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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hq-im0925_-100
_database_code_depnum_ccdc_archive 'CCDC 1033147'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H10 N4 O3'
_chemical_formula_moiety         'C12 H10 N4 O3'
_chemical_formula_weight         258.24
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.45290(10)
_cell_length_b                   16.1050(2)
_cell_length_c                   7.25488(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.369(1)
_cell_angle_gamma                90.0000
_cell_volume                     1129.42(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10580
_cell_measurement_theta_min      4.58
_cell_measurement_theta_max      68.21
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536.00
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            12584
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_theta_max         68.210
_diffrn_reflns_theta_min         4.574
_diffrn_reflns_theta_full        68.210
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2069
_reflns_number_gt                1747
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0927
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2069
_refine_ls_number_parameters     184
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0567P)²+0.2915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.27372(12) -0.12936(6) 0.64541(16) 0.0329(3) Uani 1 4 d . . .
O2 O 0.33348(12) -0.00938(7) 0.81244(16) 0.0326(3) Uani 1 4 d . . .
O3 O 0.39394(13) -0.08775(7) 0.34730(17) 0.0390(3) Uani 1 4 d . . .
N1 N 0.24688(14) 0.00349(8) 0.13117(19) 0.0280(3) Uani 1 4 d . . .
N2 N 0.15196(13) 0.05060(8) 0.42443(18) 0.0273(3) Uani 1 4 d . . .
N3 N 0.50830(15) 0.26836(9) 0.9235(2) 0.0335(3) Uani 1 4 d . . .
N4 N 0.39457(14) 0.15546(9) 0.8232(2) 0.0322(3) Uani 1 4 d . . .
C1 C 0.28891(15) -0.05307(9) 0.6553(2) 0.0265(3) Uani 1 4 d . . .
C2 C 0.24408(16) -0.00724(9) 0.4577(2) 0.0261(3) Uani 1 4 d . . .
C3 C 0.30167(16) -0.03534(9) 0.3112(2) 0.0283(3) Uani 1 4 d . . .
C4 C 0.14024(15) 0.06060(9) 0.0841(2) 0.0262(3) Uani 1 4 d . . .
C5 C 0.07821(17) 0.09365(9) -0.1087(2) 0.0304(4) Uani 1 4 d . . .
C6 C -0.02694(17) 0.15049(10) -0.1475(2) 0.0332(4) Uani 1 4 d . . .
C7 C -0.07242(17) 0.17586(10) 0.0019(3) 0.0337(4) Uani 1 4 d . . .
C8 C -0.01223(16) 0.14299(10) 0.1911(2) 0.0307(4) Uani 1 4 d . . .
C9 C 0.09508(15) 0.08495(9) 0.2343(2) 0.0263(3) Uani 1 4 d . . .
C10 C 0.38137(17) 0.29001(10) 0.7857(3) 0.0359(4) Uani 1 4 d . . .
C11 C 0.30979(17) 0.21942(11) 0.7227(3) 0.0366(4) Uani 1 4 d . . .
C12 C 0.51380(17) 0.18695(10) 0.9439(2) 0.0323(4) Uani 1 4 d . . .
H1 H 0.10849 0.07697 -0.21102 0.0365 Uiso 1 4 calc R . .
H2 H -0.06945 0.17292 -0.27782 0.0398 Uiso 1 4 calc R . .
H3 H -0.14456 0.21563 -0.02703 0.0405 Uiso 1 4 calc R . .
H4 H -0.04362 0.15974 0.29231 0.0369 Uiso 1 4 calc R . .
H5 H 0.34987 0.34468 0.74278 0.0431 Uiso 1 4 calc R . .
H6 H 0.21799 0.21461 0.62683 0.0439 Uiso 1 4 calc R . .
H7 H 0.59057 0.1561 1.03066 0.0388 Uiso 1 4 calc R . .
H8 H 0.276(2) -0.0117(12) 0.036(3) 0.039(5) Uiso 1 4 d . . .
H9 H 0.374(2) 0.0998(15) 0.812(3) 0.057(6) Uiso 1 4 d . . .
H10 H 0.575(2) 0.3041(14) 0.989(3) 0.059(7) Uiso 1 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C1 1.2374(17) yes . .
O2 C1 1.2682(18) yes . .
O3 C3 1.232(2) yes . .
N1 C3 1.3620(19) yes . .
N1 C4 1.384(2) yes . .
N2 C2 1.295(2) yes . .
N2 C9 1.3919(18) yes . .
N3 C10 1.3682(19) yes . .
N3 C12 1.318(2) yes . .
N4 C11 1.373(2) yes . .
N4 C12 1.3215(19) yes . .
C1 C2 1.519(2) yes . .
C2 C3 1.478(3) yes . .
C4 C5 1.403(2) yes . .
C4 C9 1.399(3) yes . .
C5 C6 1.375(2) yes . .
C6 C7 1.399(3) yes . .
C7 C8 1.380(2) yes . .
C8 C9 1.401(2) yes . .
C10 C11 1.342(2) yes . .
N1 H8 0.89(2) no . .
N3 H10 0.89(2) no . .
N4 H9 0.92(2) no . .
C5 H1 0.950 no . .
C6 H2 0.950 no . .
C7 H3 0.950 no . .
C8 H4 0.950 no . .
C10 H5 0.950 no . .
C11 H6 0.950 no . .
C12 H7 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C3 N1 C4 123.17(16) yes . . .
C2 N2 C9 118.53(15) yes . . .
C10 N3 C12 108.91(13) yes . . .
C11 N4 C12 108.61(14) yes . . .
O1 C1 O2 126.72(14) yes . . .
O1 C1 C2 116.19(13) yes . . .
O2 C1 C2 117.04(13) yes . . .
N2 C2 C1 117.78(16) yes . . .
N2 C2 C3 124.32(14) yes . . .
C1 C2 C3 117.78(13) yes . . .
O3 C3 N1 121.86(17) yes . . .
O3 C3 C2 123.83(14) yes . . .
N1 C3 C2 114.29(13) yes . . .
N1 C4 C5 121.42(16) yes . . .
N1 C4 C9 118.22(13) yes . . .
C5 C4 C9 120.35(14) yes . . .
C4 C5 C6 119.13(17) yes . . .
C5 C6 C7 121.11(15) yes . . .
C6 C7 C8 119.85(15) yes . . .
C7 C8 C9 120.10(17) yes . . .
N2 C9 C4 121.14(13) yes . . .
N2 C9 C8 119.38(16) yes . . .
C4 C9 C8 119.45(13) yes . . .
N3 C10 C11 107.04(14) yes . . .
N4 C11 C10 106.92(13) yes . . .
N3 C12 N4 108.52(13) yes . . .
C3 N1 H8 118.4(11) no . . .
C4 N1 H8 118.2(11) no . . .
C10 N3 H10 124.9(14) no . . .
C12 N3 H10 126.2(14) no . . .
C11 N4 H9 127.0(12) no . . .
C12 N4 H9 124.4(12) no . . .
C4 C5 H1 120.437 no . . .
C6 C5 H1 120.437 no . . .
C5 C6 H2 119.444 no . . .
C7 C6 H2 119.446 no . . .
C6 C7 H3 120.073 no . . .
C8 C7 H3 120.074 no . . .
C7 C8 H4 119.948 no . . .
C9 C8 H4 119.947 no . . .
N3 C10 H5 126.478 no . . .
C11 C10 H5 126.485 no . . .
N4 C11 H6 126.544 no . . .
C10 C11 H6 126.540 no . . .
N3 C12 H7 125.744 no . . .
N4 C12 H7 125.737 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 N1 C4 C5 -174.16(12) no . . . .
C3 N1 C4 C9 5.8(2) no . . . .
C4 N1 C3 O3 177.87(12) no . . . .
C4 N1 C3 C2 -3.91(19) no . . . .
C2 N2 C9 C4 -2.9(2) no . . . .
C2 N2 C9 C8 175.13(12) no . . . .
C9 N2 C2 C1 -170.87(11) no . . . .
C9 N2 C2 C3 4.9(2) no . . . .
C10 N3 C12 N4 0.1(2) no . . . .
C12 N3 C10 C11 -0.0(2) no . . . .
C11 N4 C12 N3 -0.2(2) no . . . .
C12 N4 C11 C10 0.2(2) no . . . .
O1 C1 C2 N2 122.62(15) no . . . .
O1 C1 C2 C3 -53.46(19) no . . . .
O2 C1 C2 N2 -55.11(19) no . . . .
O2 C1 C2 C3 128.82(14) no . . . .
N2 C2 C3 O3 176.51(13) no . . . .
N2 C2 C3 N1 -1.7(2) no . . . .
C1 C2 C3 O3 -7.7(2) no . . . .
C1 C2 C3 N1 174.12(11) no . . . .
N1 C4 C5 C6 -179.70(12) no . . . .
N1 C4 C9 N2 -2.3(2) no . . . .
N1 C4 C9 C8 179.68(11) no . . . .
C5 C4 C9 N2 177.65(12) no . . . .
C5 C4 C9 C8 -0.3(2) no . . . .
C9 C4 C5 C6 0.3(2) no . . . .
C4 C5 C6 C7 0.2(2) no . . . .
C5 C6 C7 C8 -0.6(2) no . . . .
C6 C7 C8 C9 0.6(2) no . . . .
C7 C8 C9 N2 -178.15(13) no . . . .
C7 C8 C9 C4 -0.1(2) no . . . .
N3 C10 C11 N4 -0.1(2) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 O3 2.962(2) no . .
O1 N2 3.3222(16) no . .
O1 C3 2.966(2) no . .
O2 N2 2.8969(15) no . .
O2 C3 3.548(2) no . .
O3 N2 3.571(2) no . .
O3 C1 2.894(2) no . .
O3 C4 3.5402(18) no . .
N1 N2 2.774(2) no . .
C2 C4 2.735(2) no . .
C2 C8 3.582(2) no . .
C3 C9 2.795(2) no . .
C4 C7 2.781(2) no . .
C5 C8 2.797(3) no . .
C6 C9 2.779(2) no . .
O1 N3 3.004(2) no . 2_646
O1 C6 3.5676(17) no . 3_555
O1 C8 3.375(2) no . 3_556
O1 C12 3.1039(17) no . 3_657
O2 O2 3.5221(14) no . 3_657
O2 N1 2.793(2) no . 1_556
O2 N4 2.7246(18) no . .
O2 C4 3.502(2) no . 1_556
O2 C5 3.371(2) no . 1_556
O2 C12 3.4211(19) no . 3_657
O3 N3 2.8080(18) no . 2_646
O3 N4 3.113(2) no . 3_656
O3 C10 3.4235(18) no . 2_646
O3 C12 3.081(2) no . 3_656
N1 O2 2.793(2) no . 1_554
N1 C6 3.414(2) no . 3_555
N1 C7 3.356(2) no . 3_555
N1 C8 3.5614(19) no . 3_555
N2 N4 3.4741(17) no . .
N2 C5 3.4983(18) no . 3_555
N2 C11 3.475(2) no . .
N3 O1 3.004(2) no . 2_656
N3 O3 2.8080(18) no . 2_656
N3 C10 3.493(3) no . 4_555
N3 C11 3.533(3) no . 4_555
N3 C12 3.575(2) no . 4_554
N4 O2 2.7246(18) no . .
N4 O3 3.113(2) no . 3_656
N4 N2 3.4741(17) no . .
N4 C1 3.600(2) no . .
N4 C10 3.522(2) no . 4_555
C1 N4 3.600(2) no . .
C1 C12 3.577(2) no . 3_657
C2 C6 3.413(2) no . 3_555
C3 C6 3.240(2) no . 3_555
C3 C7 3.447(2) no . 3_555
C4 O2 3.502(2) no . 1_554
C4 C4 3.342(2) no . 3_555
C4 C5 3.425(2) no . 3_555
C4 C9 3.5436(19) no . 3_555
C4 C10 3.387(2) no . 4_554
C5 O2 3.371(2) no . 1_554
C5 N2 3.4983(18) no . 3_555
C5 C4 3.425(2) no . 3_555
C5 C9 3.336(2) no . 3_555
C6 O1 3.5676(17) no . 3_555
C6 N1 3.414(2) no . 3_555
C6 C2 3.413(2) no . 3_555
C6 C3 3.240(2) no . 3_555
C6 C8 3.549(2) no . 4_554
C7 N1 3.356(2) no . 3_555
C7 C3 3.447(2) no . 3_555
C8 O1 3.375(2) no . 3_556
C8 N1 3.5614(19) no . 3_555
C8 C6 3.549(2) no . 4_555
C9 C4 3.5436(19) no . 3_555
C9 C5 3.336(2) no . 3_555
C9 C10 3.507(2) no . 4_554
C10 O3 3.4235(18) no . 2_656
C10 N3 3.493(3) no . 4_554
C10 N4 3.522(2) no . 4_554
C10 C4 3.387(2) no . 4_555
C10 C9 3.507(2) no . 4_555
C10 C11 3.527(3) no . 4_555
C10 C12 3.289(3) no . 4_554
C11 N2 3.475(2) no . .
C11 N3 3.533(3) no . 4_554
C11 C10 3.527(3) no . 4_554
C12 O1 3.1039(17) no . 3_657
C12 O2 3.4211(19) no . 3_657
C12 O3 3.081(2) no . 3_656
C12 N3 3.575(2) no . 4_555
C12 C1 3.577(2) no . 3_657
C12 C10 3.289(3) no . 4_555
O3 H8 2.449(18) no . .
N1 H1 2.6311 no . .
N2 H4 2.5877 no . .
N3 H6 3.1016 no . .
N3 H9 3.02(2) no . .
N4 H5 3.1045 no . .
N4 H10 3.00(2) no . .
C2 H8 3.20(2) no . .
C4 H2 3.2542 no . .
C4 H4 3.2764 no . .
C5 H3 3.2684 no . .
C5 H8 2.569(18) no . .
C6 H4 3.2642 no . .
C7 H1 3.2742 no . .
C8 H2 3.2583 no . .
C9 H1 3.2894 no . .
C9 H3 3.2687 no . .
C9 H8 3.18(2) no . .
C10 H7 3.1037 no . .
C10 H9 3.07(2) no . .
C11 H7 3.1072 no . .
C11 H10 3.04(2) no . .
C12 H5 3.1008 no . .
C12 H6 3.1043 no . .
H1 H2 2.3230 no . .
H1 H8 2.4350 no . .
H2 H3 2.3425 no . .
H3 H4 2.3303 no . .
H5 H6 2.4725 no . .
H5 H10 2.4431 no . .
H6 H9 2.4922 no . .
H7 H9 2.3947 no . .
H7 H10 2.4010 no . .
O1 H2 2.7981 no . 3_555
O1 H3 2.8125 no . 2_545
O1 H4 2.6563 no . 3_556
O1 H7 2.2767 no . 3_657
O1 H8 3.40(2) no . 1_556
O1 H10 2.40(3) no . 2_646
O2 H1 2.6813 no . 1_556
O2 H7 2.6118 no . 3_657
O2 H8 1.93(2) no . 1_556
O2 H9 1.81(2) no . .
O2 H9 3.54(2) no . 3_657
O3 H2 3.5127 no . 3_555
O3 H3 3.4388 no . 3_555
O3 H5 3.3374 no . 2_646
O3 H7 3.0157 no . 3_656
O3 H9 3.07(3) no . 3_656
O3 H10 2.06(2) no . 2_646
N1 H5 2.6703 no . 4_554
N1 H7 3.5199 no . 3_656
N1 H9 3.44(3) no . 1_554
N2 H1 2.8803 no . 1_556
N2 H1 3.2896 no . 3_555
N2 H5 3.3069 no . 4_554
N2 H6 2.9729 no . .
N2 H9 2.993(19) no . .
N3 H7 3.4943 no . 4_554
N4 H1 3.1680 no . 1_556
N4 H5 3.2505 no . 4_555
N4 H8 3.55(2) no . 1_556
C1 H1 3.2057 no . 1_556
C1 H2 3.4212 no . 3_555
C1 H4 3.2268 no . 3_556
C1 H7 2.7107 no . 3_657
C1 H8 2.90(2) no . 1_556
C1 H9 2.72(2) no . .
C1 H10 3.09(3) no . 2_646
C2 H1 3.4952 no . 1_556
C2 H2 3.2159 no . 3_555
C2 H5 3.4381 no . 4_554
C2 H9 2.96(2) no . .
C2 H10 3.52(2) no . 2_646
C3 H2 3.2269 no . 3_555
C3 H3 3.5778 no . 3_555
C3 H5 3.1810 no . 4_554
C3 H10 3.00(2) no . 2_646
C4 H5 2.5562 no . 4_554
C5 H5 3.1687 no . 4_554
C5 H6 3.4272 no . 1_554
C5 H6 3.5622 no . 4_554
C5 H9 3.35(3) no . 1_554
C6 H3 3.3417 no . 4_554
C6 H4 3.0829 no . 4_554
C6 H6 3.3700 no . 4_554
C7 H2 2.9068 no . 4_555
C7 H4 3.1241 no . 4_554
C7 H6 3.3247 no . 4_554
C7 H8 3.34(2) no . 3_555
C8 H2 3.0497 no . 4_555
C8 H6 3.3650 no . .
C8 H6 3.4818 no . 4_554
C8 H8 3.366(18) no . 3_555
C9 H1 3.3291 no . 3_555
C9 H5 2.8735 no . 4_554
C9 H6 3.3667 no . .
C10 H6 3.5018 no . 4_555
C10 H7 3.4698 no . 4_554
C11 H1 3.2699 no . 1_556
C11 H6 3.5760 no . 4_555
C12 H3 3.5266 no . 1_656
C12 H5 3.2751 no . 4_555
C12 H8 3.55(2) no . 3_656
C12 H10 3.60(3) no . 4_554
H1 O2 2.6813 no . 1_554
H1 N2 2.8803 no . 1_554
H1 N2 3.2896 no . 3_555
H1 N4 3.1680 no . 1_554
H1 C1 3.2057 no . 1_554
H1 C2 3.4952 no . 1_554
H1 C9 3.3291 no . 3_555
H1 C11 3.2699 no . 1_554
H1 H4 3.5955 no . 1_554
H1 H5 3.5320 no . 4_554
H1 H6 2.9381 no . 1_554
H1 H9 2.7376 no . 1_554
H2 O1 2.7981 no . 3_555
H2 O3 3.5127 no . 3_555
H2 C1 3.4212 no . 3_555
H2 C2 3.2159 no . 3_555
H2 C3 3.2269 no . 3_555
H2 C7 2.9068 no . 4_554
H2 C8 3.0497 no . 4_554
H2 H3 2.4549 no . 4_554
H2 H4 3.2380 no . 1_554
H2 H4 2.7368 no . 4_554
H2 H6 3.3969 no . 1_554
H2 H10 3.4646 no . 4_453
H3 O1 2.8125 no . 2_555
H3 O3 3.4388 no . 3_555
H3 C3 3.5778 no . 3_555
H3 C6 3.3417 no . 4_555
H3 C12 3.5266 no . 1_454
H3 H2 2.4549 no . 4_555
H3 H4 2.8129 no . 4_554
H3 H7 3.1051 no . 1_454
H3 H8 3.5512 no . 3_555
H3 H10 3.2986 no . 1_454
H4 O1 2.6563 no . 3_556
H4 C1 3.2268 no . 3_556
H4 C6 3.0829 no . 4_555
H4 C7 3.1241 no . 4_555
H4 H1 3.5955 no . 1_556
H4 H2 3.2380 no . 1_556
H4 H2 2.7368 no . 4_555
H4 H3 2.8129 no . 4_555
H4 H6 3.0162 no . .
H4 H7 3.5642 no . 1_454
H4 H8 3.5858 no . 3_555
H5 O3 3.3374 no . 2_656
H5 N1 2.6703 no . 4_555
H5 N2 3.3069 no . 4_555
H5 N4 3.2505 no . 4_554
H5 C2 3.4381 no . 4_555
H5 C3 3.1810 no . 4_555
H5 C4 2.5562 no . 4_555
H5 C5 3.1687 no . 4_555
H5 C9 2.8735 no . 4_555
H5 C12 3.2751 no . 4_554
H5 H1 3.5320 no . 4_555
H5 H7 3.4126 no . 4_554
H5 H8 3.0325 no . 4_555
H5 H9 3.3476 no . 4_554
H6 N2 2.9729 no . .
H6 C5 3.4272 no . 1_556
H6 C5 3.5622 no . 4_555
H6 C6 3.3700 no . 4_555
H6 C7 3.3247 no . 4_555
H6 C8 3.3650 no . .
H6 C8 3.4818 no . 4_555
H6 C9 3.3667 no . .
H6 C10 3.5018 no . 4_554
H6 C11 3.5760 no . 4_554
H6 H1 2.9381 no . 1_556
H6 H2 3.3969 no . 1_556
H6 H4 3.0162 no . .
H7 O1 2.2767 no . 3_657
H7 O2 2.6118 no . 3_657
H7 O3 3.0157 no . 3_656
H7 N1 3.5199 no . 3_656
H7 N3 3.4943 no . 4_555
H7 C1 2.7107 no . 3_657
H7 C10 3.4698 no . 4_555
H7 H3 3.1051 no . 1_656
H7 H4 3.5642 no . 1_656
H7 H5 3.4126 no . 4_555
H7 H8 2.8469 no . 3_656
H7 H10 3.4500 no . 4_555
H8 O1 3.40(2) no . 1_554
H8 O2 1.93(2) no . 1_554
H8 N4 3.55(2) no . 1_554
H8 C1 2.90(2) no . 1_554
H8 C7 3.34(2) no . 3_555
H8 C8 3.366(18) no . 3_555
H8 C12 3.55(2) no . 3_656
H8 H3 3.5512 no . 3_555
H8 H4 3.5858 no . 3_555
H8 H5 3.0325 no . 4_554
H8 H7 2.8469 no . 3_656
H8 H9 2.86(3) no . 1_554
H9 O2 1.81(2) no . .
H9 O2 3.54(2) no . 3_657
H9 O3 3.07(3) no . 3_656
H9 N1 3.44(3) no . 1_556
H9 N2 2.993(19) no . .
H9 C1 2.72(2) no . .
H9 C2 2.96(2) no . .
H9 C5 3.35(3) no . 1_556
H9 H1 2.7376 no . 1_556
H9 H5 3.3476 no . 4_555
H9 H8 2.86(3) no . 1_556
H10 O1 2.40(3) no . 2_656
H10 O3 2.06(2) no . 2_656
H10 C1 3.09(3) no . 2_656
H10 C2 3.52(2) no . 2_656
H10 C3 3.00(2) no . 2_656
H10 C12 3.60(3) no . 4_555
H10 H2 3.4646 no . 4_656
H10 H3 3.2986 no . 1_656
H10 H7 3.4500 no . 4_554

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H8 O2 . . 1_554 2.793(2) 0.89(2) 1.93(2) 162.7(17) no
N3 H10 O1 . . 2_656 3.004(2) 0.89(2) 2.40(3) 125(2) no
N3 H10 O3 . . 2_656 2.8080(18) 0.89(2) 2.06(2) 140(2) no
N4 H9 O2 . . . 2.7246(18) 0.92(2) 1.81(2) 175(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_P61_orange_lowT
_database_code_depnum_ccdc_archive 'CCDC 1033148'
_audit_update_record             
;
2014-11-07 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H12 N4 O4'
_chemical_formula_moiety         'C12 H12 N4 O4'
_chemical_formula_weight         276.25
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.02478(13)
_cell_length_b                   16.0194(3)
_cell_length_c                   21.5034(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2419.85(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16038
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152.00
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_T_max  0.906

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            25159
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_min         4.112
_diffrn_reflns_theta_full        68.220
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2221
_reflns_number_gt                1996
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1138
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2221
_refine_ls_number_parameters     201
_refine_ls_goodness_of_fit_ref   0.815
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0849P)²+3.0547P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2388(2) 0.14877(8) 0.32351(5) 0.0270(3) Uani 1 8 d . . .
O2 O 0.42409(18) 0.24467(8) 0.36868(5) 0.0242(3) Uani 1 8 d . . .
O3 O 0.10360(19) 0.28221(7) 0.46399(6) 0.0244(3) Uani 1 8 d . . .
O4 O 0.2489(2) 0.27816(9) 0.70840(6) 0.0301(3) Uani 1 8 d . . .
N1 N 0.1053(2) 0.17536(9) 0.53307(6) 0.0176(3) Uani 1 8 d . . .
N2 N 0.28156(19) 0.07509(8) 0.44514(6) 0.0162(3) Uani 1 8 d . . .
N3 N 0.5634(2) 0.02614(9) 0.65355(7) 0.0195(3) Uani 1 8 d . . .
N4 N 0.4376(2) 0.13434(10) 0.69665(7) 0.0228(3) Uani 1 8 d . . .
C1 C 0.3061(2) 0.18568(10) 0.36938(8) 0.0181(4) Uani 1 8 d . . .
C2 C 0.2465(2) 0.15300(10) 0.43320(7) 0.0168(4) Uani 1 8 d . . .
C3 C 0.1487(2) 0.20997(10) 0.47713(7) 0.0181(4) Uani 1 8 d . . .
C4 C 0.1420(2) 0.09299(10) 0.54762(7) 0.0166(3) Uani 1 8 d . . .
C5 C 0.0874(2) 0.05931(11) 0.60506(8) 0.0186(4) Uani 1 8 d . . .
C6 C 0.1211(3) -0.02410(11) 0.61712(8) 0.0200(4) Uani 1 8 d . . .
C7 C 0.2121(2) -0.07460(10) 0.57302(8) 0.0194(4) Uani 1 8 d . . .
C8 C 0.2670(2) -0.04150(10) 0.51664(8) 0.0181(4) Uani 1 8 d . . .
C9 C 0.2317(2) 0.04276(10) 0.50293(8) 0.0168(4) Uani 1 8 d . . .
C10 C 0.4873(3) -0.00009(12) 0.70922(8) 0.0233(4) Uani 1 8 d . . .
C11 C 0.4087(3) 0.06798(12) 0.73598(8) 0.0245(4) Uani 1 8 d . . .
C12 C 0.5298(3) 0.10741(11) 0.64693(8) 0.0201(4) Uani 1 8 d . . .
H1 H 0.042(3) 0.2069(14) 0.5621(10) 0.031(6) Uiso 1 8 d . . .
H2 H 0.137(4) 0.2724(17) 0.6908(14) 0.054(8) Uiso 1 8 d . . .
H3 H 0.241(4) 0.3020(16) 0.7456(15) 0.051(7) Uiso 1 8 d . . .
H4 H 0.617(3) -0.0069(14) 0.6244(11) 0.030(6) Uiso 1 8 d . . .
H5 H 0.02779 0.09352 0.63543 0.0224 Uiso 1 8 calc R . .
H6 H 0.08218 -0.04743 0.65569 0.0240 Uiso 1 8 calc R . .
H7 H 0.23606 -0.13172 0.58198 0.0233 Uiso 1 8 calc R . .
H8 H 0.32896 -0.0759 0.48689 0.0217 Uiso 1 8 calc R . .
H9 H 0.391(4) 0.1865(17) 0.7005(12) 0.042(7) Uiso 1 8 d . . .
H10 H 0.48964 -0.05517 0.72558 0.0279 Uiso 1 8 calc R . .
H11 H 0.34499 0.06965 0.77493 0.0294 Uiso 1 8 calc R . .
H12 H 0.56609 0.14055 0.61227 0.0241 Uiso 1 8 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O1 C1 1.244(2) yes . .
O2 C1 1.257(2) yes . .
O3 C3 1.233(2) yes . .
N1 C3 1.359(2) yes . .
N1 C4 1.380(2) yes . .
N2 C2 1.298(2) yes . .
N2 C9 1.391(2) yes . .
N3 C10 1.377(2) yes . .
N3 C12 1.331(2) yes . .
N4 C11 1.374(2) yes . .
N4 C12 1.322(2) yes . .
C1 C2 1.527(2) yes . .
C2 C3 1.482(2) yes . .
C4 C5 1.401(2) yes . .
C4 C9 1.403(2) yes . .
C5 C6 1.382(2) yes . .
C6 C7 1.401(2) yes . .
C7 C8 1.378(2) yes . .
C8 C9 1.404(2) yes . .
C10 C11 1.351(3) yes . .
O4 H2 0.88(3) no . .
O4 H3 0.89(3) no . .
N1 H1 0.92(2) no . .
N3 H4 0.90(2) no . .
N4 H9 0.90(3) no . .
C5 H5 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C3 N1 C4 123.27(14) yes . . .
C2 N2 C9 119.14(13) yes . . .
C10 N3 C12 108.84(15) yes . . .
C11 N4 C12 108.53(15) yes . . .
O1 C1 O2 126.78(16) yes . . .
O1 C1 C2 116.44(14) yes . . .
O2 C1 C2 116.71(14) yes . . .
N2 C2 C1 117.08(14) yes . . .
N2 C2 C3 123.65(14) yes . . .
C1 C2 C3 119.26(14) yes . . .
O3 C3 N1 121.90(15) yes . . .
O3 C3 C2 123.43(14) yes . . .
N1 C3 C2 114.63(14) yes . . .
N1 C4 C5 121.10(14) yes . . .
N1 C4 C9 118.49(14) yes . . .
C5 C4 C9 120.39(15) yes . . .
C4 C5 C6 119.40(16) yes . . .
C5 C6 C7 120.64(16) yes . . .
C6 C7 C8 120.06(15) yes . . .
C7 C8 C9 120.36(15) yes . . .
N2 C9 C4 120.76(14) yes . . .
N2 C9 C8 120.08(15) yes . . .
C4 C9 C8 119.14(15) yes . . .
N3 C10 C11 106.42(16) yes . . .
N4 C11 C10 107.58(15) yes . . .
N3 C12 N4 108.63(15) yes . . .
H2 O4 H3 112(3) no . . .
C3 N1 H1 119.1(14) no . . .
C4 N1 H1 117.5(14) no . . .
C10 N3 H4 125.9(15) no . . .
C12 N3 H4 125.0(15) no . . .
C11 N4 H9 127.4(16) no . . .
C12 N4 H9 123.7(16) no . . .
C4 C5 H5 120.302 no . . .
C6 C5 H5 120.296 no . . .
C5 C6 H6 119.677 no . . .
C7 C6 H6 119.685 no . . .
C6 C7 H7 119.976 no . . .
C8 C7 H7 119.967 no . . .
C7 C8 H8 119.822 no . . .
C9 C8 H8 119.818 no . . .
N3 C10 H10 126.784 no . . .
C11 C10 H10 126.795 no . . .
N4 C11 H11 126.208 no . . .
C10 C11 H11 126.215 no . . .
N3 C12 H12 125.682 no . . .
N4 C12 H12 125.691 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 N1 C4 C5 -177.32(13) no . . . .
C3 N1 C4 C9 1.2(2) no . . . .
C4 N1 C3 O3 175.40(14) no . . . .
C4 N1 C3 C2 -2.3(2) no . . . .
C2 N2 C9 C4 0.9(2) no . . . .
C2 N2 C9 C8 179.48(13) no . . . .
C9 N2 C2 C1 179.28(12) no . . . .
C9 N2 C2 C3 -2.3(2) no . . . .
C10 N3 C12 N4 0.87(19) no . . . .
C12 N3 C10 C11 -0.51(18) no . . . .
C11 N4 C12 N3 -0.89(19) no . . . .
C12 N4 C11 C10 0.56(19) no . . . .
O1 C1 C2 N2 57.3(2) no . . . .
O1 C1 C2 C3 -121.17(15) no . . . .
O2 C1 C2 N2 -119.83(16) no . . . .
O2 C1 C2 C3 61.71(19) no . . . .
N2 C2 C3 O3 -174.70(14) no . . . .
N2 C2 C3 N1 3.0(2) no . . . .
C1 C2 C3 O3 3.7(2) no . . . .
C1 C2 C3 N1 -178.65(13) no . . . .
N1 C4 C5 C6 177.89(13) no . . . .
N1 C4 C9 N2 -0.3(2) no . . . .
N1 C4 C9 C8 -178.88(13) no . . . .
C5 C4 C9 N2 178.19(14) no . . . .
C5 C4 C9 C8 -0.4(2) no . . . .
C9 C4 C5 C6 -0.6(2) no . . . .
C4 C5 C6 C7 1.2(2) no . . . .
C5 C6 C7 C8 -0.8(2) no . . . .
C6 C7 C8 C9 -0.2(2) no . . . .
C7 C8 C9 N2 -177.82(14) no . . . .
C7 C8 C9 C4 0.7(2) no . . . .
N3 C10 C11 N4 -0.03(19) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O1 N2 2.8851(17) no . .
O1 C3 3.5035(19) no . .
O2 O3 3.1033(18) no . .
O2 N2 3.3295(18) no . .
O2 C3 3.081(2) no . .
O3 N2 3.5687(17) no . .
O3 C1 2.925(2) no . .
O3 C4 3.535(2) no . .
N1 N2 2.7728(19) no . .
C2 C4 2.742(2) no . .
C2 C8 3.598(2) no . .
C3 C9 2.797(2) no . .
C4 C7 2.784(2) no . .
C5 C8 2.795(2) no . .
C6 C9 2.789(2) no . .
O1 O4 2.7390(17) no . 3_554
O1 N3 3.1663(19) no . 5_656
O1 C6 3.466(2) no . 5_556
O1 C10 3.142(2) no . 5_656
O2 O4 2.8438(19) no . 6_556
O2 N1 2.7794(18) no . 6_556
O2 C4 3.514(2) no . 6_556
O2 C5 3.391(2) no . 6_556
O3 N1 3.5665(19) no . 6_456
O3 N1 3.5898(19) no . 6_556
O3 C2 3.501(2) no . 6_456
O3 C3 3.440(2) no . 6_456
O3 C7 3.526(2) no . 2_555
O3 C8 3.176(2) no . 2_555
O3 C12 3.014(2) no . 6_456
O4 O1 2.7390(17) no . 3_555
O4 O2 2.8438(19) no . 6_456
O4 N4 2.670(2) no . .
O4 C1 3.533(2) no . 3_555
O4 C1 3.579(2) no . 6_456
O4 C11 3.598(2) no . .
N1 O2 2.7794(18) no . 6_456
N1 O3 3.5898(19) no . 6_456
N1 O3 3.5665(19) no . 6_556
N1 C7 3.575(2) no . 5_556
N1 C8 3.547(2) no . 5_556
N2 N3 2.884(2) no . 5_656
N2 C5 3.538(2) no . 5_556
N2 C6 3.234(2) no . 5_556
N2 C7 3.490(2) no . 5_556
N2 C7 3.578(2) no . 5_656
N2 C8 3.320(2) no . 5_656
N3 O1 3.1663(19) no . 5_656
N3 N2 2.884(2) no . 5_656
N3 C1 3.549(2) no . 5_656
N3 C5 3.542(2) no . .
N3 C6 3.304(2) no . .
N3 C7 3.419(2) no . .
N3 C11 3.461(2) no . 8_556
N4 O4 2.670(2) no . .
N4 C5 3.373(2) no . .
C1 O4 3.533(2) no . 3_554
C1 O4 3.579(2) no . 6_556
C1 N3 3.549(2) no . 5_656
C2 O3 3.501(2) no . 6_556
C2 C6 3.479(2) no . 5_556
C2 C7 3.460(2) no . 5_556
C3 O3 3.440(2) no . 6_556
C3 C7 3.506(2) no . 5_556
C4 O2 3.514(2) no . 6_456
C4 C8 3.293(2) no . 5_556
C4 C9 3.578(2) no . 5_556
C4 C12 3.469(2) no . .
C5 O2 3.391(2) no . 6_456
C5 N2 3.538(2) no . 5_556
C5 N3 3.542(2) no . .
C5 N4 3.373(2) no . .
C5 C12 3.326(2) no . .
C6 O1 3.466(2) no . 5_556
C6 N2 3.234(2) no . 5_556
C6 N3 3.304(2) no . .
C6 C2 3.479(2) no . 5_556
C6 C9 3.591(2) no . 5_556
C6 C10 3.269(2) no . .
C6 C11 3.576(2) no . .
C7 O3 3.526(2) no . 2_545
C7 N1 3.575(2) no . 5_556
C7 N2 3.490(2) no . 5_556
C7 N2 3.578(2) no . 5_656
C7 N3 3.419(2) no . .
C7 C2 3.460(2) no . 5_556
C7 C3 3.506(2) no . 5_556
C7 C9 3.556(2) no . 5_556
C8 O3 3.176(2) no . 2_545
C8 N1 3.547(2) no . 5_556
C8 N2 3.320(2) no . 5_656
C8 C4 3.293(2) no . 5_556
C8 C9 3.528(2) no . 5_556
C8 C9 3.547(2) no . 5_656
C9 C4 3.578(2) no . 5_556
C9 C6 3.591(2) no . 5_556
C9 C7 3.556(2) no . 5_556
C9 C8 3.528(2) no . 5_556
C9 C8 3.547(2) no . 5_656
C9 C9 3.534(2) no . 5_556
C10 O1 3.142(2) no . 5_656
C10 C6 3.269(2) no . .
C10 C11 3.367(3) no . 8_556
C11 O4 3.598(2) no . .
C11 N3 3.461(2) no . 8_456
C11 C6 3.576(2) no . .
C11 C10 3.367(3) no . 8_456
C11 C11 3.564(2) no . 8_456
C11 C11 3.564(2) no . 8_556
C12 O3 3.014(2) no . 6_556
C12 C4 3.469(2) no . .
C12 C5 3.326(2) no . .
O3 H1 2.47(2) no . .
N1 H5 2.6192 no . .
N2 H8 2.6014 no . .
N3 H9 3.01(3) no . .
N3 H11 3.1067 no . .
N4 H4 3.02(2) no . .
N4 H10 3.1204 no . .
C2 H1 3.24(2) no . .
C4 H6 3.2615 no . .
C4 H8 3.2786 no . .
C5 H1 2.56(2) no . .
C5 H7 3.2713 no . .
C6 H8 3.2654 no . .
C7 H5 3.2758 no . .
C8 H6 3.2610 no . .
C9 H1 3.21(2) no . .
C9 H5 3.2911 no . .
C9 H7 3.2715 no . .
C10 H9 3.07(3) no . .
C10 H12 3.1190 no . .
C11 H4 3.06(2) no . .
C11 H12 3.1066 no . .
C12 H10 3.1182 no . .
C12 H11 3.1029 no . .
H1 H5 2.4069 no . .
H4 H10 2.4755 no . .
H4 H12 2.4038 no . .
H5 H6 2.3311 no . .
H6 H7 2.3461 no . .
H7 H8 2.3252 no . .
H9 H11 2.4840 no . .
H9 H12 2.3785 no . .
H10 H11 2.4813 no . .
O1 H2 3.20(3) no . 3_554
O1 H2 3.08(3) no . 6_556
O1 H3 1.85(3) no . 3_554
O1 H4 2.73(2) no . 5_656
O1 H6 2.8143 no . 5_556
O1 H10 3.0427 no . 4_554
O1 H10 2.6460 no . 5_656
O2 H1 1.87(2) no . 6_556
O2 H2 1.99(3) no . 6_556
O2 H3 3.04(3) no . 3_554
O2 H3 3.40(3) no . 6_556
O2 H5 2.6940 no . 6_556
O2 H7 3.1779 no . 5_656
O2 H12 3.1422 no . 6_456
O3 H1 3.14(2) no . 6_556
O3 H7 3.0995 no . 2_555
O3 H7 3.5330 no . 5_556
O3 H8 2.3735 no . 2_555
O3 H12 2.0711 no . 6_456
O4 H2 3.48(3) no . 8_556
O4 H6 3.2402 no . 2_555
O4 H7 3.0798 no . 2_555
O4 H9 1.78(3) no . .
O4 H9 3.51(3) no . 8_456
O4 H10 3.1738 no . 2_555
O4 H10 3.5381 no . 7_656
N1 H7 3.4495 no . 2_555
N1 H7 3.5156 no . 5_556
N1 H8 3.4682 no . 5_556
N2 H4 1.98(2) no . 5_656
N2 H6 3.3803 no . 5_556
N2 H7 3.5561 no . 5_656
N2 H8 3.1020 no . 5_656
N3 H5 3.4584 no . 1_655
N3 H6 3.5801 no . .
N3 H8 3.2136 no . 5_656
N3 H11 2.6009 no . 8_556
N4 H2 3.06(3) no . .
N4 H2 3.56(3) no . 8_556
N4 H3 3.20(3) no . .
N4 H5 3.2324 no . .
N4 H11 3.1044 no . 8_556
C1 H1 2.81(2) no . 6_556
C1 H2 2.74(3) no . 6_556
C1 H3 2.71(3) no . 3_554
C1 H4 2.92(2) no . 5_656
C1 H6 3.5549 no . 5_556
C1 H7 3.4904 no . 5_656
C1 H10 3.2555 no . 5_656
C1 H12 3.2785 no . 6_456
C2 H1 3.06(2) no . 6_556
C2 H4 2.82(2) no . 5_656
C2 H6 3.4414 no . 5_556
C2 H7 3.4223 no . 5_556
C3 H1 3.18(2) no . 6_556
C3 H7 3.4887 no . 2_555
C3 H7 3.2389 no . 5_556
C3 H8 3.4403 no . 2_555
C3 H12 3.1251 no . 6_456
C4 H8 3.4019 no . 5_556
C4 H12 3.3744 no . .
C5 H4 3.50(2) no . 1_455
C5 H8 3.5406 no . 5_556
C5 H9 3.59(3) no . .
C5 H11 3.0964 no . 8_456
C6 H4 3.56(2) no . 1_455
C6 H4 3.50(2) no . .
C6 H10 3.5198 no . .
C6 H10 3.5415 no . 8_456
C6 H11 3.3773 no . 8_456
C7 H4 3.24(2) no . .
C8 H4 3.42(2) no . .
C8 H4 3.24(2) no . 5_656
C8 H8 3.4059 no . 5_656
C8 H12 3.4025 no . 5_656
C9 H4 2.99(2) no . 5_656
C9 H8 3.1392 no . 5_656
C10 H6 3.1622 no . .
C10 H6 3.0753 no . 8_556
C10 H11 2.7708 no . 8_556
C11 H5 3.4644 no . .
C11 H5 2.9178 no . 8_556
C11 H6 3.4146 no . .
C11 H6 3.2140 no . 8_556
C11 H11 3.0740 no . 8_556
C12 H5 3.5424 no . .
C12 H5 3.5138 no . 1_655
C12 H8 3.0853 no . 5_656
C12 H11 2.8444 no . 8_556
H1 O2 1.87(2) no . 6_456
H1 O3 3.14(2) no . 6_456
H1 C1 2.81(2) no . 6_456
H1 C2 3.06(2) no . 6_456
H1 C3 3.18(2) no . 6_456
H1 H2 3.03(4) no . .
H1 H7 3.0479 no . 2_555
H1 H8 3.5096 no . 5_556
H2 O1 3.20(3) no . 3_555
H2 O1 3.08(3) no . 6_456
H2 O2 1.99(3) no . 6_456
H2 O4 3.48(3) no . 8_456
H2 N4 3.06(3) no . .
H2 N4 3.56(3) no . 8_456
H2 C1 2.74(3) no . 6_456
H2 H1 3.03(4) no . .
H2 H3 3.13(4) no . 8_456
H2 H5 3.1961 no . .
H2 H6 3.5776 no . 2_555
H2 H7 2.9381 no . 2_555
H2 H9 2.26(4) no . .
H2 H9 3.21(4) no . 8_456
H2 H10 2.9961 no . 2_555
H3 O1 1.85(3) no . 3_555
H3 O2 3.04(3) no . 3_555
H3 O2 3.40(3) no . 6_456
H3 N4 3.20(3) no . .
H3 C1 2.71(3) no . 3_555
H3 H2 3.13(4) no . 8_556
H3 H3 3.52(4) no . 8_456
H3 H3 3.52(4) no . 8_556
H3 H6 3.3319 no . 2_555
H3 H9 2.34(4) no . .
H3 H9 3.29(4) no . 8_456
H3 H10 2.8363 no . 2_555
H3 H10 3.0335 no . 7_656
H4 O1 2.73(2) no . 5_656
H4 N2 1.98(2) no . 5_656
H4 C1 2.92(2) no . 5_656
H4 C2 2.82(2) no . 5_656
H4 C5 3.50(2) no . 1_655
H4 C6 3.50(2) no . .
H4 C6 3.56(2) no . 1_655
H4 C7 3.24(2) no . .
H4 C8 3.42(2) no . .
H4 C8 3.24(2) no . 5_656
H4 C9 2.99(2) no . 5_656
H4 H5 3.3124 no . 1_655
H4 H6 3.3985 no . 1_655
H4 H7 3.4629 no . .
H4 H8 2.7633 no . 5_656
H4 H11 2.9584 no . 8_556
H5 O2 2.6940 no . 6_456
H5 N3 3.4584 no . 1_455
H5 N4 3.2324 no . .
H5 C11 3.4644 no . .
H5 C11 2.9178 no . 8_456
H5 C12 3.5138 no . 1_455
H5 C12 3.5424 no . .
H5 H2 3.1961 no . .
H5 H4 3.3124 no . 1_455
H5 H9 3.2697 no . .
H5 H11 2.3475 no . 8_456
H5 H12 3.3667 no . 1_455
H6 O1 2.8143 no . 5_556
H6 O4 3.2402 no . 2_545
H6 N2 3.3803 no . 5_556
H6 N3 3.5801 no . .
H6 C1 3.5549 no . 5_556
H6 C2 3.4414 no . 5_556
H6 C10 3.1622 no . .
H6 C10 3.0753 no . 8_456
H6 C11 3.4146 no . .
H6 C11 3.2140 no . 8_456
H6 H2 3.5776 no . 2_545
H6 H3 3.3319 no . 2_545
H6 H4 3.3985 no . 1_455
H6 H10 3.2353 no . .
H6 H10 2.6375 no . 8_456
H6 H11 2.9189 no . 8_456
H7 O2 3.1779 no . 5_656
H7 O3 3.0995 no . 2_545
H7 O3 3.5330 no . 5_556
H7 O4 3.0798 no . 2_545
H7 N1 3.4495 no . 2_545
H7 N1 3.5156 no . 5_556
H7 N2 3.5561 no . 5_656
H7 C1 3.4904 no . 5_656
H7 C2 3.4223 no . 5_556
H7 C3 3.4887 no . 2_545
H7 C3 3.2389 no . 5_556
H7 H1 3.0479 no . 2_545
H7 H2 2.9381 no . 2_545
H7 H4 3.4629 no . .
H8 O3 2.3735 no . 2_545
H8 N1 3.4682 no . 5_556
H8 N2 3.1020 no . 5_656
H8 N3 3.2136 no . 5_656
H8 C3 3.4403 no . 2_545
H8 C4 3.4019 no . 5_556
H8 C5 3.5406 no . 5_556
H8 C8 3.4059 no . 5_656
H8 C9 3.1392 no . 5_656
H8 C12 3.0853 no . 5_656
H8 H1 3.5096 no . 5_556
H8 H4 2.7633 no . 5_656
H8 H8 3.4650 no . 5_656
H8 H12 2.4825 no . 5_656
H9 O4 1.78(3) no . .
H9 O4 3.51(3) no . 8_556
H9 C5 3.59(3) no . .
H9 H2 2.26(4) no . .
H9 H2 3.21(4) no . 8_556
H9 H3 2.34(4) no . .
H9 H3 3.29(4) no . 8_556
H9 H5 3.2697 no . .
H10 O1 3.0427 no . 4_555
H10 O1 2.6460 no . 5_656
H10 O4 3.1738 no . 2_545
H10 O4 3.5381 no . 7_646
H10 C1 3.2555 no . 5_656
H10 C6 3.5198 no . .
H10 C6 3.5415 no . 8_556
H10 H2 2.9961 no . 2_545
H10 H3 2.8363 no . 2_545
H10 H3 3.0335 no . 7_646
H10 H6 3.2353 no . .
H10 H6 2.6375 no . 8_556
H10 H11 3.1984 no . 8_556
H11 N3 2.6009 no . 8_456
H11 N4 3.1044 no . 8_456
H11 C5 3.0964 no . 8_556
H11 C6 3.3773 no . 8_556
H11 C10 2.7708 no . 8_456
H11 C11 3.0740 no . 8_456
H11 C12 2.8444 no . 8_456
H11 H4 2.9584 no . 8_456
H11 H5 2.3475 no . 8_556
H11 H6 2.9189 no . 8_556
H11 H10 3.1984 no . 8_456
H11 H12 3.3184 no . 8_456
H12 O2 3.1422 no . 6_556
H12 O3 2.0711 no . 6_556
H12 C1 3.2785 no . 6_556
H12 C3 3.1251 no . 6_556
H12 C4 3.3744 no . .
H12 C8 3.4025 no . 5_656
H12 H5 3.3667 no . 1_655
H12 H8 2.4825 no . 5_656
H12 H11 3.3184 no . 8_556

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H2 O2 . . 6_456 2.8438(19) 0.88(3) 1.99(3) 165(3) no
O4 H3 O1 . . 3_555 2.7390(17) 0.89(3) 1.85(3) 177(3) no
N1 H1 O2 . . 6_456 2.7794(18) 0.92(2) 1.87(2) 170(2) no
N3 H4 N2 . . 5_656 2.884(2) 0.90(2) 1.98(2) 175(2) no
N4 H9 O4 . . . 2.670(2) 0.90(3) 1.78(3) 167(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
