# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_N-Phenyl-p-phenylenediamine+diglycolic
_database_code_depnum_ccdc_archive 'CCDC 1435836'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'N-Phenyl-p-phenylenediamine+diglycolic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H12 N2), 2(C4 H6 O5)'
_chemical_formula_sum            'C32 H36 N4 O10'
_chemical_formula_weight         636.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 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                   19.0949(19)
_cell_length_b                   9.2904(9)
_cell_length_c                   17.9875(19)
_cell_angle_alpha                90
_cell_angle_beta                 110.543(5)
_cell_angle_gamma                90
_cell_volume                     2988.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      25.97

_exptl_crystal_description       Plate
_exptl_crystal_colour            Bluish-black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5559
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   INCOATECImuSMo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47123
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.139
_diffrn_reflns_theta_max         26.079
_diffrn_reflns_theta_full        25.242
_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             5913
_reflns_number_gt                4108
_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-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         5913
_refine_ls_number_parameters     555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.2424
_refine_ls_wR_factor_gt          0.1760
_refine_ls_goodness_of_fit_ref   1.632
_refine_ls_restrained_S_all      1.632
_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
C1 C 0.27155(16) 0.6451(3) 0.32221(18) 0.0187(7) Uani 1 1 d . . . . .
C2 C 0.26361(18) 0.7636(3) 0.3651(2) 0.0264(7) Uani 1 1 d . . . . .
H2 H 0.3041(19) 0.783(3) 0.415(2) 0.034(9) Uiso 1 1 d . . . . .
C3 C 0.20114(18) 0.8489(3) 0.3344(2) 0.0313(8) Uani 1 1 d . . . . .
H3 H 0.191(2) 0.923(4) 0.363(2) 0.044(10) Uiso 1 1 d . . . . .
C4 C 0.14563(17) 0.8178(3) 0.26134(19) 0.0242(7) Uani 1 1 d . . . . .
C5 C 0.15543(18) 0.6978(3) 0.2202(2) 0.0266(7) Uani 1 1 d . . . . .
H5 H 0.1177(17) 0.678(3) 0.169(2) 0.021(8) Uiso 1 1 d . . . . .
C6 C 0.21772(18) 0.6119(3) 0.2507(2) 0.0253(7) Uani 1 1 d . . . . .
H6 H 0.2227(15) 0.532(3) 0.2220(18) 0.014(7) Uiso 1 1 d . . . . .
C7 C 0.01057(17) 0.8799(3) 0.18738(19) 0.0241(7) Uani 1 1 d . . . . .
C8 C -0.01889(18) 0.7419(3) 0.1711(2) 0.0273(7) Uani 1 1 d . . . . .
H8 H 0.0119(18) 0.655(4) 0.185(2) 0.033(9) Uiso 1 1 d . . . . .
C9 C -0.09466(19) 0.7220(4) 0.1318(2) 0.0305(8) Uani 1 1 d . . . . .
H9 H -0.1126(19) 0.628(4) 0.123(2) 0.039(10) Uiso 1 1 d . . . . .
C10 C -0.1425(2) 0.8376(4) 0.1087(2) 0.0356(9) Uani 1 1 d . . . . .
H10 H -0.196(2) 0.827(4) 0.080(2) 0.049(11) Uiso 1 1 d . . . . .
C11 C -0.11411(19) 0.9757(4) 0.1233(2) 0.0304(8) Uani 1 1 d . . . . .
H11 H -0.1480(18) 1.063(4) 0.108(2) 0.031(9) Uiso 1 1 d . . . . .
C12 C -0.03866(19) 0.9973(3) 0.16156(19) 0.0269(7) Uani 1 1 d . . . . .
H12 H -0.0169(19) 1.098(4) 0.174(2) 0.041(10) Uiso 1 1 d . . . . .
C13 C 0.28557(16) 0.6020(3) 0.08231(18) 0.0202(7) Uani 1 1 d . . . . .
C14 C 0.22359(17) 0.5135(3) 0.05760(19) 0.0241(7) Uani 1 1 d . . . . .
H14A H 0.2298 0.4121 0.0573 0.029 Uiso 1 1 calc R U . . .
C15 C 0.15249(18) 0.5719(3) 0.03321(19) 0.0235(7) Uani 1 1 d . . . . .
H15 H 0.1081(19) 0.506(4) 0.019(2) 0.040(10) Uiso 1 1 d . . . . .
C16 C 0.14316(18) 0.7208(3) 0.0339(2) 0.0272(7) Uani 1 1 d . . . . .
C17 C 0.20607(17) 0.8086(3) 0.0562(2) 0.0268(7) Uani 1 1 d . . . . .
H17 H 0.1988(16) 0.916(3) 0.0578(18) 0.025(8) Uiso 1 1 d . . . . .
C18 C 0.27729(19) 0.7511(3) 0.0815(2) 0.0272(8) Uani 1 1 d . . . . .
H18 H 0.3214(19) 0.818(4) 0.097(2) 0.037(10) Uiso 1 1 d . . . . .
C19 C 0.00504(17) 0.7545(3) -0.04069(19) 0.0222(7) Uani 1 1 d . . . . .
C20 C -0.05807(18) 0.8265(3) -0.0391(2) 0.0278(7) Uani 1 1 d . . . . .
H20 H -0.0555(15) 0.885(3) 0.0070(18) 0.013(7) Uiso 1 1 d . . . . .
C21 C -0.12580(18) 0.8121(3) -0.1009(2) 0.0302(8) Uani 1 1 d . . . . .
H21 H -0.1722(18) 0.869(3) -0.101(2) 0.031(9) Uiso 1 1 d . . . . .
C22 C -0.13170(19) 0.7244(3) -0.1651(2) 0.0301(8) Uani 1 1 d . . . . .
H22 H -0.1778(19) 0.718(3) -0.210(2) 0.027(9) Uiso 1 1 d . . . . .
C23 C -0.06950(18) 0.6494(3) -0.1658(2) 0.0276(8) Uani 1 1 d . . . . .
H23 H -0.0735(17) 0.581(3) -0.209(2) 0.030(9) Uiso 1 1 d . . . . .
C24 C -0.00166(18) 0.6625(3) -0.10441(19) 0.0251(7) Uani 1 1 d . . . . .
H24 H 0.0419(17) 0.611(3) -0.1118(19) 0.024(8) Uiso 1 1 d . . . . .
C25 C 0.45716(17) 0.7471(3) 0.00892(19) 0.0242(7) Uani 1 1 d . . . . .
C26 C 0.47981(18) 0.8438(3) 0.08080(19) 0.0240(7) Uani 1 1 d . . . . .
H26B H 0.4510(18) 0.942(4) 0.068(2) 0.031(9) Uiso 1 1 d . . . . .
H26A H 0.535(2) 0.862(4) 0.097(2) 0.041(10) Uiso 1 1 d . . . . .
C27 C 0.47743(18) 0.8681(3) 0.2097(2) 0.0238(7) Uani 1 1 d . . . . .
H27B H 0.445(2) 0.957(4) 0.197(2) 0.045(10) Uiso 1 1 d . . . . .
C28 C 0.45887(16) 0.7913(3) 0.27422(19) 0.0212(7) Uani 1 1 d . . . . .
C29 C 0.33862(16) 0.2064(3) 0.24995(18) 0.0202(7) Uani 1 1 d . . . . .
C30 C 0.3455(2) 0.1385(3) 0.3273(2) 0.0276(8) Uani 1 1 d . . . . .
H30B H 0.3965(19) 0.089(3) 0.349(2) 0.029(9) Uiso 1 1 d . . . . .
H30A H 0.307(2) 0.072(4) 0.316(2) 0.039(10) Uiso 1 1 d . . . . .
C31 C 0.34526(19) 0.1871(3) 0.45436(18) 0.0218(7) Uani 1 1 d . . . . .
H31A H 0.3940(15) 0.140(3) 0.4784(17) 0.008(7) Uiso 1 1 d . . . . .
H31B H 0.3080(17) 0.109(3) 0.4546(19) 0.024(8) Uiso 1 1 d . . . . .
C32 C 0.34104(16) 0.3038(3) 0.51152(18) 0.0201(7) Uani 1 1 d . . . . .
N1 N 0.33611(15) 0.5505(3) 0.35475(17) 0.0218(6) Uani 1 1 d . . . . .
H1X H 0.375(2) 0.596(4) 0.365(2) 0.029(10) Uiso 1 1 d . . . . .
N2 N 0.08487(15) 0.9117(3) 0.23058(19) 0.0336(7) Uani 1 1 d . . . . .
H2W H 0.0910(18) 1.006(4) 0.243(2) 0.031(9) Uiso 1 1 d . . . . .
N3 N 0.36092(15) 0.5424(3) 0.11285(17) 0.0224(6) Uani 1 1 d . . . . .
H3Y H 0.3844(19) 0.571(4) 0.084(2) 0.031(10) Uiso 1 1 d . . . . .
N4 N 0.07295(15) 0.7845(3) 0.01955(17) 0.0300(7) Uani 1 1 d . . . . .
H4W H 0.0781(19) 0.863(4) 0.044(2) 0.037(10) Uiso 1 1 d . . . . .
O1 O 0.42487(13) 0.6308(2) 0.00800(13) 0.0298(6) Uani 1 1 d . . . . .
O2 O 0.47270(12) 0.7964(2) -0.04985(13) 0.0294(6) Uani 1 1 d . . . . .
O3 O 0.48128(13) 0.8626(2) 0.34075(15) 0.0304(6) Uani 1 1 d . . . . .
H3W H 0.473(2) 0.822(4) 0.385(3) 0.052(12) Uiso 1 1 d . . . . .
O4 O 0.42578(12) 0.6768(2) 0.26432(12) 0.0260(5) Uani 1 1 d . . . . .
O5 O 0.46336(12) 0.7771(2) 0.14387(12) 0.0243(5) Uani 1 1 d . . . . .
O6 O 0.33399(12) 0.4326(2) 0.49224(12) 0.0260(5) Uani 1 1 d . . . . .
O7 O 0.34321(12) 0.2557(2) 0.57863(13) 0.0252(5) Uani 1 1 d . . . . .
O8 O 0.33796(13) 0.1116(2) 0.19582(14) 0.0302(6) Uani 1 1 d . . . . .
H8W H 0.337(2) 0.159(5) 0.147(3) 0.069(14) Uiso 1 1 d . . . . .
O9 O 0.33476(12) 0.3367(2) 0.23882(12) 0.0241(5) Uani 1 1 d . . . . .
O10 O 0.33684(12) 0.24475(19) 0.37936(12) 0.0238(5) Uani 1 1 d . . . . .
H27A H 0.5310(18) 0.894(3) 0.233(2) 0.027(9) Uiso 1 1 d . . . . .
H3Z H 0.361(2) 0.446(5) 0.114(2) 0.047(11) Uiso 1 1 d . . . . .
H3X H 0.387(2) 0.580(4) 0.171(2) 0.050(11) Uiso 1 1 d . . . . .
H1Z H 0.340(2) 0.481(4) 0.319(2) 0.053(12) Uiso 1 1 d . . . . .
H1Y H 0.334(2) 0.497(5) 0.408(3) 0.073(14) 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
C1 C6 1.371(4) . ?
C1 C2 1.383(4) . ?
C1 N1 1.459(4) . ?
C2 C3 1.376(4) . ?
C2 H2 0.97(3) . ?
C3 C4 1.399(5) . ?
C3 H3 0.92(4) . ?
C4 C5 1.386(4) . ?
C4 N2 1.401(4) . ?
C5 C6 1.376(4) . ?
C5 H5 0.97(3) . ?
C6 H6 0.93(3) . ?
C7 C8 1.389(4) . ?
C7 N2 1.389(4) . ?
C7 C12 1.408(4) . ?
C8 C9 1.382(5) . ?
C8 H8 0.98(3) . ?
C9 C10 1.376(5) . ?
C9 H9 0.93(3) . ?
C10 C11 1.382(5) . ?
C10 H10 0.98(4) . ?
C11 C12 1.376(5) . ?
C11 H11 1.02(3) . ?
C12 H12 1.02(4) . ?
C13 C14 1.380(4) . ?
C13 C18 1.394(4) . ?
C13 N3 1.457(4) . ?
C14 C15 1.383(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.395(4) . ?
C15 H15 1.00(3) . ?
C16 C17 1.390(4) . ?
C16 N4 1.404(4) . ?
C17 C18 1.381(4) . ?
C17 H17 1.01(3) . ?
C18 H18 1.01(3) . ?
C19 C20 1.387(4) . ?
C19 N4 1.395(4) . ?
C19 C24 1.399(4) . ?
C20 C21 1.384(5) . ?
C20 H20 0.98(3) . ?
C21 C22 1.385(5) . ?
C21 H21 1.03(3) . ?
C22 C23 1.381(5) . ?
C22 H22 0.96(3) . ?
C23 C24 1.382(4) . ?
C23 H23 0.99(3) . ?
C24 H24 1.01(3) . ?
C25 O1 1.241(3) . ?
C25 O2 1.279(4) . ?
C25 C26 1.508(4) . ?
C26 O5 1.421(4) . ?
C26 H26B 1.05(3) . ?
C26 H26A 1.01(4) . ?
C27 O5 1.402(4) . ?
C27 C28 1.507(4) . ?
C27 H27B 1.01(4) . ?
C27 H27A 0.99(3) . ?
C28 O4 1.218(3) . ?
C28 O3 1.302(4) . ?
C29 O9 1.225(3) . ?
C29 O8 1.310(4) . ?
C29 C30 1.491(4) . ?
C30 O10 1.410(4) . ?
C30 H30B 1.02(3) . ?
C30 H30A 0.93(4) . ?
C31 O10 1.407(4) . ?
C31 C32 1.516(4) . ?
C31 H31A 0.98(3) . ?
C31 H31B 1.02(3) . ?
C32 O6 1.240(3) . ?
C32 O7 1.274(4) . ?
N1 H1X 0.81(4) . ?
N1 H1Z 0.93(4) . ?
N1 H1Y 1.09(5) . ?
N2 H2W 0.90(3) . ?
N3 H3Y 0.84(4) . ?
N3 H3Z 0.89(4) . ?
N3 H3X 1.05(4) . ?
N4 H4W 0.84(4) . ?
O3 H3W 0.95(4) . ?
O8 H8W 0.97(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
C6 C1 C2 120.7(3) . . ?
C6 C1 N1 119.4(3) . . ?
C2 C1 N1 119.9(3) . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 124(2) . . ?
C1 C2 H2 117(2) . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 121(2) . . ?
C4 C3 H3 117(2) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 N2 122.6(3) . . ?
C3 C4 N2 119.5(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 121.4(18) . . ?
C4 C5 H5 117.7(18) . . ?
C1 C6 C5 120.1(3) . . ?
C1 C6 H6 120.8(18) . . ?
C5 C6 H6 119.0(18) . . ?
C8 C7 N2 124.9(3) . . ?
C8 C7 C12 118.1(3) . . ?
N2 C7 C12 116.9(3) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 116.6(19) . . ?
C7 C8 H8 123.0(19) . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 121(2) . . ?
C8 C9 H9 118(2) . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 123(2) . . ?
C11 C10 H10 117(2) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 118.4(18) . . ?
C10 C11 H11 121.5(18) . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H12 121.2(19) . . ?
C7 C12 H12 117.9(19) . . ?
C14 C13 C18 120.5(3) . . ?
C14 C13 N3 121.2(2) . . ?
C18 C13 N3 118.3(3) . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 119.2(19) . . ?
C16 C15 H15 120.6(19) . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 N4 118.5(3) . . ?
C15 C16 N4 122.2(3) . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 120.2(17) . . ?
C16 C17 H17 118.4(17) . . ?
C17 C18 C13 118.9(3) . . ?
C17 C18 H18 118.8(19) . . ?
C13 C18 H18 122.3(19) . . ?
C20 C19 N4 117.7(3) . . ?
C20 C19 C24 118.7(3) . . ?
N4 C19 C24 123.5(3) . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.3(16) . . ?
C19 C20 H20 119.9(16) . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 121.1(19) . . ?
C22 C21 H21 118.5(19) . . ?
C23 C22 C21 119.1(3) . . ?
C23 C22 H22 120(2) . . ?
C21 C22 H22 121(2) . . ?
C22 C23 C24 121.1(3) . . ?
C22 C23 H23 120.1(18) . . ?
C24 C23 H23 118.7(18) . . ?
C23 C24 C19 120.0(3) . . ?
C23 C24 H24 116.0(18) . . ?
C19 C24 H24 123.8(18) . . ?
O1 C25 O2 124.0(3) . . ?
O1 C25 C26 121.4(3) . . ?
O2 C25 C26 114.6(3) . . ?
O5 C26 C25 110.3(2) . . ?
O5 C26 H26B 108.3(19) . . ?
C25 C26 H26B 110.8(18) . . ?
O5 C26 H26A 110(2) . . ?
C25 C26 H26A 108(2) . . ?
H26B C26 H26A 109(3) . . ?
O5 C27 C28 109.7(2) . . ?
O5 C27 H27B 112(2) . . ?
C28 C27 H27B 106(2) . . ?
O5 C27 H27A 111.9(19) . . ?
C28 C27 H27A 106(2) . . ?
H27B C27 H27A 111(3) . . ?
O4 C28 O3 124.4(3) . . ?
O4 C28 C27 123.5(3) . . ?
O3 C28 C27 112.1(2) . . ?
O9 C29 O8 124.0(3) . . ?
O9 C29 C30 123.5(3) . . ?
O8 C29 C30 112.6(2) . . ?
O10 C30 C29 109.3(2) . . ?
O10 C30 H30B 112.1(19) . . ?
C29 C30 H30B 107.9(19) . . ?
O10 C30 H30A 110(2) . . ?
C29 C30 H30A 106(2) . . ?
H30B C30 H30A 111(3) . . ?
O10 C31 C32 111.3(2) . . ?
O10 C31 H31A 111.3(17) . . ?
C32 C31 H31A 106.6(16) . . ?
O10 C31 H31B 115.5(18) . . ?
C32 C31 H31B 107.8(18) . . ?
H31A C31 H31B 104(2) . . ?
O6 C32 O7 124.6(3) . . ?
O6 C32 C31 121.8(3) . . ?
O7 C32 C31 113.5(2) . . ?
C1 N1 H1X 110(2) . . ?
C1 N1 H1Z 113(2) . . ?
H1X N1 H1Z 103(3) . . ?
C1 N1 H1Y 110(2) . . ?
H1X N1 H1Y 111(3) . . ?
H1Z N1 H1Y 109(3) . . ?
C7 N2 C4 129.1(3) . . ?
C7 N2 H2W 111(2) . . ?
C4 N2 H2W 120(2) . . ?
C13 N3 H3Y 109(2) . . ?
C13 N3 H3Z 112(2) . . ?
H3Y N3 H3Z 109(4) . . ?
C13 N3 H3X 108(2) . . ?
H3Y N3 H3X 110(3) . . ?
H3Z N3 H3X 109(3) . . ?
C19 N4 C16 128.7(3) . . ?
C19 N4 H4W 119(2) . . ?
C16 N4 H4W 110(2) . . ?
C28 O3 H3W 118(2) . . ?
C27 O5 C26 112.3(2) . . ?
C29 O8 H8W 111(3) . . ?
C31 O10 C30 111.7(2) . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.095

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_N-Phenyl-p-phenylenediamine+diglycolicacid
_database_code_depnum_ccdc_archive 'CCDC 1435837'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'N-Phenyl-p-phenylenediamine+diglycolic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H12 N2), 2(C4 H6 O5)'
_chemical_formula_sum            'C32 H36 N4 O10'
_chemical_formula_weight         636.65

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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.9195(15)
_cell_length_b                   9.1323(8)
_cell_length_c                   18.7653(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3070.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9879
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      26.26

_exptl_crystal_description       Plate
_exptl_crystal_colour            Bluish-black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7265
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   INCOATECImuSMo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41535
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_full        25.242
_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 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             5837
_reflns_number_gt                5545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_max     0.851
_reflns_Friedel_fraction_full    0.901

_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-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0349P)²+0.5084P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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_abs_structure_details 
; 
 Flack x determined using 2341 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.25(19)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5837
_refine_ls_number_parameters     523
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0651
_refine_ls_wR_factor_gt          0.0635
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.053
_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
C1 C 0.12357(11) 0.6052(2) 0.34063(10) 0.0163(4) Uani 1 1 d . . . . .
C2 C 0.06875(13) 0.6455(2) 0.29312(12) 0.0269(5) Uani 1 1 d . . . . .
C3 C 0.05583(14) 0.5599(3) 0.23352(13) 0.0300(5) Uani 1 1 d . . . . .
C4 C 0.09793(12) 0.4363(2) 0.22007(11) 0.0224(4) Uani 1 1 d . . . . .
C5 C 0.15375(13) 0.3995(2) 0.26803(13) 0.0285(5) Uani 1 1 d . . . . .
C6 C 0.16656(13) 0.4829(2) 0.32862(13) 0.0269(5) Uani 1 1 d . . . . .
H6A H 0.2037 0.4564 0.3607 0.032 Uiso 1 1 calc R U . . .
C7 C 0.05001(12) 0.2139(2) 0.16066(12) 0.0222(4) Uani 1 1 d . . . . .
C8 C 0.04801(13) 0.1286(2) 0.09873(12) 0.0258(5) Uani 1 1 d . . . . .
C9 C 0.01368(14) -0.0065(2) 0.09916(13) 0.0285(5) Uani 1 1 d . . . . .
C10 C -0.01862(14) -0.0613(2) 0.16068(13) 0.0290(5) Uani 1 1 d . . . . .
C11 C -0.01769(13) 0.0238(2) 0.22158(13) 0.0273(5) Uani 1 1 d . . . . .
C12 C 0.01617(13) 0.1607(2) 0.22192(12) 0.0236(5) Uani 1 1 d . . . . .
C13 C 0.37804(11) 0.3947(2) 0.34614(10) 0.0191(4) Uani 1 1 d . . . . .
C14 C 0.37720(12) 0.5458(2) 0.34987(12) 0.0220(4) Uani 1 1 d . . . . .
C15 C 0.36319(13) 0.6279(2) 0.28968(11) 0.0230(5) Uani 1 1 d . . . . .
C16 C 0.34938(11) 0.5607(2) 0.22448(11) 0.0214(4) Uani 1 1 d . . . . .
C17 C 0.35031(12) 0.4074(2) 0.22153(12) 0.0228(4) Uani 1 1 d . . . . .
C18 C 0.36470(12) 0.3246(2) 0.28180(11) 0.0213(4) Uani 1 1 d . . . . .
C19 C 0.30541(12) 0.7818(2) 0.15875(11) 0.0232(4) Uani 1 1 d . . . . .
C20 C 0.32647(14) 0.8726(3) 0.10248(13) 0.0296(5) Uani 1 1 d . . . . .
C21 C 0.29200(14) 1.0073(3) 0.09406(15) 0.0368(6) Uani 1 1 d . . . . .
H21A H 0.3060 1.0674 0.0564 0.044 Uiso 1 1 calc R U . . .
C22 C 0.23762(15) 1.0536(3) 0.14033(15) 0.0377(6) Uani 1 1 d . . . . .
H22A H 0.2154 1.1449 0.1344 0.045 Uiso 1 1 calc R U . . .
C23 C 0.21613(15) 0.9633(3) 0.19583(15) 0.0379(6) Uani 1 1 d . . . . .
C24 C 0.24996(14) 0.8279(3) 0.20521(13) 0.0305(5) Uani 1 1 d . . . . .
C25 C 0.25356(11) 0.4637(2) 0.01634(10) 0.0169(4) Uani 1 1 d . . . . .
C26 C 0.19671(10) 0.5770(2) 0.03959(11) 0.0176(4) Uani 1 1 d . . . . .
H26A H 0.2030 0.5983 0.0899 0.021 Uiso 1 1 calc R U . . .
H26B H 0.2042 0.6671 0.0131 0.021 Uiso 1 1 calc R U . . .
C27 C 0.06799(10) 0.6313(2) 0.03689(11) 0.0174(4) Uani 1 1 d . . . . .
H27A H 0.0783 0.7150 0.0067 0.021 Uiso 1 1 calc R U . . .
H27B H 0.0678 0.6639 0.0861 0.021 Uiso 1 1 calc R U . . .
C28 C -0.00690(11) 0.5657(2) 0.01779(10) 0.0173(4) Uani 1 1 d . . . . .
C29 C 0.78941(10) 1.0483(2) 0.39734(11) 0.0166(4) Uani 1 1 d . . . . .
C30 C 0.72895(10) 0.9353(2) 0.39006(13) 0.0220(4) Uani 1 1 d . . . . .
H30A H 0.7330 0.8880 0.3439 0.026 Uiso 1 1 calc R U . . .
H30B H 0.7351 0.8610 0.4265 0.026 Uiso 1 1 calc R U . . .
C31 C 0.60122(10) 0.8930(2) 0.40236(14) 0.0220(4) Uani 1 1 d . . . . .
C32 C 0.52563(10) 0.9648(2) 0.40502(11) 0.0154(4) Uani 1 1 d . . . . .
N1 N 0.13616(9) 0.69366(18) 0.40446(10) 0.0169(3) Uani 1 1 d . . . . .
N2 N 0.08543(12) 0.3497(2) 0.15869(11) 0.0317(5) Uani 1 1 d . . . . .
N3 N 0.39257(10) 0.31127(19) 0.41136(10) 0.0201(3) Uani 1 1 d . . . . .
N4 N 0.33790(11) 0.6415(2) 0.16295(10) 0.0263(4) Uani 1 1 d . . . . .
O1 O 0.23354(8) 0.34431(15) -0.00742(9) 0.0269(3) Uani 1 1 d . . . . .
O2 O 0.32117(7) 0.50518(15) 0.02352(8) 0.0206(3) Uani 1 1 d . . . . .
O3 O -0.01369(8) 0.45224(16) -0.01527(8) 0.0229(3) Uani 1 1 d . . . . .
O4 O -0.06237(8) 0.64638(15) 0.04009(8) 0.0237(3) Uani 1 1 d . . . . .
O5 O 0.12330(7) 0.52248(13) 0.02700(7) 0.0159(3) Uani 1 1 d . . . . .
O6 O 0.85512(7) 0.99275(14) 0.39207(9) 0.0245(3) Uani 1 1 d . . . . .
O7 O 0.77579(7) 1.17854(14) 0.40725(8) 0.0212(3) Uani 1 1 d . . . . .
O8 O 0.51769(7) 1.09803(14) 0.40671(8) 0.0192(3) Uani 1 1 d . . . . .
O9 O 0.47179(7) 0.87043(14) 0.40501(8) 0.0199(3) Uani 1 1 d D . . . .
O10 O 0.65745(7) 1.00044(13) 0.39683(9) 0.0204(3) Uani 1 1 d . . . . .
H14 H 0.3866(11) 0.593(2) 0.3937(12) 0.014(5) Uiso 1 1 d . . . . .
H12 H 0.0164(12) 0.221(3) 0.2634(13) 0.019(6) Uiso 1 1 d . . . . .
H31B H 0.6009(14) 0.829(3) 0.3610(14) 0.030(6) Uiso 1 1 d . . . . .
H4P H 0.3426(13) 0.595(3) 0.1237(13) 0.018(6) Uiso 1 1 d . . . . .
H3Y H 0.3957(14) 0.217(3) 0.4022(15) 0.038(7) Uiso 1 1 d . . . . .
H3X H 0.3521(17) 0.322(3) 0.4412(15) 0.038(7) Uiso 1 1 d . . . . .
H24 H 0.2331(14) 0.765(3) 0.2437(15) 0.031(6) Uiso 1 1 d . . . . .
H11 H -0.0402(13) -0.009(3) 0.2651(13) 0.025(6) Uiso 1 1 d . . . . .
H31A H 0.6081(15) 0.835(3) 0.4450(14) 0.034(7) Uiso 1 1 d . . . . .
H1Y H 0.1023(13) 0.764(3) 0.4078(14) 0.026(6) Uiso 1 1 d . . . . .
H10 H -0.0424(13) -0.157(3) 0.1607(13) 0.027(6) Uiso 1 1 d . . . . .
H1X H 0.1317(14) 0.639(3) 0.4441(14) 0.029(7) Uiso 1 1 d . . . . .
H5 H 0.1871(15) 0.318(3) 0.2583(14) 0.036(7) Uiso 1 1 d . . . . .
H8 H 0.0721(15) 0.161(3) 0.0562(14) 0.034(7) Uiso 1 1 d . . . . .
H9 H 0.0124(14) -0.058(3) 0.0552(14) 0.030(6) Uiso 1 1 d . . . . .
H2 H 0.0401(15) 0.734(3) 0.3006(14) 0.038(7) Uiso 1 1 d . . . . .
H17 H 0.3413(12) 0.363(3) 0.1753(13) 0.021(6) Uiso 1 1 d . . . . .
H15 H 0.3617(14) 0.727(3) 0.2931(14) 0.034(7) Uiso 1 1 d . . . . .
H18 H 0.3637(13) 0.217(3) 0.2791(12) 0.026(6) Uiso 1 1 d . . . . .
H1Z H 0.1834(13) 0.742(2) 0.4053(13) 0.027(6) Uiso 1 1 d . . . . .
H3 H 0.0206(16) 0.586(3) 0.2001(15) 0.043(8) Uiso 1 1 d . . . . .
H23 H 0.1743(19) 0.991(3) 0.2264(18) 0.064(10) Uiso 1 1 d . . . . .
H3Z H 0.4345(15) 0.346(3) 0.4332(13) 0.026(6) Uiso 1 1 d . . . . .
H20 H 0.3642(15) 0.842(2) 0.0694(13) 0.029(6) Uiso 1 1 d . . . . .
H4W H -0.108(2) 0.598(4) 0.0277(18) 0.062(9) Uiso 1 1 d . . . . .
H2P H 0.0952(15) 0.390(3) 0.1195(14) 0.030(7) Uiso 1 1 d . . . . .
H9W H 0.4281(15) 0.915(4) 0.402(2) 0.094(12) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.376(3) . ?
C1 C2 1.377(3) . ?
C1 N1 1.462(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.97(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.92(3) . ?
C4 C5 1.387(3) . ?
C4 N2 1.415(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.97(3) . ?
C6 H6A 0.9300 . ?
C7 C12 1.387(3) . ?
C7 N2 1.393(3) . ?
C7 C8 1.399(3) . ?
C8 C9 1.379(3) . ?
C8 H8 0.95(3) . ?
C9 C10 1.385(4) . ?
C9 H9 0.95(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.98(3) . ?
C11 C12 1.390(3) . ?
C11 H11 0.96(2) . ?
C12 H12 0.95(2) . ?
C13 C14 1.382(3) . ?
C13 C18 1.387(3) . ?
C13 N3 1.465(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.94(2) . ?
C15 C16 1.391(3) . ?
C15 H15 0.90(3) . ?
C16 N4 1.386(3) . ?
C16 C17 1.401(3) . ?
C17 C18 1.385(3) . ?
C17 H17 0.97(2) . ?
C18 H18 0.98(2) . ?
C19 C24 1.387(3) . ?
C19 C20 1.394(3) . ?
C19 N4 1.410(3) . ?
C20 C21 1.386(3) . ?
C20 H20 0.96(3) . ?
C21 C22 1.372(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.383(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.389(3) . ?
C23 H23 0.98(3) . ?
C24 H24 0.97(3) . ?
C25 O1 1.231(2) . ?
C25 O2 1.276(2) . ?
C25 C26 1.516(3) . ?
C26 O5 1.426(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 O5 1.416(2) . ?
C27 C28 1.513(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 O3 1.214(2) . ?
C28 O4 1.306(2) . ?
C29 O7 1.228(2) . ?
C29 O6 1.286(2) . ?
C29 C30 1.503(3) . ?
C30 O10 1.418(2) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 O10 1.410(2) . ?
C31 C32 1.506(3) . ?
C31 H31B 0.97(3) . ?
C31 H31A 0.97(3) . ?
C32 O8 1.225(2) . ?
C32 O9 1.294(2) . ?
N1 H1Y 0.88(3) . ?
N1 H1X 0.90(3) . ?
N1 H1Z 0.96(2) . ?
N2 H2P 0.84(3) . ?
N3 H3Y 0.88(3) . ?
N3 H3X 0.92(3) . ?
N3 H3Z 0.91(3) . ?
N4 H4P 0.86(2) . ?
O4 H4W 0.96(4) . ?
O9 H9W 0.88(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
C6 C1 C2 120.68(19) . . ?
C6 C1 N1 119.76(18) . . ?
C2 C1 N1 119.55(17) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.5(16) . . ?
C3 C2 H2 120.0(16) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 117.5(18) . . ?
C2 C3 H3 121.2(18) . . ?
C3 C4 C5 118.3(2) . . ?
C3 C4 N2 121.3(2) . . ?
C5 C4 N2 120.5(2) . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 120.5(16) . . ?
C6 C5 H5 118.1(16) . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
C12 C7 N2 122.2(2) . . ?
C12 C7 C8 118.83(19) . . ?
N2 C7 C8 119.0(2) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.0(15) . . ?
C7 C8 H8 120.7(15) . . ?
C8 C9 C10 121.0(2) . . ?
C8 C9 H9 116.7(15) . . ?
C10 C9 H9 122.3(15) . . ?
C11 C10 C9 118.7(2) . . ?
C11 C10 H10 120.7(15) . . ?
C9 C10 H10 120.5(15) . . ?
C10 C11 C12 121.0(2) . . ?
C10 C11 H11 121.3(14) . . ?
C12 C11 H11 117.7(14) . . ?
C7 C12 C11 120.1(2) . . ?
C7 C12 H12 118.3(14) . . ?
C11 C12 H12 121.6(14) . . ?
C14 C13 C18 120.19(19) . . ?
C14 C13 N3 118.63(18) . . ?
C18 C13 N3 121.18(18) . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.8(13) . . ?
C13 C14 H14 119.9(13) . . ?
C14 C15 C16 120.86(19) . . ?
C14 C15 H15 119.3(17) . . ?
C16 C15 H15 119.8(17) . . ?
N4 C16 C15 121.60(19) . . ?
N4 C16 C17 120.08(19) . . ?
C15 C16 C17 118.27(19) . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 122.2(14) . . ?
C16 C17 H17 116.7(14) . . ?
C17 C18 C13 119.42(19) . . ?
C17 C18 H18 120.0(14) . . ?
C13 C18 H18 120.6(14) . . ?
C24 C19 C20 119.3(2) . . ?
C24 C19 N4 122.4(2) . . ?
C20 C19 N4 118.1(2) . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 H20 119.8(14) . . ?
C19 C20 H20 120.6(14) . . ?
C22 C21 C20 121.2(2) . . ?
C22 C21 H21A 119.4 . . ?
C20 C21 H21A 119.4 . . ?
C21 C22 C23 119.4(2) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 H22A 120.3 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 120.3(19) . . ?
C24 C23 H23 119.2(19) . . ?
C19 C24 C23 120.2(2) . . ?
C19 C24 H24 120.6(15) . . ?
C23 C24 H24 119.1(15) . . ?
O1 C25 O2 125.27(18) . . ?
O1 C25 C26 120.85(17) . . ?
O2 C25 C26 113.88(16) . . ?
O5 C26 C25 109.48(15) . . ?
O5 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
O5 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
O5 C27 C28 108.19(15) . . ?
O5 C27 H27A 110.1 . . ?
C28 C27 H27A 110.1 . . ?
O5 C27 H27B 110.1 . . ?
C28 C27 H27B 110.1 . . ?
H27A C27 H27B 108.4 . . ?
O3 C28 O4 124.68(18) . . ?
O3 C28 C27 123.23(17) . . ?
O4 C28 C27 112.09(17) . . ?
O7 C29 O6 125.15(17) . . ?
O7 C29 C30 122.40(16) . . ?
O6 C29 C30 112.45(16) . . ?
O10 C30 C29 110.77(15) . . ?
O10 C30 H30A 109.5 . . ?
C29 C30 H30A 109.5 . . ?
O10 C30 H30B 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
O10 C31 C32 110.03(15) . . ?
O10 C31 H31B 111.4(15) . . ?
C32 C31 H31B 106.5(15) . . ?
O10 C31 H31A 110.6(16) . . ?
C32 C31 H31A 109.1(16) . . ?
H31B C31 H31A 109.2(19) . . ?
O8 C32 O9 125.10(17) . . ?
O8 C32 C31 122.52(16) . . ?
O9 C32 C31 112.39(16) . . ?
C1 N1 H1Y 110.6(16) . . ?
C1 N1 H1X 111.0(16) . . ?
H1Y N1 H1X 106(2) . . ?
C1 N1 H1Z 113.9(15) . . ?
H1Y N1 H1Z 106(2) . . ?
H1X N1 H1Z 109(2) . . ?
C7 N2 C4 123.23(19) . . ?
C7 N2 H2P 120.5(18) . . ?
C4 N2 H2P 115.8(17) . . ?
C13 N3 H3Y 111.0(19) . . ?
C13 N3 H3X 108.1(17) . . ?
H3Y N3 H3X 106(2) . . ?
C13 N3 H3Z 109.9(15) . . ?
H3Y N3 H3Z 112(2) . . ?
H3X N3 H3Z 110(2) . . ?
C16 N4 C19 126.31(19) . . ?
C16 N4 H4P 115.8(15) . . ?
C19 N4 H4P 116.6(15) . . ?
C28 O4 H4W 108.2(19) . . ?
C27 O5 C26 112.25(13) . . ?
C32 O9 H9W 111(3) . . ?
C31 O10 C30 111.10(14) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_p-Phenylenediamine+lawsone
_database_code_depnum_ccdc_archive 'CCDC 1435838'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        1,4-Diaminobenzene+lawsone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H5 O3), C6 H10 N2'
_chemical_formula_sum            'C26 H20 N2 O6'
_chemical_formula_weight         456.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.204(3)
_cell_length_b                   8.573(2)
_cell_length_c                   8.3934(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.851(13)
_cell_angle_gamma                90
_cell_volume                     1021.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4963
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      28.60

_exptl_crystal_description       Block
_exptl_crystal_colour            'orangeish brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5369
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   INCOATECImuSMo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4626
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         25.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             985
_reflns_number_gt                737
_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-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0726P)²+10.3813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         985
_refine_ls_number_parameters     90
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0982
_refine_ls_wR_factor_ref         0.2574
_refine_ls_wR_factor_gt          0.2413
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.005
_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
C1 C 0.1892(3) 0.0807(6) 0.2372(6) 0.0288(12) Uani 1 1 d . . . . .
H1 H 0.2084 0.1355 0.1453 0.035 Uiso 0.5 1 calc R U P A 1
C2 C 0.1600(3) 0.1685(6) 0.3777(6) 0.0301(12) Uani 1 1 d . . . . .
C3 C 0.1288(3) 0.0815(6) 0.5210(6) 0.0276(12) Uani 1 1 d . . . . .
C4 C 0.1004(3) 0.1624(7) 0.6541(6) 0.0343(13) Uani 1 1 d . . . . .
H4 H 0.0995 0.2732 0.6535 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0731(4) 0.0813(7) 0.7886(6) 0.0388(14) Uani 1 1 d . . . . .
H5 H 0.0545 0.1367 0.8804 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4092(4) 0.0000 0.9437(8) 0.0236(16) Uani 1 2 d S T P . .
C7 C 0.4280(5) 0.0000 1.1057(8) 0.0241(16) Uani 1 2 d S T P . .
H7 H 0.3775 0.0000 1.1773 0.029 Uiso 1 2 calc R U P . .
C8 C 0.5182(5) 0.0000 1.1632(9) 0.0299(17) Uani 1 2 d S T P . .
H8 H 0.5316 0.0000 1.2749 0.036 Uiso 1 2 calc R U P . .
N1 N 0.3116(4) 0.0000 0.8843(7) 0.0295(15) Uani 1 2 d S T P . .
H1A H 0.2923 -0.0999 0.8669 0.035 Uiso 0.5 1 calc R U P B -1
H1B H 0.3071 0.0544 0.7912 0.035 Uiso 0.5 1 calc R U P B -1
H1C H 0.2746 0.0455 0.9575 0.035 Uiso 0.5 1 calc R U P B -1
O1 O 0.1612(3) 0.3117(4) 0.3806(4) 0.0367(11) Uani 1 1 d . . . . .
O2 O 0.2139(5) 0.1641(8) 0.1164(8) 0.0307(17) Uani 0.5 1 d . . P C 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.298(8) . ?
C1 C1 1.384(11) 6 ?
C1 C2 1.469(7) . ?
C1 H1 0.9500 . ?
C2 O1 1.229(6) . ?
C2 C3 1.495(7) . ?
C3 C4 1.386(7) . ?
C3 C3 1.397(11) 6 ?
C4 C5 1.391(7) . ?
C4 H4 0.9500 . ?
C5 C5 1.394(12) 6 ?
C5 H5 0.9500 . ?
C6 C7 1.377(10) . ?
C6 C8 1.388(9) 5_657 ?
C6 N1 1.458(9) . ?
C7 C8 1.355(10) . ?
C7 H7 0.9500 . ?
C8 C6 1.388(9) 5_657 ?
C8 H8 0.9500 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?

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 C1 C1 123.4(4) . 6 ?
O2 C1 C2 115.8(5) . . ?
C1 C1 C2 120.8(3) 6 . ?
C1 C1 H1 119.6 6 . ?
C2 C1 H1 119.6 . . ?
O1 C2 C1 121.6(5) . . ?
O1 C2 C3 119.1(5) . . ?
C1 C2 C3 119.3(4) . . ?
C4 C3 C3 120.0(3) . 6 ?
C4 C3 C2 120.1(5) . . ?
C3 C3 C2 119.9(3) 6 . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C5 120.0(3) . 6 ?
C4 C5 H5 120.0 . . ?
C5 C5 H5 120.0 6 . ?
C7 C6 C8 120.9(6) . 5_657 ?
C7 C6 N1 119.3(6) . . ?
C8 C6 N1 119.7(6) 5_657 . ?
C8 C7 C6 120.2(6) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C6 118.9(7) . 5_657 ?
C7 C8 H8 120.6 . . ?
C6 C8 H8 120.6 5_657 . ?
C6 N1 H1A 109.5 . . ?
C6 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C6 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_p-Phenylenediamine+sebacic
_database_code_depnum_ccdc_archive 'CCDC 1435839'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,4-Diaminobenzene+sebacic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 O4, 2(C6 H9 N2)'
_chemical_formula_sum            'C22 H34 N4 O4'
_chemical_formula_weight         418.53

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   9.1366(7)
_cell_length_b                   6.2639(6)
_cell_length_c                   20.6631(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.489(5)
_cell_angle_gamma                90.00
_cell_volume                     1178.94(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4709
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      27.13

_exptl_crystal_description       Block
_exptl_crystal_colour            Purplish-Black
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6113
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         INCOATECImuSMo
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8666
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         27.14
_reflns_number_total             2570
_reflns_number_gt                2257
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0442P)²+2.1065P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2570
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.1891
_refine_ls_wR_factor_gt          0.1854
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_restrained_S_all      1.213
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6465(3) 0.1243(4) 0.12982(13) 0.0241(6) Uani 1 1 d . . .
C2 C 0.5934(3) 0.1962(6) 0.06177(14) 0.0341(7) Uani 1 1 d . . .
C3 C 0.6757(3) 0.3842(6) 0.03644(13) 0.0335(7) Uani 1 1 d . . .
C4 C 0.8387(3) 0.3379(5) 0.03156(13) 0.0332(7) Uani 1 1 d . . .
C5 C 0.9187(3) 0.5218(6) 0.00226(13) 0.0336(7) Uani 1 1 d . . .
C6 C 0.2841(3) 0.6113(4) 0.16362(12) 0.0249(6) Uani 1 1 d . . .
C7 C 0.1998(3) 0.7920(5) 0.14759(13) 0.0264(6) Uani 1 1 d . . .
C8 C 0.0530(3) 0.7995(4) 0.15911(12) 0.0242(6) Uani 1 1 d . . .
C9 C -0.0120(3) 0.6257(4) 0.18687(11) 0.0211(5) Uani 1 1 d . . .
C10 C 0.0693(3) 0.4445(4) 0.20256(12) 0.0237(5) Uani 1 1 d . . .
C11 C 0.2158(3) 0.4361(4) 0.19120(12) 0.0253(6) Uani 1 1 d . . .
N1 N 0.4305(3) 0.6022(5) 0.15227(16) 0.0418(7) Uani 1 1 d . . .
N2 N -0.1666(2) 0.6345(4) 0.20063(11) 0.0220(5) Uani 1 1 d . . .
O1 O 0.6563(3) -0.0702(4) 0.14069(13) 0.0469(6) Uani 1 1 d . . .
O2 O 0.6735(2) 0.2646(3) 0.17331(9) 0.0291(5) Uani 1 1 d . . .
H8 H 0.001(3) 0.923(5) 0.1474(13) 0.016(7) Uiso 1 1 d . . .
H11 H 0.274(3) 0.311(5) 0.2029(13) 0.016(7) Uiso 1 1 d . . .
H1X H 0.479(4) 0.705(6) 0.1429(16) 0.030(9) Uiso 1 1 d . . .
H2Y H -0.215(3) 0.505(6) 0.1890(14) 0.025(8) Uiso 1 1 d . . .
H2X H -0.212(4) 0.745(6) 0.1787(17) 0.037(9) Uiso 1 1 d . . .
H4B H 0.853(3) 0.204(5) 0.0059(14) 0.023(7) Uiso 1 1 d . . .
H1Y H 0.483(4) 0.492(7) 0.1637(17) 0.039(10) Uiso 1 1 d . . .
H7 H 0.238(3) 0.916(5) 0.1318(15) 0.027(8) Uiso 1 1 d . . .
H3B H 0.668(3) 0.507(6) 0.0658(16) 0.031(8) Uiso 1 1 d . . .
H3A H 0.628(4) 0.436(6) -0.0107(18) 0.053(11) Uiso 1 1 d . . .
H5B H 0.909(4) 0.651(6) 0.0282(17) 0.040(9) Uiso 1 1 d . . .
H5A H 0.877(4) 0.556(6) -0.0428(17) 0.037(9) Uiso 1 1 d . . .
H2B H 0.485(4) 0.236(6) 0.0633(16) 0.039(9) Uiso 1 1 d . . .
H2A H 0.608(4) 0.076(6) 0.0319(17) 0.039(9) Uiso 1 1 d . . .
H4A H 0.885(3) 0.295(5) 0.0754(16) 0.030(8) Uiso 1 1 d . . .
H10 H 0.019(4) 0.322(6) 0.2201(16) 0.039(9) Uiso 1 1 d . . .
H2Z H -0.172(4) 0.658(6) 0.2446(18) 0.040(9) 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
C1 O1 1.241(3) . ?
C1 O2 1.268(3) . ?
C1 C2 1.519(4) . ?
C2 C3 1.513(4) . ?
C2 H2B 1.03(3) . ?
C2 H2A 0.99(4) . ?
C3 C4 1.528(4) . ?
C3 H3B 0.98(3) . ?
C3 H3A 1.09(4) . ?
C4 C5 1.516(4) . ?
C4 H4B 1.01(3) . ?
C4 H4A 1.00(3) . ?
C5 C5 1.520(6) 3_765 ?
C5 H5B 0.98(4) . ?
C5 H5A 1.00(3) . ?
C6 N1 1.377(4) . ?
C6 C7 1.395(4) . ?
C6 C11 1.405(4) . ?
C7 C8 1.382(4) . ?
C7 H7 0.92(3) . ?
C8 C9 1.386(4) . ?
C8 H8 0.93(3) . ?
C9 C10 1.381(4) . ?
C9 N2 1.463(3) . ?
C10 C11 1.378(4) . ?
C10 H10 0.98(4) . ?
C11 H11 0.97(3) . ?
N1 H1X 0.82(4) . ?
N1 H1Y 0.86(4) . ?
N2 H2Y 0.95(3) . ?
N2 H2X 0.91(4) . ?
N2 H2Z 0.92(4) . ?

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
O1 C1 O2 123.1(3) . . ?
O1 C1 C2 118.1(3) . . ?
O2 C1 C2 118.7(2) . . ?
C3 C2 C1 114.8(2) . . ?
C3 C2 H2B 109(2) . . ?
C1 C2 H2B 106.5(19) . . ?
C3 C2 H2A 106(2) . . ?
C1 C2 H2A 108(2) . . ?
H2B C2 H2A 112(3) . . ?
C2 C3 C4 112.9(3) . . ?
C2 C3 H3B 109.6(19) . . ?
C4 C3 H3B 107.6(19) . . ?
C2 C3 H3A 112(2) . . ?
C4 C3 H3A 109(2) . . ?
H3B C3 H3A 106(3) . . ?
C5 C4 C3 112.7(3) . . ?
C5 C4 H4B 109.6(17) . . ?
C3 C4 H4B 111.3(17) . . ?
C5 C4 H4A 112.6(19) . . ?
C3 C4 H4A 109.4(18) . . ?
H4B C4 H4A 101(2) . . ?
C4 C5 C5 113.1(4) . 3_765 ?
C4 C5 H5B 110(2) . . ?
C5 C5 H5B 109(2) 3_765 . ?
C4 C5 H5A 112(2) . . ?
C5 C5 H5A 106.4(19) 3_765 . ?
H5B C5 H5A 107(3) . . ?
N1 C6 C7 121.3(3) . . ?
N1 C6 C11 120.3(3) . . ?
C7 C6 C11 118.4(2) . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 115.8(19) . . ?
C6 C7 H7 123.2(19) . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 117.7(17) . . ?
C9 C8 H8 122.4(17) . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 N2 119.6(2) . . ?
C8 C9 N2 120.2(2) . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 121(2) . . ?
C9 C10 H10 118(2) . . ?
C10 C11 C6 120.5(3) . . ?
C10 C11 H11 120.7(16) . . ?
C6 C11 H11 118.7(17) . . ?
C6 N1 H1X 124(2) . . ?
C6 N1 H1Y 121(2) . . ?
H1X N1 H1Y 113(3) . . ?
C9 N2 H2Y 110.7(18) . . ?
C9 N2 H2X 110(2) . . ?
H2Y N2 H2X 110(3) . . ?
C9 N2 H2Z 109(2) . . ?
H2Y N2 H2Z 109(3) . . ?
H2X N2 H2Z 108(3) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.14
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_p-Phenylenediamine+trimesic
_database_code_depnum_ccdc_archive 'CCDC 1435840'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        '1,4-Diaminobenzene+trimesic acid+methanol'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H5 O6, C6 H9 N2, C H4 O'
_chemical_formula_sum            'C16 H18 N2 O7'
_chemical_formula_weight         350.32

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   3.9902(2)
_cell_length_b                   17.0520(9)
_cell_length_c                   23.5518(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1602.49(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6661
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      29.02

_exptl_crystal_description       'Rod shaped'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   INCOATECImuSMo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13202
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.474
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3235
_reflns_number_gt                3031
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.999

_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-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0391P)²+0.2990P] 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_abs_structure_details 
; 
 Flack x determined using 1143 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.2(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3235
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0742
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.0471(6) 0.15804(11) 0.43855(9) 0.0175(4) Uani 1 1 d . . . . .
C2 C 0.2312(6) 0.12859(12) 0.39286(9) 0.0187(4) Uani 1 1 d . . . . .
C3 C 0.2928(6) 0.17465(12) 0.34559(9) 0.0177(4) Uani 1 1 d . . . . .
C4 C 0.1762(5) 0.25089(11) 0.34417(8) 0.0147(4) Uani 1 1 d . . . . .
C5 C -0.0039(5) 0.28174(12) 0.38906(9) 0.0161(4) Uani 1 1 d . . . . .
C6 C -0.0691(6) 0.23558(12) 0.43596(9) 0.0181(4) Uani 1 1 d . . . . .
C7 C 0.5748(6) 0.38636(11) 0.94392(8) 0.0155(4) Uani 1 1 d . . . . .
C8 C 0.7099(5) 0.44628(11) 0.91111(8) 0.0157(4) Uani 1 1 d . . . . .
C9 C 0.6985(5) 0.44093(11) 0.85216(8) 0.0156(4) Uani 1 1 d . . . . .
C10 C 0.5446(5) 0.37696(11) 0.82640(9) 0.0144(4) Uani 1 1 d . . . . .
C11 C 0.4047(6) 0.31766(11) 0.85912(9) 0.0146(4) Uani 1 1 d . . . . .
C12 C 0.4227(5) 0.32232(11) 0.91793(8) 0.0146(4) Uani 1 1 d . . . . .
C13 C 0.6053(6) 0.39068(11) 1.00698(9) 0.0168(4) Uani 1 1 d . . . . .
C14 C 0.2363(5) 0.24957(10) 0.82987(8) 0.0136(4) Uani 1 1 d . . . . .
C15 C 0.8611(5) 0.50348(12) 0.81753(9) 0.0168(4) Uani 1 1 d . . . . .
C16 C 0.3419(6) 0.53871(13) 0.65868(10) 0.0215(5) Uani 1 1 d . . . . .
N1 N -0.0044(6) 0.11274(12) 0.48679(9) 0.0281(5) Uani 1 1 d . . . . .
N2 N 0.2397(5) 0.29997(10) 0.29427(7) 0.0163(4) Uani 1 1 d . . . . .
O1 O 0.4703(4) 0.32926(8) 1.03263(6) 0.0207(4) Uani 1 1 d . . . . .
O2 O 0.7426(5) 0.44411(9) 1.03182(6) 0.0268(4) Uani 1 1 d . . . . .
O3 O 0.8587(4) 0.48909(9) 0.76292(6) 0.0249(4) Uani 1 1 d . . . . .
O4 O 0.9836(4) 0.56206(8) 0.83855(6) 0.0253(4) Uani 1 1 d . . . . .
O5 O 0.2377(4) 0.24988(8) 0.77634(5) 0.0165(3) Uani 1 1 d . . . . .
O6 O 0.1026(4) 0.19665(8) 0.85927(6) 0.0195(3) Uani 1 1 d . . . . .
O7 O 0.1842(4) 0.58553(8) 0.70176(6) 0.0180(3) Uani 1 1 d . . . . .
H5 H -0.082(6) 0.3360(13) 0.3877(9) 0.019(6) Uiso 1 1 d . . . . .
H6 H -0.203(7) 0.2563(14) 0.4678(10) 0.030(7) Uiso 1 1 d . . . . .
H12 H 0.339(6) 0.2807(12) 0.9406(9) 0.010(5) Uiso 1 1 d . . . . .
H10 H 0.536(6) 0.3726(12) 0.7862(10) 0.012(5) Uiso 1 1 d . . . . .
H2Z H 0.056(8) 0.3000(16) 0.2695(12) 0.040(8) Uiso 1 1 d . . . . .
H2Y H 0.420(8) 0.2801(16) 0.2709(12) 0.039(8) Uiso 1 1 d . . . . .
H8 H 0.811(6) 0.4916(13) 0.9295(10) 0.019(6) Uiso 1 1 d . . . . .
H3 H 0.425(7) 0.1538(14) 0.3137(10) 0.025(6) Uiso 1 1 d . . . . .
H16Z H 0.191(7) 0.5309(15) 0.6222(12) 0.041(8) Uiso 1 1 d . . . . .
H2 H 0.316(6) 0.0734(14) 0.3942(10) 0.024(6) Uiso 1 1 d . . . . .
H7Q H 0.081(9) 0.6236(17) 0.6828(13) 0.047(9) Uiso 1 1 d . . . . .
H16Y H 0.381(7) 0.4886(16) 0.6750(11) 0.033(7) Uiso 1 1 d . . . . .
H1B H -0.181(9) 0.1245(16) 0.5059(13) 0.041(9) Uiso 1 1 d . . . . .
H2A H 0.288(8) 0.3519(17) 0.3043(12) 0.044(8) Uiso 1 1 d . . . . .
H1A H 0.032(8) 0.0621(18) 0.4821(12) 0.040(8) Uiso 1 1 d . . . . .
H16X H 0.549(8) 0.5635(16) 0.6452(11) 0.035(7) Uiso 1 1 d . . . . .
H3W H 0.975(9) 0.5321(18) 0.7417(14) 0.057(9) Uiso 1 1 d . . . . .
H1W H 0.538(9) 0.3292(17) 1.0713(14) 0.055(9) 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
C1 N1 1.389(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.402(3) . ?
C2 C3 1.384(3) . ?
C2 H2 1.00(2) . ?
C3 C4 1.381(3) . ?
C3 H3 0.98(3) . ?
C4 C5 1.382(3) . ?
C4 N2 1.465(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.98(2) . ?
C6 H6 0.99(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.391(3) . ?
C7 C13 1.492(3) . ?
C8 C9 1.392(3) . ?
C8 H8 0.97(2) . ?
C9 C10 1.391(3) . ?
C9 C15 1.491(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.95(2) . ?
C11 C12 1.389(3) . ?
C11 C14 1.508(3) . ?
C12 H12 0.95(2) . ?
C13 O2 1.213(3) . ?
C13 O1 1.324(3) . ?
C14 O6 1.256(2) . ?
C14 O5 1.261(2) . ?
C15 O4 1.217(3) . ?
C15 O3 1.309(2) . ?
C16 O7 1.436(3) . ?
C16 H16Z 1.06(3) . ?
C16 H16Y 0.95(3) . ?
C16 H16X 0.98(3) . ?
N1 H1B 0.86(3) . ?
N1 H1A 0.88(3) . ?
N2 H2Z 0.94(3) . ?
N2 H2Y 0.97(3) . ?
N2 H2A 0.94(3) . ?
O1 H1W 0.95(3) . ?
O3 H3W 1.00(3) . ?
O7 H7Q 0.89(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
N1 C1 C2 120.54(19) . . ?
N1 C1 C6 120.7(2) . . ?
C2 C1 C6 118.64(19) . . ?
C3 C2 C1 120.61(19) . . ?
C3 C2 H2 120.0(13) . . ?
C1 C2 H2 119.4(13) . . ?
C4 C3 C2 119.56(19) . . ?
C4 C3 H3 120.2(14) . . ?
C2 C3 H3 120.2(14) . . ?
C3 C4 C5 120.99(18) . . ?
C3 C4 N2 119.92(18) . . ?
C5 C4 N2 119.09(18) . . ?
C6 C5 C4 119.51(19) . . ?
C6 C5 H5 120.4(13) . . ?
C4 C5 H5 120.0(14) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 120.4(14) . . ?
C1 C6 H6 118.9(14) . . ?
C8 C7 C12 120.11(18) . . ?
C8 C7 C13 119.04(18) . . ?
C12 C7 C13 120.82(18) . . ?
C7 C8 C9 119.59(18) . . ?
C7 C8 H8 119.8(14) . . ?
C9 C8 H8 120.6(14) . . ?
C10 C9 C8 120.05(18) . . ?
C10 C9 C15 120.95(18) . . ?
C8 C9 C15 118.98(18) . . ?
C11 C10 C9 120.42(18) . . ?
C11 C10 H10 118.8(13) . . ?
C9 C10 H10 120.7(13) . . ?
C10 C11 C12 119.40(19) . . ?
C10 C11 C14 119.10(18) . . ?
C12 C11 C14 121.50(18) . . ?
C11 C12 C7 120.41(18) . . ?
C11 C12 H12 120.0(13) . . ?
C7 C12 H12 119.5(13) . . ?
O2 C13 O1 123.92(19) . . ?
O2 C13 C7 123.62(19) . . ?
O1 C13 C7 112.45(17) . . ?
O6 C14 O5 123.79(18) . . ?
O6 C14 C11 119.37(17) . . ?
O5 C14 C11 116.84(17) . . ?
O4 C15 O3 123.80(19) . . ?
O4 C15 C9 122.62(19) . . ?
O3 C15 C9 113.58(18) . . ?
O7 C16 H16Z 113.2(15) . . ?
O7 C16 H16Y 106.6(16) . . ?
H16Z C16 H16Y 108(2) . . ?
O7 C16 H16X 111.0(16) . . ?
H16Z C16 H16X 106(2) . . ?
H16Y C16 H16X 112(2) . . ?
C1 N1 H1B 115(2) . . ?
C1 N1 H1A 114.7(19) . . ?
H1B N1 H1A 115(3) . . ?
C4 N2 H2Z 111.4(18) . . ?
C4 N2 H2Y 112.7(17) . . ?
H2Z N2 H2Y 103(2) . . ?
C4 N2 H2A 112.0(17) . . ?
H2Z N2 H2A 108(2) . . ?
H2Y N2 H2A 109(3) . . ?
C13 O1 H1W 108.8(19) . . ?
C15 O3 H3W 110.5(18) . . ?
C16 O7 H7Q 105(2) . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-3

