# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_complex_1
_database_code_depnum_ccdc_archive 'CCDC 1831638'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'DMAN 4-hydroxybenzoic acid 4-hydroxybenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N2, C7 H6 O3, C7 H5 O3'
_chemical_formula_sum            'C28 H30 N2 O6'
_chemical_formula_weight         490.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0056 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.4729(5)
_cell_length_b                   14.6030(3)
_cell_length_c                   14.7655(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.920(3)
_cell_angle_gamma                90
_cell_volume                     2472.40(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4252
_cell_measurement_theta_min      1.7250
_cell_measurement_theta_max      30.5150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1040

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_min  0.64533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_reflns_number            21939
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.721
_diffrn_reflns_theta_max         25.502
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5028
_reflns_number_gt                3691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.1498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5028
_refine_ls_number_parameters     445
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0968
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H22 H 0.6804(14) -0.0146(12) 0.4180(12) 0.023(4) Uiso 1 1 d . . . . .
H21 H 0.7631(15) 0.1476(12) 0.1471(13) 0.028(5) Uiso 1 1 d . . . . .
H23 H 0.8776(16) 0.0169(12) 0.3762(12) 0.027(5) Uiso 1 1 d . . . . .
H20 H 1.0605(19) 0.1581(13) 0.1602(13) 0.042(6) Uiso 1 1 d . . . . .
H24 H 0.5687(16) 0.1152(12) 0.1845(12) 0.028(5) Uiso 1 1 d . . . . .
H30 H 0.436(2) 0.0495(16) 0.2822(16) 0.063(7) Uiso 1 1 d . . . . .
O2 O 0.97707(11) 0.15349(7) 0.16659(8) 0.0278(3) Uani 1 1 d . . . . .
O1 O 1.04167(10) 0.06420(8) 0.28146(8) 0.0295(3) Uani 1 1 d . . . . .
O6 O 0.49669(11) 0.02956(8) 0.32728(9) 0.0293(3) Uani 1 1 d . . . . .
C21 C 0.81135(15) 0.03799(11) 0.33851(13) 0.0249(4) Uani 1 1 d . . . . .
C20 C 0.69765(15) 0.02066(11) 0.36023(13) 0.0249(4) Uani 1 1 d . . . . .
C15 C 0.96125(15) 0.09947(10) 0.23835(12) 0.0231(4) Uani 1 1 d . . . . .
C16 C 0.83710(14) 0.08616(10) 0.25980(12) 0.0225(4) Uani 1 1 d . . . . .
C19 C 0.60617(15) 0.04958(10) 0.30307(12) 0.0243(4) Uani 1 1 d . . . . .
C17 C 0.74510(15) 0.11636(11) 0.20329(13) 0.0242(4) Uani 1 1 d . . . . .
C18 C 0.63060(15) 0.09798(10) 0.22406(12) 0.0234(4) Uani 1 1 d . . . . .
H7 H 0.9527(16) -0.2500(12) 0.0829(12) 0.027(5) Uiso 1 1 d . . . . .
H13 H 1.5022(16) -0.0877(12) 0.0325(12) 0.026(5) Uiso 1 1 d . . . . .
H14 H 1.5026(16) -0.2023(12) 0.1599(12) 0.027(5) Uiso 1 1 d . . . . .
H4 H 1.2870(14) -0.4313(13) -0.1309(12) 0.024(5) Uiso 1 1 d . . . . .
H12 H 1.4171(16) -0.0272(14) 0.0870(13) 0.035(5) Uiso 1 1 d . . . . .
H9 H 0.9931(17) -0.0774(12) 0.0698(12) 0.029(5) Uiso 1 1 d . . . . .
H6 H 0.9216(16) -0.3765(12) -0.0128(12) 0.025(5) Uiso 1 1 d . . . . .
H11 H 1.1208(14) -0.0962(13) 0.2387(12) 0.025(5) Uiso 1 1 d . . . . .
H5 H 1.0825(15) -0.4363(13) -0.0954(12) 0.030(5) Uiso 1 1 d . . . . .
H2 H 1.5058(16) -0.2437(12) -0.0125(12) 0.028(5) Uiso 1 1 d . . . . .
H3 H 1.4769(15) -0.3729(12) -0.1102(12) 0.026(5) Uiso 1 1 d . . . . .
H8 H 1.1003(16) -0.0124(14) 0.1004(13) 0.035(5) Uiso 1 1 d . . . . .
H10 H 1.1045(16) -0.0650(13) 0.0015(14) 0.033(5) Uiso 1 1 d . . . . .
H15 H 1.4293(15) -0.1311(13) 0.2146(13) 0.029(5) Uiso 1 1 d . . . . .
H18 H 1.1509(16) -0.2037(13) 0.2412(12) 0.034(5) Uiso 1 1 d . . . . .
H16 H 1.3720(16) -0.0565(12) -0.0101(13) 0.026(5) Uiso 1 1 d . . . . .
H17 H 1.0192(19) -0.1643(13) 0.2086(13) 0.040(5) Uiso 1 1 d . . . . .
H1 H 1.2462(18) -0.1390(13) 0.1085(13) 0.044(6) Uiso 1 1 d . . . . .
H19 H 1.3822(17) -0.2314(14) 0.2003(13) 0.038(5) Uiso 1 1 d . . . . .
N2 N 1.35840(12) -0.15445(8) 0.08769(10) 0.0215(3) Uani 1 1 d . . . . .
N1 N 1.13848(12) -0.14747(8) 0.11339(9) 0.0213(3) Uani 1 1 d . . . . .
C9 C 1.22244(14) -0.26689(10) 0.01545(11) 0.0207(4) Uani 1 1 d . . . . .
C10 C 1.20439(15) -0.34435(10) -0.04304(12) 0.0233(4) Uani 1 1 d . . . . .
C2 C 1.01697(15) -0.27307(11) 0.05117(13) 0.0255(4) Uani 1 1 d . . . . .
C1 C 1.12351(14) -0.23213(10) 0.06035(12) 0.0219(4) Uani 1 1 d . . . . .
C8 C 1.33785(14) -0.23133(10) 0.02540(12) 0.0218(4) Uani 1 1 d . . . . .
C5 C 1.29979(16) -0.38104(11) -0.08930(13) 0.0266(4) Uani 1 1 d . . . . .
C4 C 1.09152(15) -0.38397(11) -0.05262(13) 0.0257(4) Uani 1 1 d . . . . .
C6 C 1.40915(16) -0.34430(12) -0.07879(13) 0.0291(4) Uani 1 1 d . . . . .
C7 C 1.42752(15) -0.26855(12) -0.02085(13) 0.0276(4) Uani 1 1 d . . . . .
C3 C 1.00080(16) -0.35012(11) -0.00544(13) 0.0288(4) Uani 1 1 d . . . . .
C11 C 1.07888(17) -0.06898(11) 0.06714(14) 0.0274(4) Uani 1 1 d . . . . .
C13 C 1.41648(17) -0.07537(11) 0.04453(14) 0.0267(4) Uani 1 1 d . . . . .
C12 C 1.10372(17) -0.15558(12) 0.20876(13) 0.0280(4) Uani 1 1 d . . . . .
C14 C 1.42294(16) -0.18277(12) 0.17143(13) 0.0270(4) Uani 1 1 d . . . . .
H25 H 1.2867(13) 0.2320(11) 0.5022(12) 0.015(4) Uiso 1 1 d . . . . .
H26 H 1.2968(15) 0.1172(13) 0.3898(12) 0.029(5) Uiso 1 1 d . . . . .
H27 H 1.2331(14) 0.3126(12) 0.1952(12) 0.022(5) Uiso 1 1 d . . . . .
H28 H 1.2294(17) 0.4241(14) 0.3109(13) 0.039(5) Uiso 1 1 d . . . . .
H29 H 1.242(2) 0.3824(16) 0.5379(17) 0.060(7) Uiso 1 1 d . . . . .
O4 O 1.20430(10) 0.15381(8) 0.13431(8) 0.0264(3) Uani 1 1 d . . . . .
O3 O 1.32758(10) 0.06402(8) 0.21324(9) 0.0303(3) Uani 1 1 d . . . . .
O5 O 1.25117(11) 0.40730(8) 0.47646(9) 0.0281(3) Uani 1 1 d . . . . .
C24 C 1.28379(14) 0.18152(11) 0.37026(12) 0.0225(4) Uani 1 1 d . . . . .
C23 C 1.26610(13) 0.20480(11) 0.27950(12) 0.0219(4) Uani 1 1 d . . . . .
C27 C 1.24377(15) 0.36305(11) 0.32394(12) 0.0249(4) Uani 1 1 d . . . . .
C26 C 1.25786(14) 0.33932(10) 0.41457(12) 0.0220(4) Uani 1 1 d . . . . .
C25 C 1.27810(14) 0.24730(11) 0.43791(13) 0.0218(4) Uani 1 1 d . . . . .
C28 C 1.24542(15) 0.29668(11) 0.25775(13) 0.0241(4) Uani 1 1 d . . . . .
C22 C 1.26707(14) 0.13539(11) 0.20526(12) 0.0238(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
O2 C15 1.338(2) . ?
O1 C15 1.217(2) . ?
O6 C19 1.349(2) . ?
C21 C20 1.377(2) . ?
C21 C16 1.398(2) . ?
C20 C19 1.390(2) . ?
C15 C16 1.482(2) . ?
C16 C17 1.395(2) . ?
C19 C18 1.400(2) . ?
C17 C18 1.385(2) . ?
N2 C8 1.465(2) . ?
N2 C14 1.479(2) . ?
N2 C13 1.487(2) . ?
N1 C1 1.470(2) . ?
N1 C12 1.481(2) . ?
N1 C11 1.489(2) . ?
C9 C8 1.425(2) . ?
C9 C1 1.427(2) . ?
C9 C10 1.434(2) . ?
C10 C5 1.415(2) . ?
C10 C4 1.421(2) . ?
C2 C1 1.363(2) . ?
C2 C3 1.410(2) . ?
C8 C7 1.366(2) . ?
C5 C6 1.369(2) . ?
C4 C3 1.364(2) . ?
C6 C7 1.410(2) . ?
O4 C22 1.280(2) . ?
O3 C22 1.2556(19) . ?
O5 C26 1.3533(19) . ?
C24 C25 1.389(2) . ?
C24 C23 1.391(2) . ?
C23 C28 1.398(2) . ?
C23 C22 1.493(2) . ?
C27 C28 1.377(2) . ?
C27 C26 1.386(2) . ?
C26 C25 1.405(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 C21 C16 120.94(16) . . ?
C21 C20 C19 120.30(17) . . ?
O1 C15 O2 122.88(16) . . ?
O1 C15 C16 123.33(16) . . ?
O2 C15 C16 113.78(14) . . ?
C17 C16 C21 118.65(16) . . ?
C17 C16 C15 122.95(16) . . ?
C21 C16 C15 118.35(15) . . ?
O6 C19 C20 117.64(16) . . ?
O6 C19 C18 122.96(16) . . ?
C20 C19 C18 119.40(16) . . ?
C18 C17 C16 120.69(17) . . ?
C17 C18 C19 120.00(16) . . ?
C8 N2 C14 112.09(13) . . ?
C8 N2 C13 113.00(13) . . ?
C14 N2 C13 110.88(14) . . ?
C1 N1 C12 114.13(13) . . ?
C1 N1 C11 111.06(13) . . ?
C12 N1 C11 111.32(14) . . ?
C8 C9 C1 124.98(15) . . ?
C8 C9 C10 117.67(14) . . ?
C1 C9 C10 117.35(14) . . ?
C5 C10 C4 120.98(16) . . ?
C5 C10 C9 119.41(15) . . ?
C4 C10 C9 119.59(15) . . ?
C1 C2 C3 120.56(16) . . ?
C2 C1 C9 121.49(15) . . ?
C2 C1 N1 120.65(15) . . ?
C9 C1 N1 117.78(14) . . ?
C7 C8 C9 121.06(15) . . ?
C7 C8 N2 120.70(15) . . ?
C9 C8 N2 118.24(14) . . ?
C6 C5 C10 121.19(16) . . ?
C3 C4 C10 120.65(16) . . ?
C5 C6 C7 119.62(16) . . ?
C8 C7 C6 121.04(16) . . ?
C4 C3 C2 120.28(16) . . ?
C25 C24 C23 121.00(15) . . ?
C24 C23 C28 118.30(16) . . ?
C24 C23 C22 122.47(14) . . ?
C28 C23 C22 119.23(15) . . ?
C28 C27 C26 120.34(15) . . ?
O5 C26 C27 117.45(14) . . ?
O5 C26 C25 123.28(16) . . ?
C27 C26 C25 119.27(15) . . ?
C24 C25 C26 119.77(16) . . ?
C27 C28 C23 121.25(17) . . ?
O3 C22 O4 123.05(16) . . ?
O3 C22 C23 120.82(16) . . ?
O4 C22 C23 116.12(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H20 O4 0.97(2) 1.71(2) 2.6659(17) 170.5(18) .
O6 H30 O3 0.99(2) 1.60(3) 2.5757(18) 169(2) 1_455
C13 H12 O3 0.94(2) 2.54(2) 3.400(2) 152.5(16) .
C12 H11 O1 0.990(18) 2.598(18) 3.466(2) 146.4(13) .
C13 H16 O5 0.980(19) 2.586(18) 3.241(2) 124.3(13) 4_565
N1 H1 N2 1.25(2) 1.35(2) 2.5661(19) 161.8(17) .
O5 H29 O4 0.99(2) 1.59(3) 2.5695(17) 170(2) 4_566

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'slow evaporation at room temperature in diethylether'
####################################################################### 
# 
# 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_complex_6
_database_code_depnum_ccdc_archive 'CCDC 1831645'
_audit_update_record             
;
2018-04-13 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT353_complex_6           
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H1       .       1.09 Ang.  
RESPONSE: Due to involvement in a short strong intramolecular hydrogen bond N1-H1...N2. 
;
_vrf_PLAT355_complex_6           
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H20      .       1.10 Ang.  
RESPONSE: Due to involvement in a short strong charge assisted hydrogen bond O1-H20...O4. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'DMAN 4-cyanobenzoate 4-cyanobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N2, 2(C8 H5 N1 O2), C8 H4 N1 O2'
_chemical_formula_sum            'C38 H33 N5 O6'
_chemical_formula_weight         655.69

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   21.6378(4)
_cell_length_b                   9.17650(10)
_cell_length_c                   18.3236(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.447(2)
_cell_angle_gamma                90
_cell_volume                     3362.66(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    11399
_cell_measurement_theta_min      4.8220
_cell_measurement_theta_max      71.8350

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_min  0.70734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150
_diffrn_ambient_environment      air
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            23758
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.422
_diffrn_reflns_theta_max         71.910
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6514
_reflns_number_gt                5571
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0729P)²+0.6089P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6514
_refine_ls_number_parameters     574
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.12865(5) 0.08908(12) 0.08344(7) 0.0257(2) Uani 1 1 d . . . . .
N1 N 0.23369(5) 0.15966(12) 0.05588(6) 0.0227(2) Uani 1 1 d . . . . .
C9 C 0.23655(6) 0.14363(13) 0.19242(7) 0.0220(3) Uani 1 1 d . . . . .
C2 C 0.33767(7) 0.20241(15) 0.16991(8) 0.0275(3) Uani 1 1 d . . . . .
C1 C 0.27147(6) 0.16666(13) 0.14156(7) 0.0217(2) Uani 1 1 d . . . . .
C10 C 0.27442(7) 0.15793(14) 0.27518(8) 0.0258(3) Uani 1 1 d . . . . .
C3 C 0.37441(7) 0.21286(16) 0.25164(8) 0.0300(3) Uani 1 1 d . . . . .
C7 C 0.13745(8) 0.09897(18) 0.22082(9) 0.0371(3) Uani 1 1 d . . . . .
C4 C 0.34353(7) 0.18994(14) 0.30292(8) 0.0286(3) Uani 1 1 d . . . . .
C8 C 0.16707(7) 0.11125(14) 0.16724(8) 0.0256(3) Uani 1 1 d . . . . .
C11 C 0.26226(7) 0.05643(17) 0.01455(8) 0.0329(3) Uani 1 1 d . . . . .
C5 C 0.24177(8) 0.14283(17) 0.32860(9) 0.0352(3) Uani 1 1 d . . . . .
C14 C 0.10758(9) -0.06426(17) 0.06620(9) 0.0382(3) Uani 1 1 d . . . . .
C13 C 0.07157(8) 0.18960(18) 0.05075(10) 0.0386(3) Uani 1 1 d . . . . .
C12 C 0.22468(7) 0.30808(15) 0.02030(8) 0.0298(3) Uani 1 1 d . . . . .
C6 C 0.17497(9) 0.11562(19) 0.30210(10) 0.0422(4) Uani 1 1 d . . . . .
H4 H 0.3693(8) 0.1976(18) 0.3597(10) 0.030(4) Uiso 1 1 d . . . . .
H5 H 0.2692(9) 0.153(2) 0.3844(11) 0.040(5) Uiso 1 1 d . . . . .
H3 H 0.4226(9) 0.238(2) 0.2725(11) 0.040(5) Uiso 1 1 d . . . . .
H2 H 0.3596(9) 0.225(2) 0.1332(11) 0.037(4) Uiso 1 1 d . . . . .
H7 H 0.0891(9) 0.077(2) 0.2021(11) 0.045(5) Uiso 1 1 d . . . . .
H6 H 0.1525(10) 0.105(2) 0.3399(12) 0.055(6) Uiso 1 1 d . . . . .
H11 H 0.1931(9) 0.2997(19) -0.0358(11) 0.036(4) Uiso 1 1 d . . . . .
H10 H 0.2299(9) 0.046(2) -0.0415(11) 0.040(5) Uiso 1 1 d . . . . .
H19 H 0.0894(9) -0.077(2) 0.0104(12) 0.041(5) Uiso 1 1 d . . . . .
H8 H 0.3057(10) 0.092(2) 0.0159(11) 0.042(5) Uiso 1 1 d . . . . .
H9 H 0.2680(9) -0.041(2) 0.0397(12) 0.047(5) Uiso 1 1 d . . . . .
H13 H 0.2057(9) 0.376(2) 0.0503(11) 0.042(5) Uiso 1 1 d . . . . .
H17 H 0.1467(11) -0.129(2) 0.0881(13) 0.055(6) Uiso 1 1 d . . . . .
H12 H 0.2695(10) 0.346(2) 0.0233(11) 0.049(5) Uiso 1 1 d . . . . .
H14 H 0.0869(10) 0.294(2) 0.0651(12) 0.054(6) Uiso 1 1 d . . . . .
H15 H 0.0501(9) 0.177(2) -0.0077(12) 0.042(5) Uiso 1 1 d . . . . .
H16 H 0.0372(10) 0.167(2) 0.0729(12) 0.047(5) Uiso 1 1 d . . . . .
H1 H 0.1849(9) 0.123(2) 0.0536(11) 0.046(5) Uiso 1 1 d . . . . .
H18 H 0.0735(10) -0.091(2) 0.0899(12) 0.053(6) Uiso 1 1 d . . . . .
O5 O 0.20837(5) 0.53901(11) 0.19408(6) 0.0349(2) Uani 1 1 d . . . . .
O6 O 0.15797(5) 0.72350(13) 0.22812(6) 0.0395(3) Uani 1 1 d . . . . .
C25 C 0.26893(7) 0.76237(17) 0.37051(9) 0.0322(3) Uani 1 1 d . . . . .
C27 C 0.37616(7) 0.67614(17) 0.45718(8) 0.0325(3) Uani 1 1 d . . . . .
C23 C 0.20506(6) 0.64168(15) 0.24249(8) 0.0271(3) Uani 1 1 d . . . . .
C24 C 0.26504(6) 0.64959(15) 0.31820(8) 0.0258(3) Uani 1 1 d . . . . .
C29 C 0.37228(7) 0.56172(17) 0.40574(9) 0.0344(3) Uani 1 1 d . . . . .
C30 C 0.31702(7) 0.54948(15) 0.33635(9) 0.0302(3) Uani 1 1 d . . . . .
C26 C 0.32442(7) 0.77701(18) 0.43995(9) 0.0354(3) Uani 1 1 d . . . . .
C28 C 0.43503(8) 0.6921(2) 0.52885(10) 0.0431(4) Uani 1 1 d . . . . .
N5 N 0.48172(8) 0.7035(2) 0.58550(10) 0.0630(5) Uani 1 1 d . . . . .
H29 H 0.2327(9) 0.832(2) 0.3555(10) 0.038(5) Uiso 1 1 d . . . . .
H26 H 0.3138(8) 0.4698(19) 0.2992(10) 0.034(4) Uiso 1 1 d . . . . .
H27 H 0.4093(10) 0.491(2) 0.4193(11) 0.047(5) Uiso 1 1 d . . . . .
H28 H 0.3264(9) 0.859(2) 0.4777(12) 0.045(5) Uiso 1 1 d . . . . .
H21 H 0.1727(12) 0.550(3) 0.1403(15) 0.071(7) Uiso 1 1 d . . . . .
O3 O 0.11803(5) 0.55787(11) 0.05450(6) 0.0332(2) Uani 1 1 d . . . . .
O4 O 0.18668(5) 0.66722(12) 0.00606(6) 0.0361(2) Uani 1 1 d . . . . .
C31 C 0.13220(6) 0.61166(14) -0.00025(8) 0.0253(3) Uani 1 1 d . . . . .
C32 C 0.07845(6) 0.60713(13) -0.08248(7) 0.0233(3) Uani 1 1 d . . . . .
C33 C 0.02014(7) 0.52687(15) -0.09853(8) 0.0266(3) Uani 1 1 d . . . . .
C38 C 0.08765(7) 0.68221(15) -0.14358(9) 0.0296(3) Uani 1 1 d . . . . .
C35 C -0.01773(7) 0.59433(15) -0.23487(8) 0.0286(3) Uani 1 1 d . . . . .
C34 C -0.02814(6) 0.52050(15) -0.17433(8) 0.0286(3) Uani 1 1 d . . . . .
C36 C -0.06606(7) 0.58721(17) -0.31509(9) 0.0359(3) Uani 1 1 d . . . . .
N3 N -0.10267(8) 0.58357(18) -0.37961(8) 0.0504(4) Uani 1 1 d . . . . .
C37 C 0.04022(7) 0.67566(16) -0.21976(9) 0.0328(3) Uani 1 1 d . . . . .
H30 H 0.1273(9) 0.738(2) -0.1324(11) 0.039(5) Uiso 1 1 d . . . . .
H33 H 0.0137(8) 0.4758(19) -0.0546(10) 0.035(4) Uiso 1 1 d . . . . .
H32 H -0.0693(9) 0.4646(19) -0.1865(10) 0.036(4) Uiso 1 1 d . . . . .
H31 H 0.0477(9) 0.725(2) -0.2628(11) 0.041(5) Uiso 1 1 d . . . . .
O1 O 0.28751(5) 0.74239(11) 0.12749(7) 0.0389(3) Uani 1 1 d . . . . .
O2 O 0.34133(6) 0.54291(12) 0.11373(7) 0.0423(3) Uani 1 1 d . . . . .
C22 C 0.44840(7) 0.60189(16) 0.25591(9) 0.0336(3) Uani 1 1 d . . . . .
C16 C 0.39468(7) 0.69687(15) 0.22403(8) 0.0289(3) Uani 1 1 d . . . . .
C18 C 0.44601(7) 0.86252(17) 0.33211(9) 0.0354(3) Uani 1 1 d . . . . .
C19 C 0.49941(7) 0.76583(17) 0.36385(8) 0.0326(3) Uani 1 1 d . . . . .
C20 C 0.55430(7) 0.7997(2) 0.43648(9) 0.0404(4) Uani 1 1 d . . . . .
C21 C 0.50031(7) 0.63507(18) 0.32574(9) 0.0357(3) Uani 1 1 d . . . . .
C17 C 0.39359(7) 0.82689(16) 0.26261(9) 0.0325(3) Uani 1 1 d . . . . .
C15 C 0.33870(7) 0.65200(15) 0.14969(9) 0.0307(3) Uani 1 1 d . . . . .
N4 N 0.59986(7) 0.8211(2) 0.49294(9) 0.0580(5) Uani 1 1 d . . . . .
H25 H 0.4482(10) 0.511(2) 0.2270(12) 0.049(5) Uiso 1 1 d . . . . .
H24 H 0.5369(9) 0.566(2) 0.3499(11) 0.040(5) Uiso 1 1 d . . . . .
H23 H 0.4450(9) 0.954(2) 0.3607(12) 0.046(5) Uiso 1 1 d . . . . .
H22 H 0.3547(10) 0.892(2) 0.2383(12) 0.050(5) Uiso 1 1 d . . . . .
H20 H 0.2454(13) 0.701(3) 0.0757(16) 0.085(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C8 1.4545(16) . ?
N2 C13 1.4732(18) . ?
N2 C14 1.4757(18) . ?
N1 C1 1.4687(15) . ?
N1 C11 1.4869(17) . ?
N1 C12 1.4903(17) . ?
C9 C1 1.4218(17) . ?
C9 C8 1.4254(18) . ?
C9 C10 1.4280(17) . ?
C2 C1 1.3642(18) . ?
C2 C3 1.4052(19) . ?
C10 C4 1.4143(19) . ?
C10 C5 1.4160(19) . ?
C3 C4 1.361(2) . ?
C7 C8 1.3665(19) . ?
C7 C6 1.406(2) . ?
C5 C6 1.361(2) . ?
O5 C23 1.3146(17) . ?
O6 C23 1.2110(17) . ?
C25 C26 1.383(2) . ?
C25 C24 1.3911(19) . ?
C27 C29 1.392(2) . ?
C27 C26 1.393(2) . ?
C27 C28 1.446(2) . ?
C23 C24 1.4964(18) . ?
C24 C30 1.3906(19) . ?
C29 C30 1.378(2) . ?
C28 N5 1.144(2) . ?
O3 C31 1.2565(17) . ?
O4 C31 1.2486(16) . ?
C31 C32 1.5120(17) . ?
C32 C33 1.3919(18) . ?
C32 C38 1.3922(19) . ?
C33 C34 1.3841(19) . ?
C38 C37 1.382(2) . ?
C35 C34 1.390(2) . ?
C35 C37 1.393(2) . ?
C35 C36 1.4439(18) . ?
C36 N3 1.145(2) . ?
O1 C15 1.3178(18) . ?
O2 C15 1.2117(18) . ?
C22 C21 1.376(2) . ?
C22 C16 1.391(2) . ?
C16 C17 1.392(2) . ?
C16 C15 1.4940(19) . ?
C18 C17 1.383(2) . ?
C18 C19 1.395(2) . ?
C19 C21 1.392(2) . ?
C19 C20 1.439(2) . ?
C20 N4 1.141(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C13 113.21(11) . . ?
C8 N2 C14 111.39(11) . . ?
C13 N2 C14 111.56(12) . . ?
C1 N1 C11 113.73(10) . . ?
C1 N1 C12 110.74(10) . . ?
C11 N1 C12 111.70(11) . . ?
C1 C9 C8 125.28(11) . . ?
C1 C9 C10 116.70(11) . . ?
C8 C9 C10 118.00(12) . . ?
C1 C2 C3 120.45(12) . . ?
C2 C1 C9 121.98(12) . . ?
C2 C1 N1 119.51(11) . . ?
C9 C1 N1 118.42(11) . . ?
C4 C10 C5 120.66(13) . . ?
C4 C10 C9 120.01(12) . . ?
C5 C10 C9 119.32(13) . . ?
C4 C3 C2 119.86(13) . . ?
C8 C7 C6 120.83(14) . . ?
C3 C4 C10 120.94(12) . . ?
C7 C8 C9 120.71(12) . . ?
C7 C8 N2 120.74(12) . . ?
C9 C8 N2 118.55(11) . . ?
C6 C5 C10 120.91(14) . . ?
C5 C6 C7 120.19(14) . . ?
C26 C25 C24 120.60(13) . . ?
C29 C27 C26 120.82(13) . . ?
C29 C27 C28 119.73(14) . . ?
C26 C27 C28 119.44(14) . . ?
O6 C23 O5 123.76(13) . . ?
O6 C23 C24 122.10(12) . . ?
O5 C23 C24 114.14(11) . . ?
C30 C24 C25 119.74(13) . . ?
C30 C24 C23 121.71(12) . . ?
C25 C24 C23 118.54(12) . . ?
C30 C29 C27 119.55(13) . . ?
C29 C30 C24 120.30(13) . . ?
C25 C26 C27 118.97(14) . . ?
N5 C28 C27 179.4(2) . . ?
O4 C31 O3 126.59(12) . . ?
O4 C31 C32 116.31(12) . . ?
O3 C31 C32 117.09(11) . . ?
C33 C32 C38 119.23(12) . . ?
C33 C32 C31 121.02(12) . . ?
C38 C32 C31 119.74(11) . . ?
C34 C33 C32 120.69(12) . . ?
C37 C38 C32 120.76(12) . . ?
C34 C35 C37 120.69(12) . . ?
C34 C35 C36 121.03(13) . . ?
C37 C35 C36 118.28(13) . . ?
C33 C34 C35 119.35(12) . . ?
N3 C36 C35 177.51(18) . . ?
C38 C37 C35 119.27(13) . . ?
C21 C22 C16 120.42(14) . . ?
C22 C16 C17 119.84(14) . . ?
C22 C16 C15 117.83(13) . . ?
C17 C16 C15 122.30(13) . . ?
C17 C18 C19 119.40(14) . . ?
C21 C19 C18 120.46(13) . . ?
C21 C19 C20 119.05(14) . . ?
C18 C19 C20 120.49(15) . . ?
N4 C20 C19 176.2(2) . . ?
C22 C21 C19 119.62(13) . . ?
C18 C17 C16 120.23(13) . . ?
O2 C15 O1 124.10(13) . . ?
O2 C15 C16 122.24(13) . . ?
O1 C15 C16 113.66(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H10 N3 1.002(18) 2.598(18) 3.403(2) 137.3(13) 2_544
C11 H9 O1 0.99(2) 2.49(2) 3.467(2) 168.6(16) 1_545
C12 H13 O3 1.017(19) 2.549(19) 3.4751(18) 151.3(14) .
C12 H12 O2 1.01(2) 2.54(2) 3.2627(18) 128.0(14) .
C13 H14 O3 1.01(2) 2.54(2) 3.519(2) 161.7(16) .
N1 H1 N2 1.095(19) 1.543(19) 2.5916(15) 158.2(17) .
O5 H21 O3 1.00(2) 1.57(2) 2.5641(13) 176(2) .
O4 H20 O2 1.45(3) 2.41(3) 3.3690(15) 119.7(15) .
O1 H20 O4 1.10(3) 1.45(3) 2.5455(14) 172(2) .

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 'grown from isopropanol at 30 degreesC'
####################################################################### 
# 
# 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_complex_2
_database_code_depnum_ccdc_archive 'CCDC 1831639'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT771_complex_2           
;
PROBLEM: Suspect N-H Bond in CIF: N2 -- H1 .. 1.51 Ang.
RESPONSE: N1 is in a short, strong N-H...N hydrogen bond.
;
_vrf_PLAT353_complex_2           
;
PROBLEM: Long N-H (N0.87,N1.01A) N1 - H1 .. 1.12 Ang.
RESPONSE: N1 is in a short, strong N-H...N hydrogen bond.
;
# end Validation Reply Form   

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'DMAN 3-aminobenzoic acid 3-aminobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N2, C7 H7 N1 O2, C7 H6 N1 O2'
_chemical_formula_sum            'C28 H32 N4 O4'
_chemical_formula_weight         488.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 '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 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.8631(4)
_cell_length_b                   21.3774(9)
_cell_length_c                   12.5572(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.968(2)
_cell_angle_gamma                90
_cell_volume                     2472.33(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      39.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1040

_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_min  0.6984
_exptl_absorpt_correction_T_max  0.7477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction  
;

_exptl_special_details           
;
 ?
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_detector                 'CMOS Detector'
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_reflns_number            41246
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.374
_diffrn_reflns_theta_max         39.340
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7542
_reflns_number_gt                5867
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²+0.4736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7542
_refine_ls_number_parameters     453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H32 H 0.407(3) 0.3841(12) 0.405(2) 0.081(7) Uiso 1 1 d . . . . .
H20 H -0.0035(17) 0.3438(7) 0.4839(14) 0.024(4) Uiso 1 1 d . . . . .
H21 H -0.2518(18) 0.3147(8) 0.3863(14) 0.029(4) Uiso 1 1 d . . . . .
H22 H -0.3287(18) 0.2919(7) 0.1886(14) 0.027(4) Uiso 1 1 d . . . . .
H23 H -0.2565(19) 0.2674(8) 0.0302(14) 0.030(4) Uiso 1 1 d . . . . .
H24 H -0.1230(17) 0.2985(7) 0.0171(13) 0.023(4) Uiso 1 1 d . . . . .
H25 H 0.0717(16) 0.3337(7) 0.1845(13) 0.021(4) Uiso 1 1 d . . . . .
O2 O 0.29086(9) 0.36708(4) 0.34491(7) 0.01773(17) Uani 1 1 d . . . . .
O1 O 0.25686(10) 0.36293(5) 0.51132(7) 0.0267(2) Uani 1 1 d . . . . .
C15 C 0.21203(12) 0.35850(5) 0.40680(9) 0.0160(2) Uani 1 1 d . . . . .
C16 C 0.05544(12) 0.34160(5) 0.34258(9) 0.0145(2) Uani 1 1 d . . . . .
C17 C 0.00611(12) 0.32992(5) 0.22542(9) 0.0139(2) Uani 1 1 d . . . . .
C18 C -0.13696(12) 0.31031(5) 0.16742(9) 0.0140(2) Uani 1 1 d . . . . .
C19 C -0.23104(12) 0.30551(5) 0.22845(10) 0.0164(2) Uani 1 1 d . . . . .
C20 C -0.18290(12) 0.31842(5) 0.34412(10) 0.0176(2) Uani 1 1 d . . . . .
C21 C -0.03933(13) 0.33581(5) 0.40233(10) 0.0175(2) Uani 1 1 d . . . . .
N4 N -0.18842(11) 0.29745(5) 0.05158(8) 0.0187(2) Uani 1 1 d . . . . .
H26 H 0.6811(17) 0.4905(7) 0.5978(13) 0.023(4) Uiso 1 1 d . . . . .
H27 H 1.0137(18) 0.4579(8) 0.9043(14) 0.030(4) Uiso 1 1 d . . . . .
H28 H 0.8689(15) 0.5294(7) 0.7707(12) 0.016(3) Uiso 1 1 d . . . . .
H29 H 1.100(2) 0.3503(8) 0.9488(16) 0.039(5) Uiso 1 1 d . . . . .
H30 H 1.0114(19) 0.2951(9) 0.8767(15) 0.037(5) Uiso 1 1 d . . . . .
H31 H 0.8134(16) 0.3117(7) 0.7058(13) 0.020(4) Uiso 1 1 d . . . . .
O4 O 0.60352(9) 0.31040(4) 0.52091(7) 0.01941(17) Uani 1 1 d . . . . .
O3 O 0.52855(9) 0.40777(4) 0.46521(7) 0.01873(17) Uani 1 1 d . . . . .
C23 C 0.74682(12) 0.46034(5) 0.65295(10) 0.0164(2) Uani 1 1 d . . . . .
C22 C 0.73139(11) 0.39566(5) 0.63602(9) 0.0139(2) Uani 1 1 d . . . . .
C24 C 0.85394(13) 0.48300(6) 0.75126(10) 0.0187(2) Uani 1 1 d . . . . .
C25 C 0.94246(12) 0.44234(6) 0.83317(10) 0.0185(2) Uani 1 1 d . . . . .
C26 C 0.92635(12) 0.37759(5) 0.81718(9) 0.0159(2) Uani 1 1 d . . . . .
C27 C 0.82199(12) 0.35508(5) 0.71718(9) 0.0158(2) Uani 1 1 d . . . . .
C28 C 0.61395(11) 0.36777(5) 0.53363(9) 0.0145(2) Uani 1 1 d . . . . .
N3 N 1.00791(11) 0.33594(5) 0.90235(9) 0.0208(2) Uani 1 1 d . . . . .
H18 H 0.1403(19) 0.3061(8) 0.7230(14) 0.030(4) Uiso 1 1 d . . . . .
H2 H 0.2474(18) 0.5637(8) 0.7839(14) 0.032(4) Uiso 1 1 d . . . . .
H6 H 0.4043(18) 0.3020(8) 1.1427(14) 0.031(4) Uiso 1 1 d . . . . .
H17 H 0.2251(17) 0.2838(7) 0.6446(13) 0.023(4) Uiso 1 1 d . . . . .
H7 H 0.4077(17) 0.2728(8) 0.9620(13) 0.028(4) Uiso 1 1 d . . . . .
H19 H 0.2629(18) 0.2517(8) 0.7659(13) 0.028(4) Uiso 1 1 d . . . . .
H5 H 0.3614(17) 0.4073(7) 1.1756(13) 0.025(4) Uiso 1 1 d . . . . .
H4 H 0.3125(18) 0.5142(8) 1.1140(14) 0.030(4) Uiso 1 1 d . . . . .
H3 H 0.2661(18) 0.5914(8) 0.9714(13) 0.029(4) Uiso 1 1 d . . . . .
H15 H 0.4820(18) 0.3136(7) 0.6929(15) 0.029(4) Uiso 1 1 d . . . . .
H16 H 0.5213(17) 0.2799(8) 0.8160(14) 0.028(4) Uiso 1 1 d . . . . .
H14 H 0.5608(19) 0.3544(8) 0.8042(14) 0.032(4) Uiso 1 1 d . . . . .
H8 H 0.1230(17) 0.4504(7) 0.5470(13) 0.024(4) Uiso 1 1 d . . . . .
H11 H 0.3784(18) 0.4651(8) 0.5912(14) 0.031(4) Uiso 1 1 d . . . . .
H9 H 0.1090(19) 0.5110(9) 0.6222(14) 0.035(4) Uiso 1 1 d . . . . .
H10 H 0.0543(18) 0.4427(8) 0.6447(14) 0.030(4) Uiso 1 1 d . . . . .
H13 H 0.484(2) 0.4737(8) 0.7222(15) 0.039(5) Uiso 1 1 d . . . . .
H12 H 0.368(2) 0.5286(9) 0.6583(15) 0.042(5) Uiso 1 1 d . . . . .
H1 H 0.299(2) 0.4018(10) 0.7126(17) 0.054(6) Uiso 1 1 d . . . . .
N1 N 0.27584(10) 0.45324(4) 0.70274(7) 0.01420(18) Uani 1 1 d . . . . .
N2 N 0.34638(10) 0.33988(4) 0.77295(8) 0.01421(18) Uani 1 1 d . . . . .
C9 C 0.32652(11) 0.42240(5) 0.90453(9) 0.01216(19) Uani 1 1 d . . . . .
C10 C 0.33324(11) 0.44053(5) 1.01580(9) 0.0153(2) Uani 1 1 d . . . . .
C1 C 0.29191(11) 0.47052(5) 0.81989(9) 0.0133(2) Uani 1 1 d . . . . .
C8 C 0.35388(11) 0.35849(5) 0.88636(9) 0.0135(2) Uani 1 1 d . . . . .
C6 C 0.38745(13) 0.33402(6) 1.08173(10) 0.0207(2) Uani 1 1 d . . . . .
C7 C 0.38554(12) 0.31550(6) 0.97346(10) 0.0181(2) Uani 1 1 d . . . . .
C5 C 0.36176(12) 0.39467(6) 1.10270(10) 0.0196(2) Uani 1 1 d . . . . .
C4 C 0.30955(13) 0.50383(6) 1.03788(10) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.27177(13) 0.53134(5) 0.84448(10) 0.0194(2) Uani 1 1 d . . . . .
C13 C 0.23516(13) 0.29095(6) 0.72339(11) 0.0198(2) Uani 1 1 d . . . . .
C3 C 0.28135(14) 0.54842(6) 0.95518(10) 0.0217(2) Uani 1 1 d . . . . .
C14 C 0.48965(13) 0.32007(6) 0.77156(11) 0.0212(2) Uani 1 1 d . . . . .
C12 C 0.12633(15) 0.46553(7) 0.62116(10) 0.0248(3) Uani 1 1 d . . . . .
C11 C 0.38681(16) 0.48367(7) 0.66502(11) 0.0267(3) 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
O2 C15 1.2941(13) . ?
O2 H32 1.18(3) . ?
O1 C15 1.2294(13) . ?
C15 C16 1.5082(15) . ?
C16 C17 1.3968(15) . ?
C16 C21 1.3979(15) . ?
C17 C18 1.4006(15) . ?
C17 H25 0.963(15) . ?
C18 N4 1.3858(14) . ?
C18 C19 1.4028(15) . ?
C19 C20 1.3848(16) . ?
C19 H22 0.958(16) . ?
C20 C21 1.3918(16) . ?
C20 H21 1.004(17) . ?
C21 H20 0.972(16) . ?
N4 H23 0.898(18) . ?
N4 H24 0.897(16) . ?
O4 C28 1.2363(13) . ?
O3 C28 1.2887(13) . ?
O3 H32 1.27(3) . ?
C23 C24 1.3933(16) . ?
C23 C22 1.3990(15) . ?
C23 H26 0.997(16) . ?
C22 C27 1.3921(15) . ?
C22 C28 1.5114(15) . ?
C24 C25 1.3904(17) . ?
C24 H28 1.020(14) . ?
C25 C26 1.3994(17) . ?
C25 H27 0.977(17) . ?
C26 C27 1.3940(16) . ?
C26 N3 1.4028(15) . ?
C27 H31 0.937(15) . ?
N3 H29 0.939(19) . ?
N3 H30 0.936(18) . ?
N1 C1 1.4692(13) . ?
N1 C12 1.4872(15) . ?
N1 C11 1.4888(15) . ?
N1 H1 1.12(2) . ?
N2 C8 1.4548(13) . ?
N2 C14 1.4812(14) . ?
N2 C13 1.4819(15) . ?
N2 H1 1.51(2) . ?
C9 C8 1.4267(15) . ?
C9 C10 1.4285(14) . ?
C9 C1 1.4298(14) . ?
C10 C4 1.4174(17) . ?
C10 C5 1.4183(15) . ?
C1 C2 1.3673(15) . ?
C8 C7 1.3763(15) . ?
C6 C5 1.3647(18) . ?
C6 C7 1.4097(17) . ?
C6 H6 0.995(17) . ?
C7 H7 0.962(17) . ?
C5 H5 0.955(15) . ?
C4 C3 1.3629(17) . ?
C4 H4 0.971(16) . ?
C2 C3 1.4073(16) . ?
C2 H2 0.992(17) . ?
C13 H18 0.988(17) . ?
C13 H17 0.971(15) . ?
C13 H19 0.980(16) . ?
C3 H3 0.964(17) . ?
C14 H15 0.974(17) . ?
C14 H16 1.011(17) . ?
C14 H14 0.996(17) . ?
C12 H8 0.975(15) . ?
C12 H9 0.987(18) . ?
C12 H10 0.990(17) . ?
C11 H11 0.984(17) . ?
C11 H13 0.992(19) . ?
C11 H12 0.977(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O2 H32 108.1(12) . . ?
O1 C15 O2 124.49(10) . . ?
O1 C15 C16 119.84(10) . . ?
O2 C15 C16 115.67(9) . . ?
C17 C16 C21 120.11(10) . . ?
C17 C16 C15 120.67(10) . . ?
C21 C16 C15 119.18(10) . . ?
C16 C17 C18 120.50(10) . . ?
C16 C17 H25 120.0(9) . . ?
C18 C17 H25 119.5(9) . . ?
N4 C18 C17 121.84(10) . . ?
N4 C18 C19 119.57(10) . . ?
C17 C18 C19 118.56(10) . . ?
C20 C19 C18 120.86(10) . . ?
C20 C19 H22 120.7(10) . . ?
C18 C19 H22 118.4(10) . . ?
C19 C20 C21 120.44(10) . . ?
C19 C20 H21 119.7(10) . . ?
C21 C20 H21 119.9(10) . . ?
C20 C21 C16 119.46(10) . . ?
C20 C21 H20 121.2(9) . . ?
C16 C21 H20 119.3(9) . . ?
C18 N4 H23 114.2(10) . . ?
C18 N4 H24 116.4(10) . . ?
H23 N4 H24 117.6(14) . . ?
C28 O3 H32 112.6(11) . . ?
C24 C23 C22 119.01(11) . . ?
C24 C23 H26 119.3(9) . . ?
C22 C23 H26 121.7(9) . . ?
C27 C22 C23 119.89(10) . . ?
C27 C22 C28 118.21(10) . . ?
C23 C22 C28 121.85(10) . . ?
C25 C24 C23 120.96(11) . . ?
C25 C24 H28 115.6(8) . . ?
C23 C24 H28 123.3(8) . . ?
C24 C25 C26 120.21(11) . . ?
C24 C25 H27 121.3(10) . . ?
C26 C25 H27 118.4(10) . . ?
C27 C26 C25 118.69(10) . . ?
C27 C26 N3 120.32(11) . . ?
C25 C26 N3 120.91(11) . . ?
C22 C27 C26 121.19(11) . . ?
C22 C27 H31 120.3(9) . . ?
C26 C27 H31 118.5(9) . . ?
O4 C28 O3 124.59(10) . . ?
O4 C28 C22 120.28(10) . . ?
O3 C28 C22 115.13(9) . . ?
C26 N3 H29 115.5(11) . . ?
C26 N3 H30 114.3(11) . . ?
H29 N3 H30 111.8(16) . . ?
C1 N1 C12 111.74(9) . . ?
C1 N1 C11 112.37(9) . . ?
C12 N1 C11 111.36(10) . . ?
C1 N1 H1 101.0(10) . . ?
C12 N1 H1 111.3(10) . . ?
C11 N1 H1 108.6(10) . . ?
C8 N2 C14 112.03(9) . . ?
C8 N2 C13 112.01(9) . . ?
C14 N2 C13 111.05(9) . . ?
C8 N2 H1 98.6(8) . . ?
C14 N2 H1 111.6(8) . . ?
C13 N2 H1 111.0(8) . . ?
C8 C9 C10 118.10(9) . . ?
C8 C9 C1 125.35(9) . . ?
C10 C9 C1 116.55(10) . . ?
C4 C10 C5 120.71(10) . . ?
C4 C10 C9 119.81(10) . . ?
C5 C10 C9 119.47(10) . . ?
C2 C1 C9 122.12(10) . . ?
C2 C1 N1 119.52(10) . . ?
C9 C1 N1 118.36(9) . . ?
C7 C8 C9 120.97(10) . . ?
C7 C8 N2 120.86(10) . . ?
C9 C8 N2 118.17(9) . . ?
C5 C6 C7 120.91(11) . . ?
C5 C6 H6 119.7(10) . . ?
C7 C6 H6 119.3(10) . . ?
C8 C7 C6 119.99(11) . . ?
C8 C7 H7 120.9(9) . . ?
C6 C7 H7 119.1(9) . . ?
C6 C5 C10 120.51(11) . . ?
C6 C5 H5 121.1(9) . . ?
C10 C5 H5 118.3(9) . . ?
C3 C4 C10 121.44(10) . . ?
C3 C4 H4 121.1(10) . . ?
C10 C4 H4 117.5(10) . . ?
C1 C2 C3 120.39(11) . . ?
C1 C2 H2 120.3(10) . . ?
C3 C2 H2 119.3(10) . . ?
N2 C13 H18 109.2(10) . . ?
N2 C13 H17 109.2(9) . . ?
H18 C13 H17 107.2(13) . . ?
N2 C13 H19 110.8(10) . . ?
H18 C13 H19 111.2(13) . . ?
H17 C13 H19 109.1(13) . . ?
C4 C3 C2 119.64(11) . . ?
C4 C3 H3 120.7(10) . . ?
C2 C3 H3 119.7(10) . . ?
N2 C14 H15 108.9(10) . . ?
N2 C14 H16 110.1(9) . . ?
H15 C14 H16 109.6(13) . . ?
N2 C14 H14 108.6(10) . . ?
H15 C14 H14 108.0(13) . . ?
H16 C14 H14 111.4(13) . . ?
N1 C12 H8 106.6(9) . . ?
N1 C12 H9 107.4(10) . . ?
H8 C12 H9 113.0(13) . . ?
N1 C12 H10 110.3(9) . . ?
H8 C12 H10 109.8(13) . . ?
H9 C12 H10 109.6(14) . . ?
N1 C11 H11 107.4(10) . . ?
N1 C11 H13 107.8(10) . . ?
H11 C11 H13 109.2(14) . . ?
N1 C11 H12 108.6(11) . . ?
H11 C11 H12 111.5(14) . . ?
H13 C11 H12 112.2(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 O4 0.962(17) 2.533(17) 3.3621(14) 144.4(13) 4_566
C13 H17 O1 0.971(15) 2.477(16) 3.1485(16) 126.2(12) .
N4 H24 N3 0.897(16) 2.390(17) 3.2459(15) 159.5(13) 1_454
N4 H23 O4 0.898(18) 2.138(18) 3.0183(13) 166.4(15) 4_465
C12 H8 O1 0.975(15) 2.422(16) 3.1051(17) 126.7(12) .
C11 H11 O1 0.984(17) 2.521(17) 3.2031(17) 126.3(12) .
C11 H12 O3 0.977(19) 2.535(18) 3.1200(15) 118.4(13) 3_666
N1 H1 N2 1.12(2) 1.51(2) 2.5875(13) 158.0(17) .

_refine_diff_density_max         0.437
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.054


_exptl_crystal_recrystallization_method 
'slow evaporation from isopropanol solvent at 30 degreesC'
####################################################################### 
# 
# 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_complex_8
_database_code_depnum_ccdc_archive 'CCDC 1831642'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT353_complex_8           
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H1       .       1.20 Ang.  
RESPONSE: H1 is in a short, strong hydrogen N-H...N hydrogen bond.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'DMAN 5-nitro-3-benzoate benzoic acid '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N2, C8 H4 N1 O6'
_chemical_formula_sum            'C22 H23 N3 O6'
_chemical_formula_weight         425.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 '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 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.4488(3)
_cell_length_b                   16.1665(7)
_cell_length_c                   16.8622(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.229(2)
_cell_angle_gamma                90
_cell_volume                     2004.28(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9157
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      43.89

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_min  0.6944
_exptl_absorpt_correction_T_max  0.7487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction  
;

_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_detector                 'CMOS Detector'
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_reflns_number            37365
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         42.136
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7291
_reflns_number_gt                5697
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0676P)²+0.4928P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7291
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1134
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H21 H 0.183(2) 1.0753(9) -0.0830(9) 0.022(4) Uiso 1 1 d . . . . .
H23 H -0.0326(19) 1.2356(9) 0.0619(9) 0.018(3) Uiso 1 1 d . . . . .
H20 H 0.241(2) 1.0304(10) 0.1587(9) 0.024(4) Uiso 1 1 d . . . . .
H22 H 0.029(3) 1.2339(14) -0.2020(14) 0.063(6) Uiso 1 1 d . . . . .
O5 O 0.07136(11) 1.19922(5) -0.15450(4) 0.01730(16) Uani 1 1 d . . . . .
O1 O 0.16134(12) 1.11942(5) 0.26410(5) 0.02070(17) Uani 1 1 d . . . . .
O3 O 0.33225(12) 0.94381(5) -0.04373(5) 0.02248(18) Uani 1 1 d . . . . .
C18 C 0.22108(14) 1.04258(6) 0.03594(6) 0.01305(18) Uani 1 1 d . . . . .
C16 C 0.06551(14) 1.16309(6) -0.02016(6) 0.01235(17) Uani 1 1 d . . . . .
C21 C 0.10123(13) 1.13712(6) 0.12300(6) 0.01232(17) Uani 1 1 d . . . . .
O2 O -0.00889(12) 1.22741(5) 0.21506(5) 0.02119(17) Uani 1 1 d . . . . .
O4 O 0.38055(14) 0.92525(5) 0.08512(5) 0.0276(2) Uani 1 1 d . . . . .
C20 C 0.19507(14) 1.06435(6) 0.11264(6) 0.01328(18) Uani 1 1 d . . . . .
C19 C 0.08325(14) 1.16210(6) 0.20817(6) 0.01420(18) Uani 1 1 d . . . . .
O6 O -0.11695(12) 1.27012(5) -0.08806(5) 0.02415(19) Uani 1 1 d . . . . .
C22 C 0.03388(14) 1.18549(6) 0.05649(6) 0.01273(18) Uani 1 1 d . . . . .
C17 C 0.16140(14) 1.09095(6) -0.03078(6) 0.01348(18) Uani 1 1 d . . . . .
C15 C -0.00293(14) 1.21719(6) -0.09118(6) 0.01404(18) Uani 1 1 d . . . . .
N3 N 0.31786(13) 0.96522(6) 0.02492(6) 0.01714(18) Uani 1 1 d . . . . .
H2 H 0.8156(19) 1.0914(9) 0.4101(9) 0.018(3) Uiso 1 1 d . . . . .
H8 H 0.511(2) 1.0816(10) 0.2795(9) 0.022(4) Uiso 1 1 d . . . . .
H3 H 0.854(2) 1.0786(10) 0.5536(10) 0.028(4) Uiso 1 1 d . . . . .
H6 H 0.470(2) 0.7159(10) 0.5161(10) 0.028(4) Uiso 1 1 d . . . . .
H7 H 0.396(2) 0.7309(10) 0.3757(9) 0.024(4) Uiso 1 1 d . . . . .
H15 H 0.207(2) 0.8425(10) 0.2884(10) 0.026(4) Uiso 1 1 d . . . . .
H12 H 0.848(2) 0.9565(11) 0.2177(10) 0.031(4) Uiso 1 1 d . . . . .
H9 H 0.609(2) 1.0615(10) 0.2053(10) 0.028(4) Uiso 1 1 d . . . . .
H5 H 0.633(2) 0.8188(10) 0.5985(10) 0.028(4) Uiso 1 1 d . . . . .
H14 H 0.2485(19) 0.8919(9) 0.2111(9) 0.020(4) Uiso 1 1 d . . . . .
H13 H 0.894(2) 0.9033(10) 0.2984(10) 0.026(4) Uiso 1 1 d . . . . .
H16 H 0.266(2) 0.9366(11) 0.2998(10) 0.031(4) Uiso 1 1 d . . . . .
H4 H 0.770(2) 0.9545(10) 0.6099(10) 0.025(4) Uiso 1 1 d . . . . .
H11 H 0.953(2) 1.0009(9) 0.2963(9) 0.021(4) Uiso 1 1 d . . . . .
H10 H 0.719(2) 1.1099(11) 0.2801(10) 0.030(4) Uiso 1 1 d . . . . .
H18 H 0.485(2) 0.8045(10) 0.1792(11) 0.031(4) Uiso 1 1 d . . . . .
H17 H 0.429(3) 0.7417(12) 0.2421(11) 0.040(5) Uiso 1 1 d . . . . .
H19 H 0.636(3) 0.7710(12) 0.2495(12) 0.044(5) Uiso 1 1 d . . . . .
H1 H 0.560(3) 0.9179(14) 0.2754(13) 0.061(6) Uiso 1 1 d . . . . .
N1 N 0.47401(12) 0.85751(5) 0.28644(5) 0.01261(16) Uani 1 1 d . . . . .
N2 N 0.68339(11) 0.98490(5) 0.29854(5) 0.01251(16) Uani 1 1 d . . . . .
C8 C 0.69364(13) 0.98052(6) 0.38575(6) 0.01183(17) Uani 1 1 d . . . . .
C9 C 0.62907(13) 0.90677(6) 0.41860(6) 0.01140(17) Uani 1 1 d . . . . .
C10 C 0.66181(14) 0.89745(6) 0.50377(6) 0.01392(18) Uani 1 1 d . . . . .
C1 C 0.52895(14) 0.84309(6) 0.37289(6) 0.01283(18) Uani 1 1 d . . . . .
C7 C 0.77152(14) 1.04297(6) 0.43448(6) 0.01526(19) Uani 1 1 d . . . . .
C5 C 0.74720(15) 0.96215(7) 0.55250(6) 0.0168(2) Uani 1 1 d . . . . .
C11 C 0.28101(15) 0.88440(7) 0.26939(7) 0.0187(2) Uani 1 1 d . . . . .
C4 C 0.60387(15) 0.82452(7) 0.53910(7) 0.0180(2) Uani 1 1 d . . . . .
C3 C 0.51166(17) 0.76394(7) 0.49270(7) 0.0206(2) Uani 1 1 d . . . . .
C6 C 0.79598(15) 1.03401(7) 0.51878(7) 0.0176(2) Uani 1 1 d . . . . .
C2 C 0.47094(16) 0.77383(7) 0.40864(7) 0.0185(2) Uani 1 1 d . . . . .
C14 C 0.85989(15) 0.95986(8) 0.27562(7) 0.0199(2) Uani 1 1 d . . . . .
C13 C 0.62460(17) 1.06607(7) 0.26327(7) 0.0202(2) Uani 1 1 d . . . . .
C12 C 0.5093(2) 0.78691(8) 0.23477(7) 0.0244(2) 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
O5 C15 1.3114(12) . ?
O1 C19 1.2361(12) . ?
O3 N3 1.2293(12) . ?
C18 C17 1.3836(14) . ?
C18 C20 1.3836(14) . ?
C18 N3 1.4702(13) . ?
C16 C17 1.3940(14) . ?
C16 C22 1.3982(14) . ?
C16 C15 1.5044(14) . ?
C21 C22 1.3931(14) . ?
C21 C20 1.3936(14) . ?
C21 C19 1.5184(14) . ?
O2 C19 1.2746(13) . ?
O4 N3 1.2304(12) . ?
O6 C15 1.2127(13) . ?
N1 C1 1.4682(13) . ?
N1 C12 1.4846(14) . ?
N1 C11 1.4852(14) . ?
N2 C8 1.4619(13) . ?
N2 C13 1.4778(14) . ?
N2 C14 1.4848(14) . ?
C8 C7 1.3704(14) . ?
C8 C9 1.4301(14) . ?
C9 C1 1.4233(14) . ?
C9 C10 1.4257(14) . ?
C10 C5 1.4162(15) . ?
C10 C4 1.4191(15) . ?
C1 C2 1.3738(14) . ?
C7 C6 1.4114(15) . ?
C5 C6 1.3679(16) . ?
C4 C3 1.3678(17) . ?
C3 C2 1.4102(16) . ?

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
C17 C18 C20 122.77(9) . . ?
C17 C18 N3 118.56(9) . . ?
C20 C18 N3 118.66(9) . . ?
C17 C16 C22 120.08(9) . . ?
C17 C16 C15 119.96(9) . . ?
C22 C16 C15 119.96(9) . . ?
C22 C21 C20 119.74(9) . . ?
C22 C21 C19 122.49(9) . . ?
C20 C21 C19 117.73(9) . . ?
C18 C20 C21 118.70(9) . . ?
O1 C19 O2 125.96(10) . . ?
O1 C19 C21 118.10(9) . . ?
O2 C19 C21 115.92(9) . . ?
C21 C22 C16 120.42(9) . . ?
C18 C17 C16 118.22(9) . . ?
O6 C15 O5 125.56(10) . . ?
O6 C15 C16 121.73(9) . . ?
O5 C15 C16 112.70(9) . . ?
O3 N3 O4 123.38(9) . . ?
O3 N3 C18 118.50(9) . . ?
O4 N3 C18 118.12(9) . . ?
C1 N1 C12 114.41(8) . . ?
C1 N1 C11 110.23(8) . . ?
C12 N1 C11 111.61(9) . . ?
C8 N2 C13 114.33(8) . . ?
C8 N2 C14 110.06(8) . . ?
C13 N2 C14 110.79(9) . . ?
C7 C8 C9 121.22(9) . . ?
C7 C8 N2 121.08(9) . . ?
C9 C8 N2 117.61(8) . . ?
C1 C9 C10 117.33(9) . . ?
C1 C9 C8 124.95(9) . . ?
C10 C9 C8 117.68(9) . . ?
C5 C10 C4 120.57(9) . . ?
C5 C10 C9 119.65(9) . . ?
C4 C10 C9 119.75(9) . . ?
C2 C1 C9 121.76(9) . . ?
C2 C1 N1 120.52(9) . . ?
C9 C1 N1 117.46(8) . . ?
C8 C7 C6 120.14(10) . . ?
C6 C5 C10 120.71(10) . . ?
C3 C4 C10 120.89(10) . . ?
C4 C3 C2 120.07(10) . . ?
C5 C6 C7 120.38(10) . . ?
C1 C2 C3 120.09(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H2 O6 0.966(15) 2.294(15) 3.1728(14) 150.9(12) 4_686
C13 H8 O1 0.960(15) 2.650(16) 3.5590(15) 158.0(12) .
C11 H15 O2 0.962(16) 2.368(17) 3.2847(14) 159.1(13) 2_545
C11 H14 O4 0.982(15) 2.538(15) 3.3734(15) 142.9(11) .
C14 H11 O1 0.981(15) 2.579(15) 3.4458(15) 147.3(12) 1_655
C12 H18 O4 0.968(18) 2.556(18) 3.3930(15) 144.8(13) .
N1 H1 N2 1.20(2) 1.43(2) 2.5716(12) 155.4(19) .
O5 H22 O2 0.99(2) 1.52(2) 2.4861(11) 166(2) 4_585

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.059


_exptl_crystal_recrystallization_method 
'slow evaporation from methanol solvent at 30 degreesC'
####################################################################### 
# 
# 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_complex_9
_database_code_depnum_ccdc_archive 'CCDC 1831641'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'DMAN 2-nitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N2, C7 H4 N1 O4'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 '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 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.3320(4)
_cell_length_b                   18.3951(7)
_cell_length_c                   10.3744(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.652(2)
_cell_angle_gamma                90
_cell_volume                     1916.03(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      41.11

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             808

_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_min  0.6771
_exptl_absorpt_correction_T_max  0.7481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction  
;

_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_detector                 'CMOS Detector'
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_reflns_number            34754
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.759
_diffrn_reflns_theta_max         41.120
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6559
_reflns_number_gt                4927
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0652P)²+0.3845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6559
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H20 H 0.4178(16) 0.2528(9) 0.1447(15) 0.025(4) Uiso 1 1 d . . . . .
H23 H 0.8865(16) 0.2798(8) 0.2446(15) 0.021(4) Uiso 1 1 d . . . . .
H22 H 0.7784(16) 0.1987(9) 0.0698(16) 0.029(4) Uiso 1 1 d . . . . .
H21 H 0.5425(15) 0.1861(9) 0.0258(16) 0.025(4) Uiso 1 1 d . . . . .
O1 O 0.89352(8) 0.38927(5) 0.39767(8) 0.01684(17) Uani 1 1 d . . . . .
O2 O 0.74601(9) 0.35633(5) 0.51516(8) 0.02116(19) Uani 1 1 d . . . . .
O4 O 0.42569(9) 0.30709(5) 0.39441(9) 0.0235(2) Uani 1 1 d . . . . .
O3 O 0.50226(9) 0.40882(5) 0.33862(9) 0.0234(2) Uani 1 1 d . . . . .
N3 N 0.49772(9) 0.34252(5) 0.33908(9) 0.01477(19) Uani 1 1 d . . . . .
C16 C 0.71745(11) 0.31170(6) 0.29711(10) 0.0122(2) Uani 1 1 d . . . . .
C15 C 0.79140(11) 0.35717(6) 0.41382(11) 0.0134(2) Uani 1 1 d . . . . .
C21 C 0.58031(11) 0.30192(6) 0.26553(11) 0.0129(2) Uani 1 1 d . . . . .
C17 C 0.78953(11) 0.27276(6) 0.22208(11) 0.0155(2) Uani 1 1 d . . . . .
C20 C 0.51418(12) 0.25631(7) 0.16512(11) 0.0170(2) Uani 1 1 d . . . . .
C18 C 0.72656(12) 0.22627(7) 0.12140(12) 0.0181(2) Uani 1 1 d . . . . .
C19 C 0.58923(12) 0.21794(7) 0.09288(12) 0.0190(2) Uani 1 1 d . . . . .
H14 H 0.5571(15) 0.3739(9) 0.6269(16) 0.025(4) Uiso 1 1 d . . . . .
H10 H 0.7825(15) 0.4949(9) 0.4860(15) 0.023(4) Uiso 1 1 d . . . . .
H12 H 0.9656(15) 0.4342(9) 0.6275(15) 0.020(4) Uiso 1 1 d . . . . .
H17 H 0.7532(16) 0.3098(9) 0.7399(16) 0.027(4) Uiso 1 1 d . . . . .
H8 H 0.6983(16) 0.5540(8) 0.5454(15) 0.020(4) Uiso 1 1 d . . . . .
H11 H 1.0319(15) 0.5077(9) 0.6945(14) 0.019(4) Uiso 1 1 d . . . . .
H5 H 0.7199(16) 0.5864(9) 1.1801(16) 0.026(4) Uiso 1 1 d . . . . .
H13 H 0.9957(15) 0.4444(8) 0.7900(16) 0.023(4) Uiso 1 1 d . . . . .
H2 H 0.9309(15) 0.6309(8) 0.7286(16) 0.023(4) Uiso 1 1 d . . . . .
H1 H 0.7768(17) 0.4565(10) 0.6980(17) 0.034(5) Uiso 1 1 d . . . . .
H6 H 0.6227(16) 0.4692(9) 1.1864(17) 0.029(4) Uiso 1 1 d . . . . .
H7 H 0.6116(16) 0.3895(9) 1.0077(16) 0.025(4) Uiso 1 1 d . . . . .
H9 H 0.8473(16) 0.5711(9) 0.5374(16) 0.028(4) Uiso 1 1 d . . . . .
H16 H 0.5171(16) 0.4480(9) 0.6819(16) 0.026(4) Uiso 1 1 d . . . . .
H4 H 0.8251(15) 0.6770(9) 1.0743(16) 0.025(4) Uiso 1 1 d . . . . .
H18 H 0.6973(17) 0.3070(9) 0.8708(17) 0.032(4) Uiso 1 1 d . . . . .
H3 H 0.9274(17) 0.7136(10) 0.9031(16) 0.033(4) Uiso 1 1 d . . . . .
H15 H 0.4946(17) 0.3745(9) 0.7582(17) 0.030(4) Uiso 1 1 d . . . . .
H19 H 0.8432(18) 0.3430(9) 0.8772(17) 0.035(5) Uiso 1 1 d . . . . .
N1 N 0.83388(9) 0.49988(5) 0.68414(9) 0.01209(17) Uani 1 1 d . . . . .
N2 N 0.69144(9) 0.40786(5) 0.78533(9) 0.01273(18) Uani 1 1 d . . . . .
C9 C 0.76404(10) 0.52581(6) 0.89391(10) 0.0122(2) Uani 1 1 d . . . . .
C8 C 0.70236(11) 0.45651(6) 0.89792(10) 0.0127(2) Uani 1 1 d . . . . .
C10 C 0.76616(11) 0.57498(6) 1.00163(11) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.82682(11) 0.54987(6) 0.79316(11) 0.0133(2) Uani 1 1 d . . . . .
C13 C 0.78497(13) 0.53306(7) 0.55015(11) 0.0166(2) Uani 1 1 d . . . . .
C14 C 0.97105(11) 0.46915(7) 0.70075(12) 0.0166(2) Uani 1 1 d . . . . .
C5 C 0.71243(12) 0.55271(7) 1.10874(11) 0.0175(2) Uani 1 1 d . . . . .
C6 C 0.65950(12) 0.48503(7) 1.11195(12) 0.0193(2) Uani 1 1 d . . . . .
C7 C 0.65370(12) 0.43684(7) 1.00522(12) 0.0172(2) Uani 1 1 d . . . . .
C4 C 0.82539(12) 0.64430(7) 1.00167(12) 0.0194(2) Uani 1 1 d . . . . .
C2 C 0.88682(13) 0.61646(7) 0.79776(12) 0.0195(2) Uani 1 1 d . . . . .
C11 C 0.55332(12) 0.40089(7) 0.70730(13) 0.0200(2) Uani 1 1 d . . . . .
C3 C 0.88446(14) 0.66481(7) 0.90266(13) 0.0227(3) Uani 1 1 d . . . . .
C12 C 0.75102(15) 0.33605(7) 0.82220(13) 0.0222(3) 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 C15 1.2543(13) . ?
O2 C15 1.2483(13) . ?
O4 N3 1.2289(12) . ?
O3 N3 1.2206(13) . ?
N3 C21 1.4750(14) . ?
C16 C21 1.3887(15) . ?
C16 C17 1.3954(15) . ?
C16 C15 1.5207(15) . ?
C21 C20 1.3856(16) . ?
C17 C18 1.3874(16) . ?
C17 H23 0.982(16) . ?
C20 C19 1.3912(17) . ?
C20 H20 0.970(16) . ?
C18 C19 1.3878(17) . ?
C18 H22 0.983(16) . ?
C19 H21 0.950(16) . ?
N1 C1 1.4727(14) . ?
N1 C13 1.4928(14) . ?
N1 C14 1.4976(14) . ?
N1 H1 1.022(17) . ?
N2 C8 1.4546(14) . ?
N2 C12 1.4695(15) . ?
N2 C11 1.4707(15) . ?
C9 C1 1.4245(15) . ?
C9 C8 1.4301(15) . ?
C9 C10 1.4339(15) . ?
C8 C7 1.3737(15) . ?
C10 C4 1.4143(17) . ?
C10 C5 1.4149(16) . ?
C1 C2 1.3686(16) . ?
C13 H10 0.963(16) . ?
C13 H8 0.965(16) . ?
C13 H9 0.981(17) . ?
C14 H12 0.986(16) . ?
C14 H11 0.960(15) . ?
C14 H13 1.009(16) . ?
C5 C6 1.3633(18) . ?
C5 H5 0.954(17) . ?
C6 C7 1.4086(17) . ?
C6 H6 0.982(17) . ?
C7 H7 0.976(16) . ?
C4 C3 1.3659(18) . ?
C4 H4 0.964(16) . ?
C2 C3 1.4101(17) . ?
C2 H2 0.974(16) . ?
C11 H14 0.979(16) . ?
C11 H16 0.956(17) . ?
C11 H15 1.017(17) . ?
C3 H3 1.001(18) . ?
C12 H17 0.986(16) . ?
C12 H18 0.990(17) . ?
C12 H19 0.996(18) . ?

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
O3 N3 O4 124.05(10) . . ?
O3 N3 C21 118.46(9) . . ?
O4 N3 C21 117.46(9) . . ?
C21 C16 C17 116.81(10) . . ?
C21 C16 C15 123.51(10) . . ?
C17 C16 C15 119.50(10) . . ?
O2 C15 O1 127.84(10) . . ?
O2 C15 C16 116.47(10) . . ?
O1 C15 C16 115.65(9) . . ?
C20 C21 C16 123.40(10) . . ?
C20 C21 N3 116.92(10) . . ?
C16 C21 N3 119.67(10) . . ?
C18 C17 C16 121.28(11) . . ?
C18 C17 H23 122.1(9) . . ?
C16 C17 H23 116.6(9) . . ?
C21 C20 C19 118.26(11) . . ?
C21 C20 H20 120.2(9) . . ?
C19 C20 H20 121.5(9) . . ?
C17 C18 C19 120.18(11) . . ?
C17 C18 H22 120.6(10) . . ?
C19 C18 H22 119.2(10) . . ?
C18 C19 C20 120.06(11) . . ?
C18 C19 H21 122.8(9) . . ?
C20 C19 H21 117.1(9) . . ?
C1 N1 C13 113.12(9) . . ?
C1 N1 C14 111.37(9) . . ?
C13 N1 C14 111.39(9) . . ?
C1 N1 H1 104.1(10) . . ?
C13 N1 H1 111.8(10) . . ?
C14 N1 H1 104.5(10) . . ?
C8 N2 C12 113.31(9) . . ?
C8 N2 C11 112.15(9) . . ?
C12 N2 C11 110.94(10) . . ?
C1 C9 C8 125.55(10) . . ?
C1 C9 C10 116.75(10) . . ?
C8 C9 C10 117.68(10) . . ?
C7 C8 C9 120.61(10) . . ?
C7 C8 N2 120.98(10) . . ?
C9 C8 N2 118.41(9) . . ?
C4 C10 C5 120.72(11) . . ?
C4 C10 C9 119.73(10) . . ?
C5 C10 C9 119.52(11) . . ?
C2 C1 C9 122.24(10) . . ?
C2 C1 N1 118.78(10) . . ?
C9 C1 N1 118.90(9) . . ?
N1 C13 H10 107.0(9) . . ?
N1 C13 H8 108.4(9) . . ?
H10 C13 H8 112.4(13) . . ?
N1 C13 H9 109.2(10) . . ?
H10 C13 H9 109.8(13) . . ?
H8 C13 H9 109.9(13) . . ?
N1 C14 H12 106.0(9) . . ?
N1 C14 H11 109.3(9) . . ?
H12 C14 H11 110.4(12) . . ?
N1 C14 H13 107.6(9) . . ?
H12 C14 H13 111.7(12) . . ?
H11 C14 H13 111.6(13) . . ?
C6 C5 C10 121.17(11) . . ?
C6 C5 H5 122.2(10) . . ?
C10 C5 H5 116.5(10) . . ?
C5 C6 C7 119.90(11) . . ?
C5 C6 H6 121.5(10) . . ?
C7 C6 H6 118.6(10) . . ?
C8 C7 C6 121.02(11) . . ?
C8 C7 H7 120.5(9) . . ?
C6 C7 H7 118.5(9) . . ?
C3 C4 C10 121.26(11) . . ?
C3 C4 H4 119.9(10) . . ?
C10 C4 H4 118.8(9) . . ?
C1 C2 C3 120.08(11) . . ?
C1 C2 H2 120.3(9) . . ?
C3 C2 H2 119.6(9) . . ?
N2 C11 H14 106.6(9) . . ?
N2 C11 H16 109.8(10) . . ?
H14 C11 H16 108.4(13) . . ?
N2 C11 H15 112.1(10) . . ?
H14 C11 H15 110.4(14) . . ?
H16 C11 H15 109.5(13) . . ?
C4 C3 C2 119.89(12) . . ?
C4 C3 H3 121.3(9) . . ?
C2 C3 H3 118.8(10) . . ?
N2 C12 H17 108.0(9) . . ?
N2 C12 H18 111.5(10) . . ?
H17 C12 H18 107.9(14) . . ?
N2 C12 H19 108.6(10) . . ?
H17 C12 H19 110.2(14) . . ?
H18 C12 H19 110.6(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H14 O2 0.979(16) 2.515(16) 3.2376(15) 130.5(12) .
C13 H10 O1 0.963(16) 2.536(16) 3.4051(15) 150.2(12) .
C13 H10 O2 0.963(16) 2.605(16) 3.2854(16) 127.9(12) .
C14 H12 O1 0.986(16) 2.467(16) 3.3910(15) 155.9(12) .
C12 H17 O2 0.986(16) 2.469(16) 3.1954(16) 130.3(12) .
C14 H11 O1 0.960(15) 2.335(15) 3.2340(15) 155.8(12) 3_766
C2 H2 O1 0.974(16) 2.503(15) 3.3830(15) 150.3(13) 3_766
N1 H1 O2 1.022(17) 2.610(17) 3.1811(13) 115.1(11) .
N1 H1 N2 1.022(17) 1.666(17) 2.6196(13) 153.2(15) .
C11 H16 O3 0.956(17) 2.646(17) 3.5609(16) 160.3(13) 3_666

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.059


_exptl_crystal_recrystallization_method 
'slow evaporation from methanol at 30 degreesC'
####################################################################### 
# 
# 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_complex_3
_database_code_depnum_ccdc_archive 'CCDC 1831644'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT353_complex_3           
;
PROBLEM: Long    N-H (N0.87,N1.01A)  N1     -   H1A    ..       1.30 Ang.  
RESPONSE: H1A is in a short strong N-H...N hydrogen bond.
;
_vrf_PLAT355_complex_3           
;
PROBLEM: Long    O-H (X0.82,N0.98A)  O2     -   H90    ..       1.20 Ang.  
RESPONSE: H90 is in a short strong O-H...O hydrogen bond.
;
_vrf_PLAT415_complex_3           
;
PROBLEM: Short Inter D-H..H-X       H42A   ..  H101    ..       1.81 Ang.  
RESPONSE: H101 is modelled onto a water molecule that is 
likely disordered/on a partially occupied site.
;
_vrf_PLAT245_complex_3           
;
PROBLEM: U(iso) H27     Smaller than U(eq) O15     by ...      0.077 AngSq 
RESPONSE: H27 is modelled onto a water molecule that is 
likely disordered/on a partially occupied site.
;
_vrf_PLAT417_complex_3           
;
PROBLEM: Short Inter D-H..H-D       H92    ..  H93     ..       2.07 Ang.  
RESPONSE: H92 and H93 are modelled onto a water molecule that is likely 
disordered/on a partially occupied site.
;
_vrf_PLAT420_complex_3           
;
PROBLEM: D-H Without Acceptor       O15    --  H27    ...     Please Check 
RESPONSE: O15-H27 are part of a water molecule that is likely 
disordered/on a partially occupied site.
;
_vrf_PLAT910_complex_3           
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          33 Note  
RESPONSE: May be caused by overloads at low angle and 
so excluded during the data reduction.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'DMAN 4-amino benzoic acid 4-aminobenzoate hydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'3(C14 H19 N2), 2(C7 H6 N1 O2), 4(C6 H7 N1 O2), 4(H2 O)'
_chemical_formula_sum            'C84 H104 N12 O16'
_chemical_formula_weight         1537.79

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.3902(6)
_cell_length_b                   17.4977(7)
_cell_length_c                   19.3081(9)
_cell_angle_alpha                85.639(4)
_cell_angle_beta                 70.634(4)
_cell_angle_gamma                69.986(4)
_cell_volume                     4006.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4978
_cell_measurement_theta_min      3.487
_cell_measurement_theta_max      27.079
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             1640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_correction_T_min  0.95024
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
        (compiled Mar 27 2014,17:12:48)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 16.1468
_diffrn_reflns_number            41896
_diffrn_reflns_av_unetI/netI     0.1400
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.270
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             17701
_reflns_number_gt                7611
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
        (compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
        (compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
        (compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-2013(Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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 > 2σ(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.

For all DMAN methyl groups, H-atoms were placed geometrically using HFIX 33.

For the water molecules, the H-atoms of O13 - O15 (H91, H92, H27, H88, H93, H99) 
were located from Fourier difference maps  whilst their isotropic
displacement parameters were refined fixed at 1.5 that of the preceeding normal atom.
For water molecule O16, the H-atoms H100 and H101 were geometrically placed based on the coordinates of
O16 and refined with O-H distances restrained to 0.82 using DFIX and OHO angle restraint
 using DANG 1.6 H101 H100.

The water molecules are likely disordered or not fully occupying their sites.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0765P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         17701
_refine_ls_number_parameters     1271
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1953
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2161
_refine_ls_wR_factor_gt          0.1590
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O13 O -0.3440(3) -0.4775(2) 1.35079(18) 0.0649(10) Uani 1 1 d . . . . .
O14 O -0.2456(3) -0.53837(19) 1.20161(16) 0.0598(9) Uani 1 1 d . . . . .
O15 O 0.5577(4) 0.3276(3) 0.1275(4) 0.133(2) Uani 1 1 d . . . . .
O16 O 0.2878(6) -0.2244(3) 0.8229(3) 0.150(2) Uani 1 1 d D . . . .
H100 H 0.315(8) -0.189(5) 0.791(3) 0.225 Uiso 1 1 d D U . . .
H101 H 0.280(8) -0.222(5) 0.8719(15) 0.225 Uiso 1 1 d D U . . .
H4 H -0.245(3) 0.2188(18) 0.4125(15) 0.022(9) Uiso 1 1 d . . . . .
H14 H 0.235(3) 0.173(2) 0.3440(16) 0.035(10) Uiso 1 1 d . . . . .
H9 H -0.450(2) -0.3973(17) 1.4658(15) 0.013(8) Uiso 1 1 d . . . . .
H15 H 0.221(3) 0.0643(18) 0.4317(16) 0.023(9) Uiso 1 1 d . . . . .
H11 H 0.127(3) -0.1006(18) 0.7544(15) 0.021(8) Uiso 1 1 d . . . . .
H5 H -0.203(3) -0.3852(19) 1.0625(15) 0.027(9) Uiso 1 1 d . . . . .
H18 H 0.086(3) 0.1265(19) 0.3579(15) 0.022(9) Uiso 1 1 d . . . . .
H7 H -0.043(2) -0.1776(17) 1.0429(14) 0.013(8) Uiso 1 1 d . . . . .
H12 H 0.155(3) 0.087(2) 0.8427(17) 0.034(10) Uiso 1 1 d . . . . .
H1 H 0.410(3) 0.436(2) 0.0547(16) 0.032(10) Uiso 1 1 d . . . . .
H16 H 0.579(3) 0.064(2) 0.2810(17) 0.033(10) Uiso 1 1 d . . . . .
H13 H 0.229(3) 0.1385(19) 0.7297(15) 0.025(9) Uiso 1 1 d . . . . .
H3 H -0.092(3) 0.745(2) 0.5630(17) 0.034(10) Uiso 1 1 d . . . . .
H17 H 0.111(3) 0.221(2) 0.2687(18) 0.040(11) Uiso 1 1 d . . . . .
H2 H 0.401(3) 0.5356(19) -0.0367(16) 0.026(9) Uiso 1 1 d . . . . .
H10 H 0.204(3) -0.056(2) 0.6369(17) 0.033(10) Uiso 1 1 d . . . . .
H6 H -0.108(3) -0.3445(19) 0.9472(17) 0.028(10) Uiso 1 1 d . . . . .
H8 H -0.531(3) -0.439(2) 1.5789(17) 0.036(10) Uiso 1 1 d . . . . .
H27 H 0.518(4) 0.393(3) 0.149(2) 0.055 Uiso 1 1 d . U . . .
H19 H -0.217(3) 0.780(2) 0.4929(18) 0.041(11) Uiso 1 1 d . . . . .
H31 H 0.417(3) 0.124(2) -0.2103(18) 0.049(11) Uiso 1 1 d . . . . .
H20 H 0.837(3) -0.035(2) -0.0533(17) 0.034(11) Uiso 1 1 d . . . . .
H23 H 0.289(3) 0.0404(19) 0.5665(16) 0.013(9) Uiso 1 1 d . . . . .
H30 H 0.062(3) 0.4949(18) 0.1118(15) 0.025(9) Uiso 1 1 d . . . . .
H21 H 0.886(3) -0.101(2) -0.1629(18) 0.038(11) Uiso 1 1 d . . . . .
H22 H 0.290(4) 0.109(3) 0.598(2) 0.055(14) Uiso 1 1 d . . . . .
H34 H 0.028(4) -0.203(3) 0.903(2) 0.072(15) Uiso 1 1 d . . . . .
H29 H 0.550(3) 0.550(2) 0.1664(19) 0.051(12) Uiso 1 1 d . . . . .
H50 H 0.560(3) -0.0355(19) 0.3661(15) 0.021(9) Uiso 1 1 d . . . . .
H47 H 0.767(3) -0.068(2) -0.2291(18) 0.037(11) Uiso 1 1 d . . . . .
H37 H -0.231(3) 0.319(2) 0.3206(16) 0.029(9) Uiso 1 1 d . . . . .
H43 H 0.251(3) 0.679(2) 0.0814(18) 0.039(10) Uiso 1 1 d . . . . .
H38 H -0.108(4) 0.376(2) 0.2327(19) 0.046(13) Uiso 1 1 d . . . . .
H39 H -0.165(3) 0.7028(19) 0.3837(16) 0.026(10) Uiso 1 1 d . . . . .
H48 H 0.365(3) 0.196(2) -0.0961(16) 0.033(10) Uiso 1 1 d . . . . .
H42 H 0.299(4) 0.652(2) -0.089(2) 0.063(14) Uiso 1 1 d . . . . .
H46 H 0.592(3) 0.016(2) -0.2463(19) 0.045(12) Uiso 1 1 d . . . . .
H40 H 0.036(3) 0.871(2) 0.2349(17) 0.040(11) Uiso 1 1 d . . . . .
H51 H 0.440(3) -0.096(2) 0.4612(17) 0.034(11) Uiso 1 1 d . . . . .
H103 H 0.315(3) -0.0579(19) 0.4772(17) 0.022(10) Uiso 1 1 d . . . . .
H55 H 0.250(4) 0.540(2) 0.549(2) 0.071(14) Uiso 1 1 d . . . . .
H52 H -0.149(3) -0.215(2) 1.1575(18) 0.043(11) Uiso 1 1 d . . . . .
H61 H 0.077(3) 0.797(2) 0.1244(18) 0.040(11) Uiso 1 1 d . . . . .
H56 H 0.299(4) 0.465(2) 0.4425(19) 0.058(13) Uiso 1 1 d . . . . .
H64 H 0.074(3) 0.588(2) 0.0210(18) 0.041(12) Uiso 1 1 d . . . . .
H53 H 0.011(4) -0.268(3) 0.877(2) 0.060(16) Uiso 1 1 d . . . . .
H71 H -0.603(3) -0.404(2) 1.7095(17) 0.016(11) Uiso 1 1 d . . . . .
H74 H 0.076(3) 0.656(2) 0.580(2) 0.049(12) Uiso 1 1 d . . . . .
H69 H 0.422(3) 0.590(2) 0.092(2) 0.061(12) Uiso 1 1 d . . . . .
H68 H 0.019(4) 0.348(2) 0.2167(19) 0.044(12) Uiso 1 1 d . . . . .
H70 H -0.453(3) -0.191(2) 1.5574(17) 0.038(10) Uiso 1 1 d . . . . .
H78 H 0.175(4) 0.673(2) -0.0682(19) 0.047(13) Uiso 1 1 d . . . . .
H80 H 0.507(4) 0.624(2) 0.2761(19) 0.057(13) Uiso 1 1 d . . . . .
H83 H -0.541(3) -0.230(2) 1.681(2) 0.068(13) Uiso 1 1 d . . . . .
H88 H 0.496(5) 0.351(4) 0.142(3) 0.102 Uiso 1 1 d . U . . .
H92 H -0.302(4) -0.494(3) 1.292(3) 0.102 Uiso 1 1 d . U . . .
H1A H 0.108(3) 0.5243(19) 0.3179(15) 0.025(9) Uiso 1 1 d . . . . .
H1B H 0.222(4) 0.799(2) 0.3477(19) 0.056(12) Uiso 1 1 d . . . . .
H96 H 0.338(3) 0.283(2) 0.207(2) 0.060(13) Uiso 1 1 d . . . . .
H90 H -0.316(4) -0.286(2) 1.308(2) 0.075(14) Uiso 1 1 d . . . . .
H1C H 0.571(4) 0.127(3) 0.020(2) 0.075(14) Uiso 1 1 d . . . . .
H94 H 0.000000 0.000000 0.500000 0.08(2) Uiso 1 2 d S . P . .
H91 H -0.348(5) -0.416(4) 1.348(3) 0.121 Uiso 1 1 d . U . . .
H95 H 0.000000 0.000000 1.000000 0.10(2) Uiso 1 2 d S . P . .
H93 H -0.241(5) -0.471(4) 1.182(3) 0.157 Uiso 1 1 d . U . . .
H97 H -0.612(5) -0.340(4) 1.744(3) 0.11(3) Uiso 1 1 d . . . . .
H99 H -0.251(6) -0.565(4) 1.156(3) 0.169 Uiso 1 1 d . U . . .
C10 C 0.0573(3) 0.6003(2) 0.42771(17) 0.0249(8) Uani 1 1 d . . . . .
N2 N 0.0135(3) 0.57925(18) 0.31700(14) 0.0280(7) Uani 1 1 d . . . . .
N1 N 0.1926(3) 0.48607(17) 0.34098(15) 0.0289(7) Uani 1 1 d . . . . .
C8 C -0.1166(3) 0.6887(2) 0.4097(2) 0.0310(9) Uani 1 1 d . . . . .
C5 C 0.0258(3) 0.6474(2) 0.49384(18) 0.0282(8) Uani 1 1 d . . . . .
C1 C 0.1595(3) 0.5332(2) 0.40928(19) 0.0286(8) Uani 1 1 d . . . . .
C9 C -0.0193(3) 0.6249(2) 0.38622(18) 0.0266(8) Uani 1 1 d . . . . .
C7 C -0.1467(4) 0.7334(2) 0.4750(2) 0.0320(9) Uani 1 1 d . . . . .
C2 C 0.2253(4) 0.5128(3) 0.4538(2) 0.0364(10) Uani 1 1 d . . . . .
C6 C -0.0761(3) 0.7138(2) 0.5155(2) 0.0331(9) Uani 1 1 d . . . . .
C4 C 0.0975(4) 0.6252(3) 0.5374(2) 0.0362(10) Uani 1 1 d . . . . .
C3 C 0.1935(4) 0.5596(3) 0.5186(2) 0.0393(10) Uani 1 1 d . . . . .
C12 C 0.2973(3) 0.4935(2) 0.28678(19) 0.0415(10) Uani 1 1 d . . . . .
H12A H 0.288793 0.550037 0.279952 0.062 Uiso 1 1 calc R U . . .
H12B H 0.359266 0.467655 0.304612 0.062 Uiso 1 1 calc R U . . .
H12C H 0.311317 0.467680 0.240747 0.062 Uiso 1 1 calc R U . . .
C11 C 0.2010(4) 0.4009(2) 0.3534(2) 0.0468(11) Uani 1 1 d . . . . .
H11A H 0.222857 0.372709 0.307207 0.070 Uiso 1 1 calc R U . . .
H11B H 0.256273 0.375922 0.377167 0.070 Uiso 1 1 calc R U . . .
H11C H 0.129420 0.398317 0.384141 0.070 Uiso 1 1 calc R U . . .
C14 C 0.0349(3) 0.6309(2) 0.25312(18) 0.0390(10) Uani 1 1 d . . . . .
H14A H 0.056113 0.599601 0.208639 0.058 Uiso 1 1 calc R U . . .
H14B H -0.032063 0.676608 0.257196 0.058 Uiso 1 1 calc R U . . .
H14C H 0.094565 0.650008 0.252111 0.058 Uiso 1 1 calc R U . . .
C13 C -0.0676(3) 0.5404(2) 0.3154(2) 0.0416(10) Uani 1 1 d . . . . .
H13A H -0.041954 0.511562 0.269011 0.062 Uiso 1 1 calc R U . . .
H13B H -0.074088 0.503027 0.354329 0.062 Uiso 1 1 calc R U . . .
H13C H -0.139709 0.581443 0.321840 0.062 Uiso 1 1 calc R U . . .
N4 N 0.1422(3) 0.84154(18) 0.32833(15) 0.0284(7) Uani 1 1 d . . . . .
C28 C 0.2744(3) 0.7310(2) 0.23607(17) 0.0228(8) Uani 1 1 d . . . . .
N3 N 0.3267(3) 0.74674(18) 0.34431(15) 0.0297(7) Uani 1 1 d . . . . .
C23 C 0.3017(3) 0.6881(2) 0.16886(18) 0.0306(9) Uani 1 1 d . . . . .
C19 C 0.3535(3) 0.7037(2) 0.27510(18) 0.0269(8) Uani 1 1 d . . . . .
C27 C 0.1729(3) 0.7978(2) 0.25808(18) 0.0276(8) Uani 1 1 d . . . . .
C26 C 0.1040(3) 0.8223(3) 0.2161(2) 0.0368(10) Uani 1 1 d . . . . .
C20 C 0.4513(3) 0.6402(2) 0.2490(2) 0.0365(10) Uani 1 1 d . . . . .
C21 C 0.4768(4) 0.5986(3) 0.1822(2) 0.0413(10) Uani 1 1 d . . . . .
C22 C 0.4030(4) 0.6217(2) 0.1436(2) 0.0369(10) Uani 1 1 d . . . . .
C24 C 0.2263(4) 0.7136(3) 0.1272(2) 0.0393(10) Uani 1 1 d . . . . .
C25 C 0.1319(4) 0.7793(3) 0.1503(2) 0.0445(11) Uani 1 1 d . . . . .
C15 C 0.0388(3) 0.8319(2) 0.38231(18) 0.0377(10) Uani 1 1 d . . . . .
H15A H 0.047344 0.775090 0.386030 0.057 Uiso 1 1 calc R U . . .
H15B H 0.026743 0.854203 0.429470 0.057 Uiso 1 1 calc R U . . .
H15C H -0.024512 0.860020 0.366298 0.057 Uiso 1 1 calc R U . . .
C18 C 0.3169(4) 0.6935(3) 0.40737(18) 0.0507(12) Uani 1 1 d . . . . .
H18A H 0.299276 0.724461 0.451429 0.076 Uiso 1 1 calc R U . . .
H18B H 0.258123 0.671910 0.412068 0.076 Uiso 1 1 calc R U . . .
H18C H 0.386761 0.649624 0.399696 0.076 Uiso 1 1 calc R U . . .
C16 C 0.1345(4) 0.9275(2) 0.3200(2) 0.0509(12) Uani 1 1 d . . . . .
H16A H 0.114292 0.952638 0.367474 0.076 Uiso 1 1 calc R U . . .
H16B H 0.205867 0.930669 0.289533 0.076 Uiso 1 1 calc R U . . .
H16C H 0.078287 0.955183 0.297678 0.076 Uiso 1 1 calc R U . . .
C17 C 0.4064(4) 0.7901(3) 0.3396(2) 0.0530(12) Uani 1 1 d . . . . .
H17A H 0.386247 0.817621 0.385967 0.079 Uiso 1 1 calc R U . . .
H17B H 0.481333 0.751593 0.327857 0.079 Uiso 1 1 calc R U . . .
H17C H 0.403198 0.829179 0.302013 0.079 Uiso 1 1 calc R U . . .
N6 N 0.6604(3) 0.08477(18) 0.01622(15) 0.0304(7) Uani 1 1 d . . . . .
N5 N 0.4732(3) 0.17356(17) -0.00056(15) 0.0282(7) Uani 1 1 d . . . . .
C40 C 0.6112(3) 0.0665(2) -0.09328(17) 0.0255(8) Uani 1 1 d . . . . .
C35 C 0.6423(3) 0.0233(2) -0.16125(17) 0.0278(8) Uani 1 1 d . . . . .
C31 C 0.5060(3) 0.1298(2) -0.07037(18) 0.0273(8) Uani 1 1 d . . . . .
C32 C 0.4360(4) 0.1497(2) -0.1121(2) 0.0336(9) Uani 1 1 d . . . . .
C39 C 0.6908(3) 0.0422(2) -0.05440(17) 0.0263(8) Uani 1 1 d . . . . .
C38 C 0.7912(3) -0.0184(2) -0.0807(2) 0.0328(9) Uani 1 1 d . . . . .
C37 C 0.8200(4) -0.0602(3) -0.1476(2) 0.0375(10) Uani 1 1 d . . . . .
C36 C 0.7467(3) -0.0396(2) -0.1863(2) 0.0338(10) Uani 1 1 d . . . . .
C33 C 0.4679(4) 0.1081(2) -0.1790(2) 0.0376(10) Uani 1 1 d . . . . .
C34 C 0.5675(4) 0.0464(2) -0.2029(2) 0.0355(10) Uani 1 1 d . . . . .
C42 C 0.7350(4) 0.1320(2) 0.0145(2) 0.0468(11) Uani 1 1 d . . . . .
H42A H 0.711845 0.158538 0.061737 0.070 Uiso 1 1 calc R U . . .
H42B H 0.811269 0.095711 0.002865 0.070 Uiso 1 1 calc R U . . .
H42C H 0.730000 0.172076 -0.022134 0.070 Uiso 1 1 calc R U . . .
C30 C 0.4619(4) 0.2606(2) -0.0115(2) 0.0449(11) Uani 1 1 d . . . . .
H30A H 0.440364 0.287871 0.035148 0.067 Uiso 1 1 calc R U . . .
H30B H 0.532576 0.264709 -0.042475 0.067 Uiso 1 1 calc R U . . .
H30C H 0.405557 0.285654 -0.034405 0.067 Uiso 1 1 calc R U . . .
C29 C 0.3702(3) 0.1650(2) 0.05424(18) 0.0385(10) Uani 1 1 d . . . . .
H29A H 0.352879 0.194892 0.098811 0.058 Uiso 1 1 calc R U . . .
H29B H 0.308700 0.185909 0.035207 0.058 Uiso 1 1 calc R U . . .
H29C H 0.382335 0.108496 0.064223 0.058 Uiso 1 1 calc R U . . .
C41 C 0.6526(4) 0.0292(2) 0.07812(18) 0.0446(11) Uani 1 1 d . . . . .
H41A H 0.632606 0.059173 0.123137 0.067 Uiso 1 1 calc R U . . .
H41B H 0.596141 0.005710 0.081241 0.067 Uiso 1 1 calc R U . . .
H41C H 0.723832 -0.013316 0.070078 0.067 Uiso 1 1 calc R U . . .
C43D C -0.3941(3) -0.2626(2) 1.42602(18) 0.0263(8) Uani 1 1 d . . . . .
O1 O -0.3548(2) -0.31514(14) 1.37195(12) 0.0318(6) Uani 1 1 d . . . . .
O6 O -0.3885(2) -0.19287(15) 1.41899(12) 0.0335(6) Uani 1 1 d . . . . .
C44 C -0.4461(3) -0.2906(2) 1.49984(17) 0.0263(8) Uani 1 1 d . . . . .
C45 C -0.4714(3) -0.2440(2) 1.56297(19) 0.0364(10) Uani 1 1 d . . . . .
C46 C -0.5169(4) -0.2702(3) 1.6320(2) 0.0418(11) Uani 1 1 d . . . . .
C47 C -0.5389(3) -0.3425(2) 1.64071(19) 0.0341(10) Uani 1 1 d . . . . .
C48 C -0.5162(3) -0.3889(2) 1.57786(19) 0.0311(9) Uani 1 1 d . . . . .
C49 C -0.4704(3) -0.3625(2) 1.5090(2) 0.0299(9) Uani 1 1 d . . . . .
N7 N -0.5784(4) -0.3706(3) 1.7098(2) 0.0496(11) Uani 1 1 d . . . . .
O2 O -0.2587(2) -0.27509(15) 1.24845(13) 0.0342(7) Uani 1 1 d . . . . .
O3 O -0.2833(2) -0.37830(16) 1.20387(13) 0.0437(7) Uani 1 1 d . . . . .
C50E C -0.2448(3) -0.3227(2) 1.19413(19) 0.0304(9) Uani 1 1 d . . . . .
C51 C -0.1820(3) -0.3026(2) 1.12012(17) 0.0242(8) Uani 1 1 d . . . . .
C52 C -0.1340(3) -0.2421(2) 1.1123(2) 0.0287(9) Uani 1 1 d . . . . .
C53 C -0.0782(3) -0.2206(2) 1.04373(18) 0.0295(9) Uani 1 1 d . . . . .
C54 C -0.0675(3) -0.2604(2) 0.98015(18) 0.0251(8) Uani 1 1 d . . . . .
C55 C -0.1177(3) -0.3205(2) 0.98859(19) 0.0259(8) Uani 1 1 d . . . . .
C56 C -0.1722(3) -0.3417(2) 1.05657(19) 0.0266(8) Uani 1 1 d . . . . .
N8 N -0.0053(3) -0.2431(2) 0.91349(18) 0.0384(9) Uani 1 1 d . . . . .
O5 O 0.0459(2) 0.01931(14) 0.93751(11) 0.0320(6) Uani 1 1 d . . . . .
O4 O 0.0674(2) -0.10157(15) 0.89314(12) 0.0376(7) Uani 1 1 d . . . . .
C57F C 0.0779(3) -0.0340(2) 0.88431(17) 0.0252(8) Uani 1 1 d . . . . .
C58 C 0.1300(3) -0.00748(19) 0.80949(17) 0.0219(8) Uani 1 1 d . . . . .
C59 C 0.1610(3) 0.0610(2) 0.80092(18) 0.0251(8) Uani 1 1 d . . . . .
C60 C 0.2053(3) 0.0887(2) 0.73265(17) 0.0235(8) Uani 1 1 d . . . . .
C61 C 0.2200(3) 0.0467(2) 0.66903(17) 0.0227(8) Uani 1 1 d . . . . .
C62 C 0.1904(3) -0.0238(2) 0.67785(18) 0.0277(9) Uani 1 1 d . . . . .
C63 C 0.1471(3) -0.0506(2) 0.74614(17) 0.0248(8) Uani 1 1 d . . . . .
N9 N 0.2580(3) 0.0759(2) 0.60069(17) 0.0297(8) Uani 1 1 d . . . . .
O8 O 0.0019(2) 0.05650(14) 0.45864(12) 0.0338(6) Uani 1 1 d . . . . .
O7 O -0.1854(2) 0.10830(15) 0.49756(13) 0.0384(7) Uani 1 1 d . . . . .
C64G C -0.0924(3) 0.1066(2) 0.45512(17) 0.0240(8) Uani 1 1 d . . . . .
C65 C -0.0819(3) 0.1655(2) 0.39512(16) 0.0217(8) Uani 1 1 d . . . . .
C66 C -0.1758(3) 0.2223(2) 0.38285(19) 0.0280(9) Uani 1 1 d . . . . .
C67 C -0.1642(3) 0.2775(2) 0.32906(18) 0.0295(9) Uani 1 1 d . . . . .
C68 C -0.0582(3) 0.2801(2) 0.28589(17) 0.0244(8) Uani 1 1 d . . . . .
C69 C 0.0359(3) 0.2227(2) 0.29777(18) 0.0234(8) Uani 1 1 d . . . . .
C70 C 0.0237(3) 0.1668(2) 0.35093(17) 0.0246(8) Uani 1 1 d . . . . .
N11 N -0.0453(3) 0.3360(2) 0.23164(16) 0.0304(8) Uani 1 1 d . . . . .
O12 O 0.3238(2) 0.23781(15) 0.24096(12) 0.0323(6) Uani 1 1 d . . . . .
O11 O 0.5116(2) 0.18705(15) 0.20083(13) 0.0390(7) Uani 1 1 d . . . . .
C71H C 0.4203(3) 0.1860(2) 0.24358(18) 0.0262(8) Uani 1 1 d . . . . .
C72 C 0.4090(3) 0.1265(2) 0.30180(16) 0.0233(8) Uani 1 1 d . . . . .
C73 C 0.3040(3) 0.1268(2) 0.34784(17) 0.0237(8) Uani 1 1 d . . . . .
C74 C 0.2923(3) 0.0687(2) 0.39911(18) 0.0255(8) Uani 1 1 d . . . . .
C75 C 0.3886(3) 0.0076(2) 0.40662(17) 0.0258(8) Uani 1 1 d . . . . .
C76 C 0.4941(3) 0.0084(2) 0.36100(19) 0.0300(9) Uani 1 1 d . . . . .
C77 C 0.5044(3) 0.0668(2) 0.3096(2) 0.0312(9) Uani 1 1 d . . . . .
N10 N 0.3795(3) -0.0499(2) 0.45989(16) 0.0282(7) Uani 1 1 d . . . . .
O10 O 0.3336(2) 0.35120(14) 0.15413(12) 0.0315(6) Uani 1 1 d . . . . .
O9 O 0.1464(2) 0.39320(16) 0.19071(14) 0.0465(7) Uani 1 1 d . . . . .
C78I C 0.2377(3) 0.3970(2) 0.14922(18) 0.0272(8) Uani 1 1 d . . . . .
C79 C 0.2396(3) 0.4577(2) 0.09036(17) 0.0241(8) Uani 1 1 d . . . . .
C80 C 0.1389(3) 0.5043(2) 0.07837(19) 0.0284(8) Uani 1 1 d . . . . .
C81 C 0.1388(4) 0.5604(2) 0.0245(2) 0.0342(10) Uani 1 1 d . . . . .
C82 C 0.2377(3) 0.5726(2) -0.01949(17) 0.0291(9) Uani 1 1 d . . . . .
C83 C 0.3378(3) 0.5256(2) -0.00767(19) 0.0271(8) Uani 1 1 d . . . . .
C84 C 0.3383(3) 0.4692(2) 0.04619(18) 0.0255(8) Uani 1 1 d . . . . .
N12 N 0.2379(4) 0.6267(2) -0.07675(17) 0.0381(9) 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
C10 C1 1.421(5) . ?
C10 C5 1.432(4) . ?
C10 C9 1.438(5) . ?
N2 C9 1.467(4) . ?
N2 C13 1.474(4) . ?
N2 C14 1.481(4) . ?
N1 C11 1.462(4) . ?
N1 C1 1.464(4) . ?
N1 C12 1.486(4) . ?
C8 C9 1.356(5) . ?
C8 C7 1.401(5) . ?
C5 C6 1.413(5) . ?
C5 C4 1.418(5) . ?
C1 C2 1.372(5) . ?
C7 C6 1.361(5) . ?
C2 C3 1.408(5) . ?
C4 C3 1.358(6) . ?
N4 C16 1.472(5) . ?
N4 C27 1.472(4) . ?
N4 C15 1.486(4) . ?
C28 C27 1.414(5) . ?
C28 C23 1.424(4) . ?
C28 C19 1.431(5) . ?
N3 C19 1.461(4) . ?
N3 C18 1.473(4) . ?
N3 C17 1.484(4) . ?
C23 C22 1.413(5) . ?
C23 C24 1.429(5) . ?
C19 C20 1.362(5) . ?
C27 C26 1.366(5) . ?
C26 C25 1.399(5) . ?
C20 C21 1.410(5) . ?
C21 C22 1.366(5) . ?
C24 C25 1.352(6) . ?
N6 C39 1.469(4) . ?
N6 C41 1.481(4) . ?
N6 C42 1.490(4) . ?
N5 C31 1.460(4) . ?
N5 C29 1.481(4) . ?
N5 C30 1.485(4) . ?
C40 C31 1.415(5) . ?
C40 C35 1.428(4) . ?
C40 C39 1.433(5) . ?
C35 C36 1.407(5) . ?
C35 C34 1.421(5) . ?
C31 C32 1.372(5) . ?
C32 C33 1.396(5) . ?
C39 C38 1.358(5) . ?
C38 C37 1.405(5) . ?
C37 C36 1.360(5) . ?
C33 C34 1.356(5) . ?
C43D O6 1.242(4) . ?
C43D O1 1.289(4) . ?
C43D C44 1.491(4) . ?
C44 C49 1.389(5) . ?
C44 C45 1.397(5) . ?
C45 C46 1.385(5) . ?
C46 C47 1.381(5) . ?
C47 N7 1.382(5) . ?
C47 C48 1.400(5) . ?
C48 C49 1.384(5) . ?
O2 C50E 1.314(4) . ?
O3 C50E 1.224(4) . ?
C50E C51 1.484(5) . ?
C51 C52 1.390(4) . ?
C51 C56 1.396(4) . ?
C52 C53 1.383(5) . ?
C53 C54 1.399(4) . ?
C54 N8 1.358(4) . ?
C54 C55 1.403(4) . ?
C55 C56 1.367(5) . ?
O5 C57F 1.299(4) . ?
O4 C57F 1.231(4) . ?
C57F C58 1.496(4) . ?
C58 C59 1.378(4) . ?
C58 C63 1.398(4) . ?
C59 C60 1.381(4) . ?
C60 C61 1.402(4) . ?
C61 N9 1.375(4) . ?
C61 C62 1.402(4) . ?
C62 C63 1.372(4) . ?
O8 C64G 1.287(4) . ?
O7 C64G 1.235(4) . ?
C64G C65 1.495(4) . ?
C65 C66 1.389(5) . ?
C65 C70 1.395(5) . ?
C66 C67 1.371(5) . ?
C67 C68 1.402(5) . ?
C68 N11 1.386(4) . ?
C68 C69 1.393(5) . ?
C69 C70 1.372(5) . ?
O12 C71H 1.315(4) . ?
O11 C71H 1.233(4) . ?
C71H C72 1.479(4) . ?
C72 C73 1.390(5) . ?
C72 C77 1.392(5) . ?
C73 C74 1.375(5) . ?
C74 C75 1.407(5) . ?
C75 N10 1.389(4) . ?
C75 C76 1.400(5) . ?
C76 C77 1.377(5) . ?
O10 C78I 1.290(4) . ?
O9 C78I 1.241(4) . ?
C78I C79 1.496(5) . ?
C79 C84 1.386(5) . ?
C79 C80 1.400(5) . ?
C80 C81 1.376(5) . ?
C81 C82 1.394(5) . ?
C82 C83 1.394(5) . ?
C82 N12 1.399(4) . ?
C83 C84 1.378(5) . ?

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 C10 C5 117.9(3) . . ?
C1 C10 C9 125.7(3) . . ?
C5 C10 C9 116.4(3) . . ?
C9 N2 C13 113.2(3) . . ?
C9 N2 C14 111.2(3) . . ?
C13 N2 C14 111.1(3) . . ?
C11 N1 C1 112.6(3) . . ?
C11 N1 C12 111.7(3) . . ?
C1 N1 C12 111.7(3) . . ?
C9 C8 C7 121.6(4) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 C10 120.2(3) . . ?
C4 C5 C10 118.8(4) . . ?
C2 C1 C10 121.4(3) . . ?
C2 C1 N1 120.8(4) . . ?
C10 C1 N1 117.8(3) . . ?
C8 C9 C10 121.2(3) . . ?
C8 C9 N2 121.6(3) . . ?
C10 C9 N2 117.2(3) . . ?
C6 C7 C8 119.6(4) . . ?
C1 C2 C3 120.2(4) . . ?
C7 C6 C5 121.0(4) . . ?
C3 C4 C5 121.5(4) . . ?
C4 C3 C2 120.2(4) . . ?
C16 N4 C27 113.3(3) . . ?
C16 N4 C15 112.2(3) . . ?
C27 N4 C15 111.3(3) . . ?
C27 C28 C23 117.7(3) . . ?
C27 C28 C19 125.3(3) . . ?
C23 C28 C19 117.0(3) . . ?
C19 N3 C18 112.5(3) . . ?
C19 N3 C17 111.8(3) . . ?
C18 N3 C17 112.0(3) . . ?
C22 C23 C28 120.1(3) . . ?
C22 C23 C24 120.7(3) . . ?
C28 C23 C24 119.2(4) . . ?
C20 C19 C28 121.8(3) . . ?
C20 C19 N3 120.4(3) . . ?
C28 C19 N3 117.8(3) . . ?
C26 C27 C28 121.8(3) . . ?
C26 C27 N4 119.9(4) . . ?
C28 C27 N4 118.3(3) . . ?
C27 C26 C25 119.7(4) . . ?
C19 C20 C21 120.3(4) . . ?
C22 C21 C20 120.1(4) . . ?
C21 C22 C23 120.8(4) . . ?
C25 C24 C23 120.3(4) . . ?
C24 C25 C26 121.2(4) . . ?
C39 N6 C41 112.0(3) . . ?
C39 N6 C42 112.6(3) . . ?
C41 N6 C42 112.2(3) . . ?
C31 N5 C29 113.2(3) . . ?
C31 N5 C30 111.3(3) . . ?
C29 N5 C30 111.0(3) . . ?
C31 C40 C35 117.9(3) . . ?
C31 C40 C39 125.5(3) . . ?
C35 C40 C39 116.6(3) . . ?
C36 C35 C34 121.6(3) . . ?
C36 C35 C40 119.6(3) . . ?
C34 C35 C40 118.8(4) . . ?
C32 C31 C40 121.3(3) . . ?
C32 C31 N5 120.6(3) . . ?
C40 C31 N5 118.1(3) . . ?
C31 C32 C33 120.4(4) . . ?
C38 C39 C40 122.0(3) . . ?
C38 C39 N6 120.2(3) . . ?
C40 C39 N6 117.9(3) . . ?
C39 C38 C37 120.4(4) . . ?
C36 C37 C38 119.7(4) . . ?
C37 C36 C35 121.7(4) . . ?
C34 C33 C32 120.3(4) . . ?
C33 C34 C35 121.3(4) . . ?
O6 C43D O1 123.4(3) . . ?
O6 C43D C44 120.5(3) . . ?
O1 C43D C44 116.1(3) . . ?
C49 C44 C45 117.6(3) . . ?
C49 C44 C43D 122.4(3) . . ?
C45 C44 C43D 119.9(3) . . ?
C46 C45 C44 120.7(3) . . ?
C47 C46 C45 121.3(4) . . ?
C46 C47 N7 121.1(4) . . ?
C46 C47 C48 118.6(3) . . ?
N7 C47 C48 120.3(4) . . ?
C49 C48 C47 119.7(3) . . ?
C48 C49 C44 122.0(3) . . ?
O3 C50E O2 122.3(3) . . ?
O3 C50E C51 122.6(3) . . ?
O2 C50E C51 115.1(3) . . ?
C52 C51 C56 118.1(3) . . ?
C52 C51 C50E 120.4(3) . . ?
C56 C51 C50E 121.4(3) . . ?
C53 C52 C51 121.4(3) . . ?
C52 C53 C54 120.4(3) . . ?
N8 C54 C53 119.8(3) . . ?
N8 C54 C55 122.3(3) . . ?
C53 C54 C55 117.8(3) . . ?
C56 C55 C54 121.5(3) . . ?
C55 C56 C51 120.8(3) . . ?
O4 C57F O5 123.9(3) . . ?
O4 C57F C58 121.2(3) . . ?
O5 C57F C58 114.9(3) . . ?
C59 C58 C63 118.0(3) . . ?
C59 C58 C57F 121.0(3) . . ?
C63 C58 C57F 121.1(3) . . ?
C58 C59 C60 122.3(3) . . ?
C59 C60 C61 119.8(3) . . ?
N9 C61 C62 121.5(3) . . ?
N9 C61 C60 120.7(3) . . ?
C62 C61 C60 117.7(3) . . ?
C63 C62 C61 121.6(3) . . ?
C62 C63 C58 120.5(3) . . ?
O7 C64G O8 124.3(3) . . ?
O7 C64G C65 121.1(3) . . ?
O8 C64G C65 114.6(3) . . ?
C66 C65 C70 117.7(3) . . ?
C66 C65 C64G 121.7(3) . . ?
C70 C65 C64G 120.5(3) . . ?
C67 C66 C65 120.7(4) . . ?
C66 C67 C68 121.5(4) . . ?
N11 C68 C69 120.2(3) . . ?
N11 C68 C67 122.2(4) . . ?
C69 C68 C67 117.7(3) . . ?
C70 C69 C68 120.4(3) . . ?
C69 C70 C65 121.9(4) . . ?
O11 C71H O12 122.6(3) . . ?
O11 C71H C72 123.5(3) . . ?
O12 C71H C72 113.9(3) . . ?
C73 C72 C77 118.7(3) . . ?
C73 C72 C71H 121.3(3) . . ?
C77 C72 C71H 120.0(3) . . ?
C74 C73 C72 121.8(4) . . ?
C73 C74 C75 119.8(3) . . ?
N10 C75 C76 120.7(4) . . ?
N10 C75 C74 121.0(3) . . ?
C76 C75 C74 118.2(3) . . ?
C77 C76 C75 121.4(4) . . ?
C76 C77 C72 120.2(4) . . ?
O9 C78I O10 123.4(3) . . ?
O9 C78I C79 119.7(3) . . ?
O10 C78I C79 116.9(3) . . ?
C84 C79 C80 118.3(3) . . ?
C84 C79 C78I 122.3(3) . . ?
C80 C79 C78I 119.4(3) . . ?
C81 C80 C79 120.4(4) . . ?
C80 C81 C82 121.4(4) . . ?
C81 C82 C83 117.9(3) . . ?
C81 C82 N12 121.1(4) . . ?
C83 C82 N12 120.9(4) . . ?
C84 C83 C82 120.8(4) . . ?
C83 C84 C79 121.2(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O16 H100 O11 0.92(2) 2.39(9) 2.862(7) 112(7) 2_656
C60 H13 O2 1.01(3) 2.64(3) 3.637(4) 167(2) 2_557
C48 H8 O13 0.97(3) 2.57(3) 3.415(5) 146(3) 2_448
N9 H23 N10 0.84(3) 2.39(3) 3.226(5) 174(3) .
N9 H22 O6 0.82(4) 2.23(4) 3.046(4) 175(4) 2_557
N8 H34 O4 0.92(5) 2.00(5) 2.912(4) 168(4) .
C76 H50 N9 0.98(3) 2.58(3) 3.442(5) 147(2) 2_656
C67 H37 N7 0.99(3) 2.65(4) 3.576(6) 155(2) 2_457
N11 H38 O14 0.89(4) 2.17(4) 3.028(5) 163(3) 1_564
N12 H42 O15 1.01(4) 1.96(5) 2.947(6) 164(3) 2_665
N12 H42 O16 1.01(4) 2.65(4) 3.248(6) 118(3) 1_564
N10 H51 O6 0.93(4) 2.26(4) 3.145(5) 158(3) 1_654
N10 H103 O7 0.87(3) 2.11(3) 2.957(4) 164(3) 2_556
N8 H53 N11 0.77(4) 2.33(4) 3.104(5) 175(5) 2_556
N7 H71 O14 0.77(3) 2.63(3) 3.240(5) 138(3) 2_448
N11 H68 O9 0.91(4) 2.02(4) 2.917(4) 171(3) .
N12 H78 N8 0.92(4) 2.48(4) 3.331(6) 153(3) 1_564
C46 H83 O11 1.12(4) 2.63(4) 3.671(5) 153(3) 2_557
O15 H88 O10 0.75(6) 2.11(6) 2.757(5) 145(7) .
O13 H92 O14 1.09(5) 1.78(5) 2.856(4) 168(4) .
O13 H92 O3 1.09(5) 2.58(5) 3.226(4) 117(3) .
N1 H1A N2 1.30(3) 1.31(3) 2.563(4) 158(2) .
N4 H1B N3 1.23(4) 1.37(4) 2.564(4) 161(3) .
O12 H96 O10 1.02(4) 1.50(4) 2.508(3) 167(4) .
O1 H90 O3 1.32(4) 2.51(4) 3.230(3) 112(2) .
O2 H90 O1 1.19(4) 1.32(4) 2.482(3) 164(4) .
O2 H90 O6 1.19(4) 2.50(4) 3.339(3) 126(3) .
N6 H1C N5 1.16(5) 1.44(5) 2.569(4) 162(3) .
O8 H94 O8 1.224(2) 1.224(2) 2.449(4) 180.00(18) 2_556
O8 H94 O7 1.224(2) 2.569(3) 3.351(4) 119.79(13) 2_556
O13 H91 O1 1.05(6) 1.83(6) 2.849(4) 163(4) .
O5 H95 O5 1.239(2) 1.239(2) 2.478(4) 180.000(1) 2_557
O5 H95 O4 1.239(2) 2.541(2) 3.316(3) 118.51(11) 2_557
O14 H93 O3 1.23(7) 1.56(7) 2.672(4) 146(5) .
N7 H97 O16 0.79(5) 2.33(6) 3.105(8) 166(6) 1_456
O14 H99 N12 1.06(7) 1.87(7) 2.916(4) 170(6) 2_556
C12 H12C O10 0.96 2.61 3.509(4) 156.0 .
C11 H11A O12 0.96 2.48 3.306(4) 143.8 .
C15 H15B O8 0.96 2.61 3.552(4) 167.3 2_566
C16 H16A O8 0.96 2.35 3.230(5) 152.2 1_565
C17 H17B O1 0.96 2.50 3.335(5) 145.8 1_664
C42 H42A O16 0.96 2.59 3.516(6) 163.0 2_656
C30 H30A O10 0.96 2.38 3.310(4) 162.5 .
C41 H41A O11 0.96 2.51 3.356(5) 147.1 .

_refine_diff_density_max         0.662
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 
'slow evaporation from isopropanol at 30 degreesC'
####################################################################### 
# 
# 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_complex_5
_database_code_depnum_ccdc_archive 'CCDC 1831640'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'DMAN 2-cyanobenzoic acid 2-cyanobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N2, 2(C8 H5 N1 O2), C8 H4 N1 O2'
_chemical_formula_sum            'C38 H33 N5 O6'
_chemical_formula_weight         655.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 '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 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.2829(4)
_cell_length_b                   12.5029(5)
_cell_length_c                   23.4257(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.718(2)
_cell_angle_gamma                90
_cell_volume                     3304.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    8964
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      33.58

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_min  0.6730
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction  
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_detector                 'CMOS Detector'
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_reflns_number            46488
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.167
_diffrn_reflns_theta_max         33.716
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6806
_reflns_number_gt                4353
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

_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 > 2σ(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.
;

_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6806
_refine_ls_number_parameters     574
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H33 H 0.4171(18) 0.6436(17) 0.6565(9) 0.032(6) Uiso 1 1 d . . . . .
H20 H 0.254(2) 0.7676(17) 0.6508(10) 0.043(7) Uiso 1 1 d . . . . .
H21 H 0.2780(19) 0.9326(17) 0.6069(9) 0.034(6) Uiso 1 1 d . . . . .
H22 H 0.4630(18) 0.9752(17) 0.5623(9) 0.033(6) Uiso 1 1 d . . . . .
O1 O 0.71332(12) 0.66421(10) 0.57978(6) 0.0284(4) Uani 1 1 d . . . . .
O2 O 0.63124(12) 0.59395(11) 0.65783(6) 0.0267(3) Uani 1 1 d . . . . .
C31 C 0.63363(17) 0.65771(15) 0.61662(9) 0.0215(4) Uani 1 1 d . . . . .
C32 C 0.53115(17) 0.73528(15) 0.61136(8) 0.0198(4) Uani 1 1 d . . . . .
C33 C 0.42271(18) 0.71130(17) 0.63602(9) 0.0252(5) Uani 1 1 d . . . . .
C34 C 0.3290(2) 0.78320(18) 0.63353(10) 0.0303(5) Uani 1 1 d . . . . .
C35 C 0.3426(2) 0.88142(18) 0.60687(9) 0.0297(5) Uani 1 1 d . . . . .
C36 C 0.44863(18) 0.90694(17) 0.58189(9) 0.0248(5) Uani 1 1 d . . . . .
C37 C 0.54224(17) 0.83409(15) 0.58350(8) 0.0207(4) Uani 1 1 d . . . . .
C38 C 0.65254(19) 0.86753(15) 0.55903(9) 0.0247(5) Uani 1 1 d . . . . .
N5 N 0.73697(17) 0.90225(14) 0.53994(9) 0.0393(5) Uani 1 1 d . . . . .
H23 H 0.9859(19) 0.4072(18) 0.4994(9) 0.039(6) Uiso 1 1 d . . . . .
H24 H 1.0911(18) 0.2630(15) 0.4610(8) 0.024(5) Uiso 1 1 d . . . . .
H25 H 1.0098(16) 0.0880(16) 0.4661(8) 0.020(5) Uiso 1 1 d . . . . .
H26 H 0.8280(17) 0.0615(16) 0.5085(8) 0.026(6) Uiso 1 1 d . . . . .
H27 H 0.785(2) 0.566(2) 0.5656(12) 0.078(9) Uiso 1 1 d . . . . .
O3 O 0.83561(12) 0.50556(10) 0.54702(6) 0.0226(3) Uani 1 1 d . . . . .
O4 O 0.67737(12) 0.40577(11) 0.56713(6) 0.0305(4) Uani 1 1 d . . . . .
C15 C 0.77687(18) 0.41408(15) 0.54893(8) 0.0197(4) Uani 1 1 d . . . . .
C18 C 0.84373(17) 0.32161(14) 0.52545(8) 0.0174(4) Uani 1 1 d . . . . .
C17 C 0.79560(17) 0.21770(15) 0.52729(8) 0.0191(4) Uani 1 1 d . . . . .
C19 C 0.95400(17) 0.33560(16) 0.50094(8) 0.0199(4) Uani 1 1 d . . . . .
C20 C 1.01576(19) 0.25019(15) 0.47849(9) 0.0216(4) Uani 1 1 d . . . . .
C16 C 0.68070(19) 0.19414(15) 0.55093(9) 0.0231(5) Uani 1 1 d . . . . .
C21 C 0.96893(18) 0.14795(16) 0.48136(9) 0.0219(5) Uani 1 1 d . . . . .
C22 C 0.85914(18) 0.13173(16) 0.50510(9) 0.0232(5) Uani 1 1 d . . . . .
N3 N 0.59140(16) 0.16621(13) 0.56855(8) 0.0308(4) Uani 1 1 d . . . . .
H28 H 0.747(2) 0.527(2) 0.6710(10) 0.055(8) Uiso 1 1 d . . . . .
H29 H 0.9405(18) 0.3214(16) 0.6752(9) 0.036(6) Uiso 1 1 d . . . . .
H30 H 1.0985(18) 0.2076(17) 0.7013(9) 0.029(6) Uiso 1 1 d . . . . .
H32 H 1.1187(17) 0.3493(15) 0.8581(9) 0.026(6) Uiso 1 1 d . . . . .
H31 H 1.1852(17) 0.2189(15) 0.7940(8) 0.019(5) Uiso 1 1 d . . . . .
O5 O 0.81500(13) 0.48098(11) 0.68071(6) 0.0265(3) Uani 1 1 d . . . . .
O6 O 0.78018(13) 0.52613(11) 0.77137(6) 0.0320(4) Uani 1 1 d . . . . .
C27 C 1.08251(18) 0.34281(16) 0.82155(10) 0.0255(5) Uani 1 1 d . . . . .
C26 C 0.95742(19) 0.49329(17) 0.84681(9) 0.0270(5) Uani 1 1 d . . . . .
C29 C 1.06995(19) 0.26050(16) 0.72939(10) 0.0264(5) Uani 1 1 d . . . . .
C28 C 1.12166(19) 0.26728(16) 0.78298(10) 0.0272(5) Uani 1 1 d . . . . .
C23 C 0.83568(18) 0.47715(15) 0.73599(9) 0.0227(5) Uani 1 1 d . . . . .
C24 C 0.93615(17) 0.40442(15) 0.75186(8) 0.0215(4) Uani 1 1 d . . . . .
C25 C 0.98969(17) 0.41194(15) 0.80613(9) 0.0226(5) Uani 1 1 d . . . . .
C30 C 0.97817(18) 0.32866(16) 0.71392(10) 0.0239(5) Uani 1 1 d . . . . .
N4 N 0.94067(18) 0.55670(16) 0.88095(8) 0.0405(5) Uani 1 1 d . . . . .
H2 H 0.1510(19) 0.4597(17) 0.5671(10) 0.037(6) Uiso 1 1 d . . . . .
H1 H 0.409(2) 0.3236(19) 0.6383(11) 0.057(7) Uiso 1 1 d . . . . .
H4 H 0.0804(18) 0.6263(17) 0.7103(9) 0.030(6) Uiso 1 1 d . . . . .
H3 H 0.0313(19) 0.5826(17) 0.6164(9) 0.039(6) Uiso 1 1 d . . . . .
H9 H 0.4397(18) 0.1961(16) 0.7530(10) 0.031(6) Uiso 1 1 d . . . . .
H7 H 0.328(2) 0.1965(19) 0.7077(11) 0.059(8) Uiso 1 1 d . . . . .
H6 H 0.3664(17) 0.5239(16) 0.8421(9) 0.029(6) Uiso 1 1 d . . . . .
H5 H 0.2062(19) 0.6080(17) 0.7955(9) 0.034(6) Uiso 1 1 d . . . . .
H8 H 0.459(2) 0.1534(18) 0.6877(10) 0.044(7) Uiso 1 1 d . . . . .
H11 H 0.339(2) 0.2060(19) 0.5616(10) 0.048(7) Uiso 1 1 d . . . . .
H12 H 0.232(2) 0.221(2) 0.6091(11) 0.056(8) Uiso 1 1 d . . . . .
H10 H 0.218(3) 0.283(2) 0.5461(13) 0.080(10) Uiso 1 1 d . . . . .
H14 H 0.451(2) 0.471(2) 0.5736(11) 0.062(9) Uiso 1 1 d . . . . .
H15 H 0.464(2) 0.3532(19) 0.5380(10) 0.049(7) Uiso 1 1 d . . . . .
H13 H 0.352(2) 0.4412(19) 0.5274(11) 0.051(7) Uiso 1 1 d . . . . .
H18 H 0.6200(17) 0.2736(17) 0.6709(9) 0.028(6) Uiso 1 1 d . . . . .
H16 H 0.603(2) 0.402(2) 0.6814(10) 0.051(7) Uiso 1 1 d . . . . .
H17 H 0.6143(18) 0.3211(16) 0.7358(9) 0.030(6) Uiso 1 1 d . . . . .
H19 H 0.4791(17) 0.3921(15) 0.7981(8) 0.022(5) Uiso 1 1 d . . . . .
N1 N 0.45385(14) 0.31351(12) 0.69295(7) 0.0201(4) Uani 1 1 d . . . . .
N2 N 0.33906(15) 0.35269(14) 0.60059(7) 0.0261(4) Uani 1 1 d . . . . .
C1 C 0.38773(16) 0.39806(14) 0.72158(8) 0.0182(4) Uani 1 1 d . . . . .
C2 C 0.29324(16) 0.44743(15) 0.69031(8) 0.0197(4) Uani 1 1 d . . . . .
C3 C 0.22462(17) 0.52618(15) 0.71924(9) 0.0222(5) Uani 1 1 d . . . . .
C4 C 0.25376(19) 0.55386(16) 0.77617(9) 0.0257(5) Uani 1 1 d . . . . .
C6 C 0.26260(17) 0.42568(15) 0.63225(8) 0.0228(5) Uani 1 1 d . . . . .
C7 C 0.41395(19) 0.42739(16) 0.77608(9) 0.0225(5) Uani 1 1 d . . . . .
C5 C 0.34665(19) 0.50638(16) 0.80393(9) 0.0242(5) Uani 1 1 d . . . . .
C13 C 0.4182(2) 0.20600(17) 0.71282(11) 0.0296(5) Uani 1 1 d . . . . .
C14 C 0.58369(19) 0.3292(2) 0.69577(10) 0.0277(5) Uani 1 1 d . . . . .
C8 C 0.16849(19) 0.47454(18) 0.60606(10) 0.0291(5) Uani 1 1 d . . . . .
C9 C 0.0988(2) 0.54842(18) 0.63565(10) 0.0315(5) Uani 1 1 d . . . . .
C10 C 0.12734(19) 0.57465(18) 0.69030(10) 0.0277(5) Uani 1 1 d . . . . .
C12 C 0.4071(2) 0.4097(2) 0.55568(11) 0.0367(6) Uani 1 1 d . . . . .
C11 C 0.2755(2) 0.2583(2) 0.57672(13) 0.0438(7) 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 C31 1.257(2) . ?
O2 C31 1.252(2) . ?
C31 C32 1.513(3) . ?
C32 C33 1.392(3) . ?
C32 C37 1.403(3) . ?
C33 C34 1.388(3) . ?
C34 C35 1.387(3) . ?
C35 C36 1.376(3) . ?
C36 C37 1.395(3) . ?
C37 C38 1.439(3) . ?
C38 N5 1.143(2) . ?
O3 C15 1.323(2) . ?
O4 C15 1.210(2) . ?
C15 C18 1.489(3) . ?
C18 C19 1.388(3) . ?
C18 C17 1.409(3) . ?
C17 C22 1.396(3) . ?
C17 C16 1.446(3) . ?
C19 C20 1.383(3) . ?
C20 C21 1.385(3) . ?
C16 N3 1.148(2) . ?
C21 C22 1.379(3) . ?
O5 C23 1.314(2) . ?
O6 C23 1.211(2) . ?
C27 C28 1.383(3) . ?
C27 C25 1.402(3) . ?
C26 N4 1.143(3) . ?
C26 C25 1.444(3) . ?
C29 C28 1.380(3) . ?
C29 C30 1.386(3) . ?
C23 C24 1.496(3) . ?
C24 C30 1.387(3) . ?
C24 C25 1.404(3) . ?
N1 C1 1.462(2) . ?
N1 C14 1.479(3) . ?
N1 C13 1.480(3) . ?
N2 C6 1.464(2) . ?
N2 C11 1.486(3) . ?
N2 C12 1.491(3) . ?
C1 C7 1.357(3) . ?
C1 C2 1.426(3) . ?
C2 C6 1.425(3) . ?
C2 C3 1.429(3) . ?
C3 C4 1.413(3) . ?
C3 C10 1.419(3) . ?
C4 C5 1.363(3) . ?
C6 C8 1.364(3) . ?
C7 C5 1.411(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.356(3) . ?

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
O2 C31 O1 126.37(18) . . ?
O2 C31 C32 116.55(17) . . ?
O1 C31 C32 117.08(17) . . ?
C33 C32 C37 117.80(18) . . ?
C33 C32 C31 120.19(18) . . ?
C37 C32 C31 121.98(17) . . ?
C34 C33 C32 121.0(2) . . ?
C35 C34 C33 120.3(2) . . ?
C36 C35 C34 119.9(2) . . ?
C35 C36 C37 119.9(2) . . ?
C36 C37 C32 121.03(18) . . ?
C36 C37 C38 117.25(18) . . ?
C32 C37 C38 121.58(18) . . ?
N5 C38 C37 174.6(2) . . ?
O4 C15 O3 123.60(18) . . ?
O4 C15 C18 122.66(17) . . ?
O3 C15 C18 113.73(17) . . ?
C19 C18 C17 118.47(18) . . ?
C19 C18 C15 121.05(17) . . ?
C17 C18 C15 120.48(17) . . ?
C22 C17 C18 119.92(18) . . ?
C22 C17 C16 116.91(17) . . ?
C18 C17 C16 123.17(17) . . ?
C20 C19 C18 121.25(19) . . ?
C19 C20 C21 120.0(2) . . ?
N3 C16 C17 174.0(2) . . ?
C22 C21 C20 120.0(2) . . ?
C21 C22 C17 120.33(19) . . ?
C28 C27 C25 119.8(2) . . ?
N4 C26 C25 174.5(2) . . ?
C28 C29 C30 120.4(2) . . ?
C29 C28 C27 120.1(2) . . ?
O6 C23 O5 124.68(19) . . ?
O6 C23 C24 122.27(18) . . ?
O5 C23 C24 113.05(18) . . ?
C30 C24 C25 118.65(18) . . ?
C30 C24 C23 121.33(18) . . ?
C25 C24 C23 120.02(18) . . ?
C27 C25 C24 120.24(19) . . ?
C27 C25 C26 117.27(19) . . ?
C24 C25 C26 122.40(18) . . ?
C29 C30 C24 120.9(2) . . ?
C1 N1 C14 113.25(16) . . ?
C1 N1 C13 111.74(16) . . ?
C14 N1 C13 112.29(17) . . ?
C6 N2 C11 113.63(17) . . ?
C6 N2 C12 111.80(17) . . ?
C11 N2 C12 111.4(2) . . ?
C7 C1 C2 121.26(18) . . ?
C7 C1 N1 121.37(17) . . ?
C2 C1 N1 117.37(16) . . ?
C6 C2 C1 125.33(18) . . ?
C6 C2 C3 117.24(17) . . ?
C1 C2 C3 117.42(18) . . ?
C4 C3 C10 121.1(2) . . ?
C4 C3 C2 119.71(18) . . ?
C10 C3 C2 119.22(19) . . ?
C5 C4 C3 120.8(2) . . ?
C8 C6 C2 121.46(19) . . ?
C8 C6 N2 120.76(19) . . ?
C2 C6 N2 117.71(17) . . ?
C1 C7 C5 120.8(2) . . ?
C4 C5 C7 120.0(2) . . ?
C6 C8 C9 120.7(2) . . ?
C10 C9 C8 119.9(2) . . ?
C9 C10 C3 121.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H9 O2 0.98(2) 2.58(2) 3.391(3) 140.0(16) 2_646
O5 H28 O2 0.99(3) 1.57(3) 2.5599(19) 175(2) .
C14 H16 O5 1.00(3) 2.59(2) 3.250(3) 123.7(17) .
C14 H16 O2 1.00(3) 2.48(3) 3.471(3) 171.1(19) .
N2 H1 N1 1.23(3) 1.38(3) 2.555(2) 157(2) .
O3 H27 O1 1.04(3) 1.51(3) 2.5404(18) 167(3) .
C13 H7 O6 1.03(3) 2.51(2) 3.198(3) 123.9(17) 2_646

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'slow evaporation from ethylacetate at 30 degreesC'
####################################################################### 
# 
# 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_complex_7
_database_code_depnum_ccdc_archive 'CCDC 1831646'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT230_complex_7           
;
PROBLEM: Hirshfeld Test Diff for O4E -- N1E .. 7.5 s.u.
RESPONSE: There may be a small amount of disorder in the nitro group 
involving O4E and N1E. 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'DMAN 4-nitrobenzoic acid 4-nitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N2, 2(C7 H5 N1 O4) C7 H4 N1 O4'
_chemical_formula_sum            'C35 H33 N5 O12'
_chemical_formula_weight         715.66

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.6269(4)
_cell_length_b                   18.1672(5)
_cell_length_c                   20.9527(6)
_cell_angle_alpha                93.416(2)
_cell_angle_beta                 104.461(3)
_cell_angle_gamma                107.500(3)
_cell_volume                     5086.9(3)
_cell_formula_units_Z            6


_cell_measurement_temperature    150.00(14)
_cell_measurement_reflns_used    15753
_cell_measurement_theta_min      4.3670
_cell_measurement_theta_max      74.3380
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             2244
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_min  0.97308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.00(14)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_reflns_number            37803
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.301
_diffrn_reflns_theta_max         74.703
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             20174
_reflns_number_gt                16100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'

_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 > 2σ(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.


;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+1.3691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         20174
_refine_ls_number_parameters     1801
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3J O 0.72709(8) 0.83319(7) 0.28301(6) 0.0318(2) Uani 1 1 d . . . . .
O4J O 0.57377(9) 0.76117(7) 0.28363(7) 0.0437(3) Uani 1 1 d . . . . .
H4H H 0.2001(14) 0.1898(10) 0.4795(9) 0.028(4) Uiso 1 1 d . . . . .
H4J H 0.5411(15) 0.8981(11) 0.4747(10) 0.038(5) Uiso 1 1 d . . . . .
H5J H 0.5280(14) 0.8128(11) 0.3779(9) 0.027(4) Uiso 1 1 d . . . . .
H2H H 0.4958(14) 0.2527(10) 0.4105(9) 0.028(4) Uiso 1 1 d . . . . .
H5H H 0.4886(15) 0.3299(11) 0.5032(10) 0.034(5) Uiso 1 1 d . . . . .
H5L H 0.5421(14) 0.9506(11) 0.2650(9) 0.031(5) Uiso 1 1 d . . . . .
H3D H 0.1483(14) 0.7637(10) 0.4156(9) 0.025(4) Uiso 1 1 d . . . . .
H3H H 0.2095(13) 0.1158(10) 0.3851(9) 0.024(4) Uiso 1 1 d . . . . .
H2D H 0.1233(13) 0.6825(10) 0.3143(9) 0.023(4) Uiso 1 1 d . . . . .
H5D H -0.1613(15) 0.6853(11) 0.2497(10) 0.035(5) Uiso 1 1 d . . . . .
H5I H 0.8850(14) 0.5297(10) 0.3456(10) 0.030(5) Uiso 1 1 d . . . . .
H11C H -0.4123(14) 0.4601(11) -0.2294(10) 0.034(5) Uiso 1 1 d . . . . .
H13C H -0.4711(15) 0.3696(12) -0.2585(10) 0.035(5) Uiso 1 1 d . . . . .
H2L H 0.8089(16) 1.1150(12) 0.2792(10) 0.041(5) Uiso 1 1 d . . . . .
H4B H -0.0013(14) 1.1681(11) 0.4006(10) 0.034(5) Uiso 1 1 d . . . . .
H5B H 0.0030(16) 1.2531(12) 0.3175(11) 0.046(6) Uiso 1 1 d . . . . .
H2J H 0.8095(15) 0.9351(11) 0.3802(10) 0.036(5) Uiso 1 1 d . . . . .
H5C H -0.3233(15) 0.0835(11) -0.3101(10) 0.036(5) Uiso 1 1 d . . . . .
H3B H 0.0007(15) 1.0480(11) 0.4361(10) 0.037(5) Uiso 1 1 d . . . . .
H1G H 0.1927(16) 0.3349(12) 0.3779(11) 0.044(6) Uiso 1 1 d . . . . .
H1K H 0.7615(16) 0.5737(13) 0.0312(11) 0.045(6) Uiso 1 1 d . . . . .
H3J H 0.8251(15) 1.0181(11) 0.4760(10) 0.034(5) Uiso 1 1 d . . . . .
H3L H 0.7903(15) 1.1872(12) 0.3700(10) 0.038(5) Uiso 1 1 d . . . . .
H4G H 0.4637(15) 0.4950(12) 0.4022(10) 0.034(5) Uiso 1 1 d . . . . .
H4F H 0.2842(14) 0.0671(11) 0.0138(10) 0.034(5) Uiso 1 1 d . . . . .
H2G H 0.2174(15) 0.2638(12) 0.2887(10) 0.036(5) Uiso 1 1 d . . . . .
H2I H 1.1627(16) 0.5418(11) 0.4535(10) 0.038(5) Uiso 1 1 d . . . . .
H8B H 0.0970(14) 0.8743(11) 0.2312(10) 0.034(5) Uiso 1 1 d . . . . .
H11A H 0.6053(14) 0.1956(11) 0.1924(10) 0.032(5) Uiso 1 1 d . . . . .
H11B H -0.0835(15) 0.8444(11) 0.1839(10) 0.036(5) Uiso 1 1 d . . . . .
H9C H -0.2304(16) 0.5086(12) -0.2079(11) 0.044(6) Uiso 1 1 d . . . . .
H12B H -0.1342(15) 0.9100(11) 0.1989(10) 0.032(5) Uiso 1 1 d . . . . .
H3C H -0.3416(15) 0.2731(11) -0.4432(11) 0.039(5) Uiso 1 1 d . . . . .
H9B H 0.1578(16) 0.9530(12) 0.2793(10) 0.035(5) Uiso 1 1 d . . . . .
H10C H -0.2471(15) 0.4853(11) -0.2886(11) 0.038(5) Uiso 1 1 d . . . . .
H12C H -0.4341(15) 0.4272(12) -0.3083(11) 0.041(5) Uiso 1 1 d . . . . .
H2K H 0.7418(15) 0.6529(11) 0.1157(10) 0.036(5) Uiso 1 1 d . . . . .
H10B H 0.0835(15) 0.8853(11) 0.3056(10) 0.037(5) Uiso 1 1 d . . . . .
H12A H 0.6126(16) 0.2184(12) 0.2696(11) 0.042(5) Uiso 1 1 d . . . . .
H13A H 0.5373(15) 0.2418(11) 0.2125(9) 0.032(5) Uiso 1 1 d . . . . .
H3G H 0.4863(15) 0.4259(11) 0.3113(10) 0.035(5) Uiso 1 1 d . . . . .
H1F H 0.4773(15) -0.0143(11) 0.1417(10) 0.033(5) Uiso 1 1 d . . . . .
H8C H -0.1765(16) 0.4543(12) -0.2334(10) 0.039(5) Uiso 1 1 d . . . . .
H10A H 0.7780(15) 0.2528(12) 0.2061(10) 0.039(5) Uiso 1 1 d . . . . .
H2C H -0.3390(15) 0.3816(12) -0.3746(10) 0.040(5) Uiso 1 1 d . . . . .
H13B H -0.1010(16) 0.8606(12) 0.2581(11) 0.043(5) Uiso 1 1 d . . . . .
H17B H 0.1323(16) 1.1072(13) 0.1096(11) 0.047(6) Uiso 1 1 d . . . . .
H4L H 0.5233(16) 1.0213(12) 0.3565(10) 0.040(5) Uiso 1 1 d . . . . .
H4D H -0.1353(14) 0.7652(11) 0.3501(9) 0.031(5) Uiso 1 1 d . . . . .
H4C H -0.3321(15) 0.1604(12) -0.4000(10) 0.040(5) Uiso 1 1 d . . . . .
H19B H 0.1329(15) 1.0194(12) 0.1077(10) 0.040(5) Uiso 1 1 d . . . . .
H2F H 0.4684(16) -0.1083(13) 0.0563(11) 0.046(6) Uiso 1 1 d . . . . .
H17A H 0.7218(16) 0.3592(13) 0.0684(11) 0.045(6) Uiso 1 1 d . . . . .
H6A H 0.6081(16) 0.5147(12) 0.1037(11) 0.043(6) Uiso 1 1 d . . . . .
H16C H -0.2219(17) 0.3100(13) -0.0628(12) 0.051(6) Uiso 1 1 d . . . . .
H18B H 0.1833(16) 1.0764(12) 0.1789(11) 0.044(6) Uiso 1 1 d . . . . .
H4A H 0.6786(16) 0.5337(12) 0.3839(11) 0.042(5) Uiso 1 1 d . . . . .
H7B H 0.0284(14) 1.1807(11) 0.1347(10) 0.034(5) Uiso 1 1 d . . . . .
H4I H 0.8711(16) 0.6063(12) 0.4358(10) 0.039(5) Uiso 1 1 d . . . . .
H2A H 0.7047(15) 0.3225(12) 0.3519(10) 0.035(5) Uiso 1 1 d . . . . .
H3E H -0.0990(14) 0.2743(11) 0.0991(10) 0.033(5) Uiso 1 1 d . . . . .
H15A H 0.5208(17) 0.3801(13) 0.0494(11) 0.048(6) Uiso 1 1 d . . . . .
H14A H 0.5440(16) 0.2994(12) 0.0517(11) 0.043(5) Uiso 1 1 d . . . . .
H1E H 0.0457(14) 0.4495(11) 0.0132(9) 0.031(5) Uiso 1 1 d . . . . .
H2B H 0.0087(15) 0.9477(12) 0.3623(10) 0.036(5) Uiso 1 1 d . . . . .
H3K H 0.7160(17) 0.7290(13) -0.0948(12) 0.052(6) Uiso 1 1 d . . . . .
H7A H 0.6155(17) 0.6165(14) 0.1816(12) 0.053(6) Uiso 1 1 d . . . . .
H3A H 0.7054(17) 0.4252(13) 0.4263(12) 0.052(6) Uiso 1 1 d . . . . .
H4E H -0.1088(18) 0.1806(14) 0.0119(12) 0.055(6) Uiso 1 1 d . . . . .
H3I H 1.1485(16) 0.6202(11) 0.5422(11) 0.038(5) Uiso 1 1 d . . . . .
H2E H 0.0385(18) 0.3531(13) -0.0751(12) 0.054(6) Uiso 1 1 d . . . . .
H15B H -0.0517(17) 0.9654(13) 0.0654(11) 0.049(6) Uiso 1 1 d . . . . .
H8A H 0.7998(17) 0.2845(13) 0.2858(12) 0.050(6) Uiso 1 1 d . . . . .
H5A H 0.6493(16) 0.6085(13) 0.2962(11) 0.047(6) Uiso 1 1 d . . . . .
H6B H 0.0126(16) 1.2781(13) 0.2088(11) 0.048(6) Uiso 1 1 d . . . . .
H16B H -0.1207(17) 0.9975(13) 0.1030(11) 0.048(6) Uiso 1 1 d . . . . .
H18A H 0.6993(17) 0.4403(13) 0.0553(12) 0.050(6) Uiso 1 1 d . . . . .
H7C H -0.3080(16) 0.1802(13) -0.1237(12) 0.048(6) Uiso 1 1 d . . . . .
H4K H 0.6840(17) 0.8037(13) -0.0124(11) 0.050(6) Uiso 1 1 d . . . . .
H9A H 0.8275(17) 0.3459(13) 0.2343(11) 0.049(6) Uiso 1 1 d . . . . .
H16A H 0.4899(18) 0.3271(13) 0.1057(12) 0.052(6) Uiso 1 1 d . . . . .
H14B H -0.0520(16) 1.0545(13) 0.0612(11) 0.045(6) Uiso 1 1 d . . . . .
H3F H 0.2746(17) -0.0290(13) -0.0752(12) 0.052(6) Uiso 1 1 d . . . . .
H17C H -0.4083(18) 0.2568(14) -0.0925(12) 0.056(7) Uiso 1 1 d . . . . .
H6C H -0.3102(16) 0.0747(13) -0.1952(11) 0.046(6) Uiso 1 1 d . . . . .
H18C H -0.4100(17) 0.3442(14) -0.1001(12) 0.054(6) Uiso 1 1 d . . . . .
H19C H -0.4699(18) 0.2748(13) -0.1636(12) 0.049(6) Uiso 1 1 d . . . . .
H1I H 0.9763(19) 0.4502(14) 0.2420(13) 0.064(7) Uiso 1 1 d . . . . .
H19A H 0.7805(19) 0.4347(14) 0.1219(13) 0.056(7) Uiso 1 1 d . . . . .
H1D H 0.023(2) 0.5642(16) 0.1653(14) 0.075(8) Uiso 1 1 d . . . . .
H14C H -0.1657(19) 0.3605(14) -0.1110(12) 0.057(7) Uiso 1 1 d . . . . .
H5G H 0.3260(19) 0.1945(15) 0.1831(13) 0.064(7) Uiso 1 1 d . . . . .
H15C H -0.2298(17) 0.3951(13) -0.0669(12) 0.051(6) Uiso 1 1 d . . . . .
H1H H 0.427(2) 0.1237(17) 0.2673(15) 0.083(9) Uiso 1 1 d . . . . .
H1J H 0.709(2) 0.8064(16) 0.2383(15) 0.078(9) Uiso 1 1 d . . . . .
H1L H 0.635(3) 0.8866(19) 0.1483(17) 0.105(11) Uiso 1 1 d . . . . .
H1C H -0.3157(16) 0.3788(12) -0.1990(11) 0.047(6) Uiso 1 1 d . . . . .
H1 H 0.0225(17) 0.9693(13) 0.1993(12) 0.050(6) Uiso 1 1 d . . . . .
H1A H 0.6687(16) 0.3258(12) 0.1801(11) 0.047(6) Uiso 1 1 d . . . . .
O1H O 0.43633(8) 0.15133(6) 0.31244(6) 0.0309(2) Uani 1 1 d . . . . .
O3H O 0.41522(10) 0.36977(7) 0.58351(7) 0.0436(3) Uani 1 1 d . . . . .
C7H C 0.43606(11) 0.24058(9) 0.42414(8) 0.0260(3) Uani 1 1 d . . . . .
O2H O 0.27898(10) 0.07450(7) 0.29837(6) 0.0413(3) Uani 1 1 d . . . . .
C6H C 0.43307(11) 0.28539(9) 0.47878(8) 0.0264(3) Uani 1 1 d . . . . .
N7 N 0.34271(10) 0.31176(8) 0.55706(7) 0.0298(3) Uani 1 1 d . . . . .
C4H C 0.34562(11) 0.26535(8) 0.49825(7) 0.0244(3) Uani 1 1 d . . . . .
O4H O 0.26889(10) 0.29062(7) 0.57739(6) 0.0404(3) Uani 1 1 d . . . . .
C3H C 0.26562(11) 0.15919(8) 0.41005(8) 0.0261(3) Uani 1 1 d . . . . .
C2H C 0.35262(11) 0.17736(8) 0.38952(7) 0.0246(3) Uani 1 1 d . . . . .
C5H C 0.26134(11) 0.20315(9) 0.46488(8) 0.0269(3) Uani 1 1 d . . . . .
C1H C 0.35190(12) 0.12857(9) 0.32879(7) 0.0271(3) Uani 1 1 d . . . . .
O2J O 0.77619(11) 1.06569(8) 0.56805(7) 0.0476(3) Uani 1 1 d . . . . .
N1J N 0.69634(11) 1.01355(8) 0.54343(7) 0.0321(3) Uani 1 1 d . . . . .
C4J C 0.76579(12) 0.97629(9) 0.45585(8) 0.0287(3) Uani 1 1 d . . . . .
O1J O 0.62560(11) 1.00125(8) 0.56691(7) 0.0461(3) Uani 1 1 d . . . . .
C7J C 0.58728(11) 0.85486(9) 0.39896(8) 0.0258(3) Uani 1 1 d . . . . .
C6J C 0.59579(12) 0.90332(9) 0.45517(8) 0.0273(3) Uani 1 1 d . . . . .
C3J C 0.75552(11) 0.92765(9) 0.39932(8) 0.0274(3) Uani 1 1 d . . . . .
C2J C 0.66642(11) 0.86690(8) 0.37069(7) 0.0238(3) Uani 1 1 d . . . . .
C1J C 0.65063(11) 0.81439(9) 0.30816(8) 0.0267(3) Uani 1 1 d . . . . .
C5J C 0.68549(12) 0.96290(8) 0.48271(7) 0.0265(3) Uani 1 1 d . . . . .
O3F O 0.34650(9) 0.14258(6) 0.12881(5) 0.0313(2) Uani 1 1 d . . . . .
O4F O 0.42483(9) 0.07998(6) 0.20106(5) 0.0323(2) Uani 1 1 d . . . . .
C1F C 0.38436(11) 0.09039(8) 0.14373(7) 0.0244(3) Uani 1 1 d . . . . .
C2F C 0.38067(11) 0.03298(8) 0.08686(7) 0.0240(3) Uani 1 1 d . . . . .
C6F C 0.42932(13) -0.07332(9) 0.04811(8) 0.0318(3) Uani 1 1 d . . . . .
C7F C 0.43545(12) -0.01795(9) 0.09879(8) 0.0281(3) Uani 1 1 d . . . . .
C3F C 0.32162(13) 0.02995(9) 0.02272(8) 0.0313(3) Uani 1 1 d . . . . .
C4F C 0.31446(14) -0.02472(10) -0.02872(8) 0.0356(4) Uani 1 1 d . . . . .
O1F O 0.38978(19) -0.18786(11) -0.05562(9) 0.0845(7) Uani 1 1 d . . . . .
C5F C 0.36727(13) -0.07626(9) -0.01429(8) 0.0310(3) Uani 1 1 d . . . . .
N1F N 0.35547(14) -0.13662(9) -0.06804(8) 0.0470(4) Uani 1 1 d . . . . .
O2F O 0.3111(2) -0.13296(14) -0.12396(9) 0.1050(9) Uani 1 1 d . . . . .
O2G O 0.30793(9) 0.22503(6) 0.21453(6) 0.0304(2) Uani 1 1 d . . . . .
O1G O 0.43765(9) 0.32639(7) 0.21039(6) 0.0370(3) Uani 1 1 d . . . . .
O4G O 0.25836(10) 0.42849(7) 0.48294(6) 0.0397(3) Uani 1 1 d . . . . .
N1G N 0.31519(10) 0.46355(8) 0.45258(7) 0.0299(3) Uani 1 1 d . . . . .
C3G C 0.26623(11) 0.31069(9) 0.31110(8) 0.0257(3) Uani 1 1 d . . . . .
O3G O 0.36081(11) 0.53375(7) 0.46616(7) 0.0463(3) Uani 1 1 d . . . . .
C6G C 0.41562(12) 0.44861(9) 0.37848(8) 0.0288(3) Uani 1 1 d . . . . .
C1G C 0.37013(11) 0.29630(9) 0.23420(7) 0.0252(3) Uani 1 1 d . . . . .
C5G C 0.32841(11) 0.41972(8) 0.39660(7) 0.0246(3) Uani 1 1 d . . . . .
C2G C 0.35272(11) 0.33887(8) 0.29101(7) 0.0229(3) Uani 1 1 d . . . . .
C4G C 0.25302(11) 0.35154(9) 0.36421(8) 0.0266(3) Uani 1 1 d . . . . .
C7G C 0.42682(12) 0.40732(9) 0.32477(8) 0.0281(3) Uani 1 1 d . . . . .
O3L O 0.61763(9) 0.91840(7) 0.17951(6) 0.0379(3) Uani 1 1 d . . . . .
O4L O 0.77196(10) 1.00163(8) 0.19348(6) 0.0402(3) Uani 1 1 d . . . . .
C4L C 0.58210(11) 1.04090(9) 0.34029(8) 0.0272(3) Uani 1 1 d . . . . .
C6L C 0.74158(12) 1.13955(9) 0.34857(8) 0.0296(3) Uani 1 1 d . . . . .
O1L O 0.59569(11) 1.11966(8) 0.46052(7) 0.0473(3) Uani 1 1 d . . . . .
O2L O 0.69162(11) 1.22553(7) 0.43895(7) 0.0487(3) Uani 1 1 d . . . . .
C7L C 0.75078(12) 1.09679(9) 0.29515(8) 0.0288(3) Uani 1 1 d . . . . .
C5L C 0.65734(12) 1.11027(9) 0.36997(7) 0.0266(3) Uani 1 1 d . . . . .
C2L C 0.67677(11) 1.02666(9) 0.26407(7) 0.0252(3) Uani 1 1 d . . . . .
N1L N 0.64760(11) 1.15491(8) 0.42716(7) 0.0339(3) Uani 1 1 d . . . . .
C1L C 0.69371(12) 0.98103(9) 0.20852(8) 0.0298(3) Uani 1 1 d . . . . .
C3L C 0.59224(11) 0.99911(9) 0.28636(8) 0.0271(3) Uani 1 1 d . . . . .
O1K O 0.70237(9) 0.75964(7) 0.16979(6) 0.0352(3) Uani 1 1 d . . . . .
O2K O 0.65718(13) 0.83575(8) 0.09678(7) 0.0530(4) Uani 1 1 d . . . . .
C2K C 0.70896(11) 0.73433(9) 0.05974(7) 0.0264(3) Uani 1 1 d . . . . .
C4K C 0.74585(13) 0.62141(10) 0.02246(9) 0.0336(3) Uani 1 1 d . . . . .
O4K O 0.73442(14) 0.52751(9) -0.08890(8) 0.0616(4) Uani 1 1 d . . . . .
C7K C 0.70287(14) 0.75752(10) -0.00239(8) 0.0353(4) Uani 1 1 d . . . . .
C1K C 0.68756(12) 0.78047(9) 0.11344(8) 0.0288(3) Uani 1 1 d . . . . .
N1K N 0.74845(14) 0.59699(10) -0.09347(8) 0.0456(4) Uani 1 1 d . . . . .
C3K C 0.73340(12) 0.66739(9) 0.07239(8) 0.0302(3) Uani 1 1 d . . . . .
C5K C 0.73771(13) 0.64580(10) -0.03925(8) 0.0327(3) Uani 1 1 d . . . . .
O3K O 0.77156(16) 0.62782(11) -0.14008(7) 0.0700(5) Uani 1 1 d . . . . .
C6K C 0.71956(15) 0.71425(11) -0.05238(8) 0.0387(4) Uani 1 1 d . . . . .
O4I O 0.96818(9) 0.47470(7) 0.27942(6) 0.0346(3) Uani 1 1 d . . . . .
N1I N 1.00155(10) 0.66675(7) 0.55135(7) 0.0302(3) Uani 1 1 d . . . . .
O1I O 0.93258(9) 0.69304(7) 0.54170(7) 0.0413(3) Uani 1 1 d . . . . .
O3I O 1.10830(10) 0.45882(8) 0.34076(6) 0.0439(3) Uani 1 1 d . . . . .
O2I O 1.06526(10) 0.67868(8) 0.60516(6) 0.0445(3) Uani 1 1 d . . . . .
C3I C 0.93932(11) 0.54880(9) 0.38611(7) 0.0256(3) Uani 1 1 d . . . . .
C6I C 1.10434(13) 0.55583(10) 0.44988(8) 0.0321(3) Uani 1 1 d . . . . .
C2I C 0.93028(11) 0.59363(9) 0.43866(8) 0.0259(3) Uani 1 1 d . . . . .
C7I C 1.09670(13) 0.60096(10) 0.50266(8) 0.0324(3) Uani 1 1 d . . . . .
C4I C 1.02627(11) 0.53013(8) 0.39161(7) 0.0249(3) Uani 1 1 d . . . . .
C1I C 1.00973(11) 0.61860(8) 0.49563(7) 0.0253(3) Uani 1 1 d . . . . .
C5I C 1.03878(12) 0.48340(9) 0.33475(8) 0.0283(3) Uani 1 1 d . . . . .
O2D O 0.04020(8) 0.60888(6) 0.20268(6) 0.0319(2) Uani 1 1 d . . . . .
O1D O -0.12262(9) 0.59457(7) 0.17160(6) 0.0382(3) Uani 1 1 d . . . . .
O3D O 0.09100(10) 0.81713(7) 0.50032(6) 0.0388(3) Uani 1 1 d . . . . .
N1D N 0.02476(11) 0.81845(8) 0.45192(7) 0.0312(3) Uani 1 1 d . . . . .
O4D O -0.02899(11) 0.85889(8) 0.45252(7) 0.0464(3) Uani 1 1 d . . . . .
C5D C 0.00847(12) 0.76898(8) 0.38916(7) 0.0252(3) Uani 1 1 d . . . . .
C4D C 0.08666(11) 0.74589(8) 0.38014(8) 0.0263(3) Uani 1 1 d . . . . .
C2D C -0.02047(11) 0.67672(8) 0.27298(7) 0.0241(3) Uani 1 1 d . . . . .
C7D C -0.09782(12) 0.70098(9) 0.28371(8) 0.0282(3) Uani 1 1 d . . . . .
C6D C -0.08355(12) 0.74833(9) 0.34220(8) 0.0287(3) Uani 1 1 d . . . . .
C3D C 0.07177(11) 0.69974(8) 0.32096(8) 0.0257(3) Uani 1 1 d . . . . .
C1D C -0.04003(12) 0.62255(8) 0.21032(7) 0.0263(3) Uani 1 1 d . . . . .
O1E O 0.00803(10) 0.49773(6) 0.11241(6) 0.0364(3) Uani 1 1 d . . . . .
O2E O -0.02850(10) 0.40209(7) 0.17380(6) 0.0373(3) Uani 1 1 d . . . . .
N2C N -0.31850(10) 0.31666(8) -0.14823(6) 0.0288(3) Uani 1 1 d . . . . .
C9C C -0.32269(10) 0.26181(8) -0.26060(7) 0.0238(3) Uani 1 1 d . . . . .
N1C N -0.32326(9) 0.39854(7) -0.24571(6) 0.0252(3) Uani 1 1 d . . . . .
C4C C -0.33146(11) 0.20361(10) -0.37213(8) 0.0307(3) Uani 1 1 d . . . . .
C8C C -0.31700(11) 0.25262(9) -0.19280(8) 0.0271(3) Uani 1 1 d . . . . .
C2E C -0.02419(11) 0.36882(9) 0.06494(7) 0.0258(3) Uani 1 1 d . . . . .
C5C C -0.31977(12) 0.12739(9) -0.27910(10) 0.0348(4) Uani 1 1 d . . . . .
C3E C 0.01595(12) 0.39300(9) 0.01305(8) 0.0283(3) Uani 1 1 d . . . . .
C10C C -0.32451(11) 0.19731(9) -0.30419(8) 0.0274(3) Uani 1 1 d . . . . .
C1C C -0.32757(11) 0.33024(8) -0.28922(7) 0.0245(3) Uani 1 1 d . . . . .
C3C C -0.33682(12) 0.27030(10) -0.39719(8) 0.0321(3) Uani 1 1 d . . . . .
C1E C -0.01431(11) 0.42809(9) 0.12182(7) 0.0266(3) Uani 1 1 d . . . . .
C11C C -0.41914(13) 0.41566(10) -0.26195(9) 0.0324(3) Uani 1 1 d . . . . .
C7C C -0.31158(14) 0.18410(10) -0.17053(9) 0.0368(4) Uani 1 1 d . . . . .
C12C C -0.23643(13) 0.46864(10) -0.24380(9) 0.0340(3) Uani 1 1 d . . . . .
C7E C -0.07187(14) 0.28953(10) 0.06438(8) 0.0358(4) Uani 1 1 d . . . . .
C6E C -0.07676(16) 0.23512(10) 0.01362(9) 0.0436(4) Uani 1 1 d . . . . .
C4E C 0.01213(13) 0.33923(11) -0.03803(8) 0.0349(4) Uani 1 1 d . . . . .
O4E O -0.00485(17) 0.22998(11) -0.13680(9) 0.0780(6) Uani 1 1 d . . . . .
C6C C -0.31299(14) 0.12104(10) -0.21390(10) 0.0405(4) Uani 1 1 d . . . . .
C2C C -0.33455(12) 0.33460(10) -0.35509(8) 0.0303(3) Uani 1 1 d . . . . .
C5E C -0.03321(14) 0.26144(11) -0.03606(8) 0.0393(4) Uani 1 1 d . . . . .
C13C C -0.40885(15) 0.29588(12) -0.12441(10) 0.0408(4) Uani 1 1 d . . . . .
O3E O -0.0665(2) 0.13596(10) -0.08604(10) 0.0901(7) Uani 1 1 d . . . . .
C14C C -0.22658(15) 0.34819(12) -0.09279(9) 0.0413(4) Uani 1 1 d . . . . .
N1E N -0.03478(16) 0.20464(11) -0.08993(9) 0.0563(5) Uani 1 1 d . . . . .
N1B N 0.01505(9) 0.94514(7) 0.23959(6) 0.0235(2) Uani 1 1 d . . . . .
C9B C 0.01634(10) 1.08156(8) 0.26142(7) 0.0226(3) Uani 1 1 d . . . . .
N2B N 0.03106(9) 1.03884(7) 0.15086(6) 0.0257(3) Uani 1 1 d . . . . .
C1B C 0.01467(10) 1.00941(8) 0.28539(7) 0.0233(3) Uani 1 1 d . . . . .
C10B C 0.00998(10) 1.14112(8) 0.30637(8) 0.0257(3) Uani 1 1 d . . . . .
C11B C 0.09587(12) 0.91200(9) 0.26656(8) 0.0290(3) Uani 1 1 d . . . . .
C13B C -0.08595(12) 0.88389(9) 0.21711(8) 0.0291(3) Uani 1 1 d . . . . .
C4B C 0.00395(11) 1.12670(9) 0.37107(8) 0.0299(3) Uani 1 1 d . . . . .
C8B C 0.02327(11) 1.09842(8) 0.19700(7) 0.0253(3) Uani 1 1 d . . . . .
C3B C 0.00375(12) 1.05704(10) 0.39181(8) 0.0314(3) Uani 1 1 d . . . . .
C7B C 0.02286(13) 1.16956(10) 0.17880(8) 0.0332(3) Uani 1 1 d . . . . .
C5B C 0.00838(12) 1.21339(9) 0.28517(9) 0.0316(3) Uani 1 1 d . . . . .
C2B C 0.00861(12) 0.99740(9) 0.34809(8) 0.0291(3) Uani 1 1 d . . . . .
C6B C 0.01466(13) 1.22747(10) 0.22306(9) 0.0352(4) Uani 1 1 d . . . . .
C15B C 0.12747(13) 1.06250(10) 0.13476(9) 0.0344(4) Uani 1 1 d . . . . .
C14B C -0.05445(14) 1.01315(11) 0.09060(9) 0.0383(4) Uani 1 1 d . . . . .
N1A N 0.68105(10) 0.30692(7) 0.22482(6) 0.0263(3) Uani 1 1 d . . . . .
N2A N 0.64087(10) 0.38243(8) 0.12557(7) 0.0303(3) Uani 1 1 d . . . . .
C1A C 0.68061(11) 0.37268(9) 0.26945(8) 0.0280(3) Uani 1 1 d . . . . .
C9A C 0.66396(11) 0.43856(9) 0.24158(8) 0.0278(3) Uani 1 1 d . . . . .
C10A C 0.66515(11) 0.50123(9) 0.28688(9) 0.0330(4) Uani 1 1 d . . . . .
C4A C 0.68088(12) 0.49473(11) 0.35547(9) 0.0383(4) Uani 1 1 d . . . . .
C13A C 0.60095(12) 0.23276(9) 0.22406(9) 0.0301(3) Uani 1 1 d . . . . .
C8A C 0.64295(12) 0.44586(9) 0.17270(9) 0.0309(3) Uani 1 1 d . . . . .
C2A C 0.69448(13) 0.36798(11) 0.33581(8) 0.0350(4) Uani 1 1 d . . . . .
C14A C 0.78173(12) 0.29735(10) 0.23877(9) 0.0339(3) Uani 1 1 d . . . . .
C5A C 0.64654(13) 0.56783(10) 0.26228(11) 0.0403(4) Uani 1 1 d . . . . .
C3 C 0.69405(13) 0.42980(12) 0.37935(9) 0.0411(4) Uani 1 1 d . . . . .
C12A C 0.54068(15) 0.34447(11) 0.07921(10) 0.0402(4) Uani 1 1 d . . . . .
C7A C 0.62330(15) 0.51055(11) 0.15096(11) 0.0423(4) Uani 1 1 d . . . . .
C6A C 0.62548(16) 0.57218(10) 0.19628(12) 0.0456(5) Uani 1 1 d . . . . .
C11A C 0.71770(17) 0.40749(12) 0.08991(11) 0.0442(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
O3J C1J 1.3156(19) . ?
O4J C1J 1.209(2) . ?
O1H C1H 1.3169(19) . ?
O3H N7 1.2276(18) . ?
C7H C6H 1.382(2) . ?
C7H C2H 1.397(2) . ?
O2H C1H 1.210(2) . ?
C6H C4H 1.390(2) . ?
N7 O4H 1.2225(18) . ?
N7 C4H 1.4680(19) . ?
C4H C5H 1.387(2) . ?
C3H C5H 1.385(2) . ?
C3H C2H 1.397(2) . ?
C2H C1H 1.503(2) . ?
O2J N1J 1.226(2) . ?
N1J O1J 1.2209(19) . ?
N1J C5J 1.4706(19) . ?
C4J C3J 1.383(2) . ?
C4J C5J 1.389(2) . ?
C7J C6J 1.384(2) . ?
C7J C2J 1.394(2) . ?
C6J C5J 1.385(2) . ?
C3J C2J 1.394(2) . ?
C2J C1J 1.499(2) . ?
O3F C1F 1.2521(19) . ?
O4F C1F 1.2523(19) . ?
C1F C2F 1.5155(19) . ?
C2F C7F 1.391(2) . ?
C2F C3F 1.392(2) . ?
C6F C5F 1.381(2) . ?
C6F C7F 1.385(2) . ?
C3F C4F 1.383(2) . ?
C4F C5F 1.385(2) . ?
O1F N1F 1.196(2) . ?
C5F N1F 1.464(2) . ?
N1F O2F 1.206(3) . ?
O2G C1G 1.3095(19) . ?
O1G C1G 1.2152(19) . ?
O4G N1G 1.2228(18) . ?
N1G O3G 1.2260(18) . ?
N1G C5G 1.4634(19) . ?
C3G C4G 1.386(2) . ?
C3G C2G 1.393(2) . ?
C6G C5G 1.382(2) . ?
C6G C7G 1.386(2) . ?
C1G C2G 1.497(2) . ?
C5G C4G 1.384(2) . ?
C2G C7G 1.387(2) . ?
O3L C1L 1.312(2) . ?
O4L C1L 1.219(2) . ?
C4L C5L 1.384(2) . ?
C4L C3L 1.387(2) . ?
C6L C7L 1.382(2) . ?
C6L C5L 1.383(2) . ?
O1L N1L 1.2251(19) . ?
O2L N1L 1.2279(19) . ?
C7L C2L 1.392(2) . ?
C5L N1L 1.467(2) . ?
C2L C3L 1.393(2) . ?
C2L C1L 1.502(2) . ?
O1K C1K 1.248(2) . ?
O2K C1K 1.249(2) . ?
C2K C7K 1.382(2) . ?
C2K C3K 1.389(2) . ?
C2K C1K 1.513(2) . ?
C4K C5K 1.380(2) . ?
C4K C3K 1.381(2) . ?
O4K N1K 1.230(2) . ?
C7K C6K 1.386(2) . ?
N1K O3K 1.224(2) . ?
N1K C5K 1.468(2) . ?
C5K C6K 1.377(2) . ?
O4I C5I 1.311(2) . ?
N1I O1I 1.2191(19) . ?
N1I O2I 1.2293(19) . ?
N1I C1I 1.4674(19) . ?
O3I C5I 1.210(2) . ?
C3I C2I 1.387(2) . ?
C3I C4I 1.392(2) . ?
C6I C7I 1.384(2) . ?
C6I C4I 1.389(2) . ?
C2I C1I 1.381(2) . ?
C7I C1I 1.378(2) . ?
C4I C5I 1.502(2) . ?
O2D C1D 1.3149(19) . ?
O1D C1D 1.212(2) . ?
O3D N1D 1.2223(19) . ?
N1D O4D 1.2285(19) . ?
N1D C5D 1.4722(19) . ?
C5D C4D 1.381(2) . ?
C5D C6D 1.383(2) . ?
C4D C3D 1.385(2) . ?
C2D C3D 1.393(2) . ?
C2D C7D 1.393(2) . ?
C2D C1D 1.504(2) . ?
C7D C6D 1.387(2) . ?
O1E C1E 1.249(2) . ?
O2E C1E 1.2521(19) . ?
N2C C8C 1.457(2) . ?
N2C C14C 1.471(2) . ?
N2C C13C 1.480(2) . ?
C9C C8C 1.425(2) . ?
C9C C1C 1.425(2) . ?
C9C C10C 1.432(2) . ?
N1C C1C 1.4711(18) . ?
N1C C11C 1.489(2) . ?
N1C C12C 1.494(2) . ?
C4C C3C 1.364(3) . ?
C4C C10C 1.416(2) . ?
C8C C7C 1.372(2) . ?
C2E C3E 1.393(2) . ?
C2E C7E 1.397(2) . ?
C2E C1E 1.506(2) . ?
C5C C6C 1.359(3) . ?
C5C C10C 1.417(2) . ?
C3E C4E 1.384(2) . ?
C1C C2C 1.367(2) . ?
C3C C2C 1.408(2) . ?
C7C C6C 1.411(3) . ?
C7E C6E 1.381(3) . ?
C6E C5E 1.388(3) . ?
C4E C5E 1.377(3) . ?
O4E N1E 1.231(3) . ?
C5E N1E 1.474(2) . ?
O3E N1E 1.209(3) . ?
N1B C1B 1.4687(18) . ?
N1B C11B 1.488(2) . ?
N1B C13B 1.4979(19) . ?
C9B C8B 1.423(2) . ?
C9B C1B 1.427(2) . ?
C9B C10B 1.432(2) . ?
N2B C8B 1.4573(19) . ?
N2B C14B 1.472(2) . ?
N2B C15B 1.476(2) . ?
C1B C2B 1.365(2) . ?
C10B C4B 1.415(2) . ?
C10B C5B 1.416(2) . ?
C4B C3B 1.362(2) . ?
C8B C7B 1.370(2) . ?
C3B C2B 1.407(2) . ?
C7B C6B 1.413(2) . ?
C5B C6B 1.361(3) . ?
N1A C1A 1.4752(19) . ?
N1A C13A 1.492(2) . ?
N1A C14A 1.493(2) . ?
N2A C8A 1.460(2) . ?
N2A C12A 1.472(2) . ?
N2A C11A 1.477(2) . ?
C1A C2A 1.366(2) . ?
C1A C9A 1.421(2) . ?
C9A C8A 1.422(2) . ?
C9A C10A 1.431(2) . ?
C10A C4A 1.415(3) . ?
C10A C5A 1.416(3) . ?
C4A C3 1.356(3) . ?
C8A C7A 1.369(2) . ?
C2A C3 1.407(2) . ?
C5A C6A 1.352(3) . ?
C7A C6A 1.412(3) . ?

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
C6H C7H C2H 120.29(14) . . ?
C7H C6H C4H 118.27(14) . . ?
O4H N7 O3H 123.42(14) . . ?
O4H N7 C4H 118.61(13) . . ?
O3H N7 C4H 117.97(13) . . ?
C5H C4H C6H 122.92(14) . . ?
C5H C4H N7 118.58(13) . . ?
C6H C4H N7 118.50(13) . . ?
C5H C3H C2H 120.56(14) . . ?
C7H C2H C3H 120.00(14) . . ?
C7H C2H C1H 121.92(13) . . ?
C3H C2H C1H 118.06(13) . . ?
C3H C5H C4H 117.96(14) . . ?
O2H C1H O1H 124.68(15) . . ?
O2H C1H C2H 121.74(14) . . ?
O1H C1H C2H 113.58(13) . . ?
O1J N1J O2J 123.42(14) . . ?
O1J N1J C5J 118.34(14) . . ?
O2J N1J C5J 118.25(14) . . ?
C3J C4J C5J 118.34(14) . . ?
C6J C7J C2J 120.59(14) . . ?
C7J C6J C5J 117.92(14) . . ?
C4J C3J C2J 120.14(14) . . ?
C3J C2J C7J 120.13(14) . . ?
C3J C2J C1J 122.03(13) . . ?
C7J C2J C1J 117.81(13) . . ?
O4J C1J O3J 124.48(14) . . ?
O4J C1J C2J 122.12(14) . . ?
O3J C1J C2J 113.39(13) . . ?
C6J C5J C4J 122.87(14) . . ?
C6J C5J N1J 118.44(14) . . ?
C4J C5J N1J 118.69(14) . . ?
O3F C1F O4F 126.92(14) . . ?
O3F C1F C2F 117.15(13) . . ?
O4F C1F C2F 115.93(13) . . ?
C7F C2F C3F 119.55(14) . . ?
C7F C2F C1F 119.93(13) . . ?
C3F C2F C1F 120.51(13) . . ?
C5F C6F C7F 117.93(15) . . ?
C6F C7F C2F 120.76(15) . . ?
C4F C3F C2F 120.71(15) . . ?
C3F C4F C5F 117.97(15) . . ?
C6F C5F C4F 122.99(14) . . ?
C6F C5F N1F 119.17(15) . . ?
C4F C5F N1F 117.83(15) . . ?
O1F N1F O2F 121.84(17) . . ?
O1F N1F C5F 119.61(17) . . ?
O2F N1F C5F 118.54(16) . . ?
O4G N1G O3G 123.34(14) . . ?
O4G N1G C5G 118.36(13) . . ?
O3G N1G C5G 118.30(13) . . ?
C4G C3G C2G 120.24(14) . . ?
C5G C6G C7G 117.91(14) . . ?
O1G C1G O2G 124.60(14) . . ?
O1G C1G C2G 121.54(14) . . ?
O2G C1G C2G 113.86(12) . . ?
C6G C5G C4G 123.12(14) . . ?
C6G C5G N1G 118.33(13) . . ?
C4G C5G N1G 118.55(13) . . ?
C7G C2G C3G 120.14(14) . . ?
C7G C2G C1G 117.95(13) . . ?
C3G C2G C1G 121.90(13) . . ?
C5G C4G C3G 118.02(14) . . ?
C6G C7G C2G 120.57(14) . . ?
C5L C4L C3L 117.97(14) . . ?
C7L C6L C5L 117.93(15) . . ?
C6L C7L C2L 120.48(14) . . ?
C6L C5L C4L 123.27(14) . . ?
C6L C5L N1L 118.24(14) . . ?
C4L C5L N1L 118.48(14) . . ?
C7L C2L C3L 120.22(14) . . ?
C7L C2L C1L 117.82(14) . . ?
C3L C2L C1L 121.90(14) . . ?
O1L N1L O2L 123.51(14) . . ?
O1L N1L C5L 118.15(14) . . ?
O2L N1L C5L 118.34(14) . . ?
O4L C1L O3L 124.81(15) . . ?
O4L C1L C2L 121.63(15) . . ?
O3L C1L C2L 113.56(14) . . ?
C4L C3L C2L 120.12(14) . . ?
C7K C2K C3K 119.52(14) . . ?
C7K C2K C1K 120.52(14) . . ?
C3K C2K C1K 119.96(14) . . ?
C5K C4K C3K 118.08(15) . . ?
C2K C7K C6K 120.78(15) . . ?
O1K C1K O2K 126.75(15) . . ?
O1K C1K C2K 116.78(14) . . ?
O2K C1K C2K 116.47(14) . . ?
O3K N1K O4K 123.99(16) . . ?
O3K N1K C5K 118.25(16) . . ?
O4K N1K C5K 117.76(16) . . ?
C4K C3K C2K 120.68(15) . . ?
C6K C5K C4K 122.73(15) . . ?
C6K C5K N1K 118.24(15) . . ?
C4K C5K N1K 119.03(15) . . ?
C5K C6K C7K 118.02(16) . . ?
O1I N1I O2I 123.68(14) . . ?
O1I N1I C1I 118.38(13) . . ?
O2I N1I C1I 117.94(14) . . ?
C2I C3I C4I 120.23(14) . . ?
C7I C6I C4I 120.23(15) . . ?
C1I C2I C3I 117.89(14) . . ?
C1I C7I C6I 118.14(15) . . ?
C6I C4I C3I 120.25(14) . . ?
C6I C4I C5I 118.57(14) . . ?
C3I C4I C5I 121.17(14) . . ?
C7I C1I C2I 123.27(14) . . ?
C7I C1I N1I 118.29(14) . . ?
C2I C1I N1I 118.44(14) . . ?
O3I C5I O4I 125.38(15) . . ?
O3I C5I C4I 122.28(15) . . ?
O4I C5I C4I 112.32(13) . . ?
O3D N1D O4D 123.76(14) . . ?
O3D N1D C5D 118.26(13) . . ?
O4D N1D C5D 117.98(14) . . ?
C4D C5D C6D 123.31(14) . . ?
C4D C5D N1D 117.97(14) . . ?
C6D C5D N1D 118.73(14) . . ?
C5D C4D C3D 118.11(14) . . ?
C3D C2D C7D 120.22(14) . . ?
C3D C2D C1D 120.93(13) . . ?
C7D C2D C1D 118.79(14) . . ?
C6D C7D C2D 120.29(15) . . ?
C5D C6D C7D 117.87(14) . . ?
C4D C3D C2D 120.19(14) . . ?
O1D C1D O2D 124.37(14) . . ?
O1D C1D C2D 122.11(14) . . ?
O2D C1D C2D 113.52(13) . . ?
C8C N2C C14C 112.95(13) . . ?
C8C N2C C13C 112.15(13) . . ?
C14C N2C C13C 111.79(14) . . ?
C8C C9C C1C 125.31(14) . . ?
C8C C9C C10C 117.99(14) . . ?
C1C C9C C10C 116.70(14) . . ?
C1C N1C C11C 112.49(12) . . ?
C1C N1C C12C 112.38(12) . . ?
C11C N1C C12C 112.00(13) . . ?
C3C C4C C10C 121.15(15) . . ?
C7C C8C C9C 120.23(15) . . ?
C7C C8C N2C 120.99(15) . . ?
C9C C8C N2C 118.77(13) . . ?
C3E C2E C7E 119.69(14) . . ?
C3E C2E C1E 119.84(14) . . ?
C7E C2E C1E 120.46(14) . . ?
C6C C5C C10C 120.67(16) . . ?
C4E C3E C2E 120.82(15) . . ?
C4C C10C C5C 120.41(15) . . ?
C4C C10C C9C 119.82(14) . . ?
C5C C10C C9C 119.76(15) . . ?
C2C C1C C9C 122.21(14) . . ?
C2C C1C N1C 119.40(14) . . ?
C9C C1C N1C 118.38(13) . . ?
C4C C3C C2C 119.95(15) . . ?
O1E C1E O2E 127.02(14) . . ?
O1E C1E C2E 116.75(13) . . ?
O2E C1E C2E 116.22(13) . . ?
C8C C7C C6C 121.26(17) . . ?
C6E C7E C2E 120.21(17) . . ?
C7E C6E C5E 118.28(16) . . ?
C5E C4E C3E 117.86(16) . . ?
C5C C6C C7C 120.07(16) . . ?
C1C C2C C3C 120.16(15) . . ?
C4E C5E C6E 123.09(15) . . ?
C4E C5E N1E 117.34(18) . . ?
C6E C5E N1E 119.57(17) . . ?
O3E N1E O4E 123.75(19) . . ?
O3E N1E C5E 118.3(2) . . ?
O4E N1E C5E 117.96(18) . . ?
C1B N1B C11B 113.48(12) . . ?
C1B N1B C13B 110.67(11) . . ?
C11B N1B C13B 112.31(12) . . ?
C8B C9B C1B 125.36(13) . . ?
C8B C9B C10B 118.08(13) . . ?
C1B C9B C10B 116.56(13) . . ?
C8B N2B C14B 112.41(13) . . ?
C8B N2B C15B 112.39(12) . . ?
C14B N2B C15B 112.08(13) . . ?
C2B C1B C9B 122.27(13) . . ?
C2B C1B N1B 119.32(13) . . ?
C9B C1B N1B 118.35(13) . . ?
C4B C10B C5B 120.80(14) . . ?
C4B C10B C9B 119.66(14) . . ?
C5B C10B C9B 119.53(14) . . ?
C3B C4B C10B 121.49(14) . . ?
C7B C8B C9B 120.50(14) . . ?
C7B C8B N2B 120.64(14) . . ?
C9B C8B N2B 118.86(13) . . ?
C4B C3B C2B 119.73(15) . . ?
C8B C7B C6B 121.02(16) . . ?
C6B C5B C10B 120.87(15) . . ?
C1B C2B C3B 120.29(15) . . ?
C5B C6B C7B 119.99(15) . . ?
C1A N1A C13A 112.68(12) . . ?
C1A N1A C14A 112.08(12) . . ?
C13A N1A C14A 112.31(13) . . ?
C8A N2A C12A 112.08(13) . . ?
C8A N2A C11A 112.33(13) . . ?
C12A N2A C11A 111.78(15) . . ?
C2A C1A C9A 122.07(15) . . ?
C2A C1A N1A 119.25(15) . . ?
C9A C1A N1A 118.67(14) . . ?
C1A C9A C8A 125.44(14) . . ?
C1A C9A C10A 116.68(15) . . ?
C8A C9A C10A 117.84(15) . . ?
C4A C10A C5A 120.57(15) . . ?
C4A C10A C9A 119.70(16) . . ?
C5A C10A C9A 119.68(17) . . ?
C3 C4A C10A 121.33(15) . . ?
C7A C8A C9A 120.51(15) . . ?
C7A C8A N2A 120.73(16) . . ?
C9A C8A N2A 118.75(14) . . ?
C1A C2A C3 120.32(17) . . ?
C6A C5A C10A 120.76(16) . . ?
C4A C3 C2A 119.86(17) . . ?
C8A C7A C6A 121.02(19) . . ?
C5A C6A C7A 120.17(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6J H4J O1L 0.97(2) 2.64(2) 3.605(2) 173.8(17) 2_676
C11C H13C O4J 0.97(2) 2.34(2) 3.254(2) 156.7(16) 2_565
C6L H3L O2I 0.94(2) 2.62(2) 3.531(2) 163.0(16) 2_776
C6G H4G O3H 0.93(2) 2.51(2) 3.3818(19) 155.9(16) 2_666
C11B H8B O4E 0.99(2) 2.45(2) 3.333(2) 148.9(15) 2_565
C13A H11A O2F 0.94(2) 2.52(2) 3.411(2) 156.7(15) 2_655
C13B H11B O4E 0.98(2) 2.45(2) 3.351(2) 152.2(16) 2_565
C12C H9C O3K 0.98(2) 2.51(2) 3.467(2) 165.7(17) 1_455
C13B H12B O4L 0.98(2) 2.45(2) 3.380(2) 159.4(15) 1_455
C11B H9B O2H 0.95(2) 2.32(2) 3.233(2) 163.0(17) 1_565
C12C H10C O3I 0.99(2) 2.52(2) 3.180(2) 123.7(15) 2_665
C11C H12C O3H 0.99(2) 2.63(2) 3.405(2) 135.1(15) 1_454
C13A H13A O1G 0.97(2) 2.41(2) 3.293(2) 151.3(15) .
C12C H8C O2D 0.97(2) 2.56(2) 3.508(2) 168.9(16) 2_565
C14A H10A O2F 1.01(2) 2.47(2) 3.409(2) 153.9(16) 2_655
C2C H2C O3G 0.98(2) 2.55(2) 3.472(2) 157.0(16) 2_565
C13B H13B O3J 1.02(2) 2.60(2) 3.2798(19) 123.5(15) 1_455
C15B H18B O2H 1.03(2) 2.55(2) 3.541(2) 161.1(16) 1_565
C2A H2A O2L 0.95(2) 2.61(2) 3.466(2) 149.9(16) 1_545
C12A H14A O1F 0.99(2) 2.49(2) 3.346(2) 143.9(17) 2_655
C2B H2B O4D 0.97(2) 2.61(2) 3.442(2) 143.8(15) .
C14A H8A O2I 1.01(2) 2.52(2) 3.388(2) 143.7(17) 2_766
C14A H9A O4I 0.96(2) 2.54(2) 3.431(2) 153.7(18) .
C12A H16A O1G 1.02(2) 2.50(2) 3.437(2) 152.8(18) .
C4F H3F O4L 0.99(2) 2.52(2) 3.465(2) 159.6(18) 2_665
C13C H19C O4J 1.00(2) 2.52(2) 3.477(2) 158.7(18) 2_565
O4I H1I O2E 0.93(3) 1.60(3) 2.5266(15) 171(3) 1_655
O2D H1D O1E 1.02(3) 1.51(3) 2.5308(15) 174(3) .
O2G H5G O3F 0.97(3) 1.58(3) 2.5460(15) 176(2) .
C14C H15C O4K 1.00(2) 2.65(2) 3.472(2) 138.9(17) 1_455
O1H H1H O4F 1.00(3) 1.54(3) 2.5432(15) 174(3) .
O3J H1J O1K 0.96(3) 1.59(3) 2.5392(15) 167(3) .
O3L H1L O2K 0.97(3) 1.54(3) 2.5115(17) 177(3) .
N1C H1C N2C 1.05(2) 1.60(2) 2.5965(18) 156.7(19) .
N1B H1 N2B 0.99(2) 1.66(2) 2.6007(18) 157(2) .
N1A H1A N2A 1.01(2) 1.64(2) 2.6012(19) 157.4(19) .

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'slow evaporation from methanol solvent at 30 degreesC'
####################################################################### 
# 
# 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_complex_4
_database_code_depnum_ccdc_archive 'CCDC 1831643'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT353_complex_4           
;
PROBLEM: Long N-H (N0.87,N1.01A) N1 - H1 .. 1.13 Ang.
RESPONSE: H1 is in a short, strong N-H...N hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'DMAN 3-methoxy benzoic acid 3-methoxybenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N2, C8 H8 O3, C8 H7 O3'
_chemical_formula_sum            'C30 H34 N2 O6'
_chemical_formula_weight         518.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 '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 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.8917(4)
_cell_length_b                   23.8954(9)
_cell_length_c                   12.0958(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.040(2)
_cell_angle_gamma                90
_cell_volume                     2650.10(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      33.35

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction  
;

_exptl_special_details           
;
 ?
;

_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_detector                 'CMOS Detector'
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_reflns_number            37258
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         33.661
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5439
_reflns_number_gt                3754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.3638P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5439
_refine_ls_number_parameters     479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H10 H -0.0649(18) 0.7140(8) 0.8965(15) 0.027(5) Uiso 1 1 d . . . . .
H15 H 0.2909(19) 0.7273(8) 1.2376(16) 0.032(5) Uiso 1 1 d . . . . .
H12 H 0.1887(17) 0.6767(7) 0.8359(16) 0.019(4) Uiso 1 1 d . . . . .
H14 H 0.348(2) 0.6772(8) 1.3355(18) 0.033(5) Uiso 1 1 d . . . . .
H4 H 0.2674(19) 0.4405(8) 1.1833(16) 0.035(5) Uiso 1 1 d . . . . .
H16 H 0.385(2) 0.6752(8) 1.2165(16) 0.034(5) Uiso 1 1 d . . . . .
H13 H 0.302(2) 0.6765(7) 0.9737(15) 0.027(5) Uiso 1 1 d . . . . .
H2 H 0.2514(17) 0.5837(7) 1.3634(15) 0.015(4) Uiso 1 1 d . . . . .
H5 H 0.1944(17) 0.4417(8) 0.9685(14) 0.021(5) Uiso 1 1 d . . . . .
H9 H -0.1249(19) 0.6512(8) 0.9111(15) 0.031(5) Uiso 1 1 d . . . . .
H17 H 0.0397(19) 0.7112(8) 1.2223(15) 0.031(5) Uiso 1 1 d . . . . .
H18 H 0.094(2) 0.6617(8) 1.3212(18) 0.039(6) Uiso 1 1 d . . . . .
H8 H -0.0761(19) 0.6633(7) 0.8012(17) 0.028(5) Uiso 1 1 d . . . . .
H6 H 0.1072(17) 0.4901(7) 0.7869(15) 0.021(5) Uiso 1 1 d . . . . .
H7 H 0.0667(18) 0.5866(7) 0.7843(16) 0.024(5) Uiso 1 1 d . . . . .
H11 H 0.1911(19) 0.7287(8) 0.9277(16) 0.031(5) Uiso 1 1 d . . . . .
H3 H 0.3027(19) 0.4877(8) 1.3650(16) 0.029(5) Uiso 1 1 d . . . . .
H19 H -0.032(2) 0.6488(8) 1.1919(17) 0.039(6) Uiso 1 1 d . . . . .
H1 H 0.124(2) 0.6656(9) 1.0555(19) 0.059(7) Uiso 1 1 d . . . . .
N1 N 0.09732(14) 0.65707(5) 0.95746(12) 0.0165(3) Uani 1 1 d . . . . .
N2 N 0.17200(14) 0.65564(6) 1.18670(12) 0.0179(3) Uani 1 1 d . . . . .
C3 C 0.12494(19) 0.50978(7) 0.86113(17) 0.0224(4) Uani 1 1 d . . . . .
C9 C 0.16999(16) 0.56883(7) 1.07438(14) 0.0159(4) Uani 1 1 d . . . . .
C10 C 0.19621(16) 0.50985(7) 1.07529(15) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.09809(18) 0.56751(7) 0.85891(16) 0.0207(4) Uani 1 1 d . . . . .
C1 C 0.12114(17) 0.59613(7) 0.96141(15) 0.0163(4) Uani 1 1 d . . . . .
C6 C 0.26658(19) 0.50736(8) 1.28899(17) 0.0240(4) Uani 1 1 d . . . . .
C4 C 0.17283(18) 0.48186(8) 0.96661(16) 0.0200(4) Uani 1 1 d . . . . .
C7 C 0.23975(19) 0.56520(8) 1.28918(16) 0.0226(4) Uani 1 1 d . . . . .
C8 C 0.19491(17) 0.59530(7) 1.18565(15) 0.0172(4) Uani 1 1 d . . . . .
C5 C 0.24643(18) 0.48079(8) 1.18491(16) 0.0209(4) Uani 1 1 d . . . . .
C14 C 0.2041(2) 0.68768(8) 0.91951(18) 0.0236(4) Uani 1 1 d . . . . .
C11 C 0.0595(2) 0.67032(9) 1.23466(18) 0.0255(4) Uani 1 1 d . . . . .
C12 C 0.3095(2) 0.68612(8) 1.25012(19) 0.0260(4) Uani 1 1 d . . . . .
C13 C -0.05472(19) 0.67337(9) 0.88320(18) 0.0237(4) Uani 1 1 d . . . . .
H29 H 0.1648(18) 1.0056(7) 1.0859(14) 0.021(4) Uiso 1 1 d . . . . .
H31 H 0.3273(17) 0.8196(7) 1.0936(14) 0.021(5) Uiso 1 1 d . . . . .
H30 H 0.0022(17) 0.9303(6) 1.0622(13) 0.013(4) Uiso 1 1 d . . . . .
H32 H 0.5849(17) 0.8169(7) 1.1774(15) 0.022(5) Uiso 1 1 d . . . . .
H34 H 0.6903(19) 0.8468(7) 1.1172(14) 0.020(4) Uiso 1 1 d . . . . .
H33 H 0.5318(19) 0.8235(7) 1.0323(16) 0.029(5) Uiso 1 1 d . . . . .
H28 H 0.4105(18) 0.9863(7) 1.1157(14) 0.021(5) Uiso 1 1 d . . . . .
O2 O -0.07179(12) 0.83110(5) 1.07449(10) 0.0222(3) Uani 1 1 d . . . . .
O1 O 0.09529(13) 0.77141(5) 1.06167(11) 0.0268(3) Uani 1 1 d . . . . .
O3 O 0.53375(12) 0.89626(5) 1.11763(11) 0.0233(3) Uani 1 1 d . . . . .
C28 C 0.39104(17) 0.90173(7) 1.10451(14) 0.0175(4) Uani 1 1 d . . . . .
C25 C 0.10363(19) 0.92271(7) 1.07526(14) 0.0174(4) Uani 1 1 d . . . . .
C24 C 0.15194(17) 0.86805(7) 1.07833(14) 0.0156(4) Uani 1 1 d . . . . .
C27 C 0.34354(19) 0.95664(7) 1.10484(15) 0.0196(4) Uani 1 1 d . . . . .
C23 C 0.05209(17) 0.81910(7) 1.07013(14) 0.0166(4) Uani 1 1 d . . . . .
C26 C 0.20020(18) 0.96683(7) 1.08896(15) 0.0191(4) Uani 1 1 d . . . . .
C30 C 0.5877(2) 0.84110(8) 1.11187(18) 0.0225(4) Uani 1 1 d . . . . .
C29 C 0.29606(18) 0.85765(7) 1.09183(14) 0.0167(4) Uani 1 1 d . . . . .
H22 H -0.4727(16) 0.6507(6) 0.8326(14) 0.012(4) Uiso 1 1 d . . . . .
H23 H -0.3000(17) 0.6810(7) 1.1926(15) 0.021(5) Uiso 1 1 d . . . . .
H20 H -0.5340(17) 0.5382(7) 1.0637(14) 0.016(4) Uiso 1 1 d . . . . .
H24 H -0.3382(19) 0.6553(8) 1.3592(15) 0.031(5) Uiso 1 1 d . . . . .
H21 H -0.5725(19) 0.5646(8) 0.8668(16) 0.031(5) Uiso 1 1 d . . . . .
H26 H -0.2036(19) 0.6154(7) 1.3592(15) 0.023(5) Uiso 1 1 d . . . . .
H25 H -0.313(2) 0.5953(8) 1.4272(17) 0.035(5) Uiso 1 1 d . . . . .
H27 H -0.160(3) 0.7811(11) 1.069(2) 0.078(8) Uiso 1 1 d . . . . .
O6 O -0.40186(13) 0.58541(5) 1.25430(10) 0.0235(3) Uani 1 1 d . . . . .
O4 O -0.21698(12) 0.74773(5) 1.08272(10) 0.0217(3) Uani 1 1 d . . . . .
O5 O -0.34558(13) 0.74409(5) 0.88578(11) 0.0275(3) Uani 1 1 d . . . . .
C19 C -0.49484(18) 0.57202(7) 1.04832(16) 0.0190(4) Uani 1 1 d . . . . .
C21 C -0.45704(18) 0.63824(7) 0.91413(16) 0.0197(4) Uani 1 1 d . . . . .
C17 C -0.35454(18) 0.65556(7) 1.12648(16) 0.0177(4) Uani 1 1 d . . . . .
C18 C -0.41495(17) 0.60542(7) 1.14495(15) 0.0172(4) Uani 1 1 d . . . . .
C20 C -0.51554(18) 0.58836(7) 0.93381(16) 0.0202(4) Uani 1 1 d . . . . .
C15 C -0.31149(18) 0.72519(7) 0.98653(16) 0.0189(4) Uani 1 1 d . . . . .
C16 C -0.37638(17) 0.67170(7) 1.01002(15) 0.0170(4) Uani 1 1 d . . . . .
C22 C -0.3070(2) 0.61544(8) 1.35658(17) 0.0253(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
N1 C1 1.473(2) . ?
N1 C13 1.485(2) . ?
N1 C14 1.491(2) . ?
N2 C8 1.460(2) . ?
N2 C11 1.477(2) . ?
N2 C12 1.479(2) . ?
C3 C4 1.358(2) . ?
C3 C2 1.403(2) . ?
C9 C8 1.422(2) . ?
C9 C1 1.425(2) . ?
C9 C10 1.432(2) . ?
C10 C5 1.412(2) . ?
C10 C4 1.415(2) . ?
C2 C1 1.358(2) . ?
C6 C5 1.356(2) . ?
C6 C7 1.408(3) . ?
C7 C8 1.366(2) . ?
O2 C23 1.2787(19) . ?
O1 C23 1.2346(19) . ?
O3 C28 1.3663(19) . ?
O3 C30 1.433(2) . ?
C28 C29 1.381(2) . ?
C28 C27 1.394(2) . ?
C25 C24 1.386(2) . ?
C25 C26 1.390(2) . ?
C24 C29 1.395(2) . ?
C24 C23 1.510(2) . ?
C27 C26 1.379(2) . ?
O6 C18 1.3662(19) . ?
O6 C22 1.433(2) . ?
O4 C15 1.304(2) . ?
O5 C15 1.222(2) . ?
C19 C20 1.378(2) . ?
C19 C18 1.391(2) . ?
C21 C20 1.384(2) . ?
C21 C16 1.388(2) . ?
C17 C18 1.394(2) . ?
C17 C16 1.397(2) . ?
C15 C16 1.504(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 113.08(13) . . ?
C1 N1 C14 111.82(13) . . ?
C13 N1 C14 111.00(14) . . ?
C8 N2 C11 112.34(14) . . ?
C8 N2 C12 112.05(13) . . ?
C11 N2 C12 111.17(15) . . ?
C4 C3 C2 119.86(17) . . ?
C8 C9 C1 125.43(15) . . ?
C8 C9 C10 117.62(15) . . ?
C1 C9 C10 116.95(14) . . ?
C5 C10 C4 121.16(16) . . ?
C5 C10 C9 119.35(15) . . ?
C4 C10 C9 119.48(15) . . ?
C1 C2 C3 120.79(17) . . ?
C2 C1 C9 121.68(16) . . ?
C2 C1 N1 119.88(15) . . ?
C9 C1 N1 118.44(14) . . ?
C5 C6 C7 119.94(17) . . ?
C3 C4 C10 121.24(17) . . ?
C8 C7 C6 120.81(17) . . ?
C7 C8 C9 120.99(16) . . ?
C7 C8 N2 120.67(15) . . ?
C9 C8 N2 118.35(14) . . ?
C6 C5 C10 121.26(17) . . ?
C28 O3 C30 118.02(13) . . ?
O3 C28 C29 124.74(15) . . ?
O3 C28 C27 115.12(14) . . ?
C29 C28 C27 120.14(16) . . ?
C24 C25 C26 119.78(16) . . ?
C25 C24 C29 119.86(15) . . ?
C25 C24 C23 121.17(15) . . ?
C29 C24 C23 118.95(14) . . ?
C26 C27 C28 119.72(16) . . ?
O1 C23 O2 125.26(15) . . ?
O1 C23 C24 118.83(14) . . ?
O2 C23 C24 115.90(14) . . ?
C27 C26 C25 120.48(16) . . ?
C28 C29 C24 119.98(16) . . ?
C18 O6 C22 116.99(14) . . ?
C20 C19 C18 120.34(16) . . ?
C20 C21 C16 119.92(16) . . ?
C18 C17 C16 119.05(16) . . ?
O6 C18 C19 115.48(15) . . ?
O6 C18 C17 124.44(15) . . ?
C19 C18 C17 120.08(16) . . ?
C19 C20 C21 120.18(17) . . ?
O5 C15 O4 125.03(16) . . ?
O5 C15 C16 121.63(15) . . ?
O4 C15 C16 113.34(15) . . ?
C21 C16 C17 120.43(16) . . ?
C21 C16 C15 118.94(15) . . ?
C17 C16 C15 120.63(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H15 O1 1.001(19) 2.509(18) 3.196(2) 125.5(13) .
C11 H17 O1 0.996(19) 2.636(18) 3.301(2) 124.2(13) .
C11 H17 O4 0.996(19) 2.616(18) 3.242(2) 120.9(13) .
C14 H11 O1 0.998(19) 2.391(19) 3.083(2) 125.8(14) .
N1 H1 N2 1.13(2) 1.49(2) 2.5881(19) 159.9(19) .
C30 H34 O2 1.002(17) 2.618(18) 3.571(2) 158.7(13) 1_655
C22 H24 O5 1.005(19) 2.43(2) 3.412(2) 165.0(14) 4_576
O2 H27 O5 1.47(3) 2.45(2) 3.4970(16) 124.7(14) .
O4 H27 O2 1.02(3) 1.47(3) 2.4797(16) 168(2) .
O4 H27 O1 1.02(3) 2.57(3) 3.2429(16) 122.8(17) .

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'slow evaporation from acetonitrile solvent at 4 degreesC'
