Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007
data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Konstatin Lyssenko'
_publ_contact_author_address     
;
X-ray Structural Center
A.N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of
Sciences
Vavilov Str., 28
Moscow
119991
RUSSIAN FEDERATION
;

_publ_contact_author_email       KOSTYA@XRLAB.INEOS.AC.RU

_publ_section_title              
;
NO3-...NO3- and NO3-...pi interactions in the crystal
of urea nitrate
;

_publ_section_references         
;
Bruker (2005). APEX2 softwarwe package, Bruker AXS Inc., 5465,
East Cheryl Parkway, Madison, WI 5317.

Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software
Suite, Bruker AXS, Madison, Wisconsin, USA.
;

_publ_section_exptl_refinement   
;
The hydrogen atoms were found in difference Fourier synthesis and refined
in isotropic approximation.
;
loop_
_publ_author_name
'Konstatin Lyssenko'
'Mikhail Yu. Antipin'
'Denis G. Golovanov'
'Yulia V. Nelyubina'

data_1
_database_code_depnum_ccdc_archive 'CCDC 651076'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C H5 N2 O, N O3'
_chemical_formula_sum            'C H5 N3 O4'
_chemical_formula_weight         123.08

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.9761(1)
_cell_length_b                   8.2004(1)
_cell_length_c                   7.3668(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.414(1)
_cell_angle_gamma                90.00
_cell_volume                     468.697(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    523
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33142
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         54.99
_reflns_number_total             5960
_reflns_number_gt                4570
_reflns_threshold_expression     I>2/s(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.0153P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5960
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.60046(3) 0.03151(3) 0.35267(4) 0.01300(4) Uani 1 1 d . . .
O1 O 0.85055(3) 0.56216(3) 0.60134(4) 0.01300(4) Uani 1 1 d . . .
N1 N 0.90038(3) 0.29637(3) 0.65576(4) 0.01296(4) Uani 1 1 d . . .
O4 O 0.64690(4) -0.22725(3) 0.39540(4) 0.01543(4) Uani 1 1 d . . .
C1 C 0.80300(3) 0.41159(3) 0.55926(4) 0.00950(4) Uani 1 1 d . . .
N3 N 0.68716(3) -0.08190(3) 0.44137(4) 0.00999(4) Uani 1 1 d . . .
N2 N 0.66542(3) 0.37664(3) 0.42740(4) 0.01252(4) Uani 1 1 d . . .
O2 O 0.81248(4) -0.05184(3) 0.57373(4) 0.01729(5) Uani 1 1 d . . .
H2NB H 0.6313(12) 0.2638(12) 0.3922(12) 0.027(2) Uiso 1 1 d . . .
H1NB H 0.8731(11) 0.1908(11) 0.6260(12) 0.0200(18) Uiso 1 1 d . . .
H1O H 0.7815(12) 0.6352(13) 0.5308(12) 0.029(2) Uiso 1 1 d . . .
H1NA H 0.9894(12) 0.3273(12) 0.7442(12) 0.031(2) Uiso 1 1 d . . .
H2NA H 0.5988(12) 0.4540(11) 0.3613(12) 0.025(2) Uiso 1 1 d . . .

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
O3 0.01418(7) 0.00767(6) 0.01456(8) 0.00144(6) -0.00196(6) 0.00117(5)
O1 0.01415(8) 0.00637(6) 0.01619(9) -0.00015(6) -0.00113(6) -0.00122(5)
N1 0.01319(8) 0.00773(7) 0.01535(10) 0.00188(6) -0.00200(7) 0.00044(6)
O4 0.01829(9) 0.00627(6) 0.01806(10) -0.00057(6) -0.00326(7) -0.00131(6)
C1 0.01028(7) 0.00673(7) 0.01059(8) 0.00027(6) 0.00061(6) -0.00029(6)
N3 0.01075(7) 0.00664(6) 0.01121(8) 0.00020(5) -0.00023(6) -0.00020(5)
N2 0.01284(8) 0.00907(7) 0.01305(9) -0.00045(6) -0.00232(6) -0.00051(6)
O2 0.01664(9) 0.01044(8) 0.01888(10) -0.00086(7) -0.00792(7) -0.00042(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 N3 1.2492(3) . ?
O1 C1 1.3077(3) . ?
O1 H1O 0.894(11) . ?
N1 C1 1.3211(4) . ?
N1 H1NB 0.907(9) . ?
N1 H1NA 0.882(9) . ?
O4 N3 1.2602(3) . ?
C1 N2 1.3173(4) . ?
N3 O2 1.2484(3) . ?
N2 H2NB 0.982(10) . ?
N2 H2NA 0.896(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1O 112.9(6) . . ?
C1 N1 H1NB 118.3(6) . . ?
C1 N1 H1NA 117.6(6) . . ?
H1NB N1 H1NA 124.0(8) . . ?
O1 C1 N2 121.77(2) . . ?
O1 C1 N1 116.47(2) . . ?
N2 C1 N1 121.76(2) . . ?
O2 N3 O3 120.49(2) . . ?
O2 N3 O4 120.31(3) . . ?
O3 N3 O4 119.21(2) . . ?
C1 N2 H2NB 122.2(6) . . ?
C1 N2 H2NA 122.3(6) . . ?
H2NB N2 H2NA 115.5(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2NB O3 1_555 0.982(10) 1.934(10) 2.9068(4) 170.2(8) ?
O1 H1O O2 1_565 0.894(10) 2.591(11) 3.1819(4) 124.4(8) ?
O1 H1O O4 1_565 0.894(10) 1.710(10) 2.6037(4) 179.1(11) ?
N1 H1NB O2 1_555 0.907(9) 2.063(9) 2.9688(4) 176.9(8) ?
N1 H1NA O2 2_756 0.882(9) 2.072(9) 2.9408(4) 167.9(9) ?
N2 H2NA O3 2_655 0.895(9) 2.062(9) 2.8874(4) 152.7(8) ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        54.99
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.071


