Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350

_publ_section_title              
;Synthesis and inclusion properties of new nitrated
C2-symmetric diquinoline hosts
;
_publ_contact_author_name        'Prof. Roger Bishop'
_publ_contact_author_email       R.BISHOP@UNSW.EDU.AU
loop_
_publ_author_name
'Roger Bishop'
'Jason Ashmore'
'Donald C. Craig'
'Marcia Scudder'

# Attachment 'drb307.cif'

data_DRB307
_database_code_depnum_ccdc_archive 'CCDC 668451'
_audit_creation_method           'RAELSPUB and manual entry'

_publ_section_references         
; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G., Giacovazzo, C.,
Guagliardi, A., Polidori, G., J. Appl. Cryst., 1994, 27, 435.

Ibers, J.A. and Hamilton, W.C., (Eds) International Tables for X-Ray
Crystallography Vol. 4 , Kynoch Press, Birmingham, 1974.

Johnson, C.K.,'ORTEP-II', Oak Ridge National Laboratory, Tennessee,
U.S.A., 1976.

Rae, A.D., RAELS. A comprehensive Constrained Least Squares Refinement
Program, University of New South Wales, 1989.

Schagen, J.D., Straver, L., van Meurs, F., Williams, G.,
CAD4 Version 5.0, Delft Instruments X-ray Diffraction, 1989.
;

_publ_section_figure_captions    ?
_publ_section_exptl_prep         ?
_publ_section_exptl_refinement   ?
_computing_data_collection       'CAD4 Version 5.0, (Schagen et al, 1989)'
_computing_cell_refinement       'CAD4 Version 5.0, (Schagen et al, 1989)'
_computing_data_reduction        'Local program'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'RAELS, (Rae, 1996)'
_computing_molecular_graphics    'ORTEP-II, (Johnson, 1976)'
_computing_publication_material  'Local programs'

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C23 H16 N4 O4),C D Cl3'
_chemical_formula_sum            'C47 H32 Cl3 D N8 O8'
_chemical_formula_iupac          ?
_chemical_formula_weight         945.2

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   11.648(2)
_cell_length_b                   13.351(2)
_cell_length_c                   14.481(2)
_cell_angle_alpha                81.68(1)
_cell_angle_beta                 89.47(1)
_cell_angle_gamma                69.17(1)
_cell_volume                     2080.5(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10
_cell_measurement_theta_min      10
_cell_measurement_theta_max      11
_cell_measurement_temperature    294
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.51
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             974.0
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       \w--2\q
_diffrn_reflns_number            6053
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_theta_max         23
_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        23
_diffrn_measured_fraction_theta_full 1.00
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         1
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        4

# REFINEMENT DATA

_refine_special_details          ?
_reflns_number_total             5781
_reflns_number_gt                4426
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.052
_refine_ls_wR_factor_ref         0.073
_refine_ls_abs_structure_Flack   ?
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         4426
_refine_ls_number_parameters     311
_refine_ls_goodness_of_fit_ref   1.75
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[\s^2^(F) + 0.0004F^2^]'
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_atom_type_scat_source           
'International Tables for X-ray Crystallography, Vol. IV'

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
_atom_site_occupancy
O1A 0.4758(3) 0.5817(2) 0.9158(2) 0.0602(8) Uani O 1.0
O2A 0.5443(3) 0.7011(3) 0.8472(2) 0.0710(9) Uani O 1.0
O3A 0.0226(3) 0.6407(3) 0.1961(2) 0.082(1) Uani O 1.0
O4A -0.1507(3) 0.7108(3) 0.2568(2) 0.0711(9) Uani O 1.0
N1A 0.3437(3) 0.5857(2) 0.7441(2) 0.0379(4) Uani N 1.0
N2A 0.0238(3) 0.6846(2) 0.4288(2) 0.0399(4) Uani N 1.0
N3A 0.5219(3) 0.6182(3) 0.8503(2) 0.0453(8) Uani N 1.0
N4A -0.0464(3) 0.7065(3) 0.2397(2) 0.0480(8) Uani N 1.0
C1A 0.1279(3) 0.6358(3) 0.7141(2) 0.0399(6) Uani C 1.0
C2A 0.2588(3) 0.5692(3) 0.6950(2) 0.0373(5) Uani C 1.0
C3A 0.2846(3) 0.5009(3) 0.6252(2) 0.0392(4) Uani C 1.0
C4A 0.1820(3) 0.4841(3) 0.5739(2) 0.0425(5) Uani C 1.0
C5A 0.0561(3) 0.5740(3) 0.5799(2) 0.0419(5) Uani C 1.0
C6A 0.0516(3) 0.6775(3) 0.5188(2) 0.0383(4) Uani C 1.0
C7A 0.0805(3) 0.7584(3) 0.5570(2) 0.0380(4) Uani C 1.0
C8A 0.0969(3) 0.7519(3) 0.6616(2) 0.0398(5) Uani C 1.0
C9A 0.0361(3) 0.5885(3) 0.6825(2) 0.0449(7) Uani C 1.0
C10A 0.4631(3) 0.5366(3) 0.7238(2) 0.0403(4) Uani C 1.0
C11A 0.5556(3) 0.5559(3) 0.7720(2) 0.0445(4) Uani C 1.0
C12A 0.6760(3) 0.5190(3) 0.7488(3) 0.0521(6) Uani C 1.0
C13A 0.7098(4) 0.4552(4) 0.6777(3) 0.0567(9) Uani C 1.0
C14A 0.6255(3) 0.4292(3) 0.6320(3) 0.0526(7) Uani C 1.0
C15A 0.4993(3) 0.4706(3) 0.6526(2) 0.0437(4) Uani C 1.0
C16A 0.4054(3) 0.4525(3) 0.6051(2) 0.0428(4) Uani C 1.0
C17A 0.0271(3) 0.7737(3) 0.3700(2) 0.0410(4) Uani C 1.0
C18A -0.0031(3) 0.7860(3) 0.2739(2) 0.0455(6) Uani C 1.0
C19A 0.0050(4) 0.8686(3) 0.2105(3) 0.0512(8) Uani C 1.0
C20A 0.0434(4) 0.9475(3) 0.2416(3) 0.0545(8) Uani C 1.0
C21A 0.0730(4) 0.9396(3) 0.3334(3) 0.0503(6) Uani C 1.0
C22A 0.0640(3) 0.8534(3) 0.4003(2) 0.0425(4) Uani C 1.0
C23A 0.0904(3) 0.8432(3) 0.4967(2) 0.0408(4) Uani C 1.0
O1B 0.5793(3) 0.2810(3) 0.4606(2) 0.0746(9) Uani O 1.0
O2B 0.6412(3) 0.1694(3) 0.3644(3) 0.089(1) Uani O 1.0
O3B 0.0778(3) 0.1701(3) 1.0188(2) 0.0723(9) Uani O 1.0
O4B 0.1127(3) 0.1957(3) 1.1573(2) 0.0767(9) Uani O 1.0
N1B 0.5176(3) 0.1257(2) 0.5965(2) 0.0392(4) Uani N 1.0
N2B 0.3107(3) 0.1624(2) 0.9485(2) 0.0390(4) Uani N 1.0
N3B 0.5687(3) 0.2126(3) 0.4194(2) 0.0495(8) Uani N 1.0
N4B 0.1164(3) 0.2136(3) 1.0721(2) 0.0504(8) Uani N 1.0
C1B 0.5877(3) 0.0688(3) 0.7571(2) 0.0405(4) Uani C 1.0
C2B 0.4938(3) 0.0847(3) 0.6799(2) 0.0371(4) Uani C 1.0
C3B 0.3863(3) 0.0596(3) 0.6988(2) 0.0380(4) Uani C 1.0
C4B 0.3664(3) 0.0099(3) 0.7954(2) 0.0418(4) Uani C 1.0
C5B 0.4486(3) 0.0217(3) 0.8717(2) 0.0411(5) Uani C 1.0
C6B 0.4037(3) 0.1373(3) 0.8920(2) 0.0374(4) Uani C 1.0
C7B 0.4593(3) 0.2117(3) 0.8529(2) 0.0385(4) Uani C 1.0
C8B 0.5681(3) 0.1774(3) 0.7907(2) 0.0421(4) Uani C 1.0
C9B 0.5808(3) -0.0134(3) 0.8398(2) 0.0440(6) Uani C 1.0
C10B 0.4357(3) 0.1426(3) 0.5245(2) 0.0407(4) Uani C 1.0
C11B 0.4600(4) 0.1820(3) 0.4338(2) 0.0468(7) Uani C 1.0
C12B 0.3856(4) 0.1937(3) 0.3566(2) 0.053(1) Uani C 1.0
C13B 0.2796(4) 0.1689(3) 0.3694(3) 0.0548(9) Uani C 1.0
C14B 0.2497(3) 0.1322(3) 0.4557(3) 0.0508(7) Uani C 1.0
C15B 0.3279(3) 0.1175(3) 0.5357(2) 0.0425(4) Uani C 1.0
C16B 0.3054(3) 0.0763(3) 0.6256(2) 0.0417(4) Uani C 1.0
C17B 0.2662(3) 0.2648(3) 0.9696(2) 0.0393(4) Uani C 1.0
C18B 0.1705(3) 0.2938(3) 1.0332(2) 0.0433(7) Uani C 1.0
C19B 0.1269(3) 0.3936(3) 1.0610(2) 0.0468(9) Uani C 1.0
C20B 0.1740(4) 0.4734(3) 1.0221(3) 0.0498(8) Uani C 1.0
C21B 0.2655(4) 0.4498(3) 0.9608(3) 0.0482(6) Uani C 1.0
C22B 0.3144(3) 0.3453(3) 0.9342(2) 0.0414(4) Uani C 1.0
C23B 0.4140(3) 0.3146(3) 0.8747(2) 0.0419(4) Uani C 1.0
C1Ch 0.26573(43) 0.80031(10) 0.97897(6) 0.0636(5) Uani C 1.0
Cl1Ch 0.19698(12) 0.93262(8) 1.00160(6) 0.0728(5) Uani Cl 1.0
Cl2Ch 0.24834(13) 0.70799(8) 1.07077(7) 0.0813(7) Uani Cl 1.0
Cl3Ch 0.20767(13) 0.78441(9) 0.87404(7) 0.0924(9) Uani Cl 1.0
HC1A 0.1214 0.6385 0.7827 0.043 Uani H 1.0
H1C4A 0.1766 0.4130 0.6018 0.049 Uani H 1.0
H2C4A 0.2018 0.4827 0.5067 0.043 Uani H 1.0
HC5A -0.0095 0.5505 0.5568 0.047 Uani H 1.0
H1C8A 0.0188 0.8001 0.6853 0.045 Uani H 1.0
H2C8A 0.1653 0.7775 0.6744 0.040 Uani H 1.0
H1C9A -0.0497 0.6391 0.6892 0.049 Uani H 1.0
H2C9A 0.0494 0.5168 0.7215 0.050 Uani H 1.0
HC12A 0.7388 0.5374 0.7823 0.058 Uani H 1.0
HC13A 0.7976 0.4282 0.6602 0.066 Uani H 1.0
HC14A 0.6525 0.3804 0.5835 0.059 Uani H 1.0
HC16A 0.4268 0.4037 0.5563 0.048 Uani H 1.0
HC19A -0.0160 0.8734 0.1428 0.056 Uani H 1.0
HC20A 0.0488 1.0093 0.1960 0.063 Uani H 1.0
HC21A 0.1017 0.9951 0.3546 0.056 Uani H 1.0
HC23A 0.1165 0.8986 0.5212 0.045 Uani H 1.0
HC1B 0.6716 0.0417 0.7318 0.045 Uani H 1.0
H1C4B 0.3839 -0.0690 0.7954 0.048 Uani H 1.0
H2C4B 0.2786 0.0462 0.8102 0.044 Uani H 1.0
HC5B 0.4455 -0.0275 0.9299 0.047 Uani H 1.0
H1C8B 0.6440 0.1707 0.8267 0.048 Uani H 1.0
H2C8B 0.5536 0.2346 0.7348 0.044 Uani H 1.0
H1C9B 0.6377 -0.0160 0.8922 0.049 Uani H 1.0
H2C9B 0.6049 -0.0868 0.8205 0.048 Uani H 1.0
HC12B 0.4073 0.2193 0.2929 0.059 Uani H 1.0
HC13B 0.2241 0.1783 0.3140 0.063 Uani H 1.0
HC14B 0.1727 0.1155 0.4630 0.058 Uani H 1.0
HC16B 0.2292 0.0589 0.6363 0.048 Uani H 1.0
HC19B 0.0624 0.4100 1.1084 0.051 Uani H 1.0
HC20B 0.1398 0.5478 1.0397 0.057 Uani H 1.0
HC21B 0.2987 0.5068 0.9343 0.055 Uani H 1.0
HC23B 0.4516 0.3687 0.8483 0.048 Uani H 1.0
DC1Ch 0.3557 0.7853 0.9730 0.065 Uani D 1.0
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
O1A 0.071(2) 0.078(2) 0.036(2) -0.032(2) 0.010(1) -0.004(1) O
O2A 0.105(3) 0.065(2) 0.054(2) -0.043(2) 0.010(2) -0.009(2) O
O3A 0.095(3) 0.073(2) 0.087(2) -0.031(2) 0.030(2) -0.044(2) O
O4A 0.058(2) 0.080(2) 0.081(2) -0.031(2) 0.000(2) -0.017(2) O
N1A 0.0445(5) 0.0353(6) 0.0324(5) -0.0132(4) 0.0045(3) -0.0036(4) N
N2A 0.0448(5) 0.0410(6) 0.0339(5) -0.0157(4) 0.0039(4) -0.0046(4) N
N3A 0.048(2) 0.049(2) 0.035(2) -0.015(2) -0.002(2) 0.000(2) N
N4A 0.058(2) 0.047(2) 0.033(2) -0.016(2) -0.003(2) 0.001(2) N
C1A 0.0444(5) 0.0426(8) 0.0325(5) -0.0158(4) 0.0066(4) -0.0046(4) C
C2A 0.0451(5) 0.0333(7) 0.0327(5) -0.0139(4) 0.0048(3) -0.0030(4) C
C3A 0.0496(6) 0.0302(7) 0.0362(5) -0.0130(4) 0.0030(4) -0.0035(4) C
C4A 0.0564(7) 0.0341(7) 0.0390(7) -0.0194(5) 0.0016(5) -0.0034(4) C
C5A 0.0497(5) 0.0435(7) 0.0358(6) -0.0220(5) 0.0040(4) -0.0026(5) C
C6A 0.0428(5) 0.0380(6) 0.0334(5) -0.0142(4) 0.0051(3) -0.0046(4) C
C7A 0.0427(6) 0.0338(6) 0.0342(5) -0.0096(5) 0.0052(4) -0.0057(4) C
C8A 0.0438(6) 0.0379(7) 0.0345(5) -0.0096(5) 0.0064(4) -0.0081(5) C
C9A 0.0490(5) 0.053(1) 0.0352(6) -0.0239(6) 0.0056(4) -0.0017(6) C
C10A 0.0441(5) 0.0381(6) 0.0349(5) -0.0110(4) 0.0032(3) -0.0035(4) C
C11A 0.0450(6) 0.0495(8) 0.0363(5) -0.0146(5) 0.0021(4) -0.0036(4) C
C12A 0.0441(6) 0.066(1) 0.0409(8) -0.0142(6) 0.0013(5) -0.0043(7) C
C13A 0.0433(6) 0.069(1) 0.0452(9) -0.0059(5) 0.0023(4) -0.0078(8) C
C14A 0.0462(7) 0.0539(8) 0.0448(8) -0.0015(5) 0.0025(4) -0.0094(6) C
C15A 0.0461(6) 0.0384(6) 0.0391(5) -0.0061(4) 0.0027(4) -0.0058(4) C
C16A 0.0509(6) 0.0318(7) 0.0399(5) -0.0073(4) 0.0022(4) -0.0063(4) C
C17A 0.0458(5) 0.0403(6) 0.0342(5) -0.0132(4) 0.0027(4) -0.0027(4) C
C18A 0.0499(7) 0.050(1) 0.0346(5) -0.0167(6) 0.0010(4) -0.0015(4) C
C19A 0.058(1) 0.055(1) 0.0368(5) -0.0193(8) -0.0021(5) 0.0041(5) C
C20A 0.067(1) 0.050(1) 0.0423(6) -0.0207(8) -0.0054(6) 0.0089(7) C
C21A 0.0636(9) 0.0394(7) 0.0430(7) -0.0168(7) -0.0039(5) 0.0051(5) C
C22A 0.0504(6) 0.0352(6) 0.0373(5) -0.0116(5) 0.0010(4) -0.0008(4) C
C23A 0.0490(6) 0.0313(6) 0.0376(5) -0.0094(6) 0.0023(4) -0.0039(4) C
O1B 0.112(3) 0.071(2) 0.065(2) -0.054(2) 0.027(2) -0.029(2) O
O2B 0.095(3) 0.094(3) 0.108(3) -0.054(2) 0.058(2) -0.056(2) O
O3B 0.084(2) 0.086(2) 0.073(2) -0.054(2) 0.023(2) -0.036(2) O
O4B 0.087(2) 0.102(3) 0.046(2) -0.045(2) 0.013(2) 0.000(2) O
N1B 0.0433(6) 0.0410(6) 0.0330(4) -0.0159(4) 0.0025(4) -0.0028(4) N
N2B 0.0429(6) 0.0406(5) 0.0328(4) -0.0153(4) 0.0022(4) -0.0026(3) N
N3B 0.072(2) 0.045(2) 0.034(2) -0.024(2) 0.012(2) -0.007(2) N
N4B 0.048(2) 0.056(2) 0.047(2) -0.017(2) 0.011(2) -0.012(2) N
C1B 0.0394(7) 0.0452(7) 0.0343(4) -0.0122(6) 0.0002(4) -0.0055(4) C
C2B 0.0396(6) 0.0375(6) 0.0324(4) -0.0130(4) 0.0006(4) -0.0020(4) C
C3B 0.0418(6) 0.0386(6) 0.0336(4) -0.0152(4) 0.0018(3) -0.0032(4) C
C4B 0.0521(8) 0.0399(6) 0.0357(4) -0.0202(6) 0.0054(4) -0.0038(4) C
C5B 0.0502(7) 0.0364(6) 0.0328(4) -0.0128(5) 0.0017(4) -0.0004(4) C
C6B 0.0409(6) 0.0371(6) 0.0319(4) -0.0127(4) 0.0006(4) -0.0012(4) C
C7B 0.0413(6) 0.0403(6) 0.0340(5) -0.0156(5) 0.0018(4) -0.0040(4) C
C8B 0.0428(6) 0.0498(8) 0.0369(5) -0.0199(6) 0.0041(4) -0.0087(5) C
C9B 0.0474(7) 0.0419(6) 0.0336(5) -0.0060(7) -0.0019(5) -0.0026(4) C
C10B 0.0452(6) 0.0414(7) 0.0320(4) -0.0126(4) 0.0009(3) -0.0018(4) C
C11B 0.057(1) 0.046(1) 0.0324(5) -0.0147(7) 0.0034(4) -0.0013(4) C
C12B 0.061(1) 0.053(1) 0.0320(5) -0.0077(9) -0.0001(4) -0.0021(5) C
C13B 0.051(1) 0.065(2) 0.0348(5) -0.0030(9) -0.0044(5) -0.0093(7) C
C14B 0.0427(7) 0.065(1) 0.0373(5) -0.0087(7) -0.0024(5) -0.0131(7) C
C15B 0.0411(6) 0.0484(8) 0.0341(5) -0.0114(4) -0.0006(4) -0.0062(5) C
C16B 0.0413(6) 0.0488(7) 0.0362(5) -0.0169(5) 0.0021(4) -0.0083(5) C
C17B 0.0405(5) 0.0417(6) 0.0336(4) -0.0128(4) 0.0009(3) -0.0041(4) C
C18B 0.0413(6) 0.0514(9) 0.0358(5) -0.0142(6) 0.0021(5) -0.0083(6) C
C19B 0.0438(9) 0.053(1) 0.0380(7) -0.0094(7) 0.0003(6) -0.0107(8) C
C20B 0.057(1) 0.045(1) 0.0404(8) -0.0085(7) 0.0010(7) -0.0094(8) C
C21B 0.061(1) 0.0408(8) 0.0402(8) -0.0146(6) 0.0040(6) -0.0076(7) C
C22B 0.0475(6) 0.0392(7) 0.0358(5) -0.0140(4) 0.0020(4) -0.0048(5) C
C23B 0.0500(7) 0.0412(7) 0.0369(6) -0.0193(5) 0.0046(4) -0.0059(5) C
C1Ch 0.099(1) 0.0548(7) 0.0458(7) -0.0358(5) -0.0027(6) -0.0122(4) C
Cl1Ch 0.1119(7) 0.0525(7) 0.0570(6) -0.0322(6) -0.0012(5) -0.0100(5) Cl
Cl2Ch 0.119(1) 0.0590(7) 0.076(1) -0.0455(8) 0.0098(7) -0.0049(6) Cl
Cl3Ch 0.105(1) 0.106(2) 0.0643(8) -0.0225(7) -0.0118(6) -0.0424(6) Cl

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A N3A 1.211(4) 1_555 1_555 no
O2A N3A 1.219(4) 1_555 1_555 no
O3A N4A 1.210(4) 1_555 1_555 no
O4A N4A 1.220(4) 1_555 1_555 no
N1A C2A 1.320(4) 1_555 1_555 no
N1A C10A 1.361(4) 1_555 1_555 no
N2A C6A 1.327(4) 1_555 1_555 no
N2A C17A 1.370(4) 1_555 1_555 no
N3A C11A 1.472(5) 1_555 1_555 no
N4A C18A 1.471(5) 1_555 1_555 no
C1A C2A 1.514(5) 1_555 1_555 no
C1A C8A 1.541(5) 1_555 1_555 no
C1A C9A 1.524(5) 1_555 1_555 no
C1A HC1A 1.000 1_555 1_555 no
C2A C3A 1.418(5) 1_555 1_555 no
C3A C4A 1.512(5) 1_555 1_555 no
C3A C16A 1.371(5) 1_555 1_555 no
C4A C5A 1.540(5) 1_555 1_555 no
C4A H1C4A 1.000 1_555 1_555 no
C4A H2C4A 1.000 1_555 1_555 no
C5A C6A 1.513(5) 1_555 1_555 no
C5A C9A 1.531(5) 1_555 1_555 no
C5A HC5A 1.000 1_555 1_555 no
C6A C7A 1.422(5) 1_555 1_555 no
C7A C8A 1.515(5) 1_555 1_555 no
C7A C23A 1.365(5) 1_555 1_555 no
C8A H1C8A 1.000 1_555 1_555 no
C8A H2C8A 1.000 1_555 1_555 no
C9A H1C9A 1.000 1_555 1_555 no
C9A H2C9A 1.000 1_555 1_555 no
C10A C11A 1.406(5) 1_555 1_555 no
C10A C15A 1.416(5) 1_555 1_555 no
C11A C12A 1.367(5) 1_555 1_555 no
C12A C13A 1.396(5) 1_555 1_555 no
C12A HC12A 1.000 1_555 1_555 no
C13A C14A 1.359(6) 1_555 1_555 no
C13A HC13A 1.000 1_555 1_555 no
C14A C15A 1.420(5) 1_555 1_555 no
C14A HC14A 1.000 1_555 1_555 no
C15A C16A 1.407(5) 1_555 1_555 no
C16A HC16A 1.000 1_555 1_555 no
C17A C18A 1.411(5) 1_555 1_555 no
C17A C22A 1.405(5) 1_555 1_555 no
C18A C19A 1.359(5) 1_555 1_555 no
C19A C20A 1.410(6) 1_555 1_555 no
C19A HC19A 1.000 1_555 1_555 no
C20A C21A 1.356(5) 1_555 1_555 no
C20A HC20A 1.000 1_555 1_555 no
C21A C22A 1.426(5) 1_555 1_555 no
C21A HC21A 1.000 1_555 1_555 no
C22A C23A 1.410(5) 1_555 1_555 no
C23A HC23A 1.000 1_555 1_555 no
O1B N3B 1.202(4) 1_555 1_555 no
O2B N3B 1.206(4) 1_555 1_555 no
O3B N4B 1.207(4) 1_555 1_555 no
O4B N4B 1.226(4) 1_555 1_555 no
N1B C2B 1.321(4) 1_555 1_555 no
N1B C10B 1.358(4) 1_555 1_555 no
N2B C6B 1.327(4) 1_555 1_555 no
N2B C17B 1.358(4) 1_555 1_555 no
N3B C11B 1.467(5) 1_555 1_555 no
N4B C18B 1.469(5) 1_555 1_555 no
C1B C2B 1.510(5) 1_555 1_555 no
C1B C8B 1.536(5) 1_555 1_555 no
C1B C9B 1.525(5) 1_555 1_555 no
C1B HC1B 1.000 1_555 1_555 no
C2B C3B 1.422(5) 1_555 1_555 no
C3B C4B 1.512(5) 1_555 1_555 no
C3B C16B 1.365(5) 1_555 1_555 no
C4B C5B 1.529(5) 1_555 1_555 no
C4B H1C4B 1.000 1_555 1_555 no
C4B H2C4B 1.000 1_555 1_555 no
C5B C6B 1.516(5) 1_555 1_555 no
C5B C9B 1.529(5) 1_555 1_555 no
C5B HC5B 1.000 1_555 1_555 no
C6B C7B 1.419(5) 1_555 1_555 no
C7B C8B 1.521(5) 1_555 1_555 no
C7B C23B 1.369(5) 1_555 1_555 no
C8B H1C8B 1.000 1_555 1_555 no
C8B H2C8B 1.000 1_555 1_555 no
C9B H1C9B 1.000 1_555 1_555 no
C9B H2C9B 1.000 1_555 1_555 no
C10B C11B 1.408(5) 1_555 1_555 no
C10B C15B 1.412(5) 1_555 1_555 no
C11B C12B 1.377(5) 1_555 1_555 no
C12B C13B 1.391(6) 1_555 1_555 no
C12B HC12B 1.000 1_555 1_555 no
C13B C14B 1.364(5) 1_555 1_555 no
C13B HC13B 1.000 1_555 1_555 no
C14B C15B 1.427(5) 1_555 1_555 no
C14B HC14B 1.000 1_555 1_555 no
C15B C16B 1.398(5) 1_555 1_555 no
C16B HC16B 1.000 1_555 1_555 no
C17B C18B 1.421(5) 1_555 1_555 no
C17B C22B 1.413(5) 1_555 1_555 no
C18B C19B 1.367(5) 1_555 1_555 no
C19B C20B 1.410(5) 1_555 1_555 no
C19B HC19B 1.000 1_555 1_555 no
C20B C21B 1.359(5) 1_555 1_555 no
C20B HC20B 1.000 1_555 1_555 no
C21B C22B 1.416(5) 1_555 1_555 no
C21B HC21B 1.000 1_555 1_555 no
C22B C23B 1.415(5) 1_555 1_555 no
C23B HC23B 1.000 1_555 1_555 no
C1Ch Cl1Ch 1.739(2) 1_555 1_555 no
C1Ch Cl2Ch 1.739(2) 1_555 1_555 no
C1Ch Cl3Ch 1.739(2) 1_555 1_555 no
C1Ch DC1Ch 1.000 1_555 1_555 no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A N1A C10A 117.5(3) 1_555 1_555 1_555 no
C6A N2A C17A 117.6(3) 1_555 1_555 1_555 no
O1A N3A O2A 123.8(3) 1_555 1_555 1_555 no
O1A N3A C11A 117.2(3) 1_555 1_555 1_555 no
O2A N3A C11A 118.9(3) 1_555 1_555 1_555 no
O3A N4A O4A 123.5(4) 1_555 1_555 1_555 no
O3A N4A C18A 118.6(3) 1_555 1_555 1_555 no
O4A N4A C18A 117.9(3) 1_555 1_555 1_555 no
C2A C1A C8A 108.4(3) 1_555 1_555 1_555 no
C2A C1A C9A 112.1(3) 1_555 1_555 1_555 no
C2A C1A HC1A 109.0 1_555 1_555 1_555 no
C8A C1A C9A 109.3(3) 1_555 1_555 1_555 no
C8A C1A HC1A 109.0 1_555 1_555 1_555 no
C9A C1A HC1A 109.0 1_555 1_555 1_555 no
N1A C2A C1A 114.5(3) 1_555 1_555 1_555 no
N1A C2A C3A 124.2(3) 1_555 1_555 1_555 no
C1A C2A C3A 121.1(3) 1_555 1_555 1_555 no
C2A C3A C4A 120.9(3) 1_555 1_555 1_555 no
C2A C3A C16A 117.6(3) 1_555 1_555 1_555 no
C4A C3A C16A 121.6(3) 1_555 1_555 1_555 no
C3A C4A C5A 112.8(3) 1_555 1_555 1_555 no
C3A C4A H1C4A 108.6 1_555 1_555 1_555 no
C3A C4A H2C4A 108.6 1_555 1_555 1_555 no
C5A C4A H1C4A 108.6 1_555 1_555 1_555 no
C5A C4A H2C4A 108.6 1_555 1_555 1_555 no
H1C4A C4A H2C4A 109.5 1_555 1_555 1_555 no
C4A C5A C6A 109.9(3) 1_555 1_555 1_555 no
C4A C5A C9A 108.3(3) 1_555 1_555 1_555 no
C4A C5A HC5A 108.7 1_555 1_555 1_555 no
C6A C5A C9A 112.3(3) 1_555 1_555 1_555 no
C6A C5A HC5A 108.7 1_555 1_555 1_555 no
C9A C5A HC5A 108.7 1_555 1_555 1_555 no
N2A C6A C5A 115.7(3) 1_555 1_555 1_555 no
N2A C6A C7A 123.5(3) 1_555 1_555 1_555 no
C5A C6A C7A 120.7(3) 1_555 1_555 1_555 no
C6A C7A C8A 120.9(3) 1_555 1_555 1_555 no
C6A C7A C23A 118.0(3) 1_555 1_555 1_555 no
C8A C7A C23A 121.1(3) 1_555 1_555 1_555 no
C1A C8A C7A 112.6(3) 1_555 1_555 1_555 no
C1A C8A H1C8A 108.7 1_555 1_555 1_555 no
C1A C8A H2C8A 108.7 1_555 1_555 1_555 no
C7A C8A H1C8A 108.7 1_555 1_555 1_555 no
C7A C8A H2C8A 108.7 1_555 1_555 1_555 no
H1C8A C8A H2C8A 109.5 1_555 1_555 1_555 no
C1A C9A C5A 108.4(3) 1_555 1_555 1_555 no
C1A C9A H1C9A 109.7 1_555 1_555 1_555 no
C1A C9A H2C9A 109.7 1_555 1_555 1_555 no
C5A C9A H1C9A 109.7 1_555 1_555 1_555 no
C5A C9A H2C9A 109.7 1_555 1_555 1_555 no
H1C9A C9A H2C9A 109.5 1_555 1_555 1_555 no
N1A C10A C11A 119.1(3) 1_555 1_555 1_555 no
N1A C10A C15A 123.1(3) 1_555 1_555 1_555 no
C11A C10A C15A 117.7(3) 1_555 1_555 1_555 no
N3A C11A C10A 118.9(3) 1_555 1_555 1_555 no
N3A C11A C12A 118.6(3) 1_555 1_555 1_555 no
C10A C11A C12A 122.5(3) 1_555 1_555 1_555 no
C11A C12A C13A 118.9(4) 1_555 1_555 1_555 no
C11A C12A HC12A 120.5 1_555 1_555 1_555 no
C13A C12A HC12A 120.5 1_555 1_555 1_555 no
C12A C13A C14A 121.1(4) 1_555 1_555 1_555 no
C12A C13A HC13A 119.4 1_555 1_555 1_555 no
C14A C13A HC13A 119.4 1_555 1_555 1_555 no
C13A C14A C15A 120.6(4) 1_555 1_555 1_555 no
C13A C14A HC14A 119.7 1_555 1_555 1_555 no
C15A C14A HC14A 119.7 1_555 1_555 1_555 no
C10A C15A C14A 119.0(3) 1_555 1_555 1_555 no
C10A C15A C16A 116.8(3) 1_555 1_555 1_555 no
C14A C15A C16A 124.1(3) 1_555 1_555 1_555 no
C3A C16A C15A 120.6(3) 1_555 1_555 1_555 no
C3A C16A HC16A 119.7 1_555 1_555 1_555 no
C15A C16A HC16A 119.7 1_555 1_555 1_555 no
N2A C17A C18A 119.9(3) 1_555 1_555 1_555 no
N2A C17A C22A 122.9(3) 1_555 1_555 1_555 no
C18A C17A C22A 117.2(3) 1_555 1_555 1_555 no
N4A C18A C17A 118.9(3) 1_555 1_555 1_555 no
N4A C18A C19A 117.8(3) 1_555 1_555 1_555 no
C17A C18A C19A 123.2(4) 1_555 1_555 1_555 no
C18A C19A C20A 119.0(3) 1_555 1_555 1_555 no
C18A C19A HC19A 120.5 1_555 1_555 1_555 no
C20A C19A HC19A 120.5 1_555 1_555 1_555 no
C19A C20A C21A 120.0(3) 1_555 1_555 1_555 no
C19A C20A HC20A 120.0 1_555 1_555 1_555 no
C21A C20A HC20A 120.0 1_555 1_555 1_555 no
C20A C21A C22A 121.2(4) 1_555 1_555 1_555 no
C20A C21A HC21A 119.4 1_555 1_555 1_555 no
C22A C21A HC21A 119.4 1_555 1_555 1_555 no
C17A C22A C21A 119.3(3) 1_555 1_555 1_555 no
C17A C22A C23A 117.3(3) 1_555 1_555 1_555 no
C21A C22A C23A 123.3(3) 1_555 1_555 1_555 no
C7A C23A C22A 120.4(3) 1_555 1_555 1_555 no
C7A C23A HC23A 119.8 1_555 1_555 1_555 no
C22A C23A HC23A 119.8 1_555 1_555 1_555 no
C2B N1B C10B 118.0(3) 1_555 1_555 1_555 no
C6B N2B C17B 118.2(3) 1_555 1_555 1_555 no
O1B N3B O2B 123.6(4) 1_555 1_555 1_555 no
O1B N3B C11B 118.8(3) 1_555 1_555 1_555 no
O2B N3B C11B 117.7(3) 1_555 1_555 1_555 no
O3B N4B O4B 124.1(4) 1_555 1_555 1_555 no
O3B N4B C18B 118.5(3) 1_555 1_555 1_555 no
O4B N4B C18B 117.5(3) 1_555 1_555 1_555 no
C2B C1B C8B 109.8(3) 1_555 1_555 1_555 no
C2B C1B C9B 111.9(3) 1_555 1_555 1_555 no
C2B C1B HC1B 108.6 1_555 1_555 1_555 no
C8B C1B C9B 109.3(3) 1_555 1_555 1_555 no
C8B C1B HC1B 108.6 1_555 1_555 1_555 no
C9B C1B HC1B 108.6 1_555 1_555 1_555 no
N1B C2B C1B 115.4(3) 1_555 1_555 1_555 no
N1B C2B C3B 123.7(3) 1_555 1_555 1_555 no
C1B C2B C3B 120.9(3) 1_555 1_555 1_555 no
C2B C3B C4B 120.9(3) 1_555 1_555 1_555 no
C2B C3B C16B 117.6(3) 1_555 1_555 1_555 no
C4B C3B C16B 121.3(3) 1_555 1_555 1_555 no
C3B C4B C5B 113.4(3) 1_555 1_555 1_555 no
C3B C4B H1C4B 108.5 1_555 1_555 1_555 no
C3B C4B H2C4B 108.5 1_555 1_555 1_555 no
C5B C4B H1C4B 108.5 1_555 1_555 1_555 no
C5B C4B H2C4B 108.5 1_555 1_555 1_555 no
H1C4B C4B H2C4B 109.5 1_555 1_555 1_555 no
C4B C5B C6B 110.5(3) 1_555 1_555 1_555 no
C4B C5B C9B 108.6(3) 1_555 1_555 1_555 no
C4B C5B HC5B 108.7 1_555 1_555 1_555 no
C6B C5B C9B 111.5(3) 1_555 1_555 1_555 no
C6B C5B HC5B 108.7 1_555 1_555 1_555 no
C9B C5B HC5B 108.7 1_555 1_555 1_555 no
N2B C6B C5B 115.3(3) 1_555 1_555 1_555 no
N2B C6B C7B 123.4(3) 1_555 1_555 1_555 no
C5B C6B C7B 121.3(3) 1_555 1_555 1_555 no
C6B C7B C8B 121.1(3) 1_555 1_555 1_555 no
C6B C7B C23B 118.0(3) 1_555 1_555 1_555 no
C8B C7B C23B 120.9(3) 1_555 1_555 1_555 no
C1B C8B C7B 113.0(3) 1_555 1_555 1_555 no
C1B C8B H1C8B 108.6 1_555 1_555 1_555 no
C1B C8B H2C8B 108.6 1_555 1_555 1_555 no
C7B C8B H1C8B 108.6 1_555 1_555 1_555 no
C7B C8B H2C8B 108.6 1_555 1_555 1_555 no
H1C8B C8B H2C8B 109.5 1_555 1_555 1_555 no
C1B C9B C5B 108.5(3) 1_555 1_555 1_555 no
C1B C9B H1C9B 109.7 1_555 1_555 1_555 no
C1B C9B H2C9B 109.7 1_555 1_555 1_555 no
C5B C9B H1C9B 109.7 1_555 1_555 1_555 no
C5B C9B H2C9B 109.7 1_555 1_555 1_555 no
H1C9B C9B H2C9B 109.5 1_555 1_555 1_555 no
N1B C10B C11B 119.8(3) 1_555 1_555 1_555 no
N1B C10B C15B 122.5(3) 1_555 1_555 1_555 no
C11B C10B C15B 117.6(3) 1_555 1_555 1_555 no
N3B C11B C10B 119.5(3) 1_555 1_555 1_555 no
N3B C11B C12B 117.7(3) 1_555 1_555 1_555 no
C10B C11B C12B 122.8(4) 1_555 1_555 1_555 no
C11B C12B C13B 118.5(3) 1_555 1_555 1_555 no
C11B C12B HC12B 120.7 1_555 1_555 1_555 no
C13B C12B HC12B 120.7 1_555 1_555 1_555 no
C12B C13B C14B 121.5(4) 1_555 1_555 1_555 no
C12B C13B HC13B 119.3 1_555 1_555 1_555 no
C14B C13B HC13B 119.3 1_555 1_555 1_555 no
C13B C14B C15B 120.3(4) 1_555 1_555 1_555 no
C13B C14B HC14B 119.8 1_555 1_555 1_555 no
C15B C14B HC14B 119.8 1_555 1_555 1_555 no
C10B C15B C14B 119.2(3) 1_555 1_555 1_555 no
C10B C15B C16B 117.5(3) 1_555 1_555 1_555 no
C14B C15B C16B 123.3(3) 1_555 1_555 1_555 no
C3B C16B C15B 120.7(3) 1_555 1_555 1_555 no
C3B C16B HC16B 119.7 1_555 1_555 1_555 no
C15B C16B HC16B 119.7 1_555 1_555 1_555 no
N2B C17B C18B 120.1(3) 1_555 1_555 1_555 no
N2B C17B C22B 123.1(3) 1_555 1_555 1_555 no
C18B C17B C22B 116.8(3) 1_555 1_555 1_555 no
N4B C18B C17B 119.3(3) 1_555 1_555 1_555 no
N4B C18B C19B 118.1(3) 1_555 1_555 1_555 no
C17B C18B C19B 122.6(3) 1_555 1_555 1_555 no
C18B C19B C20B 119.2(3) 1_555 1_555 1_555 no
C18B C19B HC19B 120.4 1_555 1_555 1_555 no
C20B C19B HC19B 120.4 1_555 1_555 1_555 no
C19B C20B C21B 120.4(3) 1_555 1_555 1_555 no
C19B C20B HC20B 119.8 1_555 1_555 1_555 no
C21B C20B HC20B 119.8 1_555 1_555 1_555 no
C20B C21B C22B 120.8(4) 1_555 1_555 1_555 no
C20B C21B HC21B 119.6 1_555 1_555 1_555 no
C22B C21B HC21B 119.6 1_555 1_555 1_555 no
C17B C22B C21B 120.1(3) 1_555 1_555 1_555 no
C17B C22B C23B 116.7(3) 1_555 1_555 1_555 no
C21B C22B C23B 123.1(3) 1_555 1_555 1_555 no
C7B C23B C22B 120.6(3) 1_555 1_555 1_555 no
C7B C23B HC23B 119.7 1_555 1_555 1_555 no
C22B C23B HC23B 119.7 1_555 1_555 1_555 no
Cl1Ch C1Ch Cl2Ch 111.0(2) 1_555 1_555 1_555 no
Cl1Ch C1Ch Cl3Ch 111.0(2) 1_555 1_555 1_555 no
Cl1Ch C1Ch DC1Ch 107.9 1_555 1_555 1_555 no
Cl2Ch C1Ch Cl3Ch 111.0(1) 1_555 1_555 1_555 no
Cl2Ch C1Ch DC1Ch 107.9 1_555 1_555 1_555 no
Cl3Ch C1Ch DC1Ch 107.9 1_555 1_555 1_555 no

# Attachment 'drb312.cif'

data_drb312
_database_code_depnum_ccdc_archive 'CCDC 668452'
_audit_creation_method           'RAELSPUB and manual entry'

_computing_data_collection       'CAD4 Version 5.0, (Schagen et al, 1989)'
_computing_cell_refinement       'CAD4 Version 5.0, (Schagen et al, 1989)'
_computing_data_reduction        'Local program'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'RAELS, (Rae, 1996)'
_computing_molecular_graphics    'ORTEP-II, (Johnson, 1976)'
_computing_publication_material  'Local programs'

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N4 O4'
_chemical_formula_sum            'C23 H16 N4 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         412.4
_chemical_absolute_configuration ?

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c n'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,1/2-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,1/2-z
7 1/2-x,1/2+y,z
8 x,-y,1/2+z

_cell_length_a                   7.883(2)
_cell_length_b                   9.292(4)
_cell_length_c                   25.355(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1857(1)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11
_cell_measurement_theta_min      10
_cell_measurement_theta_max      11
_cell_measurement_temperature    294
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.47
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856.0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

# EXPERIMENTAL DATA

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       \w--2\q
_diffrn_reflns_number            1634
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_theta_max         25
_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1.00
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         1
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        0

# REFINEMENT DATA

_refine_special_details          ?
_reflns_number_total             1634
_reflns_number_gt                833
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.052
_refine_ls_wR_factor_ref         0.058
_refine_ls_abs_structure_Flack   ?
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         833
_refine_ls_number_parameters     74
_refine_ls_goodness_of_fit_ref   1.64
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[\s^2^(F) + 0.0004F^2^]'
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_atom_type_scat_source           
'International Tables for X-ray Crystallography, Vol. IV'

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
_atom_site_occupancy
O1 0.6682(4) 0.6204(4) 0.0819(1) 0.087(1) Uani O 1.0
O2 0.5325(5) 0.6711(4) 0.0122(1) 0.078(1) Uani O 1.0
N1 0.2261(4) 0.2913(3) 0.1757(1) 0.0383(7) Uani N 1.0
N2 0.5402(5) 0.6152(4) 0.0554(2) 0.053(1) Uani N 1.0
C1 0.3432(5) 0.1395(4) 0.2429(1) 0.0420(8) Uani C 1.0
C2 0.3656(5) 0.2440(4) 0.1977(1) 0.0356(7) Uani C 1.0
C3 0.5303(5) 0.2868(4) 0.1817(1) 0.0343(6) Uani C 1.0
C4 0.6893(5) 0.2205(4) 0.2051(1) 0.0402(8) Uani C 1.0
C5 0.5000 0.0442(5) 0.2500 0.048(1) Uani C 1.0
C6 0.2389(5) 0.3892(4) 0.1357(1) 0.0373(6) Uani C 1.0
C7 0.0848(5) 0.4339(5) 0.1125(2) 0.0454(8) Uani C 1.0
C8 0.0852(5) 0.5329(5) 0.0723(2) 0.050(1) Uani C 1.0
C9 0.2395(6) 0.5907(4) 0.0542(1) 0.0479(8) Uani C 1.0
C10 0.3868(5) 0.5471(4) 0.0767(2) 0.0423(6) Uani C 1.0
C11 0.3968(4) 0.4437(4) 0.1179(2) 0.0359(5) Uani C 1.0
C12 0.5439(5) 0.3873(4) 0.1421(1) 0.0354(5) Uani C 1.0
HC1 0.2432 0.0766 0.2352 0.051 Uani H 1.0
H1C4 0.7732 0.2991 0.2119 0.041 Uani H 1.0
H2C4 0.7377 0.1513 0.1789 0.048 Uani H 1.0
H1C5 0.5150 -0.0180 0.2181 0.055 Uani H 0.5
H2C5 0.4850 -0.0180 0.2819 0.055 Uani H 0.5
HC7 -0.0251 0.3932 0.1254 0.053 Uani H 1.0
HC8 -0.0241 0.5639 0.0559 0.059 Uani H 1.0
HC9 0.2405 0.6633 0.0251 0.055 Uani H 1.0
HC12 0.6584 0.4204 0.1303 0.041 Uani H 1.0

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
O1 0.056(2) 0.111(3) 0.092(3) -0.026(2) -0.012(2) 0.045(3) O
O2 0.095(3) 0.082(2) 0.056(2) -0.011(2) 0.009(2) 0.030(2) O
N1 0.037(1) 0.0423(8) 0.0357(6) -0.0059(5) -0.0005(5) 0.0004(2) N
N2 0.060(3) 0.051(2) 0.047(2) -0.003(2) 0.007(2) 0.010(2) N
C1 0.054(2) 0.0340(8) 0.0385(7) -0.0111(6) -0.0034(8) 0.0025(3) C
C2 0.040(1) 0.0315(7) 0.0351(7) -0.0039(3) -0.0003(6) -0.0002(1) C
C3 0.037(1) 0.0320(8) 0.0339(7) 0.0024(2) 0.0013(7) -0.0016(2) C
C4 0.043(1) 0.042(1) 0.0361(6) 0.0110(7) 0.0003(8) -0.0039(4) C
C5 0.073(3) 0.0282(8) 0.042(1) 0.0000 -0.008(1) 0.0000 C
C6 0.0361(9) 0.0411(7) 0.0349(6) 0.0003(4) -0.0005(5) 0.0000 C
C7 0.0385(8) 0.060(2) 0.0377(8) 0.0047(8) -0.0029(8) -0.0001(2) C
C8 0.0489(9) 0.061(2) 0.0393(8) 0.012(1) -0.006(1) 0.0011(5) C
C9 0.058(1) 0.047(1) 0.0383(6) 0.0065(9) -0.0060(7) 0.0048(7) C
C10 0.0501(9) 0.041(1) 0.0356(7) -0.0013(6) -0.0021(5) 0.0048(6) C
C11 0.0385(8) 0.0356(8) 0.0337(7) 0.0000(2) 0.0005(6) 0.0013(2) C
C12 0.0357(9) 0.0375(9) 0.0332(7) -0.0002(3) 0.0023(7) 0.0001(2) C

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.214(4) 1_555 1_555 no
O2 N2 1.213(4) 1_555 1_555 no
N1 C2 1.309(4) 1_555 1_555 no
N1 C6 1.366(4) 1_555 1_555 no
N2 C10 1.467(5) 1_555 1_555 no
C1 C2 1.513(5) 1_555 1_555 no
C1 C4 1.542(5) 1_555 4_655 no
C1 C5 1.531(5) 1_555 1_555 no
C1 HC1 1.000 1_555 1_555 no
C2 C3 1.416(5) 1_555 1_555 no
C3 C4 1.517(5) 1_555 1_555 no
C3 C12 1.376(5) 1_555 1_555 no
C4 C1 1.542(5) 1_555 4_655 no
C4 H1C4 1.000 1_555 1_555 no
C4 H2C4 1.000 1_555 1_555 no
C5 C1 1.531(5) 1_555 4_655 no
C5 H1C5 1.000 1_555 1_555 no
C5 H2C5 1.000 1_555 1_555 no
C6 C7 1.412(5) 1_555 1_555 no
C6 C11 1.418(5) 1_555 1_555 no
C7 C8 1.373(6) 1_555 1_555 no
C7 HC7 1.000 1_555 1_555 no
C8 C9 1.406(5) 1_555 1_555 no
C8 HC8 1.000 1_555 1_555 no
C9 C10 1.355(5) 1_555 1_555 no
C9 HC9 1.000 1_555 1_555 no
C10 C11 1.423(5) 1_555 1_555 no
C11 C12 1.411(5) 1_555 1_555 no
C12 HC12 1.000 1_555 1_555 no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 118.5(3) 1_555 1_555 1_555 no
O1 N2 O2 121.6(4) 1_555 1_555 1_555 no
O1 N2 C10 119.9(4) 1_555 1_555 1_555 no
O2 N2 C10 118.4(4) 1_555 1_555 1_555 no
C2 C1 C4 110.8(3) 1_555 1_555 4_655 no
C2 C1 C5 111.5(3) 1_555 1_555 1_555 no
C2 C1 HC1 108.7 1_555 1_555 1_555 no
C4 C1 C5 108.4(3) 4_655 1_555 1_555 no
C4 C1 HC1 108.7 4_655 1_555 1_555 no
C5 C1 HC1 108.7 1_555 1_555 1_555 no
N1 C2 C1 116.1(4) 1_555 1_555 1_555 no
N1 C2 C3 123.7(3) 1_555 1_555 1_555 no
C1 C2 C3 120.2(4) 1_555 1_555 1_555 no
C2 C3 C4 122.2(3) 1_555 1_555 1_555 no
C2 C3 C12 118.0(4) 1_555 1_555 1_555 no
C4 C3 C12 119.7(4) 1_555 1_555 1_555 no
C1 C4 C3 113.2(3) 4_655 1_555 1_555 no
C1 C4 H1C4 108.5 4_655 1_555 1_555 no
C1 C4 H2C4 108.5 4_655 1_555 1_555 no
C3 C4 H1C4 108.5 1_555 1_555 1_555 no
C3 C4 H2C4 108.5 1_555 1_555 1_555 no
H1C4 C4 H2C4 109.5 1_555 1_555 1_555 no
C1 C5 C1 109.3(4) 1_555 1_555 4_655 no
C1 C5 H1C5 109.5 1_555 1_555 1_555 no
C1 C5 H2C5 109.5 1_555 1_555 1_555 no
C1 C5 H1C5 109.5 4_655 1_555 1_555 no
C1 C5 H2C5 109.5 4_655 1_555 1_555 no
H1C5 C5 H2C5 109.5 1_555 1_555 1_555 no
N1 C6 C7 116.2(4) 1_555 1_555 1_555 no
N1 C6 C11 122.6(4) 1_555 1_555 1_555 no
C7 C6 C11 121.2(3) 1_555 1_555 1_555 no
C6 C7 C8 120.3(4) 1_555 1_555 1_555 no
C6 C7 HC7 119.8 1_555 1_555 1_555 no
C8 C7 HC7 119.8 1_555 1_555 1_555 no
C7 C8 C9 120.0(4) 1_555 1_555 1_555 no
C7 C8 HC8 120.0 1_555 1_555 1_555 no
C9 C8 HC8 120.0 1_555 1_555 1_555 no
C8 C9 C10 119.4(4) 1_555 1_555 1_555 no
C8 C9 HC9 120.3 1_555 1_555 1_555 no
C10 C9 HC9 120.3 1_555 1_555 1_555 no
N2 C10 C9 115.0(4) 1_555 1_555 1_555 no
N2 C10 C11 121.1(4) 1_555 1_555 1_555 no
C9 C10 C11 123.9(4) 1_555 1_555 1_555 no
C6 C11 C10 115.2(4) 1_555 1_555 1_555 no
C6 C11 C12 116.8(3) 1_555 1_555 1_555 no
C10 C11 C12 128.0(4) 1_555 1_555 1_555 no
C3 C12 C11 120.3(4) 1_555 1_555 1_555 no
C3 C12 HC12 119.8 1_555 1_555 1_555 no
C11 C12 HC12 119.8 1_555 1_555 1_555 no

# Attachment 'drb314.cif'

data_drb314
_database_code_depnum_ccdc_archive 'CCDC 668453'
_audit_creation_method           'RAELSPUB and manual entry'

_computing_data_collection       'CAD4 Version 5.0, (Schagen et al, 1989)'
_computing_cell_refinement       'CAD4 Version 5.0, (Schagen et al, 1989)'
_computing_data_reduction        'Local program'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'RAELS, (Rae, 1996)'
_computing_molecular_graphics    'ORTEP-II, (Johnson, 1976)'
_computing_publication_material  'Local programs'

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N4 O4, 0.5(C7 H8)'
_chemical_formula_sum            'C26.5 H20 N4 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         458.5
_chemical_absolute_configuration ?

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c c n'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,1/2-y,z
3 1/2+x,-y,1/2-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,1/2+y,-z
7 1/2-x,y,1/2+z
8 x,1/2-y,1/2+z

_cell_length_a                   16.642(6)
_cell_length_b                   19.026(8)
_cell_length_c                   13.490(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4271(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11
_cell_measurement_theta_min      10
_cell_measurement_theta_max      11
_cell_measurement_temperature    294
_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.12
_exptl_crystal_density_diffrn    1.43
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1912.0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

# EXPERIMENTAL DATA

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       \w--2\q
_diffrn_reflns_number            3740
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_theta_max         25
_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1.00
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         1
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        0

# REFINEMENT DATA

_refine_special_details          ?
_reflns_number_total             3739
_reflns_number_gt                1641
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.069
_refine_ls_wR_factor_ref         0.072
_refine_ls_abs_structure_Flack   ?
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         1641
_refine_ls_number_parameters     166
_refine_ls_goodness_of_fit_ref   1.74
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[\s^2^(F) + 0.0004F^2^]'
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.98
_refine_diff_density_min         -0.59
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_atom_type_scat_source           
'International Tables for X-ray Crystallography, Vol. IV'

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
_atom_site_occupancy
O1 0.6175(3) 0.6469(3) 0.0729(4) 0.091(2) Uani O 1.0
O2 0.6367(4) 0.7432(3) 0.1472(4) 0.102(2) Uani O 1.0
O3 0.0912(5) 0.6225(4) 0.4418(5) 0.189(5) Uani O 1.0
O4 0.0271(4) 0.7084(3) 0.3952(4) 0.121(2) Uani O 1.0
N1 0.4706(3) 0.5079(2) 0.3525(3) 0.0397(7) Uani N 1.0
N2 0.2105(3) 0.5292(2) 0.1109(3) 0.0474(7) Uani N 1.0
N3 0.6157(3) 0.6832(3) 0.1473(4) 0.057(2) Uani N 1.0
N4 0.0676(4) 0.6575(3) 0.3792(5) 0.074(2) Uani N 1.0
C1 0.3706(3) 0.4256(3) 0.2973(4) 0.0422(8) Uani C 1.0
C2 0.4305(3) 0.4838(3) 0.2752(4) 0.0385(7) Uani C 1.0
C3 0.4389(3) 0.5117(3) 0.1781(4) 0.0398(6) Uani C 1.0
C4 0.3880(3) 0.4851(3) 0.0933(4) 0.0461(6) Uani C 1.0
C5 0.3150(3) 0.4429(3) 0.1295(4) 0.0463(6) Uani C 1.0
C6 0.2537(4) 0.4922(3) 0.1748(4) 0.0427(6) Uani C 1.0
C7 0.2446(3) 0.4989(3) 0.2787(4) 0.0407(6) Uani C 1.0
C8 0.2960(3) 0.4559(3) 0.3494(4) 0.0426(8) Uani C 1.0
C9 0.3440(3) 0.3872(3) 0.2034(4) 0.0471(9) Uani C 1.0
C10 0.5232(3) 0.5621(3) 0.3387(4) 0.0398(6) Uani C 1.0
C11 0.5626(3) 0.5879(3) 0.4238(4) 0.0460(7) Uani C 1.0
C12 0.6125(4) 0.6448(3) 0.4178(4) 0.0499(9) Uani C 1.0
C13 0.6283(3) 0.6759(3) 0.3247(5) 0.049(1) Uani C 1.0
C14 0.5933(3) 0.6496(3) 0.2422(4) 0.0447(8) Uani C 1.0
C15 0.5388(3) 0.5926(3) 0.2439(4) 0.0400(6) Uani C 1.0
C16 0.4929(3) 0.5647(3) 0.1634(4) 0.0410(6) Uani C 1.0
C17 0.1566(3) 0.5771(3) 0.1467(5) 0.0482(7) Uani C 1.0
C18 0.1134(4) 0.6165(3) 0.0761(5) 0.058(1) Uani C 1.0
C19 0.0597(4) 0.6669(3) 0.1050(5) 0.063(2) Uani C 1.0
C20 0.0470(3) 0.6793(3) 0.2057(5) 0.060(1) Uani C 1.0
C21 0.0867(4) 0.6410(3) 0.2748(5) 0.0530(7) Uani C 1.0
C22 0.1435(3) 0.5880(3) 0.2495(4) 0.0461(6) Uani C 1.0
C23 0.1903(3) 0.5469(3) 0.3148(4) 0.0432(6) Uani C 1.0
C1T 0.7796(7) 0.2739(6) 0.2591(6) 0.093(4) Uani C 0.5
C2T 0.7349(9) 0.2367(6) 0.3304(9) 0.079(4) Uani C 0.5
C3T 0.6791(7) 0.1881(6) 0.3018(11) 0.072(4) Uani C 0.5
C4T 0.6655(7) 0.1744(6) 0.2050(8) 0.072(4) Uani C 0.5
C5T 0.7073(8) 0.2091(7) 0.1344(11) 0.083(6) Uani C 0.5
C6T 0.7637(7) 0.2582(7) 0.1590(9) 0.097(5) Uani C 0.5
C7T 0.8407(11) 0.3272(9) 0.2880(12) 0.168(6) Uani C 0.5
HC1 0.3966 0.3908 0.3427 0.047 Uani H 1.0
H1C4 0.4218 0.4542 0.0501 0.053 Uani H 1.0
H2C4 0.3685 0.5263 0.0539 0.049 Uani H 1.0
HC5 0.2900 0.4186 0.0714 0.054 Uani H 1.0
H1C8 0.2631 0.4162 0.3761 0.048 Uani H 1.0
H2C8 0.3139 0.4867 0.4052 0.043 Uani H 1.0
H1C9 0.2992 0.3540 0.2192 0.051 Uani H 1.0
H2C9 0.3902 0.3605 0.1747 0.051 Uani H 1.0
HC11 0.5539 0.5643 0.4892 0.051 Uani H 1.0
HC12 0.6378 0.6643 0.4791 0.058 Uani H 1.0
HC13 0.6653 0.7172 0.3198 0.054 Uani H 1.0
HC16 0.5006 0.5842 0.0953 0.046 Uani H 1.0
HC18 0.1222 0.6075 0.0039 0.065 Uani H 1.0
HC19 0.0297 0.6947 0.0541 0.073 Uani H 1.0
HC20 0.0085 0.7167 0.2270 0.067 Uani H 1.0
HC23 0.1838 0.5528 0.3880 0.047 Uani H 1.0
HC2T 0.7439 0.2460 0.4025 0.112 Uani H 0.5
HC3T 0.6479 0.1621 0.3534 0.106 Uani H 0.5
HC4T 0.6244 0.1386 0.1855 0.102 Uani H 0.5
HC5T 0.6968 0.1986 0.0630 0.120 Uani H 0.5
HC6T 0.7940 0.2833 0.1056 0.149 Uani H 0.5

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
O1 0.116(4) 0.098(4) 0.060(3) -0.035(4) 0.013(3) -0.007(3) O
O2 0.154(5) 0.064(3) 0.088(4) -0.038(4) 0.025(4) 0.005(4) O
O3 0.305(9) 0.178(7) 0.084(5) 0.179(7) 0.081(5) 0.058(4) O
O4 0.113(5) 0.125(5) 0.125(5) 0.049(4) -0.001(4) -0.047(4) O
N1 0.0391(7) 0.0441(8) 0.036(1) 0.0012(5) -0.0020(6) 0.0002(8) N
N2 0.0450(7) 0.052(1) 0.0454(8) 0.0009(7) -0.0101(8) -0.0050(8) N
N3 0.060(4) 0.050(4) 0.060(4) -0.009(3) 0.021(3) -0.001(4) N
N4 0.050(4) 0.066(5) 0.105(6) 0.008(4) 0.014(4) -0.013(4) N
C1 0.0378(7) 0.0419(9) 0.047(1) 0.0013(6) -0.0004(8) -0.0003(8) C
C2 0.0374(7) 0.0416(9) 0.037(1) 0.0015(6) 0.0001(6) -0.0026(8) C
C3 0.0400(7) 0.0458(9) 0.034(1) 0.0016(6) 0.0021(7) -0.0059(8) C
C4 0.0469(9) 0.056(1) 0.036(1) 0.0014(7) 0.0003(7) -0.012(1) C
C5 0.0437(9) 0.0501(9) 0.045(1) 0.0015(7) -0.0038(8) -0.013(1) C
C6 0.0402(7) 0.0453(8) 0.0425(8) 0.0013(6) -0.0045(7) -0.0062(7) C
C7 0.0373(7) 0.0420(8) 0.0429(8) 0.0013(6) 0.0005(6) -0.0018(7) C
C8 0.0391(7) 0.0448(9) 0.044(1) 0.0009(7) 0.0023(8) 0.003(1) C
C9 0.039(1) 0.0435(9) 0.058(2) 0.0017(6) -0.002(1) -0.0099(9) C
C10 0.0385(7) 0.0432(8) 0.0378(8) 0.0014(5) -0.0027(6) -0.0023(7) C
C11 0.0440(7) 0.051(1) 0.0433(8) 0.0010(6) -0.0088(7) -0.0040(7) C
C12 0.0437(8) 0.050(1) 0.056(1) 0.0010(8) -0.011(1) -0.008(1) C
C13 0.0383(7) 0.0429(9) 0.064(2) 0.0011(8) -0.0046(9) -0.004(1) C
C14 0.0376(7) 0.043(1) 0.054(1) 0.0011(7) 0.0021(7) 0.000(1) C
C15 0.0375(7) 0.0425(8) 0.0401(8) 0.0014(6) 0.0019(7) -0.0019(7) C
C16 0.0407(7) 0.048(1) 0.0346(9) 0.0013(6) 0.0045(8) -0.0028(8) C
C17 0.0419(7) 0.048(1) 0.055(1) 0.0010(6) -0.0103(8) -0.0007(9) C
C18 0.0485(9) 0.056(2) 0.068(2) 0.0004(9) -0.020(1) 0.005(1) C
C19 0.0455(9) 0.052(2) 0.091(3) 0.001(1) -0.020(1) 0.009(2) C
C20 0.0387(7) 0.044(2) 0.098(3) 0.002(1) -0.009(1) 0.002(2) C
C21 0.0374(7) 0.043(2) 0.079(2) 0.0019(8) 0.0006(8) -0.003(2) C
C22 0.0374(7) 0.042(1) 0.058(1) 0.0015(6) -0.0016(7) -0.0021(9) C
C23 0.0378(7) 0.043(1) 0.0483(9) 0.0014(6) 0.0035(7) -0.0020(8) C
C1T 0.081(7) 0.035(5) 0.163(7) 0.007(4) -0.029(6) -0.003(5) C
C2T 0.065(6) 0.055(5) 0.115(6) 0.033(4) -0.010(5) -0.035(5) C
C3T 0.045(6) 0.069(5) 0.103(7) 0.022(4) -0.002(5) -0.007(5) C
C4T 0.051(6) 0.056(6) 0.109(7) 0.012(4) -0.012(5) -0.011(5) C
C5T 0.054(8) 0.094(9) 0.101(7) 0.019(6) -0.008(5) -0.002(5) C
C6T 0.063(9) 0.090(7) 0.139(6) 0.004(5) -0.015(6) 0.036(7) C
C7T 0.153(9) 0.059(5) 0.290(9) -0.034(8) -0.085(9) 0.010(8) C

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.219(6) 1_555 1_555 no
O2 N3 1.194(6) 1_555 1_555 no
O3 N4 1.145(7) 1_555 1_555 no
O4 N4 1.200(7) 1_555 1_555 no
N1 C2 1.320(6) 1_555 1_555 no
N1 C10 1.365(6) 1_555 1_555 no
N2 C6 1.325(6) 1_555 1_555 no
N2 C17 1.366(6) 1_555 1_555 no
N3 C14 1.479(7) 1_555 1_555 no
N4 C21 1.477(8) 1_555 1_555 no
C1 C2 1.520(7) 1_555 1_555 no
C1 C8 1.538(7) 1_555 1_555 no
C1 C9 1.528(7) 1_555 1_555 no
C1 HC1 1.000 1_555 1_555 no
C2 C3 1.420(7) 1_555 1_555 no
C3 C4 1.512(7) 1_555 1_555 no
C3 C16 1.365(7) 1_555 1_555 no
C4 C5 1.536(7) 1_555 1_555 no
C4 H1C4 1.000 1_555 1_555 no
C4 H2C4 1.000 1_555 1_555 no
C5 C6 1.516(7) 1_555 1_555 no
C5 C9 1.532(7) 1_555 1_555 no
C5 HC5 1.000 1_555 1_555 no
C6 C7 1.416(7) 1_555 1_555 no
C7 C8 1.521(7) 1_555 1_555 no
C7 C23 1.374(7) 1_555 1_555 no
C8 H1C8 1.000 1_555 1_555 no
C8 H2C8 1.000 1_555 1_555 no
C9 H1C9 1.000 1_555 1_555 no
C9 H2C9 1.000 1_555 1_555 no
C10 C11 1.410(7) 1_555 1_555 no
C10 C15 1.428(7) 1_555 1_555 no
C11 C12 1.368(7) 1_555 1_555 no
C11 HC11 1.000 1_555 1_555 no
C12 C13 1.413(7) 1_555 1_555 no
C12 HC12 1.000 1_555 1_555 no
C13 C14 1.352(7) 1_555 1_555 no
C13 HC13 1.000 1_555 1_555 no
C14 C15 1.414(7) 1_555 1_555 no
C15 C16 1.429(7) 1_555 1_555 no
C16 HC16 1.000 1_555 1_555 no
C17 C18 1.409(7) 1_555 1_555 no
C17 C22 1.419(7) 1_555 1_555 no
C18 C19 1.367(8) 1_555 1_555 no
C18 HC18 1.000 1_555 1_555 no
C19 C20 1.395(8) 1_555 1_555 no
C19 HC19 1.000 1_555 1_555 no
C20 C21 1.356(8) 1_555 1_555 no
C20 HC20 1.000 1_555 1_555 no
C21 C22 1.424(7) 1_555 1_555 no
C22 C23 1.410(7) 1_555 1_555 no
C23 HC23 1.000 1_555 1_555 no
C1T C2T 1.407(11) 1_555 1_555 no
C1T C6T 1.407(11) 1_555 1_555 no
C1T C7T 1.487(21) 1_555 1_555 no
C2T C3T 1.366(16) 1_555 1_555 no
C2T HC2T 1.000 1_555 1_555 no
C3T C4T 1.351(12) 1_555 1_555 no
C3T HC3T 1.000 1_555 1_555 no
C4T C5T 1.351(12) 1_555 1_555 no
C4T HC4T 1.000 1_555 1_555 no
C5T C6T 1.366(16) 1_555 1_555 no
C5T HC5T 1.000 1_555 1_555 no
C6T HC6T 1.000 1_555 1_555 no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C10 118.6(5) 1_555 1_555 1_555 no
C6 N2 C17 118.7(5) 1_555 1_555 1_555 no
O1 N3 O2 122.3(6) 1_555 1_555 1_555 no
O1 N3 C14 118.2(6) 1_555 1_555 1_555 no
O2 N3 C14 119.3(6) 1_555 1_555 1_555 no
O3 N4 O4 122.1(8) 1_555 1_555 1_555 no
O3 N4 C21 120.3(7) 1_555 1_555 1_555 no
O4 N4 C21 117.7(7) 1_555 1_555 1_555 no
C2 C1 C8 110.2(4) 1_555 1_555 1_555 no
C2 C1 C9 112.1(5) 1_555 1_555 1_555 no
C2 C1 HC1 108.5 1_555 1_555 1_555 no
C8 C1 C9 108.9(5) 1_555 1_555 1_555 no
C8 C1 HC1 108.5 1_555 1_555 1_555 no
C9 C1 HC1 108.5 1_555 1_555 1_555 no
N1 C2 C1 115.5(5) 1_555 1_555 1_555 no
N1 C2 C3 123.3(5) 1_555 1_555 1_555 no
C1 C2 C3 121.2(5) 1_555 1_555 1_555 no
C2 C3 C4 121.2(5) 1_555 1_555 1_555 no
C2 C3 C16 118.3(5) 1_555 1_555 1_555 no
C4 C3 C16 120.5(5) 1_555 1_555 1_555 no
C3 C4 C5 112.2(5) 1_555 1_555 1_555 no
C3 C4 H1C4 108.8 1_555 1_555 1_555 no
C3 C4 H2C4 108.8 1_555 1_555 1_555 no
C5 C4 H1C4 108.8 1_555 1_555 1_555 no
C5 C4 H2C4 108.8 1_555 1_555 1_555 no
H1C4 C4 H2C4 109.5 1_555 1_555 1_555 no
C4 C5 C6 109.7(5) 1_555 1_555 1_555 no
C4 C5 C9 108.7(5) 1_555 1_555 1_555 no
C4 C5 HC5 108.7 1_555 1_555 1_555 no
C6 C5 C9 112.2(5) 1_555 1_555 1_555 no
C6 C5 HC5 108.7 1_555 1_555 1_555 no
C9 C5 HC5 108.7 1_555 1_555 1_555 no
N2 C6 C5 115.7(5) 1_555 1_555 1_555 no
N2 C6 C7 122.5(5) 1_555 1_555 1_555 no
C5 C6 C7 121.8(5) 1_555 1_555 1_555 no
C6 C7 C8 120.8(5) 1_555 1_555 1_555 no
C6 C7 C23 118.8(5) 1_555 1_555 1_555 no
C8 C7 C23 120.4(5) 1_555 1_555 1_555 no
C1 C8 C7 111.7(4) 1_555 1_555 1_555 no
C1 C8 H1C8 108.9 1_555 1_555 1_555 no
C1 C8 H2C8 108.9 1_555 1_555 1_555 no
C7 C8 H1C8 108.9 1_555 1_555 1_555 no
C7 C8 H2C8 108.9 1_555 1_555 1_555 no
H1C8 C8 H2C8 109.5 1_555 1_555 1_555 no
C1 C9 C5 107.5(5) 1_555 1_555 1_555 no
C1 C9 H1C9 110.0 1_555 1_555 1_555 no
C1 C9 H2C9 110.0 1_555 1_555 1_555 no
C5 C9 H1C9 110.0 1_555 1_555 1_555 no
C5 C9 H2C9 110.0 1_555 1_555 1_555 no
H1C9 C9 H2C9 109.5 1_555 1_555 1_555 no
N1 C10 C11 116.7(5) 1_555 1_555 1_555 no
N1 C10 C15 123.1(5) 1_555 1_555 1_555 no
C11 C10 C15 120.2(5) 1_555 1_555 1_555 no
C10 C11 C12 120.6(5) 1_555 1_555 1_555 no
C10 C11 HC11 119.7 1_555 1_555 1_555 no
C12 C11 HC11 119.7 1_555 1_555 1_555 no
C11 C12 C13 119.8(5) 1_555 1_555 1_555 no
C11 C12 HC12 120.1 1_555 1_555 1_555 no
C13 C12 HC12 120.1 1_555 1_555 1_555 no
C12 C13 C14 119.7(6) 1_555 1_555 1_555 no
C12 C13 HC13 120.1 1_555 1_555 1_555 no
C14 C13 HC13 120.1 1_555 1_555 1_555 no
N3 C14 C13 116.3(6) 1_555 1_555 1_555 no
N3 C14 C15 120.5(6) 1_555 1_555 1_555 no
C13 C14 C15 123.2(6) 1_555 1_555 1_555 no
C10 C15 C14 116.3(5) 1_555 1_555 1_555 no
C10 C15 C16 115.6(5) 1_555 1_555 1_555 no
C14 C15 C16 128.0(5) 1_555 1_555 1_555 no
C3 C16 C15 121.1(5) 1_555 1_555 1_555 no
C3 C16 HC16 119.5 1_555 1_555 1_555 no
C15 C16 HC16 119.5 1_555 1_555 1_555 no
N2 C17 C18 116.8(6) 1_555 1_555 1_555 no
N2 C17 C22 122.9(5) 1_555 1_555 1_555 no
C18 C17 C22 120.3(6) 1_555 1_555 1_555 no
C17 C18 C19 120.9(6) 1_555 1_555 1_555 no
C17 C18 HC18 119.5 1_555 1_555 1_555 no
C19 C18 HC18 119.5 1_555 1_555 1_555 no
C18 C19 C20 119.7(6) 1_555 1_555 1_555 no
C18 C19 HC19 120.2 1_555 1_555 1_555 no
C20 C19 HC19 120.2 1_555 1_555 1_555 no
C19 C20 C21 120.4(6) 1_555 1_555 1_555 no
C19 C20 HC20 119.8 1_555 1_555 1_555 no
C21 C20 HC20 119.8 1_555 1_555 1_555 no
N4 C21 C20 115.9(6) 1_555 1_555 1_555 no
N4 C21 C22 121.5(6) 1_555 1_555 1_555 no
C20 C21 C22 122.7(7) 1_555 1_555 1_555 no
C17 C22 C21 116.1(6) 1_555 1_555 1_555 no
C17 C22 C23 116.4(5) 1_555 1_555 1_555 no
C21 C22 C23 127.5(6) 1_555 1_555 1_555 no
C7 C23 C22 120.7(5) 1_555 1_555 1_555 no
C7 C23 HC23 119.7 1_555 1_555 1_555 no
C22 C23 HC23 119.7 1_555 1_555 1_555 no
C2T C1T C6T 116.7(12) 1_555 1_555 1_555 no
C2T C1T C7T 121.7(6) 1_555 1_555 1_555 no
C6T C1T C7T 121.7(6) 1_555 1_555 1_555 no
C1T C2T C3T 120.5(11) 1_555 1_555 1_555 no
C1T C2T HC2T 119.8 1_555 1_555 1_555 no
C3T C2T HC2T 119.8 1_555 1_555 1_555 no
C2T C3T C4T 121.2(13) 1_555 1_555 1_555 no
C2T C3T HC3T 119.4 1_555 1_555 1_555 no
C4T C3T HC3T 119.4 1_555 1_555 1_555 no
C3T C4T C5T 120.0(16) 1_555 1_555 1_555 no
C3T C4T HC4T 120.0 1_555 1_555 1_555 no
C5T C4T HC4T 120.0 1_555 1_555 1_555 no
C4T C5T C6T 121.2(14) 1_555 1_555 1_555 no
C4T C5T HC5T 119.4 1_555 1_555 1_555 no
C6T C5T HC5T 119.4 1_555 1_555 1_555 no
C1T C6T C5T 120.5(11) 1_555 1_555 1_555 no
C1T C6T HC6T 119.8 1_555 1_555 1_555 no
C5T C6T HC6T 119.8 1_555 1_555 1_555 no

# Attachment 'drb316.cif'

data_DRB316
_database_code_depnum_ccdc_archive 'CCDC 668454'
_audit_creation_method           'RAELSPUB and manual entry'

_computing_data_collection       'CAD4 Version 5.0, (Schagen et al, 1989)'
_computing_cell_refinement       'CAD4 Version 5.0, (Schagen et al, 1989)'
_computing_data_reduction        'Local program'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_computing_structure_refinement  'RAELS, (Rae, 1996)'
_computing_molecular_graphics    'ORTEP-II, (Johnson, 1976)'
_computing_publication_material  'Local programs'

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N4 O4,0.5(C7 H8)'
_chemical_formula_sum            'C26.5 H20 N4 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         458.5

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   11.192(6)
_cell_length_b                   17.811(6)
_cell_length_c                   11.205(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.81(3)
_cell_angle_gamma                90
_cell_volume                     2222(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10
_cell_measurement_theta_min      10
_cell_measurement_theta_max      11
_cell_measurement_temperature    294
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_exptl_crystal_size_rad          ?
_exptl_crystal_density_diffrn    1.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             956.0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

# EXPERIMENTAL DATA

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       \w--2\q
_diffrn_reflns_number            4105
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_theta_max         25
_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1.00
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         1
_diffrn_standards_interval_time  30min
_diffrn_standards_decay_%        6

# REFINEMENT DATA

_refine_special_details          ?
_reflns_number_total             3898
_reflns_number_gt                1266
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.062
_refine_ls_wR_factor_ref         0.064
_refine_ls_abs_structure_Flack   ?
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         1266
_refine_ls_number_parameters     165
_refine_ls_goodness_of_fit_ref   1.58
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[\s^2^(F) + 0.0004F^2^]'
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.76
_refine_diff_density_min         -0.92
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_atom_type_scat_source           
'International Tables for X-ray Crystallography, Vol. IV'

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
_atom_site_occupancy
O1 0.2146(7) 0.2313(5) 0.2244(9) 0.187(5) Uani O 1.0
O2 0.3210(7) 0.3208(5) 0.2264(10) 0.173(5) Uani O 1.0
O3 0.0998(6) 0.5550(4) 1.0526(6) 0.110(3) Uani O 1.0
O4 0.2312(6) 0.5383(5) 1.1956(6) 0.121(3) Uani O 1.0
N1 0.1976(5) 0.3010(3) 0.4854(5) 0.0446(8) Uani N 1.0
N2 0.2424(5) 0.4337(3) 0.9335(5) 0.0448(7) Uani N 1.0
N3 0.2299(8) 0.2953(5) 0.2422(6) 0.064(2) Uani N 1.0
N4 0.2040(7) 0.5490(4) 1.0918(7) 0.063(2) Uani N 1.0
C1 0.2737(7) 0.2615(4) 0.6835(7) 0.0502(8) Uani C 1.0
C2 0.1777(6) 0.3015(4) 0.6004(7) 0.0448(7) Uani C 1.0
C3 0.0810(7) 0.3394(4) 0.6444(7) 0.0478(8) Uani C 1.0
C4 0.0617(6) 0.3341(4) 0.7774(7) 0.055(1) Uani C 1.0
C5 0.1777(7) 0.3130(4) 0.8562(6) 0.0528(8) Uani C 1.0
C6 0.2655(6) 0.3778(4) 0.8601(6) 0.0438(7) Uani C 1.0
C7 0.3582(6) 0.3792(4) 0.7830(6) 0.0423(6) Uani C 1.0
C8 0.3838(6) 0.3126(4) 0.7070(7) 0.0484(9) Uani C 1.0
C9 0.2282(7) 0.2411(4) 0.8046(7) 0.0581(7) Uani C 1.0
C10 0.1187(7) 0.3400(4) 0.4080(6) 0.0455(8) Uani C 1.0
C11 0.1363(7) 0.3415(4) 0.2840(7) 0.050(1) Uani C 1.0
C12 0.0672(7) 0.3832(4) 0.2029(7) 0.057(1) Uani C 1.0
C13 -0.0282(7) 0.4253(4) 0.2417(7) 0.064(1) Uani C 1.0
C14 -0.0510(7) 0.4261(4) 0.3579(7) 0.062(1) Uani C 1.0
C15 0.0224(6) 0.3822(4) 0.4440(7) 0.0505(8) Uani C 1.0
C16 0.0047(6) 0.3800(4) 0.5669(7) 0.052(1) Uani C 1.0
C17 0.3140(6) 0.4958(4) 0.9322(6) 0.0418(7) Uani C 1.0
C18 0.2977(7) 0.5547(4) 1.0080(7) 0.0460(7) Uani C 1.0
C19 0.3638(6) 0.6193(4) 1.0164(6) 0.0486(7) Uani C 1.0
C20 0.4550(7) 0.6262(4) 0.9377(7) 0.0503(6) Uani C 1.0
C21 0.4754(6) 0.5704(4) 0.8607(6) 0.0479(7) Uani C 1.0
C22 0.4059(6) 0.5031(4) 0.8565(6) 0.0418(7) Uani C 1.0
C23 0.4270(6) 0.4426(4) 0.7819(6) 0.0429(7) Uani C 1.0
C1T 0.5479(12) 0.4694(8) 0.5029(11) 0.069(4) Uani C 0.5
C2T 0.4294(12) 0.4537(8) 0.4583(11) 0.072(4) Uani C 0.5
C3T 0.3392(12) 0.5081(9) 0.4552(11) 0.088(4) Uani C 0.5
C4T 0.3638(16) 0.5803(10) 0.4964(10) 0.097(5) Uani C 0.5
C5T 0.4808(15) 0.5969(8) 0.5409(11) 0.089(6) Uani C 0.5
C6T 0.5712(13) 0.5426(8) 0.5441(11) 0.078(4) Uani C 0.5
C7T 0.6444(15) 0.4113(11) 0.5063(15) 0.141(7) Uani C 0.5
HC1 0.2979 0.2145 0.6436 0.057 Uani H 1.0
H1C4 -0.0005 0.2949 0.7874 0.065 Uani H 1.0
H2C4 0.0329 0.3838 0.8044 0.058 Uani H 1.0
HC5 0.1574 0.3025 0.9395 0.061 Uani H 1.0
H1C8 0.4513 0.2830 0.7493 0.056 Uani H 1.0
H2C8 0.4077 0.3309 0.6284 0.049 Uani H 1.0
H1C9 0.2960 0.2213 0.8609 0.064 Uani H 1.0
H2C9 0.1638 0.2022 0.7924 0.066 Uani H 1.0
HC12 0.0836 0.3842 0.1168 0.063 Uani H 1.0
HC13 -0.0805 0.4553 0.1817 0.076 Uani H 1.0
HC14 -0.1184 0.4571 0.3836 0.072 Uani H 1.0
HC16 -0.0636 0.4081 0.5970 0.062 Uani H 1.0
HC19 0.3488 0.6596 1.0750 0.054 Uani H 1.0
HC20 0.5046 0.6730 0.9392 0.058 Uani H 1.0
HC21 0.5401 0.5762 0.8060 0.055 Uani H 1.0
HC23 0.4925 0.4458 0.7277 0.049 Uani H 1.0
HC2T 0.4086 0.4021 0.4278 0.113 Uani H 0.5
HC3T 0.2555 0.4947 0.4227 0.145 Uani H 0.5
HC4T 0.2992 0.6192 0.4941 0.157 Uani H 0.5
HC5T 0.5009 0.6486 0.5712 0.142 Uani H 0.5
HC6T 0.6548 0.5564 0.5768 0.126 Uani H 0.5
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
O1 0.123(7) 0.100(7) 0.345(9) -0.018(6) 0.062(8) -0.125(8) O
O2 0.094(6) 0.103(7) 0.341(9) -0.015(5) 0.113(8) -0.016(7) O
O3 0.059(4) 0.187(8) 0.083(5) 0.033(5) 0.003(4) 0.002(5) O
O4 0.104(6) 0.195(9) 0.063(5) -0.019(5) 0.009(5) 0.020(5) O
N1 0.045(2) 0.043(1) 0.0449(8) -0.0025(9) 0.0017(7) 0.002(1) N
N2 0.041(1) 0.048(1) 0.0452(8) -0.0022(9) 0.0023(7) 0.0003(8) N
N3 0.072(6) 0.063(6) 0.057(5) 0.006(6) 0.013(5) -0.015(5) N
N4 0.075(6) 0.067(6) 0.047(5) 0.005(5) -0.002(5) -0.018(5) N
C1 0.060(2) 0.0394(9) 0.049(1) 0.001(1) -0.005(1) 0.0018(9) C
C2 0.047(1) 0.0422(9) 0.0443(8) -0.0035(9) 0.0010(7) 0.0031(8) C
C3 0.043(1) 0.054(1) 0.0455(9) -0.006(1) 0.0026(7) -0.0006(9) C
C4 0.050(1) 0.069(2) 0.0464(9) -0.016(1) 0.0056(8) -0.004(1) C
C5 0.061(2) 0.053(1) 0.0440(8) -0.016(1) 0.0015(8) 0.0032(9) C
C6 0.045(1) 0.042(1) 0.0440(8) -0.0028(9) 0.0010(7) 0.0036(8) C
C7 0.042(1) 0.039(1) 0.0454(8) 0.0029(9) -0.0002(7) 0.0023(8) C
C8 0.049(1) 0.044(1) 0.051(1) 0.007(1) -0.0039(8) -0.003(1) C
C9 0.081(3) 0.043(1) 0.047(1) -0.013(1) -0.007(1) 0.0060(9) C
C10 0.046(1) 0.045(1) 0.0443(8) -0.0042(9) 0.0004(8) 0.0033(9) C
C11 0.054(2) 0.051(2) 0.0440(8) -0.011(1) 0.0007(8) 0.0034(9) C
C12 0.071(3) 0.052(3) 0.0463(9) -0.013(2) -0.007(1) 0.006(1) C
C13 0.078(3) 0.054(2) 0.055(1) 0.001(2) -0.020(2) 0.002(1) C
C14 0.063(2) 0.059(2) 0.058(1) 0.009(2) -0.017(2) -0.005(1) C
C15 0.047(1) 0.052(2) 0.049(1) 0.002(1) -0.0050(9) -0.001(1) C
C16 0.042(1) 0.062(2) 0.051(1) 0.001(1) -0.0018(8) -0.006(1) C
C17 0.039(1) 0.040(1) 0.0454(8) 0.0038(9) -0.0002(7) 0.0020(9) C
C18 0.041(1) 0.045(1) 0.0498(8) 0.008(1) -0.0030(7) -0.0025(9) C
C19 0.053(1) 0.039(1) 0.0510(9) 0.009(1) -0.0082(9) 0.0002(9) C
C20 0.063(2) 0.039(1) 0.0465(8) -0.003(1) -0.0065(8) 0.006(1) C
C21 0.055(1) 0.044(1) 0.0441(8) -0.007(1) -0.0009(7) 0.0049(9) C
C22 0.042(1) 0.039(1) 0.0439(8) 0.0005(9) 0.0003(7) 0.0041(9) C
C23 0.040(1) 0.043(1) 0.0450(8) 0.0003(9) 0.0018(7) 0.0012(9) C
C1T 0.081(6) 0.097(7) 0.037(7) -0.004(6) 0.036(6) 0.006(5) C
C2T 0.098(7) 0.088(8) 0.032(6) -0.020(6) 0.021(6) -0.001(6) C
C3T 0.082(7) 0.122(9) 0.061(7) -0.010(6) 0.008(7) 0.008(6) C
C4T 0.112(8) 0.106(7) 0.074(7) 0.019(7) 0.020(6) 0.012(7) C
C5T 0.130(8) 0.077(7) 0.062(9) -0.017(5) 0.024(9) 0.007(5) C
C6T 0.082(6) 0.102(7) 0.054(7) -0.031(6) 0.028(6) 0.010(7) C
C7T 0.128(8) 0.163(9) 0.137(9) 0.052(9) 0.043(9) -0.008(9) C

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.168(8) 1_555 1_555 no
O2 N3 1.146(8) 1_555 1_555 no
O3 N4 1.209(7) 1_555 1_555 no
O4 N4 1.188(7) 1_555 1_555 no
N1 C2 1.329(8) 1_555 1_555 no
N1 C10 1.364(8) 1_555 1_555 no
N2 C6 1.333(8) 1_555 1_555 no
N2 C17 1.367(8) 1_555 1_555 no
N3 C11 1.446(10) 1_555 1_555 no
N4 C18 1.480(9) 1_555 1_555 no
C1 C2 1.525(9) 1_555 1_555 no
C1 C8 1.534(9) 1_555 1_555 no
C1 C9 1.541(9) 1_555 1_555 no
C1 HC1 1.000 1_555 1_555 no
C2 C3 1.407(9) 1_555 1_555 no
C3 C4 1.530(9) 1_555 1_555 no
C3 C16 1.363(9) 1_555 1_555 no
C4 C5 1.541(9) 1_555 1_555 no
C4 H1C4 1.000 1_555 1_555 no
C4 H2C4 1.000 1_555 1_555 no
C5 C6 1.514(9) 1_555 1_555 no
C5 C9 1.536(9) 1_555 1_555 no
C5 HC5 1.000 1_555 1_555 no
C6 C7 1.416(8) 1_555 1_555 no
C7 C8 1.504(9) 1_555 1_555 no
C7 C23 1.368(8) 1_555 1_555 no
C8 H1C8 1.000 1_555 1_555 no
C8 H2C8 1.000 1_555 1_555 no
C9 H1C9 1.000 1_555 1_555 no
C9 H2C9 1.000 1_555 1_555 no
C10 C11 1.424(9) 1_555 1_555 no
C10 C15 1.406(9) 1_555 1_555 no
C11 C12 1.354(9) 1_555 1_555 no
C12 C13 1.409(10) 1_555 1_555 no
C12 HC12 1.000 1_555 1_555 no
C13 C14 1.352(10) 1_555 1_555 no
C13 HC13 1.000 1_555 1_555 no
C14 C15 1.434(9) 1_555 1_555 no
C14 HC14 1.000 1_555 1_555 no
C15 C16 1.411(9) 1_555 1_555 no
C16 HC16 1.000 1_555 1_555 no
C17 C18 1.374(9) 1_555 1_555 no
C17 C22 1.403(8) 1_555 1_555 no
C18 C19 1.365(9) 1_555 1_555 no
C19 C20 1.419(9) 1_555 1_555 no
C19 HC19 1.000 1_555 1_555 no
C20 C21 1.351(9) 1_555 1_555 no
C20 HC20 1.000 1_555 1_555 no
C21 C22 1.427(9) 1_555 1_555 no
C21 HC21 1.000 1_555 1_555 no
C22 C23 1.398(9) 1_555 1_555 no
C23 HC23 1.000 1_555 1_555 no
C1T C2T 1.398(5) 1_555 1_555 no
C1T C6T 1.398(5) 1_555 1_555 no
C1T C7T 1.493(8) 1_555 1_555 no
C2T C3T 1.398(9) 1_555 1_555 no
C2T HC2T 1.000 1_555 1_555 no
C3T C4T 1.384(8) 1_555 1_555 no
C3T HC3T 1.000 1_555 1_555 no
C4T C5T 1.384(8) 1_555 1_555 no
C4T HC4T 1.000 1_555 1_555 no
C5T C6T 1.398(9) 1_555 1_555 no
C5T HC5T 1.000 1_555 1_555 no
C6T HC6T 1.000 1_555 1_555 no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C10 116.8(6) 1_555 1_555 1_555 no
C6 N2 C17 116.5(7) 1_555 1_555 1_555 no
O1 N3 O2 118.6(10) 1_555 1_555 1_555 no
O1 N3 C11 120.8(9) 1_555 1_555 1_555 no
O2 N3 C11 120.7(9) 1_555 1_555 1_555 no
O3 N4 O4 120.8(9) 1_555 1_555 1_555 no
O3 N4 C18 118.9(7) 1_555 1_555 1_555 no
O4 N4 C18 120.3(8) 1_555 1_555 1_555 no
C2 C1 C8 109.4(6) 1_555 1_555 1_555 no
C2 C1 C9 111.9(6) 1_555 1_555 1_555 no
C2 C1 HC1 108.9 1_555 1_555 1_555 no
C8 C1 C9 108.7(6) 1_555 1_555 1_555 no
C8 C1 HC1 108.9 1_555 1_555 1_555 no
C9 C1 HC1 108.9 1_555 1_555 1_555 no
N1 C2 C1 114.3(7) 1_555 1_555 1_555 no
N1 C2 C3 123.6(7) 1_555 1_555 1_555 no
C1 C2 C3 122.0(7) 1_555 1_555 1_555 no
C2 C3 C4 120.1(7) 1_555 1_555 1_555 no
C2 C3 C16 119.1(7) 1_555 1_555 1_555 no
C4 C3 C16 120.8(7) 1_555 1_555 1_555 no
C3 C4 C5 112.3(6) 1_555 1_555 1_555 no
C3 C4 H1C4 108.7 1_555 1_555 1_555 no
C3 C4 H2C4 108.7 1_555 1_555 1_555 no
C5 C4 H1C4 108.7 1_555 1_555 1_555 no
C5 C4 H2C4 108.7 1_555 1_555 1_555 no
H1C4 C4 H2C4 109.5 1_555 1_555 1_555 no
C4 C5 C6 109.7(6) 1_555 1_555 1_555 no
C4 C5 C9 108.0(6) 1_555 1_555 1_555 no
C4 C5 HC5 108.8 1_555 1_555 1_555 no
C6 C5 C9 112.6(6) 1_555 1_555 1_555 no
C6 C5 HC5 108.8 1_555 1_555 1_555 no
C9 C5 HC5 108.8 1_555 1_555 1_555 no
N2 C6 C5 114.9(7) 1_555 1_555 1_555 no
N2 C6 C7 124.3(7) 1_555 1_555 1_555 no
C5 C6 C7 120.6(7) 1_555 1_555 1_555 no
C6 C7 C8 121.7(7) 1_555 1_555 1_555 no
C6 C7 C23 117.8(7) 1_555 1_555 1_555 no
C8 C7 C23 120.4(7) 1_555 1_555 1_555 no
C1 C8 C7 111.7(6) 1_555 1_555 1_555 no
C1 C8 H1C8 108.9 1_555 1_555 1_555 no
C1 C8 H2C8 108.9 1_555 1_555 1_555 no
C7 C8 H1C8 108.9 1_555 1_555 1_555 no
C7 C8 H2C8 108.9 1_555 1_555 1_555 no
H1C8 C8 H2C8 109.5 1_555 1_555 1_555 no
C1 C9 C5 107.6(6) 1_555 1_555 1_555 no
C1 C9 H1C9 109.9 1_555 1_555 1_555 no
C1 C9 H2C9 109.9 1_555 1_555 1_555 no
C5 C9 H1C9 109.9 1_555 1_555 1_555 no
C5 C9 H2C9 109.9 1_555 1_555 1_555 no
H1C9 C9 H2C9 109.5 1_555 1_555 1_555 no
N1 C10 C11 119.1(7) 1_555 1_555 1_555 no
N1 C10 C15 123.8(7) 1_555 1_555 1_555 no
C11 C10 C15 117.1(7) 1_555 1_555 1_555 no
N3 C11 C10 118.8(7) 1_555 1_555 1_555 no
N3 C11 C12 118.6(8) 1_555 1_555 1_555 no
C10 C11 C12 122.6(8) 1_555 1_555 1_555 no
C11 C12 C13 119.0(8) 1_555 1_555 1_555 no
C11 C12 HC12 120.5 1_555 1_555 1_555 no
C13 C12 HC12 120.5 1_555 1_555 1_555 no
C12 C13 C14 121.7(8) 1_555 1_555 1_555 no
C12 C13 HC13 119.2 1_555 1_555 1_555 no
C14 C13 HC13 119.2 1_555 1_555 1_555 no
C13 C14 C15 119.4(8) 1_555 1_555 1_555 no
C13 C14 HC14 120.3 1_555 1_555 1_555 no
C15 C14 HC14 120.3 1_555 1_555 1_555 no
C10 C15 C14 120.1(7) 1_555 1_555 1_555 no
C10 C15 C16 116.9(7) 1_555 1_555 1_555 no
C14 C15 C16 123.0(8) 1_555 1_555 1_555 no
C3 C16 C15 119.7(7) 1_555 1_555 1_555 no
C3 C16 HC16 120.1 1_555 1_555 1_555 no
C15 C16 HC16 120.1 1_555 1_555 1_555 no
N2 C17 C18 119.8(8) 1_555 1_555 1_555 no
N2 C17 C22 123.2(7) 1_555 1_555 1_555 no
C18 C17 C22 117.0(7) 1_555 1_555 1_555 no
N4 C18 C17 119.1(7) 1_555 1_555 1_555 no
N4 C18 C19 115.3(8) 1_555 1_555 1_555 no
C17 C18 C19 125.5(8) 1_555 1_555 1_555 no
C18 C19 C20 116.7(8) 1_555 1_555 1_555 no
C18 C19 HC19 121.7 1_555 1_555 1_555 no
C20 C19 HC19 121.7 1_555 1_555 1_555 no
C19 C20 C21 120.7(7) 1_555 1_555 1_555 no
C19 C20 HC20 119.6 1_555 1_555 1_555 no
C21 C20 HC20 119.6 1_555 1_555 1_555 no
C20 C21 C22 120.8(7) 1_555 1_555 1_555 no
C20 C21 HC21 119.6 1_555 1_555 1_555 no
C22 C21 HC21 119.6 1_555 1_555 1_555 no
C17 C22 C21 119.3(7) 1_555 1_555 1_555 no
C17 C22 C23 117.9(7) 1_555 1_555 1_555 no
C21 C22 C23 122.8(7) 1_555 1_555 1_555 no
C7 C23 C22 120.1(7) 1_555 1_555 1_555 no
C7 C23 HC23 119.9 1_555 1_555 1_555 no
C22 C23 HC23 119.9 1_555 1_555 1_555 no
C2T C1T C6T 116.3(14) 1_555 1_555 1_555 no
C2T C1T C7T 121.8(7) 1_555 1_555 1_555 no
C6T C1T C7T 121.8(7) 1_555 1_555 1_555 no
C1T C2T C3T 121.8(13) 1_555 1_555 1_555 no
C1T C2T HC2T 119.1 1_555 1_555 1_555 no
C3T C2T HC2T 119.1 1_555 1_555 1_555 no
C2T C3T C4T 121.2(15) 1_555 1_555 1_555 no
C2T C3T HC3T 119.4 1_555 1_555 1_555 no
C4T C3T HC3T 119.4 1_555 1_555 1_555 no
C3T C4T C5T 117.8(18) 1_555 1_555 1_555 no
C3T C4T HC4T 121.1 1_555 1_555 1_555 no
C5T C4T HC4T 121.1 1_555 1_555 1_555 no
C4T C5T C6T 121.2(15) 1_555 1_555 1_555 no
C4T C5T HC5T 119.4 1_555 1_555 1_555 no
C6T C5T HC5T 119.4 1_555 1_555 1_555 no
C1T C6T C5T 121.8(13) 1_555 1_555 1_555 no
C1T C6T HC6T 119.1 1_555 1_555 1_555 no
C5T C6T HC6T 119.1 1_555 1_555 1_555 no