# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_dibr190
_database_code_depnum_ccdc_archive 'CCDC 1026670'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
 '4-pyridylazophenyl 4,6-dibromo-1,3-benzenediol'
;
_chemical_name_common            '4PAzP.4,6-diBr res 190'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Br2 O2, 2(C11 H9 N3)'
_chemical_formula_sum            'C28 H22 Br2 N6 O2'
_chemical_formula_weight         634.32

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.5422(13)
_cell_length_b                   19.6750(19)
_cell_length_c                   10.2805(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.796(3)
_cell_angle_gamma                90.00
_cell_volume                     2690.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.21

_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_absorpt_coefficient_mu    3.050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.552
_exptl_absorpt_correction_T_max  0.652
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33782
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.35
_reflns_number_total             4918
_reflns_number_gt                4035
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0198P)²+1.4494P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4918
_refine_ls_number_parameters     470
_refine_ls_number_restraints     433
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0529
_refine_ls_wR_factor_gt          0.0491
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002

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
N1A N 0.8671(3) 0.3171(2) 0.8977(5) 0.0342(10) Uani 0.759(4) 1 d PDU A 1
C1A C 0.7907(3) 0.3616(2) 0.8928(5) 0.0418(10) Uani 0.759(4) 1 d PDU A 1
H1A H 0.7889 0.4001 0.8368 0.050 Uiso 0.759(4) 1 calc PR A 1
C2A C 0.7151(3) 0.3542(2) 0.9648(4) 0.0381(9) Uani 0.759(4) 1 d PDU A 1
H2A H 0.6629 0.3869 0.9587 0.046 Uiso 0.759(4) 1 calc PR A 1
C3A C 0.8676(3) 0.2631(2) 0.9776(6) 0.0344(10) Uani 0.759(4) 1 d PDU A 1
H3A H 0.9209 0.2312 0.9832 0.041 Uiso 0.759(4) 1 calc PR A 1
C4A C 0.7943(3) 0.2516(2) 1.0521(5) 0.0321(8) Uani 0.759(4) 1 d PDU A 1
H4A H 0.7970 0.2124 1.1066 0.039 Uiso 0.759(4) 1 calc PR A 1
C5A C 0.7169(2) 0.2981(2) 1.0460(4) 0.0307(8) Uani 0.759(4) 1 d PDU A 1
N3A N 0.64386(18) 0.28191(14) 1.1272(3) 0.0379(7) Uani 0.759(4) 1 d PDU A 1
N4A N 0.56818(17) 0.31907(13) 1.1056(2) 0.0357(7) Uani 0.759(4) 1 d PDU A 1
C6A C 0.4940(2) 0.30066(18) 1.1824(3) 0.0289(8) Uani 0.759(4) 1 d PDU A 1
C7A C 0.5010(3) 0.2426(2) 1.2608(5) 0.0324(8) Uani 0.759(4) 1 d PDU A 1
H7A H 0.5579 0.2136 1.2681 0.039 Uiso 0.759(4) 1 calc PR A 1
C8A C 0.4243(3) 0.2276(2) 1.3281(5) 0.0370(10) Uani 0.759(4) 1 d PDU A 1
H8A H 0.4281 0.1880 1.3815 0.044 Uiso 0.759(4) 1 calc PR A 1
C9A C 0.4121(3) 0.34381(18) 1.1711(4) 0.0345(8) Uani 0.759(4) 1 d PDU A 1
H9A H 0.4080 0.3833 1.1172 0.041 Uiso 0.759(4) 1 calc PR A 1
C10A C 0.3358(3) 0.3284(2) 1.2402(5) 0.0421(11) Uani 0.759(4) 1 d PDU A 1
H110 H 0.2794 0.3577 1.2341 0.051 Uiso 0.759(4) 1 calc PR A 1
C11A C 0.3417(3) 0.2707(2) 1.3175(5) 0.0412(11) Uani 0.759(4) 1 d PDU A 1
H11A H 0.2890 0.2603 1.3637 0.049 Uiso 0.759(4) 1 calc PR A 1
N1B N 0.8768(11) 0.3016(9) 0.9117(19) 0.036(2) Uani 0.241(4) 1 d PDU A 2
C1B C 0.8181(11) 0.3569(7) 0.8839(14) 0.041(2) Uani 0.241(4) 1 d PDU A 2
H1B H 0.8370 0.3901 0.8260 0.050 Uiso 0.241(4) 1 calc PR A 2
C2B C 0.7324(9) 0.3683(6) 0.9343(13) 0.037(2) Uani 0.241(4) 1 d PDU A 2
H2B H 0.6932 0.4080 0.9113 0.045 Uiso 0.241(4) 1 calc PR A 2
C3B C 0.8493(11) 0.2564(8) 0.996(2) 0.032(2) Uani 0.241(4) 1 d PDU A 2
H3B H 0.8900 0.2172 1.0184 0.039 Uiso 0.241(4) 1 calc PR A 2
C4B C 0.7644(9) 0.2641(6) 1.0513(15) 0.030(2) Uani 0.241(4) 1 d PDU A 2
H4B H 0.7477 0.2309 1.1107 0.036 Uiso 0.241(4) 1 calc PR A 2
C5B C 0.7046(8) 0.3202(6) 1.0197(13) 0.030(2) Uani 0.241(4) 1 d PDU A 2
N3B N 0.6141(5) 0.3254(4) 1.0735(7) 0.0332(17) Uani 0.241(4) 1 d PDU A 2
N4B N 0.6032(5) 0.2818(4) 1.1552(8) 0.0323(18) Uani 0.241(4) 1 d PDU A 2
C6B C 0.5112(6) 0.2841(5) 1.2041(9) 0.029(2) Uani 0.241(4) 1 d PDU A 2
C7B C 0.4858(9) 0.2335(6) 1.2876(15) 0.032(3) Uani 0.241(4) 1 d PDU A 2
H7B H 0.5300 0.1963 1.3128 0.038 Uiso 0.241(4) 1 calc PR A 2
C8B C 0.3967(11) 0.2379(7) 1.3328(17) 0.033(2) Uani 0.241(4) 1 d PDU A 2
H8B H 0.3792 0.2035 1.3893 0.040 Uiso 0.241(4) 1 calc PR A 2
C9B C 0.4468(9) 0.3378(6) 1.1662(14) 0.0326(16) Uani 0.241(4) 1 d PDU A 2
H9B H 0.4641 0.3722 1.1095 0.039 Uiso 0.241(4) 1 calc PR A 2
C10B C 0.3565(9) 0.3413(7) 1.2115(15) 0.035(3) Uani 0.241(4) 1 d PDU A 2
H10B H 0.3112 0.3777 1.1839 0.042 Uiso 0.241(4) 1 calc PR A 2
C11B C 0.3320(9) 0.2925(8) 1.2962(17) 0.035(3) Uani 0.241(4) 1 d PDU A 2
H11B H 0.2713 0.2960 1.3294 0.043 Uiso 0.241(4) 1 calc PR A 2
N2 N 1.07358(12) 0.06459(9) 0.70603(16) 0.0374(4) Uani 1 1 d . . .
N5 N 0.81782(12) 0.09104(8) 0.87975(16) 0.0370(4) Uani 1 1 d . . .
N6 N 0.79699(12) 0.04362(9) 0.95059(16) 0.0365(4) Uani 1 1 d . . .
C12 C 1.02654(16) 0.12417(11) 0.7081(2) 0.0402(5) Uani 1 1 d . . .
H12 H 1.0520 0.1623 0.6682 0.048 Uiso 1 1 calc R . .
C13 C 0.94310(15) 0.13327(11) 0.76474(19) 0.0379(5) Uani 1 1 d . . .
H13 H 0.9112 0.1764 0.7621 0.045 Uiso 1 1 calc R . .
C14 C 1.03769(15) 0.01245(11) 0.7671(2) 0.0387(5) Uani 1 1 d . . .
H14 H 1.0708 -0.0302 0.7681 0.046 Uiso 1 1 calc R . .
C15 C 0.95568(15) 0.01689(10) 0.8286(2) 0.0364(5) Uani 1 1 d . . .
H15 H 0.9336 -0.0213 0.8717 0.044 Uiso 1 1 calc R . .
C16 C 0.90667(14) 0.07871(10) 0.82542(18) 0.0322(4) Uani 1 1 d . . .
C17 C 0.70772(13) 0.05527(10) 1.00346(19) 0.0318(4) Uani 1 1 d . . .
C18 C 0.64072(14) 0.10803(11) 0.9644(2) 0.0378(5) Uani 1 1 d . . .
H18 H 0.6516 0.1389 0.8974 0.045 Uiso 1 1 calc R . .
C19 C 0.55804(15) 0.11514(11) 1.0241(2) 0.0433(5) Uani 1 1 d . . .
H19 H 0.5116 0.1510 0.9978 0.052 Uiso 1 1 calc R . .
C20 C 0.69103(15) 0.00948(11) 1.1000(2) 0.0418(5) Uani 1 1 d . . .
H20 H 0.7361 -0.0273 1.1249 0.050 Uiso 1 1 calc R . .
C21 C 0.60833(16) 0.01784(12) 1.1595(2) 0.0465(6) Uani 1 1 d . . .
H21 H 0.5971 -0.0128 1.2266 0.056 Uiso 1 1 calc R . .
C22 C 0.54241(15) 0.07036(11) 1.1218(2) 0.0435(5) Uani 1 1 d . . .
H22 H 0.4858 0.0759 1.1631 0.052 Uiso 1 1 calc R . .
Br1 Br 0.374436(16) 0.012814(12) 0.38427(2) 0.04833(8) Uani 1 1 d . . .
Br2 Br 0.139874(16) 0.198627(14) 0.03570(2) 0.05119(8) Uani 1 1 d . . .
O1 O 0.21165(10) 0.03844(7) 0.54532(13) 0.0421(4) Uani 1 1 d . . .
H1O H 0.1694 0.0478 0.5901 0.063 Uiso 1 1 d R . .
O2 O 0.00950(10) 0.19317(7) 0.24414(13) 0.0432(4) Uani 1 1 d . . .
H2O H -0.0293 0.1869 0.2953 0.065 Uiso 1 1 d R . .
C23 C 0.26029(13) 0.07020(10) 0.34389(19) 0.0315(4) Uani 1 1 d . . .
C24 C 0.19327(14) 0.07477(10) 0.43145(18) 0.0311(4) Uani 1 1 d . . .
C25 C 0.10982(13) 0.11653(10) 0.39724(18) 0.0310(4) Uani 1 1 d . . .
H25 H 0.0636 0.1201 0.4560 0.037 Uiso 1 1 calc R . .
C26 C 0.09179(13) 0.15325(10) 0.27998(18) 0.0301(4) Uani 1 1 d . . .
C27 C 0.16090(14) 0.14837(10) 0.19557(18) 0.0307(4) Uani 1 1 d . . .
C28 C 0.24413(13) 0.10656(10) 0.22705(18) 0.0314(4) Uani 1 1 d . . .
H28 H 0.2902 0.1029 0.1682 0.038 Uiso 1 1 calc R . .


_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
N1A C3A 1.342(4) . ?
N1A C1A 1.349(4) . ?
C1A C2A 1.379(5) . ?
C1A H1A 0.9500 . ?
C2A C5A 1.381(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.380(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(4) . ?
C4A H4A 0.9500 . ?
C5A N3A 1.444(4) . ?
N3A N4A 1.245(3) . ?
N4A C6A 1.436(3) . ?
C6A C9A 1.384(4) . ?
C6A C7A 1.391(4) . ?
C7A C8A 1.383(4) . ?
C7A H7A 0.9500 . ?
C8A C11A 1.391(5) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.393(4) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.379(5) . ?
C10A H110 0.9500 . ?
C11A H11A 0.9500 . ?
N1B C3B 1.341(8) . ?
N1B C1B 1.347(8) . ?
C1B C2B 1.375(8) . ?
C1B H1B 0.9500 . ?
C2B C5B 1.389(7) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.385(8) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.372(8) . ?
C4B H4B 0.9500 . ?
C5B N3B 1.440(6) . ?
N3B N4B 1.228(7) . ?
N4B C6B 1.429(6) . ?
C6B C9B 1.378(8) . ?
C6B C7B 1.398(7) . ?
C7B C8B 1.375(8) . ?
C7B H7B 0.9500 . ?
C8B C11B 1.393(8) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.389(8) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.378(8) . ?
C10B H10B 0.9500 . ?
C11B H11B 0.9500 . ?
N2 C12 1.336(3) . ?
N2 C14 1.340(3) . ?
N5 N6 1.248(2) . ?
N5 C16 1.439(2) . ?
N6 C17 1.434(2) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C16 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.388(3) . ?
C17 C20 1.390(3) . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 C22 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
Br1 C23 1.8964(18) . ?
Br2 C27 1.8933(19) . ?
O1 C24 1.354(2) . ?
O1 H1O 0.8198 . ?
O2 C26 1.357(2) . ?
O2 H2O 0.8203 . ?
C23 C28 1.380(3) . ?
C23 C24 1.396(2) . ?
C24 C25 1.388(3) . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.394(2) . ?
C27 C28 1.384(3) . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3A N1A C1A 116.9(3) . . ?
N1A C1A C2A 123.5(3) . . ?
N1A C1A H1A 118.2 . . ?
C2A C1A H1A 118.2 . . ?
C1A C2A C5A 118.5(3) . . ?
C1A C2A H2A 120.7 . . ?
C5A C2A H2A 120.7 . . ?
N1A C3A C4A 123.2(3) . . ?
N1A C3A H3A 118.4 . . ?
C4A C3A H3A 118.4 . . ?
C3A C4A C5A 118.9(3) . . ?
C3A C4A H4A 120.5 . . ?
C5A C4A H4A 120.5 . . ?
C2A C5A C4A 118.9(3) . . ?
C2A C5A N3A 126.1(3) . . ?
C4A C5A N3A 115.1(3) . . ?
N4A N3A C5A 113.4(3) . . ?
N3A N4A C6A 113.0(3) . . ?
C9A C6A C7A 121.3(3) . . ?
C9A C6A N4A 115.6(3) . . ?
C7A C6A N4A 123.1(3) . . ?
C8A C7A C6A 119.2(3) . . ?
C8A C7A H7A 120.4 . . ?
C6A C7A H7A 120.4 . . ?
C7A C8A C11A 120.0(3) . . ?
C7A C8A H8A 120.0 . . ?
C11A C8A H8A 120.0 . . ?
C6A C9A C10A 118.9(3) . . ?
C6A C9A H9A 120.6 . . ?
C10A C9A H9A 120.6 . . ?
C11A C10A C9A 120.3(3) . . ?
C11A C10A H110 119.8 . . ?
C9A C10A H110 119.8 . . ?
C10A C11A C8A 120.3(3) . . ?
C10A C11A H11A 119.8 . . ?
C8A C11A H11A 119.8 . . ?
C3B N1B C1B 116.7(6) . . ?
N1B C1B C2B 123.9(7) . . ?
N1B C1B H1B 118.1 . . ?
C2B C1B H1B 118.1 . . ?
C1B C2B C5B 118.4(6) . . ?
C1B C2B H2B 120.8 . . ?
C5B C2B H2B 120.8 . . ?
N1B C3B C4B 123.0(6) . . ?
N1B C3B H3B 118.5 . . ?
C4B C3B H3B 118.5 . . ?
C5B C4B C3B 119.4(6) . . ?
C5B C4B H4B 120.3 . . ?
C3B C4B H4B 120.3 . . ?
C4B C5B C2B 118.6(5) . . ?
C4B C5B N3B 118.2(7) . . ?
C2B C5B N3B 123.1(8) . . ?
N4B N3B C5B 115.7(6) . . ?
N3B N4B C6B 116.3(7) . . ?
C9B C6B C7B 120.3(5) . . ?
C9B C6B N4B 118.1(7) . . ?
C7B C6B N4B 121.6(7) . . ?
C8B C7B C6B 119.7(6) . . ?
C8B C7B H7B 120.2 . . ?
C6B C7B H7B 120.2 . . ?
C7B C8B C11B 120.3(6) . . ?
C7B C8B H8B 119.9 . . ?
C11B C8B H8B 119.9 . . ?
C6B C9B C10B 119.5(6) . . ?
C6B C9B H9B 120.3 . . ?
C10B C9B H9B 120.3 . . ?
C11B C10B C9B 120.6(6) . . ?
C11B C10B H10B 119.7 . . ?
C9B C10B H10B 119.7 . . ?
C10B C11B C8B 119.7(6) . . ?
C10B C11B H11B 120.2 . . ?
C8B C11B H11B 120.2 . . ?
C12 N2 C14 116.63(17) . . ?
N6 N5 C16 113.41(16) . . ?
N5 N6 C17 113.61(16) . . ?
N2 C12 C13 123.53(19) . . ?
N2 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C12 C13 C16 118.81(19) . . ?
C12 C13 H13 120.6 . . ?
C16 C13 H13 120.6 . . ?
N2 C14 C15 124.04(19) . . ?
N2 C14 H14 118.0 . . ?
C15 C14 H14 118.0 . . ?
C14 C15 C16 117.96(19) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C13 C16 C15 118.99(17) . . ?
C13 C16 N5 116.13(17) . . ?
C15 C16 N5 124.87(18) . . ?
C18 C17 C20 120.44(18) . . ?
C18 C17 N6 124.18(18) . . ?
C20 C17 N6 115.38(17) . . ?
C19 C18 C17 119.19(19) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C22 120.4(2) . . ?
C18 C19 H19 119.8 . . ?
C22 C19 H19 119.8 . . ?
C21 C20 C17 119.5(2) . . ?
C21 C20 H20 120.3 . . ?
C17 C20 H20 120.3 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C19 120.32(19) . . ?
C21 C22 H22 119.8 . . ?
C19 C22 H22 119.8 . . ?
C24 O1 H1O 109.4 . . ?
C26 O2 H2O 109.3 . . ?
C28 C23 C24 120.78(17) . . ?
C28 C23 Br1 119.28(13) . . ?
C24 C23 Br1 119.93(14) . . ?
O1 C24 C25 122.71(16) . . ?
O1 C24 C23 119.15(17) . . ?
C25 C24 C23 118.14(17) . . ?
C26 C25 C24 122.06(16) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
O2 C26 C25 122.64(16) . . ?
O2 C26 C27 118.94(17) . . ?
C25 C26 C27 118.41(17) . . ?
C28 C27 C26 120.51(17) . . ?
C28 C27 Br2 119.80(13) . . ?
C26 C27 Br2 119.68(14) . . ?
C23 C28 C27 120.08(16) . . ?
C23 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3A N1A C1A C2A 0.1(6) . . . . ?
N1A C1A C2A C5A -0.3(5) . . . . ?
C1A N1A C3A C4A 0.5(8) . . . . ?
N1A C3A C4A C5A -0.8(8) . . . . ?
C1A C2A C5A C4A 0.0(6) . . . . ?
C1A C2A C5A N3A -179.5(4) . . . . ?
C3A C4A C5A C2A 0.5(7) . . . . ?
C3A C4A C5A N3A -179.9(4) . . . . ?
C2A C5A N3A N4A 9.2(5) . . . . ?
C4A C5A N3A N4A -170.4(3) . . . . ?
C5A N3A N4A C6A 177.3(3) . . . . ?
N3A N4A C6A C9A 174.6(3) . . . . ?
N3A N4A C6A C7A -7.1(5) . . . . ?
C9A C6A C7A C8A 0.4(6) . . . . ?
N4A C6A C7A C8A -177.9(4) . . . . ?
C6A C7A C8A C11A -0.4(7) . . . . ?
C7A C6A C9A C10A 0.1(6) . . . . ?
N4A C6A C9A C10A 178.5(3) . . . . ?
C6A C9A C10A C11A -0.6(6) . . . . ?
C9A C10A C11A C8A 0.6(7) . . . . ?
C7A C8A C11A C10A -0.1(8) . . . . ?
C3B N1B C1B C2B -1.3(18) . . . . ?
N1B C1B C2B C5B 0.4(14) . . . . ?
C1B N1B C3B C4B 1(3) . . . . ?
N1B C3B C4B C5B 0(3) . . . . ?
C3B C4B C5B C2B -1(2) . . . . ?
C3B C4B C5B N3B 177.0(15) . . . . ?
C1B C2B C5B C4B 1(2) . . . . ?
C1B C2B C5B N3B -177.1(11) . . . . ?
C4B C5B N3B N4B 7.2(17) . . . . ?
C2B C5B N3B N4B -174.8(13) . . . . ?
C5B N3B N4B C6B -176.7(9) . . . . ?
N3B N4B C6B C9B -5.9(13) . . . . ?
N3B N4B C6B C7B 173.8(11) . . . . ?
C9B C6B C7B C8B -1(2) . . . . ?
N4B C6B C7B C8B 179.7(14) . . . . ?
C6B C7B C8B C11B 0(3) . . . . ?
C7B C6B C9B C10B 0(2) . . . . ?
N4B C6B C9B C10B 179.6(12) . . . . ?
C6B C9B C10B C11B 2(2) . . . . ?
C9B C10B C11B C8B -2(3) . . . . ?
C7B C8B C11B C10B 2(3) . . . . ?
C16 N5 N6 C17 -179.17(15) . . . . ?
C14 N2 C12 C13 -2.2(3) . . . . ?
N2 C12 C13 C16 1.4(3) . . . . ?
C12 N2 C14 C15 1.0(3) . . . . ?
N2 C14 C15 C16 0.9(3) . . . . ?
C12 C13 C16 C15 0.7(3) . . . . ?
C12 C13 C16 N5 -178.46(18) . . . . ?
C14 C15 C16 C13 -1.7(3) . . . . ?
C14 C15 C16 N5 177.29(18) . . . . ?
N6 N5 C16 C13 -169.66(17) . . . . ?
N6 N5 C16 C15 11.3(3) . . . . ?
N5 N6 C17 C18 10.1(3) . . . . ?
N5 N6 C17 C20 -169.66(18) . . . . ?
C20 C17 C18 C19 1.0(3) . . . . ?
N6 C17 C18 C19 -178.72(19) . . . . ?
C17 C18 C19 C22 0.2(3) . . . . ?
C18 C17 C20 C21 -1.6(3) . . . . ?
N6 C17 C20 C21 178.13(19) . . . . ?
C17 C20 C21 C22 1.1(3) . . . . ?
C20 C21 C22 C19 0.1(3) . . . . ?
C18 C19 C22 C21 -0.8(3) . . . . ?
C28 C23 C24 O1 -179.89(17) . . . . ?
Br1 C23 C24 O1 0.7(3) . . . . ?
C28 C23 C24 C25 0.4(3) . . . . ?
Br1 C23 C24 C25 -179.01(14) . . . . ?
O1 C24 C25 C26 -179.75(18) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C24 C25 C26 O2 178.64(18) . . . . ?
C24 C25 C26 C27 -0.9(3) . . . . ?
O2 C26 C27 C28 -178.06(17) . . . . ?
C25 C26 C27 C28 1.5(3) . . . . ?
O2 C26 C27 Br2 1.3(2) . . . . ?
C25 C26 C27 Br2 -179.18(14) . . . . ?
C24 C23 C28 C27 0.2(3) . . . . ?
Br1 C23 C28 C27 179.60(14) . . . . ?
C26 C27 C28 C23 -1.2(3) . . . . ?
Br2 C27 C28 C23 179.50(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_dibr290
_database_code_depnum_ccdc_archive 'CCDC 1026671'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
 '4-pyridylazophenyl 4,6-dibromo-1,3-benzenediol'
;
_chemical_name_common            '4PAzP.4,6-diBr res 290'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Br2 O2, 2(C11 H9 N3)'
_chemical_formula_sum            'C28 H22 Br2 N6 O2'
_chemical_formula_weight         634.32

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.5095(15)
_cell_length_b                   20.268(2)
_cell_length_c                   9.5541(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.192(5)
_cell_angle_gamma                90.00
_cell_volume                     2787.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    9383
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35

_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_absorpt_coefficient_mu    2.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14404
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         25.34
_reflns_number_total             5086
_reflns_number_gt                2726
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0363P)²+0.5978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5086
_refine_ls_number_parameters     470
_refine_ls_number_restraints     451
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.971
_refine_ls_shift/su_max          0.004
_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
N1A N 0.9123(11) -0.1623(11) -0.999(2) 0.093(4) Uani 0.438(8) 1 d PDU A 1
C1A C 0.9194(9) -0.2035(9) -0.891(2) 0.097(4) Uani 0.438(8) 1 d PDU A 1
H1A H 0.9738 -0.2279 -0.8706 0.117 Uiso 0.438(8) 1 calc PR A 1
C2A C 0.8493(8) -0.2121(8) -0.8055(16) 0.083(3) Uani 0.438(8) 1 d PDU A 1
H2A H 0.8577 -0.2409 -0.7293 0.100 Uiso 0.438(8) 1 calc PR A 1
C3A C 0.8356(13) -0.1255(10) -1.0181(19) 0.099(4) Uani 0.438(8) 1 d PDU A 1
H3A H 0.8312 -0.0933 -1.0879 0.119 Uiso 0.438(8) 1 calc PR A 1
C4A C 0.7618(10) -0.1329(9) -0.9395(17) 0.092(4) Uani 0.438(8) 1 d PDU A 1
H4A H 0.7086 -0.1072 -0.9590 0.110 Uiso 0.438(8) 1 calc PR A 1
C5A C 0.7684(6) -0.1778(8) -0.8343(15) 0.071(3) Uani 0.438(8) 1 d PDU A 1
N3A N 0.6927(4) -0.1874(4) -0.7536(9) 0.086(3) Uani 0.438(8) 1 d PDU A 1
N4A N 0.6223(5) -0.1591(5) -0.7981(10) 0.083(3) Uani 0.438(8) 1 d PDU A 1
C6A C 0.5418(5) -0.1726(6) -0.7297(13) 0.079(3) Uani 0.438(8) 1 d PDU A 1
C7A C 0.5449(8) -0.2165(8) -0.6209(15) 0.103(4) Uani 0.438(8) 1 d PDU A 1
H7A H 0.5999 -0.2386 -0.5898 0.124 Uiso 0.438(8) 1 calc PR A 1
C8A C 0.4638(10) -0.2285(10) -0.5556(17) 0.120(4) Uani 0.438(8) 1 d PDU A 1
H8A H 0.4657 -0.2561 -0.4774 0.144 Uiso 0.438(8) 1 calc PR A 1
C9A C 0.4613(7) -0.1408(7) -0.7745(18) 0.098(4) Uani 0.438(8) 1 d PDU A 1
H9A H 0.4605 -0.1087 -0.8441 0.117 Uiso 0.438(8) 1 calc PR A 1
C10A C 0.3803(7) -0.1554(8) -0.718(2) 0.111(4) Uani 0.438(8) 1 d PDU A 1
H10A H 0.3245 -0.1357 -0.7546 0.133 Uiso 0.438(8) 1 calc PR A 1
C11A C 0.3831(11) -0.1985(14) -0.611(3) 0.120(4) Uani 0.438(8) 1 d PDU A 1
H11A H 0.3287 -0.2080 -0.5726 0.144 Uiso 0.438(8) 1 calc PR A 1
N1B N 0.9162(9) -0.1766(8) -0.9882(17) 0.087(3) Uani 0.562(8) 1 d PDU A 2
C1B C 0.8990(7) -0.2105(7) -0.8761(17) 0.094(3) Uani 0.562(8) 1 d PDU A 2
H1B H 0.9439 -0.2398 -0.8353 0.113 Uiso 0.562(8) 1 calc PR A 2
C2B C 0.8166(7) -0.2045(6) -0.8163(13) 0.091(3) Uani 0.562(8) 1 d PDU A 2
H2B H 0.8074 -0.2294 -0.7375 0.109 Uiso 0.562(8) 1 calc PR A 2
C3B C 0.8492(9) -0.1357(7) -1.0437(15) 0.096(3) Uani 0.562(8) 1 d PDU A 2
H3B H 0.8587 -0.1121 -1.1243 0.115 Uiso 0.562(8) 1 calc PR A 2
C4B C 0.7665(8) -0.1264(7) -0.9880(14) 0.094(3) Uani 0.562(8) 1 d PDU A 2
H4B H 0.7230 -0.0961 -1.0285 0.113 Uiso 0.562(8) 1 calc PR A 2
C5B C 0.7499(6) -0.1622(6) -0.8732(12) 0.074(3) Uani 0.562(8) 1 d PDU A 2
N3B N 0.6606(4) -0.1559(4) -0.8257(8) 0.090(2) Uani 0.562(8) 1 d PDU A 2
N4B N 0.6454(4) -0.1940(3) -0.7349(7) 0.088(2) Uani 0.562(8) 1 d PDU A 2
C6B C 0.5539(5) -0.1905(5) -0.6920(9) 0.076(3) Uani 0.562(8) 1 d PDU A 2
C7B C 0.5282(7) -0.2388(6) -0.6032(13) 0.105(3) Uani 0.562(8) 1 d PDU A 2
H7B H 0.5708 -0.2708 -0.5677 0.127 Uiso 0.562(8) 1 calc PR A 2
C8B C 0.4368(8) -0.2395(7) -0.5663(14) 0.119(3) Uani 0.562(8) 1 d PDU A 2
H8B H 0.4168 -0.2735 -0.5121 0.143 Uiso 0.562(8) 1 calc PR A 2
C9B C 0.4931(7) -0.1432(5) -0.7391(12) 0.093(3) Uani 0.562(8) 1 d PDU A 2
H9B H 0.5105 -0.1110 -0.8001 0.111 Uiso 0.562(8) 1 calc PR A 2
C10B C 0.4043(6) -0.1415(6) -0.6982(16) 0.115(4) Uani 0.562(8) 1 d PDU A 2
H10B H 0.3632 -0.1079 -0.7299 0.138 Uiso 0.562(8) 1 calc PR A 2
C11B C 0.3787(9) -0.1888(11) -0.613(3) 0.119(3) Uani 0.562(8) 1 d PDU A 2
H11B H 0.3198 -0.1870 -0.5840 0.143 Uiso 0.562(8) 1 calc PR A 2
N2 N 1.0912(2) -0.04013(18) -0.7475(3) 0.1019(9) Uani 1 1 d . . .
N5 N 0.8659(2) -0.08721(15) -0.5288(3) 0.0958(8) Uani 1 1 d . . .
N6 N 0.8022(2) -0.04739(15) -0.5378(3) 0.0938(8) Uani 1 1 d . . .
C12 C 1.0924(3) -0.0887(2) -0.6559(5) 0.1181(13) Uani 1 1 d . . .
H12 H 1.1462 -0.1140 -0.6391 0.142 Uiso 1 1 calc R . .
C13 C 1.0192(3) -0.1047(2) -0.5832(4) 0.1146(13) Uani 1 1 d . . .
H13 H 1.0237 -0.1395 -0.5193 0.137 Uiso 1 1 calc R . .
C14 C 1.0137(3) -0.0053(2) -0.7676(4) 0.1112(12) Uani 1 1 d . . .
H14 H 1.0109 0.0295 -0.8313 0.133 Uiso 1 1 calc R . .
C15 C 0.9370(2) -0.0173(2) -0.7004(4) 0.1033(11) Uani 1 1 d . . .
H15 H 0.8842 0.0089 -0.7184 0.124 Uiso 1 1 calc R . .
C16 C 0.9397(2) -0.06796(19) -0.6076(4) 0.0871(10) Uani 1 1 d . . .
C17 C 0.7277(2) -0.0662(2) -0.4597(4) 0.0882(10) Uani 1 1 d . . .
C18 C 0.7196(3) -0.1260(2) -0.4012(5) 0.1230(14) Uani 1 1 d . . .
H18 H 0.7637 -0.1585 -0.4107 0.148 Uiso 1 1 calc R . .
C19 C 0.6465(4) -0.1393(2) -0.3276(5) 0.1486(18) Uani 1 1 d . . .
H19 H 0.6415 -0.1808 -0.2876 0.178 Uiso 1 1 calc R . .
C20 C 0.6621(3) -0.0193(2) -0.4482(5) 0.1364(16) Uani 1 1 d . . .
H20 H 0.6658 0.0215 -0.4916 0.164 Uiso 1 1 calc R . .
C21 C 0.5886(3) -0.0334(3) -0.3697(6) 0.1443(18) Uani 1 1 d . . .
H21 H 0.5447 -0.0011 -0.3576 0.173 Uiso 1 1 calc R . .
C22 C 0.5818(3) -0.0930(3) -0.3127(5) 0.1296(15) Uani 1 1 d . . .
H22 H 0.5324 -0.1027 -0.2627 0.155 Uiso 1 1 calc R . .
Br1 Br 0.61053(2) 0.02987(2) 0.08876(5) 0.1216(2) Uani 1 1 d . . .
Br2 Br 0.82296(2) 0.23404(2) 0.37412(4) 0.10252(17) Uani 1 1 d . . .
O1 O 0.76936(14) 0.03090(11) -0.0867(3) 0.1008(7) Uani 1 1 d . . .
H1O H 0.8073 0.0363 -0.1426 0.151 Uiso 1 1 d R . .
O2 O 0.95576(13) 0.19622(11) 0.1688(2) 0.0983(7) Uani 1 1 d . . .
H2O H 0.9904 0.1869 0.1102 0.147 Uiso 1 1 d R . .
C23 C 0.71789(18) 0.08376(16) 0.1100(4) 0.0784(9) Uani 1 1 d . . .
C24 C 0.7845(2) 0.07559(16) 0.0178(4) 0.0766(9) Uani 1 1 d . . .
C25 C 0.86357(19) 0.11362(16) 0.0391(4) 0.0765(9) Uani 1 1 d . . .
H25 H 0.9089 0.1082 -0.0206 0.092 Uiso 1 1 calc R . .
C26 C 0.87761(19) 0.15933(16) 0.1456(3) 0.0740(8) Uani 1 1 d . . .
C27 C 0.80923(19) 0.16791(15) 0.2329(3) 0.0754(8) Uani 1 1 d . . .
C28 C 0.7297(2) 0.13011(16) 0.2144(4) 0.0801(9) Uani 1 1 d . . .
H28 H 0.6839 0.1362 0.2732 0.096 Uiso 1 1 calc R . .


_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
N1A C1A 1.323(8) . ?
N1A C3A 1.334(8) . ?
C1A C2A 1.390(8) . ?
C1A H1A 0.9300 . ?
C2A C5A 1.361(8) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.391(8) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.351(9) . ?
C4A H4A 0.9300 . ?
C5A N3A 1.432(7) . ?
N3A N4A 1.201(7) . ?
N4A C6A 1.434(7) . ?
C6A C9A 1.355(9) . ?
C6A C7A 1.366(9) . ?
C7A C8A 1.420(9) . ?
C7A H7A 0.9300 . ?
C8A C11A 1.365(10) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.384(8) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.347(9) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9300 . ?
N1B C1B 1.323(7) . ?
N1B C3B 1.335(7) . ?
C1B C2B 1.393(8) . ?
C1B H1B 0.9300 . ?
C2B C5B 1.354(8) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.385(8) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.362(8) . ?
C4B H4B 0.9300 . ?
C5B N3B 1.431(6) . ?
N3B N4B 1.203(6) . ?
N4B C6B 1.439(6) . ?
C6B C9B 1.343(8) . ?
C6B C7B 1.376(8) . ?
C7B C8B 1.414(9) . ?
C7B H7B 0.9300 . ?
C8B C11B 1.368(10) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.393(8) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.343(8) . ?
C10B H10B 0.9300 . ?
C11B H11B 0.9300 . ?
N2 C12 1.316(5) . ?
N2 C14 1.322(4) . ?
N5 N6 1.222(3) . ?
N5 C16 1.438(4) . ?
N6 C17 1.439(4) . ?
C12 C13 1.378(5) . ?
C12 H12 0.9300 . ?
C13 C16 1.369(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.354(5) . ?
C15 H15 0.9300 . ?
C17 C18 1.347(5) . ?
C17 C20 1.359(5) . ?
C18 C19 1.370(5) . ?
C18 H18 0.9300 . ?
C19 C22 1.347(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.408(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.334(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
Br1 C23 1.893(3) . ?
Br2 C27 1.894(3) . ?
O1 C24 1.346(4) . ?
O1 H1O 0.8204 . ?
O2 C26 1.353(3) . ?
O2 H2O 0.8196 . ?
C23 C28 1.365(4) . ?
C23 C24 1.397(4) . ?
C24 C25 1.376(4) . ?
C25 C26 1.372(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(4) . ?
C27 C28 1.378(4) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C3A 116.3(6) . . ?
N1A C1A C2A 123.0(7) . . ?
N1A C1A H1A 118.5 . . ?
C2A C1A H1A 118.5 . . ?
C5A C2A C1A 119.6(7) . . ?
C5A C2A H2A 120.2 . . ?
C1A C2A H2A 120.2 . . ?
N1A C3A C4A 123.5(7) . . ?
N1A C3A H3A 118.3 . . ?
C4A C3A H3A 118.3 . . ?
C5A C4A C3A 119.0(7) . . ?
C5A C4A H4A 120.5 . . ?
C3A C4A H4A 120.5 . . ?
C4A C5A C2A 118.3(6) . . ?
C4A C5A N3A 120.2(8) . . ?
C2A C5A N3A 121.5(9) . . ?
N4A N3A C5A 114.9(7) . . ?
N3A N4A C6A 117.0(7) . . ?
C9A C6A C7A 119.6(6) . . ?
C9A C6A N4A 119.0(9) . . ?
C7A C6A N4A 121.3(8) . . ?
C6A C7A C8A 119.8(7) . . ?
C6A C7A H7A 120.1 . . ?
C8A C7A H7A 120.1 . . ?
C11A C8A C7A 118.2(7) . . ?
C11A C8A H8A 120.9 . . ?
C7A C8A H8A 120.9 . . ?
C6A C9A C10A 121.1(7) . . ?
C6A C9A H9A 119.4 . . ?
C10A C9A H9A 119.4 . . ?
C11A C10A C9A 119.3(7) . . ?
C11A C10A H10A 120.4 . . ?
C9A C10A H10A 120.4 . . ?
C10A C11A C8A 121.7(7) . . ?
C10A C11A H11A 119.1 . . ?
C8A C11A H11A 119.1 . . ?
C1B N1B C3B 116.3(6) . . ?
N1B C1B C2B 123.0(6) . . ?
N1B C1B H1B 118.5 . . ?
C2B C1B H1B 118.5 . . ?
C5B C2B C1B 119.9(6) . . ?
C5B C2B H2B 120.1 . . ?
C1B C2B H2B 120.1 . . ?
N1B C3B C4B 123.7(6) . . ?
N1B C3B H3B 118.2 . . ?
C4B C3B H3B 118.2 . . ?
C5B C4B C3B 119.1(6) . . ?
C5B C4B H4B 120.5 . . ?
C3B C4B H4B 120.5 . . ?
C2B C5B C4B 118.1(6) . . ?
C2B C5B N3B 123.9(8) . . ?
C4B C5B N3B 117.8(8) . . ?
N4B N3B C5B 115.3(6) . . ?
N3B N4B C6B 115.7(6) . . ?
C9B C6B C7B 119.8(6) . . ?
C9B C6B N4B 122.0(7) . . ?
C7B C6B N4B 118.1(8) . . ?
C6B C7B C8B 119.7(7) . . ?
C6B C7B H7B 120.1 . . ?
C8B C7B H7B 120.1 . . ?
C11B C8B C7B 118.1(7) . . ?
C11B C8B H8B 121.0 . . ?
C7B C8B H8B 121.0 . . ?
C6B C9B C10B 121.1(6) . . ?
C6B C9B H9B 119.5 . . ?
C10B C9B H9B 119.5 . . ?
C11B C10B C9B 119.3(6) . . ?
C11B C10B H10B 120.4 . . ?
C9B C10B H10B 120.4 . . ?
C10B C11B C8B 121.9(6) . . ?
C10B C11B H11B 119.1 . . ?
C8B C11B H11B 119.1 . . ?
C12 N2 C14 115.9(3) . . ?
N6 N5 C16 113.0(3) . . ?
N5 N6 C17 113.5(3) . . ?
N2 C12 C13 124.3(4) . . ?
N2 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C16 C13 C12 118.2(4) . . ?
C16 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
N2 C14 C15 124.2(4) . . ?
N2 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C16 C15 C14 118.8(4) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C13 118.6(3) . . ?
C15 C16 N5 125.9(3) . . ?
C13 C16 N5 115.5(4) . . ?
C18 C17 C20 119.8(4) . . ?
C18 C17 N6 124.4(3) . . ?
C20 C17 N6 115.8(4) . . ?
C17 C18 C19 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C22 C19 C18 120.8(5) . . ?
C22 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C17 C20 C21 119.1(4) . . ?
C17 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C22 C21 C20 120.0(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C19 120.0(4) . . ?
C21 C22 H22 120.0 . . ?
C19 C22 H22 120.0 . . ?
C24 O1 H1O 109.4 . . ?
C26 O2 H2O 109.4 . . ?
C28 C23 C24 120.6(3) . . ?
C28 C23 Br1 120.1(2) . . ?
C24 C23 Br1 119.3(3) . . ?
O1 C24 C25 122.9(3) . . ?
O1 C24 C23 119.1(3) . . ?
C25 C24 C23 118.1(3) . . ?
C26 C25 C24 122.1(3) . . ?
C26 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
O2 C26 C25 122.6(3) . . ?
O2 C26 C27 118.7(3) . . ?
C25 C26 C27 118.7(3) . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 Br2 119.8(2) . . ?
C26 C27 Br2 119.9(2) . . ?
C23 C28 C27 120.2(3) . . ?
C23 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3A N1A C1A C2A 3.9(18) . . . . ?
N1A C1A C2A C5A 1.2(14) . . . . ?
C1A N1A C3A C4A -6(3) . . . . ?
N1A C3A C4A C5A 2(3) . . . . ?
C3A C4A C5A C2A 3(3) . . . . ?
C3A C4A C5A N3A -178.7(18) . . . . ?
C1A C2A C5A C4A -5(2) . . . . ?
C1A C2A C5A N3A 177.0(13) . . . . ?
C4A C5A N3A N4A 9(2) . . . . ?
C2A C5A N3A N4A -173.1(15) . . . . ?
C5A N3A N4A C6A 173.7(10) . . . . ?
N3A N4A C6A C9A 178.7(13) . . . . ?
N3A N4A C6A C7A -1.3(14) . . . . ?
C9A C6A C7A C8A -0.1(19) . . . . ?
N4A C6A C7A C8A 179.9(13) . . . . ?
C6A C7A C8A C11A 4(3) . . . . ?
C7A C6A C9A C10A -4(2) . . . . ?
N4A C6A C9A C10A 175.6(12) . . . . ?
C6A C9A C10A C11A 5(3) . . . . ?
C9A C10A C11A C8A 0(4) . . . . ?
C7A C8A C11A C10A -4(4) . . . . ?
C3B N1B C1B C2B -0.6(13) . . . . ?
N1B C1B C2B C5B -0.1(12) . . . . ?
C1B N1B C3B C4B 2(2) . . . . ?
N1B C3B C4B C5B -2(2) . . . . ?
C1B C2B C5B C4B -0.4(17) . . . . ?
C1B C2B C5B N3B 175.4(11) . . . . ?
C3B C4B C5B C2B 2(2) . . . . ?
C3B C4B C5B N3B -174.5(13) . . . . ?
C2B C5B N3B N4B -4.2(17) . . . . ?
C4B C5B N3B N4B 171.7(11) . . . . ?
C5B N3B N4B C6B -176.7(8) . . . . ?
N3B N4B C6B C9B -6.9(12) . . . . ?
N3B N4B C6B C7B 171.0(9) . . . . ?
C9B C6B C7B C8B 2.2(15) . . . . ?
N4B C6B C7B C8B -175.8(10) . . . . ?
C6B C7B C8B C11B -5(2) . . . . ?
C7B C6B C9B C10B 0.9(15) . . . . ?
N4B C6B C9B C10B 178.8(9) . . . . ?
C6B C9B C10B C11B -1(2) . . . . ?
C9B C10B C11B C8B -1(3) . . . . ?
C7B C8B C11B C10B 4(3) . . . . ?
C16 N5 N6 C17 179.8(3) . . . . ?
C14 N2 C12 C13 0.3(6) . . . . ?
N2 C12 C13 C16 0.2(7) . . . . ?
C12 N2 C14 C15 -0.4(6) . . . . ?
N2 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 C13 0.7(6) . . . . ?
C14 C15 C16 N5 -180.0(3) . . . . ?
C12 C13 C16 C15 -0.8(6) . . . . ?
C12 C13 C16 N5 179.9(3) . . . . ?
N6 N5 C16 C15 -9.6(5) . . . . ?
N6 N5 C16 C13 169.7(3) . . . . ?
N5 N6 C17 C18 -10.6(5) . . . . ?
N5 N6 C17 C20 170.3(4) . . . . ?
C20 C17 C18 C19 -1.4(7) . . . . ?
N6 C17 C18 C19 179.5(4) . . . . ?
C17 C18 C19 C22 0.0(8) . . . . ?
C18 C17 C20 C21 2.7(7) . . . . ?
N6 C17 C20 C21 -178.1(4) . . . . ?
C17 C20 C21 C22 -2.8(8) . . . . ?
C20 C21 C22 C19 1.5(8) . . . . ?
C18 C19 C22 C21 -0.1(8) . . . . ?
C28 C23 C24 O1 -177.9(3) . . . . ?
Br1 C23 C24 O1 2.0(4) . . . . ?
C28 C23 C24 C25 2.6(5) . . . . ?
Br1 C23 C24 C25 -177.5(2) . . . . ?
O1 C24 C25 C26 179.5(3) . . . . ?
C23 C24 C25 C26 -1.0(5) . . . . ?
C24 C25 C26 O2 178.9(3) . . . . ?
C24 C25 C26 C27 -0.9(5) . . . . ?
O2 C26 C27 C28 -178.5(3) . . . . ?
C25 C26 C27 C28 1.4(5) . . . . ?
O2 C26 C27 Br2 3.8(4) . . . . ?
C25 C26 C27 Br2 -176.4(2) . . . . ?
C24 C23 C28 C27 -2.2(5) . . . . ?
Br1 C23 C28 C27 177.9(2) . . . . ?
C26 C27 C28 C23 0.2(5) . . . . ?
Br2 C27 C28 C23 177.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_dicl170
_database_code_depnum_ccdc_archive 'CCDC 1026672'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

__audit_creation_method          
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
 '4-pyridylazophenyl 4,6-dichloro-1,3-benzenediol'
;
_chemical_name_common            '4PAzP.4,6-diCl res 170'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Cl2 O2, 2(C11 H9 N3)'
_chemical_formula_sum            'C28 H22 Cl2 N6 O2'
_chemical_formula_weight         545.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.6181(16)
_cell_length_b                   15.7722(16)
_cell_length_c                   10.6301(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.137(5)
_cell_angle_gamma                90.00
_cell_volume                     2608.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    11640
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22464
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         27.88
_reflns_number_total             6177
_reflns_number_gt                4701
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0479P)²+0.8713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6177
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
N1 N 0.40931(9) 0.05345(10) 0.24349(14) 0.0417(3) Uani 1 1 d . . .
C1 C 0.40929(11) 0.10210(12) 0.34609(17) 0.0430(4) Uani 1 1 d . . .
H1 H 0.3578 0.1309 0.3610 0.052 Uiso 1 1 calc R . .
C2 C 0.48068(11) 0.11282(11) 0.43217(16) 0.0397(4) Uani 1 1 d . . .
H2 H 0.4778 0.1469 0.5053 0.048 Uiso 1 1 calc R . .
N3 N 0.62977(9) 0.08254(9) 0.49757(13) 0.0371(3) Uani 1 1 d . . .
C3 C 0.48212(12) 0.01305(12) 0.22487(17) 0.0453(4) Uani 1 1 d . . .
H3 H 0.4824 -0.0233 0.1537 0.054 Uiso 1 1 calc R . .
N4 N 0.69837(9) 0.07344(9) 0.44668(13) 0.0399(3) Uani 1 1 d . . .
C4 C 0.55698(11) 0.02105(11) 0.30307(17) 0.0428(4) Uani 1 1 d . . .
H4 H 0.6078 -0.0079 0.2852 0.051 Uiso 1 1 calc R . .
C5 C 0.55597(10) 0.07255(10) 0.40858(15) 0.0347(4) Uani 1 1 d . . .
C6 C 0.77465(11) 0.07527(11) 0.53121(16) 0.0379(4) Uani 1 1 d . . .
C7 C 0.85096(12) 0.08039(13) 0.47451(19) 0.0488(4) Uani 1 1 d . . .
H7 H 0.8502 0.0835 0.3852 0.059 Uiso 1 1 calc R . .
C8 C 0.92830(12) 0.08089(13) 0.5488(2) 0.0545(5) Uani 1 1 d . . .
H8 H 0.9809 0.0857 0.5108 0.065 Uiso 1 1 calc R . .
C9 C 0.77507(11) 0.06854(11) 0.66168(17) 0.0426(4) Uani 1 1 d . . .
H9 H 0.7226 0.0644 0.7001 0.051 Uiso 1 1 calc R . .
C10 C 0.85273(13) 0.06789(13) 0.73477(19) 0.0522(5) Uani 1 1 d . . .
H10 H 0.8540 0.0630 0.8240 0.063 Uiso 1 1 calc R . .
C11 C 0.92890(12) 0.07442(13) 0.6778(2) 0.0550(5) Uani 1 1 d . . .
H11 H 0.9822 0.0744 0.7286 0.066 Uiso 1 1 calc R . .
N2 N 0.41202(9) 0.81532(10) 1.05460(13) 0.0405(3) Uani 1 1 d . . .
N5 N 0.14719(8) 0.80942(9) 0.93851(13) 0.0367(3) Uani 1 1 d . . .
N6 N 0.12664(8) 0.79797(9) 0.82320(13) 0.0368(3) Uani 1 1 d . . .
C12 C 0.38407(11) 0.83365(13) 0.93558(17) 0.0457(4) Uani 1 1 d . . .
H12 H 0.4255 0.8481 0.8789 0.055 Uiso 1 1 calc R . .
C13 C 0.29830(11) 0.83293(12) 0.88950(16) 0.0419(4) Uani 1 1 d . . .
H13 H 0.2812 0.8478 0.8044 0.050 Uiso 1 1 calc R . .
C14 C 0.35284(11) 0.79530(12) 1.13251(17) 0.0433(4) Uani 1 1 d . . .
H14 H 0.3713 0.7833 1.2182 0.052 Uiso 1 1 calc R . .
C15 C 0.26579(11) 0.79113(11) 1.09479(16) 0.0404(4) Uani 1 1 d . . .
H15 H 0.2258 0.7757 1.1530 0.048 Uiso 1 1 calc R . .
C16 C 0.23834(10) 0.80986(10) 0.97119(15) 0.0346(3) Uani 1 1 d . . .
C17 C 0.03640(10) 0.80498(11) 0.78827(15) 0.0347(3) Uani 1 1 d . . .
C18 C -0.02021(10) 0.84642(11) 0.86156(16) 0.0378(4) Uani 1 1 d . . .
H18 H -0.0001 0.8696 0.9413 0.045 Uiso 1 1 calc R . .
C19 C -0.10614(11) 0.85360(12) 0.81711(18) 0.0445(4) Uani 1 1 d . . .
H19 H -0.1451 0.8823 0.8661 0.053 Uiso 1 1 calc R . .
C20 C 0.00744(11) 0.77173(12) 0.67135(17) 0.0435(4) Uani 1 1 d . . .
H20 H 0.0465 0.7448 0.6206 0.052 Uiso 1 1 calc R . .
C21 C -0.07909(11) 0.77812(13) 0.62891(18) 0.0478(4) Uani 1 1 d . . .
H21 H -0.0996 0.7543 0.5498 0.057 Uiso 1 1 calc R . .
C22 C -0.13511(11) 0.81900(12) 0.70148(18) 0.0460(4) Uani 1 1 d . . .
H22 H -0.1942 0.8235 0.6719 0.055 Uiso 1 1 calc R . .
Cl1 Cl 0.12611(3) 0.01749(3) 0.88680(4) 0.04579(13) Uani 1 1 d . . .
Cl2 Cl 0.30205(3) 0.22066(3) 0.59311(4) 0.04848(13) Uani 1 1 d . . .
O1 O 0.27897(7) 0.02935(8) 1.06294(11) 0.0410(3) Uani 1 1 d . . .
H1O H 0.3206 0.0404 1.1159 0.062 Uiso 1 1 d R . .
O2 O 0.44031(7) 0.20220(8) 0.79333(12) 0.0436(3) Uani 1 1 d . . .
H2O H 0.4792 0.1946 0.8521 0.065 Uiso 1 1 d R . .
C23 C 0.28796(10) 0.07208(10) 0.95511(15) 0.0335(3) Uani 1 1 d . . .
C24 C 0.36232(10) 0.11608(10) 0.93154(15) 0.0331(3) Uani 1 1 d . . .
H24 H 0.4101 0.1156 0.9935 0.040 Uiso 1 1 calc R . .
C25 C 0.36838(10) 0.16049(10) 0.82007(15) 0.0340(3) Uani 1 1 d . . .
C26 C 0.29736(10) 0.16149(10) 0.73041(15) 0.0347(3) Uani 1 1 d . . .
C27 C 0.22359(10) 0.11751(10) 0.75045(15) 0.0361(4) Uani 1 1 d . . .
H27 H 0.1760 0.1178 0.6882 0.043 Uiso 1 1 calc R . .
C28 C 0.21926(10) 0.07299(10) 0.86149(16) 0.0344(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
N1 C1 1.334(2) . ?
N1 C3 1.334(2) . ?
C1 C2 1.388(2) . ?
C1 H1 0.9500 . ?
C2 C5 1.379(2) . ?
C2 H2 0.9500 . ?
N3 N4 1.251(2) . ?
N3 C5 1.433(2) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9500 . ?
N4 C6 1.427(2) . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C6 C7 1.385(3) . ?
C6 C9 1.390(3) . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C11 1.374(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
N2 C12 1.333(2) . ?
N2 C14 1.333(2) . ?
N5 N6 1.2521(19) . ?
N5 C16 1.435(2) . ?
N6 C17 1.429(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C16 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(2) . ?
C15 H15 0.9500 . ?
C17 C20 1.387(2) . ?
C17 C18 1.393(2) . ?
C18 C19 1.387(2) . ?
C18 H18 0.9500 . ?
C19 C22 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
Cl1 C28 1.7393(16) . ?
Cl2 C26 1.7394(17) . ?
O1 C23 1.3478(19) . ?
O1 H1O 0.8393 . ?
O2 C25 1.3537(19) . ?
O2 H2O 0.8402 . ?
C23 C24 1.395(2) . ?
C23 C28 1.397(2) . ?
C24 C25 1.387(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.396(2) . ?
C26 C27 1.378(2) . ?
C27 C28 1.380(2) . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 117.32(15) . . ?
N1 C1 C2 123.39(16) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C5 C2 C1 118.14(16) . . ?
C5 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
N4 N3 C5 111.80(14) . . ?
N1 C3 C4 123.73(17) . . ?
N1 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
N3 N4 C6 115.11(14) . . ?
C3 C4 C5 118.11(17) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C2 C5 C4 119.26(15) . . ?
C2 C5 N3 118.55(15) . . ?
C4 C5 N3 122.14(15) . . ?
C7 C6 C9 120.73(16) . . ?
C7 C6 N4 115.44(16) . . ?
C9 C6 N4 123.77(16) . . ?
C8 C7 C6 119.57(19) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C11 C8 C7 119.81(19) . . ?
C11 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C6 119.17(18) . . ?
C10 C9 H9 120.4 . . ?
C6 C9 H9 120.4 . . ?
C9 C10 C11 119.92(19) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C8 C11 C10 120.79(17) . . ?
C8 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C12 N2 C14 117.06(15) . . ?
N6 N5 C16 113.54(13) . . ?
N5 N6 C17 113.80(13) . . ?
N2 C12 C13 123.95(16) . . ?
N2 C12 H12 118.0 . . ?
C13 C12 H12 118.0 . . ?
C16 C13 C12 117.93(16) . . ?
C16 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
N2 C14 C15 123.29(17) . . ?
N2 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C16 C15 C14 118.68(16) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C13 119.05(15) . . ?
C15 C16 N5 116.57(15) . . ?
C13 C16 N5 124.24(15) . . ?
C20 C17 C18 120.43(15) . . ?
C20 C17 N6 116.00(15) . . ?
C18 C17 N6 123.48(15) . . ?
C19 C18 C17 119.42(16) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C22 C19 C18 119.99(17) . . ?
C22 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C17 C20 C21 119.54(17) . . ?
C17 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.02(17) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C19 120.58(16) . . ?
C21 C22 H22 119.7 . . ?
C19 C22 H22 119.7 . . ?
C23 O1 H1O 109.5 . . ?
C25 O2 H2O 109.5 . . ?
O1 C23 C24 123.61(14) . . ?
O1 C23 C28 118.63(14) . . ?
C24 C23 C28 117.77(15) . . ?
C25 C24 C23 121.76(14) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
O2 C25 C24 123.10(14) . . ?
O2 C25 C26 118.33(15) . . ?
C24 C25 C26 118.56(15) . . ?
C27 C26 C25 120.86(15) . . ?
C27 C26 Cl2 119.90(12) . . ?
C25 C26 Cl2 119.23(13) . . ?
C26 C27 C28 119.61(14) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C27 C28 C23 121.41(15) . . ?
C27 C28 Cl1 119.61(12) . . ?
C23 C28 Cl1 118.98(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 0.5(3) . . . . ?
N1 C1 C2 C5 1.5(3) . . . . ?
C1 N1 C3 C4 -2.1(3) . . . . ?
C5 N3 N4 C6 -174.86(14) . . . . ?
N1 C3 C4 C5 1.5(3) . . . . ?
C1 C2 C5 C4 -2.1(3) . . . . ?
C1 C2 C5 N3 -179.38(15) . . . . ?
C3 C4 C5 C2 0.7(3) . . . . ?
C3 C4 C5 N3 177.87(16) . . . . ?
N4 N3 C5 C2 -153.71(16) . . . . ?
N4 N3 C5 C4 29.1(2) . . . . ?
N3 N4 C6 C7 -169.02(16) . . . . ?
N3 N4 C6 C9 13.9(2) . . . . ?
C9 C6 C7 C8 -1.6(3) . . . . ?
N4 C6 C7 C8 -178.79(18) . . . . ?
C6 C7 C8 C11 1.4(3) . . . . ?
C7 C6 C9 C10 0.7(3) . . . . ?
N4 C6 C9 C10 177.63(17) . . . . ?
C6 C9 C10 C11 0.4(3) . . . . ?
C7 C8 C11 C10 -0.4(3) . . . . ?
C9 C10 C11 C8 -0.5(3) . . . . ?
C16 N5 N6 C17 -174.73(13) . . . . ?
C14 N2 C12 C13 0.0(3) . . . . ?
N2 C12 C13 C16 -1.6(3) . . . . ?
C12 N2 C14 C15 1.4(3) . . . . ?
N2 C14 C15 C16 -1.1(3) . . . . ?
C14 C15 C16 C13 -0.6(3) . . . . ?
C14 C15 C16 N5 -176.51(16) . . . . ?
C12 C13 C16 C15 1.9(3) . . . . ?
C12 C13 C16 N5 177.41(16) . . . . ?
N6 N5 C16 C15 -157.05(16) . . . . ?
N6 N5 C16 C13 27.3(2) . . . . ?
N5 N6 C17 C20 -163.72(16) . . . . ?
N5 N6 C17 C18 19.8(2) . . . . ?
C20 C17 C18 C19 0.5(3) . . . . ?
N6 C17 C18 C19 176.88(16) . . . . ?
C17 C18 C19 C22 0.7(3) . . . . ?
C18 C17 C20 C21 -1.6(3) . . . . ?
N6 C17 C20 C21 -178.23(17) . . . . ?
C17 C20 C21 C22 1.5(3) . . . . ?
C20 C21 C22 C19 -0.3(3) . . . . ?
C18 C19 C22 C21 -0.8(3) . . . . ?
O1 C23 C24 C25 -178.88(15) . . . . ?
C28 C23 C24 C25 0.9(2) . . . . ?
C23 C24 C25 O2 -178.49(15) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
O2 C25 C26 C27 177.53(15) . . . . ?
C24 C25 C26 C27 -1.7(2) . . . . ?
O2 C25 C26 Cl2 -3.5(2) . . . . ?
C24 C25 C26 Cl2 177.19(12) . . . . ?
C25 C26 C27 C28 1.1(2) . . . . ?
Cl2 C26 C27 C28 -177.83(13) . . . . ?
C26 C27 C28 C23 0.6(2) . . . . ?
C26 C27 C28 Cl1 179.98(13) . . . . ?
O1 C23 C28 C27 178.20(15) . . . . ?
C24 C23 C28 C27 -1.5(2) . . . . ?
O1 C23 C28 Cl1 -1.2(2) . . . . ?
C24 C23 C28 Cl1 179.07(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_dicl250
_database_code_depnum_ccdc_archive 'CCDC 1026673'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

__audit_creation_method          
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
 '4-pyridylazophenyl 4,6-dichloro-1,3-benzenediol'
;
_chemical_name_common            '4PAzP.4,6-diCl res 250'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Cl2 O2, 2(C11 H9 N3)'
_chemical_formula_sum            'C28 H22 Cl2 N6 O2'
_chemical_formula_weight         545.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.6347(16)
_cell_length_b                   15.9890(16)
_cell_length_c                   10.6460(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.252(5)
_cell_angle_gamma                90.00
_cell_volume                     2650.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    7888
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14597
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.86
_diffrn_reflns_theta_max         25.48
_reflns_number_total             4718
_reflns_number_gt                3080
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0461P)²+0.9809P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4718
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.58938(15) 0.05309(15) 0.2579(2) 0.0645(6) Uani 1 1 d . . .
C1 C 0.51736(19) 0.01265(19) 0.2751(3) 0.0712(8) Uani 1 1 d . . .
H1 H 0.5173 -0.0233 0.3450 0.085 Uiso 1 1 calc R . .
C2 C 0.44245(18) 0.02016(17) 0.1965(3) 0.0663(8) Uani 1 1 d . . .
H2 H 0.3924 -0.0088 0.2132 0.080 Uiso 1 1 calc R . .
N3 N 0.36959(14) 0.08121(13) 0.00284(19) 0.0577(6) Uani 1 1 d . . .
C3 C 0.58884(18) 0.10146(19) 0.1564(3) 0.0677(8) Uani 1 1 d . . .
H3 H 0.6395 0.1302 0.1423 0.081 Uiso 1 1 calc R . .
N4 N 0.30112(15) 0.07189(14) 0.0522(2) 0.0628(6) Uani 1 1 d . . .
C4 C 0.51791(17) 0.11191(17) 0.0705(3) 0.0626(7) Uani 1 1 d . . .
H4 H 0.5207 0.1458 -0.0012 0.075 Uiso 1 1 calc R . .
C5 C 0.44339(16) 0.07163(16) 0.0924(2) 0.0541(7) Uani 1 1 d . . .
C6 C 0.22513(17) 0.07411(17) -0.0327(3) 0.0588(7) Uani 1 1 d . . .
C7 C 0.14922(19) 0.0792(2) 0.0222(3) 0.0778(9) Uani 1 1 d . . .
H7 H 0.1495 0.0818 0.1104 0.093 Uiso 1 1 calc R . .
C8 C 0.07230(19) 0.0803(2) -0.0531(4) 0.0883(10) Uani 1 1 d . . .
H8 H 0.0201 0.0849 -0.0163 0.106 Uiso 1 1 calc R . .
C9 C 0.22515(18) 0.06858(17) -0.1621(3) 0.0676(8) Uani 1 1 d . . .
H9 H 0.2773 0.0651 -0.1992 0.081 Uiso 1 1 calc R . .
C10 C 0.1484(2) 0.0682(2) -0.2364(3) 0.0820(9) Uani 1 1 d . . .
H10 H 0.1479 0.0635 -0.3244 0.098 Uiso 1 1 calc R . .
C11 C 0.0725(2) 0.0748(2) -0.1814(4) 0.0869(10) Uani 1 1 d . . .
H11 H 0.0201 0.0755 -0.2324 0.104 Uiso 1 1 calc R . .
N2 N 0.41252(14) 0.18517(15) 0.5525(2) 0.0642(6) Uani 1 1 d . . .
N5 N 0.14741(13) 0.18981(14) 0.4363(2) 0.0609(6) Uani 1 1 d . . .
N6 N 0.12736(13) 0.20073(14) 0.3219(2) 0.0608(6) Uani 1 1 d . . .
C12 C 0.35342(18) 0.20522(19) 0.6282(3) 0.0700(8) Uani 1 1 d . . .
H12 H 0.3716 0.2177 0.7127 0.084 Uiso 1 1 calc R . .
C13 C 0.26660(17) 0.20893(18) 0.5911(3) 0.0656(8) Uani 1 1 d . . .
H13 H 0.2271 0.2241 0.6485 0.079 Uiso 1 1 calc R . .
C14 C 0.38446(18) 0.1669(2) 0.4347(3) 0.0730(8) Uani 1 1 d . . .
H14 H 0.4253 0.1526 0.3788 0.088 Uiso 1 1 calc R . .
C15 C 0.29872(17) 0.16751(19) 0.3884(3) 0.0670(8) Uani 1 1 d . . .
H15 H 0.2818 0.1529 0.3043 0.080 Uiso 1 1 calc R . .
C16 C 0.23956(16) 0.19004(16) 0.4689(2) 0.0549(7) Uani 1 1 d . . .
C17 C 0.03647(16) 0.19437(16) 0.2875(3) 0.0568(7) Uani 1 1 d . . .
C18 C -0.01995(17) 0.15404(17) 0.3602(3) 0.0621(7) Uani 1 1 d . . .
H18 H -0.0001 0.1316 0.4391 0.075 Uiso 1 1 calc R . .
C19 C -0.10547(17) 0.14697(19) 0.3164(3) 0.0720(8) Uani 1 1 d . . .
H19 H -0.1440 0.1192 0.3648 0.086 Uiso 1 1 calc R . .
C20 C 0.00749(18) 0.22631(19) 0.1713(3) 0.0706(8) Uani 1 1 d . . .
H20 H 0.0461 0.2522 0.1210 0.085 Uiso 1 1 calc R . .
C21 C -0.07834(19) 0.2202(2) 0.1289(3) 0.0771(9) Uani 1 1 d . . .
H21 H -0.0985 0.2432 0.0504 0.092 Uiso 1 1 calc R . .
C22 C -0.13397(18) 0.18082(19) 0.2012(3) 0.0744(9) Uani 1 1 d . . .
H22 H -0.1924 0.1768 0.1720 0.089 Uiso 1 1 calc R . .
Cl1 Cl 0.87260(4) 0.01811(5) 0.61534(7) 0.0746(3) Uani 1 1 d . . .
Cl2 Cl 0.69740(5) 0.21949(5) 0.90650(7) 0.0785(3) Uani 1 1 d . . .
O1 O 0.72062(11) 0.03043(12) 0.43842(16) 0.0657(5) Uani 1 1 d . . .
H1O H 0.6788 0.0410 0.3855 0.098 Uiso 1 1 d R . .
O2 O 0.56031(11) 0.20280(12) 0.70508(17) 0.0688(5) Uani 1 1 d . . .
H2O H 0.5217 0.1961 0.6458 0.103 Uiso 1 1 d R . .
C23 C 0.71180(15) 0.07298(16) 0.5459(2) 0.0519(6) Uani 1 1 d . . .
C24 C 0.77982(15) 0.07344(16) 0.6397(2) 0.0531(6) Uani 1 1 d . . .
C25 C 0.77548(16) 0.11767(16) 0.7496(2) 0.0579(7) Uani 1 1 d . . .
H25 H 0.8226 0.1180 0.8112 0.069 Uiso 1 1 calc R . .
C26 C 0.70222(16) 0.16141(16) 0.7693(2) 0.0545(6) Uani 1 1 d . . .
C27 C 0.63190(16) 0.16074(16) 0.6791(2) 0.0536(6) Uani 1 1 d . . .
C28 C 0.63834(15) 0.11700(15) 0.5685(2) 0.0522(6) Uani 1 1 d . . .
H28 H 0.5915 0.1171 0.5066 0.063 Uiso 1 1 calc R . .


_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 1.326(3) . ?
N1 C3 1.328(3) . ?
C1 C2 1.381(4) . ?
C1 H1 0.9400 . ?
C2 C5 1.381(4) . ?
C2 H2 0.9400 . ?
N3 N4 1.244(3) . ?
N3 C5 1.436(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9400 . ?
N4 C6 1.426(3) . ?
C4 C5 1.370(4) . ?
C4 H4 0.9400 . ?
C6 C7 1.372(4) . ?
C6 C9 1.380(4) . ?
C7 C8 1.383(4) . ?
C7 H7 0.9400 . ?
C8 C11 1.369(5) . ?
C8 H8 0.9400 . ?
C9 C10 1.375(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.375(4) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
N2 C12 1.320(3) . ?
N2 C14 1.323(3) . ?
N5 N6 1.241(3) . ?
N5 C16 1.451(3) . ?
N6 C17 1.438(3) . ?
C12 C13 1.380(4) . ?
C12 H12 0.9400 . ?
C13 C16 1.364(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.366(4) . ?
C15 H15 0.9400 . ?
C17 C20 1.376(4) . ?
C17 C18 1.385(4) . ?
C18 C19 1.380(4) . ?
C18 H18 0.9400 . ?
C19 C22 1.376(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.380(4) . ?
C20 H20 0.9400 . ?
C21 C22 1.367(4) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
Cl1 C24 1.738(3) . ?
Cl2 C26 1.738(3) . ?
O1 C23 1.349(3) . ?
O1 H1O 0.8402 . ?
O2 C27 1.356(3) . ?
O2 H2O 0.8400 . ?
C23 C28 1.387(3) . ?
C23 C24 1.390(3) . ?
C24 C25 1.375(3) . ?
C25 C26 1.375(3) . ?
C25 H25 0.9400 . ?
C26 C27 1.392(3) . ?
C27 C28 1.381(3) . ?
C28 H28 0.9400 . ?

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 C3 117.0(2) . . ?
N1 C1 C2 123.9(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C5 C2 C1 117.9(3) . . ?
C5 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
N4 N3 C5 112.2(2) . . ?
N1 C3 C4 123.6(3) . . ?
N1 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
N3 N4 C6 115.4(2) . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C2 119.3(2) . . ?
C4 C5 N3 118.7(2) . . ?
C2 C5 N3 122.0(2) . . ?
C7 C6 C9 120.5(2) . . ?
C7 C6 N4 115.8(2) . . ?
C9 C6 N4 123.7(3) . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C11 C8 C7 119.8(3) . . ?
C11 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C6 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C6 C9 H9 120.2 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C8 C11 C10 120.7(3) . . ?
C8 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C12 N2 C14 116.3(2) . . ?
N6 N5 C16 113.0(2) . . ?
N5 N6 C17 113.3(2) . . ?
N2 C12 C13 124.1(3) . . ?
N2 C12 H12 117.9 . . ?
C13 C12 H12 117.9 . . ?
C16 C13 C12 118.3(3) . . ?
C16 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
N2 C14 C15 124.2(3) . . ?
N2 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C16 C15 C14 117.9(3) . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15 121.1 . . ?
C13 C16 C15 119.2(2) . . ?
C13 C16 N5 116.3(2) . . ?
C15 C16 N5 124.3(2) . . ?
C20 C17 C18 120.1(2) . . ?
C20 C17 N6 116.1(2) . . ?
C18 C17 N6 123.7(2) . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C22 C19 C18 119.6(3) . . ?
C22 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C17 C20 C21 119.9(3) . . ?
C17 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 119.9(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C19 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C19 C22 H22 119.6 . . ?
C23 O1 H1O 109.5 . . ?
C27 O2 H2O 109.5 . . ?
O1 C23 C28 123.6(2) . . ?
O1 C23 C24 118.7(2) . . ?
C28 C23 C24 117.7(2) . . ?
C25 C24 C23 121.3(2) . . ?
C25 C24 Cl1 119.70(18) . . ?
C23 C24 Cl1 119.0(2) . . ?
C24 C25 C26 119.9(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 120.5(2) . . ?
C25 C26 Cl2 120.06(19) . . ?
C27 C26 Cl2 119.4(2) . . ?
O2 C27 C28 123.4(2) . . ?
O2 C27 C26 118.1(2) . . ?
C28 C27 C26 118.5(2) . . ?
C27 C28 C23 122.1(2) . . ?
C27 C28 H28 119.0 . . ?
C23 C28 H28 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C1 C2 -2.1(4) . . . . ?
N1 C1 C2 C5 1.3(5) . . . . ?
C1 N1 C3 C4 0.6(4) . . . . ?
C5 N3 N4 C6 -175.4(2) . . . . ?
N1 C3 C4 C5 1.5(4) . . . . ?
C3 C4 C5 C2 -2.2(4) . . . . ?
C3 C4 C5 N3 -179.2(2) . . . . ?
C1 C2 C5 C4 0.9(4) . . . . ?
C1 C2 C5 N3 177.8(2) . . . . ?
N4 N3 C5 C4 -153.3(2) . . . . ?
N4 N3 C5 C2 29.8(3) . . . . ?
N3 N4 C6 C7 -168.6(3) . . . . ?
N3 N4 C6 C9 13.7(4) . . . . ?
C9 C6 C7 C8 -1.2(5) . . . . ?
N4 C6 C7 C8 -179.0(3) . . . . ?
C6 C7 C8 C11 1.3(5) . . . . ?
C7 C6 C9 C10 0.0(4) . . . . ?
N4 C6 C9 C10 177.7(3) . . . . ?
C6 C9 C10 C11 1.1(5) . . . . ?
C7 C8 C11 C10 -0.1(5) . . . . ?
C9 C10 C11 C8 -1.1(5) . . . . ?
C16 N5 N6 C17 175.6(2) . . . . ?
C14 N2 C12 C13 -0.8(4) . . . . ?
N2 C12 C13 C16 0.6(5) . . . . ?
C12 N2 C14 C15 -0.2(5) . . . . ?
N2 C14 C15 C16 1.4(5) . . . . ?
C12 C13 C16 C15 0.6(4) . . . . ?
C12 C13 C16 N5 176.4(2) . . . . ?
C14 C15 C16 C13 -1.5(4) . . . . ?
C14 C15 C16 N5 -176.9(3) . . . . ?
N6 N5 C16 C13 156.9(2) . . . . ?
N6 N5 C16 C15 -27.6(4) . . . . ?
N5 N6 C17 C20 163.9(2) . . . . ?
N5 N6 C17 C18 -20.3(4) . . . . ?
C20 C17 C18 C19 -0.8(4) . . . . ?
N6 C17 C18 C19 -176.4(3) . . . . ?
C17 C18 C19 C22 -0.6(4) . . . . ?
C18 C17 C20 C21 1.9(4) . . . . ?
N6 C17 C20 C21 177.8(3) . . . . ?
C17 C20 C21 C22 -1.5(5) . . . . ?
C20 C21 C22 C19 0.0(5) . . . . ?
C18 C19 C22 C21 1.0(5) . . . . ?
O1 C23 C24 C25 178.1(2) . . . . ?
C28 C23 C24 C25 -1.7(4) . . . . ?
O1 C23 C24 Cl1 -0.9(3) . . . . ?
C28 C23 C24 Cl1 179.39(19) . . . . ?
C23 C24 C25 C26 1.1(4) . . . . ?
Cl1 C24 C25 C26 -179.9(2) . . . . ?
C24 C25 C26 C27 0.5(4) . . . . ?
C24 C25 C26 Cl2 -178.4(2) . . . . ?
C25 C26 C27 O2 178.0(2) . . . . ?
Cl2 C26 C27 O2 -3.0(3) . . . . ?
C25 C26 C27 C28 -1.6(4) . . . . ?
Cl2 C26 C27 C28 177.37(19) . . . . ?
O2 C27 C28 C23 -178.5(2) . . . . ?
C26 C27 C28 C23 1.1(4) . . . . ?
O1 C23 C28 C27 -179.2(2) . . . . ?
C24 C23 C28 C27 0.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.48
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_dicl270
_database_code_depnum_ccdc_archive 'CCDC 1026674'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
 '4-pyridylazophenyl 4,6-dichloro-1,3-benzenediol'
;
_chemical_name_common            '4PAzP.4,6-diCl res 270'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Cl2 O2, 2(C11 H9 N3)'
_chemical_formula_sum            'C28 H22 Cl2 N6 O2'
_chemical_formula_weight         545.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.4187(14)
_cell_length_b                   19.4064(19)
_cell_length_c                   9.7692(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.552(5)
_cell_angle_gamma                90.00
_cell_volume                     2720.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    8142
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29749
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         25.32
_reflns_number_total             4938
_reflns_number_gt                3065
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0408P)²+0.7586P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4938
_refine_ls_number_parameters     470
_refine_ls_number_restraints     441
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
N1A N -0.4191(7) 0.1663(8) 0.9951(13) 0.078(2) Uani 0.655(6) 1 d PDU A 1
C1A C -0.3415(7) 0.1293(7) 1.0225(11) 0.089(2) Uani 0.655(6) 1 d PDU A 1
H1A H -0.3381 0.0997 1.0977 0.107 Uiso 0.655(6) 1 calc PR A 1
C2A C -0.2656(5) 0.1322(6) 0.9459(10) 0.0813(17) Uani 0.655(6) 1 d PDU A 1
H2A H -0.2119 0.1070 0.9717 0.098 Uiso 0.655(6) 1 calc PR A 1
C3A C -0.4248(5) 0.2037(6) 0.8801(11) 0.079(2) Uani 0.655(6) 1 d PDU A 1
H3A H -0.4796 0.2278 0.8551 0.095 Uiso 0.655(6) 1 calc PR A 1
C4A C -0.3530(5) 0.2085(5) 0.7959(8) 0.0733(15) Uani 0.655(6) 1 d PDU A 1
H4A H -0.3598 0.2352 0.7165 0.088 Uiso 0.655(6) 1 calc PR A 1
C5A C -0.2716(3) 0.1731(5) 0.8311(6) 0.0614(16) Uani 0.655(6) 1 d PDU A 1
N3A N -0.1956(2) 0.1821(2) 0.7485(4) 0.0759(12) Uani 0.655(6) 1 d PDU A 1
N4A N -0.1216(2) 0.1583(3) 0.8003(5) 0.0786(14) Uani 0.655(6) 1 d PDU A 1
C6A C -0.0437(3) 0.1704(4) 0.7240(8) 0.0695(17) Uani 0.655(6) 1 d PDU A 1
C7A C 0.0390(5) 0.1417(4) 0.7767(9) 0.105(2) Uani 0.655(6) 1 d PDU A 1
H7A H 0.0401 0.1127 0.8528 0.127 Uiso 0.655(6) 1 calc PR A 1
C8A C 0.1211(4) 0.1552(5) 0.7183(11) 0.116(3) Uani 0.655(6) 1 d PDU A 1
H8A H 0.1773 0.1372 0.7573 0.140 Uiso 0.655(6) 1 calc PR A 1
C9A C -0.0448(4) 0.2110(4) 0.6098(8) 0.096(2) Uani 0.655(6) 1 d PDU A 1
H9A H -0.1001 0.2317 0.5739 0.115 Uiso 0.655(6) 1 calc PR A 1
C10A C 0.0364(5) 0.2214(5) 0.5474(8) 0.113(2) Uani 0.655(6) 1 d PDU A 1
H10A H 0.0346 0.2467 0.4664 0.136 Uiso 0.655(6) 1 calc PR A 1
C11A C 0.1184(7) 0.1949(11) 0.603(2) 0.109(2) Uani 0.655(6) 1 d PDU A 1
H11A H 0.1730 0.2039 0.5631 0.131 Uiso 0.655(6) 1 calc PR A 1
N1B N -0.4227(13) 0.1788(17) 0.974(3) 0.077(4) Uani 0.345(6) 1 d PDU A 2
C1B C -0.3550(13) 0.1401(13) 1.038(2) 0.088(4) Uani 0.345(6) 1 d PDU A 2
H1B H -0.3651 0.1211 1.1228 0.106 Uiso 0.345(6) 1 calc PR A 2
C2B C -0.2711(11) 0.1266(12) 0.9864(18) 0.086(4) Uani 0.345(6) 1 d PDU A 2
H2B H -0.2293 0.0951 1.0294 0.103 Uiso 0.345(6) 1 calc PR A 2
C3B C -0.4029(9) 0.2096(11) 0.859(2) 0.075(3) Uani 0.345(6) 1 d PDU A 2
H3B H -0.4473 0.2386 0.8137 0.090 Uiso 0.345(6) 1 calc PR A 2
C4B C -0.3192(8) 0.2006(8) 0.8018(13) 0.070(3) Uani 0.345(6) 1 d PDU A 2
H4B H -0.3096 0.2213 0.7184 0.083 Uiso 0.345(6) 1 calc PR A 2
C5B C -0.2507(7) 0.1609(9) 0.8694(14) 0.066(3) Uani 0.345(6) 1 d PDU A 2
N3B N -0.1616(5) 0.1535(5) 0.8183(10) 0.080(3) Uani 0.345(6) 1 d PDU A 2
N4B N -0.1468(5) 0.1912(4) 0.7233(7) 0.078(2) Uani 0.345(6) 1 d PDU A 2
C6B C -0.0555(6) 0.1884(7) 0.6795(14) 0.066(3) Uani 0.345(6) 1 d PDU A 2
C7B C 0.0078(8) 0.1432(7) 0.7405(15) 0.088(3) Uani 0.345(6) 1 d PDU A 2
H7B H -0.0096 0.1135 0.8083 0.105 Uiso 0.345(6) 1 calc PR A 2
C8B C 0.0985(7) 0.1409(9) 0.702(2) 0.106(4) Uani 0.345(6) 1 d PDU A 2
H8B H 0.1397 0.1071 0.7377 0.127 Uiso 0.345(6) 1 calc PR A 2
C9B C -0.0270(8) 0.2347(8) 0.5858(15) 0.095(4) Uani 0.345(6) 1 d PDU A 2
H9B H -0.0699 0.2650 0.5413 0.114 Uiso 0.345(6) 1 calc PR A 2
C10B C 0.0646(9) 0.2364(9) 0.5573(16) 0.108(4) Uani 0.345(6) 1 d PDU A 2
H10B H 0.0846 0.2704 0.4998 0.129 Uiso 0.345(6) 1 calc PR A 2
C11B C 0.1261(13) 0.188(2) 0.613(5) 0.112(4) Uani 0.345(6) 1 d PDU A 2
H11B H 0.1871 0.1883 0.5896 0.135 Uiso 0.345(6) 1 calc PR A 2
N2 N 0.40522(14) 0.03915(13) 0.7489(2) 0.0905(6) Uani 1 1 d . . .
N5 N 0.62974(13) 0.08684(10) 0.52230(19) 0.0783(5) Uani 1 1 d . . .
N6 N 0.69754(13) 0.04790(10) 0.53608(19) 0.0777(5) Uani 1 1 d . . .
C12 C 0.48493(18) 0.00526(15) 0.7714(3) 0.0944(8) Uani 1 1 d . . .
H12 H 0.4891 -0.0289 0.8386 0.113 Uiso 1 1 calc R . .
C13 C 0.56170(16) 0.01714(14) 0.7024(2) 0.0841(7) Uani 1 1 d . . .
H13 H 0.6160 -0.0084 0.7218 0.101 Uiso 1 1 calc R . .
C14 C 0.40125(17) 0.08741(16) 0.6535(3) 0.0996(8) Uani 1 1 d . . .
H14 H 0.3459 0.1118 0.6358 0.119 Uiso 1 1 calc R . .
C15 C 0.47448(16) 0.10382(13) 0.5784(3) 0.0908(7) Uani 1 1 d . . .
H15 H 0.4686 0.1385 0.5124 0.109 Uiso 1 1 calc R . .
C16 C 0.55625(15) 0.06780(12) 0.6035(2) 0.0715(6) Uani 1 1 d . . .
C17 C 0.77087(15) 0.06632(13) 0.4551(2) 0.0733(6) Uani 1 1 d . . .
C18 C 0.84146(19) 0.02025(16) 0.4502(3) 0.1169(10) Uani 1 1 d . . .
H18 H 0.8414 -0.0203 0.5008 0.140 Uiso 1 1 calc R . .
C19 C 0.9141(2) 0.0336(2) 0.3692(4) 0.1270(11) Uani 1 1 d . . .
H19 H 0.9613 0.0014 0.3640 0.152 Uiso 1 1 calc R . .
C20 C 0.77372(19) 0.12580(15) 0.3831(3) 0.1024(9) Uani 1 1 d . . .
H20 H 0.7262 0.1580 0.3863 0.123 Uiso 1 1 calc R . .
C21 C 0.8463(2) 0.13903(17) 0.3055(3) 0.1248(11) Uani 1 1 d . . .
H21 H 0.8477 0.1802 0.2569 0.150 Uiso 1 1 calc R . .
C22 C 0.9158(2) 0.09259(19) 0.2992(3) 0.1082(9) Uani 1 1 d . . .
H22 H 0.9647 0.1018 0.2462 0.130 Uiso 1 1 calc R . .
Cl1 Cl 0.31706(4) 0.22803(4) 0.36473(7) 0.0962(2) Uani 1 1 d . . .
Cl2 Cl 0.11068(5) 0.03065(4) 0.09171(9) 0.1168(3) Uani 1 1 d . . .
O1 O 0.44836(10) 0.20009(9) 0.16261(16) 0.0927(5) Uani 1 1 d . . .
H1O H 0.4842 0.1897 0.1057 0.139 Uiso 1 1 d R . .
O2 O 0.26069(10) 0.02975(8) -0.08851(17) 0.0908(5) Uani 1 1 d . . .
H2O H 0.3026 0.0327 -0.1391 0.136 Uiso 1 1 d R . .
C23 C 0.30192(14) 0.16793(11) 0.2325(2) 0.0682(6) Uani 1 1 d . . .
C24 C 0.37026(13) 0.16113(11) 0.1424(2) 0.0673(6) Uani 1 1 d . . .
C25 C 0.35575(13) 0.11492(11) 0.0356(2) 0.0686(6) Uani 1 1 d . . .
H25 H 0.4009 0.1105 -0.0256 0.082 Uiso 1 1 calc R . .
C26 C 0.27638(14) 0.07491(11) 0.0165(2) 0.0689(6) Uani 1 1 d . . .
C27 C 0.21007(14) 0.08147(11) 0.1100(2) 0.0735(6) Uani 1 1 d . . .
C28 C 0.22263(14) 0.12795(12) 0.2157(2) 0.0742(6) Uani 1 1 d . . .
H28 H 0.1773 0.1326 0.2766 0.089 Uiso 1 1 calc R . .


_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
N1A C3A 1.334(6) . ?
N1A C1A 1.335(5) . ?
C1A C2A 1.386(6) . ?
C1A H1A 0.9300 . ?
C2A C5A 1.370(6) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.386(6) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.374(5) . ?
C4A H4A 0.9300 . ?
C5A N3A 1.432(5) . ?
N3A N4A 1.226(4) . ?
N4A C6A 1.427(5) . ?
C6A C9A 1.365(7) . ?
C6A C7A 1.371(6) . ?
C7A C8A 1.388(6) . ?
C7A H7A 0.9300 . ?
C8A C11A 1.359(8) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.386(6) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.356(8) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9300 . ?
N1B C3B 1.334(8) . ?
N1B C1B 1.337(8) . ?
C1B C2B 1.381(8) . ?
C1B H1B 0.9300 . ?
C2B C5B 1.379(7) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.387(7) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.370(8) . ?
C4B H4B 0.9300 . ?
C5B N3B 1.430(6) . ?
N3B N4B 1.216(7) . ?
N4B C6B 1.424(6) . ?
C6B C7B 1.362(8) . ?
C6B C9B 1.373(8) . ?
C7B C8B 1.396(8) . ?
C7B H7B 0.9300 . ?
C8B C11B 1.356(10) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.377(8) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.362(10) . ?
C10B H10B 0.9300 . ?
C11B H11B 0.9300 . ?
N2 C14 1.319(3) . ?
N2 C12 1.324(3) . ?
N5 N6 1.233(2) . ?
N5 C16 1.432(3) . ?
N6 C17 1.426(3) . ?
C12 C13 1.370(3) . ?
C12 H12 0.9300 . ?
C13 C16 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C17 C20 1.354(3) . ?
C17 C18 1.359(3) . ?
C18 C19 1.397(4) . ?
C18 H18 0.9300 . ?
C19 C22 1.335(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.354(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
Cl1 C23 1.739(2) . ?
Cl2 C27 1.735(2) . ?
O1 C24 1.355(2) . ?
O1 H1O 0.8200 . ?
O2 C26 1.352(2) . ?
O2 H2O 0.8192 . ?
C23 C28 1.378(3) . ?
C23 C24 1.389(3) . ?
C24 C25 1.376(3) . ?
C25 C26 1.381(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.390(3) . ?
C27 C28 1.370(3) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3A N1A C1A 116.4(4) . . ?
N1A C1A C2A 124.1(4) . . ?
N1A C1A H1A 118.0 . . ?
C2A C1A H1A 118.0 . . ?
C5A C2A C1A 118.4(4) . . ?
C5A C2A H2A 120.8 . . ?
C1A C2A H2A 120.8 . . ?
N1A C3A C4A 123.2(4) . . ?
N1A C3A H3A 118.4 . . ?
C4A C3A H3A 118.4 . . ?
C5A C4A C3A 119.2(5) . . ?
C5A C4A H4A 120.4 . . ?
C3A C4A H4A 120.4 . . ?
C2A C5A C4A 118.7(4) . . ?
C2A C5A N3A 122.7(5) . . ?
C4A C5A N3A 118.6(5) . . ?
N4A N3A C5A 113.8(4) . . ?
N3A N4A C6A 114.8(4) . . ?
C9A C6A C7A 118.9(4) . . ?
C9A C6A N4A 125.0(5) . . ?
C7A C6A N4A 115.9(6) . . ?
C6A C7A C8A 120.9(5) . . ?
C6A C7A H7A 119.5 . . ?
C8A C7A H7A 119.5 . . ?
C11A C8A C7A 119.4(5) . . ?
C11A C8A H8A 120.3 . . ?
C7A C8A H8A 120.3 . . ?
C6A C9A C10A 120.0(5) . . ?
C6A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C11A C10A C9A 120.6(5) . . ?
C11A C10A H10A 119.7 . . ?
C9A C10A H10A 119.7 . . ?
C10A C11A C8A 120.1(4) . . ?
C10A C11A H11A 119.9 . . ?
C8A C11A H11A 119.9 . . ?
C3B N1B C1B 116.1(6) . . ?
N1B C1B C2B 124.2(7) . . ?
N1B C1B H1B 117.9 . . ?
C2B C1B H1B 117.9 . . ?
C5B C2B C1B 118.4(6) . . ?
C5B C2B H2B 120.8 . . ?
C1B C2B H2B 120.8 . . ?
N1B C3B C4B 123.2(6) . . ?
N1B C3B H3B 118.4 . . ?
C4B C3B H3B 118.4 . . ?
C5B C4B C3B 119.5(6) . . ?
C5B C4B H4B 120.2 . . ?
C3B C4B H4B 120.2 . . ?
C4B C5B C2B 118.0(5) . . ?
C4B C5B N3B 121.2(7) . . ?
C2B C5B N3B 120.8(8) . . ?
N4B N3B C5B 115.8(7) . . ?
N3B N4B C6B 116.2(7) . . ?
C7B C6B C9B 118.8(6) . . ?
C7B C6B N4B 119.5(8) . . ?
C9B C6B N4B 121.4(8) . . ?
C6B C7B C8B 120.6(6) . . ?
C6B C7B H7B 119.7 . . ?
C8B C7B H7B 119.7 . . ?
C11B C8B C7B 119.5(7) . . ?
C11B C8B H8B 120.2 . . ?
C7B C8B H8B 120.2 . . ?
C6B C9B C10B 120.4(7) . . ?
C6B C9B H9B 119.8 . . ?
C10B C9B H9B 119.8 . . ?
C11B C10B C9B 120.2(7) . . ?
C11B C10B H10B 119.9 . . ?
C9B C10B H10B 119.9 . . ?
C8B C11B C10B 120.1(6) . . ?
C8B C11B H11B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C14 N2 C12 116.6(2) . . ?
N6 N5 C16 113.76(19) . . ?
N5 N6 C17 114.1(2) . . ?
N2 C12 C13 124.3(3) . . ?
N2 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C12 C13 C16 118.2(2) . . ?
C12 C13 H13 120.9 . . ?
C16 C13 H13 120.9 . . ?
N2 C14 C15 123.8(2) . . ?
N2 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C16 C15 C14 118.5(3) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C13 118.6(2) . . ?
C15 C16 N5 116.0(2) . . ?
C13 C16 N5 125.3(2) . . ?
C20 C17 C18 118.8(2) . . ?
C20 C17 N6 124.3(2) . . ?
C18 C17 N6 116.9(2) . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C22 C19 C18 120.1(3) . . ?
C22 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C17 C20 C21 120.6(3) . . ?
C17 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C19 C22 C21 119.8(3) . . ?
C19 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 O1 H1O 109.5 . . ?
C26 O2 H2O 109.5 . . ?
C28 C23 C24 120.1(2) . . ?
C28 C23 Cl1 120.62(16) . . ?
C24 C23 Cl1 119.24(17) . . ?
O1 C24 C25 122.50(18) . . ?
O1 C24 C23 119.0(2) . . ?
C25 C24 C23 118.48(19) . . ?
C24 C25 C26 122.16(19) . . ?
C24 C25 H25 118.9 . . ?
C26 C25 H25 118.9 . . ?
O2 C26 C25 122.89(18) . . ?
O2 C26 C27 118.87(19) . . ?
C25 C26 C27 118.2(2) . . ?
C28 C27 C26 120.4(2) . . ?
C28 C27 Cl2 119.98(16) . . ?
C26 C27 Cl2 119.61(18) . . ?
C27 C28 C23 120.55(19) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3A N1A C1A C2A 6(2) . . . . ?
N1A C1A C2A C5A -3(2) . . . . ?
C1A N1A C3A C4A -4(2) . . . . ?
N1A C3A C4A C5A 0.1(18) . . . . ?
C1A C2A C5A C4A -1.1(16) . . . . ?
C1A C2A C5A N3A 177.1(11) . . . . ?
C3A C4A C5A C2A 2.5(14) . . . . ?
C3A C4A C5A N3A -175.8(9) . . . . ?
C2A C5A N3A N4A -10.0(11) . . . . ?
C4A C5A N3A N4A 168.3(7) . . . . ?
C5A N3A N4A C6A -176.3(6) . . . . ?
N3A N4A C6A C9A 6.8(10) . . . . ?
N3A N4A C6A C7A -177.3(7) . . . . ?
C9A C6A C7A C8A 2.0(13) . . . . ?
N4A C6A C7A C8A -174.1(8) . . . . ?
C6A C7A C8A C11A -3.0(19) . . . . ?
C7A C6A C9A C10A 1.4(12) . . . . ?
N4A C6A C9A C10A 177.2(7) . . . . ?
C6A C9A C10A C11A -4.0(19) . . . . ?
C9A C10A C11A C8A 3(3) . . . . ?
C7A C8A C11A C10A 1(3) . . . . ?
C3B N1B C1B C2B -5(5) . . . . ?
N1B C1B C2B C5B 8(4) . . . . ?
C1B N1B C3B C4B 3(5) . . . . ?
N1B C3B C4B C5B -3(4) . . . . ?
C3B C4B C5B C2B 5(3) . . . . ?
C3B C4B C5B N3B -176.4(18) . . . . ?
C1B C2B C5B C4B -7(3) . . . . ?
C1B C2B C5B N3B 174(2) . . . . ?
C4B C5B N3B N4B 9(2) . . . . ?
C2B C5B N3B N4B -172.6(18) . . . . ?
C5B N3B N4B C6B 174.8(13) . . . . ?
N3B N4B C6B C7B 2.4(19) . . . . ?
N3B N4B C6B C9B -171.5(14) . . . . ?
C9B C6B C7B C8B -4(3) . . . . ?
N4B C6B C7B C8B -178.0(15) . . . . ?
C6B C7B C8B C11B 6(4) . . . . ?
C7B C6B C9B C10B -2(3) . . . . ?
N4B C6B C9B C10B 172.1(14) . . . . ?
C6B C9B C10B C11B 6(4) . . . . ?
C7B C8B C11B C10B -2(7) . . . . ?
C9B C10B C11B C8B -3(7) . . . . ?
C16 N5 N6 C17 179.73(18) . . . . ?
C14 N2 C12 C13 -0.2(4) . . . . ?
N2 C12 C13 C16 0.4(4) . . . . ?
C12 N2 C14 C15 -0.2(4) . . . . ?
N2 C14 C15 C16 0.4(4) . . . . ?
C14 C15 C16 C13 -0.2(4) . . . . ?
C14 C15 C16 N5 179.8(2) . . . . ?
C12 C13 C16 C15 -0.1(4) . . . . ?
C12 C13 C16 N5 179.9(2) . . . . ?
N6 N5 C16 C15 -171.7(2) . . . . ?
N6 N5 C16 C13 8.3(3) . . . . ?
N5 N6 C17 C20 8.7(3) . . . . ?
N5 N6 C17 C18 -170.7(2) . . . . ?
C20 C17 C18 C19 -1.7(5) . . . . ?
N6 C17 C18 C19 177.8(3) . . . . ?
C17 C18 C19 C22 1.8(5) . . . . ?
C18 C17 C20 C21 0.6(4) . . . . ?
N6 C17 C20 C21 -178.8(3) . . . . ?
C17 C20 C21 C22 0.4(5) . . . . ?
C18 C19 C22 C21 -0.9(5) . . . . ?
C20 C21 C22 C19 -0.2(5) . . . . ?
C28 C23 C24 O1 -178.8(2) . . . . ?
Cl1 C23 C24 O1 2.0(3) . . . . ?
C28 C23 C24 C25 1.3(3) . . . . ?
Cl1 C23 C24 C25 -177.89(16) . . . . ?
O1 C24 C25 C26 179.4(2) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?
C24 C25 C26 O2 179.4(2) . . . . ?
C24 C25 C26 C27 -0.8(3) . . . . ?
O2 C26 C27 C28 -178.4(2) . . . . ?
C25 C26 C27 C28 1.8(3) . . . . ?
O2 C26 C27 Cl2 1.3(3) . . . . ?
C25 C26 C27 Cl2 -178.52(17) . . . . ?
C26 C27 C28 C23 -1.3(3) . . . . ?
Cl2 C27 C28 C23 179.06(17) . . . . ?
C24 C23 C28 C27 -0.3(3) . . . . ?
Cl1 C23 C28 C27 178.86(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.32
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.027
####################################################################### 
# 
# 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_dicl290
_database_code_depnum_ccdc_archive 'CCDC 1026675'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
 '4-pyridylazophenyl 4,6-dichloro-1,3-benzenediol'
;
_chemical_name_common            '4PAzP.4,6-diCl res 290'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Cl2 O2, 2(C11 H9 N3)'
_chemical_formula_sum            'C28 H22 Cl2 N6 O2'
_chemical_formula_weight         545.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.400(6)
_cell_length_b                   19.510(8)
_cell_length_c                   9.757(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.784(15)
_cell_angle_gamma                90.00
_cell_volume                     2727.2(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    9612
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14997
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4817
_reflns_number_gt                2665
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0615P)²+0.3788P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4817
_refine_ls_number_parameters     470
_refine_ls_number_restraints     457
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002

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
N1A N 1.4182(7) 0.1649(8) 0.0039(14) 0.101(3) Uani 0.609(7) 1 d PDU A 1
C1A C 1.3397(8) 0.1289(7) -0.0223(12) 0.113(3) Uani 0.609(7) 1 d PDU A 1
H1A H 1.3351 0.0998 -0.0982 0.136 Uiso 0.609(7) 1 calc PR A 1
C2A C 1.2648(6) 0.1318(6) 0.0552(10) 0.102(2) Uani 0.609(7) 1 d PDU A 1
H2A H 1.2116 0.1056 0.0315 0.123 Uiso 0.609(7) 1 calc PR A 1
C3A C 1.4232(6) 0.2033(6) 0.1162(13) 0.101(2) Uani 0.609(7) 1 d PDU A 1
H3A H 1.4781 0.2274 0.1402 0.121 Uiso 0.609(7) 1 calc PR A 1
C4A C 1.3516(6) 0.2098(6) 0.2003(11) 0.097(2) Uani 0.609(7) 1 d PDU A 1
H4A H 1.3585 0.2379 0.2776 0.116 Uiso 0.609(7) 1 calc PR A 1
C5A C 1.2703(4) 0.1740(5) 0.1673(8) 0.079(2) Uani 0.609(7) 1 d PDU A 1
N3A N 1.1945(3) 0.1832(3) 0.2492(5) 0.0974(16) Uani 0.609(7) 1 d PDU A 1
N4A N 1.1211(3) 0.1583(3) 0.2000(6) 0.0987(18) Uani 0.609(7) 1 d PDU A 1
C6A C 1.0421(4) 0.1709(4) 0.2745(8) 0.088(2) Uani 0.609(7) 1 d PDU A 1
C7A C 0.9596(5) 0.1426(5) 0.2220(10) 0.120(3) Uani 0.609(7) 1 d PDU A 1
H7A H 0.9580 0.1138 0.1458 0.144 Uiso 0.609(7) 1 calc PR A 1
C8A C 0.8782(5) 0.1563(5) 0.2809(12) 0.133(3) Uani 0.609(7) 1 d PDU A 1
H8A H 0.8217 0.1383 0.2425 0.160 Uiso 0.609(7) 1 calc PR A 1
C9A C 1.0448(5) 0.2114(5) 0.3879(10) 0.119(3) Uani 0.609(7) 1 d PDU A 1
H9A H 1.1006 0.2318 0.4231 0.143 Uiso 0.609(7) 1 calc PR A 1
C10A C 0.9634(6) 0.2224(6) 0.4516(10) 0.137(3) Uani 0.609(7) 1 d PDU A 1
H10A H 0.9654 0.2477 0.5327 0.165 Uiso 0.609(7) 1 calc PR A 1
C11A C 0.8816(7) 0.1961(10) 0.395(2) 0.132(3) Uani 0.609(7) 1 d PDU A 1
H11A H 0.8269 0.2054 0.4346 0.159 Uiso 0.609(7) 1 calc PR A 1
N1B N 1.4206(11) 0.1797(12) 0.020(2) 0.095(3) Uani 0.391(7) 1 d PDU A 2
C1B C 1.3539(12) 0.1388(10) -0.0388(17) 0.111(4) Uani 0.391(7) 1 d PDU A 2
H1B H 1.3654 0.1163 -0.1194 0.133 Uiso 0.391(7) 1 calc PR A 2
C2B C 1.2693(9) 0.1275(9) 0.0110(15) 0.105(3) Uani 0.391(7) 1 d PDU A 2
H2B H 1.2255 0.0983 -0.0348 0.126 Uiso 0.391(7) 1 calc PR A 2
C3B C 1.4009(9) 0.2108(10) 0.134(2) 0.100(3) Uani 0.391(7) 1 d PDU A 2
H3B H 1.4447 0.2412 0.1763 0.120 Uiso 0.391(7) 1 calc PR A 2
C4B C 1.3187(9) 0.2007(8) 0.1951(14) 0.092(3) Uani 0.391(7) 1 d PDU A 2
H4B H 1.3101 0.2214 0.2789 0.111 Uiso 0.391(7) 1 calc PR A 2
C5B C 1.2508(7) 0.1602(9) 0.1301(15) 0.086(3) Uani 0.391(7) 1 d PDU A 2
N3B N 1.1610(5) 0.1541(5) 0.1782(9) 0.099(3) Uani 0.391(7) 1 d PDU A 2
N4B N 1.1460(5) 0.1911(4) 0.2727(7) 0.096(2) Uani 0.391(7) 1 d PDU A 2
C6B C 1.0535(5) 0.1889(6) 0.3147(10) 0.087(3) Uani 0.391(7) 1 d PDU A 2
C7B C 0.9914(8) 0.1418(6) 0.2613(14) 0.108(3) Uani 0.391(7) 1 d PDU A 2
H7B H 1.0090 0.1101 0.1978 0.130 Uiso 0.391(7) 1 calc PR A 2
C8B C 0.9011(7) 0.1405(8) 0.3007(19) 0.127(4) Uani 0.391(7) 1 d PDU A 2
H8B H 0.8594 0.1066 0.2672 0.153 Uiso 0.391(7) 1 calc PR A 2
C9B C 1.0276(8) 0.2357(8) 0.4084(15) 0.120(4) Uani 0.391(7) 1 d PDU A 2
H9B H 1.0712 0.2661 0.4507 0.144 Uiso 0.391(7) 1 calc PR A 2
C10B C 0.9356(9) 0.2375(9) 0.4398(16) 0.126(4) Uani 0.391(7) 1 d PDU A 2
H10B H 0.9159 0.2719 0.4962 0.151 Uiso 0.391(7) 1 calc PR A 2
C11B C 0.8748(10) 0.1887(16) 0.388(3) 0.133(4) Uani 0.391(7) 1 d PDU A 2
H11B H 0.8141 0.1886 0.4127 0.160 Uiso 0.391(7) 1 calc PR A 2
N2 N 0.59369(16) 0.04006(15) 0.2505(3) 0.1099(7) Uani 1 1 d . . .
N5 N 0.36916(15) 0.08699(11) 0.4765(2) 0.0996(6) Uani 1 1 d . . .
N6 N 0.30238(15) 0.04762(11) 0.4637(2) 0.0987(6) Uani 1 1 d . . .
C12 C 0.5149(2) 0.00537(17) 0.2291(3) 0.1159(9) Uani 1 1 d . . .
H12 H 0.5114 -0.0292 0.1631 0.139 Uiso 1 1 calc R . .
C13 C 0.43797(18) 0.01705(15) 0.2981(3) 0.1047(8) Uani 1 1 d . . .
H13 H 0.3839 -0.0088 0.2792 0.126 Uiso 1 1 calc R . .
C14 C 0.5971(2) 0.08827(18) 0.3446(4) 0.1225(10) Uani 1 1 d . . .
H14 H 0.6522 0.1131 0.3617 0.147 Uiso 1 1 calc R . .
C15 C 0.52409(19) 0.10421(15) 0.4195(3) 0.1149(9) Uani 1 1 d . . .
H15 H 0.5297 0.1390 0.4851 0.138 Uiso 1 1 calc R . .
C16 C 0.44290(16) 0.06773(14) 0.3952(3) 0.0911(7) Uani 1 1 d . . .
C17 C 0.22879(17) 0.06600(15) 0.5445(3) 0.0927(7) Uani 1 1 d . . .
C18 C 0.1591(2) 0.01986(18) 0.5511(4) 0.1466(12) Uani 1 1 d . . .
H18 H 0.1600 -0.0210 0.5020 0.176 Uiso 1 1 calc R . .
C19 C 0.0860(2) 0.0331(2) 0.6312(5) 0.1567(14) Uani 1 1 d . . .
H19 H 0.0393 0.0006 0.6375 0.188 Uiso 1 1 calc R . .
C20 C 0.2239(2) 0.12559(18) 0.6130(3) 0.1298(10) Uani 1 1 d . . .
H20 H 0.2703 0.1584 0.6077 0.156 Uiso 1 1 calc R . .
C21 C 0.1512(3) 0.1387(2) 0.6906(4) 0.1572(14) Uani 1 1 d . . .
H21 H 0.1491 0.1799 0.7380 0.189 Uiso 1 1 calc R . .
C22 C 0.0830(2) 0.0920(2) 0.6983(4) 0.1342(11) Uani 1 1 d . . .
H22 H 0.0339 0.1011 0.7506 0.161 Uiso 1 1 calc R . .
Cl1 Cl 0.68188(5) 0.22758(4) 0.63458(8) 0.1184(3) Uani 1 1 d . . .
Cl2 Cl 0.88796(5) 0.03163(4) 0.90802(10) 0.1409(4) Uani 1 1 d . . .
O1 O 0.55052(11) 0.20021(10) 0.83640(18) 0.1138(6) Uani 1 1 d . . .
H1O H 0.5152 0.1906 0.8944 0.171 Uiso 1 1 d R . .
O2 O 0.73780(11) 0.03076(9) 1.08712(19) 0.1112(6) Uani 1 1 d . . .
H2O H 0.6954 0.0334 1.1371 0.167 Uiso 1 1 d R . .
C23 C 0.69668(16) 0.16794(12) 0.7666(2) 0.0867(6) Uani 1 1 d . . .
C24 C 0.62870(15) 0.16130(13) 0.8568(2) 0.0859(6) Uani 1 1 d . . .
C25 C 0.64317(15) 0.11563(12) 0.9634(2) 0.0877(7) Uani 1 1 d . . .
H25 H 0.5983 0.1116 1.0250 0.105 Uiso 1 1 calc R . .
C26 C 0.72211(16) 0.07560(13) 0.9821(3) 0.0878(7) Uani 1 1 d . . .
C27 C 0.78875(15) 0.08204(13) 0.8894(3) 0.0923(7) Uani 1 1 d . . .
C28 C 0.77615(16) 0.12818(13) 0.7840(3) 0.0949(7) Uani 1 1 d . . .
H28 H 0.8216 0.1328 0.7234 0.114 Uiso 1 1 calc R . .


_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
N1A C3A 1.322(6) . ?
N1A C1A 1.334(6) . ?
C1A C2A 1.379(6) . ?
C1A H1A 0.9300 . ?
C2A C5A 1.364(7) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.387(7) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.373(6) . ?
C4A H4A 0.9300 . ?
C5A N3A 1.428(5) . ?
N3A N4A 1.216(5) . ?
N4A C6A 1.432(6) . ?
C6A C9A 1.357(8) . ?
C6A C7A 1.362(7) . ?
C7A C8A 1.382(7) . ?
C7A H7A 0.9300 . ?
C8A C11A 1.353(8) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.398(7) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.351(8) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9300 . ?
N1B C3B 1.323(8) . ?
N1B C1B 1.334(7) . ?
C1B C2B 1.374(8) . ?
C1B H1B 0.9300 . ?
C2B C5B 1.375(8) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.391(8) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.363(8) . ?
C4B H4B 0.9300 . ?
C5B N3B 1.425(7) . ?
N3B N4B 1.208(7) . ?
N4B C6B 1.432(6) . ?
C6B C7B 1.349(8) . ?
C6B C9B 1.371(8) . ?
C7B C8B 1.393(8) . ?
C7B H7B 0.9300 . ?
C8B C11B 1.348(9) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.390(9) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.356(9) . ?
C10B H10B 0.9300 . ?
C11B H11B 0.9300 . ?
N2 C14 1.312(4) . ?
N2 C12 1.319(3) . ?
N5 N6 1.227(3) . ?
N5 C16 1.438(3) . ?
N6 C17 1.429(3) . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C13 C16 1.367(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(3) . ?
C15 H15 0.9300 . ?
C17 C20 1.346(4) . ?
C17 C18 1.354(4) . ?
C18 C19 1.398(5) . ?
C18 H18 0.9300 . ?
C19 C22 1.325(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.346(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
Cl1 C23 1.733(2) . ?
Cl2 C27 1.729(2) . ?
O1 C24 1.356(3) . ?
O1 H1O 0.8195 . ?
O2 C26 1.349(3) . ?
O2 H2O 0.8203 . ?
C23 C28 1.379(3) . ?
C23 C24 1.387(3) . ?
C24 C25 1.370(3) . ?
C25 C26 1.376(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.389(3) . ?
C27 C28 1.365(3) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3A N1A C1A 115.5(5) . . ?
N1A C1A C2A 124.5(5) . . ?
N1A C1A H1A 117.7 . . ?
C2A C1A H1A 117.7 . . ?
C5A C2A C1A 118.6(5) . . ?
C5A C2A H2A 120.7 . . ?
C1A C2A H2A 120.7 . . ?
N1A C3A C4A 124.1(5) . . ?
N1A C3A H3A 118.0 . . ?
C4A C3A H3A 117.9 . . ?
C5A C4A C3A 118.8(5) . . ?
C5A C4A H4A 120.6 . . ?
C3A C4A H4A 120.6 . . ?
C2A C5A C4A 118.3(5) . . ?
C2A C5A N3A 122.6(6) . . ?
C4A C5A N3A 119.1(6) . . ?
N4A N3A C5A 114.3(5) . . ?
N3A N4A C6A 115.7(5) . . ?
C9A C6A C7A 119.7(5) . . ?
C9A C6A N4A 123.7(6) . . ?
C7A C6A N4A 116.5(6) . . ?
C6A C7A C8A 120.6(5) . . ?
C6A C7A H7A 119.7 . . ?
C8A C7A H7A 119.7 . . ?
C11A C8A C7A 119.4(5) . . ?
C11A C8A H8A 120.3 . . ?
C7A C8A H8A 120.3 . . ?
C6A C9A C10A 119.7(5) . . ?
C6A C9A H9A 120.2 . . ?
C10A C9A H9A 120.2 . . ?
C11A C10A C9A 119.7(6) . . ?
C11A C10A H10A 120.1 . . ?
C9A C10A H10A 120.2 . . ?
C8A C11A C10A 120.8(5) . . ?
C8A C11A H11A 119.6 . . ?
C10A C11A H11A 119.6 . . ?
C3B N1B C1B 115.5(6) . . ?
N1B C1B C2B 124.7(6) . . ?
N1B C1B H1B 117.7 . . ?
C2B C1B H1B 117.7 . . ?
C1B C2B C5B 118.6(6) . . ?
C1B C2B H2B 120.7 . . ?
C5B C2B H2B 120.7 . . ?
N1B C3B C4B 123.9(6) . . ?
N1B C3B H3B 118.0 . . ?
C4B C3B H3B 118.0 . . ?
C5B C4B C3B 119.0(6) . . ?
C5B C4B H4B 120.5 . . ?
C3B C4B H4B 120.5 . . ?
C4B C5B C2B 118.2(5) . . ?
C4B C5B N3B 121.8(8) . . ?
C2B C5B N3B 119.9(8) . . ?
N4B N3B C5B 116.1(7) . . ?
N3B N4B C6B 116.3(7) . . ?
C7B C6B C9B 119.7(6) . . ?
C7B C6B N4B 120.6(8) . . ?
C9B C6B N4B 119.6(8) . . ?
C6B C7B C8B 120.5(6) . . ?
C6B C7B H7B 119.8 . . ?
C8B C7B H7B 119.7 . . ?
C11B C8B C7B 119.4(7) . . ?
C11B C8B H8B 120.3 . . ?
C7B C8B H8B 120.3 . . ?
C6B C9B C10B 119.6(7) . . ?
C6B C9B H9B 120.2 . . ?
C10B C9B H9B 120.2 . . ?
C11B C10B C9B 119.6(7) . . ?
C11B C10B H10B 120.2 . . ?
C9B C10B H10B 120.2 . . ?
C8B C11B C10B 120.9(6) . . ?
C8B C11B H11B 119.6 . . ?
C10B C11B H11B 119.6 . . ?
C14 N2 C12 116.7(2) . . ?
N6 N5 C16 113.3(2) . . ?
N5 N6 C17 113.8(2) . . ?
N2 C12 C13 124.1(3) . . ?
N2 C12 H12 117.9 . . ?
C13 C12 H12 117.9 . . ?
C16 C13 C12 118.2(3) . . ?
C16 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
N2 C14 C15 123.8(3) . . ?
N2 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C13 C16 C15 118.7(2) . . ?
C13 C16 N5 125.6(2) . . ?
C15 C16 N5 115.7(3) . . ?
C20 C17 C18 118.3(3) . . ?
C20 C17 N6 124.7(2) . . ?
C18 C17 N6 117.0(3) . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C22 C19 C18 120.0(3) . . ?
C22 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C17 C20 C21 120.9(3) . . ?
C17 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C19 C22 C21 120.0(3) . . ?
C19 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 O1 H1O 109.5 . . ?
C26 O2 H2O 109.5 . . ?
C28 C23 C24 120.0(2) . . ?
C28 C23 Cl1 120.52(18) . . ?
C24 C23 Cl1 119.51(19) . . ?
O1 C24 C25 122.42(19) . . ?
O1 C24 C23 118.9(2) . . ?
C25 C24 C23 118.7(2) . . ?
C24 C25 C26 122.0(2) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
O2 C26 C25 122.8(2) . . ?
O2 C26 C27 118.7(2) . . ?
C25 C26 C27 118.5(2) . . ?
C28 C27 C26 120.1(2) . . ?
C28 C27 Cl2 120.00(17) . . ?
C26 C27 Cl2 119.9(2) . . ?
C27 C28 C23 120.6(2) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3A N1A C1A C2A 2.9(12) . . . . ?
N1A C1A C2A C5A -0.4(10) . . . . ?
C1A N1A C3A C4A -3.1(18) . . . . ?
N1A C3A C4A C5A 1(2) . . . . ?
C1A C2A C5A C4A -2.1(14) . . . . ?
C1A C2A C5A N3A 176.5(9) . . . . ?
C3A C4A C5A C2A 1.9(17) . . . . ?
C3A C4A C5A N3A -176.7(10) . . . . ?
C2A C5A N3A N4A -9.9(12) . . . . ?
C4A C5A N3A N4A 168.8(9) . . . . ?
C5A N3A N4A C6A -175.6(6) . . . . ?
N3A N4A C6A C9A 4.2(10) . . . . ?
N3A N4A C6A C7A -179.1(7) . . . . ?
C9A C6A C7A C8A 1.8(12) . . . . ?
N4A C6A C7A C8A -175.0(8) . . . . ?
C6A C7A C8A C11A -2.5(17) . . . . ?
C7A C6A C9A C10A 1.5(13) . . . . ?
N4A C6A C9A C10A 178.1(8) . . . . ?
C6A C9A C10A C11A -4.1(19) . . . . ?
C7A C8A C11A C10A 0(3) . . . . ?
C9A C10A C11A C8A 3(3) . . . . ?
C3B N1B C1B C2B -0.2(18) . . . . ?
N1B C1B C2B C5B 0.0(14) . . . . ?
C1B N1B C3B C4B 3(3) . . . . ?
N1B C3B C4B C5B -5(3) . . . . ?
C3B C4B C5B C2B 4(3) . . . . ?
C3B C4B C5B N3B -172.6(17) . . . . ?
C1B C2B C5B C4B -2(2) . . . . ?
C1B C2B C5B N3B 174.8(14) . . . . ?
C4B C5B N3B N4B 6(2) . . . . ?
C2B C5B N3B N4B -170.8(15) . . . . ?
C5B N3B N4B C6B 175.5(11) . . . . ?
N3B N4B C6B C7B 7.7(13) . . . . ?
N3B N4B C6B C9B -171.4(12) . . . . ?
C9B C6B C7B C8B 0.0(18) . . . . ?
N4B C6B C7B C8B -179.0(11) . . . . ?
C6B C7B C8B C11B 3(3) . . . . ?
C7B C6B C9B C10B -5(2) . . . . ?
N4B C6B C9B C10B 174.3(12) . . . . ?
C6B C9B C10B C11B 6(3) . . . . ?
C7B C8B C11B C10B -1(4) . . . . ?
C9B C10B C11B C8B -3(4) . . . . ?
C16 N5 N6 C17 179.70(19) . . . . ?
C14 N2 C12 C13 0.4(4) . . . . ?
N2 C12 C13 C16 -0.1(4) . . . . ?
C12 N2 C14 C15 -0.5(5) . . . . ?
N2 C14 C15 C16 0.2(5) . . . . ?
C12 C13 C16 C15 -0.2(4) . . . . ?
C12 C13 C16 N5 179.8(2) . . . . ?
C14 C15 C16 C13 0.1(4) . . . . ?
C14 C15 C16 N5 -179.8(2) . . . . ?
N6 N5 C16 C13 8.6(4) . . . . ?
N6 N5 C16 C15 -171.5(2) . . . . ?
N5 N6 C17 C20 9.7(4) . . . . ?
N5 N6 C17 C18 -170.7(3) . . . . ?
C20 C17 C18 C19 -2.2(5) . . . . ?
N6 C17 C18 C19 178.1(3) . . . . ?
C17 C18 C19 C22 1.9(6) . . . . ?
C18 C17 C20 C21 1.6(5) . . . . ?
N6 C17 C20 C21 -178.8(3) . . . . ?
C17 C20 C21 C22 -0.6(6) . . . . ?
C18 C19 C22 C21 -0.9(7) . . . . ?
C20 C21 C22 C19 0.2(6) . . . . ?
C28 C23 C24 O1 -179.0(2) . . . . ?
Cl1 C23 C24 O1 2.3(3) . . . . ?
C28 C23 C24 C25 1.0(4) . . . . ?
Cl1 C23 C24 C25 -177.69(18) . . . . ?
O1 C24 C25 C26 179.0(2) . . . . ?
C23 C24 C25 C26 -1.1(4) . . . . ?
C24 C25 C26 O2 179.5(2) . . . . ?
C24 C25 C26 C27 0.0(4) . . . . ?
O2 C26 C27 C28 -178.3(2) . . . . ?
C25 C26 C27 C28 1.2(4) . . . . ?
O2 C26 C27 Cl2 1.5(3) . . . . ?
C25 C26 C27 Cl2 -178.98(18) . . . . ?
C26 C27 C28 C23 -1.2(4) . . . . ?
Cl2 C27 C28 C23 178.95(19) . . . . ?
C24 C23 C28 C27 0.1(4) . . . . ?
Cl1 C23 C28 C27 178.80(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.025
####################################################################### 
# 
# 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_dii190
_database_code_depnum_ccdc_archive 'CCDC 1026676'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
 '4-pyridylazophenyl 4,6-diiodo-1,3-benzenediol'
;
_chemical_name_common            '4PAzP.4,6-diI res 190'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 I2 O2, 2(C11 H9 N3)'
_chemical_formula_sum            'C28 H22 I2 N6 O2'
_chemical_formula_weight         728.32

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'
I I -0.4742 1.8119 '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'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9820(9)
_cell_length_b                   12.5271(13)
_cell_length_c                   26.146(3)
_cell_angle_alpha                84.500(5)
_cell_angle_beta                 89.331(5)
_cell_angle_gamma                74.563(5)
_cell_volume                     2822.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416
_exptl_absorpt_coefficient_mu    2.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.628
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38115
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.50
_reflns_number_total             12926
_reflns_number_gt                10561
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0135P)²+3.1479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00075(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         12926
_refine_ls_number_parameters     1067
_refine_ls_number_restraints     1283
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0551
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.003

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
N1A N 0.3757(4) 0.4769(3) 0.93182(11) 0.0381(8) Uani 0.928(4) 1 d PDU A 1
C1A C 0.4269(4) 0.5674(3) 0.93422(13) 0.0398(8) Uani 0.928(4) 1 d PDU A 1
H1A H 0.4265 0.5963 0.9665 0.048 Uiso 0.928(4) 1 calc PR A 1
C2A C 0.4808(4) 0.6215(3) 0.89167(13) 0.0372(8) Uani 0.928(4) 1 d PDU A 1
H2A H 0.5174 0.6851 0.8949 0.045 Uiso 0.928(4) 1 calc PR A 1
C3A C 0.3770(5) 0.4380(3) 0.88587(14) 0.0429(8) Uani 0.928(4) 1 d PDU A 1
H3A H 0.3422 0.3733 0.8836 0.051 Uiso 0.928(4) 1 calc PR A 1
C4A C 0.4257(4) 0.4865(3) 0.84168(12) 0.0386(8) Uani 0.928(4) 1 d PDU A 1
H4A H 0.4227 0.4567 0.8098 0.046 Uiso 0.928(4) 1 calc PR A 1
C5A C 0.4793(4) 0.5795(3) 0.84474(11) 0.0324(7) Uani 0.928(4) 1 d PDU A 1
N5A N 0.5336(3) 0.6235(2) 0.79755(10) 0.0376(7) Uani 0.928(4) 1 d PDU A 1
N6A N 0.5736(3) 0.7099(2) 0.80126(10) 0.0335(6) Uani 0.928(4) 1 d PDU A 1
C6A C 0.6274(3) 0.7546(2) 0.75433(11) 0.0300(7) Uani 0.928(4) 1 d PDU A 1
C7A C 0.6852(4) 0.8463(3) 0.75803(12) 0.0336(7) Uani 0.928(4) 1 d PDU A 1
H7A H 0.6885 0.8744 0.7904 0.040 Uiso 0.928(4) 1 calc PR A 1
C8A C 0.7379(5) 0.8965(3) 0.71464(14) 0.0408(8) Uani 0.928(4) 1 d PDU A 1
H8A H 0.7779 0.9588 0.7171 0.049 Uiso 0.928(4) 1 calc PR A 1
C9A C 0.6235(4) 0.7124(3) 0.70720(13) 0.0367(7) Uani 0.928(4) 1 d PDU A 1
H9A H 0.5857 0.6491 0.7048 0.044 Uiso 0.928(4) 1 calc PR A 1
C10A C 0.6754(5) 0.7636(3) 0.66379(13) 0.0411(8) Uani 0.928(4) 1 d PDU A 1
H10A H 0.6720 0.7357 0.6314 0.049 Uiso 0.928(4) 1 calc PR A 1
C11A C 0.7322(5) 0.8554(3) 0.66746(13) 0.0418(9) Uani 0.928(4) 1 d PDU A 1
H11A H 0.7672 0.8902 0.6376 0.050 Uiso 0.928(4) 1 calc PR A 1
N1B N 0.364(5) 0.468(3) 0.9202(13) 0.036(3) Uani 0.072(4) 1 d PDU A 2
C1B C 0.387(5) 0.560(3) 0.9377(9) 0.038(3) Uani 0.072(4) 1 d PDU A 2
H1B H 0.3637 0.5717 0.9726 0.046 Uiso 0.072(4) 1 calc PR A 2
C2B C 0.443(5) 0.638(3) 0.9076(8) 0.036(3) Uani 0.072(4) 1 d PDU A 2
H2B H 0.4521 0.7042 0.9208 0.043 Uiso 0.072(4) 1 calc PR A 2
C3B C 0.390(6) 0.456(3) 0.8702(14) 0.036(3) Uani 0.072(4) 1 d PDU A 2
H3B H 0.3680 0.3944 0.8565 0.044 Uiso 0.072(4) 1 calc PR A 2
C4B C 0.448(5) 0.528(2) 0.8378(10) 0.033(3) Uani 0.072(4) 1 d PDU A 2
H4B H 0.4625 0.5168 0.8025 0.039 Uiso 0.072(4) 1 calc PR A 2
C5B C 0.483(4) 0.617(2) 0.8576(8) 0.034(3) Uani 0.072(4) 1 d PDU A 2
N5B N 0.525(4) 0.6958(19) 0.8201(8) 0.033(3) Uani 0.072(4) 1 d PDU A 2
N6B N 0.566(3) 0.6587(19) 0.7788(8) 0.033(3) Uani 0.072(4) 1 d PDU A 2
C6B C 0.623(3) 0.7314(19) 0.7428(8) 0.032(3) Uani 0.072(4) 1 d PDU A 2
C7B C 0.658(5) 0.821(3) 0.7627(10) 0.033(3) Uani 0.072(4) 1 d PDU A 2
H7B H 0.6413 0.8317 0.7980 0.039 Uiso 0.072(4) 1 calc PR A 2
C8B C 0.716(5) 0.895(3) 0.7312(15) 0.036(3) Uani 0.072(4) 1 d PDU A 2
H8B H 0.7408 0.9560 0.7449 0.043 Uiso 0.072(4) 1 calc PR A 2
C9B C 0.644(5) 0.717(3) 0.6908(8) 0.034(3) Uani 0.072(4) 1 d PDU A 2
H9B H 0.6201 0.6557 0.6771 0.041 Uiso 0.072(4) 1 calc PR A 2
C10B C 0.700(6) 0.792(4) 0.6593(10) 0.039(3) Uani 0.072(4) 1 d PDU A 2
H10B H 0.7137 0.7832 0.6238 0.046 Uiso 0.072(4) 1 calc PR A 2
C11B C 0.737(6) 0.881(3) 0.6794(14) 0.038(3) Uani 0.072(4) 1 d PDU A 2
H11B H 0.7765 0.9316 0.6576 0.045 Uiso 0.072(4) 1 calc PR A 2
N3A N 0.4564(4) 0.5285(2) 0.37310(13) 0.0366(8) Uani 0.900(4) 1 d PDU B 1
C23A C 0.5742(4) 0.4975(3) 0.34071(15) 0.0393(8) Uani 0.900(4) 1 d PDU B 1
H23A H 0.6279 0.4209 0.3423 0.047 Uiso 0.900(4) 1 calc PR B 1
C24A C 0.6216(4) 0.5704(3) 0.30532(13) 0.0366(8) Uani 0.900(4) 1 d PDU B 1
H24A H 0.7050 0.5444 0.2831 0.044 Uiso 0.900(4) 1 calc PR B 1
C25A C 0.3823(4) 0.6370(3) 0.37035(14) 0.0352(8) Uani 0.900(4) 1 d PDU B 1
H25A H 0.2976 0.6606 0.3925 0.042 Uiso 0.900(4) 1 calc PR B 1
C26A C 0.4240(4) 0.7164(3) 0.33651(13) 0.0339(7) Uani 0.900(4) 1 d PDU B 1
H26A H 0.3707 0.7929 0.3364 0.041 Uiso 0.900(4) 1 calc PR B 1
C27A C 0.5441(4) 0.6825(3) 0.30313(11) 0.0303(7) Uani 0.900(4) 1 d PDU B 1
N9A N 0.5788(3) 0.7694(2) 0.26886(10) 0.0339(6) Uani 0.900(4) 1 d PDU B 1
N10A N 0.6619(3) 0.7337(2) 0.23240(10) 0.0339(6) Uani 0.900(4) 1 d PDU B 1
C28A C 0.6946(4) 0.8182(3) 0.19711(12) 0.0299(7) Uani 0.900(4) 1 d PDU B 1
C29A C 0.8018(4) 0.7818(3) 0.15952(15) 0.0404(8) Uani 0.900(4) 1 d PDU B 1
H29A H 0.8497 0.7047 0.1586 0.048 Uiso 0.900(4) 1 calc PR B 1
C30A C 0.8385(5) 0.8594(4) 0.12326(15) 0.0488(9) Uani 0.900(4) 1 d PDU B 1
H30A H 0.9120 0.8351 0.0975 0.059 Uiso 0.900(4) 1 calc PR B 1
C31A C 0.6238(5) 0.9311(3) 0.19830(15) 0.0335(7) Uani 0.900(4) 1 d PDU B 1
H31A H 0.5495 0.9557 0.2237 0.040 Uiso 0.900(4) 1 calc PR B 1
C32A C 0.6621(5) 1.0078(3) 0.16228(14) 0.0391(8) Uani 0.900(4) 1 d PDU B 1
H32A H 0.6156 1.0851 0.1634 0.047 Uiso 0.900(4) 1 calc PR B 1
C33A C 0.7689(5) 0.9712(4) 0.12450(14) 0.0441(9) Uani 0.900(4) 1 d PDU B 1
H33A H 0.7938 1.0235 0.0994 0.053 Uiso 0.900(4) 1 calc PR B 1
N3B N 0.429(4) 0.558(2) 0.3789(10) 0.036(3) Uani 0.100(4) 1 d PDU B 2
C23B C 0.549(4) 0.4904(16) 0.3571(9) 0.037(3) Uani 0.100(4) 1 d PDU B 2
H23B H 0.5804 0.4145 0.3704 0.045 Uiso 0.100(4) 1 calc PR B 2
C24B C 0.630(3) 0.5244(14) 0.3165(9) 0.036(3) Uani 0.100(4) 1 d PDU B 2
H24B H 0.7148 0.4733 0.3023 0.043 Uiso 0.100(4) 1 calc PR B 2
C25B C 0.390(3) 0.666(2) 0.3609(12) 0.035(3) Uani 0.100(4) 1 d PDU B 2
H25B H 0.3088 0.7160 0.3768 0.042 Uiso 0.100(4) 1 calc PR B 2
C26B C 0.465(3) 0.7072(15) 0.3198(10) 0.032(3) Uani 0.100(4) 1 d PDU B 2
H26B H 0.4342 0.7839 0.3077 0.038 Uiso 0.100(4) 1 calc PR B 2
C27B C 0.585(3) 0.6354(14) 0.2969(8) 0.031(3) Uani 0.100(4) 1 d PDU B 2
N9B N 0.652(2) 0.6832(13) 0.2530(7) 0.031(3) Uani 0.100(4) 1 d PDU B 2
N10B N 0.611(3) 0.7867(14) 0.2480(8) 0.034(3) Uani 0.100(4) 1 d PDU B 2
C28B C 0.674(2) 0.8376(13) 0.2052(6) 0.032(3) Uani 0.100(4) 1 d PDU B 2
C29B C 0.783(3) 0.7675(15) 0.1767(9) 0.035(3) Uani 0.100(4) 1 d PDU B 2
H29B H 0.8088 0.6893 0.1855 0.042 Uiso 0.100(4) 1 calc PR B 2
C30B C 0.853(3) 0.812(2) 0.1354(10) 0.042(3) Uani 0.100(4) 1 d PDU B 2
H30B H 0.9324 0.7647 0.1173 0.051 Uiso 0.100(4) 1 calc PR B 2
C31B C 0.636(5) 0.9523(13) 0.1919(13) 0.034(3) Uani 0.100(4) 1 d PDU B 2
H31B H 0.5669 1.0009 0.2126 0.041 Uiso 0.100(4) 1 calc PR B 2
C32B C 0.698(4) 0.9950(18) 0.1485(12) 0.036(3) Uani 0.100(4) 1 d PDU B 2
H32B H 0.6656 1.0723 0.1377 0.044 Uiso 0.100(4) 1 calc PR B 2
C33B C 0.808(4) 0.924(3) 0.1206(11) 0.041(3) Uani 0.100(4) 1 d PDU B 2
H33B H 0.8530 0.9540 0.0912 0.049 Uiso 0.100(4) 1 calc PR B 2
N4 N -0.0943(3) 0.4729(2) 0.43738(9) 0.0419(6) Uani 1 1 d . . .
N11 N -0.0068(3) 0.70239(19) 0.31996(9) 0.0352(5) Uani 1 1 d . . .
N12 N 0.0923(3) 0.66399(19) 0.28815(9) 0.0349(5) Uani 1 1 d . . .
C34 C 0.0102(3) 0.4383(3) 0.40193(13) 0.0486(8) Uani 1 1 d . . .
H34 H 0.0639 0.3616 0.4044 0.058 Uiso 1 1 calc R . .
C35 C 0.0454(3) 0.5072(2) 0.36174(12) 0.0427(7) Uani 1 1 d . . .
H35 H 0.1206 0.4787 0.3371 0.051 Uiso 1 1 calc R . .
C36 C -0.1671(4) 0.5801(3) 0.43355(12) 0.0520(9) Uani 1 1 d . . .
H36 H -0.2419 0.6062 0.4586 0.062 Uiso 1 1 calc R . .
C37 C -0.1404(4) 0.6566(3) 0.39511(12) 0.0479(8) Uani 1 1 d . . .
H37 H -0.1953 0.7329 0.3940 0.058 Uiso 1 1 calc R . .
C38 C -0.0325(3) 0.6193(2) 0.35855(10) 0.0330(6) Uani 1 1 d . . .
C39 C 0.1225(3) 0.7461(2) 0.25041(10) 0.0327(6) Uani 1 1 d . . .
C40 C 0.2324(3) 0.7050(3) 0.21416(11) 0.0428(7) Uani 1 1 d . . .
H40 H 0.2825 0.6277 0.2157 0.051 Uiso 1 1 calc R . .
C41 C 0.2681(4) 0.7783(3) 0.17570(12) 0.0539(9) Uani 1 1 d . . .
H41 H 0.3420 0.7512 0.1505 0.065 Uiso 1 1 calc R . .
C42 C 0.0503(4) 0.8596(2) 0.24889(11) 0.0393(7) Uani 1 1 d . . .
H42 H -0.0240 0.8874 0.2739 0.047 Uiso 1 1 calc R . .
C43 C 0.0884(4) 0.9311(3) 0.21048(12) 0.0488(8) Uani 1 1 d . . .
H43 H 0.0404 1.0087 0.2090 0.059 Uiso 1 1 calc R . .
C44 C 0.1963(4) 0.8898(3) 0.17413(12) 0.0547(9) Uani 1 1 d . . .
H44 H 0.2211 0.9396 0.1477 0.066 Uiso 1 1 calc R . .
N2A N -0.0668(9) 0.5420(6) 0.8649(2) 0.0461(13) Uani 0.708(5) 1 d PDU C 1
N7A N 0.1180(6) 0.7644(4) 0.76806(14) 0.0364(10) Uani 0.708(5) 1 d PDU C 1
N8A N 0.1388(4) 0.7436(3) 0.72248(14) 0.0361(9) Uani 0.708(5) 1 d PDU C 1
C12A C -0.0501(6) 0.5299(4) 0.8144(2) 0.0432(13) Uani 0.708(5) 1 d PDU C 1
H12A H -0.0809 0.4708 0.8014 0.052 Uiso 0.708(5) 1 calc PR C 1
C13A C 0.0098(5) 0.5994(4) 0.78042(19) 0.0378(11) Uani 0.708(5) 1 d PDU C 1
H13A H 0.0188 0.5881 0.7450 0.045 Uiso 0.708(5) 1 calc PR C 1
C14A C -0.0281(10) 0.6292(7) 0.8812(2) 0.0510(15) Uani 0.708(5) 1 d PDU C 1
H14A H -0.0474 0.6437 0.9160 0.061 Uiso 0.708(5) 1 calc PR C 1
C15A C 0.0386(9) 0.6997(5) 0.8503(2) 0.0481(13) Uani 0.708(5) 1 d PDU C 1
H15A H 0.0714 0.7570 0.8643 0.058 Uiso 0.708(5) 1 calc PR C 1
C16A C 0.0562(5) 0.6851(3) 0.79899(16) 0.0340(10) Uani 0.708(5) 1 d PDU C 1
C17A C 0.1978(11) 0.8232(7) 0.6913(2) 0.0333(11) Uani 0.708(5) 1 d PDU C 1
C18A C 0.2027(6) 0.8113(5) 0.6386(2) 0.0385(12) Uani 0.708(5) 1 d PDU C 1
H18A H 0.1666 0.7545 0.6254 0.046 Uiso 0.708(5) 1 calc PR C 1
C19A C 0.2613(6) 0.8841(5) 0.6060(2) 0.0390(13) Uani 0.708(5) 1 d PDU C 1
H19A H 0.2645 0.8775 0.5700 0.047 Uiso 0.708(5) 1 calc PR C 1
C20A C 0.2542(18) 0.9038(10) 0.7108(3) 0.0386(16) Uani 0.708(5) 1 d PDU C 1
H20A H 0.2568 0.9081 0.7468 0.046 Uiso 0.708(5) 1 calc PR C 1
C21A C 0.3070(10) 0.9786(6) 0.6774(2) 0.0435(13) Uani 0.708(5) 1 d PDU C 1
H21A H 0.3376 1.0381 0.6902 0.052 Uiso 0.708(5) 1 calc PR C 1
C22A C 0.3146(7) 0.9657(4) 0.62531(19) 0.0423(13) Uani 0.708(5) 1 d PDU C 1
H22A H 0.3571 1.0136 0.6027 0.051 Uiso 0.708(5) 1 calc PR C 1
N2B N -0.080(2) 0.5521(15) 0.8792(4) 0.043(3) Uani 0.292(5) 1 d PDU C 2
N7B N 0.0964(9) 0.6853(6) 0.7441(3) 0.0377(18) Uani 0.292(5) 1 d PDU C 2
N8B N 0.1319(15) 0.7735(8) 0.7482(3) 0.036(2) Uani 0.292(5) 1 d PDU C 2
C12B C 0.001(2) 0.6281(16) 0.8818(5) 0.045(2) Uani 0.292(5) 1 d PDU C 2
H12B H 0.0260 0.6453 0.9147 0.054 Uiso 0.292(5) 1 calc PR C 2
C13B C 0.0480(18) 0.6826(11) 0.8383(4) 0.042(2) Uani 0.292(5) 1 d PDU C 2
H13B H 0.0868 0.7454 0.8409 0.050 Uiso 0.292(5) 1 calc PR C 2
C14B C -0.0812(16) 0.5118(10) 0.8335(5) 0.045(3) Uani 0.292(5) 1 d PDU C 2
H14B H -0.1253 0.4513 0.8315 0.054 Uiso 0.292(5) 1 calc PR C 2
C15B C -0.0218(13) 0.5537(8) 0.7891(4) 0.037(2) Uani 0.292(5) 1 d PDU C 2
H15B H -0.0222 0.5209 0.7578 0.044 Uiso 0.292(5) 1 calc PR C 2
C16B C 0.0375(14) 0.6433(8) 0.7912(3) 0.033(2) Uani 0.292(5) 1 d PDU C 2
C17B C 0.186(3) 0.8213(16) 0.7021(5) 0.036(2) Uani 0.292(5) 1 d PDU C 2
C18B C 0.244(5) 0.913(2) 0.7084(6) 0.038(3) Uani 0.292(5) 1 d PDU C 2
H18B H 0.2384 0.9429 0.7405 0.045 Uiso 0.292(5) 1 calc PR C 2
C19B C 0.312(2) 0.9578(14) 0.6664(5) 0.044(3) Uani 0.292(5) 1 d PDU C 2
H19B H 0.3688 1.0099 0.6712 0.052 Uiso 0.292(5) 1 calc PR C 2
C20B C 0.1695(16) 0.7907(11) 0.6536(4) 0.040(3) Uani 0.292(5) 1 d PDU C 2
H20B H 0.1202 0.7339 0.6491 0.048 Uiso 0.292(5) 1 calc PR C 2
C21B C 0.2259(15) 0.8437(11) 0.6113(4) 0.043(3) Uani 0.292(5) 1 d PDU C 2
H21B H 0.2166 0.8221 0.5779 0.051 Uiso 0.292(5) 1 calc PR C 2
C22B C 0.2952(18) 0.9273(11) 0.6180(4) 0.042(3) Uani 0.292(5) 1 d PDU C 2
H22B H 0.3319 0.9641 0.5890 0.050 Uiso 0.292(5) 1 calc PR C 2
I1 I 0.62500(2) 0.906294(16) 0.931201(8) 0.04227(6) Uani 1 1 d . . .
I2 I 1.26987(2) 0.821521(17) 1.016877(8) 0.04448(6) Uani 1 1 d . . .
O1 O 0.6651(2) 0.67549(17) 0.99382(8) 0.0465(5) Uani 1 1 d . . .
H1O H 0.6660 0.6196 1.0131 0.070 Uiso 1 1 d R . .
O2 O 1.1790(2) 0.60319(18) 1.06307(9) 0.0558(6) Uani 1 1 d . . .
H2O H 1.1536 0.5510 1.0787 0.084 Uiso 1 1 d R . .
C45 C 0.8105(3) 0.8059(2) 0.97584(9) 0.0297(5) Uani 1 1 d . . .
C46 C 0.7973(3) 0.7045(2) 1.00016(10) 0.0313(6) Uani 1 1 d . . .
C47 C 0.9214(3) 0.6364(2) 1.02884(11) 0.0369(6) Uani 1 1 d . . .
H47 H 0.9133 0.5670 1.0450 0.044 Uiso 1 1 calc R . .
C48 C 1.0581(3) 0.6677(2) 1.03439(11) 0.0357(6) Uani 1 1 d . . .
C49 C 1.0696(3) 0.7691(2) 1.00947(10) 0.0297(6) Uani 1 1 d . . .
C50 C 0.9467(3) 0.8371(2) 0.98049(10) 0.0296(5) Uani 1 1 d . . .
H50 H 0.9555 0.9057 0.9636 0.036 Uiso 1 1 calc R . .
I3 I 0.72534(2) 0.836263(14) 0.510497(7) 0.03332(5) Uani 1 1 d . . .
I4 I 0.08425(2) 0.913759(16) 0.423142(8) 0.04286(6) Uani 1 1 d . . .
O3 O 0.6359(2) 0.61953(15) 0.55868(7) 0.0385(5) Uani 1 1 d . . .
H3O H 0.6086 0.5710 0.5767 0.058 Uiso 1 1 d R . .
O4 O 0.1269(2) 0.68091(18) 0.48641(8) 0.0464(5) Uani 1 1 d . . .
H4O H 0.1306 0.6234 0.5048 0.070 Uiso 1 1 d R . .
C51 C 0.5268(3) 0.7811(2) 0.50257(9) 0.0249(5) Uani 1 1 d . . .
C52 C 0.5155(3) 0.6809(2) 0.52878(9) 0.0272(5) Uani 1 1 d . . .
C53 C 0.3820(3) 0.6467(2) 0.52267(10) 0.0319(6) Uani 1 1 d . . .
H53 H 0.3754 0.5775 0.5394 0.038 Uiso 1 1 calc R . .
C54 C 0.2582(3) 0.7118(2) 0.49260(10) 0.0305(6) Uani 1 1 d . . .
C55 C 0.2711(3) 0.8123(2) 0.46705(9) 0.0271(5) Uani 1 1 d . . .
C56 C 0.4052(3) 0.8454(2) 0.47170(9) 0.0264(5) Uani 1 1 d . . .
H56 H 0.4140 0.9128 0.4535 0.032 Uiso 1 1 calc R . .


_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
N1A C3A 1.338(4) . ?
N1A C1A 1.339(4) . ?
C1A C2A 1.396(4) . ?
C1A H1A 0.9500 . ?
C2A C5A 1.382(4) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.375(5) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(4) . ?
C4A H4A 0.9500 . ?
C5A N5A 1.436(4) . ?
N5A N6A 1.239(3) . ?
N6A C6A 1.433(4) . ?
C6A C9A 1.391(4) . ?
C6A C7A 1.392(4) . ?
C7A C8A 1.384(4) . ?
C7A H7A 0.9500 . ?
C8A C11A 1.388(5) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.387(5) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.388(5) . ?
C10A H10A 0.9500 . ?
C11A H11A 0.9500 . ?
N1B C1B 1.338(9) . ?
N1B C3B 1.341(9) . ?
C1B C2B 1.395(9) . ?
C1B H1B 0.9500 . ?
C2B C5B 1.386(9) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.371(9) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.381(9) . ?
C4B H4B 0.9500 . ?
C5B N5B 1.443(9) . ?
N5B N6B 1.232(10) . ?
N6B C6B 1.432(8) . ?
C6B C7B 1.390(9) . ?
C6B C9B 1.392(9) . ?
C7B C8B 1.383(9) . ?
C7B H7B 0.9500 . ?
C8B C11B 1.387(9) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.386(9) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.387(9) . ?
C10B H10B 0.9500 . ?
C11B H11B 0.9500 . ?
N3A C25A 1.340(4) . ?
N3A C23A 1.345(4) . ?
C23A C24A 1.380(5) . ?
C23A H23A 0.9500 . ?
C24A C27A 1.388(4) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.391(4) . ?
C25A H25A 0.9500 . ?
C26A C27A 1.383(4) . ?
C26A H26A 0.9500 . ?
C27A N9A 1.439(4) . ?
N9A N10A 1.246(3) . ?
N10A C28A 1.425(4) . ?
C28A C29A 1.390(4) . ?
C28A C31A 1.392(4) . ?
C29A C30A 1.392(5) . ?
C29A H29A 0.9500 . ?
C30A C33A 1.376(5) . ?
C30A H30A 0.9500 . ?
C31A C32A 1.387(4) . ?
C31A H31A 0.9500 . ?
C32A C33A 1.392(5) . ?
C32A H32A 0.9500 . ?
C33A H33A 0.9500 . ?
N3B C25B 1.341(9) . ?
N3B C23B 1.343(9) . ?
C23B C24B 1.378(9) . ?
C23B H23B 0.9500 . ?
C24B C27B 1.389(9) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.391(9) . ?
C25B H25B 0.9500 . ?
C26B C27B 1.379(9) . ?
C26B H26B 0.9500 . ?
C27B N9B 1.442(8) . ?
N9B N10B 1.244(9) . ?
N10B C28B 1.425(8) . ?
C28B C29B 1.387(9) . ?
C28B C31B 1.394(8) . ?
C29B C30B 1.392(10) . ?
C29B H29B 0.9500 . ?
C30B C33B 1.376(10) . ?
C30B H30B 0.9500 . ?
C31B C32B 1.385(9) . ?
C31B H31B 0.9500 . ?
C32B C33B 1.391(10) . ?
C32B H32B 0.9500 . ?
C33B H33B 0.9500 . ?
N4 C36 1.323(4) . ?
N4 C34 1.329(4) . ?
N11 N12 1.243(3) . ?
N11 C38 1.441(3) . ?
N12 C39 1.433(3) . ?
C34 C35 1.383(4) . ?
C34 H34 0.9500 . ?
C35 C38 1.388(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.384(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.376(4) . ?
C37 H37 0.9500 . ?
C39 C40 1.392(4) . ?
C39 C42 1.394(4) . ?
C40 C41 1.389(4) . ?
C40 H40 0.9500 . ?
C41 C44 1.371(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.382(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.384(5) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
N2A C12A 1.345(8) . ?
N2A C14A 1.338(9) . ?
N7A N8A 1.246(5) . ?
N7A C16A 1.441(6) . ?
N8A C17A 1.433(5) . ?
C12A C13A 1.388(7) . ?
C12A H12A 0.9500 . ?
C13A C16A 1.380(6) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.387(7) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.373(6) . ?
C15A H15A 0.9500 . ?
C17A C20A 1.382(8) . ?
C17A C18A 1.398(8) . ?
C18A C19A 1.391(7) . ?
C18A H18A 0.9500 . ?
C19A C22A 1.377(7) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.391(7) . ?
C20A H20A 0.9500 . ?
C21A C22A 1.385(7) . ?
C21A H21A 0.9500 . ?
C22A H22A 0.9500 . ?
N2B C12B 1.346(11) . ?
N2B C14B 1.343(12) . ?
N7B N8B 1.242(8) . ?
N7B C16B 1.444(8) . ?
N8B C17B 1.429(8) . ?
C12B C13B 1.392(10) . ?
C12B H12B 0.9500 . ?
C13B C16B 1.381(9) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.389(9) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.370(8) . ?
C15B H15B 0.9500 . ?
C17B C20B 1.380(12) . ?
C17B C18B 1.405(12) . ?
C18B C19B 1.391(10) . ?
C18B H18B 0.9500 . ?
C19B C22B 1.378(10) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.395(9) . ?
C20B H20B 0.9500 . ?
C21B C22B 1.378(9) . ?
C21B H21B 0.9500 . ?
C22B H22B 0.9500 . ?
I1 C45 2.090(3) . ?
I2 C49 2.089(2) . ?
O1 C46 1.347(3) . ?
O1 H1O 0.8210 . ?
O2 C48 1.353(3) . ?
O2 H2O 0.8197 . ?
C45 C50 1.390(3) . ?
C45 C46 1.398(3) . ?
C46 C47 1.387(4) . ?
C47 C48 1.397(4) . ?
C47 H47 0.9500 . ?
C48 C49 1.400(4) . ?
C49 C50 1.383(4) . ?
C50 H50 0.9500 . ?
I3 C51 2.096(2) . ?
I4 C55 2.093(2) . ?
O3 C52 1.354(3) . ?
O3 H3O 0.8198 . ?
O4 C54 1.351(3) . ?
O4 H4O 0.8197 . ?
C51 C56 1.386(3) . ?
C51 C52 1.399(3) . ?
C52 C53 1.391(3) . ?
C53 C54 1.391(4) . ?
C53 H53 0.9500 . ?
C54 C55 1.399(3) . ?
C55 C56 1.385(3) . ?
C56 H56 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3A N1A C1A 117.2(3) . . ?
N1A C1A C2A 123.4(3) . . ?
N1A C1A H1A 118.3 . . ?
C2A C1A H1A 118.3 . . ?
C5A C2A C1A 117.8(3) . . ?
C5A C2A H2A 121.1 . . ?
C1A C2A H2A 121.1 . . ?
N1A C3A C4A 123.7(3) . . ?
N1A C3A H3A 118.1 . . ?
C4A C3A H3A 118.1 . . ?
C3A C4A C5A 118.5(3) . . ?
C3A C4A H4A 120.7 . . ?
C5A C4A H4A 120.7 . . ?
C2A C5A C4A 119.4(3) . . ?
C2A C5A N5A 124.9(3) . . ?
C4A C5A N5A 115.7(3) . . ?
N6A N5A C5A 113.8(3) . . ?
N5A N6A C6A 114.2(3) . . ?
C9A C6A C7A 120.3(3) . . ?
C9A C6A N6A 124.0(3) . . ?
C7A C6A N6A 115.7(3) . . ?
C8A C7A C6A 120.0(3) . . ?
C8A C7A H7A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C7A C8A C11A 119.8(3) . . ?
C7A C8A H8A 120.1 . . ?
C11A C8A H8A 120.1 . . ?
C10A C9A C6A 119.4(3) . . ?
C10A C9A H9A 120.3 . . ?
C6A C9A H9A 120.3 . . ?
C9A C10A C11A 120.3(3) . . ?
C9A C10A H10A 119.9 . . ?
C11A C10A H10A 119.9 . . ?
C8A C11A C10A 120.2(3) . . ?
C8A C11A H11A 119.9 . . ?
C10A C11A H11A 119.9 . . ?
C1B N1B C3B 116.9(8) . . ?
N1B C1B C2B 123.6(8) . . ?
N1B C1B H1B 118.2 . . ?
C2B C1B H1B 118.2 . . ?
C5B C2B C1B 117.5(7) . . ?
C5B C2B H2B 121.3 . . ?
C1B C2B H2B 121.3 . . ?
N1B C3B C4B 123.5(8) . . ?
N1B C3B H3B 118.2 . . ?
C4B C3B H3B 118.2 . . ?
C3B C4B C5B 118.8(8) . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B H4B 120.6 . . ?
C4B C5B C2B 119.0(8) . . ?
C4B C5B N5B 115.5(9) . . ?
C2B C5B N5B 123.6(10) . . ?
N6B N5B C5B 113.8(10) . . ?
N5B N6B C6B 115.0(10) . . ?
C7B C6B C9B 120.2(7) . . ?
C7B C6B N6B 115.8(8) . . ?
C9B C6B N6B 124.0(9) . . ?
C8B C7B C6B 120.2(7) . . ?
C8B C7B H7B 119.9 . . ?
C6B C7B H7B 119.9 . . ?
C7B C8B C11B 119.7(8) . . ?
C7B C8B H8B 120.2 . . ?
C11B C8B H8B 120.2 . . ?
C10B C9B C6B 119.3(7) . . ?
C10B C9B H9B 120.3 . . ?
C6B C9B H9B 120.3 . . ?
C9B C10B C11B 120.4(8) . . ?
C9B C10B H10B 119.8 . . ?
C11B C10B H10B 119.8 . . ?
C10B C11B C8B 120.2(7) . . ?
C10B C11B H11B 119.9 . . ?
C8B C11B H11B 119.9 . . ?
C25A N3A C23A 117.1(3) . . ?
N3A C23A C24A 124.0(3) . . ?
N3A C23A H23A 118.0 . . ?
C24A C23A H23A 118.0 . . ?
C23A C24A C27A 118.2(3) . . ?
C23A C24A H24A 120.9 . . ?
C27A C24A H24A 120.9 . . ?
N3A C25A C26A 122.8(3) . . ?
N3A C25A H25A 118.6 . . ?
C26A C25A H25A 118.6 . . ?
C27A C26A C25A 119.1(3) . . ?
C27A C26A H26A 120.5 . . ?
C25A C26A H26A 120.5 . . ?
C26A C27A C24A 118.8(3) . . ?
C26A C27A N9A 115.7(3) . . ?
C24A C27A N9A 125.5(3) . . ?
N10A N9A C27A 113.2(3) . . ?
N9A N10A C28A 114.3(3) . . ?
C29A C28A C31A 120.2(3) . . ?
C29A C28A N10A 116.1(3) . . ?
C31A C28A N10A 123.7(3) . . ?
C28A C29A C30A 119.5(3) . . ?
C28A C29A H29A 120.3 . . ?
C30A C29A H29A 120.3 . . ?
C33A C30A C29A 120.3(3) . . ?
C33A C30A H30A 119.8 . . ?
C29A C30A H30A 119.8 . . ?
C32A C31A C28A 119.9(3) . . ?
C32A C31A H31A 120.1 . . ?
C28A C31A H31A 120.1 . . ?
C31A C32A C33A 119.8(3) . . ?
C31A C32A H32A 120.1 . . ?
C33A C32A H32A 120.1 . . ?
C30A C33A C32A 120.3(3) . . ?
C30A C33A H33A 119.8 . . ?
C32A C33A H33A 119.8 . . ?
C25B N3B C23B 117.1(7) . . ?
N3B C23B C24B 124.1(8) . . ?
N3B C23B H23B 117.9 . . ?
C24B C23B H23B 117.9 . . ?
C23B C24B C27B 118.1(7) . . ?
C23B C24B H24B 121.0 . . ?
C27B C24B H24B 121.0 . . ?
N3B C25B C26B 122.6(8) . . ?
N3B C25B H25B 118.7 . . ?
C26B C25B H25B 118.7 . . ?
C27B C26B C25B 119.2(7) . . ?
C27B C26B H26B 120.4 . . ?
C25B C26B H26B 120.4 . . ?
C26B C27B C24B 118.8(7) . . ?
C26B C27B N9B 116.0(8) . . ?
C24B C27B N9B 125.2(9) . . ?
N10B N9B C27B 113.1(9) . . ?
N9B N10B C28B 115.1(9) . . ?
C29B C28B C31B 119.9(7) . . ?
C29B C28B N10B 116.7(8) . . ?
C31B C28B N10B 123.4(8) . . ?
C28B C29B C30B 119.7(7) . . ?
C28B C29B H29B 120.1 . . ?
C30B C29B H29B 120.1 . . ?
C33B C30B C29B 120.3(8) . . ?
C33B C30B H30B 119.9 . . ?
C29B C30B H30B 119.9 . . ?
C32B C31B C28B 119.8(7) . . ?
C32B C31B H31B 120.1 . . ?
C28B C31B H31B 120.1 . . ?
C31B C32B C33B 119.9(8) . . ?
C31B C32B H32B 120.0 . . ?
C33B C32B H32B 120.0 . . ?
C30B C33B C32B 120.1(8) . . ?
C30B C33B H33B 120.0 . . ?
C32B C33B H33B 120.0 . . ?
C36 N4 C34 117.1(3) . . ?
N12 N11 C38 113.4(2) . . ?
N11 N12 C39 114.1(2) . . ?
N4 C34 C35 124.0(3) . . ?
N4 C34 H34 118.0 . . ?
C35 C34 H34 118.0 . . ?
C34 C35 C38 117.8(3) . . ?
C34 C35 H35 121.1 . . ?
C38 C35 H35 121.1 . . ?
N4 C36 C37 123.8(3) . . ?
N4 C36 H36 118.1 . . ?
C37 C36 H36 118.1 . . ?
C38 C37 C36 118.4(3) . . ?
C38 C37 H37 120.8 . . ?
C36 C37 H37 120.8 . . ?
C37 C38 C35 118.9(3) . . ?
C37 C38 N11 116.3(3) . . ?
C35 C38 N11 124.8(3) . . ?
C40 C39 C42 120.8(3) . . ?
C40 C39 N12 115.2(3) . . ?
C42 C39 N12 124.1(2) . . ?
C41 C40 C39 119.2(3) . . ?
C41 C40 H40 120.4 . . ?
C39 C40 H40 120.4 . . ?
C44 C41 C40 119.9(3) . . ?
C44 C41 H41 120.1 . . ?
C40 C41 H41 120.1 . . ?
C43 C42 C39 119.0(3) . . ?
C43 C42 H42 120.5 . . ?
C39 C42 H42 120.5 . . ?
C42 C43 C44 120.1(3) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C41 C44 C43 121.0(3) . . ?
C41 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?
C12A N2A C14A 116.3(4) . . ?
N8A N7A C16A 113.6(4) . . ?
N7A N8A C17A 113.8(4) . . ?
N2A C12A C13A 123.4(5) . . ?
N2A C12A H12A 118.3 . . ?
C13A C12A H12A 118.3 . . ?
C16A C13A C12A 118.9(5) . . ?
C16A C13A H13A 120.6 . . ?
C12A C13A H13A 120.6 . . ?
N2A C14A C15A 123.9(6) . . ?
N2A C14A H14A 118.1 . . ?
C15A C14A H14A 118.1 . . ?
C16A C15A C14A 118.7(6) . . ?
C16A C15A H15A 120.6 . . ?
C14A C15A H15A 120.6 . . ?
C15A C16A C13A 118.7(4) . . ?
C15A C16A N7A 116.5(4) . . ?
C13A C16A N7A 124.8(4) . . ?
C20A C17A C18A 120.7(4) . . ?
C20A C17A N8A 123.9(5) . . ?
C18A C17A N8A 115.4(5) . . ?
C17A C18A C19A 118.8(5) . . ?
C17A C18A H18A 120.6 . . ?
C19A C18A H18A 120.6 . . ?
C22A C19A C18A 120.4(5) . . ?
C22A C19A H19A 119.8 . . ?
C18A C19A H19A 119.8 . . ?
C17A C20A C21A 119.8(6) . . ?
C17A C20A H20A 120.1 . . ?
C21A C20A H20A 120.1 . . ?
C20A C21A C22A 119.5(5) . . ?
C20A C21A H21A 120.2 . . ?
C22A C21A H21A 120.2 . . ?
C19A C22A C21A 120.6(4) . . ?
C19A C22A H22A 119.7 . . ?
C21A C22A H22A 119.7 . . ?
C12B N2B C14B 116.0(7) . . ?
N8B N7B C16B 112.6(6) . . ?
N7B N8B C17B 115.1(8) . . ?
N2B C12B C13B 122.7(8) . . ?
N2B C12B H12B 118.7 . . ?
C13B C12B H12B 118.7 . . ?
C16B C13B C12B 118.6(8) . . ?
C16B C13B H13B 120.7 . . ?
C12B C13B H13B 120.7 . . ?
N2B C14B C15B 123.6(9) . . ?
N2B C14B H14B 118.2 . . ?
C15B C14B H14B 118.2 . . ?
C16B C15B C14B 118.7(8) . . ?
C16B C15B H15B 120.7 . . ?
C14B C15B H15B 120.7 . . ?
C13B C16B C15B 118.8(6) . . ?
C13B C16B N7B 124.0(7) . . ?
C15B C16B N7B 117.0(7) . . ?
C20B C17B C18B 120.1(6) . . ?
C20B C17B N8B 124.7(9) . . ?
C18B C17B N8B 114.9(9) . . ?
C17B C18B C19B 118.5(9) . . ?
C17B C18B H18B 120.8 . . ?
C19B C18B H18B 120.7 . . ?
C22B C19B C18B 120.3(9) . . ?
C22B C19B H19B 119.9 . . ?
C18B C19B H19B 119.9 . . ?
C21B C20B C17B 119.7(9) . . ?
C21B C20B H20B 120.2 . . ?
C17B C20B H20B 120.2 . . ?
C22B C21B C20B 120.1(8) . . ?
C22B C21B H21B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C21B C22B C19B 120.3(7) . . ?
C21B C22B H22B 119.8 . . ?
C19B C22B H22B 119.8 . . ?
C46 O1 H1A 109.5 . . ?
C48 O2 H2 109.5 . . ?
C50 C45 C46 120.0(2) . . ?
C50 C45 I1 121.13(18) . . ?
C46 C45 I1 118.84(19) . . ?
O1 C46 C47 122.4(2) . . ?
O1 C46 C45 118.5(2) . . ?
C47 C46 C45 119.1(2) . . ?
C46 C47 C48 121.4(2) . . ?
C46 C47 H47 119.3 . . ?
C48 C47 H47 119.3 . . ?
O2 C48 C47 122.1(2) . . ?
O2 C48 C49 119.2(2) . . ?
C47 C48 C49 118.7(3) . . ?
C50 C49 C48 120.2(2) . . ?
C50 C49 I2 119.17(18) . . ?
C48 C49 I2 120.6(2) . . ?
C49 C50 C45 120.6(2) . . ?
C49 C50 H50 119.7 . . ?
C45 C50 H50 119.7 . . ?
C52 O3 H3 109.4 . . ?
C54 O4 H4A 109.6 . . ?
C56 C51 C52 119.9(2) . . ?
C56 C51 I3 119.59(17) . . ?
C52 C51 I3 120.48(18) . . ?
O3 C52 C53 122.2(2) . . ?
O3 C52 C51 118.8(2) . . ?
C53 C52 C51 119.0(2) . . ?
C54 C53 C52 121.5(2) . . ?
C54 C53 H53 119.3 . . ?
C52 C53 H53 119.3 . . ?
O4 C54 C53 122.6(2) . . ?
O4 C54 C55 118.7(2) . . ?
C53 C54 C55 118.7(2) . . ?
C56 C55 C54 120.2(2) . . ?
C56 C55 I4 120.26(18) . . ?
C54 C55 I4 119.51(18) . . ?
C55 C56 C51 120.6(2) . . ?
C55 C56 H56 119.7 . . ?
C51 C56 H56 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3A N1A C1A C2A -0.2(5) . . . . ?
N1A C1A C2A C5A 0.7(5) . . . . ?
C1A N1A C3A C4A -0.8(6) . . . . ?
N1A C3A C4A C5A 1.2(6) . . . . ?
C1A C2A C5A C4A -0.3(5) . . . . ?
C1A C2A C5A N5A -178.6(3) . . . . ?
C3A C4A C5A C2A -0.6(5) . . . . ?
C3A C4A C5A N5A 177.8(3) . . . . ?
C2A C5A N5A N6A -5.0(5) . . . . ?
C4A C5A N5A N6A 176.7(3) . . . . ?
C5A N5A N6A C6A -179.8(2) . . . . ?
N5A N6A C6A C9A 5.5(4) . . . . ?
N5A N6A C6A C7A -174.9(3) . . . . ?
C9A C6A C7A C8A 0.6(5) . . . . ?
N6A C6A C7A C8A -179.1(3) . . . . ?
C6A C7A C8A C11A 0.3(5) . . . . ?
C7A C6A C9A C10A -1.1(5) . . . . ?
N6A C6A C9A C10A 178.5(3) . . . . ?
C6A C9A C10A C11A 0.7(5) . . . . ?
C7A C8A C11A C10A -0.7(6) . . . . ?
C9A C10A C11A C8A 0.2(6) . . . . ?
C3B N1B C1B C2B -3(3) . . . . ?
N1B C1B C2B C5B -3.2(19) . . . . ?
C1B N1B C3B C4B 4(5) . . . . ?
N1B C3B C4B C5B 1(6) . . . . ?
C3B C4B C5B C2B -8(6) . . . . ?
C3B C4B C5B N5B -173(4) . . . . ?
C1B C2B C5B C4B 9(4) . . . . ?
C1B C2B C5B N5B 172(2) . . . . ?
C4B C5B N5B N6B -20(4) . . . . ?
C2B C5B N5B N6B 176(3) . . . . ?
C5B N5B N6B C6B -174(2) . . . . ?
N5B N6B C6B C7B 14(3) . . . . ?
N5B N6B C6B C9B -166(3) . . . . ?
C9B C6B C7B C8B -1(3) . . . . ?
N6B C6B C7B C8B 179(2) . . . . ?
C6B C7B C8B C11B 1(5) . . . . ?
C7B C6B C9B C10B 0(5) . . . . ?
N6B C6B C9B C10B -180(3) . . . . ?
C6B C9B C10B C11B 1(6) . . . . ?
C9B C10B C11B C8B -1(7) . . . . ?
C7B C8B C11B C10B 0(6) . . . . ?
C25A N3A C23A C24A -0.1(5) . . . . ?
N3A C23A C24A C27A 0.5(5) . . . . ?
C23A N3A C25A C26A -1.1(5) . . . . ?
N3A C25A C26A C27A 1.9(6) . . . . ?
C25A C26A C27A C24A -1.5(5) . . . . ?
C25A C26A C27A N9A 179.1(3) . . . . ?
C23A C24A C27A C26A 0.4(5) . . . . ?
C23A C24A C27A N9A 179.7(3) . . . . ?
C26A C27A N9A N10A -164.7(3) . . . . ?
C24A C27A N9A N10A 15.9(4) . . . . ?
C27A N9A N10A C28A 178.4(2) . . . . ?
N9A N10A C28A C29A 172.4(3) . . . . ?
N9A N10A C28A C31A -8.7(5) . . . . ?
C31A C28A C29A C30A 0.4(5) . . . . ?
N10A C28A C29A C30A 179.3(3) . . . . ?
C28A C29A C30A C33A -0.2(6) . . . . ?
C29A C28A C31A C32A -0.9(6) . . . . ?
N10A C28A C31A C32A -179.7(4) . . . . ?
C28A C31A C32A C33A 1.3(6) . . . . ?
C29A C30A C33A C32A 0.6(6) . . . . ?
C31A C32A C33A C30A -1.1(6) . . . . ?
C25B N3B C23B C24B -2(2) . . . . ?
N3B C23B C24B C27B 0.1(18) . . . . ?
C23B N3B C25B C26B 3(5) . . . . ?
N3B C25B C26B C27B -1(6) . . . . ?
C25B C26B C27B C24B -2(5) . . . . ?
C25B C26B C27B N9B 177(3) . . . . ?
C23B C24B C27B C26B 2(4) . . . . ?
C23B C24B C27B N9B -177(2) . . . . ?
C26B C27B N9B N10B 13(4) . . . . ?
C24B C27B N9B N10B -169(3) . . . . ?
C27B N9B N10B C28B 179.9(18) . . . . ?
N9B N10B C28B C29B -5(2) . . . . ?
N9B N10B C28B C31B 177(3) . . . . ?
C31B C28B C29B C30B 1(3) . . . . ?
N10B C28B C29B C30B -178(2) . . . . ?
C28B C29B C30B C33B -4(4) . . . . ?
C29B C28B C31B C32B 4(4) . . . . ?
N10B C28B C31B C32B -178(3) . . . . ?
C28B C31B C32B C33B -5(6) . . . . ?
C29B C30B C33B C32B 3(5) . . . . ?
C31B C32B C33B C30B 1(6) . . . . ?
C38 N11 N12 C39 -178.2(2) . . . . ?
C36 N4 C34 C35 -0.5(5) . . . . ?
N4 C34 C35 C38 0.4(5) . . . . ?
C34 N4 C36 C37 0.1(5) . . . . ?
N4 C36 C37 C38 0.2(5) . . . . ?
C36 C37 C38 C35 -0.3(5) . . . . ?
C36 C37 C38 N11 -178.8(3) . . . . ?
C34 C35 C38 C37 -0.1(4) . . . . ?
C34 C35 C38 N11 178.4(3) . . . . ?
N12 N11 C38 C37 179.7(3) . . . . ?
N12 N11 C38 C35 1.2(4) . . . . ?
N11 N12 C39 C40 -179.6(2) . . . . ?
N11 N12 C39 C42 0.6(4) . . . . ?
C42 C39 C40 C41 -1.0(4) . . . . ?
N12 C39 C40 C41 179.3(3) . . . . ?
C39 C40 C41 C44 0.7(5) . . . . ?
C40 C39 C42 C43 0.5(4) . . . . ?
N12 C39 C42 C43 -179.8(3) . . . . ?
C39 C42 C43 C44 0.2(5) . . . . ?
C40 C41 C44 C43 0.1(5) . . . . ?
C42 C43 C44 C41 -0.6(5) . . . . ?
C16A N7A N8A C17A 179.0(6) . . . . ?
C14A N2A C12A C13A 2.8(11) . . . . ?
N2A C12A C13A C16A 0.5(8) . . . . ?
C12A N2A C14A C15A -5.6(12) . . . . ?
N2A C14A C15A C16A 5.0(10) . . . . ?
C14A C15A C16A C13A -1.3(8) . . . . ?
C14A C15A C16A N7A 176.6(5) . . . . ?
C12A C13A C16A C15A -1.2(7) . . . . ?
C12A C13A C16A N7A -179.0(5) . . . . ?
N8A N7A C16A C15A 176.5(5) . . . . ?
N8A N7A C16A C13A -5.7(7) . . . . ?
N7A N8A C17A C20A 11.5(13) . . . . ?
N7A N8A C17A C18A -171.6(6) . . . . ?
C20A C17A C18A C19A -1.8(13) . . . . ?
N8A C17A C18A C19A -178.8(6) . . . . ?
C17A C18A C19A C22A 0.6(8) . . . . ?
C18A C17A C20A C21A 4(2) . . . . ?
N8A C17A C20A C21A -179.0(11) . . . . ?
C17A C20A C21A C22A -5.4(19) . . . . ?
C18A C19A C22A C21A -1.8(8) . . . . ?
C20A C21A C22A C19A 4.2(13) . . . . ?
C16B N7B N8B C17B -177.8(16) . . . . ?
C14B N2B C12B C13B 15(3) . . . . ?
N2B C12B C13B C16B -12.1(18) . . . . ?
C12B N2B C14B C15B -8(3) . . . . ?
N2B C14B C15B C16B -2(2) . . . . ?
C12B C13B C16B C15B 1.2(15) . . . . ?
C12B C13B C16B N7B -173.8(9) . . . . ?
C14B C15B C16B C13B 5(2) . . . . ?
C14B C15B C16B N7B -179.2(11) . . . . ?
N8B N7B C16B C13B -12.4(17) . . . . ?
N8B N7B C16B C15B 172.5(11) . . . . ?
N7B N8B C17B C20B 14(3) . . . . ?
N7B N8B C17B C18B -172(2) . . . . ?
C20B C17B C18B C19B -12(5) . . . . ?
N8B C17B C18B C19B 174(3) . . . . ?
C17B C18B C19B C22B 12(5) . . . . ?
C18B C17B C20B C21B 6(4) . . . . ?
N8B C17B C20B C21B 180(2) . . . . ?
C17B C20B C21B C22B -1(2) . . . . ?
C20B C21B C22B C19B 1(2) . . . . ?
C18B C19B C22B C21B -7(3) . . . . ?
C50 C45 C46 O1 -178.3(2) . . . . ?
I1 C45 C46 O1 0.0(3) . . . . ?
C50 C45 C46 C47 0.2(4) . . . . ?
I1 C45 C46 C47 178.5(2) . . . . ?
O1 C46 C47 C48 179.2(3) . . . . ?
C45 C46 C47 C48 0.8(4) . . . . ?
C46 C47 C48 O2 178.6(3) . . . . ?
C46 C47 C48 C49 -1.2(4) . . . . ?
O2 C48 C49 C50 -179.1(3) . . . . ?
C47 C48 C49 C50 0.7(4) . . . . ?
O2 C48 C49 I2 -0.6(4) . . . . ?
C47 C48 C49 I2 179.3(2) . . . . ?
C48 C49 C50 C45 0.2(4) . . . . ?
I2 C49 C50 C45 -178.40(19) . . . . ?
C46 C45 C50 C49 -0.6(4) . . . . ?
I1 C45 C50 C49 -178.95(19) . . . . ?
C56 C51 C52 O3 180.0(2) . . . . ?
I3 C51 C52 O3 -1.0(3) . . . . ?
C56 C51 C52 C53 0.9(4) . . . . ?
I3 C51 C52 C53 179.97(19) . . . . ?
O3 C52 C53 C54 178.7(2) . . . . ?
C51 C52 C53 C54 -2.2(4) . . . . ?
C52 C53 C54 O4 -179.4(3) . . . . ?
C52 C53 C54 C55 1.7(4) . . . . ?
O4 C54 C55 C56 -178.7(2) . . . . ?
C53 C54 C55 C56 0.2(4) . . . . ?
O4 C54 C55 I4 2.7(3) . . . . ?
C53 C54 C55 I4 -178.4(2) . . . . ?
C54 C55 C56 C51 -1.6(4) . . . . ?
I4 C55 C56 C51 177.05(18) . . . . ?
C52 C51 C56 C55 1.0(4) . . . . ?
I3 C51 C56 C55 -178.10(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_dii290
_database_code_depnum_ccdc_archive 'CCDC 1026677'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
 '4-pyridylazophenyl 4,6-diiodo-1,3-benzenediol'
;
_chemical_name_common            '4PAzP.4,6-diI res 290'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 I2 O2, 2(C11 H9 N3)'
_chemical_formula_sum            'C28 H22 I2 N6 O2'
_chemical_formula_weight         728.32

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'
I I -0.4742 1.8119 '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'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0480(9)
_cell_length_b                   12.5933(13)
_cell_length_c                   26.305(3)
_cell_angle_alpha                83.815(5)
_cell_angle_beta                 89.271(5)
_cell_angle_gamma                75.005(5)
_cell_volume                     2878.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    9855
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35

_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416
_exptl_absorpt_coefficient_mu    2.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19182
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.34
_reflns_number_total             10476
_reflns_number_gt                6582
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0307P)²+1.1241P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00138(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10476
_refine_ls_number_parameters     1067
_refine_ls_number_restraints     1329
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0684
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002

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
N1A N 1.3770(12) 0.4789(6) 0.9327(2) 0.0732(19) Uani 0.770(8) 1 d PDU A 1
C1A C 1.3770(10) 0.4394(6) 0.8875(3) 0.083(2) Uani 0.770(8) 1 d PDU A 1
H1A H 1.3423 0.3765 0.8858 0.100 Uiso 0.770(8) 1 calc PR A 1
C2A C 1.4267(9) 0.4882(6) 0.8430(3) 0.077(2) Uani 0.770(8) 1 d PDU A 1
H2A H 1.4250 0.4586 0.8122 0.093 Uiso 0.770(8) 1 calc PR A 1
C3A C 1.4298(10) 0.5674(7) 0.9341(3) 0.075(2) Uani 0.770(8) 1 d PDU A 1
H3A H 1.4337 0.5949 0.9653 0.090 Uiso 0.770(8) 1 calc PR A 1
C4A C 1.4794(10) 0.6206(6) 0.8910(3) 0.075(2) Uani 0.770(8) 1 d PDU A 1
H4A H 1.5135 0.6835 0.8935 0.090 Uiso 0.770(8) 1 calc PR A 1
C5A C 1.4785(8) 0.5813(6) 0.8453(2) 0.0626(18) Uani 0.770(8) 1 d PDU A 1
N5A N 1.5315(6) 0.6248(4) 0.79733(19) 0.0732(16) Uani 0.770(8) 1 d PDU A 1
N6A N 1.5744(6) 0.7082(4) 0.8012(2) 0.0712(17) Uani 0.770(8) 1 d PDU A 1
C6A C 1.6262(7) 0.7537(5) 0.7541(2) 0.0605(16) Uani 0.770(8) 1 d PDU A 1
C7A C 1.6235(11) 0.7095(6) 0.7081(3) 0.0755(19) Uani 0.770(8) 1 d PDU A 1
H7A H 1.5885 0.6467 0.7066 0.091 Uiso 0.770(8) 1 calc PR A 1
C8A C 1.6742(12) 0.7610(7) 0.6641(3) 0.081(2) Uani 0.770(8) 1 d PDU A 1
H8A H 1.6715 0.7332 0.6329 0.097 Uiso 0.770(8) 1 calc PR A 1
C9A C 1.6814(13) 0.8460(7) 0.7563(2) 0.0680(18) Uani 0.770(8) 1 d PDU A 1
H9A H 1.6838 0.8747 0.7873 0.082 Uiso 0.770(8) 1 calc PR A 1
C10A C 1.7329(12) 0.8953(7) 0.7127(3) 0.080(2) Uani 0.770(8) 1 d PDU A 1
H10A H 1.7707 0.9569 0.7144 0.096 Uiso 0.770(8) 1 calc PR A 1
C11A C 1.7282(12) 0.8531(7) 0.6669(3) 0.078(2) Uani 0.770(8) 1 d PDU A 1
H11A H 1.7617 0.8870 0.6374 0.094 Uiso 0.770(8) 1 calc PR A 1
N1B N 1.374(4) 0.467(2) 0.9221(9) 0.074(5) Uani 0.230(8) 1 d PDU A 2
C1B C 1.400(3) 0.4531(15) 0.8727(10) 0.069(5) Uani 0.230(8) 1 d PDU A 2
H1B H 1.3847 0.3899 0.8606 0.083 Uiso 0.230(8) 1 calc PR A 2
C2B C 1.449(3) 0.5291(15) 0.8390(6) 0.066(5) Uani 0.230(8) 1 d PDU A 2
H2B H 1.4610 0.5187 0.8046 0.080 Uiso 0.230(8) 1 calc PR A 2
C3B C 1.389(4) 0.561(2) 0.9374(6) 0.072(5) Uani 0.230(8) 1 d PDU A 2
H3B H 1.3596 0.5763 0.9704 0.086 Uiso 0.230(8) 1 calc PR A 2
C4B C 1.445(3) 0.6364(19) 0.9065(6) 0.067(5) Uani 0.230(8) 1 d PDU A 2
H4B H 1.4603 0.6986 0.9195 0.081 Uiso 0.230(8) 1 calc PR A 2
C5B C 1.478(3) 0.6197(16) 0.8571(6) 0.062(4) Uani 0.230(8) 1 d PDU A 2
N5B N 1.5242(19) 0.6973(12) 0.8197(5) 0.060(4) Uani 0.230(8) 1 d PDU A 2
N6B N 1.571(2) 0.6590(13) 0.7803(5) 0.069(4) Uani 0.230(8) 1 d PDU A 2
C6B C 1.6250(18) 0.7332(13) 0.7440(5) 0.064(4) Uani 0.230(8) 1 d PDU A 2
C7B C 1.643(4) 0.718(2) 0.6924(6) 0.069(5) Uani 0.230(8) 1 d PDU A 2
H7B H 1.6210 0.6571 0.6800 0.083 Uiso 0.230(8) 1 calc PR A 2
C8B C 1.694(4) 0.795(2) 0.6598(6) 0.075(6) Uani 0.230(8) 1 d PDU A 2
H8B H 1.7027 0.7874 0.6250 0.091 Uiso 0.230(8) 1 calc PR A 2
C9B C 1.662(5) 0.822(2) 0.7623(7) 0.066(5) Uani 0.230(8) 1 d PDU A 2
H9B H 1.6526 0.8309 0.7970 0.079 Uiso 0.230(8) 1 calc PR A 2
C10B C 1.711(4) 0.898(2) 0.7294(10) 0.068(5) Uani 0.230(8) 1 d PDU A 2
H10B H 1.7309 0.9603 0.7416 0.081 Uiso 0.230(8) 1 calc PR A 2
C11B C 1.732(4) 0.883(2) 0.6788(10) 0.077(6) Uani 0.230(8) 1 d PDU A 2
H11B H 1.7717 0.9312 0.6571 0.093 Uiso 0.230(8) 1 calc PR A 2
N2A N 0.9253(18) 0.5418(11) 0.8653(4) 0.086(3) Uani 0.582(8) 1 d PDU B 1
C12A C 0.9505(13) 0.5278(9) 0.8170(5) 0.081(3) Uani 0.582(8) 1 d PDU B 1
H12A H 0.9256 0.4677 0.8050 0.097 Uiso 0.582(8) 1 calc PR B 1
C13A C 1.0114(13) 0.5958(9) 0.7824(4) 0.078(4) Uani 0.582(8) 1 d PDU B 1
H13A H 1.0242 0.5825 0.7483 0.093 Uiso 0.582(8) 1 calc PR B 1
C14A C 0.958(2) 0.6311(12) 0.8811(3) 0.097(4) Uani 0.582(8) 1 d PDU B 1
H14A H 0.9321 0.6475 0.9142 0.117 Uiso 0.582(8) 1 calc PR B 1
C15A C 1.0290(19) 0.7007(10) 0.8507(4) 0.088(3) Uani 0.582(8) 1 d PDU B 1
H15A H 1.0597 0.7571 0.8641 0.105 Uiso 0.582(8) 1 calc PR B 1
C16A C 1.0519(12) 0.6828(8) 0.7999(3) 0.062(2) Uani 0.582(8) 1 d PDU B 1
N7A N 1.1094(12) 0.7635(7) 0.7685(2) 0.068(3) Uani 0.582(8) 1 d PDU B 1
N8A N 1.1369(10) 0.7439(6) 0.7240(3) 0.075(2) Uani 0.582(8) 1 d PDU B 1
C17A C 1.1927(10) 0.8208(7) 0.6913(3) 0.070(3) Uani 0.582(8) 1 d PDU B 1
C18A C 1.1981(12) 0.8089(8) 0.6401(4) 0.080(3) Uani 0.582(8) 1 d PDU B 1
H18A H 1.1625 0.7535 0.6277 0.095 Uiso 0.582(8) 1 calc PR B 1
C19A C 1.2579(15) 0.8812(11) 0.6065(4) 0.082(4) Uani 0.582(8) 1 d PDU B 1
H19A H 1.2642 0.8742 0.5716 0.098 Uiso 0.582(8) 1 calc PR B 1
C20A C 1.234(2) 0.9071(13) 0.7104(3) 0.085(4) Uani 0.582(8) 1 d PDU B 1
H20A H 1.2211 0.9169 0.7449 0.102 Uiso 0.582(8) 1 calc PR B 1
C21A C 1.2959(18) 0.9796(10) 0.6784(4) 0.089(3) Uani 0.582(8) 1 d PDU B 1
H21A H 1.3279 1.0364 0.6910 0.107 Uiso 0.582(8) 1 calc PR B 1
C22A C 1.3075(15) 0.9636(10) 0.6271(4) 0.087(3) Uani 0.582(8) 1 d PDU B 1
H22A H 1.3506 1.0102 0.6053 0.105 Uiso 0.582(8) 1 calc PR B 1
N2B N 0.927(2) 0.5518(15) 0.8809(4) 0.078(4) Uani 0.418(8) 1 d PDU B 2
C12B C 0.9219(17) 0.5111(10) 0.8372(6) 0.081(4) Uani 0.418(8) 1 d PDU B 2
H12B H 0.8804 0.4508 0.8374 0.097 Uiso 0.418(8) 1 calc PR B 2
C13B C 0.9732(16) 0.5503(12) 0.7913(5) 0.077(4) Uani 0.418(8) 1 d PDU B 2
H13B H 0.9704 0.5157 0.7619 0.092 Uiso 0.418(8) 1 calc PR B 2
C14B C 0.998(3) 0.6328(15) 0.8804(4) 0.083(4) Uani 0.418(8) 1 d PDU B 2
H14B H 1.0197 0.6551 0.9114 0.100 Uiso 0.418(8) 1 calc PR B 2
C15B C 1.043(3) 0.6853(14) 0.8353(5) 0.081(4) Uani 0.418(8) 1 d PDU B 2
H15B H 1.0809 0.7472 0.8358 0.097 Uiso 0.418(8) 1 calc PR B 2
C16B C 1.029(2) 0.6422(12) 0.7903(4) 0.071(5) Uani 0.418(8) 1 d PDU B 2
N7B N 1.0897(9) 0.6869(6) 0.7449(3) 0.070(3) Uani 0.418(8) 1 d PDU B 2
N8B N 1.1295(17) 0.7725(10) 0.7480(4) 0.067(4) Uani 0.418(8) 1 d PDU B 2
C17B C 1.1837(14) 0.8227(9) 0.7034(4) 0.070(3) Uani 0.418(8) 1 d PDU B 2
C18B C 1.1621(19) 0.7878(11) 0.6572(5) 0.095(4) Uani 0.418(8) 1 d PDU B 2
H18B H 1.1138 0.7315 0.6555 0.114 Uiso 0.418(8) 1 calc PR B 2
C19B C 1.214(2) 0.8379(14) 0.6125(5) 0.098(5) Uani 0.418(8) 1 d PDU B 2
H19B H 1.1991 0.8161 0.5806 0.118 Uiso 0.418(8) 1 calc PR B 2
C20B C 1.262(3) 0.9027(17) 0.7073(4) 0.079(4) Uani 0.418(8) 1 d PDU B 2
H20B H 1.2817 0.9211 0.7394 0.095 Uiso 0.418(8) 1 calc PR B 2
C21B C 1.311(3) 0.9557(15) 0.6638(6) 0.098(5) Uani 0.418(8) 1 d PDU B 2
H21B H 1.3585 1.0124 0.6659 0.118 Uiso 0.418(8) 1 calc PR B 2
C22B C 1.287(3) 0.9209(17) 0.6172(6) 0.095(6) Uani 0.418(8) 1 d PDU B 2
H22B H 1.3211 0.9545 0.5878 0.114 Uiso 0.418(8) 1 calc PR B 2
N3A N 1.5389(10) 0.4743(5) 0.6273(3) 0.070(2) Uani 0.753(7) 1 d PDU C 1
C23A C 1.4271(9) 0.5026(6) 0.6598(3) 0.077(2) Uani 0.753(7) 1 d PDU C 1
H23A H 1.3762 0.5771 0.6587 0.092 Uiso 0.753(7) 1 calc PR C 1
C24A C 1.3796(8) 0.4289(6) 0.6956(3) 0.0717(19) Uani 0.753(7) 1 d PDU C 1
H24A H 1.2997 0.4539 0.7175 0.086 Uiso 0.753(7) 1 calc PR C 1
C25A C 1.6097(11) 0.3669(6) 0.6292(3) 0.070(2) Uani 0.753(7) 1 d PDU C 1
H25A H 1.6894 0.3445 0.6069 0.084 Uiso 0.753(7) 1 calc PR C 1
C26A C 1.5690(10) 0.2867(5) 0.6633(3) 0.0678(18) Uani 0.753(7) 1 d PDU C 1
H26A H 1.6193 0.2124 0.6629 0.081 Uiso 0.753(7) 1 calc PR C 1
C27A C 1.4531(8) 0.3187(6) 0.6978(2) 0.0591(17) Uani 0.753(7) 1 d PDU C 1
N9A N 1.4191(6) 0.2309(4) 0.7318(2) 0.0666(16) Uani 0.753(7) 1 d PDU C 1
N10A N 1.3394(6) 0.2654(4) 0.76736(19) 0.0686(16) Uani 0.753(7) 1 d PDU C 1
C28A C 1.3058(7) 0.1814(5) 0.8029(2) 0.0621(17) Uani 0.753(7) 1 d PDU C 1
C29A C 1.2033(10) 0.2163(5) 0.8409(3) 0.078(2) Uani 0.753(7) 1 d PDU C 1
H29A H 1.1580 0.2912 0.8421 0.094 Uiso 0.753(7) 1 calc PR C 1
C30A C 1.1690(10) 0.1373(8) 0.8773(3) 0.093(2) Uani 0.753(7) 1 d PDU C 1
H30A H 1.1019 0.1599 0.9035 0.111 Uiso 0.753(7) 1 calc PR C 1
C31A C 1.3731(14) 0.0692(5) 0.8007(4) 0.0711(19) Uani 0.753(7) 1 d PDU C 1
H31A H 1.4431 0.0462 0.7754 0.085 Uiso 0.753(7) 1 calc PR C 1
C32A C 1.3349(10) -0.0072(5) 0.8364(3) 0.076(2) Uani 0.753(7) 1 d PDU C 1
H32A H 1.3777 -0.0822 0.8346 0.091 Uiso 0.753(7) 1 calc PR C 1
C33A C 1.2339(10) 0.0263(7) 0.8748(3) 0.082(2) Uani 0.753(7) 1 d PDU C 1
H33A H 1.2096 -0.0259 0.8989 0.099 Uiso 0.753(7) 1 calc PR C 1
N3B N 1.561(3) 0.4468(19) 0.6189(9) 0.064(5) Uani 0.247(7) 1 d PDU C 2
C23B C 1.451(3) 0.5108(12) 0.6433(8) 0.075(5) Uani 0.247(7) 1 d PDU C 2
H23B H 1.4220 0.5857 0.6315 0.090 Uiso 0.247(7) 1 calc PR C 2
C24B C 1.375(2) 0.4748(12) 0.6851(7) 0.066(5) Uani 0.247(7) 1 d PDU C 2
H24B H 1.2987 0.5245 0.7009 0.079 Uiso 0.247(7) 1 calc PR C 2
C25B C 1.599(3) 0.3392(19) 0.6357(11) 0.069(5) Uani 0.247(7) 1 d PDU C 2
H25B H 1.6751 0.2916 0.6189 0.083 Uiso 0.247(7) 1 calc PR C 2
C26B C 1.529(3) 0.2952(12) 0.6775(9) 0.063(5) Uani 0.247(7) 1 d PDU C 2
H26B H 1.5593 0.2199 0.6882 0.076 Uiso 0.247(7) 1 calc PR C 2
C27B C 1.414(3) 0.3639(12) 0.7027(8) 0.064(5) Uani 0.247(7) 1 d PDU C 2
N9B N 1.3519(16) 0.3156(9) 0.7470(5) 0.064(4) Uani 0.247(7) 1 d PDU C 2
N10B N 1.382(2) 0.2154(11) 0.7510(6) 0.067(4) Uani 0.247(7) 1 d PDU C 2
C28B C 1.3202(19) 0.1658(10) 0.7948(5) 0.065(4) Uani 0.247(7) 1 d PDU C 2
C29B C 1.217(3) 0.2346(11) 0.8236(8) 0.071(5) Uani 0.247(7) 1 d PDU C 2
H29B H 1.1905 0.3107 0.8148 0.086 Uiso 0.247(7) 1 calc PR C 2
C30B C 1.152(3) 0.1883(17) 0.8664(8) 0.077(5) Uani 0.247(7) 1 d PDU C 2
H30B H 1.0796 0.2337 0.8853 0.092 Uiso 0.247(7) 1 calc PR C 2
C31B C 1.360(4) 0.0517(10) 0.8083(11) 0.067(5) Uani 0.247(7) 1 d PDU C 2
H31B H 1.4288 0.0052 0.7885 0.080 Uiso 0.247(7) 1 calc PR C 2
C32B C 1.298(3) 0.0084(12) 0.8510(9) 0.070(5) Uani 0.247(7) 1 d PDU C 2
H32B H 1.3251 -0.0676 0.8601 0.084 Uiso 0.247(7) 1 calc PR C 2
C33B C 1.196(3) 0.0758(18) 0.8806(8) 0.075(6) Uani 0.247(7) 1 d PDU C 2
H33B H 1.1567 0.0457 0.9099 0.090 Uiso 0.247(7) 1 calc PR C 2
N4 N 1.0951(4) 0.5249(3) 0.56177(14) 0.0830(10) Uani 1 1 d . . .
N11 N 1.0022(4) 0.2982(3) 0.68006(13) 0.0770(9) Uani 1 1 d . . .
N12 N 0.9075(4) 0.3363(3) 0.71042(13) 0.0767(9) Uani 1 1 d . . .
C34 C 0.9911(5) 0.5590(4) 0.5966(2) 0.0971(15) Uani 1 1 d . . .
H34 H 0.9404 0.6337 0.5939 0.116 Uiso 1 1 calc R . .
C35 C 0.9535(5) 0.4913(4) 0.63629(17) 0.0897(13) Uani 1 1 d . . .
H35 H 0.8788 0.5191 0.6595 0.108 Uiso 1 1 calc R . .
C36 C 1.1644(6) 0.4198(4) 0.56748(17) 0.0983(15) Uani 1 1 d . . .
H36 H 1.2384 0.3932 0.5439 0.118 Uiso 1 1 calc R . .
C37 C 1.1353(6) 0.3454(4) 0.60621(17) 0.0923(14) Uani 1 1 d . . .
H37 H 1.1886 0.2713 0.6083 0.111 Uiso 1 1 calc R . .
C38 C 1.0295(5) 0.3813(4) 0.64061(15) 0.0703(11) Uani 1 1 d . . .
C39 C 0.8768(5) 0.2533(4) 0.74870(14) 0.0677(10) Uani 1 1 d . . .
C40 C 0.7708(5) 0.2953(4) 0.78401(17) 0.0877(13) Uani 1 1 d . . .
H40 H 0.7241 0.3707 0.7816 0.105 Uiso 1 1 calc R . .
C41 C 0.7338(6) 0.2249(5) 0.82318(18) 0.1079(16) Uani 1 1 d . . .
H41 H 0.6636 0.2525 0.8477 0.129 Uiso 1 1 calc R . .
C42 C 0.9442(5) 0.1412(4) 0.75064(15) 0.0807(12) Uani 1 1 d . . .
H42 H 1.0142 0.1132 0.7261 0.097 Uiso 1 1 calc R . .
C43 C 0.9056(6) 0.0718(4) 0.78960(19) 0.0994(15) Uani 1 1 d . . .
H43 H 0.9502 -0.0039 0.7916 0.119 Uiso 1 1 calc R . .
C44 C 0.8020(7) 0.1135(5) 0.8254(2) 0.1095(18) Uani 1 1 d . . .
H44 H 0.7775 0.0657 0.8517 0.131 Uiso 1 1 calc R . .
I1 I 1.37580(3) 0.09208(2) 1.067767(11) 0.08257(11) Uani 1 1 d . . .
I2 I 0.73502(3) 0.17870(2) 0.984814(11) 0.08503(12) Uani 1 1 d . . .
O1 O 1.3373(3) 0.3216(2) 1.00477(10) 0.0872(9) Uani 1 1 d . . .
H1O H 1.3308 0.3832 0.9898 0.131 Uiso 1 1 d R . .
O2 O 0.8246(3) 0.3969(2) 0.93978(12) 0.0978(9) Uani 1 1 d . . .
H2O H 0.8315 0.4609 0.9364 0.147 Uiso 1 1 d R . .
C45 C 1.1909(4) 0.1932(3) 1.02405(12) 0.0569(9) Uani 1 1 d . . .
C46 C 1.2043(4) 0.2939(3) 0.99968(14) 0.0620(9) Uani 1 1 d . . .
C47 C 1.0813(4) 0.3614(3) 0.97241(14) 0.0684(10) Uani 1 1 d . . .
H47 H 1.0891 0.4294 0.9566 0.082 Uiso 1 1 calc R . .
C48 C 0.9461(4) 0.3314(3) 0.96775(14) 0.0639(10) Uani 1 1 d . . .
C49 C 0.9351(4) 0.2304(3) 0.99178(13) 0.0579(9) Uani 1 1 d . . .
C50 C 1.0564(4) 0.1628(3) 1.01989(13) 0.0593(9) Uani 1 1 d . . .
H50 H 1.0477 0.0956 1.0364 0.071 Uiso 1 1 calc R . .
I3 I 0.91370(3) 0.08742(2) 0.576096(11) 0.08534(11) Uani 1 1 d . . .
I4 I 0.27820(3) 0.16422(2) 0.490822(10) 0.06971(10) Uani 1 1 d . . .
O3 O 0.8713(3) 0.3201(2) 0.51338(10) 0.0884(9) Uani 1 1 d . . .
H3O H 0.8663 0.3784 0.4954 0.133 Uiso 1 1 d R . .
O4 O 0.3668(3) 0.3809(2) 0.44257(10) 0.0799(8) Uani 1 1 d . . .
H4O H 0.3897 0.4353 0.4282 0.120 Uiso 1 1 d R . .
C51 C 0.7285(4) 0.1890(3) 0.53249(13) 0.0566(9) Uani 1 1 d . . .
C52 C 0.7414(4) 0.2888(3) 0.50750(13) 0.0617(9) Uani 1 1 d . . .
C53 C 0.6188(4) 0.3531(3) 0.47831(13) 0.0638(10) Uani 1 1 d . . .
H53 H 0.6248 0.4213 0.4622 0.077 Uiso 1 1 calc R . .
C54 C 0.4867(4) 0.3190(3) 0.47240(13) 0.0562(9) Uani 1 1 d . . .
C55 C 0.4755(4) 0.2193(3) 0.49808(12) 0.0507(8) Uani 1 1 d . . .
C56 C 0.5958(4) 0.1558(3) 0.52825(12) 0.0544(9) Uani 1 1 d . . .
H56 H 0.5877 0.0897 0.5460 0.065 Uiso 1 1 calc R . .


_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
N1A C3A 1.326(6) . ?
N1A C1A 1.338(7) . ?
C1A C2A 1.386(8) . ?
C1A H1A 0.9300 . ?
C2A C5A 1.378(7) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.383(7) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.350(8) . ?
C4A H4A 0.9300 . ?
C5A N5A 1.448(7) . ?
N5A N6A 1.224(5) . ?
N6A C6A 1.432(7) . ?
C6A C9A 1.385(7) . ?
C6A C7A 1.389(7) . ?
C7A C8A 1.395(8) . ?
C7A H7A 0.9300 . ?
C8A C11A 1.379(8) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.377(8) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.375(8) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9300 . ?
N1B C3B 1.329(9) . ?
N1B C1B 1.339(10) . ?
C1B C2B 1.387(10) . ?
C1B H1B 0.9300 . ?
C2B C5B 1.372(10) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.379(10) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.355(10) . ?
C4B H4B 0.9300 . ?
C5B N5B 1.444(9) . ?
N5B N6B 1.214(9) . ?
N6B C6B 1.433(9) . ?
C6B C9B 1.383(9) . ?
C6B C7B 1.392(9) . ?
C7B C8B 1.392(10) . ?
C7B H7B 0.9300 . ?
C8B C11B 1.379(11) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.381(10) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.372(11) . ?
C10B H10B 0.9300 . ?
C11B H11B 0.9300 . ?
N2A C12A 1.310(10) . ?
N2A C14A 1.341(9) . ?
C12A C13A 1.389(12) . ?
C12A H12A 0.9300 . ?
C13A C16A 1.366(12) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.394(9) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.383(9) . ?
C15A H15A 0.9300 . ?
C16A N7A 1.439(10) . ?
N7A N8A 1.232(8) . ?
N8A C17A 1.412(8) . ?
C17A C18A 1.370(8) . ?
C17A C20A 1.382(8) . ?
C18A C19A 1.404(12) . ?
C18A H18A 0.9300 . ?
C19A C22A 1.394(14) . ?
C19A H19A 0.9300 . ?
C20A C21A 1.392(8) . ?
C20A H20A 0.9300 . ?
C21A C22A 1.384(11) . ?
C21A H21A 0.9300 . ?
C22A H22A 0.9300 . ?
N2B C12B 1.314(11) . ?
N2B C14B 1.343(10) . ?
C12B C13B 1.377(12) . ?
C12B H12B 0.9300 . ?
C13B C16B 1.375(13) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.400(9) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.375(11) . ?
C15B H15B 0.9300 . ?
C16B N7B 1.431(11) . ?
N7B N8B 1.232(9) . ?
N8B C17B 1.415(9) . ?
C17B C18B 1.368(9) . ?
C17B C20B 1.386(8) . ?
C18B C19B 1.407(12) . ?
C18B H18B 0.9300 . ?
C19B C22B 1.392(15) . ?
C19B H19B 0.9300 . ?
C20B C21B 1.389(9) . ?
C20B H20B 0.9300 . ?
C21B C22B 1.383(12) . ?
C21B H21B 0.9300 . ?
C22B H22B 0.9300 . ?
N3A C23A 1.318(7) . ?
N3A C25A 1.335(7) . ?
C23A C24A 1.392(8) . ?
C23A H23A 0.9300 . ?
C24A C27A 1.370(8) . ?
C24A H24A 0.9300 . ?
C25A C26A 1.395(7) . ?
C25A H25A 0.9300 . ?
C26A C27A 1.386(7) . ?
C26A H26A 0.9300 . ?
C27A N9A 1.439(7) . ?
N9A N10A 1.222(6) . ?
N10A C28A 1.425(6) . ?
C28A C29A 1.382(7) . ?
C28A C31A 1.393(7) . ?
C29A C30A 1.397(9) . ?
C29A H29A 0.9300 . ?
C30A C33A 1.378(9) . ?
C30A H30A 0.9300 . ?
C31A C32A 1.377(7) . ?
C31A H31A 0.9300 . ?
C32A C33A 1.379(8) . ?
C32A H32A 0.9300 . ?
C33A H33A 0.9300 . ?
N3B C23B 1.317(10) . ?
N3B C25B 1.336(9) . ?
C23B C24B 1.389(11) . ?
C23B H23B 0.9300 . ?
C24B C27B 1.379(10) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.396(10) . ?
C25B H25B 0.9300 . ?
C26B C27B 1.381(10) . ?
C26B H26B 0.9300 . ?
C27B N9B 1.433(9) . ?
N9B N10B 1.212(9) . ?
N10B C28B 1.429(8) . ?
C28B C29B 1.381(10) . ?
C28B C31B 1.395(9) . ?
C29B C30B 1.401(11) . ?
C29B H29B 0.9300 . ?
C30B C33B 1.379(12) . ?
C30B H30B 0.9300 . ?
C31B C32B 1.374(10) . ?
C31B H31B 0.9300 . ?
C32B C33B 1.377(11) . ?
C32B H32B 0.9300 . ?
C33B H33B 0.9300 . ?
N4 C36 1.303(5) . ?
N4 C34 1.328(5) . ?
N11 N12 1.206(4) . ?
N11 C38 1.458(5) . ?
N12 C39 1.449(5) . ?
C34 C35 1.371(6) . ?
C34 H34 0.9300 . ?
C35 C38 1.371(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.378(6) . ?
C36 H36 0.9300 . ?
C37 C38 1.335(5) . ?
C37 H37 0.9300 . ?
C39 C42 1.381(5) . ?
C39 C40 1.373(5) . ?
C40 C41 1.381(6) . ?
C40 H40 0.9300 . ?
C41 C44 1.373(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.375(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.368(7) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?
I1 C45 2.091(3) . ?
I2 C49 2.092(3) . ?
O1 C46 1.349(4) . ?
O1 H1O 0.8197 . ?
O2 C48 1.361(4) . ?
O2 H2O 0.8197 . ?
C45 C50 1.376(4) . ?
C45 C46 1.391(4) . ?
C46 C47 1.369(5) . ?
C47 C48 1.381(5) . ?
C47 H47 0.9300 . ?
C48 C49 1.385(5) . ?
C49 C50 1.370(5) . ?
C50 H50 0.9300 . ?
I3 C51 2.094(3) . ?
I4 C55 2.093(3) . ?
O3 C52 1.349(4) . ?
O3 H3O 0.8208 . ?
O4 C54 1.361(4) . ?
O4 H4O 0.8193 . ?
C51 C56 1.378(4) . ?
C51 C52 1.386(4) . ?
C52 C53 1.378(5) . ?
C53 C54 1.386(4) . ?
C53 H53 0.9300 . ?
C54 C55 1.387(4) . ?
C55 C56 1.375(4) . ?
C56 H56 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3A N1A C1A 117.1(5) . . ?
N1A C1A C2A 122.9(6) . . ?
N1A C1A H1A 118.6 . . ?
C2A C1A H1A 118.6 . . ?
C5A C2A C1A 118.8(6) . . ?
C5A C2A H2A 120.6 . . ?
C1A C2A H2A 120.6 . . ?
N1A C3A C4A 122.9(5) . . ?
N1A C3A H3A 118.6 . . ?
C4A C3A H3A 118.6 . . ?
C5A C4A C3A 120.0(5) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C2A 118.4(6) . . ?
C4A C5A N5A 126.7(6) . . ?
C2A C5A N5A 114.9(6) . . ?
N6A N5A C5A 112.5(5) . . ?
N5A N6A C6A 113.7(5) . . ?
C9A C6A C7A 120.2(5) . . ?
C9A C6A N6A 116.5(6) . . ?
C7A C6A N6A 123.2(6) . . ?
C8A C7A C6A 118.9(6) . . ?
C8A C7A H7A 120.5 . . ?
C6A C7A H7A 120.6 . . ?
C11A C8A C7A 120.1(6) . . ?
C11A C8A H8A 119.9 . . ?
C7A C8A H8A 119.9 . . ?
C10A C9A C6A 120.4(5) . . ?
C10A C9A H9A 119.8 . . ?
C6A C9A H9A 119.8 . . ?
C11A C10A C9A 119.7(6) . . ?
C11A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C10A C11A C8A 120.7(6) . . ?
C10A C11A H11A 119.7 . . ?
C8A C11A H11A 119.7 . . ?
C3B N1B C1B 116.9(8) . . ?
N1B C1B C2B 122.6(8) . . ?
N1B C1B H1B 118.7 . . ?
C2B C1B H1B 118.7 . . ?
C5B C2B C1B 119.1(8) . . ?
C5B C2B H2B 120.4 . . ?
C1B C2B H2B 120.5 . . ?
N1B C3B C4B 122.9(8) . . ?
N1B C3B H3B 118.6 . . ?
C4B C3B H3B 118.6 . . ?
C5B C4B C3B 119.9(8) . . ?
C5B C4B H4B 120.1 . . ?
C3B C4B H4B 120.1 . . ?
C4B C5B C2B 118.1(8) . . ?
C4B C5B N5B 125.2(10) . . ?
C2B C5B N5B 116.2(10) . . ?
N6B N5B C5B 114.0(9) . . ?
N5B N6B C6B 114.5(8) . . ?
C9B C6B C7B 120.1(7) . . ?
C9B C6B N6B 117.1(9) . . ?
C7B C6B N6B 122.8(9) . . ?
C8B C7B C6B 118.9(8) . . ?
C8B C7B H7B 120.5 . . ?
C6B C7B H7B 120.6 . . ?
C11B C8B C7B 120.2(8) . . ?
C11B C8B H8B 119.9 . . ?
C7B C8B H8B 119.9 . . ?
C10B C9B C6B 120.4(8) . . ?
C10B C9B H9B 119.8 . . ?
C6B C9B H9B 119.8 . . ?
C11B C10B C9B 119.6(8) . . ?
C11B C10B H10B 120.2 . . ?
C9B C10B H10B 120.2 . . ?
C10B C11B C8B 120.6(8) . . ?
C10B C11B H11B 119.7 . . ?
C8B C11B H11B 119.7 . . ?
C12A N2A C14A 116.0(7) . . ?
N2A C12A C13A 125.0(9) . . ?
N2A C12A H12A 117.5 . . ?
C13A C12A H12A 117.5 . . ?
C16A C13A C12A 118.1(11) . . ?
C16A C13A H13A 121.0 . . ?
C12A C13A H13A 121.0 . . ?
N2A C14A C15A 123.8(7) . . ?
N2A C14A H14A 118.1 . . ?
C15A C14A H14A 118.1 . . ?
C16A C15A C14A 117.6(7) . . ?
C16A C15A H15A 121.2 . . ?
C14A C15A H15A 121.2 . . ?
C13A C16A C15A 119.2(10) . . ?
C13A C16A N7A 124.8(10) . . ?
C15A C16A N7A 115.9(8) . . ?
N8A N7A C16A 115.4(7) . . ?
N7A N8A C17A 117.9(6) . . ?
C18A C17A C20A 121.6(7) . . ?
C18A C17A N8A 117.5(8) . . ?
C20A C17A N8A 120.8(6) . . ?
C17A C18A C19A 119.4(8) . . ?
C17A C18A H18A 120.3 . . ?
C19A C18A H18A 120.3 . . ?
C22A C19A C18A 117.8(10) . . ?
C22A C19A H19A 121.1 . . ?
C18A C19A H19A 121.1 . . ?
C17A C20A C21A 120.5(7) . . ?
C17A C20A H20A 119.8 . . ?
C21A C20A H20A 119.8 . . ?
C22A C21A C20A 117.2(8) . . ?
C22A C21A H21A 121.4 . . ?
C20A C21A H21A 121.4 . . ?
C21A C22A C19A 123.3(11) . . ?
C21A C22A H22A 118.4 . . ?
C19A C22A H22A 118.4 . . ?
C12B N2B C14B 115.7(8) . . ?
N2B C12B C13B 125.5(11) . . ?
N2B C12B H12B 117.2 . . ?
C13B C12B H12B 117.3 . . ?
C12B C13B C16B 117.6(11) . . ?
C12B C13B H13B 121.2 . . ?
C16B C13B H13B 121.2 . . ?
N2B C14B C15B 123.2(8) . . ?
N2B C14B H14B 118.4 . . ?
C15B C14B H14B 118.4 . . ?
C16B C15B C14B 117.7(8) . . ?
C16B C15B H15B 121.2 . . ?
C14B C15B H15B 121.2 . . ?
C15B C16B C13B 119.4(10) . . ?
C15B C16B N7B 118.4(9) . . ?
C13B C16B N7B 121.9(11) . . ?
N8B N7B C16B 116.0(8) . . ?
N7B N8B C17B 118.1(8) . . ?
C18B C17B C20B 121.3(8) . . ?
C18B C17B N8B 118.8(8) . . ?
C20B C17B N8B 119.9(8) . . ?
C17B C18B C19B 119.5(9) . . ?
C17B C18B H18B 120.3 . . ?
C19B C18B H18B 120.2 . . ?
C22B C19B C18B 118.1(11) . . ?
C22B C19B H19B 121.0 . . ?
C18B C19B H19B 121.0 . . ?
C17B C20B C21B 120.6(8) . . ?
C17B C20B H20B 119.7 . . ?
C21B C20B H20B 119.7 . . ?
C22B C21B C20B 117.5(9) . . ?
C22B C21B H21B 121.2 . . ?
C20B C21B H21B 121.2 . . ?
C21B C22B C19B 122.9(11) . . ?
C21B C22B H22B 118.6 . . ?
C19B C22B H22B 118.6 . . ?
C23A N3A C25A 116.7(5) . . ?
N3A C23A C24A 124.7(6) . . ?
N3A C23A H23A 117.6 . . ?
C24A C23A H23A 117.6 . . ?
C27A C24A C23A 118.6(6) . . ?
C27A C24A H24A 120.7 . . ?
C23A C24A H24A 120.7 . . ?
N3A C25A C26A 122.7(5) . . ?
N3A C25A H25A 118.7 . . ?
C26A C25A H25A 118.7 . . ?
C27A C26A C25A 119.5(6) . . ?
C27A C26A H26A 120.2 . . ?
C25A C26A H26A 120.2 . . ?
C24A C27A C26A 117.7(6) . . ?
C24A C27A N9A 126.3(6) . . ?
C26A C27A N9A 115.9(6) . . ?
N10A N9A C27A 112.3(5) . . ?
N9A N10A C28A 114.5(4) . . ?
C29A C28A C31A 120.6(5) . . ?
C29A C28A N10A 116.7(6) . . ?
C31A C28A N10A 122.7(5) . . ?
C28A C29A C30A 119.0(6) . . ?
C28A C29A H29A 120.5 . . ?
C30A C29A H29A 120.5 . . ?
C33A C30A C29A 120.4(7) . . ?
C33A C30A H30A 119.8 . . ?
C29A C30A H30A 119.8 . . ?
C32A C31A C28A 119.3(5) . . ?
C32A C31A H31A 120.3 . . ?
C28A C31A H31A 120.3 . . ?
C31A C32A C33A 120.7(6) . . ?
C31A C32A H32A 119.6 . . ?
C33A C32A H32A 119.6 . . ?
C32A C33A C30A 119.9(7) . . ?
C32A C33A H33A 120.1 . . ?
C30A C33A H33A 120.1 . . ?
C23B N3B C25B 116.5(8) . . ?
N3B C23B C24B 125.0(9) . . ?
N3B C23B H23B 117.5 . . ?
C24B C23B H23B 117.5 . . ?
C23B C24B C27B 118.6(8) . . ?
C23B C24B H24B 120.7 . . ?
C27B C24B H24B 120.7 . . ?
N3B C25B C26B 122.7(8) . . ?
N3B C25B H25B 118.6 . . ?
C26B C25B H25B 118.6 . . ?
C27B C26B C25B 119.8(8) . . ?
C27B C26B H26B 120.1 . . ?
C25B C26B H26B 120.1 . . ?
C26B C27B C24B 117.4(8) . . ?
C26B C27B N9B 117.5(10) . . ?
C24B C27B N9B 125.0(10) . . ?
N10B N9B C27B 114.4(8) . . ?
N9B N10B C28B 115.1(8) . . ?
C29B C28B C31B 120.3(7) . . ?
C29B C28B N10B 117.8(8) . . ?
C31B C28B N10B 121.9(8) . . ?
C28B C29B C30B 119.2(8) . . ?
C28B C29B H29B 120.4 . . ?
C30B C29B H29B 120.4 . . ?
C33B C30B C29B 120.4(10) . . ?
C33B C30B H30B 119.8 . . ?
C29B C30B H30B 119.8 . . ?
C32B C31B C28B 119.5(8) . . ?
C32B C31B H31B 120.3 . . ?
C28B C31B H31B 120.3 . . ?
C31B C32B C33B 121.1(8) . . ?
C31B C32B H32B 119.4 . . ?
C33B C32B H32B 119.4 . . ?
C32B C33B C30B 119.5(10) . . ?
C32B C33B H33B 120.2 . . ?
C30B C33B H33B 120.2 . . ?
C36 N4 C34 115.6(4) . . ?
N12 N11 C38 113.1(4) . . ?
N11 N12 C39 113.1(4) . . ?
N4 C34 C35 124.4(4) . . ?
N4 C34 H34 117.8 . . ?
C35 C34 H34 117.8 . . ?
C34 C35 C38 117.8(4) . . ?
C34 C35 H35 121.1 . . ?
C38 C35 H35 121.1 . . ?
N4 C36 C37 124.3(5) . . ?
N4 C36 H36 117.8 . . ?
C37 C36 H36 117.8 . . ?
C38 C37 C36 119.1(4) . . ?
C38 C37 H37 120.4 . . ?
C36 C37 H37 120.4 . . ?
C37 C38 C35 118.8(4) . . ?
C37 C38 N11 116.4(4) . . ?
C35 C38 N11 124.8(4) . . ?
C42 C39 C40 121.2(4) . . ?
C42 C39 N12 124.8(4) . . ?
C40 C39 N12 114.0(4) . . ?
C39 C40 C41 119.6(5) . . ?
C39 C40 H40 120.2 . . ?
C41 C40 H40 120.2 . . ?
C44 C41 C40 119.2(5) . . ?
C44 C41 H41 120.4 . . ?
C40 C41 H41 120.4 . . ?
C43 C42 C39 118.6(4) . . ?
C43 C42 H42 120.7 . . ?
C39 C42 H42 120.7 . . ?
C44 C43 C42 120.4(5) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C41 121.0(5) . . ?
C43 C44 H44 119.5 . . ?
C41 C44 H44 119.5 . . ?
C46 O1 H1O 109.8 . . ?
C48 O2 H2O 109.6 . . ?
C50 C45 C46 119.8(3) . . ?
C50 C45 I1 121.2(3) . . ?
C46 C45 I1 118.9(2) . . ?
O1 C46 C47 122.8(3) . . ?
O1 C46 C45 118.4(3) . . ?
C47 C46 C45 118.8(3) . . ?
C46 C47 C48 121.8(3) . . ?
C46 C47 H47 119.1 . . ?
C48 C47 H47 119.1 . . ?
O2 C48 C49 119.0(3) . . ?
O2 C48 C47 122.2(3) . . ?
C49 C48 C47 118.7(3) . . ?
C50 C49 C48 120.0(3) . . ?
C50 C49 I2 119.4(2) . . ?
C48 C49 I2 120.6(3) . . ?
C49 C50 C45 120.8(3) . . ?
C49 C50 H50 119.6 . . ?
C45 C50 H50 119.6 . . ?
C52 O3 H3O 109.4 . . ?
C54 O4 H4O 109.4 . . ?
C56 C51 C52 120.5(3) . . ?
C56 C51 I3 120.1(2) . . ?
C52 C51 I3 119.4(3) . . ?
O3 C52 C53 122.6(3) . . ?
O3 C52 C51 119.1(3) . . ?
C53 C52 C51 118.2(3) . . ?
C52 C53 C54 121.8(3) . . ?
C52 C53 H53 119.1 . . ?
C54 C53 H53 119.1 . . ?
O4 C54 C55 118.9(3) . . ?
O4 C54 C53 122.0(3) . . ?
C55 C54 C53 119.1(3) . . ?
C56 C55 C54 119.5(3) . . ?
C56 C55 I4 119.8(2) . . ?
C54 C55 I4 120.7(2) . . ?
C51 C56 C55 120.8(3) . . ?
C51 C56 H56 119.6 . . ?
C55 C56 H56 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3A N1A C1A C2A -1.2(10) . . . . ?
N1A C1A C2A C5A 0.1(9) . . . . ?
C1A N1A C3A C4A 1.9(12) . . . . ?
N1A C3A C4A C5A -1.5(13) . . . . ?
C3A C4A C5A C2A 0.3(11) . . . . ?
C3A C4A C5A N5A -177.6(7) . . . . ?
C1A C2A C5A C4A 0.4(10) . . . . ?
C1A C2A C5A N5A 178.5(6) . . . . ?
C4A C5A N5A N6A -3.0(10) . . . . ?
C2A C5A N5A N6A 179.1(6) . . . . ?
C5A N5A N6A C6A -179.4(5) . . . . ?
N5A N6A C6A C9A -177.8(7) . . . . ?
N5A N6A C6A C7A 2.0(8) . . . . ?
C9A C6A C7A C8A -1.4(10) . . . . ?
N6A C6A C7A C8A 178.9(7) . . . . ?
C6A C7A C8A C11A 1.1(12) . . . . ?
C7A C6A C9A C10A 0.6(12) . . . . ?
N6A C6A C9A C10A -179.7(8) . . . . ?
C6A C9A C10A C11A 0.5(14) . . . . ?
C9A C10A C11A C8A -0.8(14) . . . . ?
C7A C8A C11A C10A 0.0(14) . . . . ?
C3B N1B C1B C2B 4(2) . . . . ?
N1B C1B C2B C5B 3.1(18) . . . . ?
C1B N1B C3B C4B -7(4) . . . . ?
N1B C3B C4B C5B 4(5) . . . . ?
C3B C4B C5B C2B 2(4) . . . . ?
C3B C4B C5B N5B 174(3) . . . . ?
C1B C2B C5B C4B -6(3) . . . . ?
C1B C2B C5B N5B -178.2(18) . . . . ?
C4B C5B N5B N6B 169(3) . . . . ?
C2B C5B N5B N6B -19(3) . . . . ?
C5B N5B N6B C6B -176.7(16) . . . . ?
N5B N6B C6B C9B 19(3) . . . . ?
N5B N6B C6B C7B -162(2) . . . . ?
C9B C6B C7B C8B -2(3) . . . . ?
N6B C6B C7B C8B 179(2) . . . . ?
C6B C7B C8B C11B 3(4) . . . . ?
C7B C6B C9B C10B 2(4) . . . . ?
N6B C6B C9B C10B -179(3) . . . . ?
C6B C9B C10B C11B -3(5) . . . . ?
C9B C10B C11B C8B 4(6) . . . . ?
C7B C8B C11B C10B -4(5) . . . . ?
C14A N2A C12A C13A 1.9(15) . . . . ?
N2A C12A C13A C16A 1.6(12) . . . . ?
C12A N2A C14A C15A -6(2) . . . . ?
N2A C14A C15A C16A 7(2) . . . . ?
C12A C13A C16A C15A -0.9(16) . . . . ?
C12A C13A C16A N7A -176.9(9) . . . . ?
C14A C15A C16A C13A -3(2) . . . . ?
C14A C15A C16A N7A 173.3(13) . . . . ?
C13A C16A N7A N8A -7.5(17) . . . . ?
C15A C16A N7A N8A 176.4(12) . . . . ?
C16A N7A N8A C17A 179.6(7) . . . . ?
N7A N8A C17A C18A -169.0(10) . . . . ?
N7A N8A C17A C20A 8.4(15) . . . . ?
C20A C17A C18A C19A 4.8(15) . . . . ?
N8A C17A C18A C19A -177.8(9) . . . . ?
C17A C18A C19A C22A -0.9(16) . . . . ?
C18A C17A C20A C21A -6(2) . . . . ?
N8A C17A C20A C21A 177.0(12) . . . . ?
C17A C20A C21A C22A 2(2) . . . . ?
C20A C21A C22A C19A 1(2) . . . . ?
C18A C19A C22A C21A -2.2(18) . . . . ?
C14B N2B C12B C13B -5.3(18) . . . . ?
N2B C12B C13B C16B -2.6(15) . . . . ?
C12B N2B C14B C15B 11(3) . . . . ?
N2B C14B C15B C16B -8(3) . . . . ?
C14B C15B C16B C13B 0(3) . . . . ?
C14B C15B C16B N7B -173.0(17) . . . . ?
C12B C13B C16B C15B 5(2) . . . . ?
C12B C13B C16B N7B 177.8(13) . . . . ?
C15B C16B N7B N8B -11(2) . . . . ?
C13B C16B N7B N8B 176.7(15) . . . . ?
C16B N7B N8B C17B -177.1(11) . . . . ?
N7B N8B C17B C18B 12.7(15) . . . . ?
N7B N8B C17B C20B -165.1(18) . . . . ?
C20B C17B C18B C19B -3(2) . . . . ?
N8B C17B C18B C19B 179.2(13) . . . . ?
C17B C18B C19B C22B 1(2) . . . . ?
C18B C17B C20B C21B 5(3) . . . . ?
N8B C17B C20B C21B -177.6(17) . . . . ?
C17B C20B C21B C22B -4(3) . . . . ?
C20B C21B C22B C19B 1(3) . . . . ?
C18B C19B C22B C21B 0(3) . . . . ?
C25A N3A C23A C24A 0.5(10) . . . . ?
N3A C23A C24A C27A 0.0(9) . . . . ?
C23A N3A C25A C26A 0.3(14) . . . . ?
N3A C25A C26A C27A -1.6(15) . . . . ?
C23A C24A C27A C26A -1.3(10) . . . . ?
C23A C24A C27A N9A -179.5(7) . . . . ?
C25A C26A C27A C24A 2.1(12) . . . . ?
C25A C26A C27A N9A -179.6(8) . . . . ?
C24A C27A N9A N10A -15.7(10) . . . . ?
C26A C27A N9A N10A 166.2(7) . . . . ?
C27A N9A N10A C28A -178.5(5) . . . . ?
N9A N10A C28A C29A -173.5(6) . . . . ?
N9A N10A C28A C31A 7.4(10) . . . . ?
C31A C28A C29A C30A 0.5(11) . . . . ?
N10A C28A C29A C30A -178.6(7) . . . . ?
C28A C29A C30A C33A -1.3(12) . . . . ?
C29A C28A C31A C32A 1.0(14) . . . . ?
N10A C28A C31A C32A 180.0(8) . . . . ?
C28A C31A C32A C33A -1.5(16) . . . . ?
C31A C32A C33A C30A 0.6(14) . . . . ?
C29A C30A C33A C32A 0.8(13) . . . . ?
C25B N3B C23B C24B 1(2) . . . . ?
N3B C23B C24B C27B -0.9(18) . . . . ?
C23B N3B C25B C26B -1(4) . . . . ?
N3B C25B C26B C27B 1(5) . . . . ?
C25B C26B C27B C24B 0(5) . . . . ?
C25B C26B C27B N9B -177(3) . . . . ?
C23B C24B C27B C26B 0(4) . . . . ?
C23B C24B C27B N9B 177(2) . . . . ?
C26B C27B N9B N10B -15(3) . . . . ?
C24B C27B N9B N10B 168(3) . . . . ?
C27B N9B N10B C28B -179.7(16) . . . . ?
N9B N10B C28B C29B 9(2) . . . . ?
N9B N10B C28B C31B -172(3) . . . . ?
C31B C28B C29B C30B 0(3) . . . . ?
N10B C28B C29B C30B 179.1(19) . . . . ?
C28B C29B C30B C33B 3(4) . . . . ?
C29B C28B C31B C32B -1(4) . . . . ?
N10B C28B C31B C32B 180(3) . . . . ?
C28B C31B C32B C33B 0(5) . . . . ?
C31B C32B C33B C30B 2(5) . . . . ?
C29B C30B C33B C32B -3(5) . . . . ?
C38 N11 N12 C39 178.2(3) . . . . ?
C36 N4 C34 C35 -0.8(7) . . . . ?
N4 C34 C35 C38 0.7(7) . . . . ?
C34 N4 C36 C37 0.4(7) . . . . ?
N4 C36 C37 C38 0.1(7) . . . . ?
C36 C37 C38 C35 -0.2(7) . . . . ?
C36 C37 C38 N11 179.0(4) . . . . ?
C34 C35 C38 C37 -0.2(6) . . . . ?
C34 C35 C38 N11 -179.3(4) . . . . ?
N12 N11 C38 C37 178.7(4) . . . . ?
N12 N11 C38 C35 -2.2(6) . . . . ?
N11 N12 C39 C42 -1.5(5) . . . . ?
N11 N12 C39 C40 179.1(4) . . . . ?
C42 C39 C40 C41 2.0(6) . . . . ?
N12 C39 C40 C41 -178.6(4) . . . . ?
C39 C40 C41 C44 -1.3(7) . . . . ?
C40 C39 C42 C43 -1.5(6) . . . . ?
N12 C39 C42 C43 179.2(4) . . . . ?
C39 C42 C43 C44 0.3(7) . . . . ?
C42 C43 C44 C41 0.4(8) . . . . ?
C40 C41 C44 C43 0.1(8) . . . . ?
C50 C45 C46 O1 179.6(3) . . . . ?
I1 C45 C46 O1 0.8(5) . . . . ?
C50 C45 C46 C47 0.8(5) . . . . ?
I1 C45 C46 C47 -178.0(3) . . . . ?
O1 C46 C47 C48 -179.9(4) . . . . ?
C45 C46 C47 C48 -1.2(6) . . . . ?
C46 C47 C48 O2 -178.5(4) . . . . ?
C46 C47 C48 C49 0.5(6) . . . . ?
O2 C48 C49 C50 179.6(3) . . . . ?
C47 C48 C49 C50 0.6(5) . . . . ?
O2 C48 C49 I2 0.4(5) . . . . ?
C47 C48 C49 I2 -178.6(3) . . . . ?
C48 C49 C50 C45 -1.0(5) . . . . ?
I2 C49 C50 C45 178.2(3) . . . . ?
C46 C45 C50 C49 0.3(5) . . . . ?
I1 C45 C50 C49 179.0(3) . . . . ?
C56 C51 C52 O3 178.5(3) . . . . ?
I3 C51 C52 O3 -2.4(5) . . . . ?
C56 C51 C52 C53 -0.3(5) . . . . ?
I3 C51 C52 C53 178.9(3) . . . . ?
O3 C52 C53 C54 179.4(3) . . . . ?
C51 C52 C53 C54 -1.9(6) . . . . ?
C52 C53 C54 O4 -178.3(3) . . . . ?
C52 C53 C54 C55 2.4(6) . . . . ?
O4 C54 C55 C56 179.9(3) . . . . ?
C53 C54 C55 C56 -0.8(5) . . . . ?
O4 C54 C55 I4 0.4(4) . . . . ?
C53 C54 C55 I4 179.7(3) . . . . ?
C52 C51 C56 C55 1.9(5) . . . . ?
I3 C51 C56 C55 -177.3(2) . . . . ?
C54 C55 C56 C51 -1.3(5) . . . . ?
I4 C55 C56 C51 178.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_pap_170
_database_code_depnum_ccdc_archive 'CCDC 1026678'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

__audit_creation_method          
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
  '4-pyridylazophenyl'
;
_chemical_name_common            '4PAzP 170'
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21

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'

_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'

loop_
_symmetry_equiv_pos_as_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                   5.9077(7)
_cell_length_b                   7.4479(9)
_cell_length_c                   21.752(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     957.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    5766
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9544
_exptl_absorpt_correction_T_max  0.9827
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7818
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2193
_reflns_number_gt                1339
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0612P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(4)
_refine_ls_number_reflns         2193
_refine_ls_number_parameters     255
_refine_ls_number_restraints     437
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002

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
N1A N 1.5506(4) 0.6609(5) 0.43934(10) 0.0574(8) Uani 0.881(3) 1 d PDU A 1
C1A C 1.6819(5) 0.5948(5) 0.39445(13) 0.0575(8) Uani 0.881(3) 1 d PDU A 1
H1A H 1.8251 0.5465 0.4054 0.069 Uiso 0.881(3) 1 calc PR A 1
C2A C 1.6208(4) 0.5927(4) 0.33298(11) 0.0503(7) Uani 0.881(3) 1 d PDU A 1
H2A H 1.7202 0.5454 0.3027 0.060 Uiso 0.881(3) 1 calc PR A 1
C3A C 1.3501(5) 0.7297(5) 0.42173(13) 0.0580(8) Uani 0.881(3) 1 d PDU A 1
H3A H 1.2547 0.7786 0.4526 0.070 Uiso 0.881(3) 1 calc PR A 1
C4A C 1.2741(5) 0.7340(4) 0.36195(12) 0.0516(7) Uani 0.881(3) 1 d PDU A 1
H4A H 1.1316 0.7854 0.3520 0.062 Uiso 0.881(3) 1 calc PR A 1
C5A C 1.4114(4) 0.6611(4) 0.31678(10) 0.0446(6) Uani 0.881(3) 1 d PDU A 1
N2A N 1.3546(3) 0.6498(3) 0.25250(8) 0.0536(6) Uani 0.881(3) 1 d PDU A 1
N3A N 1.1523(3) 0.6830(3) 0.24178(8) 0.0526(6) Uani 0.881(3) 1 d PDU A 1
C6A C 1.0918(4) 0.6688(3) 0.17847(10) 0.0454(6) Uani 0.881(3) 1 d PDU A 1
C7A C 1.2253(5) 0.5876(5) 0.13385(11) 0.0520(7) Uani 0.881(3) 1 d PDU A 1
H7A H 1.3672 0.5364 0.1446 0.062 Uiso 0.881(3) 1 calc PR A 1
C8A C 1.1502(6) 0.5819(6) 0.07375(11) 0.0584(8) Uani 0.881(3) 1 d PDU A 1
H8A H 1.2402 0.5257 0.0431 0.070 Uiso 0.881(3) 1 calc PR A 1
C9A C 0.8834(4) 0.7406(4) 0.16303(12) 0.0525(7) Uani 0.881(3) 1 d PDU A 1
H9A H 0.7896 0.7913 0.1940 0.063 Uiso 0.881(3) 1 calc PR A 1
C10A C 0.8114(5) 0.7385(5) 0.10201(12) 0.0569(8) Uani 0.881(3) 1 d PDU A 1
H10A H 0.6717 0.7926 0.0909 0.068 Uiso 0.881(3) 1 calc PR A 1
C11A C 0.9444(5) 0.6575(6) 0.05799(12) 0.0594(8) Uani 0.881(3) 1 d PDU A 1
H11A H 0.8944 0.6536 0.0165 0.071 Uiso 0.881(3) 1 calc PR A 1
N1B N 1.612(3) 0.643(4) 0.4304(8) 0.054(3) Uani 0.119(3) 1 d PDU A 2
C1B C 1.678(3) 0.589(3) 0.3743(9) 0.053(3) Uani 0.119(3) 1 d PDU A 2
H1B H 1.8199 0.5294 0.3708 0.064 Uiso 0.119(3) 1 calc PR A 2
C2B C 1.553(3) 0.616(3) 0.3214(7) 0.049(3) Uani 0.119(3) 1 d PDU A 2
H2B H 1.6098 0.5787 0.2826 0.059 Uiso 0.119(3) 1 calc PR A 2
C3B C 1.417(4) 0.737(4) 0.4325(6) 0.056(3) Uani 0.119(3) 1 d PDU A 2
H3B H 1.3734 0.7867 0.4708 0.067 Uiso 0.119(3) 1 calc PR A 2
C4B C 1.278(3) 0.765(3) 0.3827(6) 0.052(3) Uani 0.119(3) 1 d PDU A 2
H4B H 1.1404 0.8298 0.3870 0.063 Uiso 0.119(3) 1 calc PR A 2
C5B C 1.344(3) 0.698(3) 0.3262(5) 0.049(2) Uani 0.119(3) 1 d PDU A 2
N2B N 1.217(2) 0.718(2) 0.2702(5) 0.052(2) Uani 0.119(3) 1 d PDU A 2
N3B N 1.281(2) 0.621(2) 0.2276(5) 0.053(2) Uani 0.119(3) 1 d PDU A 2
C6B C 1.157(2) 0.6376(19) 0.1718(5) 0.049(2) Uani 0.119(3) 1 d PDU A 2
C7B C 1.232(3) 0.570(4) 0.1156(6) 0.051(3) Uani 0.119(3) 1 d PDU A 2
H7B H 1.3720 0.5077 0.1130 0.061 Uiso 0.119(3) 1 calc PR A 2
C8B C 1.102(4) 0.595(5) 0.0639(6) 0.055(3) Uani 0.119(3) 1 d PDU A 2
H8B H 1.1536 0.5515 0.0254 0.066 Uiso 0.119(3) 1 calc PR A 2
C9B C 0.957(3) 0.732(3) 0.1748(8) 0.051(3) Uani 0.119(3) 1 d PDU A 2
H9B H 0.9120 0.7856 0.2124 0.061 Uiso 0.119(3) 1 calc PR A 2
C10B C 0.819(3) 0.748(4) 0.1230(10) 0.052(3) Uani 0.119(3) 1 d PDU A 2
H10B H 0.6742 0.8018 0.1261 0.063 Uiso 0.119(3) 1 calc PR A 2
C11B C 0.897(4) 0.684(5) 0.0673(8) 0.056(3) Uani 0.119(3) 1 d PDU A 2
H11B H 0.8085 0.7010 0.0312 0.067 Uiso 0.119(3) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C1A 1.341(3) . ?
N1A C3A 1.346(3) . ?
C1A C2A 1.385(3) . ?
C1A H1A 0.9500 . ?
C2A C5A 1.384(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.376(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.385(3) . ?
C4A H4A 0.9500 . ?
C5A N2A 1.440(2) . ?
N2A N3A 1.242(2) . ?
N3A C6A 1.427(3) . ?
C6A C9A 1.383(3) . ?
C6A C7A 1.389(3) . ?
C7A C8A 1.381(3) . ?
C7A H7A 0.9500 . ?
C8A C11A 1.383(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.394(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.378(3) . ?
C10A H10A 0.9500 . ?
C11A H11A 0.9500 . ?
N1B C3B 1.344(8) . ?
N1B C1B 1.343(8) . ?
C1B C2B 1.383(8) . ?
C1B H1B 0.9500 . ?
C2B C5B 1.380(8) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.376(8) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.385(8) . ?
C4B H4B 0.9500 . ?
C5B N2B 1.440(7) . ?
N2B N3B 1.235(8) . ?
N3B C6B 1.422(7) . ?
C6B C9B 1.377(8) . ?
C6B C7B 1.392(8) . ?
C7B C8B 1.376(8) . ?
C7B H7B 0.9500 . ?
C8B C11B 1.383(8) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.394(8) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.378(8) . ?
C10B H10B 0.9500 . ?
C11B H11B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C3A 116.2(2) . . ?
N1A C1A C2A 123.8(2) . . ?
N1A C1A H1A 118.1 . . ?
C2A C1A H1A 118.1 . . ?
C5A C2A C1A 118.3(2) . . ?
C5A C2A H2A 120.8 . . ?
C1A C2A H2A 120.8 . . ?
N1A C3A C4A 124.4(2) . . ?
N1A C3A H3A 117.8 . . ?
C4A C3A H3A 117.8 . . ?
C3A C4A C5A 118.1(2) . . ?
C3A C4A H4A 121.0 . . ?
C5A C4A H4A 121.0 . . ?
C4A C5A C2A 119.2(2) . . ?
C4A C5A N2A 125.1(2) . . ?
C2A C5A N2A 115.7(2) . . ?
N3A N2A C5A 113.2(2) . . ?
N2A N3A C6A 114.0(2) . . ?
C9A C6A C7A 120.3(2) . . ?
C9A C6A N3A 115.4(2) . . ?
C7A C6A N3A 124.4(2) . . ?
C8A C7A C6A 119.5(2) . . ?
C8A C7A H7A 120.3 . . ?
C6A C7A H7A 120.3 . . ?
C7A C8A C11A 120.3(2) . . ?
C7A C8A H8A 119.9 . . ?
C11A C8A H8A 119.9 . . ?
C6A C9A C10A 119.9(2) . . ?
C6A C9A H9A 120.1 . . ?
C10A C9A H9A 120.1 . . ?
C11A C10A C9A 119.5(2) . . ?
C11A C10A H10A 120.2 . . ?
C9A C10A H10A 120.2 . . ?
C10A C11A C8A 120.5(2) . . ?
C10A C11A H11A 119.8 . . ?
C8A C11A H11A 119.8 . . ?
C3B N1B C1B 115.9(7) . . ?
N1B C1B C2B 123.8(7) . . ?
N1B C1B H1B 118.1 . . ?
C2B C1B H1B 118.1 . . ?
C5B C2B C1B 118.6(7) . . ?
C5B C2B H2B 120.7 . . ?
C1B C2B H2B 120.7 . . ?
N1B C3B C4B 124.4(7) . . ?
N1B C3B H3B 117.8 . . ?
C4B C3B H3B 117.8 . . ?
C3B C4B C5B 118.3(7) . . ?
C3B C4B H4B 120.9 . . ?
C5B C4B H4B 120.9 . . ?
C2B C5B C4B 118.7(6) . . ?
C2B C5B N2B 116.8(8) . . ?
C4B C5B N2B 124.4(8) . . ?
N3B N2B C5B 114.4(8) . . ?
N2B N3B C6B 115.6(8) . . ?
C9B C6B C7B 119.9(6) . . ?
C9B C6B N3B 116.4(7) . . ?
C7B C6B N3B 123.8(8) . . ?
C8B C7B C6B 119.4(7) . . ?
C8B C7B H7B 120.3 . . ?
C6B C7B H7B 120.3 . . ?
C7B C8B C11B 120.8(7) . . ?
C7B C8B H8B 119.6 . . ?
C11B C8B H8B 119.6 . . ?
C6B C9B C10B 120.4(7) . . ?
C6B C9B H9B 119.8 . . ?
C10B C9B H9B 119.8 . . ?
C11B C10B C9B 119.2(7) . . ?
C11B C10B H10B 120.4 . . ?
C9B C10B H10B 120.4 . . ?
C10B C11B C8B 120.1(7) . . ?
C10B C11B H11B 120.0 . . ?
C8B C11B H11B 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_pap290
_database_code_depnum_ccdc_archive 'CCDC 1026679'
_audit_update_record             
;
2015-03-05 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

__audit_creation_method          
;
SHELXL-97 and text editor.
;

_chemical_name_systematic        
; 
  '4-pyridylazophenyl'
;
_chemical_name_common            '4PAzP 290'
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21

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'

_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'

loop_
_symmetry_equiv_pos_as_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                   5.911(9)
_cell_length_b                   7.496(11)
_cell_length_c                   21.82(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     967(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1425
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.4

_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9549
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury2 (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7882
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2201
_reflns_number_gt                1214
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0690P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(5)
_refine_ls_number_reflns         2201
_refine_ls_number_parameters     254
_refine_ls_number_restraints     441
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003

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
N1A N -0.0504(5) 0.3389(5) 0.06068(11) 0.0629(9) Uani 0.869(4) 1 d PDU A 1
C1A C -0.1798(6) 0.4056(5) 0.10545(15) 0.0636(9) Uani 0.869(4) 1 d PDU A 1
H1A H -0.3189 0.4543 0.0947 0.076 Uiso 0.869(4) 1 calc PR A 1
C2A C -0.1199(5) 0.4069(5) 0.16687(13) 0.0559(8) Uani 0.869(4) 1 d PDU A 1
H2A H -0.2177 0.4525 0.1964 0.067 Uiso 0.869(4) 1 calc PR A 1
C3A C 0.1494(6) 0.2701(6) 0.07826(15) 0.0636(9) Uani 0.869(4) 1 d PDU A 1
H3A H 0.2427 0.2223 0.0481 0.076 Uiso 0.869(4) 1 calc PR A 1
C4A C 0.2251(6) 0.2659(5) 0.13788(14) 0.0578(8) Uani 0.869(4) 1 d PDU A 1
H4A H 0.3642 0.2154 0.1476 0.069 Uiso 0.869(4) 1 calc PR A 1
C5A C 0.0886(5) 0.3387(5) 0.18312(11) 0.0501(7) Uani 0.869(4) 1 d PDU A 1
N2A N 0.1465(4) 0.3511(3) 0.24719(9) 0.0599(7) Uani 0.869(4) 1 d PDU A 1
N3A N 0.3476(4) 0.3166(3) 0.25832(10) 0.0593(7) Uani 0.869(4) 1 d PDU A 1
C6A C 0.4076(5) 0.3307(4) 0.32154(12) 0.0504(7) Uani 0.869(4) 1 d PDU A 1
C7A C 0.2735(6) 0.4113(5) 0.36619(14) 0.0564(8) Uani 0.869(4) 1 d PDU A 1
H7A H 0.1350 0.4616 0.3556 0.068 Uiso 0.869(4) 1 calc PR A 1
C8A C 0.3476(5) 0.4161(6) 0.42643(14) 0.0638(9) Uani 0.869(4) 1 d PDU A 1
H8A H 0.2581 0.4688 0.4564 0.077 Uiso 0.869(4) 1 calc PR A 1
C9A C 0.6156(5) 0.2604(5) 0.33702(13) 0.0590(8) Uani 0.869(4) 1 d PDU A 1
H9A H 0.7078 0.2118 0.3068 0.071 Uiso 0.869(4) 1 calc PR A 1
C10A C 0.6879(6) 0.2622(6) 0.39798(15) 0.0638(9) Uani 0.869(4) 1 d PDU A 1
H10A H 0.8247 0.2096 0.4088 0.077 Uiso 0.869(4) 1 calc PR A 1
C11A C 0.5547(6) 0.3426(6) 0.44205(13) 0.0652(10) Uani 0.869(4) 1 d PDU A 1
H11A H 0.6043 0.3475 0.4825 0.078 Uiso 0.869(4) 1 calc PR A 1
N1B N -0.119(3) 0.358(4) 0.0698(8) 0.059(3) Uani 0.131(4) 1 d PDU A 2
C1B C -0.180(3) 0.414(3) 0.1257(10) 0.059(3) Uani 0.131(4) 1 d PDU A 2
H1B H -0.3183 0.4727 0.1295 0.070 Uiso 0.131(4) 1 calc PR A 2
C2B C -0.052(3) 0.391(3) 0.1782(7) 0.054(3) Uani 0.131(4) 1 d PDU A 2
H2B H -0.1038 0.4318 0.2160 0.064 Uiso 0.131(4) 1 calc PR A 2
C3B C 0.078(4) 0.270(4) 0.0672(6) 0.061(3) Uani 0.131(4) 1 d PDU A 2
H3B H 0.1235 0.2255 0.0293 0.073 Uiso 0.131(4) 1 calc PR A 2
C4B C 0.219(3) 0.242(4) 0.1165(6) 0.055(3) Uani 0.131(4) 1 d PDU A 2
H4B H 0.3537 0.1798 0.1119 0.066 Uiso 0.131(4) 1 calc PR A 2
C5B C 0.155(3) 0.307(4) 0.1733(6) 0.054(2) Uani 0.131(4) 1 d PDU A 2
N2B N 0.286(2) 0.289(2) 0.2287(5) 0.056(2) Uani 0.131(4) 1 d PDU A 2
N3B N 0.215(2) 0.375(2) 0.2728(5) 0.058(2) Uani 0.131(4) 1 d PDU A 2
C6B C 0.344(2) 0.362(2) 0.3276(5) 0.054(2) Uani 0.131(4) 1 d PDU A 2
C7B C 0.277(4) 0.439(4) 0.3832(7) 0.058(3) Uani 0.131(4) 1 d PDU A 2
H7B H 0.1401 0.4997 0.3860 0.069 Uiso 0.131(4) 1 calc PR A 2
C8B C 0.416(4) 0.423(4) 0.4338(7) 0.060(3) Uani 0.131(4) 1 d PDU A 2
H8B H 0.3791 0.4832 0.4698 0.072 Uiso 0.131(4) 1 calc PR A 2
C9B C 0.539(3) 0.264(3) 0.3248(8) 0.058(3) Uani 0.131(4) 1 d PDU A 2
H9B H 0.5800 0.2084 0.2883 0.069 Uiso 0.131(4) 1 calc PR A 2
C10B C 0.678(3) 0.246(4) 0.3763(11) 0.057(3) Uani 0.131(4) 1 d PDU A 2
H10B H 0.8156 0.1857 0.3736 0.068 Uiso 0.131(4) 1 calc PR A 2
C11B C 0.609(4) 0.319(5) 0.4313(8) 0.062(3) Uani 0.131(4) 1 d PDU A 2
H11B H 0.6924 0.2981 0.4667 0.075 Uiso 0.131(4) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C1A 1.337(4) . ?
N1A C3A 1.345(4) . ?
C1A C2A 1.386(4) . ?
C1A H1A 0.9300 . ?
C2A C5A 1.380(4) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.376(4) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.387(4) . ?
C4A H4A 0.9300 . ?
C5A N2A 1.442(3) . ?
N2A N3A 1.241(3) . ?
N3A C6A 1.428(4) . ?
C6A C9A 1.379(4) . ?
C6A C7A 1.394(4) . ?
C7A C8A 1.386(4) . ?
C7A H7A 0.9300 . ?
C8A C11A 1.385(4) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.397(4) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.382(4) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9300 . ?
N1B C1B 1.340(9) . ?
N1B C3B 1.341(9) . ?
C1B C2B 1.385(8) . ?
C1B H1B 0.9300 . ?
C2B C5B 1.377(9) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.376(8) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.386(8) . ?
C4B H4B 0.9300 . ?
C5B N2B 1.441(7) . ?
N2B N3B 1.232(9) . ?
N3B C6B 1.422(7) . ?
C6B C9B 1.373(9) . ?
C6B C7B 1.399(8) . ?
C7B C8B 1.381(8) . ?
C7B H7B 0.9300 . ?
C8B C11B 1.387(9) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.398(8) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.380(9) . ?
C10B H10B 0.9300 . ?
C11B H11B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C3A 115.9(2) . . ?
N1A C1A C2A 124.3(3) . . ?
N1A C1A H1A 117.9 . . ?
C2A C1A H1A 117.9 . . ?
C5A C2A C1A 118.3(3) . . ?
C5A C2A H2A 120.9 . . ?
C1A C2A H2A 120.9 . . ?
N1A C3A C4A 124.3(3) . . ?
N1A C3A H3A 117.8 . . ?
C4A C3A H3A 117.8 . . ?
C3A C4A C5A 118.3(3) . . ?
C3A C4A H4A 120.8 . . ?
C5A C4A H4A 120.8 . . ?
C4A C5A C2A 118.8(2) . . ?
C4A C5A N2A 125.3(3) . . ?
C2A C5A N2A 115.9(3) . . ?
N3A N2A C5A 113.8(2) . . ?
N2A N3A C6A 114.3(2) . . ?
C9A C6A C7A 120.1(3) . . ?
C9A C6A N3A 115.4(3) . . ?
C7A C6A N3A 124.5(3) . . ?
C8A C7A C6A 119.6(3) . . ?
C8A C7A H7A 120.2 . . ?
C6A C7A H7A 120.2 . . ?
C11A C8A C7A 120.2(3) . . ?
C11A C8A H8A 119.9 . . ?
C7A C8A H8A 119.9 . . ?
C6A C9A C10A 120.2(3) . . ?
C6A C9A H9A 119.9 . . ?
C10A C9A H9A 119.9 . . ?
C11A C10A C9A 119.5(3) . . ?
C11A C10A H10A 120.3 . . ?
C9A C10A H10A 120.3 . . ?
C10A C11A C8A 120.4(3) . . ?
C10A C11A H11A 119.8 . . ?
C8A C11A H11A 119.8 . . ?
C1B N1B C3B 115.4(7) . . ?
N1B C1B C2B 124.5(7) . . ?
N1B C1B H1B 117.8 . . ?
C2B C1B H1B 117.8 . . ?
C5B C2B C1B 118.6(7) . . ?
C5B C2B H2B 120.7 . . ?
C1B C2B H2B 120.7 . . ?
N1B C3B C4B 124.5(7) . . ?
N1B C3B H3B 117.8 . . ?
C4B C3B H3B 117.7 . . ?
C3B C4B C5B 118.7(7) . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B H4B 120.6 . . ?
C2B C5B C4B 118.2(6) . . ?
C2B C5B N2B 117.1(8) . . ?
C4B C5B N2B 124.6(8) . . ?
N3B N2B C5B 114.9(8) . . ?
N2B N3B C6B 116.1(8) . . ?
C9B C6B C7B 119.9(6) . . ?
C9B C6B N3B 116.7(8) . . ?
C7B C6B N3B 123.3(8) . . ?
C8B C7B C6B 119.4(7) . . ?
C8B C7B H7B 120.3 . . ?
C6B C7B H7B 120.3 . . ?
C7B C8B C11B 120.3(7) . . ?
C7B C8B H8B 119.8 . . ?
C11B C8B H8B 119.8 . . ?
C6B C9B C10B 120.7(7) . . ?
C6B C9B H9B 119.7 . . ?
C10B C9B H9B 119.7 . . ?
C11B C10B C9B 119.1(7) . . ?
C11B C10B H10B 120.5 . . ?
C9B C10B H10B 120.5 . . ?
C10B C11B C8B 120.2(7) . . ?
C10B C11B H11B 119.9 . . ?
C8B C11B H11B 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_dibr270
_database_code_depnum_ccdc_archive 'CCDC 1400641'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;

_audit_creation_method           
; 
SHELXL-97 and tex editor.
;

_chemical_name_systematic        
; 
 '4-pyridylazophenyl 4,6-dibromo-1,3-benzenediol' 
;
_chemical_name_common            '4PAzP.4,6-diBr res 270'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C11 H9 N3), C6 H4 Br2 O2'
_chemical_formula_sum            'C28 H22 Br2 N6 O2'
_chemical_formula_weight         634.34

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.5204(15)
_cell_length_b                   20.207(2)
_cell_length_c                   9.4966(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.176(5)
_cell_angle_gamma                90.00
_cell_volume                     2764.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    8843
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      21.79

_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_absorpt_coefficient_mu    2.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.269
_exptl_absorpt_correction_T_max  0.680
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            62803
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         24.72
_reflns_number_total             4217
_reflns_number_gt                2616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0000P)²+5.1943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4217
_refine_ls_number_parameters     470
_refine_ls_number_restraints     429
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.254
_refine_ls_restrained_S_all      1.207
_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
Br1 Br 0.17756(4) 0.23453(3) 0.12592(7) 0.0817(2) Uani 1 1 d . . .
O1 O 0.2315(2) 0.03021(19) 0.5888(4) 0.0772(11) Uani 1 1 d . . .
H1 H 0.1873 0.0298 0.6347 0.116 Uiso 1 1 calc R . .
C1 C 0.1920(3) 0.1683(3) 0.2668(5) 0.0556(14) Uani 1 1 d . . .
Br2 Br 0.38966(4) 0.02937(4) 0.41135(8) 0.0987(3) Uani 1 1 d . . .
O2 O 0.0447(2) 0.19594(19) 0.3308(4) 0.0759(11) Uani 1 1 d . . .
H2 H 0.0097 0.1857 0.3886 0.114 Uiso 1 1 calc R . .
C2 C 0.2707(3) 0.1298(3) 0.2851(6) 0.0616(15) Uani 1 1 d . . .
H2A H 0.3163 0.1354 0.2255 0.074 Uiso 1 1 calc R . .
C3 C 0.2820(3) 0.0835(3) 0.3904(6) 0.0576(14) Uani 1 1 d . . .
C4 C 0.2161(4) 0.0749(3) 0.4831(6) 0.0587(14) Uani 1 1 d . . .
C5 C 0.1367(3) 0.1129(3) 0.4616(6) 0.0581(15) Uani 1 1 d . . .
H5A H 0.0911 0.1072 0.5211 0.070 Uiso 1 1 calc R . .
C6 C 0.1232(3) 0.1592(3) 0.3539(6) 0.0550(14) Uani 1 1 d . . .
C11 C 0.0629(4) -0.0179(3) 1.1995(7) 0.0802(18) Uani 1 1 d . . .
H11A H 0.1160 0.0080 1.2180 0.096 Uiso 1 1 calc R . .
C12 C -0.0136(5) -0.0051(3) 1.2678(6) 0.0835(19) Uani 1 1 d . . .
H12A H -0.0105 0.0298 1.3322 0.100 Uiso 1 1 calc R . .
N13 N -0.0913(3) -0.0401(3) 1.2461(6) 0.0787(15) Uani 1 1 d . . .
C14 C -0.0934(5) -0.0881(4) 1.1528(8) 0.098(2) Uani 1 1 d . . .
H14A H -0.1478 -0.1125 1.1341 0.117 Uiso 1 1 calc R . .
C15 C -0.0199(4) -0.1046(3) 1.0806(7) 0.092(2) Uani 1 1 d . . .
H15A H -0.0246 -0.1396 1.0165 0.110 Uiso 1 1 calc R . .
C16 C 0.0603(4) -0.0683(3) 1.1054(6) 0.0678(16) Uani 1 1 d . . .
N17 N 0.1340(3) -0.0874(2) 1.0275(5) 0.0746(14) Uani 1 1 d . . .
N18 N 0.1985(3) -0.0477(2) 1.0373(5) 0.0719(14) Uani 1 1 d . . .
C19 C 0.2722(4) -0.0660(3) 0.9598(6) 0.0676(16) Uani 1 1 d . . .
C20 C 0.2794(5) -0.1260(4) 0.8997(7) 0.096(2) Uani 1 1 d . . .
H20A H 0.2345 -0.1580 0.9086 0.115 Uiso 1 1 calc R . .
C21 C 0.3528(6) -0.1401(4) 0.8252(8) 0.120(3) Uani 1 1 d . . .
H21A H 0.3574 -0.1817 0.7849 0.144 Uiso 1 1 calc R . .
C22 C 0.4179(5) -0.0937(5) 0.8105(8) 0.102(2) Uani 1 1 d . . .
H22A H 0.4667 -0.1029 0.7588 0.122 Uiso 1 1 calc R . .
C23 C 0.4116(5) -0.0342(5) 0.8713(9) 0.115(3) Uani 1 1 d . . .
H23A H 0.4565 -0.0023 0.8617 0.138 Uiso 1 1 calc R . .
C24 C 0.3389(5) -0.0197(4) 0.9484(8) 0.109(2) Uani 1 1 d . . .
H24A H 0.3358 0.0213 0.9920 0.130 Uiso 1 1 calc R . .
C31' C 0.7692(10) 0.1247(9) 0.5151(19) 0.071(4) Uani 0.552(10) 1 d PDU A 2
H31' H 0.7267 0.0937 0.4742 0.085 Uiso 0.552(10) 1 calc PR A 2
C32' C 0.8537(12) 0.1341(12) 0.462(2) 0.076(4) Uani 0.552(10) 1 d PDU A 2
H32' H 0.8649 0.1095 0.3833 0.092 Uiso 0.552(10) 1 calc PR A 2
N33' N 0.9188(11) 0.1754(12) 0.517(2) 0.067(4) Uani 0.552(10) 1 d PDU A 2
C34' C 0.9006(11) 0.2093(11) 0.630(2) 0.066(3) Uani 0.552(10) 1 d PDU A 2
H34' H 0.9454 0.2384 0.6727 0.080 Uiso 0.552(10) 1 calc PR A 2
C35' C 0.8172(11) 0.2035(9) 0.6890(17) 0.065(4) Uani 0.552(10) 1 d PDU A 2
H35' H 0.8080 0.2278 0.7692 0.078 Uiso 0.552(10) 1 calc PR A 2
C36' C 0.7499(8) 0.1622(8) 0.6285(16) 0.057(3) Uani 0.552(10) 1 d PDU A 2
N37' N 0.6609(6) 0.1551(6) 0.6758(12) 0.071(3) Uani 0.552(10) 1 d PDU A 2
N38' N 0.6446(6) 0.1936(5) 0.7670(11) 0.070(3) Uani 0.552(10) 1 d PDU A 2
C39' C 0.5542(7) 0.1901(8) 0.8087(18) 0.060(3) Uani 0.552(10) 1 d PDU A 2
C40' C 0.4931(10) 0.1421(8) 0.7566(18) 0.073(4) Uani 0.552(10) 1 d PDU A 2
H40' H 0.5118 0.1103 0.6954 0.087 Uiso 0.552(10) 1 calc PR A 2
C41' C 0.4032(9) 0.1400(9) 0.793(2) 0.091(4) Uani 0.552(10) 1 d PDU A 2
H41' H 0.3619 0.1074 0.7563 0.109 Uiso 0.552(10) 1 calc PR A 2
C42' C 0.3766(10) 0.1861(12) 0.884(3) 0.092(4) Uani 0.552(10) 1 d PDU A 2
H42' H 0.3168 0.1845 0.9097 0.110 Uiso 0.552(10) 1 calc PR A 2
C43' C 0.4357(11) 0.2346(11) 0.939(2) 0.094(4) Uani 0.552(10) 1 d PDU A 2
H43' H 0.4164 0.2656 1.0010 0.113 Uiso 0.552(10) 1 calc PR A 2
C44' C 0.5255(9) 0.2376(8) 0.9002(18) 0.085(4) Uani 0.552(10) 1 d PDU A 2
H44' H 0.5658 0.2712 0.9356 0.101 Uiso 0.552(10) 1 calc PR A 2
C31 C 0.7598(12) 0.1344(11) 0.557(2) 0.067(4) Uani 0.448(10) 1 d PDU A 1
H31 H 0.7059 0.1096 0.5362 0.081 Uiso 0.448(10) 1 calc PR A 1
C32 C 0.8328(16) 0.1280(15) 0.475(3) 0.072(4) Uani 0.448(10) 1 d PDU A 1
H32 H 0.8265 0.0970 0.4019 0.087 Uiso 0.448(10) 1 calc PR A 1
N33 N 0.9098(14) 0.1630(15) 0.494(3) 0.068(4) Uani 0.448(10) 1 d PDU A 1
C34 C 0.9186(12) 0.2037(15) 0.606(3) 0.071(4) Uani 0.448(10) 1 d PDU A 1
H34 H 0.9739 0.2270 0.6262 0.085 Uiso 0.448(10) 1 calc PR A 1
C35 C 0.8491(11) 0.2131(11) 0.693(2) 0.062(4) Uani 0.448(10) 1 d PDU A 1
H35 H 0.8576 0.2432 0.7674 0.075 Uiso 0.448(10) 1 calc PR A 1
C36 C 0.7689(8) 0.1778(10) 0.6683(19) 0.058(4) Uani 0.448(10) 1 d PDU A 1
N37 N 0.6927(6) 0.1880(6) 0.7475(13) 0.064(3) Uani 0.448(10) 1 d PDU A 1
N38 N 0.6218(7) 0.1598(7) 0.7011(15) 0.066(4) Uani 0.448(10) 1 d PDU A 1
C39 C 0.5435(8) 0.1725(10) 0.773(2) 0.060(4) Uani 0.448(10) 1 d PDU A 1
C40 C 0.4615(10) 0.1405(10) 0.730(2) 0.079(5) Uani 0.448(10) 1 d PDU A 1
H40 H 0.4593 0.1082 0.6600 0.095 Uiso 0.448(10) 1 calc PR A 1
C41 C 0.3815(10) 0.1555(11) 0.791(3) 0.091(5) Uani 0.448(10) 1 d PDU A 1
H41 H 0.3258 0.1343 0.7596 0.109 Uiso 0.448(10) 1 calc PR A 1
C42 C 0.3857(12) 0.2015(15) 0.896(4) 0.090(4) Uani 0.448(10) 1 d PDU A 1
H42 H 0.3329 0.2104 0.9386 0.108 Uiso 0.448(10) 1 calc PR A 1
C43 C 0.4657(14) 0.2348(14) 0.939(3) 0.095(4) Uani 0.448(10) 1 d PDU A 1
H43 H 0.4665 0.2679 1.0072 0.114 Uiso 0.448(10) 1 calc PR A 1
C44 C 0.5468(11) 0.2189(10) 0.881(2) 0.076(4) Uani 0.448(10) 1 d PDU A 1
H44 H 0.6027 0.2393 0.9145 0.091 Uiso 0.448(10) 1 calc PR A 1


_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
Br1 C1 1.885(5) . ?
O1 C4 1.348(6) . ?
C1 C2 1.376(7) . ?
C1 C6 1.387(6) . ?
Br2 C3 1.897(5) . ?
O2 C6 1.354(5) . ?
C2 C3 1.366(7) . ?
C3 C4 1.390(6) . ?
C4 C5 1.379(7) . ?
C5 C6 1.382(7) . ?
C11 C16 1.353(8) . ?
C11 C12 1.379(7) . ?
C12 N13 1.327(7) . ?
N13 C14 1.311(8) . ?
C14 C15 1.379(8) . ?
C15 C16 1.370(7) . ?
C16 N17 1.428(7) . ?
N17 N18 1.228(6) . ?
N18 C19 1.422(7) . ?
C19 C20 1.349(8) . ?
C19 C24 1.359(8) . ?
C20 C21 1.381(8) . ?
C21 C22 1.351(9) . ?
C22 C23 1.341(9) . ?
C23 C24 1.390(9) . ?
C31' C36' 1.373(11) . ?
C31' C32' 1.395(11) . ?
C32' N33' 1.317(10) . ?
N33' C34' 1.332(10) . ?
C34' C35' 1.399(11) . ?
C35' C36' 1.357(11) . ?
C36' N37' 1.427(10) . ?
N37' N38' 1.210(8) . ?
N38' C39' 1.419(9) . ?
C39' C40' 1.365(11) . ?
C39' C44' 1.393(11) . ?
C40' C41' 1.394(11) . ?
C41' C42' 1.357(12) . ?
C42' C43' 1.361(12) . ?
C43' C44' 1.399(12) . ?
C31 C36 1.367(12) . ?
C31 C32 1.398(11) . ?
C32 N33 1.317(10) . ?
N33 C34 1.332(11) . ?
C34 C35 1.397(11) . ?
C35 C36 1.361(11) . ?
C36 N37 1.429(10) . ?
N37 N38 1.211(9) . ?
N38 C39 1.419(10) . ?
C39 C40 1.371(12) . ?
C39 C44 1.386(12) . ?
C40 C41 1.392(11) . ?
C41 C42 1.358(12) . ?
C42 C43 1.361(12) . ?
C43 C44 1.400(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.9(5) . . ?
C2 C1 Br1 120.5(4) . . ?
C6 C1 Br1 119.5(4) . . ?
C3 C2 C1 120.2(5) . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 Br2 119.6(4) . . ?
C4 C3 Br2 119.1(4) . . ?
O1 C4 C5 122.8(5) . . ?
O1 C4 C3 119.4(5) . . ?
C5 C4 C3 117.8(5) . . ?
C4 C5 C6 121.7(5) . . ?
O2 C6 C5 122.0(4) . . ?
O2 C6 C1 119.0(5) . . ?
C5 C6 C1 119.0(5) . . ?
C16 C11 C12 119.6(6) . . ?
N13 C12 C11 123.2(6) . . ?
C14 N13 C12 116.5(6) . . ?
N13 C14 C15 124.1(6) . . ?
C16 C15 C14 118.6(6) . . ?
C11 C16 C15 118.0(6) . . ?
C11 C16 N17 125.8(6) . . ?
C15 C16 N17 116.2(6) . . ?
N18 N17 C16 113.5(5) . . ?
N17 N18 C19 114.1(5) . . ?
C20 C19 C24 119.4(6) . . ?
C20 C19 N18 123.7(6) . . ?
C24 C19 N18 116.9(6) . . ?
C19 C20 C21 120.5(7) . . ?
C22 C21 C20 120.3(7) . . ?
C23 C22 C21 119.4(7) . . ?
C22 C23 C24 120.8(7) . . ?
C19 C24 C23 119.5(7) . . ?
C36' C31' C32' 118.9(8) . . ?
N33' C32' C31' 124.3(8) . . ?
C32' N33' C34' 116.1(8) . . ?
N33' C34' C35' 123.2(8) . . ?
C36' C35' C34' 119.7(8) . . ?
C35' C36' C31' 117.6(8) . . ?
C35' C36' N37' 124.1(10) . . ?
C31' C36' N37' 118.2(10) . . ?
N38' N37' C36' 115.2(7) . . ?
N37' N38' C39' 116.0(7) . . ?
C40' C39' C44' 118.9(8) . . ?
C40' C39' N38' 121.1(10) . . ?
C44' C39' N38' 120.0(10) . . ?
C39' C40' C41' 121.2(9) . . ?
C42' C41' C40' 119.2(9) . . ?
C41' C42' C43' 121.3(9) . . ?
C42' C43' C44' 119.8(9) . . ?
C39' C44' C43' 119.6(9) . . ?
C36 C31 C32 119.0(9) . . ?
N33 C32 C31 124.1(9) . . ?
C32 N33 C34 116.0(8) . . ?
N33 C34 C35 123.3(9) . . ?
C36 C35 C34 119.6(9) . . ?
C35 C36 C31 117.8(8) . . ?
C35 C36 N37 122.5(11) . . ?
C31 C36 N37 119.6(11) . . ?
N38 N37 C36 114.8(8) . . ?
N37 N38 C39 115.8(8) . . ?
C40 C39 C44 119.0(8) . . ?
C40 C39 N38 119.5(11) . . ?
C44 C39 N38 121.4(10) . . ?
C39 C40 C41 121.0(9) . . ?
C42 C41 C40 119.3(9) . . ?
C41 C42 C43 121.2(9) . . ?
C42 C43 C44 119.7(10) . . ?
C39 C44 C43 119.7(9) . . ?

_diffrn_measured_fraction_theta_max 0.893
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_full 'ACTA 50'
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.061

# start Validation Reply Form
_vrf_PLAT037_I                   
;
PROBLEM: _diffrn_reflns_theta_full .......... Not Given .     Please Do ! 
RESPONSE: This was the highest quality crystal we could locate.  The solution is correct.
;
_vrf_PLAT039_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full Not Given .     Please Do ! 
RESPONSE: This was the highest quality crystal we could locate.  The solution is correct.
;
# end Validation Reply Form
