3484(18) . ?
O2 H2 0.8200 . ?
O2 C10 1.354(2) . ?
O3 C21 1.2122(19) . ?
O4 H4 0.8200 . ?
O4 C21 1.3194(19) . ?
O5 C27 1.227(2) . ?
N1 C1 1.3232(18) . ?
N1 C2 1.3683(18) . ?
N2 N3 1.3725(15) . ?
N2 C1 1.3596(17) . ?
N2 C15 1.4278(18) . ?
N3 C2 1.3194(18) . ?
N4 C22 1.318(3) . ?
N4 C26 1.322(2) . ?
N5 H5A 0.94(3) . ?
N5 H5B 0.90(3) . ?
N5 C27 1.321(3) . ?
C1 C3 1.4763(18) . ?
C2 C9 1.467(2) . ?
C3 C4 1.397(2) . ?
C3 C8 1.391(2) . ?
C4 C5 1.3862(19) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.394(2) . ?
C9 C14 1.385(2) . ?
C10 C11 1.387(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.359(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(2) . ?
C15 C20 1.3884(19) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(2) . ?
C18 C19 1.393(2) . ?
C18 C21 1.489(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(2) . ?
C20 H20 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.375(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.368(3) . ?
C24 C25 1.374(2) . ?
C24 C27 1.505(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.373(3) . ?
C26 H26 0.9300 . ?
O6 C33 1.230(2) . ?
N6 C30 1.335(2) . ?
N6 C31 1.334(2) . ?
N7 H7B 0.87(2) . ?
N7 H7A 0.91(3) . ?
N7 C33 1.326(2) . ?
C28 C29 1.386(2) . ?
C28 C32 1.389(2) . ?
C28 C33 1.498(2) . ?
C29 H29 0.9300 . ?
C29 C30 1.372(2) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.372(2) . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C21 O4 H4 109.5 . . ?
C1 N1 C2 103.95(11) . . ?
N3 N2 C15 119.05(11) . . ?
C1 N2 N3 108.60(11) . . ?
C1 N2 C15 132.35(11) . . ?
C2 N3 N2 103.79(11) . . ?
C22 N4 C26 116.73(16) . . ?
H5A N5 H5B 116(2) . . ?
C27 N5 H5A 124.4(19) . . ?
C27 N5 H5B 119.2(17) . . ?
N1 C1 N2 109.98(12) . . ?
N1 C1 C3 121.20(12) . . ?
N2 C1 C3 128.81(12) . . ?
N1 C2 C9 123.53(13) . . ?
N3 C2 N1 113.68(12) . . ?
N3 C2 C9 122.77(13) . . ?
C4 C3 C1 121.20(13) . . ?
C8 C3 C1 118.81(13) . . ?
C8 C3 C4 119.62(13) . . ?
O1 C4 C3 117.40(12) . . ?
O1 C4 C5 123.44(13) . . ?
C5 C4 C3 119.16(13) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.60(14) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.64(14) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.48(14) . . ?
C8 C7 H7 120.3 . . ?
C3 C8 H8 119.8 . . ?
C7 C8 C3 120.49(14) . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C2 121.17(14) . . ?
C14 C9 C2 120.26(14) . . ?
C14 C9 C10 118.52(14) . . ?
O2 C10 C9 122.67(14) . . ?
O2 C10 C11 117.53(15) . . ?
C11 C10 C9 119.80(16) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.50(18) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.60(17) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.24(19) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.33(17) . . ?
C13 C14 H14 119.3 . . ?
C16 C15 N2 121.63(12) . . ?
C16 C15 C20 120.11(13) . . ?
C20 C15 N2 118.26(12) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.44(13) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.49(13) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C19 118.25(13) . . ?
C17 C18 C21 122.60(14) . . ?
C19 C18 C21 119.13(13) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.05(13) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 H20 120.2 . . ?
C19 C20 C15 119.64(13) . . ?
C19 C20 H20 120.2 . . ?
O3 C21 O4 123.78(15) . . ?
O3 C21 C18 123.31(15) . . ?
O4 C21 C18 112.88(13) . . ?
N4 C22 H22 117.9 . . ?
N4 C22 C23 124.15(19) . . ?
C23 C22 H22 117.9 . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.75(19) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 C25 117.65(17) . . ?
C23 C24 C27 122.82(18) . . ?
C25 C24 C27 119.52(16) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 C24 119.46(17) . . ?
C26 C25 H25 120.3 . . ?
N4 C26 C25 123.23(18) . . ?
N4 C26 H26 118.4 . . ?
C25 C26 H26 118.4 . . ?
O5 C27 N5 122.75(19) . . ?
O5 C27 C24 119.47(18) . . ?
N5 C27 C24 117.78(17) . . ?
C31 N6 C30 116.70(14) . . ?
H7B N7 H7A 118(2) . . ?
C33 N7 H7B 123.0(14) . . ?
C33 N7 H7A 118.5(15) . . ?
C29 C28 C32 117.73(15) . . ?
C29 C28 C33 118.63(15) . . ?
C32 C28 C33 123.53(15) . . ?
C28 C29 H29 120.5 . . ?
C30 C29 C28 118.99(16) . . ?
C30 C29 H29 120.5 . . ?
N6 C30 C29 123.79(16) . . ?
N6 C30 H30 118.1 . . ?
C29 C30 H30 118.1 . . ?
N6 C31 H31 118.1 . . ?
N6 C31 C32 123.82(16) . . ?
C32 C31 H31 118.1 . . ?
C28 C32 H32 120.5 . . ?
C31 C32 C28 118.96(15) . . ?
C31 C32 H32 120.5 . . ?
O6 C33 N7 123.28(16) . . ?
O6 C33 C28 118.97(15) . . ?
N7 C33 C28 117.71(15) . . ?

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 C4 C5 C6 -179.12(14) . . . . ?
O2 C10 C11 C12 178.6(2) . . . . ?
N1 C1 C3 C4 -105.41(16) . . . . ?
N1 C1 C3 C8 67.62(19) . . . . ?
N1 C2 C9 C10 177.92(15) . . . . ?
N1 C2 C9 C14 0.7(2) . . . . ?
N2 N3 C2 N1 -0.77(16) . . . . ?
N2 N3 C2 C9 177.47(13) . . . . ?
N2 C1 C3 C4 75.2(2) . . . . ?
N2 C1 C3 C8 -111.73(17) . . . . ?
N2 C15 C16 C17 179.21(13) . . . . ?
N2 C15 C20 C19 -178.21(12) . . . . ?
N3 N2 C1 N1 0.27(16) . . . . ?
N3 N2 C1 C3 179.68(13) . . . . ?
N3 N2 C15 C16 -166.52(13) . . . . ?
N3 N2 C15 C20 12.53(18) . . . . ?
N3 C2 C9 C10 -0.1(2) . . . . ?
N3 C2 C9 C14 -177.41(16) . . . . ?
N4 C22 C23 C24 -0.1(4) . . . . ?
C1 N1 C2 N3 0.94(16) . . . . ?
C1 N1 C2 C9 -177.28(14) . . . . ?
C1 N2 N3 C2 0.30(15) . . . . ?
C1 N2 C15 C16 14.2(2) . . . . ?
C1 N2 C15 C20 -166.73(14) . . . . ?
C1 C3 C4 O1 -7.9(2) . . . . ?
C1 C3 C4 C5 172.32(13) . . . . ?
C1 C3 C8 C7 -173.07(14) . . . . ?
C2 N1 C1 N2 -0.70(15) . . . . ?
C2 N1 C1 C3 179.84(13) . . . . ?
C2 C9 C10 O2 3.3(3) . . . . ?
C2 C9 C10 C11 -176.68(17) . . . . ?
C2 C9 C14 C13 177.7(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C3 C8 C7 0.1(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 -0.6(2) . . . . ?
C6 C7 C8 C3 0.5(2) . . . . ?
C8 C3 C4 O1 179.11(14) . . . . ?
C8 C3 C4 C5 -0.7(2) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C9 C14 C13 0.4(3) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C9 -0.6(4) . . . . ?
C14 C9 C10 O2 -179.39(18) . . . . ?
C14 C9 C10 C11 0.6(3) . . . . ?
C15 N2 N3 C2 -179.13(12) . . . . ?
C15 N2 C1 N1 179.60(13) . . . . ?
C15 N2 C1 C3 -1.0(2) . . . . ?
C15 C16 C17 C18 -1.5(2) . . . . ?
C16 C15 C20 C19 0.9(2) . . . . ?
C16 C17 C18 C19 1.7(2) . . . . ?
C16 C17 C18 C21 -176.57(14) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
C17 C18 C21 O3 173.12(16) . . . . ?
C17 C18 C21 O4 -5.2(2) . . . . ?
C18 C19 C20 C15 -0.6(2) . . . . ?
C19 C18 C21 O3 -5.2(2) . . . . ?
C19 C18 C21 O4 176.54(14) . . . . ?
C20 C15 C16 C17 0.2(2) . . . . ?
C21 C18 C19 C20 177.70(13) . . . . ?
C22 N4 C26 C25 -0.8(3) . . . . ?
C22 C23 C24 C25 -0.9(4) . . . . ?
C22 C23 C24 C27 178.0(3) . . . . ?
C23 C24 C25 C26 1.1(3) . . . . ?
C23 C24 C27 O5 -165.3(3) . . . . ?
C23 C24 C27 N5 13.9(4) . . . . ?
C24 C25 C26 N4 -0.3(4) . . . . ?
C25 C24 C27 O5 13.6(4) . . . . ?
C25 C24 C27 N5 -167.3(3) . . . . ?
C26 N4 C22 C23 1.0(4) . . . . ?
C27 C24 C25 C26 -177.8(2) . . . . ?
N6 C31 C32 C28 0.0(3) . . . . ?
C28 C29 C30 N6 -0.2(3) . . . . ?
C29 C28 C32 C31 -0.9(2) . . . . ?
C29 C28 C33 O6 28.7(3) . . . . ?
C29 C28 C33 N7 -153.69(17) . . . . ?
C30 N6 C31 C32 0.8(3) . . . . ?
C31 N6 C30 C29 -0.7(3) . . . . ?
C32 C28 C29 C30 1.0(2) . . . . ?
C32 C28 C33 O6 -147.57(19) . . . . ?
C32 C28 C33 N7 30.1(3) . . . . ?
C33 C28 C29 C30 -175.47(16) . . . . ?
C33 C28 C32 C31 175.38(16) . . . . ?

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

data_161206_s3_dqh
_database_code_depnum_ccdc_archive 'CCDC 1527596'
_audit_update_record             
;
2017-06-12 deposited with the CCDC.
2017-09-05 downloaded from the CCDC.
;
_audit_creation_date             2017-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        DFX-INA
_chemical_formula_moiety         'C21 H15 N3 O4, C6 H6 N2 O'
_chemical_formula_sum            'C27 H21 N5 O5'
_chemical_formula_weight         495.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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                   9.3205(3)
_cell_length_b                   36.1503(10)
_cell_length_c                   7.1171(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.206(3)
_cell_angle_gamma                90
_cell_volume                     2360.06(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5110
_cell_measurement_theta_min      3.1750
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            20181
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.962
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -28.00   54.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106   44.0000  106.0000 164

#__ type_ start__ end____ width___ exp.time_
  2 omega  -83.00    1.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -44.0000  -43.0000 168

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   -8.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       16.6856  -44.0000  -43.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega  -76.00  -35.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -79.00  -35.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega  -64.00  -38.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106    0.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  7 omega  -27.00   -2.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106    0.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega   29.00   54.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106    0.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega  -25.00   23.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -120.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0529269000
_diffrn_orient_matrix_UB_12      -0.0093059000
_diffrn_orient_matrix_UB_13      0.0429456000
_diffrn_orient_matrix_UB_21      0.0552382000
_diffrn_orient_matrix_UB_22      -0.0056185000
_diffrn_orient_matrix_UB_23      0.0764391000
_diffrn_orient_matrix_UB_31      -0.0111752000
_diffrn_orient_matrix_UB_32      0.0163302000
_diffrn_orient_matrix_UB_33      0.0507087000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3876
_reflns_number_total             4815
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4815
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      1.085
_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)+(0.0482P)²+0.6851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1297
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47984(17) 0.25250(4) 0.6637(3) 0.0663(5) Uani 1 1 d . . . . .
H1 H 0.4829 0.2326 0.6091 0.099 Uiso 1 1 calc GR . . . .
O2 O 0.0954(2) 0.39343(6) 0.9255(3) 0.0836(6) Uani 1 1 d . . . . .
H2 H 0.1600 0.3910 0.8618 0.125 Uiso 1 1 calc GR . . . .
O3 O 0.45221(19) 0.45338(5) -0.0201(3) 0.0763(5) Uani 1 1 d . . . . .
O4 O 0.63956(18) 0.41588(5) -0.0134(2) 0.0670(5) Uani 1 1 d . . . . .
H4 H 0.6548 0.4291 -0.1013 0.100 Uiso 1 1 calc GR . . . .
N1 N 0.43010(17) 0.31337(4) 0.9581(2) 0.0400(4) Uani 1 1 d . . . . .
N2 N 0.42634(17) 0.35082(4) 0.7151(2) 0.0389(4) Uani 1 1 d . . . . .
N3 N 0.31262(17) 0.36137(4) 0.8013(2) 0.0422(4) Uani 1 1 d . . . . .
C1 C 0.4957(2) 0.32194(5) 0.8136(3) 0.0362(4) Uani 1 1 d . . . . .
C2 C 0.3190(2) 0.33821(5) 0.9456(3) 0.0388(4) Uani 1 1 d . . . . .
C3 C 0.6278(2) 0.30284(5) 0.7762(3) 0.0378(4) Uani 1 1 d . . . . .
C4 C 0.6155(2) 0.26686(5) 0.7064(3) 0.0440(5) Uani 1 1 d . . . . .
C5 C 0.7402(3) 0.24787(6) 0.6845(3) 0.0550(6) Uani 1 1 d . . . . .
H5 H 0.7336 0.2235 0.6414 0.066 Uiso 1 1 calc R . . . .
C6 C 0.8736(3) 0.26481(7) 0.7262(3) 0.0638(7) Uani 1 1 d . . . . .
H6 H 0.9567 0.2519 0.7091 0.077 Uiso 1 1 calc R . . . .
C7 C 0.8865(2) 0.30067(7) 0.7931(3) 0.0616(6) Uani 1 1 d . . . . .
H7 H 0.9774 0.3120 0.8199 0.074 Uiso 1 1 calc R . . . .
C8 C 0.7633(2) 0.31940(6) 0.8198(3) 0.0485(5) Uani 1 1 d . . . . .
H8 H 0.7712 0.3434 0.8675 0.058 Uiso 1 1 calc R . . . .
C9 C 0.2169(2) 0.34008(5) 1.0806(3) 0.0416(4) Uani 1 1 d . . . . .
C10 C 0.1114(2) 0.36757(6) 1.0647(3) 0.0535(5) Uani 1 1 d . . . . .
C11 C 0.0145(3) 0.36896(8) 1.1918(4) 0.0675(7) Uani 1 1 d . . . . .
H11 H -0.0569 0.3872 1.1788 0.081 Uiso 1 1 calc R . . . .
C12 C 0.0237(3) 0.34361(8) 1.3362(4) 0.0713(7) Uani 1 1 d . . . . .
H12 H -0.0418 0.3446 1.4206 0.086 Uiso 1 1 calc R . . . .
C13 C 0.1300(3) 0.31641(7) 1.3572(4) 0.0654(7) Uani 1 1 d . . . . .
H13 H 0.1372 0.2995 1.4569 0.078 Uiso 1 1 calc R . . . .
C14 C 0.2250(2) 0.31452(6) 1.2299(3) 0.0539(5) Uani 1 1 d . . . . .
H14 H 0.2955 0.2960 1.2432 0.065 Uiso 1 1 calc R . . . .
C15 C 0.4522(2) 0.36986(5) 0.5475(3) 0.0381(4) Uani 1 1 d . . . . .
C16 C 0.5539(2) 0.35708(6) 0.4441(3) 0.0520(5) Uani 1 1 d . . . . .
H16 H 0.6055 0.3355 0.4808 0.062 Uiso 1 1 calc R . . . .
C17 C 0.5789(2) 0.37644(6) 0.2861(3) 0.0481(5) Uani 1 1 d . . . . .
H17 H 0.6506 0.3683 0.2201 0.058 Uiso 1 1 calc R . . . .
C18 C 0.4992(2) 0.40773(5) 0.2244(3) 0.0405(4) Uani 1 1 d . . . . .
C19 C 0.3928(2) 0.41909(5) 0.3234(3) 0.0504(5) Uani 1 1 d . . . . .
H19 H 0.3354 0.4395 0.2802 0.060 Uiso 1 1 calc R . . . .
C20 C 0.3699(2) 0.40067(5) 0.4863(3) 0.0482(5) Uani 1 1 d . . . . .
H20 H 0.2995 0.4090 0.5538 0.058 Uiso 1 1 calc R . . . .
C21 C 0.5266(2) 0.42815(6) 0.0516(3) 0.0473(5) Uani 1 1 d . . . . .
O5 O -0.02293(17) 0.52822(5) 0.7920(2) 0.0680(5) Uani 1 1 d . . . . .
N4 N 0.2792(2) 0.55149(5) 0.2994(3) 0.0537(5) Uani 1 1 d . . . . .
N5 N 0.1652(2) 0.49066(5) 0.8975(3) 0.0641(5) Uani 1 1 d . . . . .
H5A H 0.1270 0.4831 0.9920 0.077 Uiso 1 1 calc R . . . .
H5B H 0.2485 0.4822 0.8814 0.077 Uiso 1 1 calc R . . . .
C22 C 0.1687(3) 0.56842(7) 0.3548(4) 0.0664(7) Uani 1 1 d . . . . .
H22 H 0.1297 0.5891 0.2868 0.080 Uiso 1 1 calc R . . . .
C23 C 0.1078(3) 0.55713(6) 0.5070(3) 0.0593(6) Uani 1 1 d . . . . .
H23 H 0.0284 0.5697 0.5391 0.071 Uiso 1 1 calc R . . . .
C24 C 0.1658(2) 0.52700(5) 0.6116(3) 0.0424(4) Uani 1 1 d . . . . .
C25 C 0.2808(2) 0.50921(6) 0.5550(3) 0.0586(6) Uani 1 1 d . . . . .
H25 H 0.3231 0.4887 0.6218 0.070 Uiso 1 1 calc R . . . .
C26 C 0.3331(3) 0.52221(7) 0.3969(3) 0.0626(6) Uani 1 1 d . . . . .
H26 H 0.4098 0.5097 0.3579 0.075 Uiso 1 1 calc R . . . .
C27 C 0.0963(2) 0.51511(6) 0.7774(3) 0.0483(5) Uani 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 H1 0.8200 . ?
O1 C4 1.351(2) . ?
O2 H2 0.8200 . ?
O2 C10 1.351(3) . ?
O3 C21 1.203(2) . ?
O4 H4 0.8200 . ?
O4 C21 1.301(2) . ?
N1 C1 1.323(2) . ?
N1 C2 1.361(2) . ?
N2 N3 1.370(2) . ?
N2 C1 1.356(2) . ?
N2 C15 1.434(2) . ?
N3 C2 1.318(2) . ?
C1 C3 1.476(3) . ?
C2 C9 1.469(3) . ?
C3 C4 1.390(3) . ?
C3 C8 1.383(3) . ?
C4 C5 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 C14 1.400(3) . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.368(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(3) . ?
C15 C20 1.378(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(3) . ?
C18 C19 1.377(3) . ?
C18 C21 1.494(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(3) . ?
C20 H20 0.9300 . ?
O5 C27 1.229(2) . ?
N4 C22 1.317(3) . ?
N4 C26 1.315(3) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C27 1.316(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.371(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.375(3) . ?
C24 C25 1.370(3) . ?
C24 C27 1.506(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.385(3) . ?
C26 H26 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C21 O4 H4 109.5 . . ?
C1 N1 C2 104.23(15) . . ?
N3 N2 C15 119.75(15) . . ?
C1 N2 N3 108.60(15) . . ?
C1 N2 C15 131.64(16) . . ?
C2 N3 N2 103.90(15) . . ?
N1 C1 N2 109.76(16) . . ?
N1 C1 C3 123.09(16) . . ?
N2 C1 C3 127.11(16) . . ?
N1 C2 C9 124.12(17) . . ?
N3 C2 N1 113.50(16) . . ?
N3 C2 C9 122.37(17) . . ?
C4 C3 C1 118.94(17) . . ?
C8 C3 C1 121.00(17) . . ?
C8 C3 C4 119.95(18) . . ?
O1 C4 C3 117.02(17) . . ?
O1 C4 C5 123.80(19) . . ?
C5 C4 C3 119.18(19) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.4 . . ?
C8 C7 C6 119.1(2) . . ?
C8 C7 H7 120.4 . . ?
C3 C8 H8 119.7 . . ?
C7 C8 C3 120.5(2) . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C2 120.75(18) . . ?
C10 C9 C14 118.44(19) . . ?
C14 C9 C2 120.81(18) . . ?
O2 C10 C9 122.6(2) . . ?
O2 C10 C11 117.0(2) . . ?
C11 C10 C9 120.4(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(2) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C16 C15 N2 121.05(16) . . ?
C20 C15 N2 118.98(17) . . ?
C20 C15 C16 119.94(18) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.76(19) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.07(19) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C21 120.37(18) . . ?
C19 C18 C17 118.48(18) . . ?
C19 C18 C21 121.14(18) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.09(18) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 119.52(19) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
O3 C21 O4 123.33(19) . . ?
O3 C21 C18 123.6(2) . . ?
O4 C21 C18 113.04(18) . . ?
C26 N4 C22 117.49(19) . . ?
H5A N5 H5B 120.0 . . ?
C27 N5 H5A 120.0 . . ?
C27 N5 H5B 120.0 . . ?
N4 C22 H22 118.2 . . ?
N4 C22 C23 123.6(2) . . ?
C23 C22 H22 118.2 . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.0(2) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 C27 117.87(18) . . ?
C25 C24 C23 117.78(19) . . ?
C25 C24 C27 124.32(18) . . ?
C24 C25 H25 120.5 . . ?
C24 C25 C26 119.0(2) . . ?
C26 C25 H25 120.5 . . ?
N4 C26 C25 123.0(2) . . ?
N4 C26 H26 118.5 . . ?
C25 C26 H26 118.5 . . ?
O5 C27 N5 123.3(2) . . ?
O5 C27 C24 118.52(18) . . ?
N5 C27 C24 118.18(18) . . ?

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 C4 C5 C6 178.2(2) . . . . ?
O2 C10 C11 C12 179.8(2) . . . . ?
N1 C1 C3 C4 72.1(2) . . . . ?
N1 C1 C3 C8 -104.2(2) . . . . ?
N1 C2 C9 C10 176.31(18) . . . . ?
N1 C2 C9 C14 -2.8(3) . . . . ?
N2 N3 C2 N1 0.1(2) . . . . ?
N2 N3 C2 C9 178.82(16) . . . . ?
N2 C1 C3 C4 -110.3(2) . . . . ?
N2 C1 C3 C8 73.4(3) . . . . ?
N2 C15 C16 C17 -178.47(18) . . . . ?
N2 C15 C20 C19 -179.35(18) . . . . ?
N3 N2 C1 N1 0.6(2) . . . . ?
N3 N2 C1 C3 -177.23(17) . . . . ?
N3 N2 C15 C16 -171.89(18) . . . . ?
N3 N2 C15 C20 5.8(3) . . . . ?
N3 C2 C9 C10 -2.3(3) . . . . ?
N3 C2 C9 C14 178.63(18) . . . . ?
C1 N1 C2 N3 0.3(2) . . . . ?
C1 N1 C2 C9 -178.43(17) . . . . ?
C1 N2 N3 C2 -0.43(19) . . . . ?
C1 N2 C15 C16 7.4(3) . . . . ?
C1 N2 C15 C20 -174.88(18) . . . . ?
C1 C3 C4 O1 4.7(3) . . . . ?
C1 C3 C4 C5 -175.22(18) . . . . ?
C1 C3 C8 C7 176.77(19) . . . . ?
C2 N1 C1 N2 -0.53(19) . . . . ?
C2 N1 C1 C3 177.43(16) . . . . ?
C2 C9 C10 O2 0.8(3) . . . . ?
C2 C9 C10 C11 179.5(2) . . . . ?
C2 C9 C14 C13 179.6(2) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C4 C3 C8 C7 0.6(3) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C3 -1.4(3) . . . . ?
C8 C3 C4 O1 -178.96(18) . . . . ?
C8 C3 C4 C5 1.1(3) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C9 C14 C13 0.4(3) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
C12 C13 C14 C9 0.9(4) . . . . ?
C14 C9 C10 O2 180.0(2) . . . . ?
C14 C9 C10 C11 -1.4(3) . . . . ?
C15 N2 N3 C2 178.99(15) . . . . ?
C15 N2 C1 N1 -178.70(17) . . . . ?
C15 N2 C1 C3 3.4(3) . . . . ?
C15 C16 C17 C18 -2.8(3) . . . . ?
C16 C15 C20 C19 -1.6(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C16 C17 C18 C21 -179.3(2) . . . . ?
C17 C18 C19 C20 2.8(3) . . . . ?
C17 C18 C21 O3 172.7(2) . . . . ?
C17 C18 C21 O4 -7.4(3) . . . . ?
C18 C19 C20 C15 -1.8(3) . . . . ?
C19 C18 C21 O3 -6.1(3) . . . . ?
C19 C18 C21 O4 173.8(2) . . . . ?
C20 C15 C16 C17 3.8(3) . . . . ?
C21 C18 C19 C20 -178.40(19) . . . . ?
N4 C22 C23 C24 1.3(4) . . . . ?
C22 N4 C26 C25 -1.4(4) . . . . ?
C22 C23 C24 C25 -1.3(3) . . . . ?
C22 C23 C24 C27 -179.7(2) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C23 C24 C27 O5 12.7(3) . . . . ?
C23 C24 C27 N5 -168.4(2) . . . . ?
C24 C25 C26 N4 1.3(4) . . . . ?
C25 C24 C27 O5 -165.5(2) . . . . ?
C25 C24 C27 N5 13.3(3) . . . . ?
C26 N4 C22 C23 0.0(4) . . . . ?
C27 C24 C25 C26 178.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
