# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_crystalstructure_4
#==============================================================================
# CHEMICAL DATA

_chemical_name_systematic        
;
 1,3-bis(4-nitrophenyl)urea with tetramethylammonium chloride
;
_chemical_formula_moiety         'C13 H10 N4 O5, C4 H12 N, Cl'
_chemical_formula_sum            'C17 H22 Cl N5 O5'
_chemical_formula_weight         411.85
_chemical_compound_source        'Isabelle Kirby'

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


#==============================================================================

# CRYSTAL DATA

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

_cell_length_a                   7.6033(2)
_cell_length_b                   11.4827(3)
_cell_length_c                   11.8705(4)
_cell_angle_alpha                83.1860(10)
_cell_angle_beta                 71.662(2)
_cell_angle_gamma                80.423(2)
_cell_volume                     967.59(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21504
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8708
_exptl_absorpt_correction_T_max  0.9541
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;

#==============================================================================

# EXPERIMENTAL DATA
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25085
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         55.40
_reflns_number_total             25085
_reflns_number_gt                18067
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         17926
_refine_ls_number_parameters     771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.038
_refine_ls_wR_factor_ref         0.029
_refine_ls_goodness_of_fit_ref   1.397
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.069
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        54.02
_diffrn_measured_fraction_theta_full 0.999
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#==============================================================================

# 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_occupancy
_atom_site_symmetry_multiplicity
CL(1) 1.203476(11) 0.123193(7) 0.095406(7) 0.017 1 2
O(1) 1.34356(6) 0.52927(3) -0.06468(4) 0.016 1 2
O(2) 0.63509(7) 0.81463(3) 0.38068(4) 0.022 1 2
O(3) 0.52597(6) 0.66088(4) 0.48646(4) 0.021 1 2
O(5) 2.09542(6) 0.31852(4) -0.53876(4) 0.022 1 2
O(4) 2.04066(6) 0.13495(5) -0.51531(5) 0.03 1 2
N(1) 0.63475(4) 0.70625(3) 0.39851(3) 0.014 1 2
N(2) 1.17874(5) 0.40552(3) 0.08537(3) 0.013 1 2
N(3) 1.42212(5) 0.32563(3) -0.06304(3) 0.013 1 2
N(5) 1.35971(5) 0.88271(3) -0.25479(3) 0.013 1 2
N(4) 2.00664(5) 0.23744(3) -0.48366(3) 0.018 1 2
C(1) 0.77089(4) 0.63022(3) 0.31345(3) 0.012 1 2
C(2) 0.78790(5) 0.50784(3) 0.34006(3) 0.014 1 2
C(3) 0.92491(5) 0.43631(3) 0.26149(3) 0.014 1 2
C(4) 1.04397(4) 0.48534(3) 0.15602(3) 0.011 1 2
C(5) 1.02093(5) 0.60871(3) 0.12942(3) 0.013 1 2
C(6) 0.88480(5) 0.68077(3) 0.20886(3) 0.014 1 2
C(7) 1.31752(4) 0.42987(3) -0.01893(3) 0.012 1 2
C(8) 1.56723(4) 0.31151(3) -0.16814(3) 0.012 1 2
C(9) 1.64695(5) 0.19346(3) -0.19231(4) 0.017 1 2
C(10) 1.78923(5) 0.16868(3) -0.29626(4) 0.018 1 2
C(11) 1.85558(5) 0.26323(3) -0.37520(3) 0.015 1 2
C(12) 1.78278(5) 0.38081(3) -0.35238(3) 0.015 1 2
C(13) 1.63666(5) 0.40528(3) -0.24908(3) 0.014 1 2
C(14) 1.29100(7) 0.96433(4) -0.15578(4) 0.02 1 2
C(15) 1.35746(8) 0.75779(4) -0.20220(5) 0.023 1 2
C(16) 1.23562(5) 0.90665(4) -0.33376(4) 0.018 1 2
C(17) 1.55514(5) 0.90030(4) -0.32698(4) 0.019 1 2
H(2) 0.695717 0.46949 0.420138 0.033 1 2
H(3) 0.945101 0.341349 0.281007 0.033 1 2
H(5) 1.109888 0.648712 0.048992 0.031 1 2
H(6) 0.865915 0.776015 0.19123 0.033 1 2
H(9) 1.598241 0.12038 -0.129943 0.037 1 2
H(10) 1.849349 0.078144 -0.315183 0.039 1 2
H(12) 1.841338 0.451949 -0.413835 0.034 1 2
H(13) 1.575612 0.495599 -0.229759 0.032 1 2
H(14A) 1.378913 0.943365 -0.100441 0.046 1 2
H(14B) 1.151142 0.952244 -0.108219 0.048 1 2
H(14C) 1.295868 1.052354 -0.193935 0.046 1 2
H(15A) 1.446717 0.742293 -0.147601 0.05 1 2
H(15B) 1.405042 0.702285 -0.273993 0.05 1 2
H(15C) 1.217815 0.74911 -0.150982 0.05 1 2
H(16A) 1.289161 0.847177 -0.402109 0.044 1 2
H(16B) 1.238426 0.995816 -0.368661 0.044 1 2
H(16C) 1.098893 0.892603 -0.280933 0.045 1 2
H(17A) 1.638374 0.883834 -0.268608 0.046 1 2
H(17B) 1.554493 0.9889 -0.363968 0.045 1 2
H(17C) 1.601529 0.840855 -0.395417 0.047 1 2
H(2A) 1.170294 0.318793 0.10896 0.033 1 2
H(3A) 1.375814 0.250567 -0.019047 0.04 1 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
CL(1) 0.01775(4) 0.01197(3) 0.01799(4) -0.00106(2) -0.00054(2) -0.00391(2)
O(1) 0.01673(13) 0.01121(12) 0.01662(13) 0.00174(10) -0.00217(11) -0.00134(10)
O(2) 0.02944(17) 0.01401(12) 0.01904(14) -0.00230(10) -0.00223(13) 0.00176(12)
O(3) 0.01950(13) 0.02189(14) 0.01915(13) -0.00571(11) 0.00267(11) -0.00693(12)
O(5) 0.01735(13) 0.02823(18) 0.01703(14) 0.00086(13) -0.00193(11) -0.00009(13)
O(4) 0.02052(15) 0.0332(2) 0.0328(2) -0.01866(17) 0.00286(14) -0.00515(14)
N(1) 0.01425(9) 0.01499(10) 0.01381(8) -0.00301(9) -0.00338(9) -0.00135(9)
N(2) 0.01531(11) 0.01024(10) 0.01327(11) -0.00055(9) -0.00213(9) -0.00177(9)
N(3) 0.01314(11) 0.01088(10) 0.01494(11) -0.00064(9) -0.00216(9) -0.00188(9)
N(5) 0.01356(11) 0.01105(10) 0.01298(11) -0.00078(8) -0.00339(9) -0.00117(9)
N(4) 0.01164(10) 0.02572(17) 0.01727(12) -0.00628(9) -0.00330(10) -0.00077(9)
C(1) 0.01280(10) 0.01260(11) 0.01220(10) -0.00118(8) -0.00384(8) -0.00194(9)
C(2) 0.01564(11) 0.01310(11) 0.01231(11) -0.00042(9) -0.00274(9) -0.00386(9)
C(3) 0.01642(12) 0.01114(10) 0.01262(11) 0.00015(8) -0.00339(9) -0.00329(9)
C(4) 0.01259(10) 0.01056(10) 0.01150(10) -0.00023(8) -0.00418(8) -0.00195(8)
C(5) 0.01422(11) 0.01111(10) 0.01274(10) 0.00072(8) -0.00295(9) -0.00123(9)
C(6) 0.01449(11) 0.01119(10) 0.01406(11) 0.00036(9) -0.00343(9) -0.00058(9)
C(7) 0.01225(10) 0.01053(10) 0.01283(10) 0.00013(8) -0.00400(9) -0.00150(8)
C(8) 0.01072(10) 0.01181(10) 0.01486(11) -0.00114(9) -0.00371(9) -0.00173(8)
C(9) 0.01389(11) 0.01224(11) 0.02135(14) -0.00253(10) -0.00179(11) -0.00212(9)
C(10) 0.01340(12) 0.01513(13) 0.02288(15) -0.00552(11) -0.00189(11)
-0.00162(10)
C(11) 0.01103(10) 0.01881(13) 0.01612(12) -0.00401(10) -0.00373(9) -0.00124(10)
C(12) 0.01274(11) 0.01733(13) 0.01426(11) -0.00013(10) -0.00348(9) -0.00146(10)
C(13) 0.01286(11) 0.01304(11) 0.01489(11) -0.00011(9) -0.00344(9) -0.00096(9)
C(14) 0.02351(16) 0.01790(14) 0.01642(13) -0.00518(11) -0.00138(12)
-0.00209(12)
C(15) 0.0328(2) 0.01237(13) 0.02669(18) 0.00295(12) -0.01481(17) -0.00519(13)
C(16) 0.01483(12) 0.02200(15) 0.01702(13) 0.00114(12) -0.00551(11) -0.00194(11)
C(17) 0.01298(12) 0.02362(16) 0.02027(14) -0.00461(13) -0.00266(11)
-0.00219(11)
H(2) 0.037328 0.029774 0.024296 0.001627 0.004094 -0.010594
H(3) 0.043373 0.016093 0.031697 0.002779 -0.002603 -0.004446
H(5) 0.035928 0.023235 0.025464 0.004164 0.002988 -0.006156
H(6) 0.042896 0.015953 0.032872 0.001448 -0.004474 0.001074
H(9) 0.036029 0.020677 0.041977 0.001498 0.003431 -0.005063
H(10) 0.036137 0.02331 0.047659 -0.010637 0.002063 0.001065
H(12) 0.034396 0.030232 0.029065 0.00534 0.001066 -0.005031
H(13) 0.03576 0.019538 0.031958 -0.001438 -0.000498 0.000222
H(14A) 0.055838 0.052378 0.037147 -0.012466 -0.024336 -0.001119
H(14B) 0.034252 0.061114 0.04041 -0.016185 0.008697 -0.011143
H(14C) 0.065975 0.02122 0.045739 -0.004373 -0.009156 -0.003064
H(15A) 0.069415 0.036976 0.060087 0.011177 -0.045883 -0.008572
H(15B) 0.074349 0.025965 0.052098 -0.012738 -0.022711 -0.001146
H(15C) 0.04803 0.043189 0.054146 0.013252 -0.00849 -0.020992
H(16A) 0.0458 0.053311 0.035937 -0.018404 -0.017377 0.002396
H(16B) 0.052072 0.033045 0.051247 0.014361 -0.026107 -0.00645
H(16C) 0.022402 0.068632 0.041408 0.00423 -0.00597 -0.012559
H(17A) 0.031181 0.066171 0.046162 -0.00341 -0.020916 -0.006394
H(17B) 0.039406 0.03727 0.051194 0.009901 -0.00422 -0.01352
H(17C) 0.03472 0.058906 0.04348 -0.028135 0.000672 -0.002138
H(2A) 0.037399 0.014613 0.037621 0.001157 0.003864 -0.005771
H(3A) 0.048162 0.016576 0.038394 0.003261 0.009821 -0.003944


#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
CL(1) 7.34(4) 0 0.042(12) 0.059(12) 0.034(12) 0.005(13) 0.018(13) 0.041(12)
0.063(13) -0.038(13) -0.012(11) -0.025(10) -0.041(10) 0.009(10) 0.041(10)
0.070(10) 0.032(10) 0.040(12) -0.018(11) -0.019(10) -0.007(11) 0.000(11)
0.011(11) 0.026(11) 0.017(11) -0.030(11) 1.045(3) 1 1 1 1 1 4 4.2587714285714 4
4.2587714285714 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714
O(1) 6.37(4) 0 -0.072(12) -0.001(10) -0.002(11) -0.056(12) 0.021(11) -0.012(11)
-0.054(11) -0.006(11) -0.013(9) 0.011(9) 0.015(9) 0.007(8) 0.012(8) 0.027(8)
0.006(8) 0.017(12) 0.017(11) -0.017(11) 0.008(11) 0.001(11) 0.000(10) 0.010(10)
-0.012(10) 0.003(10) 0.987(3) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(2) 6.34(2) 0 -0.043(10) -0.007(9) 0.016(9) -0.054(11) -0.005(9) -0.029(9)
-0.088(10) 0.024(9) 0.013(8) 0.002(8) -0.013(7) 0.019(7) -0.007(7) 0.063(7)
0.017(7) 0.007(10) 0.006(9) -0.011(9) -0.011(9) 0.004(9) 0.002(8) 0.001(8)
0.027(8) 0.011(8) 0.9948(17) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(3) 6.3446 0 -0.0426 -0.0073 0.0156 -0.0535 -0.0052 -0.0286 -0.0884 0.0239
0.0125 0.0023 -0.0132 0.0188 -0.0067 0.0632 0.0173 0.0073 0.0059 -0.0112
-0.0106 0.0039 0.0021 0.0005 0.0267 0.0111 0.9948(17) 1 1 1 1 1 2 4.466 2 4.466
2 4.466 3 4.466 4 4.466
O(5) 6.2973 0 -0.0134 0.0164 0.0868 -0.0203 -0.0009 0.0167 -0.1068 0.0111
-0.0451 0.0864 0.0534 0.015 0.0787 0.0366 0.0266 -0.0111 -0.0267 -0.0026
-0.0033 0 0.0071 0.007 0.0172 0.0053 0.9948(17) 1 1 1 1 1 2 4.466 2 4.466 2
4.466 3 4.466 4 4.466
O(4) 6.30(2) 0 -0.013(12) 0.016(10) 0.087(9) -0.020(12) -0.001(10) 0.017(10)
-0.107(11) 0.011(11) -0.045(8) 0.086(8) 0.053(8) 0.015(7) 0.079(7) 0.037(8)
0.027(8) -0.011(11) -0.027(9) -0.003(9) -0.003(10) 0.000(10) 0.007(9) 0.007(9)
0.017(10) 0.005(9) 0.9948(17) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
N(1) 4.87(4) 0 0 0 0.042(12) 0.064(12) 0 0 -0.133(13) 0 0.192(12) 0 0 0.138(12)
0 0 0 0.036(15) 0 0 0.017(15) 0 0 0 0.013(13) 0 1.010(3) 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(2) 5.33(4) 0 -0.048(12) -0.027(12) 0.001(11) -0.019(12) -0.018(11) -0.003(10)
-0.016(11) 0.020(11) -0.002(10) 0.008(10) 0.030(10) -0.010(10) 0.005(10)
0.185(10) 0.047(10) 0.034(13) 0.005(12) 0.020(12) -0.005(12) -0.005(12)
0.006(12) -0.001(12) -0.008(12) -0.009(12) 0.997(3) 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(3) 5.32(4) 0 -0.031(11) -0.025(12) 0.006(11) -0.012(11) -0.030(11) 0.016(10)
-0.010(11) 0.030(11) 0.014(10) 0.001(10) 0.010(10) 0.029(10) -0.015(10)
0.190(10) 0.043(9) 0.052(13) -0.022(12) -0.035(12) 0.014(12) -0.010(12)
-0.019(12) -0.017(12) -0.023(12) -0.020(12) 0.997(3) 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(5) 5.36(5) 0 0.000(11) 0.012(11) -0.012(10) -0.002(11) 0.010(10) -0.020(10)
-0.021(10) -0.009(10) 0.198(10) -0.005(10) 0.004(10) 0.000(10) -0.006(10)
0.000(9) -0.166(9) 0.020(13) 0.002(12) -0.018(12) -0.007(12) -0.008(12)
-0.012(12) 0.056(12) 0.008(12) 0.005(11) 0.988(4) 1 1 1 1 1 2 3.83936 2 3.83936
2 3.83936 3 3.83936 4 3.83936
N(4) 4.96(4) 0 0 0 0.003(14) 0.079(13) 0 0 -0.157(15) 0 0.222(13) 0 0 0.164(14)
0 0 0 0.056(17) 0 0 -0.018(17) 0 0 0 0.017(15) 0 1.010(3) 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
C(1) 4.03(3) 0 0.060(14) 0.121(14) -0.012(13) -0.089(13) 0.026(12) 0.019(12)
0.060(13) -0.096(13) -0.012(14) 0.017(13) 0.008(13) -0.008(13) -0.003(13)
0.286(14) 0.019(13) 0 0 0 0 0 0 0 0 0 1.027(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(2) 4.08(4) 0 0.016(15) -0.018(15) 0.012(13) -0.191(13) -0.003(13) 0.003(12)
-0.003(13) 0.009(14) -0.007(14) 0.019(14) 0.031(13) 0.004(13) 0.000(13)
0.236(14) -0.008(14) 0 0 0 0 0 0 0 0 0 1.027(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(3) 4.08(4) 0 -0.005(14) 0.010(15) 0.000(13) -0.157(13) -0.001(12) -0.002(12)
-0.004(13) -0.003(13) -0.005(14) 0.011(13) 0.036(13) -0.011(13) -0.001(13)
0.244(14) -0.002(14) 0 0 0 0 0 0 0 0 0 1.027(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(4) 3.91(3) 0 0.046(14) 0.060(14) -0.010(12) -0.171(13) -0.029(12) -0.008(12)
0.013(13) -0.056(13) 0.006(13) 0.005(13) 0.023(13) 0.008(13) -0.004(13)
0.278(14) 0.018(14) 0 0 0 0 0 0 0 0 0 1.027(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(5) 3.98(4) 0 0.014(15) -0.021(14) 0.003(13) -0.167(13) 0.027(12) 0.009(12)
0.015(13) 0.018(13) 0.010(14) 0.017(13) 0.027(13) -0.006(13) 0.000(13)
0.260(14) -0.009(13) 0 0 0 0 0 0 0 0 0 1.027(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(6) 4.03(4) 0 -0.023(15) 0.006(15) 0.001(13) -0.188(13) 0.013(12) 0.000(12)
-0.014(13) 0.008(13) -0.016(14) 0.003(13) 0.028(13) -0.002(13) 0.017(13)
0.226(14) -0.019(13) 0 0 0 0 0 0 0 0 0 1.027(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(7) 3.73(6) 0 -0.002(12) -0.019(14) 0.120(15) 0.222(15) -0.024(12) 0.003(13)
-0.102(13) -0.007(12) 0.284(17) 0.000(14) 0.005(15) 0.211(15) -0.007(14)
0.005(13) -0.007(13) 0 0 0 0 0 0 0 0 0 1.035(7) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(8) 3.93(4) 0 0.030(14) 0.060(14) 0.000(13) -0.167(13) -0.012(12) -0.003(12)
0.011(13) -0.066(13) 0.024(14) 0.005(13) 0.014(13) 0.003(14) 0.004(13)
0.288(15) 0.023(14) 0 0 0 0 0 0 0 0 0 1.028(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(9) 4.05(4) 0 0.002(15) 0.023(15) -0.007(13) -0.149(14) -0.022(13) -0.007(13)
0.005(14) 0.021(14) 0.008(15) 0.013(14) 0.044(14) 0.002(14) -0.025(14)
0.254(15) 0.020(14) 0 0 0 0 0 0 0 0 0 1.028(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(10) 4.06(4) 0 0.023(16) 0.008(16) -0.003(13) -0.201(15) 0.001(14) 0.010(13)
0.011(15) -0.011(15) 0.009(15) 0.032(15) 0.033(14) 0.001(15) 0.006(14)
0.273(16) -0.015(15) 0 0 0 0 0 0 0 0 0 1.028(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(11) 3.99(4) 0 0.064(15) 0.061(15) 0.000(13) -0.088(14) 0.009(13) 0.029(12)
0.053(14) -0.107(14) 0.020(14) -0.011(14) 0.038(13) -0.002(14) 0.008(14)
0.232(16) 0.002(15) 0 0 0 0 0 0 0 0 0 1.028(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(12) 3.98(4) 0 0.052(15) -0.003(16) 0.008(13) -0.190(14) 0.016(13) 0.001(13)
0.021(14) 0.021(15) 0.017(14) -0.011(14) 0.045(13) 0.019(14) -0.014(14)
0.267(15) 0.009(14) 0 0 0 0 0 0 0 0 0 1.028(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(13) 3.99(4) 0 -0.030(15) -0.001(15) -0.002(13) -0.152(13) 0.011(12)
-0.015(12) -0.011(13) 0.030(14) 0.000(14) 0.032(13) 0.030(13) 0.008(13)
0.003(13) 0.247(14) -0.016(14) 0 0 0 0 0 0 0 0 0 1.028(2) 1 1 1 1 1 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
C(14) 3.91(6) 0 -0.015(18) 0.011(18) -0.081(14) -0.130(15) -0.022(14)
-0.005(14) 0.009(15) 0.031(15) 0.220(16) 0.010(14) -0.017(14) -0.009(15)
0.011(15) 0.007(14) -0.156(15) 0 0 0 0 0 0 0 0 0 1.045(5) 1 1 1 1 1 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
C(15) 3.85(6) 0 -0.07(2) 0.034(18) -0.041(15) -0.090(15) 0.019(15) 0.016(14)
-0.039(16) 0.012(17) 0.196(17) 0.016(15) -0.032(14) -0.004(15) -0.023(16)
0.000(15) -0.102(16) 0 0 0 0 0 0 0 0 0 1.045(5) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(16) 3.95(6) 0 -0.019(17) -0.030(17) -0.087(14) -0.076(14) 0.019(13)
-0.015(13) 0.006(14) 0.011(14) 0.218(16) 0.021(14) 0.018(14) -0.016(14)
-0.017(14) 0.019(13) -0.168(15) 0 0 0 0 0 0 0 0 0 1.045(5) 1 1 1 1 1 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
C(17) 3.90(6) 0 0.021(17) -0.039(18) -0.077(15) -0.129(15) -0.004(13) 0.015(14)
0.030(15) -0.037(15) 0.220(16) 0.000(14) 0.000(14) -0.009(14) 0.004(15)
0.019(14) -0.174(15) 0 0 0 0 0 0 0 0 0 1.045(5) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
H(2) 0.88(2) 0 0 0 0.139(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.85(2) 0 0 0 0.135(15) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5) 0.81(2) 0 0 0 0.163(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6) 0.85(2) 0 0 0 0.129(15) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9) 0.80(2) 0 0 0 0.174(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10) 0.83(2) 0 0 0 0.132(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(12) 0.86(2) 0 0 0 0.130(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(13) 0.84(2) 0 0 0 0.164(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14A) 0.97(3) 0 0 0 0.144(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14B) 0.95(3) 0 0 0 0.093(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14C) 0.91(2) 0 0 0 0.133(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15A) 0.97(3) 0 0 0 0.116(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15B) 0.96(3) 0 0 0 0.10(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15C) 1.02(3) 0 0 0 0.18(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16A) 0.98(3) 0 0 0 0.130(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16B) 0.94(3) 0 0 0 0.106(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16C) 0.93(2) 0 0 0 0.136(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17A) 0.92(2) 0 0 0 0.109(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17B) 0.98(3) 0 0 0 0.136(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17C) 0.95(2) 0 0 0 0.129(18) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2A) 0.77(2) 0 0 0 0.097(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3A) 0.76(2) 0 0 0 0.124(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) H(3A) Z CL(1) H(2A) Y
O(1) C(7) X O(1) C(13) Y
O(2) N(1) X O(2) O(3) Y
O(3) N(1) -X O(3) O(2) Y
O(5) N(4) -X O(5) O(4) Y
O(4) N(4) X O(4) O(5) Y
N(1) C(1) Z N(1) O(2) Y
N(2) C(4) X N(2) C(7) Y
N(3) C(8) X N(3) C(7) Y
N(5) C(15) Z N(5) C(16) Y
N(4) C(11) Z N(4) O(4) Y
C(1) C(6) X C(1) C(2) Y
C(2) C(3) X C(2) C(1) Y
C(3) C(4) X C(3) C(2) Y
C(4) C(3) X C(4) C(5) Y
C(5) C(6) X C(5) C(4) Y
C(6) C(1) X C(6) C(5) Y
C(7) O(1) Z C(7) N(3) Y
C(8) C(9) X C(8) C(13) Y
C(9) C(10) X C(9) C(8) Y
C(10) C(11) X C(10) C(9) Y
C(11) C(12) X C(11) C(10) Y
C(12) C(13) X C(12) C(11) Y
C(13) C(8) X C(13) C(12) Y
C(14) N(5) Z C(14) H(14B) Y
C(15) N(5) Z C(15) H(15A) Y
C(16) N(5) Z C(16) H(16A) Y
C(17) N(5) Z C(17) H(17B) Y
H(2) C(2) Z H(2) C(3) Y
H(3) C(3) Z H(3) C(2) Y
H(5) C(5) Z H(5) C(6) Y
H(6) C(6) Z H(6) C(5) Y
H(9) C(9) Z H(9) C(10) Y
H(10) C(10) Z H(10) C(9) Y
H(12) C(12) Z H(12) C(13) Y
H(13) C(13) Z H(13) C(12) Y
H(14A) C(14) Z H(14A) H(14C) Y
H(14B) C(14) Z H(14B) H(14C) Y
H(14C) C(14) Z H(14C) H(14A) Y
H(15A) C(15) Z H(15A) H(15C) Y
H(15B) C(15) Z H(15B) H(15C) Y
H(15C) C(15) Z H(15C) H(15A) Y
H(16A) C(16) Z H(16A) H(16B) Y
H(16B) C(16) Z H(16B) H(16A) Y
H(16C) C(16) Z H(16C) H(16B) Y
H(17A) C(17) Z H(17A) H(17C) Y
H(17B) C(17) Z H(17B) H(17C) Y
H(17C) C(17) Z H(17C) H(17B) Y
H(2A) N(2) Z H(2A) C(7) Y
H(3A) N(3) Z H(3A) C(7) Y


#----------------------------------------------------------------------------#
#                   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
O(1) C(7) 1.2237(5) 1_555 1_555 yes
O(2) N(1) 1.2377(5) 1_555 1_555 yes
O(3) N(1) 1.2314(5) 1_555 1_555 yes
O(5) N(4) 1.2398(6) 1_555 1_555 yes
O(4) N(4) 1.2392(6) 1_555 1_555 yes
N(1) C(1) 1.4505(5) 1_555 1_555 yes
N(2) C(4) 1.3865(4) 1_555 1_555 yes
N(2) C(7) 1.3851(4) 1_555 1_555 yes
N(2) H(2A) 1.0090(3) 1_555 1_555 yes
N(3) C(7) 1.3817(4) 1_555 1_555 yes
N(3) C(8) 1.3866(5) 1_555 1_555 yes
N(3) H(3A) 1.0090(3) 1_555 1_555 yes
N(4) C(11) 1.4530(5) 1_555 1_555 yes
C(1) C(2) 1.3969(5) 1_555 1_555 yes
C(1) C(6) 1.3957(4) 1_555 1_555 yes
C(2) C(3) 1.3840(5) 1_555 1_555 yes
C(2) H(2) 1.0830(3) 1_555 1_555 yes
C(3) C(4) 1.4119(4) 1_555 1_555 yes
C(3) H(3) 1.0830(3) 1_555 1_555 yes
C(4) C(5) 1.4082(4) 1_555 1_555 yes
C(5) C(6) 1.3897(5) 1_555 1_555 yes
C(5) H(5) 1.0830(3) 1_555 1_555 yes
C(6) H(6) 1.0830(3) 1_555 1_555 yes
C(8) C(9) 1.4130(5) 1_555 1_555 yes
C(8) C(13) 1.4092(5) 1_555 1_555 yes
C(9) C(10) 1.3837(5) 1_555 1_555 yes
C(9) H(9) 1.0830(4) 1_555 1_555 yes
C(10) C(11) 1.3981(6) 1_555 1_555 yes
C(10) H(10) 1.0830(4) 1_555 1_555 yes
C(11) C(12) 1.3951(5) 1_555 1_555 yes
C(12) C(13) 1.3920(5) 1_555 1_555 yes
C(12) H(12) 1.0830(4) 1_555 1_555 yes
C(13) H(13) 1.0830(3) 1_555 1_555 yes
C(14) H(14A) 1.0590(5) 1_555 1_555 yes
C(14) H(14B) 1.0590(5) 1_555 1_555 yes
C(14) H(14C) 1.0590(4) 1_555 1_555 yes
C(15) H(15A) 1.0590(5) 1_555 1_555 yes
C(15) H(15B) 1.0590(5) 1_555 1_555 yes
C(15) H(15C) 1.0590(6) 1_555 1_555 yes
C(16) H(16A) 1.0590(4) 1_555 1_555 yes
C(16) H(16B) 1.0590(4) 1_555 1_555 yes
C(16) H(16C) 1.0590(4) 1_555 1_555 yes
C(17) H(17A) 1.0590(4) 1_555 1_555 yes
C(17) H(17B) 1.0590(5) 1_555 1_555 yes
C(17) H(17C) 1.0590(4) 1_555 1_555 yes

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
O(2) N(1) O(3) 122.54(4) 1_555 1_555 1_555 yes
O(2) N(1) C(1) 118.37(3) 1_555 1_555 1_555 yes
O(3) N(1) C(1) 119.08(3) 1_555 1_555 1_555 yes
C(4) N(2) C(7) 127.88(3) 1_555 1_555 1_555 yes
C(4) N(2) H(2A) 116.67(3) 1_555 1_555 1_555 yes
C(7) N(2) H(2A) 115.29(3) 1_555 1_555 1_555 yes
C(7) N(3) C(8) 127.90(3) 1_555 1_555 1_555 yes
C(7) N(3) H(3A) 115.60(3) 1_555 1_555 1_555 yes
C(8) N(3) H(3A) 115.93(3) 1_555 1_555 1_555 yes
O(5) N(4) O(4) 123.62(5) 1_555 1_555 1_555 yes
O(5) N(4) C(11) 118.42(4) 1_555 1_555 1_555 yes
O(4) N(4) C(11) 117.96(4) 1_555 1_555 1_555 yes
N(1) C(1) C(2) 118.87(3) 1_555 1_555 1_555 yes
N(1) C(1) C(6) 119.51(3) 1_555 1_555 1_555 yes
C(2) C(1) C(6) 121.60(3) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 118.53(3) 1_555 1_555 1_555 yes
C(1) C(2) H(2) 120.90(3) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 120.56(3) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 120.98(3) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 120.40(3) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 118.60(3) 1_555 1_555 1_555 yes
N(2) C(4) C(3) 115.96(3) 1_555 1_555 1_555 yes
N(2) C(4) C(5) 124.54(3) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.49(3) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 119.58(3) 1_555 1_555 1_555 yes
C(4) C(5) H(5) 121.09(3) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 119.32(3) 1_555 1_555 1_555 yes
C(1) C(6) C(5) 119.78(3) 1_555 1_555 1_555 yes
C(1) C(6) H(6) 119.20(3) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 121.01(3) 1_555 1_555 1_555 yes
O(1) C(7) N(2) 124.78(3) 1_555 1_555 1_555 yes
O(1) C(7) N(3) 125.22(3) 1_555 1_555 1_555 yes
N(2) C(7) N(3) 110.00(3) 1_555 1_555 1_555 yes
N(3) C(8) C(9) 115.72(3) 1_555 1_555 1_555 yes
N(3) C(8) C(13) 124.56(3) 1_555 1_555 1_555 yes
C(9) C(8) C(13) 119.73(3) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 120.69(3) 1_555 1_555 1_555 yes
C(8) C(9) H(9) 120.80(3) 1_555 1_555 1_555 yes
C(10) C(9) H(9) 118.51(3) 1_555 1_555 1_555 yes
C(9) C(10) C(11) 118.48(3) 1_555 1_555 1_555 yes
C(9) C(10) H(10) 120.68(4) 1_555 1_555 1_555 yes
C(11) C(10) H(10) 120.83(3) 1_555 1_555 1_555 yes
N(4) C(11) C(10) 118.56(3) 1_555 1_555 1_555 yes
N(4) C(11) C(12) 119.32(3) 1_555 1_555 1_555 yes
C(10) C(11) C(12) 122.12(3) 1_555 1_555 1_555 yes
C(11) C(12) C(13) 119.23(3) 1_555 1_555 1_555 yes
C(11) C(12) H(12) 120.11(3) 1_555 1_555 1_555 yes
C(13) C(12) H(12) 120.65(3) 1_555 1_555 1_555 yes
C(8) C(13) C(12) 119.71(3) 1_555 1_555 1_555 yes
C(8) C(13) H(13) 119.38(3) 1_555 1_555 1_555 yes
C(12) C(13) H(13) 120.91(3) 1_555 1_555 1_555 yes
H(14A) C(14) H(14B) 111.30(4) 1_555 1_555 1_555 yes
H(14A) C(14) H(14C) 110.95(4) 1_555 1_555 1_555 yes
H(14B) C(14) H(14C) 109.90(4) 1_555 1_555 1_555 yes
H(15A) C(15) H(15B) 111.74(5) 1_555 1_555 1_555 yes
H(15A) C(15) H(15C) 110.67(4) 1_555 1_555 1_555 yes
H(15B) C(15) H(15C) 111.67(4) 1_555 1_555 1_555 yes
H(16A) C(16) H(16B) 111.50(4) 1_555 1_555 1_555 yes
H(16A) C(16) H(16C) 111.13(4) 1_555 1_555 1_555 yes
H(16B) C(16) H(16C) 110.95(4) 1_555 1_555 1_555 yes
H(17A) C(17) H(17B) 110.21(4) 1_555 1_555 1_555 yes
H(17A) C(17) H(17C) 111.79(4) 1_555 1_555 1_555 yes
H(17B) C(17) H(17C) 110.31(4) 1_555 1_555 1_555 yes

_database_code_depnum_ccdc_archive 'CCDC 953241'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_crystalstructure_5
#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 1,3-bis(4-nitrophenyl)urea with tetramethylammonium acetate
;
_chemical_formula_moiety         'C13 H10 N4 O5, C4 H12 N, C2 H3 O2'
_chemical_formula_sum            'C19 H25 N5 O7'
_chemical_formula_weight         435.44
_chemical_compound_source        'Isabelle Kirby'
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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.797(2)
_cell_length_b                   11.214(3)
_cell_length_c                   12.211(3)
_cell_angle_alpha                91.753(5)
_cell_angle_beta                 104.560(7)
_cell_angle_gamma                95.232(13)
_cell_volume                     1027.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8541
_cell_measurement_theta_min      23.4
_cell_measurement_theta_max      61.4

_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
        ?
;
_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    'confocal mirrors, HF Varimax'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_reflns_number            147512
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         61.56
_reflns_number_total             31289
_reflns_number_gt                26198
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         22116
_refine_ls_number_parameters     851
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.08
_refine_ls_R_factor_gt           0.053
_refine_ls_wR_factor_ref         0.061
_refine_ls_goodness_of_fit_ref   1.645
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.068
_diffrn_measured_fraction_theta_max 0.666
_diffrn_reflns_theta_full        54.71
_diffrn_measured_fraction_theta_full 0.959

#==============================================================================

# 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_occupancy
_atom_site_symmetry_multiplicity
O(1) 0.07620(6) 0.53099(4) 0.37724(4) 0.015 1 2
O(4) 0.81013(9) 0.69740(6) 0.90729(5) 0.027 1 2
O(5) 0.69786(9) 0.84816(5) 0.81891(6) 0.025 1 2
O(3) -0.56579(8) 0.13477(5) -0.08250(5) 0.022 1 2
O(2) -0.58633(8) 0.32563(5) -0.09513(5) 0.023 1 2
O(6) 0.14861(9) 0.10001(5) 0.41463(5) 0.02 1 2
O(7) 0.33297(9) 0.19105(5) 0.57096(5) 0.021 1 2
N(1) -0.51651(5) 0.24010(3) -0.04732(3) 0.014 1 2
N(2) 0.04065(5) 0.32438(3) 0.34850(3) 0.012 1 2
N(3) 0.24771(5) 0.41269(3) 0.50285(3) 0.011 1 2
N(4) 0.70628(6) 0.73949(4) 0.82776(4) 0.016 1 2
N(5) 0.08825(5) 0.82070(4) 0.21065(4) 0.013 1 2
C(1) -0.37017(5) 0.26378(4) 0.05315(3) 0.012 1 2
C(2) -0.29623(6) 0.16742(4) 0.11147(4) 0.013 1 2
C(3) -0.15904(6) 0.19144(4) 0.20867(4) 0.013 1 2
C(4) -0.09499(5) 0.31075(3) 0.24983(3) 0.01 1 2
C(5) -0.17257(5) 0.40610(4) 0.18970(4) 0.013 1 2
C(6) -0.30926(5) 0.38231(4) 0.09170(4) 0.013 1 2
C(7) 0.11847(5) 0.43181(3) 0.40745(3) 0.011 1 2
C(8) 0.35466(5) 0.49930(3) 0.57979(3) 0.011 1 2
C(9) 0.47096(6) 0.45576(4) 0.67520(4) 0.013 1 2
C(10) 0.58707(6) 0.53379(4) 0.75594(4) 0.014 1 2
C(11) 0.58736(5) 0.65699(4) 0.74214(4) 0.012 1 2
C(12) 0.47404(6) 0.70230(4) 0.64950(4) 0.014 1 2
C(13) 0.35712(6) 0.62401(4) 0.56820(4) 0.013 1 2
C(14) -0.02466(7) 0.82087(5) 0.29408(4) 0.017 1 2
C(15) 0.27858(7) 0.85790(7) 0.27090(6) 0.023 1 2
C(16) 0.02674(9) 0.90720(5) 0.12131(5) 0.02 1 2
C(17) 0.07027(8) 0.69736(4) 0.15600(5) 0.018 1 2
C(18) 0.25435(5) 0.09900(4) 0.51167(4) 0.012 1 2
C(19) 0.29064(7) -0.02203(4) 0.56080(4) 0.017 1 2
H(2) -0.34969 0.076693 0.080226 0.034 1 2
H(3) -0.099237 0.11844 0.258122 0.029 1 2
H(5) -0.125515 0.498508 0.224406 0.032 1 2
H(6) -0.374521 0.455584 0.044919 0.03 1 2
H(9) 0.465676 0.358468 0.685695 0.04 1 2
H(10) 0.674916 0.500393 0.829735 0.032 1 2
H(12) 0.478942 0.797363 0.640012 0.025 1 2
H(13) 0.268036 0.658092 0.494806 0.04 1 2
H(14A) -0.161692 0.801343 0.249233 0.036 1 2
H(14B) -0.003885 0.910836 0.337211 0.032 1 2
H(14C) 0.019853 0.751692 0.355404 0.04 1 2
H(15A) 0.325135 0.794599 0.335676 0.044 1 2
H(15B) 0.285493 0.946231 0.310845 0.043 1 2
H(15C) 0.362273 0.859616 0.208669 0.057 1 2
H(16A) 0.105394 0.902094 0.058731 0.045 1 2
H(16B) 0.045618 0.996525 0.161837 0.046 1 2
H(16C) -0.113065 0.881338 0.079921 0.042 1 2
H(17A) 0.148133 0.69965 0.094386 0.039 1 2
H(17B) -0.067513 0.673156 0.114668 0.038 1 2
H(17C) 0.119779 0.636014 0.222578 0.038 1 2
H(19A) 0.371742 -0.067973 0.51517 0.052 1 2
H(19B) 0.167187 -0.079323 0.550845 0.048 1 2
H(19C) 0.358112 -0.012178 0.649387 0.043 1 2
H(2A) 0.085676 0.243774 0.378806 0.023 1 2
H(3A) 0.273639 0.324531 0.52176 0.028 1 2


#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(1) 6.18(3) 0 -0.091(14) 0.002(12) -0.025(13) -0.036(16) 0.023(15) 0.037(14)
-0.057(14) 0.024(14) -0.030(14) -0.011(13) -0.011(12) 0.032(13) 0.019(12)
0.012(12) -0.025(12) 0.016(18) -0.028(17) -0.014(16) 0.022(17) 0.053(16)
0.034(15) 0.013(16) -0.008(15) 0.002(14) 0.976373 1 1 1 1 1 2 4.466 2 4.466 2
4.466 3 4.466 4 4.466
O(4) 6.18(2) 0 -0.049(13) 0.017(12) 0.000(12) 0.015(16) 0.009(12) -0.033(13)
-0.098(13) 0.044(13) -0.028(13) -0.009(13) -0.011(12) 0.004(11) -0.008(11)
0.044(12) 0.045(12) 0.014(18) -0.005(15) -0.016(15) -0.002(16) -0.010(16)
-0.020(14) 0.013(13) 0.019(14) 0.013(14) 0.978355 1 1 1 1 1 2 4.466 2 4.466 2
4.466 3 4.466 4 4.466
O(5) 6.1822 0 -0.0486 0.0167 -0.0004 0.0146 0.0087 -0.0326 -0.0975 0.0443
-0.0283 -0.0088 -0.0114 0.0041 -0.0079 0.0436 0.0448 0.0142 -0.0054 -0.0161
-0.002 -0.0102 -0.0197 0.0127 0.0194 0.0126 0.978355 1 1 1 1 1 2 4.466 2 4.466
2 4.466 3 4.466 4 4.466
O(3) 6.1361 0 -0.0423 0.0243 -0.0174 -0.0015 -0.0088 -0.0052 -0.1388 -0.001
-0.0118 0.0909 -0.0121 0.0015 -0.0009 0.0308 0.0079 0.0003 0.0182 -0.0158
-0.0144 0.0047 -0.0197 0.0079 0.014 0.0013 0.978355 1 1 1 1 1 2 4.466 2 4.466 2
4.466 3 4.466 4 4.466
O(2) 6.136(19) 0 -0.042(11) 0.024(10) -0.017(12) -0.002(14) -0.009(12)
-0.005(12) -0.139(11) -0.001(12) -0.012(12) 0.091(12) -0.012(11) 0.002(10)
-0.001(10) 0.031(10) 0.008(10) 0.000(17) 0.018(14) -0.016(14) -0.014(14)
0.005(15) -0.020(13) 0.008(12) 0.014(12) 0.001(12) 0.978355 1 1 1 1 1 2 4.466 2
4.466 2 4.466 3 4.466 4 4.466
O(6) 6.39(3) 0 -0.060(14) -0.006(13) 0.029(16) -0.027(18) -0.020(17) 0.022(16)
-0.070(14) -0.023(15) 0.038(17) 0.048(15) 0.046(15) 0.019(14) -0.005(14)
0.033(13) 0.003(13) 0.01(2) 0.03(2) 0.040(19) 0.04(2) -0.021(19) -0.021(17)
-0.039(18) 0.040(16) 0.010(15) 0.963 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466
4 4.466
O(7) 6.34(3) 0 -0.001(15) 0.015(13) -0.010(17) -0.068(19) -0.034(17) -0.029(16)
-0.089(15) 0.009(15) 0.069(17) 0.070(16) 0.070(16) -0.014(15) -0.017(14)
0.058(13) -0.015(13) 0.00(2) 0.05(2) -0.01(2) -0.05(2) -0.006(19) 0.016(17)
-0.033(18) -0.002(16) -0.003(16) 0.963 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3
4.466 4 4.466
N(1) 5.07(3) 0 0 0 0.042(16) 0.057(16) 0 0 -0.193(16) 0 0.218(17) 0 0 0.176(17)
0 0 0 0.06(2) 0 0 0.00(2) 0 0 0 0.05(2) 0 0.97907 1 1 1 1 1 2 3.83936 2 3.83936
2 3.83936 3 3.83936 4 3.83936
N(2) 5.18(3) 0 -0.069(15) -0.048(15) 0.022(13) -0.038(15) 0.008(14) -0.017(13)
-0.031(14) 0.059(15) -0.006(15) 0.001(14) -0.010(14) 0.007(14) -0.010(14)
0.157(14) 0.029(14) 0.04(2) 0.028(18) 0.012(17) -0.009(18) -0.006(18)
-0.013(17) -0.033(18) 0.007(18) -0.002(18) 0.980877 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(3) 5.22(3) 0 -0.036(15) -0.095(15) 0.043(13) 0.003(15) -0.028(13) 0.043(13)
-0.082(14) 0.003(15) -0.030(15) -0.018(14) 0.042(14) 0.022(14) 0.014(14)
0.174(15) 0.049(14) 0.06(2) 0.043(17) -0.015(18) -0.018(18) -0.018(18)
0.034(17) 0.020(18) -0.024(18) -0.040(18) 0.980877 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(4) 5.03(3) 0 0 0 0.035(17) -0.012(17) 0 0 -0.205(18) 0 0.215(19) 0 0
0.221(19) 0 0 0 0.03(2) 0 0 -0.03(2) 0 0 0 0.00(2) 0 0.97907 1 1 1 1 1 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(5) 4.98(3) 0 0.017(14) -0.046(14) -0.005(14) -0.018(15) 0.055(14) -0.038(14)
-0.010(15) -0.017(15) 0.200(15) 0.015(15) 0.015(15) 0.012(15) -0.029(15)
0.027(15) -0.177(15) -0.01(2) 0.039(18) -0.062(19) 0.04(2) 0.014(19) 0.010(19)
0.021(19) 0.037(18) -0.007(18) 0.993748 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936
3 3.83936 4 3.83936
C(1) 4.04(4) 0 0.069(19) 0.078(18) 0.010(15) -0.086(17) -0.009(16) 0.012(15)
0.017(18) -0.079(19) -0.01(2) 0.004(18) 0.007(18) 0.024(19) -0.012(19) 0.25(2)
0.00(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(2) 4.21(5) 0 0.00(2) -0.05(2) 0.000(17) -0.154(18) -0.024(17) 0.022(16)
0.033(19) -0.08(2) -0.03(2) 0.002(19) 0.040(19) -0.02(2) 0.005(19) 0.22(2)
-0.01(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(3) 4.22(5) 0 -0.033(19) 0.00(2) -0.001(16) -0.155(18) -0.014(17) -0.011(16)
-0.076(18) 0.020(19) 0.00(2) -0.004(19) -0.033(19) -0.013(19) 0.028(19) 0.25(2)
-0.05(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(4) 4.00(4) 0 0.053(18) 0.019(18) -0.015(16) -0.179(17) 0.017(16) -0.016(16)
-0.049(18) -0.051(18) 0.04(2) 0.014(18) -0.007(19) -0.01(2) 0.010(19) 0.29(2)
0.01(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(5) 4.16(5) 0 0.031(19) -0.031(19) 0.002(16) -0.157(18) 0.023(16) 0.006(16)
0.022(18) -0.008(19) 0.04(2) -0.016(19) -0.004(18) 0.018(19) 0.039(19) 0.26(2)
0.01(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(6) 4.11(5) 0 -0.040(19) -0.013(19) 0.024(16) -0.194(18) 0.031(17) -0.025(16)
-0.092(18) 0.046(19) 0.01(2) 0.029(19) 0.024(18) 0.042(19) 0.024(19) 0.24(2)
-0.02(2) 0 0 0 0 0 0 0 0 0 0.978149 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(7) 3.97(4) 0 -0.012(16) 0.019(17) 0.079(18) 0.255(19) 0.010(16) -0.031(18)
-0.087(17) -0.016(16) 0.35(2) -0.06(2) 0.03(2) 0.25(2) 0.01(2) 0.012(18)
-0.010(19) 0 0 0 0 0 0 0 0 0 0.980648 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(8) 3.93(4) 0 0.029(18) 0.027(18) -0.018(15) -0.157(17) -0.053(16) 0.015(16)
0.076(18) -0.036(18) -0.01(2) -0.007(18) -0.019(19) -0.01(2) -0.009(19) 0.27(2)
0.06(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(9) 4.21(5) 0 0.003(19) -0.033(19) 0.026(16) -0.119(18) -0.002(17) 0.026(16)
-0.011(18) 0.023(19) -0.05(2) 0.026(19) 0.022(19) -0.032(19) -0.002(19) 0.24(2)
0.04(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(10) 3.93(5) 0 -0.07(2) 0.01(2) 0.021(16) -0.129(18) 0.026(17) -0.001(16)
-0.027(19) 0.05(2) 0.01(2) 0.02(2) 0.005(19) 0.01(2) 0.059(19) 0.21(2) 0.05(2)
0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(11) 4.00(4) 0 0.023(19) 0.092(18) -0.014(16) -0.080(18) 0.002(17) -0.040(16)
0.107(19) -0.132(19) 0.02(2) 0.018(19) 0.004(19) -0.027(19) 0.004(19) 0.23(2)
0.05(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(12) 4.10(5) 0 0.04(2) -0.01(2) -0.017(16) -0.216(18) 0.002(17) -0.018(17)
-0.021(19) -0.01(2) 0.01(2) 0.054(19) 0.004(19) -0.010(19) -0.02(2) 0.21(2)
-0.04(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(13) 4.03(5) 0 -0.043(19) -0.02(2) 0.025(16) -0.128(18) -0.015(16) -0.006(16)
-0.036(18) 0.048(19) -0.02(2) 0.030(19) 0.011(18) -0.01(2) 0.024(19) 0.24(2)
-0.02(2) 0 0 0 0 0 0 0 0 0 0.989938 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(14) 4.36(5) 0 -0.01(2) -0.01(2) -0.107(18) -0.115(19) -0.019(17) 0.033(18)
0.04(2) 0.020(19) 0.24(2) 0.021(19) 0.025(19) -0.02(2) 0.02(2) -0.050(18)
-0.21(2) 0 0 0 0 0 0 0 0 0 0.983624 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(15) 4.25(6) 0 -0.01(2) 0.10(3) -0.077(18) -0.144(19) -0.027(19) -0.10(2)
-0.03(2) -0.04(2) 0.28(2) -0.05(2) -0.06(2) 0.04(2) -0.02(2) -0.04(2) -0.25(2)
0 0 0 0 0 0 0 0 0 0.983624 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(16) 4.27(5) 0 -0.11(2) 0.03(2) -0.042(18) -0.109(19) 0.006(19) 0.025(19)
-0.03(2) 0.045(19) 0.22(2) 0.03(2) -0.02(2) 0.06(2) 0.04(2) 0.012(19) -0.24(2)
0 0 0 0 0 0 0 0 0 0.983624 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(17) 4.32(5) 0 -0.06(2) -0.03(2) -0.066(17) -0.146(19) 0.008(18) 0.041(18)
-0.030(19) 0.031(19) 0.24(2) 0.00(2) -0.04(2) -0.05(2) 0.01(2) 0.001(18)
-0.20(2) 0 0 0 0 0 0 0 0 0 0.983624 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(18) 4.03(4) 0 0.005(16) 0.011(18) -0.076(18) 0.098(18) -0.039(16) -0.089(19)
-0.194(18) 0.034(17) 0.27(2) 0.010(19) 0.01(2) 0.19(2) -0.05(2) 0.026(19)
-0.03(2) 0 0 0 0 0 0 0 0 0 0.978811 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(19) 4.41(5) 0 0.00(2) 0.08(2) -0.026(18) -0.003(19) -0.014(18) 0.023(18)
-0.041(18) -0.016(19) 0.27(2) 0.01(2) 0.02(2) 0.04(2) -0.05(2) -0.016(18)
-0.23(2) 0 0 0 0 0 0 0 0 0 0.980732 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
H(2) 0.84(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.83(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5) 0.82(3) 0 0 0 0.16(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6) 0.74(3) 0 0 0 0.15(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9) 0.78(3) 0 0 0 0.09(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10) 0.84(3) 0 0 0 0.14(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(12) 0.81(3) 0 0 0 0.09(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(13) 0.82(3) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14A) 0.79(3) 0 0 0 0.11(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14B) 0.79(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14C) 0.79(3) 0 0 0 0.07(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15A) 0.75(3) 0 0 0 0.01(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15B) 0.90(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15C) 0.92(3) 0 0 0 0.19(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16A) 0.92(3) 0 0 0 0.08(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16B) 0.76(3) 0 0 0 0.06(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16C) 0.89(3) 0 0 0 0.19(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17A) 0.91(3) 0 0 0 0.06(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17B) 0.84(3) 0 0 0 0.07(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17C) 0.84(3) 0 0 0 0.10(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(19A) 0.89(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(19B) 0.80(3) 0 0 0 0.08(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(19C) 0.82(3) 0 0 0 0.02(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2A) 0.66(2) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3A) 0.66(2) 0 0 0 0.037(19) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(7) X O(1) C(13) Y
O(4) N(4) X O(4) O(5) Y
O(5) N(4) -X O(5) O(4) Y
O(3) N(1) -X O(3) O(2) Y
O(2) N(1) X O(2) O(3) Y
O(6) C(18) X O(6) O(7) Y
O(7) C(18) X O(7) O(6) Y
N(1) C(1) Z N(1) O(2) Y
N(2) C(4) X N(2) C(7) Y
N(3) C(8) X N(3) C(7) Y
N(4) C(11) Z N(4) O(4) Y
N(5) C(15) Z N(5) C(16) Y
C(1) C(6) X C(1) C(2) Y
C(2) C(3) X C(2) C(1) Y
C(3) C(4) X C(3) C(2) Y
C(4) C(3) X C(4) C(5) Y
C(5) C(6) X C(5) C(4) Y
C(6) C(1) X C(6) C(5) Y
C(7) O(1) Z C(7) N(3) Y
C(8) C(9) X C(8) C(13) Y
C(9) C(10) X C(9) C(8) Y
C(10) C(11) X C(10) C(9) Y
C(11) C(12) X C(11) C(10) Y
C(12) C(13) X C(12) C(11) Y
C(13) C(8) X C(13) C(12) Y
C(14) N(5) Z C(14) H(14B) Y
C(15) N(5) Z C(15) H(15A) Y
C(16) N(5) Z C(16) H(16A) Y
C(17) N(5) Z C(17) H(17B) Y
C(18) C(19) Z C(18) O(6) Y
C(19) C(18) Z C(19) H(19B) Y
H(2) C(2) Z H(2) C(3) Y
H(3) C(3) Z H(3) C(2) Y
H(5) C(5) Z H(5) C(6) Y
H(6) C(6) Z H(6) C(5) Y
H(9) C(9) Z H(9) C(10) Y
H(10) C(10) Z H(10) C(9) Y
H(12) C(12) Z H(12) C(13) Y
H(13) C(13) Z H(13) C(12) Y
H(14A) C(14) Z H(14A) H(14C) Y
H(14B) C(14) Z H(14B) H(14C) Y
H(14C) C(14) Z H(14C) H(14A) Y
H(15A) C(15) Z H(15A) H(15C) Y
H(15B) C(15) Z H(15B) H(15C) Y
H(15C) C(15) Z H(15C) H(15A) Y
H(16A) C(16) Z H(16A) H(16B) Y
H(16B) C(16) Z H(16B) H(16A) Y
H(16C) C(16) Z H(16C) H(16B) Y
H(17A) C(17) Z H(17A) H(17C) Y
H(17B) C(17) Z H(17B) H(17C) Y
H(17C) C(17) Z H(17C) H(17B) Y
H(19A) C(19) Z H(19A) H(19B) Y
H(19B) C(19) Z H(19B) H(19A) Y
H(19C) C(19) Z H(19C) H(19B) Y
H(2A) N(2) Z H(2A) C(7) Y
H(3A) N(3) Z H(3A) C(7) Y


#----------------------------------------------------------------------------#
#                   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
O(1) C(7) 1.2299(6) 1_555 1_555 yes
O(4) N(4) 1.2344(7) 1_555 1_555 yes
O(5) N(4) 1.2330(7) 1_555 1_555 yes
O(3) N(1) 1.2372(6) 1_555 1_555 yes
O(2) N(1) 1.2357(6) 1_555 1_555 yes
O(6) C(18) 1.2631(6) 1_555 1_555 yes
O(7) C(18) 1.2574(6) 1_555 1_555 yes
N(1) C(1) 1.4486(5) 1_555 1_555 yes
N(2) C(4) 1.3827(5) 1_555 1_555 yes
N(2) C(7) 1.3898(5) 1_555 1_555 yes
N(2) H(2A) 1.0442(4) 1_555 1_555 yes
N(3) C(7) 1.3722(5) 1_555 1_555 yes
N(3) C(8) 1.3870(5) 1_555 1_555 yes
N(3) H(3A) 1.0481(4) 1_555 1_555 yes
N(4) C(11) 1.4512(6) 1_555 1_555 yes
C(1) C(2) 1.4006(6) 1_555 1_555 yes
C(1) C(6) 1.3957(6) 1_555 1_555 yes
C(2) C(3) 1.3838(6) 1_555 1_555 yes
C(2) H(2) 1.0832(4) 1_555 1_555 yes
C(3) C(4) 1.4152(5) 1_555 1_555 yes
C(3) H(3) 1.1003(4) 1_555 1_555 yes
C(4) C(5) 1.4111(5) 1_555 1_555 yes
C(5) C(6) 1.3880(5) 1_555 1_555 yes
C(5) H(5) 1.1017(4) 1_555 1_555 yes
C(6) H(6) 1.1042(4) 1_555 1_555 yes
C(8) C(9) 1.4151(5) 1_555 1_555 yes
C(8) C(13) 1.4089(5) 1_555 1_555 yes
C(9) C(10) 1.3825(6) 1_555 1_555 yes
C(9) H(9) 1.1006(4) 1_555 1_555 yes
C(10) C(11) 1.3967(6) 1_555 1_555 yes
C(10) H(10) 1.0856(4) 1_555 1_555 yes
C(11) C(12) 1.3904(6) 1_555 1_555 yes
C(12) C(13) 1.3903(6) 1_555 1_555 yes
C(12) H(12) 1.0742(4) 1_555 1_555 yes
C(13) H(13) 1.0900(4) 1_555 1_555 yes
C(14) H(14A) 1.0701(5) 1_555 1_555 yes
C(14) H(14B) 1.1029(5) 1_555 1_555 yes
C(14) H(14C) 1.1122(6) 1_555 1_555 yes
C(15) H(15A) 1.0947(9) 1_555 1_555 yes
C(15) H(15B) 1.0814(7) 1_555 1_555 yes
C(15) H(15C) 1.1187(7) 1_555 1_555 yes
C(16) H(16A) 1.0967(7) 1_555 1_555 yes
C(16) H(16B) 1.0845(6) 1_555 1_555 yes
C(16) H(16C) 1.0881(7) 1_555 1_555 yes
C(17) H(17A) 1.0785(6) 1_555 1_555 yes
C(17) H(17B) 1.0716(6) 1_555 1_555 yes
C(17) H(17C) 1.0991(5) 1_555 1_555 yes
C(18) C(19) 1.5220(6) 1_555 1_555 yes
C(19) H(19A) 1.0930(6) 1_555 1_555 yes
C(19) H(19B) 1.0852(5) 1_555 1_555 yes
C(19) H(19C) 1.0748(5) 1_555 1_555 yes

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
O(3) N(1) O(2) 122.51(5) 1_555 1_555 1_555 yes
O(3) N(1) C(1) 118.58(4) 1_555 1_555 1_555 yes
O(2) N(1) C(1) 118.90(4) 1_555 1_555 1_555 yes
C(4) N(2) C(7) 126.59(4) 1_555 1_555 1_555 yes
C(4) N(2) H(2A) 114.03(3) 1_555 1_555 1_555 yes
C(7) N(2) H(2A) 119.37(3) 1_555 1_555 1_555 yes
C(7) N(3) C(8) 126.91(4) 1_555 1_555 1_555 yes
C(7) N(3) H(3A) 119.05(3) 1_555 1_555 1_555 yes
C(8) N(3) H(3A) 114.03(3) 1_555 1_555 1_555 yes
O(4) N(4) O(5) 122.86(6) 1_555 1_555 1_555 yes
O(4) N(4) C(11) 118.30(5) 1_555 1_555 1_555 yes
O(5) N(4) C(11) 118.83(5) 1_555 1_555 1_555 yes
N(1) C(1) C(2) 119.39(4) 1_555 1_555 1_555 yes
N(1) C(1) C(6) 119.23(4) 1_555 1_555 1_555 yes
C(2) C(1) C(6) 121.35(4) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 118.74(4) 1_555 1_555 1_555 yes
C(1) C(2) H(2) 119.17(4) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 122.09(4) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 121.10(4) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 121.10(4) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 117.76(4) 1_555 1_555 1_555 yes
N(2) C(4) C(3) 116.26(3) 1_555 1_555 1_555 yes
N(2) C(4) C(5) 124.78(4) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 118.96(3) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 120.08(4) 1_555 1_555 1_555 yes
C(4) C(5) H(5) 118.34(4) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 121.53(4) 1_555 1_555 1_555 yes
C(1) C(6) C(5) 119.77(4) 1_555 1_555 1_555 yes
C(1) C(6) H(6) 119.02(4) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 121.17(4) 1_555 1_555 1_555 yes
O(1) C(7) N(2) 123.93(4) 1_555 1_555 1_555 yes
O(1) C(7) N(3) 124.71(4) 1_555 1_555 1_555 yes
N(2) C(7) N(3) 111.36(3) 1_555 1_555 1_555 yes
N(3) C(8) C(9) 115.80(3) 1_555 1_555 1_555 yes
N(3) C(8) C(13) 125.06(4) 1_555 1_555 1_555 yes
C(9) C(8) C(13) 119.13(3) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 120.87(4) 1_555 1_555 1_555 yes
C(8) C(9) H(9) 119.06(4) 1_555 1_555 1_555 yes
C(10) C(9) H(9) 120.05(4) 1_555 1_555 1_555 yes
C(9) C(10) C(11) 118.84(4) 1_555 1_555 1_555 yes
C(9) C(10) H(10) 120.83(4) 1_555 1_555 1_555 yes
C(11) C(10) H(10) 120.32(4) 1_555 1_555 1_555 yes
N(4) C(11) C(10) 119.13(4) 1_555 1_555 1_555 yes
N(4) C(11) C(12) 119.34(4) 1_555 1_555 1_555 yes
C(10) C(11) C(12) 121.53(4) 1_555 1_555 1_555 yes
C(11) C(12) C(13) 119.75(4) 1_555 1_555 1_555 yes
C(11) C(12) H(12) 120.01(4) 1_555 1_555 1_555 yes
C(13) C(12) H(12) 120.23(4) 1_555 1_555 1_555 yes
C(8) C(13) C(12) 119.89(4) 1_555 1_555 1_555 yes
C(8) C(13) H(13) 119.47(4) 1_555 1_555 1_555 yes
C(12) C(13) H(13) 120.63(4) 1_555 1_555 1_555 yes
H(14A) C(14) H(14B) 109.64(5) 1_555 1_555 1_555 yes
H(14A) C(14) H(14C) 111.63(5) 1_555 1_555 1_555 yes
H(14B) C(14) H(14C) 111.00(4) 1_555 1_555 1_555 yes
H(15A) C(15) H(15B) 109.53(6) 1_555 1_555 1_555 yes
H(15A) C(15) H(15C) 109.74(6) 1_555 1_555 1_555 yes
H(15B) C(15) H(15C) 110.44(7) 1_555 1_555 1_555 yes
H(16A) C(16) H(16B) 110.89(5) 1_555 1_555 1_555 yes
H(16A) C(16) H(16C) 109.29(5) 1_555 1_555 1_555 yes
H(16B) C(16) H(16C) 111.03(6) 1_555 1_555 1_555 yes
H(17A) C(17) H(17B) 109.92(5) 1_555 1_555 1_555 yes
H(17A) C(17) H(17C) 111.03(5) 1_555 1_555 1_555 yes
H(17B) C(17) H(17C) 111.49(5) 1_555 1_555 1_555 yes
O(6) C(18) O(7) 124.72(5) 1_555 1_555 1_555 yes
O(6) C(18) C(19) 118.00(4) 1_555 1_555 1_555 yes
O(7) C(18) C(19) 117.27(4) 1_555 1_555 1_555 yes
C(18) C(19) H(19A) 109.90(4) 1_555 1_555 1_555 yes
C(18) C(19) H(19B) 110.74(4) 1_555 1_555 1_555 yes
C(18) C(19) H(19C) 111.39(4) 1_555 1_555 1_555 yes
H(19A) C(19) H(19B) 106.98(4) 1_555 1_555 1_555 yes
H(19A) C(19) H(19C) 109.28(5) 1_555 1_555 1_555 yes
H(19B) C(19) H(19C) 108.43(4) 1_555 1_555 1_555 yes
_database_code_depnum_ccdc_archive 'CCDC 953242'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_crystalstructure_6
#==============================================================================
# CHEMICAL DATA

_chemical_name_systematic        
;
 1,3-bis(4-nitrophenyl)urea with tetramethylammonium fluoride
;
_chemical_formula_moiety         '2 (C13 H10 N4 O5), C4 H12 N, F'
_chemical_formula_sum            'C30 H32 F N9 O10'
_chemical_formula_weight         697.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c c a'
_symmetry_space_group_name_Hall  '-P 2a 2ac'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,+Z
3 1/2+X,-Y,1/2-Z
4 -X,+Y,1/2-Z
5 -X,-Y,-Z
6 1/2+X,+Y,-Z
7 1/2-X,+Y,1/2+Z
8 +X,-Y,1/2+Z

_cell_length_a                   35.929(6)
_cell_length_b                   7.0153(11)
_cell_length_c                   12.624(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3181.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8688
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      31.6

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9886
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_exptl_special_details           
;
 ?
;

#==============================================================================

# EXPERIMENTAL DATA
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.68890
_diffrn_source_type              'DLS beamline I19'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_collimation    'confocal mirrors'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            159791
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       76
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         49.89
_reflns_number_total             17539
_reflns_number_gt                15592
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
#==============================================================================

# REFINEMENT DATA 
_refine_special_details          
;
The TMA cation was modelled as disorder over the 2 fold axis.
Multipole populations for the atoms in the TMA cation were taken from the 
INVARIOM database and fixed throughout the refinement. 
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         12478
_refine_ls_number_parameters     586
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.029
_refine_ls_wR_factor_ref         0.038
_refine_ls_goodness_of_fit_ref   2.067
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.035
_diffrn_measured_fraction_theta_max 0.84
_diffrn_reflns_theta_full        40.17
_diffrn_measured_fraction_theta_full 0.93
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL 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_occupancy
_atom_site_symmetry_multiplicity
F(1) 0 0.29460(10) -0.25 0.024 1 4
O(1) 0.037351(9) 0.17352(5) 0.07794(3) 0.02 1 8
O(2) -0.132648(10) 0.41312(6) 0.30811(3) 0.026 1 8
O(3) -0.163531(9) 0.47378(6) 0.16463(3) 0.027 1 8
O(4) 0.205194(15) -0.06575(8) -0.26207(6) 0.041 1 8
O(5) 0.213448(13) -0.10694(8) -0.09248(6) 0.04 1 8
N(2) -0.008390(8) 0.27791(4) -0.03860(2) 0.016 1 8
N(3) 0.047678(8) 0.18911(4) -0.10331(2) 0.017 1 8
N(1) -0.134452(7) 0.42898(3) 0.21082(2) 0.018 1 8
N(4) 0.194370(10) -0.05514(4) -0.16905(3) 0.03 1 8
N(5) 0.253705 -0.508277 0.091197 0.023 0.5 8
C(5) -0.037380(8) 0.29067(4) 0.13863(2) 0.017 1 8
C(4) -0.038228(7) 0.31406(3) 0.02785(2) 0.014 1 8
C(1) -0.101421(8) 0.39182(3) 0.14804(2) 0.016 1 8
C(3) -0.071309(8) 0.37996(4) -0.02102(2) 0.016 1 8
C(6) -0.068969(8) 0.33023(4) 0.19850(2) 0.017 1 8
C(2) -0.102917(8) 0.41742(4) 0.03817(2) 0.016 1 8
C(8) 0.084276(8) 0.13356(3) -0.11220(2) 0.016 1 8
C(7) 0.026584(7) 0.20995(3) -0.01219(2) 0.015 1 8
C(11) 0.157277(9) 0.01762(4) -0.14949(3) 0.022 1 8
C(9) 0.097850(9) 0.11310(4) -0.21696(3) 0.02 1 8
C(13) 0.108414(9) 0.09867(4) -0.02610(3) 0.019 1 8
C(12) 0.144746(9) 0.03985(5) -0.04535(3) 0.022 1 8
C(10) 0.134134(10) 0.05707(5) -0.23589(3) 0.023 1 8
C(14A) 0.222118 -0.603886 0.034153 0.048 0.5 8
C(15A) 0.23443 -0.389819 0.17303 0.054 0.5 8
C(14B) 0.278347 -0.400762 0.016508 0.048 0.5 8
C(15B) 0.27482 -0.668255 0.141623 0.041 0.5 8
H(2A) -0.011157 0.29836 -0.11732 0.037 1 8
H(3A) 0.0347 0.219619 -0.172134 0.045 1 8
H(5) -0.012102 0.237687 0.17492 0.036 1 8
H(3) -0.069825 0.404204 -0.105636 0.034 1 8
H(6) -0.067145 0.310589 0.283429 0.038 1 8
H(2) -0.128681 0.468453 0.003834 0.037 1 8
H(9) 0.079105 0.13754 -0.282756 0.041 1 8
H(13) 0.099335 0.113456 0.055289 0.038 1 8
H(12) 0.162757 0.006025 0.02082 0.045 1 8
H(10) 0.144803 0.036045 -0.315268 0.046 1 8
H(14A) 0.232867 -0.693101 -0.026207 0.072 0.5 8
H(14B) 0.204641 -0.499056 -0.000043 0.072 0.5 8
H(14C) 0.206579 -0.686904 0.088494 0.072 0.5 8
H(15A) 0.217579 -0.478565 0.221039 0.08 0.5 8
H(15B) 0.217553 -0.286531 0.135144 0.08 0.5 8
H(15C) 0.254513 -0.320496 0.220843 0.08 0.5 8
H(14D) 0.290676 -0.497038 -0.037746 0.072 0.5 8
H(14E) 0.299465 -0.33016 0.059928 0.072 0.5 8
H(14F) 0.262329 -0.299041 -0.025486 0.072 0.5 8
H(15D) 0.288201 -0.749738 0.082155 0.061 0.5 8
H(15E) 0.256171 -0.756322 0.184342 0.061 0.5 8
H(15F) 0.295027 -0.611894 0.19405 0.061 0.5 8



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
F(1) 3.642(18) 0 0 0 -0.064(8) -0.002(10) 0 0 0.003(8) 0.007(8) -0.034(6) 0 0
-0.001(5) 0.001(6) 0 0 0.002(8) 0 0 -0.005(7) -0.024(8) 0 0 0.008(6) 0.002(6)
0.975(3) 1 1 1 1 1 2 5.1078857142857 2 5.1078857142857 2 5.1078857142857 3
5.1078857142857 4 5.1078857142857
O(1) 6.13(4) 0 -0.033(11) -0.011(9) 0.005(9) -0.054(11) 0.013(10) 0.012(10)
-0.049(11) 0.003(10) -0.015(9) 0.014(8) -0.019(8) 0.015(8) -0.005(8) 0.022(8)
-0.007(8) 0.006(11) 0.001(10) -0.008(10) -0.025(10) -0.019(10) 0.015(10)
-0.025(10) -0.004(9) -0.007(10) 0.983(3) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3
4.466 4 4.466
O(2) 6.10(2) 0 -0.066(9) -0.015(7) -0.012(8) -0.044(10) 0.010(8) 0.008(8)
-0.127(9) 0.007(8) -0.031(7) -0.005(7) 0.008(7) -0.009(7) 0.016(7) 0.027(6)
0.015(6) -0.013(10) -0.008(8) 0.001(9) -0.001(9) 0.000(9) 0.001(8) 0.004(8)
0.002(8) 0.008(8) 0.9889(19) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(3) 6.1006 0 -0.0663 -0.0154 -0.012 -0.0439 0.01 0.0083 -0.1274 0.007 -0.0305
-0.0051 0.0084 -0.0085 0.016 0.0265 0.0154 -0.0133 -0.008 0.0007 -0.0009
-0.0003 0.001 0.004 0.0023 0.0078 0.9889(19) 1 1 1 1 1 2 4.466 2 4.466 2 4.466
3 4.466 4 4.466
O(4) 6.11(2) 0 -0.011(12) 0.010(10) 0.025(9) 0.006(13) 0.000(11) -0.026(11)
-0.120(12) -0.022(12) -0.080(9) 0.069(9) -0.018(9) 0.044(9) 0.058(9) -0.016(9)
0.012(9) -0.011(13) -0.015(11) 0.034(11) 0.014(12) -0.002(12) 0.022(12)
-0.047(11) 0.023(12) 0.007(11) 0.9889(19) 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3
4.466 4 4.466
O(5) 6.1128 0 -0.0105 0.0103 0.0253 0.0057 0.0002 -0.0257 -0.1198 -0.0217
-0.0797 0.0685 -0.0178 0.0438 0.0584 -0.0163 0.0121 -0.0112 -0.0152 0.0337
0.0144 -0.0016 0.0219 -0.047 0.0232 0.0065 0.9889(19) 1 1 1 1 1 2 4.466 2 4.466
2 4.466 3 4.466 4 4.466
N(2) 5.11(4) 0 -0.048(10) -0.041(11) -0.023(8) -0.020(10) -0.013(9) 0.001(9)
-0.022(9) 0.030(10) 0.017(9) 0.006(9) 0.045(9) 0.003(9) -0.017(9) 0.175(10)
0.051(9) 0.029(12) -0.004(11) -0.005(11) 0.022(11) -0.016(11) -0.022(11)
0.001(11) 0.004(11) -0.008(11) 0.984(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936
3 3.83936 4 3.83936
N(3) 5.14(4) 0 -0.066(10) -0.041(11) 0.014(9) -0.006(10) 0.016(9) 0.006(9)
0.000(10) 0.025(10) 0.014(9) 0.011(9) 0.032(9) 0.010(9) 0.006(9) 0.177(10)
0.033(9) 0.032(12) -0.011(11) 0.000(11) 0.029(12) -0.014(11) 0.022(11)
0.004(12) -0.034(12) -0.014(12) 0.984(3) 1 1 1 1 1 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
N(1) 5.06(4) 0 0 0 0.013(9) 0.066(9) 0 0 -0.150(10) 0 0.228(10) 0 0 0.162(10) 0
0 0 0.032(12) 0 0 -0.015(11) 0 0 0 0.020(10) 0 0.982(3) 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(4) 5.0593 0 0 0 0.0134 0.0664 0 0 -0.15 0 0.2281 0 0 0.1622 0 0 0 0.0315 0 0
-0.0145 0 0 0 0.0197 0 0.982(3) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3
3.83936 4 3.83936
N(5) 2.585 0 0 0 0 -0.0001 0 0 0 0 0.1099 0 0 0 0 0 -0.0897 0.0208 0 0 0 0
-0.0003 0.0311 0 0 0.991952 0.872472 0.872472 0.872472 0.872472 0.872472 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
C(5) 4.11(4) 0 0.001(13) -0.017(13) -0.017(11) -0.145(12) 0.009(11) 0.015(11)
0.008(12) 0.035(13) -0.001(13) 0.027(12) 0.054(12) 0.004(12) -0.015(12)
0.217(14) -0.005(13) 0 0 0 0 0 0 0 0 0 0.991(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(4) 4.05(3) 0 0.016(13) 0.077(13) -0.011(10) -0.186(11) 0.006(11) 0.017(10)
0.015(12) -0.046(12) -0.006(12) -0.001(11) 0.019(12) -0.008(12) 0.013(12)
0.259(14) 0.024(13) 0 0 0 0 0 0 0 0 0 0.991(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(1) 3.94(3) 0 0.049(13) 0.099(13) 0.008(11) -0.082(12) 0.011(11) 0.007(10)
0.065(12) -0.090(12) 0.021(12) -0.003(12) -0.006(11) 0.005(12) 0.010(12)
0.192(14) 0.022(13) 0 0 0 0 0 0 0 0 0 0.991(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(3) 4.02(3) 0 0.016(13) -0.012(13) 0.021(10) -0.146(11) -0.004(11) -0.003(11)
0.003(12) 0.004(13) -0.012(12) 0.035(12) 0.033(12) -0.026(12) 0.021(12)
0.235(13) -0.037(13) 0 0 0 0 0 0 0 0 0 0.991(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(6) 4.14(3) 0 -0.024(13) -0.032(14) -0.021(11) -0.200(12) -0.013(11) 0.003(11)
-0.031(12) 0.015(13) -0.026(13) 0.024(12) 0.041(12) -0.005(13) 0.021(12)
0.272(14) -0.006(13) 0 0 0 0 0 0 0 0 0 0.991(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(2) 4.11(3) 0 0.029(13) -0.001(14) 0.003(11) -0.194(12) -0.005(11) 0.003(11)
0.011(12) -0.003(13) 0.036(13) 0.006(12) 0.015(12) 0.003(12) -0.007(12)
0.258(14) 0.001(13) 0 0 0 0 0 0 0 0 0 0.991(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(8) 3.97(3) 0 -0.007(13) 0.055(14) 0.004(11) -0.163(11) 0.001(11) 0.027(11)
-0.008(13) -0.029(13) 0.006(12) 0.014(12) 0.022(12) 0.015(13) -0.007(13)
0.288(14) 0.002(14) 0 0 0 0 0 0 0 0 0 0.990(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(7) 4.00(7) 0 0.006(10) -0.027(12) 0.114(14) 0.174(14) 0.005(11) 0.014(12)
-0.147(11) 0.003(11) 0.223(17) -0.003(13) -0.013(15) 0.192(14) 0.037(13)
0.002(11) -0.008(12) 0 0 0 0 0 0 0 0 0 0.980(6) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(11) 4.04(3) 0 0.146(15) 0.031(14) 0.010(12) -0.064(12) 0.024(13) 0.017(12)
0.079(14) -0.046(14) 0.023(14) -0.020(13) -0.001(13) 0.000(14) 0.075(14)
0.205(16) -0.030(15) 0 0 0 0 0 0 0 0 0 0.990(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(9) 4.10(4) 0 0.030(15) 0.054(15) -0.040(12) -0.139(13) 0.027(12) -0.007(12)
-0.015(13) -0.021(13) 0.004(13) 0.036(13) 0.016(13) -0.008(13) -0.041(13)
0.189(15) 0.043(14) 0 0 0 0 0 0 0 0 0 0.990(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(13) 3.98(3) 0 -0.037(14) -0.009(15) -0.015(11) -0.161(12) 0.010(11)
-0.006(11) -0.024(13) -0.014(14) 0.020(13) 0.023(13) 0.040(12) -0.002(13)
0.000(13) 0.221(14) -0.013(14) 0 0 0 0 0 0 0 0 0 0.990(2) 1 1 1 1 1 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
C(12) 4.16(4) 0 0.024(15) -0.015(16) 0.011(11) -0.152(13) -0.022(12) 0.007(12)
0.033(14) 0.001(14) 0.055(14) 0.045(13) 0.035(14) 0.041(14) 0.015(14) 0.240(16)
0.019(15) 0 0 0 0 0 0 0 0 0 0.990(2) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(10) 4.07(4) 0 0.043(16) 0.051(15) 0.025(12) -0.214(14) 0.020(13) 0.017(11)
0.011(14) -0.041(15) 0.027(14) -0.035(14) 0.034(13) -0.027(14) 0.000(14)
0.334(16) -0.014(15) 0 0 0 0 0 0 0 0 0 0.990(2) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(14A) 1.8982 0 0 0 -0.0067 -0.0176 0 0 0 0 0.121 0 0 0 0 0 -0.0816 0 0 0 0 0 0
0 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(15A) 1.8982 0 0 0 -0.0067 -0.0176 0 0 0 0 0.121 0 0 0 0 0 -0.0816 0 0 0 0 0 0
0 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(14B) 1.8982 0 0 0 -0.0067 -0.0176 0 0 0 0 0.121 0 0 0 0 0 -0.0816 0 0 0 0 0 0
0 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(15B) 1.8982 0 0 0 -0.0067 -0.0176 0 0 0 0 0.121 0 0 0 0 0 -0.0816 0 0 0 0 0 0
0 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(2A) 0.73(2) 0 0 0 0.068(15) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3A) 0.76(2) 0 0 0 0.089(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5) 0.84(2) 0 0 0 0.134(15) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.838(19) 0 0 0 0.125(14) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6) 0.84(2) 0 0 0 0.089(15) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2) 0.817(19) 0 0 0 0.173(14) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9) 0.89(2) 0 0 0 0.141(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(13) 0.82(2) 0 0 0 0.128(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(12) 0.86(2) 0 0 0 0.146(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10) 0.85(2) 0 0 0 0.166(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14A) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14B) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14C) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15A) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15B) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15C) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14D) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14E) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14F) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15D) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15E) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15F) 0.5269 0 0 0 0.0759 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.112822
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
F(1) DUM1 Z F(1) C(15A) Y
O(1) C(7) X O(1) C(13) Y
O(2) N(1) -X O(2) O(3) Y
O(3) N(1) X O(3) O(2) Y
O(4) N(4) X O(4) O(5) Y
O(5) N(4) -X O(5) O(4) Y
N(2) C(4) X N(2) C(7) Y
N(3) C(8) X N(3) C(7) Y
N(1) C(1) Z N(1) O(2) Y
N(4) C(11) Z N(4) O(4) Y
N(5) C(15A) Z N(5) C(15B) Y
C(5) C(6) X C(5) C(4) Y
C(4) C(3) X C(4) C(5) Y
C(1) C(6) X C(1) C(2) Y
C(3) C(4) X C(3) C(2) Y
C(6) C(1) X C(6) C(5) Y
C(2) C(3) X C(2) C(1) Y
C(8) C(9) X C(8) C(13) Y
C(7) O(1) Z C(7) N(3) Y
C(11) C(12) X C(11) C(10) Y
C(9) C(10) X C(9) C(8) Y
C(13) C(8) X C(13) C(12) Y
C(12) C(13) X C(12) C(11) Y
C(10) C(11) X C(10) C(9) Y
C(14A) N(5) Z C(14A) H(14C) Y
C(15A) N(5) Z C(15A) H(15B) Y
C(14B) N(5) Z C(14B) H(14E) Y
C(15B) N(5) Z C(15B) H(15F) Y
H(2A) N(2) Z H(2A) C(7) Y
H(3A) N(3) Z H(3A) C(7) Y
H(5) C(5) Z H(5) C(6) Y
H(3) C(3) Z H(3) C(2) Y
H(6) C(6) Z H(6) C(5) Y
H(2) C(2) Z H(2) C(3) Y
H(9) C(9) Z H(9) C(10) Y
H(13) C(13) Z H(13) C(12) Y
H(12) C(12) Z H(12) C(13) Y
H(10) C(10) Z H(10) C(9) Y
H(14A) C(14A) Z H(14A) N(5) Y
H(14B) C(14A) Z H(14B) N(5) Y
H(14C) C(14A) Z H(14C) N(5) Y
H(15A) C(15A) Z H(15A) N(5) Y
H(15B) C(15A) Z H(15B) N(5) Y
H(15C) C(15A) Z H(15C) N(5) Y
H(14D) C(14B) Z H(14D) N(5) Y
H(14E) C(14B) Z H(14E) N(5) Y
H(14F) C(14B) Z H(14F) N(5) Y
H(15D) C(15B) Z H(15D) N(5) Y
H(15E) C(15B) Z H(15E) N(5) Y
H(15F) C(15B) Z H(15F) N(5) Y


#----------------------------------------------------------------------------#
#                   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
O(1) C(7) 1.2286(4) 1_555 1_555 yes
O(2) N(1) 1.2349(4) 1_555 1_555 yes
O(3) N(1) 1.2371(4) 1_555 1_555 yes
O(4) N(4) 1.2392(7) 1_555 1_555 yes
O(5) N(4) 1.2394(8) 1_555 1_555 yes
N(2) C(4) 1.3846(4) 1_555 1_555 yes
N(2) C(7) 1.3847(4) 1_555 1_555 yes
N(2) H(2A) 1.0090(3) 1_555 1_555 yes
N(3) C(8) 1.3760(4) 1_555 1_555 yes
N(3) C(7) 1.3853(4) 1_555 1_555 yes
N(3) H(3A) 1.0090(3) 1_555 1_555 yes
N(1) C(1) 1.4507(4) 1_555 1_555 yes
N(4) C(11) 1.4483(5) 1_555 1_555 yes
N(5) N(5) 0.29045997694748 1_555 2_545 yes
N(5) C(14A) 1.3756034345616 1_555 2_545 yes
N(5) C(15A) 1.3266523919396 1_555 2_545 yes
C(5) C(4) 1.4084(4) 1_555 1_555 yes
C(5) C(6) 1.3915(4) 1_555 1_555 yes
C(5) H(5) 1.0830(3) 1_555 1_555 yes
C(4) C(3) 1.4167(4) 1_555 1_555 yes
C(1) C(6) 1.3971(4) 1_555 1_555 yes
C(1) C(2) 1.3997(4) 1_555 1_555 yes
C(3) C(2) 1.3845(4) 1_555 1_555 yes
C(3) H(3) 1.0830(3) 1_555 1_555 yes
C(6) H(6) 1.0830(3) 1_555 1_555 yes
C(2) H(2) 1.0830(3) 1_555 1_555 yes
C(8) C(9) 1.4169(4) 1_555 1_555 yes
C(8) C(13) 1.4118(4) 1_555 1_555 yes
C(11) C(12) 1.3983(5) 1_555 1_555 yes
C(11) C(10) 1.3991(6) 1_555 1_555 yes
C(9) C(10) 1.3824(5) 1_555 1_555 yes
C(9) H(9) 1.0830(4) 1_555 1_555 yes
C(13) C(12) 1.3904(4) 1_555 1_555 yes
C(13) H(13) 1.0830(3) 1_555 1_555 yes
C(12) H(12) 1.0830(4) 1_555 1_555 yes
C(10) H(10) 1.0830(4) 1_555 1_555 yes
C(14A) C(14B) 0.22574350262749 1_555 2_545 yes
C(14A) H(14A) 1.0590018825753 1_555 1_555 yes
C(14A) H(14B) 1.0590034458713 1_555 1_555 yes
C(14A) H(14C) 1.0590007975684 1_555 1_555 yes
C(14A) H(14E) 0.95983607590424 1_555 2_545 yes
C(14A) H(14F) 1.1588141602661 1_555 2_545 yes
C(15A) C(15B) 0.65850610226976 1_555 2_545 yes
C(15A) H(15A) 1.0589989249058 1_555 1_555 yes
C(15A) H(15B) 1.0589969295375 1_555 1_555 yes
C(15A) H(15C) 1.0590003132566 1_555 1_555 yes
C(15A) H(15E) 1.0888126787076 1_555 2_545 yes
C(15A) H(15F) 1.0911855558463 1_555 2_545 yes
C(14B) H(14A) 0.94164792073222 1_555 2_545 yes
C(14B) H(14B) 0.95456205983797 1_555 2_545 yes
C(14B) H(14D) 1.059001782383 1_555 1_555 yes
C(14B) H(14E) 1.0589926327064 1_555 1_555 yes
C(14B) H(14F) 1.0590010158669 1_555 1_555 yes
C(15B) H(15B) 0.42707366922299 1_555 2_545 yes
C(15B) H(15D) 1.0589999801012 1_555 1_555 yes
C(15B) H(15E) 1.0589990276133 1_555 1_555 yes
C(15B) H(15F) 1.0589913206456 1_555 1_555 yes
H(14A) H(14F) 0.18142084592598 1_555 2_545 yes
H(14B) H(14D) 0.50557030339168 1_555 2_545 yes
H(14C) H(14E) 0.43764282830573 1_555 2_545 yes
H(15B) H(15D) 0.74494956713078 1_555 2_545 yes

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
C(4) N(2) C(7) 128.30(3) 1_555 1_555 1_555 yes
C(4) N(2) H(2A) 119.63(3) 1_555 1_555 1_555 yes
C(7) N(2) H(2A) 112.06(2) 1_555 1_555 1_555 yes
C(8) N(3) C(7) 128.34(3) 1_555 1_555 1_555 yes
C(8) N(3) H(3A) 115.56(3) 1_555 1_555 1_555 yes
C(7) N(3) H(3A) 116.09(3) 1_555 1_555 1_555 yes
O(2) N(1) O(3) 122.41(4) 1_555 1_555 1_555 yes
O(2) N(1) C(1) 118.96(3) 1_555 1_555 1_555 yes
O(3) N(1) C(1) 118.62(3) 1_555 1_555 1_555 yes
O(4) N(4) O(5) 123.22(6) 1_555 1_555 1_555 yes
O(4) N(4) C(11) 118.13(5) 1_555 1_555 1_555 yes
O(5) N(4) C(11) 118.64(4) 1_555 1_555 1_555 yes
N(5) N(5) C(14A) 110.4936826126 2_545 1_555 2_545 yes
N(5) N(5) C(15A) 120.6625466812 2_545 1_555 2_545 yes
C(14A) N(5) C(15A) 120.86174015393 2_545 1_555 2_545 yes
C(4) C(5) C(6) 119.89(3) 1_555 1_555 1_555 yes
C(4) C(5) H(5) 118.57(2) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 121.51(3) 1_555 1_555 1_555 yes
N(2) C(4) C(5) 124.29(2) 1_555 1_555 1_555 yes
N(2) C(4) C(3) 116.46(2) 1_555 1_555 1_555 yes
C(5) C(4) C(3) 119.25(2) 1_555 1_555 1_555 yes
N(1) C(1) C(6) 119.29(2) 1_555 1_555 1_555 yes
N(1) C(1) C(2) 119.14(2) 1_555 1_555 1_555 yes
C(6) C(1) C(2) 121.57(2) 1_555 1_555 1_555 yes
C(4) C(3) C(2) 121.01(3) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 116.07(2) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 122.88(3) 1_555 1_555 1_555 yes
C(5) C(6) C(1) 119.66(3) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 117.58(3) 1_555 1_555 1_555 yes
C(1) C(6) H(6) 122.77(3) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 118.61(3) 1_555 1_555 1_555 yes
C(1) C(2) H(2) 118.15(3) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 123.22(3) 1_555 1_555 1_555 yes
N(3) C(8) C(9) 115.70(3) 1_555 1_555 1_555 yes
N(3) C(8) C(13) 124.98(3) 1_555 1_555 1_555 yes
C(9) C(8) C(13) 119.31(3) 1_555 1_555 1_555 yes
O(1) C(7) N(2) 125.47(3) 1_555 1_555 1_555 yes
O(1) C(7) N(3) 125.08(3) 1_555 1_555 1_555 yes
N(2) C(7) N(3) 109.44(2) 1_555 1_555 1_555 yes
N(4) C(11) C(12) 119.73(4) 1_555 1_555 1_555 yes
N(4) C(11) C(10) 118.92(4) 1_555 1_555 1_555 yes
C(12) C(11) C(10) 121.30(3) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 120.98(3) 1_555 1_555 1_555 yes
C(8) C(9) H(9) 119.06(3) 1_555 1_555 1_555 yes
C(10) C(9) H(9) 119.93(3) 1_555 1_555 1_555 yes
C(8) C(13) C(12) 119.58(3) 1_555 1_555 1_555 yes
C(8) C(13) H(13) 121.92(3) 1_555 1_555 1_555 yes
C(12) C(13) H(13) 118.49(3) 1_555 1_555 1_555 yes
C(11) C(12) C(13) 119.98(3) 1_555 1_555 1_555 yes
C(11) C(12) H(12) 120.55(3) 1_555 1_555 1_555 yes
C(13) C(12) H(12) 119.42(3) 1_555 1_555 1_555 yes
C(11) C(10) C(9) 118.81(3) 1_555 1_555 1_555 yes
C(11) C(10) H(10) 118.95(3) 1_555 1_555 1_555 yes
C(9) C(10) H(10) 122.17(4) 1_555 1_555 1_555 yes
N(5) C(14A) C(14B) 118.72897405836 2_545 1_555 2_545 yes
N(5) C(14A) H(14A) 118.975847769 2_545 1_555 1_555 yes
N(5) C(14A) H(14B) 100.98781227308 2_545 1_555 1_555 yes
N(5) C(14A) H(14C) 107.96125780384 2_545 1_555 1_555 yes
N(5) C(14A) H(14E) 127.47677448365 2_545 1_555 2_545 yes
N(5) C(14A) H(14F) 111.82404224086 2_545 1_555 2_545 yes
C(14B) C(14A) H(14A) 53.299283583492 2_545 1_555 1_555 yes
C(14B) C(14A) H(14B) 56.877976533802 2_545 1_555 1_555 yes
C(14B) C(14A) H(14C) 132.81337556933 2_545 1_555 1_555 yes
C(14B) C(14A) H(14E) 110.14163104381 2_545 1_555 2_545 yes
C(14B) C(14A) H(14F) 58.633271095757 2_545 1_555 2_545 yes
H(14A) C(14A) H(14B) 109.47182917085 1_555 1_555 1_555 yes
H(14A) C(14A) H(14C) 109.47157808326 1_555 1_555 1_555 yes
H(14A) C(14A) H(14E) 104.6942214107 1_555 1_555 2_545 yes
H(14A) C(14A) H(14F) 7.8416507831877 1_555 1_555 2_545 yes
H(14B) C(14A) H(14C) 109.47336582021 1_555 1_555 1_555 yes
H(14B) C(14A) H(14E) 89.650461069444 1_555 1_555 2_545 yes
H(14B) C(14A) H(14F) 115.41595095617 1_555 1_555 2_545 yes
H(14C) C(14A) H(14E) 24.408414403043 1_555 1_555 2_545 yes
H(14C) C(14A) H(14F) 110.60373224201 1_555 1_555 2_545 yes
H(14E) C(14A) H(14F) 109.05969901164 2_545 1_555 2_545 yes
N(5) C(15A) C(15B) 91.530779353666 2_545 1_555 2_545 yes
N(5) C(15A) H(15A) 108.21371476712 2_545 1_555 1_555 yes
N(5) C(15A) H(15B) 101.59657792066 2_545 1_555 1_555 yes
N(5) C(15A) H(15C) 118.18664266244 2_545 1_555 1_555 yes
N(5) C(15A) H(15E) 120.65459722076 2_545 1_555 2_545 yes
N(5) C(15A) H(15F) 120.46203198696 2_545 1_555 2_545 yes
C(15B) C(15A) H(15A) 114.81953324044 2_545 1_555 1_555 yes
C(15B) C(15A) H(15B) 10.189892791042 2_545 1_555 1_555 yes
C(15B) C(15A) H(15C) 113.76165856845 2_545 1_555 1_555 yes
C(15B) C(15A) H(15E) 69.692861328632 2_545 1_555 2_545 yes
C(15B) C(15A) H(15F) 69.518431769967 2_545 1_555 2_545 yes
H(15A) C(15A) H(15B) 109.47317113418 1_555 1_555 1_555 yes
H(15A) C(15A) H(15C) 109.47084955639 1_555 1_555 1_555 yes
H(15A) C(15A) H(15E) 130.9815892414 1_555 1_555 2_545 yes
H(15A) C(15A) H(15F) 46.590342375366 1_555 1_555 2_545 yes
H(15B) C(15A) H(15C) 109.47147001247 1_555 1_555 1_555 yes
H(15B) C(15A) H(15E) 65.955553964001 1_555 1_555 2_545 yes
H(15B) C(15A) H(15F) 63.058817332514 1_555 1_555 2_545 yes
H(15C) C(15A) H(15E) 44.070518392099 1_555 1_555 2_545 yes
H(15C) C(15A) H(15F) 121.14477078285 1_555 1_555 2_545 yes
H(15E) C(15A) H(15F) 104.98443891342 2_545 1_555 2_545 yes
C(14A) C(14B) H(14A) 115.6189585342 2_545 1_555 2_545 yes
C(14A) C(14B) H(14B) 111.69838592379 2_545 1_555 2_545 yes
C(14A) C(14B) H(14D) 139.57433490631 2_545 1_555 1_555 yes
C(14A) C(14B) H(14E) 58.313794442844 2_545 1_555 1_555 yes
C(14A) C(14B) H(14F) 110.87971205528 2_545 1_555 1_555 yes
H(14A) C(14B) H(14B) 131.56629637841 2_545 1_555 2_545 yes
H(14A) C(14B) H(14D) 104.75005958172 2_545 1_555 1_555 yes
H(14A) C(14B) H(14E) 106.01633359154 2_545 1_555 1_555 yes
H(14A) C(14B) H(14F) 7.9445493508091 2_545 1_555 1_555 yes
H(14B) C(14B) H(14D) 28.481587884696 2_545 1_555 1_555 yes
H(14B) C(14B) H(14E) 89.935235281827 2_545 1_555 1_555 yes
H(14B) C(14B) H(14F) 137.26775576533 2_545 1_555 1_555 yes
H(14D) C(14B) H(14E) 109.47202826231 1_555 1_555 1_555 yes
H(14D) C(14B) H(14F) 109.47057525253 1_555 1_555 1_555 yes
H(14E) C(14B) H(14F) 109.47029788892 1_555 1_555 1_555 yes
C(15A) C(15B) H(15B) 153.98036315084 2_545 1_555 2_545 yes
C(15A) C(15B) H(15D) 171.8489079489 2_545 1_555 1_555 yes
C(15A) C(15B) H(15E) 74.633208275951 2_545 1_555 1_555 yes
C(15A) C(15B) H(15F) 74.854005047783 2_545 1_555 1_555 yes
H(15B) C(15B) H(15D) 34.110422735093 2_545 1_555 1_555 yes
H(15B) C(15B) H(15E) 94.026183409808 2_545 1_555 1_555 yes
H(15B) C(15B) H(15F) 87.540882894665 2_545 1_555 1_555 yes
H(15D) C(15B) H(15E) 109.47118751045 1_555 1_555 1_555 yes
H(15D) C(15B) H(15F) 109.47146277816 1_555 1_555 1_555 yes
H(15E) C(15B) H(15F) 109.47095363071 1_555 1_555 1_555 yes
C(14A) H(14A) C(14B) 11.081775907957 1_555 1_555 2_545 yes
C(14A) H(14A) H(14F) 119.36953443067 1_555 1_555 2_545 yes
C(14B) H(14A) H(14F) 126.21606918471 2_545 1_555 2_545 yes
C(14A) H(14B) C(14B) 11.423633421496 1_555 1_555 2_545 yes
C(14A) H(14B) H(14D) 98.55699418855 1_555 1_555 2_545 yes
C(14B) H(14B) H(14D) 87.309632254437 2_545 1_555 2_545 yes
C(14A) H(14C) H(14E) 65.00055636325 1_555 1_555 2_545 yes
C(15A) H(15B) C(15B) 15.829745538641 1_555 1_555 2_545 yes
C(15A) H(15B) H(15D) 142.95339167748 1_555 1_555 2_545 yes
C(15B) H(15B) H(15D) 127.1361483223 2_545 1_555 2_545 yes
C(14B) H(14D) H(14B) 64.208794394189 1_555 1_555 2_545 yes
C(14A) H(14E) C(14B) 11.544666795507 2_545 1_555 1_555 yes
C(14A) H(14E) H(14C) 90.590957030871 2_545 1_555 2_545 yes
C(14B) H(14E) H(14C) 101.47380892715 1_555 1_555 2_545 yes
C(14A) H(14F) C(14B) 10.487024145837 2_545 1_555 1_555 yes
C(14A) H(14F) H(14A) 52.788863028387 2_545 1_555 2_545 yes
C(14B) H(14F) H(14A) 45.839429896274 1_555 1_555 2_545 yes
C(15B) H(15D) H(15B) 18.753436401293 1_555 1_555 2_545 yes
C(15A) H(15E) C(15B) 35.673870402738 2_545 1_555 1_555 yes
C(15A) H(15F) C(15B) 35.62762251896 2_545 1_555 1_555 yes

_database_code_depnum_ccdc_archive 'CCDC 953243'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_crystalstructure_7
#==============================================================================

# CHEMICAL DATA
_chemical_name_systematic        
;
 1,3-bis(3-nitrophenyl)urea with tetramethylammonium chloride
;
_chemical_formula_moiety         'C13 H10 N4 O5, C4 H12 N, Cl'
_chemical_formula_sum            'C17 H22 Cl N5 O5'
_chemical_formula_weight         411.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0007 0.0007 '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 0.0777 0.0747 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0018 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0040 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA 

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

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

_cell_length_a                   6.8211(5)
_cell_length_b                   14.4139(11)
_cell_length_c                   19.7918(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1945.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11299
_cell_measurement_theta_min      1.2
_cell_measurement_theta_max      20.1

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.48590
_diffrn_source_type              'DLS beamline I19'
_diffrn_source                   synchrotron
_diffrn_radiation_collimation    'confocal mirrors'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            363541
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_theta_min         1.19
_diffrn_reflns_theta_max         45.18
_reflns_number_total             25557
_reflns_number_gt                19633
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;


#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_hydrogen_treatment    noref
#_refine_ls_abs_structure_details
# 'Flack H D (1983), Acta Cryst. A39, 876-881'
#_refine_ls_abs_structure_Flack    0.10(3)
# values above from standard resolution structure refinement
_refine_ls_extinction_method     none
_refine_ls_number_reflns         37163
_refine_ls_number_parameters     760
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.071
_refine_ls_R_factor_gt           0.038
_refine_ls_wR_factor_ref         0.038
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.061
_diffrn_measured_fraction_theta_max 0.90
_diffrn_reflns_theta_full        44.2
_diffrn_measured_fraction_theta_full 0.98
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#==============================================================================

# 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_occupancy
_atom_site_symmetry_multiplicity
CL(1) 0.598774(11) 1.615353(6) 1.035232 0.017 1 4
O(1) 0.88630(6) 1.51856(2) 0.817270(18) 0.017 1 4
O(2) 0.98486(10) 1.71710(3) 0.65173(2) 0.027 1 4
O(3) 0.97105(11) 1.86657(4) 0.64748(3) 0.032 1 4
O(4) 0.86046(9) 1.10074(3) 0.81589(3) 0.028 1 4
O(5) 0.93155(8) 1.22652(3) 0.76269(2) 0.024 1 4
N(1) 0.95516(5) 1.79302(2) 0.678149(19) 0.019 1 4
N(2) 0.80990(4) 1.63514(2) 0.892289(15) 0.013 1 4
N(3) 0.77630(5) 1.48496(2) 0.924652(16) 0.015 1 4
N(4) 0.87640(4) 1.18511(2) 0.813441(18) 0.016 1 4
N(5) 0.89159(4) 1.42427(2) 0.635598(17) 0.015 1 4
C(1) 0.87791(5) 1.88181(2) 0.78062(2) 0.016 1 4
C(2) 0.83292(5) 1.88248(2) 0.84930(2) 0.017 1 4
C(3) 0.81270(5) 1.79997(2) 0.884798(17) 0.015 1 4
C(4) 0.83534(4) 1.713839(19) 0.852390(15) 0.012 1 4
C(5) 0.88169(4) 1.71155(2) 0.783622(16) 0.013 1 4
C(6) 0.90169(4) 1.79583(2) 0.750046(17) 0.014 1 4
C(7) 0.82833(4) 1.544020(19) 0.872873(15) 0.012 1 4
C(8) 0.78222(4) 1.38842(2) 0.924479(15) 0.013 1 4
C(9) 0.73542(5) 1.34301(2) 0.985257(17) 0.015 1 4
C(10) 0.73570(5) 1.24678(3) 0.989342(19) 0.017 1 4
C(11) 0.78137(5) 1.19285(2) 0.933042(19) 0.016 1 4
C(12) 0.82794(4) 1.23946(2) 0.873811(17) 0.013 1 4
C(13) 0.83089(4) 1.33546(2) 0.867783(16) 0.013 1 4
C(14) 0.87990(9) 1.49831(4) 0.58328(3) 0.027 1 4
C(15) 0.71384(5) 1.42833(4) 0.67963(2) 0.022 1 4
C(16) 0.89900(6) 1.33161(3) 0.60141(3) 0.021 1 4
C(17) 1.07186(6) 1.43674(5) 0.67760(3) 0.027 1 4
H(1) 0.893945 1.94556 0.751869 0.036 1 4
H(2) 0.818166 1.947586 0.874144 0.039 1 4
H(3) 0.784704 1.801857 0.93834 0.03 1 4
H(5) 0.901594 1.64579 0.757214 0.027 1 4
H(9) 0.696353 1.383326 1.028373 0.034 1 4
H(10) 0.699484 1.21407 1.036725 0.035 1 4
H(11) 0.781928 1.11807 0.933891 0.034 1 4
H(13) 0.872559 1.368167 0.820389 0.03 1 4
H(14A) 0.880071 1.565202 0.607663 0.057 1 4
H(14B) 0.744337 1.48799 0.554014 0.042 1 4
H(14C) 1.008101 1.491047 0.549644 0.051 1 4
H(15A) 0.724555 1.372038 0.71592 0.046 1 4
H(15B) 0.585951 1.422001 0.647021 0.036 1 4
H(15C) 0.712147 1.494082 0.705387 0.049 1 4
H(16A) 1.025387 1.329538 0.569051 0.042 1 4
H(16B) 0.765417 1.323241 0.570117 0.042 1 4
H(16C) 0.908267 1.279282 0.639579 0.044 1 4
H(17A) 1.20156 1.433951 0.643192 0.042 1 4
H(17B) 1.079332 1.383301 0.712997 0.054 1 4
H(17C) 1.065515 1.504572 0.701447 0.055 1 4
H(2A) 0.747195 1.645659 0.938688 0.025 1 4
H(3A) 0.713235 1.515762 0.96511 0.026 1 4



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
CL(1) 7.54(6) 0 0.10(2) 0.04(3) 0.13(3) -0.053(19) -0.061(16) -0.031(16)
0.030(18) -0.031(16) -0.13(2) 0.06(3) 0.08(2) -0.037(14) 0.07(3) -0.01(3)
0.009(17) -0.008(15) -0.008(15) 0.011(14) -0.021(14) -0.012(14) 0.001(14)
0.035(15) 0.027(13) -0.028(14) 0.976996 1 1 1 1 1 4 4.2587714285714 4
4.2587714285714 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714
O(1) 6.16(3) 0 -0.058(15) 0.010(13) -0.021(14) -0.021(14) -0.015(13) -0.016(13)
-0.065(11) -0.024(11) -0.011(14) 0.054(12) 0.041(12) -0.008(12) -0.018(11)
0.047(11) 0.005(11) 0.016(16) -0.021(15) -0.010(15) 0.014(14) -0.015(14)
-0.014(13) 0.019(13) 0.010(13) -0.013(12) 0.995241 1 1 1 1 1 2 4.466 2 4.466 2
4.466 3 4.466 4 4.466
O(2) 6.15(3) 0 -0.054(12) -0.042(14) 0.110(15) -0.018(15) 0.019(13) -0.008(14)
-0.112(12) 0.040(11) 0.064(14) 0.108(12) -0.096(14) -0.024(11) -0.006(11)
0.016(12) 0.025(9) 0.015(17) 0.020(14) -0.002(15) 0.018(15) -0.003(15)
-0.012(13) 0.003(13) 0.022(12) 0.010(12) 0.992884 1 1 1 1 1 2 4.466 2 4.466 2
4.466 3 4.466 4 4.466
O(3) 6.1452 0 -0.0538 -0.042 0.1104 -0.0178 0.0185 -0.0078 -0.1119 0.0399
0.0641 0.1076 -0.0958 -0.0238 -0.0059 0.0162 0.0247 0.0154 0.0195 -0.0018
0.0177 -0.0027 -0.0116 0.0025 0.0223 0.0102 0.992884 1 1 1 1 1 2 4.466 2 4.466
2 4.466 3 4.466 4 4.466
O(4) 6.18(2) 0 -0.059(11) -0.015(13) 0.041(13) -0.043(13) 0.005(12) 0.013(12)
-0.094(11) 0.024(11) 0.016(13) 0.011(11) -0.052(11) 0.016(10) 0.003(10)
0.053(9) 0.031(9) -0.014(15) 0.004(13) -0.012(13) -0.011(13) -0.009(13)
0.020(12) -0.008(12) 0.049(11) -0.002(11) 0.992884 1 1 1 1 1 2 4.466 2 4.466 2
4.466 3 4.466 4 4.466
O(5) 6.1846 0 -0.0588 -0.0153 0.0406 -0.0431 0.005 0.0128 -0.0943 0.0244 0.0159
0.0109 -0.0523 0.0161 0.003 0.0526 0.0305 -0.0136 0.0039 -0.0124 -0.0109
-0.0089 0.0202 -0.0082 0.0485 -0.002 0.992884 1 1 1 1 1 2 4.466 2 4.466 2 4.466
3 4.466 4 4.466
N(1) 4.95(4) 0 0 0 0.070(18) 0.033(16) 0 0 -0.160(17) 0 0.191(18) 0 0 0.231(19)
0 0 0 0.06(2) 0 0 -0.01(2) 0 0 0 0.064(19) 0 0.998872 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(2) 5.32(4) 0 -0.036(16) -0.003(16) 0.008(15) 0.034(13) -0.008(13) -0.006(13)
0.006(12) -0.011(12) -0.019(15) 0.013(14) 0.024(14) -0.024(13) 0.020(13)
0.190(14) 0.055(12) 0.071(17) 0.005(16) -0.009(16) -0.003(16) -0.003(16)
0.011(16) 0.004(16) 0.007(15) -0.050(15) 0.994475 1 1 1 1 1 2 3.83936 2 3.83936
2 3.83936 3 3.83936 4 3.83936
N(3) 5.20(4) 0 -0.042(14) -0.031(17) -0.002(15) 0.046(15) 0.015(13) 0.049(13)
0.020(13) 0.027(13) 0.008(16) -0.004(14) 0.052(14) -0.005(14) -0.015(13)
0.182(13) 0.057(14) 0.002(19) 0.031(17) -0.041(17) -0.002(17) -0.010(17)
0.025(16) 0.016(16) 0.015(15) -0.039(15) 0.994475 1 1 1 1 1 2 3.83936 2 3.83936
2 3.83936 3 3.83936 4 3.83936
N(4) 4.89(4) 0 0 0 0.054(17) 0.065(15) 0 0 -0.092(14) 0 0.206(16) 0 0 0.111(15)
0 0 0 0.03(2) 0 0 -0.04(2) 0 0 0 0.024(17) 0 0.998872 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(5) 5.04(4) 0 0.054(16) 0.005(15) -0.010(14) -0.005(13) 0.044(13) 0.022(13)
-0.001(13) 0.001(14) 0.198(17) -0.012(13) 0.003(13) -0.010(15) 0.028(14)
-0.001(14) -0.160(14) 0.018(18) 0.006(17) -0.014(17) 0.022(16) -0.007(16)
-0.031(17) 0.054(17) 0.004(16) 0.013(16) 1.003441 1 1 1 1 1 2 3.83936 2 3.83936
2 3.83936 3 3.83936 4 3.83936
C(1) 4.16(6) 0 0.00(2) -0.03(2) 0.012(18) -0.183(19) 0.016(16) 0.003(17)
0.014(19) 0.015(19) 0.00(2) 0.015(19) 0.03(2) 0.025(19) -0.02(2) 0.26(2)
0.00(2) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(2) 4.10(6) 0 0.04(2) 0.01(3) 0.00(2) -0.15(2) -0.038(17) 0.005(18) 0.005(19)
0.037(19) 0.03(2) 0.01(2) 0.02(2) 0.00(2) 0.01(2) 0.23(2) 0.019(19) 0 0 0 0 0 0
0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(3) 4.17(6) 0 0.00(2) 0.02(2) 0.00(2) -0.143(18) 0.013(17) 0.021(18) 0.005(17)
-0.016(18) -0.01(2) 0.000(19) 0.05(2) -0.006(19) 0.016(19) 0.23(2) 0.010(19) 0
0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(4) 3.84(5) 0 0.02(2) 0.07(2) -0.005(19) -0.146(17) 0.035(15) -0.008(16)
0.044(17) -0.035(17) 0.01(2) 0.014(18) 0.02(2) -0.002(19) 0.011(19) 0.24(2)
-0.010(18) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(5) 4.09(6) 0 -0.02(2) -0.01(2) 0.002(18) -0.173(18) 0.002(15) -0.021(15)
0.009(17) 0.068(18) 0.04(2) 0.037(18) 0.02(2) -0.013(18) 0.004(19) 0.24(2)
-0.040(19) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(6) 3.88(5) 0 0.03(2) 0.11(2) 0.020(18) -0.115(18) 0.009(15) -0.014(15)
0.099(18) -0.103(18) 0.02(2) 0.035(19) 0.02(2) -0.019(19) 0.026(19) 0.15(2)
-0.009(19) 0 0 0 0 0 0 0 0 0 1.017365 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(7) 3.87(5) 0 -0.051(19) -0.01(2) 0.12(2) 0.146(17) 0.018(17) -0.007(17)
-0.145(16) -0.029(16) 0.27(2) -0.02(2) 0.01(2) 0.18(2) 0.019(19) -0.010(18)
0.003(18) 0 0 0 0 0 0 0 0 0 1.009819 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(8) 3.90(5) 0 0.01(2) 0.07(2) 0.009(18) -0.141(17) -0.023(16) 0.006(15)
0.025(16) -0.032(17) 0.03(2) 0.02(2) 0.038(18) 0.023(19) -0.01(2) 0.230(19)
-0.03(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(9) 4.06(6) 0 0.02(2) 0.01(2) 0.01(2) -0.145(18) 0.005(16) 0.027(17) 0.047(17)
0.014(18) 0.01(2) 0.019(19) 0.05(2) -0.01(2) -0.020(19) 0.207(19) 0.00(2) 0 0 0
0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(10) 3.96(6) 0 0.02(2) 0.01(2) 0.00(2) -0.187(19) 0.006(18) -0.001(16)
-0.020(18) -0.015(19) 0.04(2) 0.00(2) 0.04(2) 0.03(2) 0.03(2) 0.22(2) 0.00(2) 0
0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(11) 4.12(6) 0 -0.01(2) -0.04(2) 0.003(19) -0.164(19) 0.036(17) -0.034(17)
-0.036(18) 0.010(18) -0.02(2) -0.01(2) 0.04(2) 0.02(2) -0.03(2) 0.24(2)
-0.01(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(12) 3.94(6) 0 0.03(2) 0.11(2) -0.023(19) -0.115(16) 0.048(16) -0.011(16)
0.095(17) -0.096(17) 0.00(2) -0.001(18) 0.00(2) -0.004(19) 0.017(19) 0.22(2)
0.04(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762
4 3.1762
C(13) 4.05(5) 0 0.02(2) -0.05(2) -0.01(2) -0.145(17) -0.007(16) 0.014(16)
-0.021(16) 0.008(16) 0.01(2) 0.02(2) 0.022(18) 0.022(19) 0.008(19) 0.231(19)
-0.02(2) 0 0 0 0 0 0 0 0 0 1.01531 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(14) 4.34(7) 0 -0.03(3) -0.02(3) -0.14(2) -0.19(2) 0.02(2) 0.02(2) -0.03(2)
0.02(2) 0.21(3) 0.01(2) 0.00(2) 0.00(2) 0.01(2) 0.03(2) -0.14(3) 0 0 0 0 0 0 0
0 0 1.001636 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(15) 4.25(6) 0 0.05(2) -0.08(3) -0.13(2) -0.128(19) 0.056(17) -0.02(2)
-0.06(2) -0.01(2) 0.19(2) -0.02(2) 0.06(2) -0.01(2) -0.05(2) -0.05(2) -0.16(2)
0 0 0 0 0 0 0 0 0 1.001636 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(16) 4.14(7) 0 -0.01(3) 0.00(2) -0.01(2) -0.15(2) -0.045(19) 0.044(18)
-0.026(19) 0.02(2) 0.17(2) 0.05(2) 0.00(2) 0.03(2) -0.08(2) -0.010(19) -0.10(3)
0 0 0 0 0 0 0 0 0 1.001636 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(17) 4.21(7) 0 -0.04(2) -0.24(3) -0.09(2) -0.12(2) -0.036(19) 0.02(2) 0.01(2)
-0.04(2) 0.19(3) 0.00(2) 0.10(2) -0.08(2) -0.02(2) 0.01(2) -0.11(3) 0 0 0 0 0 0
0 0 0 1.001636 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(1) 0.87(3) 0 0 0 0.08(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2) 0.96(3) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.84(3) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5) 0.81(3) 0 0 0 0.13(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9) 0.87(3) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10) 0.90(3) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(11) 0.86(3) 0 0 0 0.05(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(13) 0.81(3) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14A) 0.88(4) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14B) 0.81(4) 0 0 0 0.15(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14C) 0.85(4) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15A) 0.85(4) 0 0 0 0.10(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15B) 0.94(3) 0 0 0 0.10(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15C) 0.87(4) 0 0 0 0.07(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16A) 0.93(3) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16B) 0.90(3) 0 0 0 0.20(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16C) 0.91(4) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17A) 0.86(3) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17B) 1.03(5) 0 0 0 0.13(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17C) 0.89(4) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2A) 0.69(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3A) 0.76(3) 0 0 0 0.11(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) H(3A) Z CL(1) H(2A) Y
O(1) C(7) X O(1) C(13) Y
O(2) N(1) X O(2) O(3) Y
O(3) N(1) -X O(3) O(2) Y
O(4) N(4) X O(4) O(5) Y
O(5) N(4) -X O(5) O(4) Y
N(1) C(6) Z N(1) O(2) Y
N(2) C(4) X N(2) C(7) Y
N(3) C(8) X N(3) C(7) Y
N(4) C(12) Z N(4) O(4) Y
N(5) C(15) Z N(5) C(16) Y
C(1) C(6) X C(1) C(2) Y
C(2) C(3) X C(2) C(1) Y
C(3) C(4) X C(3) C(2) Y
C(4) C(3) X C(4) C(5) Y
C(5) C(6) X C(5) C(4) Y
C(6) C(1) X C(6) C(5) Y
C(7) O(1) Z C(7) N(3) Y
C(8) C(9) X C(8) C(13) Y
C(9) C(10) X C(9) C(8) Y
C(10) C(11) X C(10) C(9) Y
C(11) C(12) X C(11) C(10) Y
C(12) C(13) X C(12) C(11) Y
C(13) C(8) X C(13) C(12) Y
C(14) N(5) Z C(14) H(14B) Y
C(15) N(5) Z C(15) H(15A) Y
C(16) N(5) Z C(16) H(16A) Y
C(17) N(5) Z C(17) H(17B) Y
H(1) C(1) Z H(1) C(6) Y
H(2) C(2) Z H(2) C(3) Y
H(3) C(3) Z H(3) C(4) Y
H(5) C(5) Z H(5) C(6) Y
H(9) C(9) Z H(9) C(10) Y
H(10) C(10) Z H(10) C(9) Y
H(11) C(11) Z H(11) C(12) Y
H(13) C(13) Z H(13) C(12) Y
H(14A) C(14) Z H(14A) H(14C) Y
H(14B) C(14) Z H(14B) H(14C) Y
H(14C) C(14) Z H(14C) H(14A) Y
H(15A) C(15) Z H(15A) H(15C) Y
H(15B) C(15) Z H(15B) H(15C) Y
H(15C) C(15) Z H(15C) H(15A) Y
H(16A) C(16) Z H(16A) H(16B) Y
H(16B) C(16) Z H(16B) H(16A) Y
H(16C) C(16) Z H(16C) H(16B) Y
H(17A) C(17) Z H(17A) H(17C) Y
H(17B) C(17) Z H(17B) H(17C) Y
H(17C) C(17) Z H(17C) H(17B) Y
H(2A) N(2) Z H(2A) C(7) Y
H(3A) N(3) Z H(3A) C(7) Y


#----------------------------------------------------------------------------#
#                   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
O(1) C(7) 1.2256(4) 1_555 1_555 yes
O(2) N(1) 1.2295(6) 1_555 1_555 yes
O(3) N(1) 1.2265(6) 1_555 1_555 yes
O(4) N(4) 1.2219(5) 1_555 1_555 yes
O(5) N(4) 1.2275(5) 1_555 1_555 yes
N(1) C(6) 1.4695(5) 1_555 1_555 yes
N(2) C(4) 1.3930(4) 1_555 1_555 yes
N(2) C(7) 1.3743(4) 1_555 1_555 yes
N(2) H(2A) 1.0243(3) 1_555 1_555 yes
N(3) C(7) 1.3787(4) 1_555 1_555 yes
N(3) C(8) 1.3922(4) 1_555 1_555 yes
N(3) H(3A) 1.0116(3) 1_555 1_555 yes
N(4) C(12) 1.4665(5) 1_555 1_555 yes
C(1) C(2) 1.3936(5) 1_555 1_555 yes
C(1) C(6) 1.3887(5) 1_555 1_555 yes
C(1) H(1) 1.0863(3) 1_555 1_555 yes
C(2) C(3) 1.3881(5) 1_555 1_555 yes
C(2) H(2) 1.0643(3) 1_555 1_555 yes
C(3) C(4) 1.4059(4) 1_555 1_555 yes
C(3) H(3) 1.0771(3) 1_555 1_555 yes
C(4) C(5) 1.3977(4) 1_555 1_555 yes
C(5) C(6) 1.3913(4) 1_555 1_555 yes
C(5) H(5) 1.0909(3) 1_555 1_555 yes
C(8) C(9) 1.4061(4) 1_555 1_555 yes
C(8) C(13) 1.3971(4) 1_555 1_555 yes
C(9) C(10) 1.3895(5) 1_555 1_555 yes
C(9) H(9) 1.0662(3) 1_555 1_555 yes
C(10) C(11) 1.3939(5) 1_555 1_555 yes
C(10) H(10) 1.0783(3) 1_555 1_555 yes
C(11) C(12) 1.3880(5) 1_555 1_555 yes
C(11) H(11) 1.0780(3) 1_555 1_555 yes
C(12) C(13) 1.3891(4) 1_555 1_555 yes
C(13) H(13) 1.0876(3) 1_555 1_555 yes
C(14) H(14A) 1.0782(6) 1_555 1_555 yes
C(14) H(14B) 1.1012(6) 1_555 1_555 yes
C(14) H(14C) 1.1040(6) 1_555 1_555 yes
C(15) H(15A) 1.0860(6) 1_555 1_555 yes
C(15) H(15B) 1.0890(4) 1_555 1_555 yes
C(15) H(15C) 1.0762(5) 1_555 1_555 yes
C(16) H(16A) 1.0744(5) 1_555 1_555 yes
C(16) H(16B) 1.1083(4) 1_555 1_555 yes
C(16) H(16C) 1.0694(5) 1_555 1_555 yes
C(17) H(17A) 1.1172(5) 1_555 1_555 yes
C(17) H(17B) 1.0425(8) 1_555 1_555 yes
C(17) H(17C) 1.0866(6) 1_555 1_555 yes

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
O(2) N(1) O(3) 122.98(5) 1_555 1_555 1_555 yes
O(2) N(1) C(6) 118.50(3) 1_555 1_555 1_555 yes
O(3) N(1) C(6) 118.51(4) 1_555 1_555 1_555 yes
C(4) N(2) C(7) 127.47(3) 1_555 1_555 1_555 yes
C(4) N(2) H(2A) 116.09(3) 1_555 1_555 1_555 yes
C(7) N(2) H(2A) 115.49(3) 1_555 1_555 1_555 yes
C(7) N(3) C(8) 127.44(3) 1_555 1_555 1_555 yes
C(7) N(3) H(3A) 115.27(3) 1_555 1_555 1_555 yes
C(8) N(3) H(3A) 116.94(3) 1_555 1_555 1_555 yes
O(4) N(4) O(5) 122.94(5) 1_555 1_555 1_555 yes
O(4) N(4) C(12) 118.64(4) 1_555 1_555 1_555 yes
O(5) N(4) C(12) 118.42(3) 1_555 1_555 1_555 yes
C(2) C(1) C(6) 117.18(3) 1_555 1_555 1_555 yes
C(2) C(1) H(1) 121.82(3) 1_555 1_555 1_555 yes
C(6) C(1) H(1) 121.00(3) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 120.64(3) 1_555 1_555 1_555 yes
C(1) C(2) H(2) 118.53(3) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 120.81(4) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 120.98(3) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 119.60(3) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 119.38(3) 1_555 1_555 1_555 yes
N(2) C(4) C(3) 116.54(3) 1_555 1_555 1_555 yes
N(2) C(4) C(5) 124.12(3) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.34(3) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 117.82(3) 1_555 1_555 1_555 yes
C(4) C(5) H(5) 121.01(3) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 121.17(3) 1_555 1_555 1_555 yes
N(1) C(6) C(1) 118.39(3) 1_555 1_555 1_555 yes
N(1) C(6) C(5) 117.57(3) 1_555 1_555 1_555 yes
C(1) C(6) C(5) 124.03(3) 1_555 1_555 1_555 yes
O(1) C(7) N(2) 124.52(3) 1_555 1_555 1_555 yes
O(1) C(7) N(3) 124.44(3) 1_555 1_555 1_555 yes
N(2) C(7) N(3) 111.02(3) 1_555 1_555 1_555 yes
N(3) C(8) C(9) 117.16(3) 1_555 1_555 1_555 yes
N(3) C(8) C(13) 123.71(3) 1_555 1_555 1_555 yes
C(9) C(8) C(13) 119.13(3) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 120.94(3) 1_555 1_555 1_555 yes
C(8) C(9) H(9) 119.19(3) 1_555 1_555 1_555 yes
C(10) C(9) H(9) 119.86(3) 1_555 1_555 1_555 yes
C(9) C(10) C(11) 120.70(3) 1_555 1_555 1_555 yes
C(9) C(10) H(10) 119.13(3) 1_555 1_555 1_555 yes
C(11) C(10) H(10) 120.18(3) 1_555 1_555 1_555 yes
C(10) C(11) C(12) 117.16(3) 1_555 1_555 1_555 yes
C(10) C(11) H(11) 123.09(3) 1_555 1_555 1_555 yes
C(12) C(11) H(11) 119.76(3) 1_555 1_555 1_555 yes
N(4) C(12) C(11) 118.76(3) 1_555 1_555 1_555 yes
N(4) C(12) C(13) 117.32(3) 1_555 1_555 1_555 yes
C(11) C(12) C(13) 123.92(3) 1_555 1_555 1_555 yes
C(8) C(13) C(12) 118.15(3) 1_555 1_555 1_555 yes
C(8) C(13) H(13) 121.19(3) 1_555 1_555 1_555 yes
C(12) C(13) H(13) 120.64(3) 1_555 1_555 1_555 yes
H(14A) C(14) H(14B) 110.92(5) 1_555 1_555 1_555 yes
H(14A) C(14) H(14C) 110.73(5) 1_555 1_555 1_555 yes
H(14B) C(14) H(14C) 109.58(6) 1_555 1_555 1_555 yes
H(15A) C(15) H(15B) 112.54(4) 1_555 1_555 1_555 yes
H(15A) C(15) H(15C) 110.21(4) 1_555 1_555 1_555 yes
H(15B) C(15) H(15C) 110.24(4) 1_555 1_555 1_555 yes
H(16A) C(16) H(16B) 108.87(4) 1_555 1_555 1_555 yes
H(16A) C(16) H(16C) 110.74(4) 1_555 1_555 1_555 yes
H(16B) C(16) H(16C) 111.51(4) 1_555 1_555 1_555 yes
H(17A) C(17) H(17B) 110.14(5) 1_555 1_555 1_555 yes
H(17A) C(17) H(17C) 109.19(5) 1_555 1_555 1_555 yes
H(17B) C(17) H(17C) 112.01(4) 1_555 1_555 1_555 yes
_database_code_depnum_ccdc_archive 'CCDC 953244'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_crystalstructure_8
#==============================================================================

# CHEMICAL DATA
_chemical_name_systematic        
;
1,3-bis(3,5-dinitrophenyl)urea with tetramethylacetate
;
_chemical_formula_moiety         'C13 H8 N6 O9, C4 H12 N, C2 H3 O2'
_chemical_formula_sum            'C19 H23 N7 O11'
_chemical_formula_weight         525.44

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

#==============================================================================

# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.602(3)
_cell_length_b                   10.807(3)
_cell_length_c                   12.433(4)
_cell_angle_alpha                109.859(5)
_cell_angle_beta                 96.598(3)
_cell_angle_gamma                103.5372(5)
_cell_volume                     1152.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    4163
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      31.5

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_exptl_special_details           
;
 ?
;

#==============================================================================

# EXPERIMENTAL DATA
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.68890
_diffrn_source_type              'DLS beamline I19'
_diffrn_source                   synchrotron
_diffrn_radiation_collimation    'Confocal mirrors'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            179628
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         50.02
_reflns_number_total             23530
_reflns_number_gt                19417
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         18361
_refine_ls_number_parameters     969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.054
_refine_ls_R_factor_gt           0.04
_refine_ls_wR_factor_ref         0.046
_refine_ls_goodness_of_fit_ref   1.62
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.052
_diffrn_measured_fraction_theta_max 0.725
_diffrn_reflns_theta_full        48.9
_diffrn_measured_fraction_theta_full 81.8

#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_occupancy
_atom_site_symmetry_multiplicity
O(1) O 0.24884(4) 0.47710(5) -0.06770(4) 0.019 1 2
O(2) O -0.11315(7) 0.12198(7) -0.29265(5) 0.031 1 2
O(3) O -0.32859(7) 0.04467(8) -0.26170(7) 0.041 1 2
O(4) O -0.37502(5) 0.12717(5) 0.14271(6) 0.029 1 2
O(5) O -0.21646(6) 0.30420(6) 0.28143(6) 0.029 1 2
O(6) O 0.76423(6) 0.78854(9) -0.19966(6) 0.035 1 2
O(7) O 0.54772(6) 0.64201(7) -0.25865(5) 0.031 1 2
O(8) O 0.94471(5) 1.06391(5) 0.21397(5) 0.027 1 2
O(9) O 0.84403(5) 0.99410(6) 0.33903(5) 0.027 1 2
O(10) O 0.21321(6) 0.61973(9) 0.33736(7) 0.033 1 2
O(11) O 0.45105(5) 0.70287(8) 0.34586(5) 0.027 1 2
N(3) N 0.17745(4) 0.47355(4) 0.10276(4) 0.017 1 2
N(1) N -0.19994(4) 0.11414(4) -0.22769(5) 0.024 1 2
N(2) N -0.26180(4) 0.22381(4) 0.17832(5) 0.022 1 2
N(4) N 0.39228(4) 0.62467(4) 0.11285(4) 0.017 1 2
N(5) N 0.65071(4) 0.72643(4) -0.18149(4) 0.021 1 2
N(6) N 0.84909(4) 0.98671(4) 0.23876(4) 0.02 1 2
N(7) N 0.19707(4) 0.32455(4) -0.45941(4) 0.018 1 2
C(1) C -0.23230(4) 0.16512(4) -0.02524(5) 0.02 1 2
C(6) C -0.14510(4) 0.19324(4) -0.10105(4) 0.019 1 2
C(5) C -0.00988(4) 0.29283(4) -0.06509(4) 0.018 1 2
C(4) C 0.04428(3) 0.37143(4) 0.05531(4) 0.016 1 2
C(3) C -0.04037(4) 0.34594(4) 0.13492(4) 0.017 1 2
C(2) C -0.17445(4) 0.24523(4) 0.09295(5) 0.018 1 2
C(7) C 0.27085(3) 0.52130(4) 0.03979(4) 0.016 1 2
C(8) C 0.50543(3) 0.69828(4) 0.07877(4) 0.015 1 2
C(13) C 0.51755(4) 0.67370(4) -0.03777(4) 0.016 1 2
C(12) C 0.63927(4) 0.75400(4) -0.05882(4) 0.017 1 2
C(11) C 0.75143(4) 0.85707(4) 0.02800(4) 0.018 1 2
C(10) C 0.73424(4) 0.87883(4) 0.14213(4) 0.016 1 2
C(9) C 0.61517(4) 0.80477(4) 0.16969(4) 0.016 1 2
C(14) C 0.20930(6) 0.18283(5) -0.51984(5) 0.025 1 2
C(15) C 0.04852(8) 0.33077(9) -0.50131(9) 0.039 1 2
C(16) C 0.22221(7) 0.36014(6) -0.32982(5) 0.026 1 2
C(17) C 0.31330(8) 0.42531(6) -0.48308(7) 0.031 1 2
C(18) C 0.33827(5) 0.70104(5) 0.38989(5) 0.023 1 2
C(19) C 0.35710(7) 0.80617(10) 0.51132(7) 0.038 1 2
H(3A) H 0.198024 0.525642 0.190083 0.044 1 2
H(1) H -0.338269 0.088004 -0.057868 0.048 1 2
H(5) H 0.048973 0.308457 -0.130904 0.04 1 2
H(3) H -0.001483 0.406112 0.227802 0.038 1 2
H(13) H 0.435743 0.593667 -0.110711 0.041 1 2
H(11) H 0.845112 0.917828 0.009068 0.047 1 2
H(9) H 0.604395 0.827433 0.25961 0.04 1 2
H(4A) H 0.405369 0.645231 0.199467 0.041 1 2
H(14A) H 0.313875 0.181567 -0.483209 0.053 1 2
H(14B) H 0.197552 0.164597 -0.610112 0.054 1 2
H(14C) H 0.126474 0.11361 -0.501613 0.056 1 2
H(15A) H 0.035825 0.311085 -0.591873 0.073 1 2
H(15B) H 0.045447 0.43273 -0.457823 0.069 1 2
H(15C) H -0.025178 0.262726 -0.474999 0.074 1 2
H(16A) H 0.331452 0.361144 -0.303366 0.054 1 2
H(16B) H 0.145085 0.28454 -0.313462 0.062 1 2
H(16C) H 0.205368 0.458088 -0.293997 0.052 1 2
H(17A) H 0.412989 0.411568 -0.450422 0.06 1 2
H(17B) H 0.303104 0.524578 -0.439295 0.059 1 2
H(17C) H 0.292312 0.400223 -0.574623 0.067 1 2
H(19A) H 0.457648 0.833595 0.570923 0.058 1 2
H(19B) H 0.281702 0.765722 0.555402 0.058 1 2
H(19C) H 0.342134 0.897231 0.503994 0.058 1 2



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
O(1) 5.86(3) 0 -0.103(16) -0.026(14) -0.030(15) -0.125(16) -0.085(15)
-0.031(14) -0.100(14) -0.023(14) 0.026(12) -0.005(12) -0.002(11) -0.009(11)
-0.007(12) 0.019(11) -0.015(12) 0.064(16) -0.004(15) 0.026(14) -0.007(15)
-0.051(15) 0.010(14) -0.046(15) 0.005(14) -0.004(14) 0.990615 1 1 1 1 1
O(2) 6.04(3) 0 -0.041(14) 0.070(14) -0.042(15) -0.101(18) 0.020(15) -0.097(15)
-0.122(14) 0.017(14) 0.028(13) 0.130(13) -0.027(12) -0.049(11) 0.007(12)
0.089(11) 0.030(11) 0.039(17) 0.016(16) 0.012(15) 0.033(16) 0.006(16) 0.009(14)
0.023(14) 0.023(13) -0.026(14) 0.969803 1 1 1 1 1
O(3) 6.04(3) 0 -0.041(14) 0.070(14) -0.042(15) -0.101(18) 0.020(15) -0.097(15)
-0.122(14) 0.017(14) 0.028(13) 0.130(13) -0.027(12) -0.049(11) 0.007(12)
0.089(11) 0.030(11) 0.039(17) 0.016(16) 0.012(15) 0.033(16) 0.006(16) 0.009(14)
0.023(14) 0.023(13) -0.026(14) 0.969803 1 1 1 1 1
O(4) 6.01(2) 0 -0.024(13) -0.050(13) -0.065(13) -0.101(14) 0.017(12) 0.014(13)
-0.129(13) 0.037(14) -0.005(10) 0.073(10) 0.049(11) -0.049(10) -0.009(10)
0.100(10) 0.027(11) -0.027(14) 0.000(12) 0.005(13) -0.019(13) 0.000(13)
-0.002(12) 0.006(13) -0.011(13) 0.012(13) 0.969803 1 1 1 1 1
O(5) 6.01(2) 0 -0.024(13) -0.050(13) -0.065(13) -0.101(14) 0.017(12) 0.014(13)
-0.129(13) 0.037(14) -0.005(10) 0.073(10) 0.049(11) -0.049(10) -0.009(10)
0.100(10) 0.027(11) -0.027(14) 0.000(12) 0.005(13) -0.019(13) 0.000(13)
-0.002(12) 0.006(13) -0.011(13) 0.012(13) 0.969803 1 1 1 1 1
O(6) 6.03(2) 0 -0.038(12) 0.004(13) -0.068(17) -0.083(17) 0.014(14) -0.018(16)
-0.107(13) 0.051(13) -0.056(14) 0.102(12) 0.017(13) 0.003(11) -0.012(11)
0.063(10) 0.044(10) 0.009(18) 0.001(15) -0.020(17) -0.008(16) 0.003(16)
0.017(13) 0.011(13) 0.016(12) 0.004(12) 0.969803 1 1 1 1 1
O(7) 6.03(2) 0 -0.038(12) 0.004(13) -0.068(17) -0.083(17) 0.014(14) -0.018(16)
-0.107(13) 0.051(13) -0.056(14) 0.102(12) 0.017(13) 0.003(11) -0.012(11)
0.063(10) 0.044(10) 0.009(18) 0.001(15) -0.020(17) -0.008(16) 0.003(16)
0.017(13) 0.011(13) 0.016(12) 0.004(12) 0.969803 1 1 1 1 1
O(8) 6.06(2) 0 -0.036(13) -0.002(12) 0.006(13) -0.094(14) 0.041(13) -0.067(12)
-0.103(12) 0.017(12) -0.083(11) 0.038(11) -0.020(10) 0.006(9) 0.015(10)
0.084(10) 0.008(10) 0.039(14) -0.010(13) 0.018(12) 0.019(13) 0.048(13)
-0.035(12) -0.002(12) 0.024(13) 0.000(13) 0.969803 1 1 1 1 1
O(9) 6.06(2) 0 -0.036(13) -0.002(12) 0.006(13) -0.094(14) 0.041(13) -0.067(12)
-0.103(12) 0.017(12) -0.083(11) 0.038(11) -0.020(10) 0.006(9) 0.015(10)
0.084(10) 0.008(10) 0.039(14) -0.010(13) 0.018(12) 0.019(13) 0.048(13)
-0.035(12) -0.002(12) 0.024(13) 0.000(13) 0.969803 1 1 1 1 1
O(10) 6.22(4) 0 -0.230(16) 0.055(17) -0.04(2) -0.08(2) 0.04(2) 0.00(2)
0.026(16) 0.016(15) 0.13(2) 0.016(17) 0.060(19) -0.022(16) 0.017(15) 0.007(12)
0.017(12) 0.00(3) -0.01(2) 0.00(2) 0.00(2) -0.01(2) 0.018(18) -0.018(18)
0.042(14) -0.031(14) 0.939765 1 1 1 1 1
O(11) 6.31(4) 0 0.085(16) 0.021(16) -0.053(19) -0.07(2) -0.009(18) -0.019(18)
-0.016(15) 0.071(15) -0.072(17) 0.026(16) 0.004(15) -0.063(14) 0.013(14)
0.061(11) 0.047(11) 0.04(2) -0.03(2) 0.041(19) 0.036(19) 0.011(19) -0.043(16)
0.042(17) 0.000(13) 0.012(14) 0.939765 1 1 1 1 1
N(3) 5.03(4) 0 -0.009(15) -0.050(18) -0.007(15) -0.042(15) -0.068(13)
-0.024(15) 0.026(15) 0.034(15) 0.024(14) -0.008(12) 0.022(14) 0.014(14)
-0.021(13) 0.160(14) 0.042(14) 0.063(18) -0.013(15) -0.048(17) -0.027(17)
-0.060(16) -0.050(17) -0.011(17) 0.064(17) -0.022(18) 0.977935 1 1 1 1 1
N(1) 4.93(4) 0 0 0 -0.112(18) 0.041(18) 0 0 -0.223(19) 0 0.149(18) 0 0
0.143(18) 0 0 0 0.01(2) 0 0 -0.04(2) 0 0 0 0.09(2) 0 0.963181 1 1 1 1 1
N(2) 4.99(4) 0 0 0 0.027(18) 0.044(18) 0 0 -0.228(17) 0 0.150(18) 0 0 0.111(17)
0 0 0 0.02(2) 0 0 -0.02(2) 0 0 0 0.046(18) 0 0.963181 1 1 1 1 1
N(4) 4.94(4) 0 -0.077(17) -0.087(17) -0.018(15) -0.064(15) -0.031(14) 0.062(14)
-0.024(15) 0.030(15) -0.002(14) 0.035(13) 0.025(13) 0.007(13) -0.001(14)
0.148(14) 0.068(14) 0.078(18) 0.035(16) 0.009(16) 0.052(17) 0.011(17) 0.064(17)
0.023(17) -0.019(18) -0.015(17) 0.977935 1 1 1 1 1
N(5) 5.02(4) 0 0 0 0.051(18) 0.034(19) 0 0 -0.208(17) 0 0.170(18) 0 0 0.126(17)
0 0 0 0.05(2) 0 0 0.05(2) 0 0 0 0.065(18) 0 0.963181 1 1 1 1 1
N(6) 4.86(4) 0 0 0 0.005(16) 0.089(15) 0 0 -0.146(18) 0 0.161(17) 0 0 0.133(18)
0 0 0 0.09(2) 0 0 -0.04(2) 0 0 0 -0.01(2) 0 0.963181 1 1 1 1 1
N(7) 4.90(4) 0 -0.043(17) 0.014(17) -0.032(15) 0.031(14) 0.067(14) 0.001(14)
0.004(16) 0.039(16) 0.178(14) -0.008(12) 0.000(13) 0.008(13) 0.025(14)
-0.018(15) -0.096(15) 0.000(18) -0.009(16) 0.021(17) 0.045(17) -0.041(17)
-0.024(18) 0.051(18) 0.033(19) 0.009(19) 0.974082 1 1 1 1 1
C(1) 4.05(7) 0 0.04(2) -0.14(2) -0.02(2) -0.198(19) 0.029(19) 0.051(17)
-0.02(2) 0.07(2) 0.00(2) -0.01(2) 0.065(18) -0.01(2) -0.05(2) 0.12(2) 0.03(2) 0
0 0 0 0 0 0 0 0 0.957801 1 1 1 1 1
C(6) 4.15(6) 0 0.02(2) 0.04(2) -0.017(19) -0.150(19) 0.008(19) -0.074(17)
0.08(2) -0.11(2) 0.03(2) 0.02(2) 0.054(18) -0.01(2) 0.023(19) 0.33(2) 0.04(2) 0
0 0 0 0 0 0 0 0 0.957801 1 1 1 1 1
C(5) 4.05(7) 0 -0.02(2) -0.13(2) 0.007(19) -0.202(19) 0.090(17) -0.031(18)
0.012(19) 0.06(2) 0.030(19) 0.035(18) 0.03(2) 0.013(19) 0.022(19) 0.18(2)
-0.02(2) 0 0 0 0 0 0 0 0 0 0.957801 1 1 1 1 1
C(4) 4.00(6) 0 -0.02(2) 0.17(2) -0.006(18) -0.212(18) 0.019(18) -0.087(16)
0.028(19) -0.030(19) 0.021(19) -0.012(19) -0.020(17) -0.011(19) 0.037(19)
0.25(2) -0.01(2) 0 0 0 0 0 0 0 0 0 0.957801 1 1 1 1 1
C(3) 4.21(6) 0 0.01(2) 0.04(2) 0.02(2) -0.231(18) 0.005(18) 0.062(17)
-0.010(19) -0.03(2) 0.02(2) 0.048(19) 0.016(18) 0.01(2) 0.011(19) 0.22(2)
-0.06(2) 0 0 0 0 0 0 0 0 0 0.957801 1 1 1 1 1
C(2) 4.19(6) 0 -0.07(2) 0.21(2) 0.005(19) -0.194(19) -0.059(17) 0.029(19)
0.059(19) -0.14(2) -0.003(19) 0.063(17) -0.03(2) -0.01(2) 0.007(19) 0.30(2)
0.05(2) 0 0 0 0 0 0 0 0 0 0.957801 1 1 1 1 1
C(7) 4.12(6) 0 -0.007(19) 0.01(2) 0.09(2) 0.19(2) 0.106(18) 0.026(19)
-0.189(17) -0.073(16) 0.34(2) 0.05(2) 0.02(2) 0.22(2) 0.02(2) -0.005(17)
0.033(17) 0 0 0 0 0 0 0 0 0 0.956613 1 1 1 1 1
C(8) 4.01(6) 0 0.05(2) 0.05(2) -0.022(19) -0.196(18) -0.072(16) 0.021(18)
-0.001(18) 0.025(19) -0.024(19) 0.016(17) 0.031(19) -0.023(19) -0.008(19)
0.32(2) 0.00(2) 0 0 0 0 0 0 0 0 0 0.960001 1 1 1 1 1
C(13) 4.12(6) 0 0.01(2) 0.00(2) -0.015(19) -0.236(19) -0.041(18) -0.074(16)
-0.026(19) -0.039(19) 0.016(19) 0.01(2) 0.037(17) 0.007(19) 0.008(19) 0.19(2)
-0.01(2) 0 0 0 0 0 0 0 0 0 0.960001 1 1 1 1 1
C(12) 4.10(6) 0 0.01(2) 0.09(2) -0.011(19) -0.149(18) 0.063(17) -0.057(17)
0.082(19) -0.091(19) -0.017(19) -0.002(18) 0.021(18) 0.014(19) -0.010(19)
0.26(2) 0.04(2) 0 0 0 0 0 0 0 0 0 0.960001 1 1 1 1 1
C(11) 4.04(6) 0 -0.05(2) 0.00(2) 0.028(19) -0.237(19) 0.076(17) -0.036(19)
-0.015(19) 0.07(2) 0.01(2) 0.018(18) 0.00(2) 0.033(19) 0.027(19) 0.24(2)
-0.03(2) 0 0 0 0 0 0 0 0 0 0.960001 1 1 1 1 1
C(10) 4.11(6) 0 0.03(2) 0.06(2) -0.003(19) -0.152(18) 0.042(19) 0.078(16)
0.059(19) -0.143(19) -0.011(19) 0.00(2) -0.005(17) 0.001(19) -0.010(18) 0.27(2)
0.04(2) 0 0 0 0 0 0 0 0 0 0.960001 1 1 1 1 1
C(9) 4.02(6) 0 -0.04(2) -0.05(2) 0.013(19) -0.237(18) -0.025(17) 0.066(17)
0.019(19) 0.017(19) -0.025(19) 0.029(18) 0.022(18) -0.050(19) 0.017(19) 0.19(2)
0.01(2) 0 0 0 0 0 0 0 0 0 0.960001 1 1 1 1 1
C(14) 4.45(8) 0 0.00(3) 0.04(3) -0.07(2) -0.17(2) 0.015(19) 0.00(2) 0.07(2)
-0.05(2) 0.22(2) -0.008(19) -0.02(2) 0.01(2) 0.06(2) 0.03(2) -0.22(2) 0 0 0 0 0
0 0 0 0 0.938606 1 1 1 1 1
C(15) 4.27(9) 0 -0.13(3) 0.19(4) -0.10(2) -0.08(2) -0.04(2) 0.02(3) -0.02(3)
0.03(3) 0.18(3) 0.06(2) -0.12(3) -0.13(3) -0.05(3) 0.03(3) -0.47(3) 0 0 0 0 0 0
0 0 0 0.938606 1 1 1 1 1
C(16) 4.41(8) 0 -0.04(3) -0.14(3) 0.03(2) -0.13(2) 0.01(2) -0.05(2) -0.08(2)
0.05(2) 0.14(3) 0.03(2) 0.03(2) -0.11(2) 0.05(2) 0.10(2) -0.14(2) 0 0 0 0 0 0 0
0 0 0.938606 1 1 1 1 1
C(17) 4.20(9) 0 -0.21(3) 0.07(3) -0.04(2) -0.10(2) -0.10(2) 0.03(2) 0.04(3)
-0.02(3) 0.16(3) 0.04(2) -0.02(2) 0.06(2) -0.10(2) -0.05(2) -0.05(3) 0 0 0 0 0
0 0 0 0 0.938606 1 1 1 1 1
C(18) 3.95(6) 0 -0.07(2) 0.16(2) -0.10(2) 0.02(2) -0.06(2) -0.08(2) -0.34(2)
-0.03(2) 0.24(2) -0.03(2) -0.03(2) 0.31(2) -0.04(2) 0.03(2) 0.01(2) 0 0 0 0 0 0
0 0 0 0.969953 1 1 1 1 1
C(19) 5.90(12) 0 0.03(4) 0.06(3) -0.10(3) -0.02(2) -0.09(3) 0.07(2) -0.18(3)
-0.15(3) 0.18(3) 0.01(3) -0.07(2) -0.02(3) 0.06(3) 0.03(3) 0.00(3) 0 0 0 0 0 0
0 0 0 0.836455 1 1 1 1 1
H(3A) 0.78(3) 0 0 0 0.02(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(1) 0.84(3) 0 0 0 0.10(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(5) 0.78(4) 0 0 0 0.14(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(3) 0.83(3) 0 0 0 0.14(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(13) 0.93(3) 0 0 0 0.15(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(11) 0.89(3) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(9) 0.87(3) 0 0 0 0.14(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(4A) 0.72(3) 0 0 0 0.02(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(14A) 0.79(4) 0 0 0 0.01(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(14B) 0.82(4) 0 0 0 0.06(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(14C) 0.88(4) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(15A) 0.85(5) 0 0 0 0.05(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(15B) 0.66(4) 0 0 0 0.05(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(15C) 0.84(5) 0 0 0 0.20(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(16A) 0.87(4) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(16B) 0.82(4) 0 0 0 0.03(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(16C) 0.87(4) 0 0 0 0.09(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(17A) 0.87(4) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(17B) 0.91(4) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(17C) 0.87(5) 0 0 0 0.02(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(19A) 0.48(4) 0 0 0 0.07(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(19B) 0.60(4) 0 0 0 0.01(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2
H(19C) 0.52(5) 0 0 0 0.13(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(7) X O(1) C(13) Y
O(2) N(1) X O(2) O(3) Y
O(3) N(1) -X O(3) O(2) Y
O(4) N(2) X O(4) O(5) Y
O(5) N(2) -X O(5) O(4) Y
O(6) N(5) X O(6) O(7) Y
O(7) N(5) -X O(7) O(6) Y
O(8) N(6) X O(8) O(9) Y
O(9) N(6) -X O(9) O(8) Y
O(10) C(18) X O(10) O(11) Y
O(11) C(18) X O(11) O(10) Y
N(3) C(4) X N(3) C(7) Y
N(1) C(6) Z N(1) O(2) Y
N(2) C(2) Z N(2) O(5) Y
N(4) C(8) X N(4) C(7) Y
N(5) C(12) Z N(5) O(6) Y
N(6) C(10) Z N(6) O(8) Y
N(7) C(15) Z N(7) C(16) Y
C(1) C(6) X C(1) C(2) Y
C(6) C(1) X C(6) C(5) Y
C(5) C(6) X C(5) C(4) Y
C(4) C(3) X C(4) C(5) Y
C(3) C(4) X C(3) C(2) Y
C(2) C(3) X C(2) C(1) Y
C(7) O(1) Z C(7) N(4) Y
C(8) C(9) X C(8) C(13) Y
C(13) C(8) X C(13) C(12) Y
C(12) C(13) X C(12) C(11) Y
C(11) C(12) X C(11) C(10) Y
C(10) C(11) X C(10) C(9) Y
C(9) C(10) X C(9) C(8) Y
C(14) N(7) Z C(14) H(14B) Y
C(15) N(7) Z C(15) H(15A) Y
C(16) N(7) Z C(16) H(16A) Y
C(17) N(7) Z C(17) H(17B) Y
C(18) C(19) Z C(18) O(10) Y
C(19) C(18) Z C(19) H(19B) Y
H(3A) N(3) Z H(3A) C(7) Y
H(1) C(1) Z H(1) C(6) Y
H(5) C(5) Z H(5) C(6) Y
H(3) C(3) Z H(3) C(2) Y
H(13) C(13) Z H(13) C(12) Y
H(11) C(11) Z H(11) C(12) Y
H(9) C(9) Z H(9) C(10) Y
H(4A) N(4) Z H(4A) C(7) Y
H(14A) C(14) Z H(14A) H(14C) Y
H(14B) C(14) Z H(14B) H(14C) Y
H(14C) C(14) Z H(14C) H(14A) Y
H(15A) C(15) Z H(15A) H(15C) Y
H(15B) C(15) Z H(15B) H(15C) Y
H(15C) C(15) Z H(15C) H(15A) Y
H(16A) C(16) Z H(16A) H(16B) Y
H(16B) C(16) Z H(16B) H(16A) Y
H(16C) C(16) Z H(16C) H(16B) Y
H(17A) C(17) Z H(17A) H(17C) Y
H(17B) C(17) Z H(17B) H(17C) Y
H(17C) C(17) Z H(17C) H(17B) Y
H(19A) C(19) Z H(19A) H(19B) Y
H(19B) C(19) Z H(19B) H(19A) Y
H(19C) C(19) Z H(19C) H(19B) Y

#----------------------------------------------------------------------------#
#                   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
O(1) C(7) 1.2300(7) 1_555 1_555 yes
O(2) N(1) 1.2338(9) 1_555 1_555 yes
O(3) N(1) 1.2241(7) 1_555 1_555 yes
O(4) N(2) 1.2297(6) 1_555 1_555 yes
O(5) N(2) 1.2352(7) 1_555 1_555 yes
O(6) N(5) 1.2276(7) 1_555 1_555 yes
O(7) N(5) 1.2229(6) 1_555 1_555 yes
O(8) N(6) 1.2310(7) 1_555 1_555 yes
O(9) N(6) 1.2292(7) 1_555 1_555 yes
O(10) C(18) 1.2556(7) 1_555 1_555 yes
O(11) C(18) 1.2674(7) 1_555 1_555 yes
N(3) C(4) 1.3873(5) 1_555 1_555 yes
N(3) C(7) 1.3794(6) 1_555 1_555 yes
N(3) H(3A) 1.0090(4) 1_555 1_555 yes
N(4) C(7) 1.3748(5) 1_555 1_555 yes
N(4) C(8) 1.3867(6) 1_555 1_555 yes
N(4) H(4A) 1.0090(5) 1_555 1_555 yes
N(6) C(10) 1.4699(5) 1_555 1_555 yes
C(1) C(6) 1.3924(8) 1_555 1_555 yes
C(1) C(2) 1.3930(7) 1_555 1_555 yes
C(1) H(1) 1.0830(4) 1_555 1_555 yes
C(6) C(5) 1.3891(5) 1_555 1_555 yes
C(5) C(4) 1.4083(6) 1_555 1_555 yes
C(5) H(5) 1.0830(5) 1_555 1_555 yes
C(4) C(3) 1.4077(7) 1_555 1_555 yes
C(3) C(2) 1.3850(5) 1_555 1_555 yes
C(3) H(3) 1.0830(4) 1_555 1_555 yes
C(8) C(13) 1.4054(6) 1_555 1_555 yes
C(8) C(9) 1.4097(5) 1_555 1_555 yes
C(13) C(12) 1.3919(6) 1_555 1_555 yes
C(13) H(13) 1.0830(3) 1_555 1_555 yes
C(12) C(11) 1.3857(5) 1_555 1_555 yes
C(11) C(10) 1.3933(7) 1_555 1_555 yes
C(11) H(11) 1.0830(4) 1_555 1_555 yes
C(10) C(9) 1.3832(6) 1_555 1_555 yes
C(9) H(9) 1.0830(5) 1_555 1_555 yes
C(14) H(14A) 1.0590(5) 1_555 1_555 yes
C(14) H(14B) 1.0590(7) 1_555 1_555 yes
C(14) H(14C) 1.0590(7) 1_555 1_555 yes
C(15) H(15A) 1.0590(12) 1_555 1_555 yes
C(15) H(15B) 1.0590(8) 1_555 1_555 yes
C(15) H(15C) 1.0590(13) 1_555 1_555 yes
C(16) H(16A) 1.0590(6) 1_555 1_555 yes
C(16) H(16B) 1.0590(7) 1_555 1_555 yes
C(16) H(16C) 1.0590(6) 1_555 1_555 yes
C(17) H(17A) 1.0590(9) 1_555 1_555 yes
C(17) H(17B) 1.0590(7) 1_555 1_555 yes
C(17) H(17C) 1.0590(8) 1_555 1_555 yes
C(18) C(19) 1.5095(7) 1_555 1_555 yes
C(19) H(19A) 1.0590(8) 1_555 1_555 yes
C(19) H(19B) 1.0590(9) 1_555 1_555 yes
C(19) H(19C) 1.0590(13) 1_555 1_555 yes

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
C(4) N(3) C(7) 125.55(4) 1_555 1_555 1_555 yes
C(4) N(3) H(3A) 115.48(4) 1_555 1_555 1_555 yes
C(7) N(3) H(3A) 118.26(3) 1_555 1_555 1_555 yes
O(2) N(1) O(3) 124.18(7) 1_555 1_555 1_555 yes
O(4) N(2) O(5) 124.16(7) 1_555 1_555 1_555 yes
C(7) N(4) C(8) 126.28(4) 1_555 1_555 1_555 yes
C(7) N(4) H(4A) 117.70(4) 1_555 1_555 1_555 yes
C(8) N(4) H(4A) 115.86(3) 1_555 1_555 1_555 yes
O(6) N(5) O(7) 124.13(7) 1_555 1_555 1_555 yes
O(8) N(6) O(9) 124.09(5) 1_555 1_555 1_555 yes
O(8) N(6) C(10) 117.76(5) 1_555 1_555 1_555 yes
O(9) N(6) C(10) 118.15(4) 1_555 1_555 1_555 yes
C(6) C(1) C(2) 115.07(3) 1_555 1_555 1_555 yes
C(6) C(1) H(1) 121.29(5) 1_555 1_555 1_555 yes
C(2) C(1) H(1) 123.62(5) 1_555 1_555 1_555 yes
C(1) C(6) C(5) 124.15(4) 1_555 1_555 1_555 yes
C(6) C(5) C(4) 118.83(5) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 118.71(4) 1_555 1_555 1_555 yes
C(4) C(5) H(5) 122.46(3) 1_555 1_555 1_555 yes
N(3) C(4) C(5) 124.63(4) 1_555 1_555 1_555 yes
N(3) C(4) C(3) 116.56(4) 1_555 1_555 1_555 yes
C(5) C(4) C(3) 118.81(3) 1_555 1_555 1_555 yes
C(4) C(3) C(2) 119.31(4) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 120.03(3) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 120.64(4) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 123.84(5) 1_555 1_555 1_555 yes
O(1) C(7) N(3) 124.54(4) 1_555 1_555 1_555 yes
O(1) C(7) N(4) 124.29(5) 1_555 1_555 1_555 yes
N(3) C(7) N(4) 111.17(4) 1_555 1_555 1_555 yes
N(4) C(8) C(13) 124.89(3) 1_555 1_555 1_555 yes
N(4) C(8) C(9) 116.19(4) 1_555 1_555 1_555 yes
C(13) C(8) C(9) 118.92(4) 1_555 1_555 1_555 yes
C(8) C(13) C(12) 118.56(3) 1_555 1_555 1_555 yes
C(8) C(13) H(13) 121.75(4) 1_555 1_555 1_555 yes
C(12) C(13) H(13) 119.68(4) 1_555 1_555 1_555 yes
C(13) C(12) C(11) 124.33(4) 1_555 1_555 1_555 yes
C(12) C(11) C(10) 115.18(4) 1_555 1_555 1_555 yes
C(12) C(11) H(11) 122.75(5) 1_555 1_555 1_555 yes
C(10) C(11) H(11) 122.06(3) 1_555 1_555 1_555 yes
N(6) C(10) C(11) 118.15(4) 1_555 1_555 1_555 yes
N(6) C(10) C(9) 118.12(4) 1_555 1_555 1_555 yes
C(11) C(10) C(9) 123.73(3) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 119.25(4) 1_555 1_555 1_555 yes
C(8) C(9) H(9) 119.47(4) 1_555 1_555 1_555 yes
C(10) C(9) H(9) 121.28(3) 1_555 1_555 1_555 yes
H(14A) C(14) H(14B) 111.72(5) 1_555 1_555 1_555 yes
H(14A) C(14) H(14C) 109.79(6) 1_555 1_555 1_555 yes
H(14B) C(14) H(14C) 113.29(4) 1_555 1_555 1_555 yes
H(15A) C(15) H(15B) 107.93(10) 1_555 1_555 1_555 yes
H(15A) C(15) H(15C) 118.00(6) 1_555 1_555 1_555 yes
H(15B) C(15) H(15C) 109.67(10) 1_555 1_555 1_555 yes
H(16A) C(16) H(16B) 112.12(6) 1_555 1_555 1_555 yes
H(16A) C(16) H(16C) 113.02(5) 1_555 1_555 1_555 yes
H(16B) C(16) H(16C) 111.43(6) 1_555 1_555 1_555 yes
H(17A) C(17) H(17B) 113.74(6) 1_555 1_555 1_555 yes
H(17A) C(17) H(17C) 113.46(7) 1_555 1_555 1_555 yes
H(17B) C(17) H(17C) 109.89(8) 1_555 1_555 1_555 yes
O(10) C(18) O(11) 123.80(5) 1_555 1_555 1_555 yes
O(10) C(18) C(19) 119.05(5) 1_555 1_555 1_555 yes
O(11) C(18) C(19) 117.12(5) 1_555 1_555 1_555 yes
C(18) C(19) H(19A) 117.57(7) 1_555 1_555 1_555 yes
C(18) C(19) H(19B) 109.66(6) 1_555 1_555 1_555 yes
C(18) C(19) H(19C) 108.55(8) 1_555 1_555 1_555 yes
H(19A) C(19) H(19B) 101.19(9) 1_555 1_555 1_555 yes
H(19A) C(19) H(19C) 107.82(7) 1_555 1_555 1_555 yes
H(19B) C(19) H(19C) 111.95(7) 1_555 1_555 1_555 yes

_database_code_depnum_ccdc_archive 'CCDC 953245'
