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

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'David Turner'
_publ_contact_author_email       DAVID.TURNER@SCI.MONASH.EDU.AU

_publ_section_title              
;
Ammonium Salts of Carbamoyldicyanomethanide,
C(CN)2(CONH2) -. A Comparison of Hydrogen Bond Rich vs. Hydrogen Bond
Poor Cations.
;
loop_
_publ_author_name
'David Turner'
'Stuart Batten'
'Wan Teng Lee.'
'Rose MacDonald'

# Attachment 'Ammonium.CIF'

data_1
_database_code_depnum_ccdc_archive 'CCDC 701912'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Ammonium carbamoyldicyanomethanide
;
_chemical_name_common            NH4cdm
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 N3 O, H4 N'
_chemical_formula_sum            'C4 H6 N4 O'
_chemical_formula_weight         126.13

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   P21/c

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                   5.0491(7)
_cell_length_b                   13.3890(16)
_cell_length_c                   8.5840(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.249(4)
_cell_angle_gamma                90.00
_cell_volume                     575.66(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    1614
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_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            1614
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         24.99
_reflns_number_total             895
_reflns_number_gt                663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_number_reflns         895
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N4 N 0.7607(4) 0.40369(18) -0.4400(3) 0.0165(5) Uani 1 1 d . . .
N1 N 1.3050(4) 0.27782(15) 0.1882(3) 0.0190(5) Uani 1 1 d . . .
N2 N 0.7907(4) 0.31479(14) -0.1214(2) 0.0187(5) Uani 1 1 d . . .
N3 N 0.6761(4) 0.53329(15) 0.2580(2) 0.0204(5) Uani 1 1 d . . .
O1 O 1.2229(3) 0.37837(11) 0.38776(18) 0.0154(4) Uani 1 1 d . . .
C3 C 0.8565(4) 0.35236(16) -0.0019(3) 0.0145(6) Uani 1 1 d . . .
C2 C 1.1627(4) 0.34974(16) 0.2460(3) 0.0132(6) Uani 1 1 d . . .
C4 C 0.7938(5) 0.47048(17) 0.2047(3) 0.0150(6) Uani 1 1 d . . .
C1 C 0.9424(5) 0.39318(16) 0.1463(3) 0.0139(6) Uani 1 1 d . . .
H4A H 0.784(5) 0.3698(17) -0.343(4) 0.029(7) Uiso 1 1 d . . .
H1B H 1.268(5) 0.2567(18) 0.104(3) 0.016(7) Uiso 1 1 d . . .
H4B H 0.766(6) 0.472(2) -0.421(4) 0.054(10) Uiso 1 1 d . . .
H1A H 1.438(6) 0.246(2) 0.265(3) 0.043(9) Uiso 1 1 d . . .
H4C H 0.590(7) 0.380(2) -0.502(4) 0.048(9) Uiso 1 1 d . . .
H4D H 0.901(6) 0.3865(19) -0.497(3) 0.042(8) 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
N4 0.0164(12) 0.0176(14) 0.0153(11) 0.0004(10) 0.0008(10) -0.0008(9)
N1 0.0181(12) 0.0247(14) 0.0127(13) -0.0055(10) -0.0031(10) 0.0056(9)
N2 0.0197(12) 0.0197(13) 0.0153(11) -0.0022(9) -0.0026(9) 0.0032(8)
N3 0.0165(11) 0.0249(13) 0.0190(12) -0.0008(9) -0.0005(9) 0.0039(9)
O1 0.0145(9) 0.0171(10) 0.0134(9) -0.0022(7) -0.0026(7) -0.0003(7)
C3 0.0118(12) 0.0116(14) 0.0197(14) 0.0047(10) 0.0008(10) 0.0024(9)
C2 0.0121(12) 0.0134(14) 0.0140(13) 0.0001(9) 0.0014(10) -0.0048(9)
C4 0.0109(12) 0.0202(15) 0.0128(12) 0.0016(11) -0.0025(10) -0.0022(10)
C1 0.0130(12) 0.0163(14) 0.0118(12) -0.0009(10) -0.0013(9) 0.0005(10)

_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
N4 H4A 0.94(3) . ?
N4 H4B 0.93(3) . ?
N4 H4C 1.00(3) . ?
N4 H4D 0.94(3) . ?
N1 C2 1.334(3) . ?
N1 H1B 0.78(3) . ?
N1 H1A 0.98(3) . ?
N2 C3 1.153(3) . ?
N3 C4 1.157(3) . ?
O1 C2 1.275(3) . ?
C3 C1 1.402(3) . ?
C2 C1 1.438(3) . ?
C4 C1 1.407(3) . ?

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
H4A N4 H4B 109(2) . . ?
H4A N4 H4C 109(2) . . ?
H4B N4 H4C 114(3) . . ?
H4A N4 H4D 109(2) . . ?
H4B N4 H4D 109(3) . . ?
H4C N4 H4D 107(2) . . ?
C2 N1 H1B 122(2) . . ?
C2 N1 H1A 114.8(16) . . ?
H1B N1 H1A 122(2) . . ?
N2 C3 C1 176.9(2) . . ?
O1 C2 N1 119.8(2) . . ?
O1 C2 C1 121.3(2) . . ?
N1 C2 C1 118.9(2) . . ?
N3 C4 C1 177.6(3) . . ?
C3 C1 C4 119.5(2) . . ?
C3 C1 C2 120.7(2) . . ?
C4 C1 C2 119.5(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O1 0.78(3) 2.58(3) 3.306(3) 156(2) 4_565
N1 H1A N2 0.98(3) 2.08(3) 3.035(3) 164(2) 4_666
N4 H4A N2 0.94(3) 2.04(3) 2.969(3) 170(2) .
N4 H4B O1 0.93(3) 2.02(3) 2.952(3) 178(3) 3_765
N4 H4C O1 1.00(3) 1.97(3) 2.943(3) 162(2) 1_454
N4 H4D O1 0.94(3) 2.01(3) 2.935(3) 169(2) 1_554

_diffrn_measured_fraction_theta_max 0.892
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.892
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.052

data_2
_database_code_depnum_ccdc_archive 'CCDC 701913'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Methylammonium carbamoyldicyanomethanide
;
_chemical_name_common            MeH3cdm
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 N3 O, C N H6'
_chemical_formula_sum            'C5 H8 N4 O'
_chemical_formula_weight         140.15

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   P21/n

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

_cell_length_a                   5.8451(3)
_cell_length_b                   12.8144(6)
_cell_length_c                   9.5395(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.573(4)
_cell_angle_gamma                90.00
_cell_volume                     694.57(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    3840
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_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            3840
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1539
_reflns_number_gt                1286
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_number_reflns         1539
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0843(2) 0.24353(11) 0.29627(13) 0.0202(4) Uani 1 1 d . . .
N1 N 0.1441(3) 0.28654(15) 0.51399(18) 0.0234(4) Uani 1 1 d . . .
N2 N 0.6644(3) 0.13170(14) 0.55674(17) 0.0257(4) Uani 1 1 d . . .
N3 N 0.2254(3) 0.08370(14) 0.11181(16) 0.0236(4) Uani 1 1 d . . .
N4 N 0.0801(3) 0.10446(14) 0.78881(17) 0.0187(4) Uani 1 1 d . . .
C1 C 0.2930(3) 0.17009(15) 0.36010(18) 0.0167(4) Uani 1 1 d . . .
C2 C 0.1071(3) 0.23485(15) 0.38839(19) 0.0170(4) Uani 1 1 d . . .
C3 C 0.4996(3) 0.14818(15) 0.46649(19) 0.0184(4) Uani 1 1 d . . .
C4 C 0.2571(3) 0.12242(15) 0.22429(19) 0.0181(4) Uani 1 1 d . . .
C5 C 0.2101(4) 0.02524(17) 0.7258(3) 0.0325(5) Uani 1 1 d . . .
H5B H 0.2177 0.0468 0.6285 0.049 Uiso 1 1 calc R . .
H5C H 0.1288 -0.0420 0.7210 0.049 Uiso 1 1 calc R . .
H5A H 0.3700 0.0184 0.7862 0.049 Uiso 1 1 calc R . .
H1A H 0.015(4) 0.3222(18) 0.533(2) 0.029(6) Uiso 1 1 d . . .
H1B H 0.262(4) 0.2775(18) 0.576(2) 0.023(6) Uiso 1 1 d . . .
H4A H -0.070(5) 0.118(2) 0.725(3) 0.049(8) Uiso 1 1 d . . .
H4B H 0.176(4) 0.1648(19) 0.804(2) 0.034(7) Uiso 1 1 d . . .
H4C H 0.065(4) 0.0880(19) 0.882(3) 0.043(7) 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
O1 0.0174(7) 0.0257(8) 0.0146(6) 0.0007(6) -0.0021(5) 0.0044(6)
N1 0.0201(9) 0.0307(11) 0.0157(8) -0.0050(8) -0.0030(7) 0.0069(8)
N2 0.0199(9) 0.0330(11) 0.0212(8) -0.0017(8) -0.0012(7) 0.0041(8)
N3 0.0243(10) 0.0270(10) 0.0187(8) -0.0005(7) 0.0036(7) 0.0010(8)
N4 0.0173(9) 0.0213(10) 0.0154(8) -0.0002(7) -0.0002(6) -0.0002(7)
C1 0.0161(9) 0.0194(11) 0.0132(8) 0.0007(7) 0.0005(7) 0.0008(8)
C2 0.0179(9) 0.0162(10) 0.0154(8) 0.0012(7) 0.0006(7) -0.0006(8)
C3 0.0188(10) 0.0188(11) 0.0184(9) -0.0018(8) 0.0061(8) 0.0001(8)
C4 0.0153(9) 0.0191(11) 0.0191(9) 0.0036(8) 0.0025(7) 0.0008(8)
C5 0.0269(12) 0.0226(12) 0.0515(14) -0.0025(11) 0.0164(10) 0.0020(9)

_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
O1 C2 1.255(2) . ?
N1 C2 1.341(2) . ?
N1 H1A 0.94(2) . ?
N1 H1B 0.80(2) . ?
N2 C3 1.151(2) . ?
N3 C4 1.157(2) . ?
N4 C5 1.478(3) . ?
N4 H4A 0.96(3) . ?
N4 H4B 0.95(3) . ?
N4 H4C 0.94(3) . ?
C1 C4 1.403(2) . ?
C1 C3 1.411(3) . ?
C1 C2 1.442(3) . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 H5A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 116.5(14) . . ?
C2 N1 H1B 121.0(16) . . ?
H1A N1 H1B 121(2) . . ?
C5 N4 H4A 110.0(16) . . ?
C5 N4 H4B 106.2(15) . . ?
H4A N4 H4B 112(2) . . ?
C5 N4 H4C 113.9(16) . . ?
H4A N4 H4C 111(2) . . ?
H4B N4 H4C 103(2) . . ?
C4 C1 C3 119.64(17) . . ?
C4 C1 C2 117.89(17) . . ?
C3 C1 C2 122.34(16) . . ?
O1 C2 N1 120.80(18) . . ?
O1 C2 C1 120.47(16) . . ?
N1 C2 C1 118.73(17) . . ?
N2 C3 C1 177.64(19) . . ?
N3 C4 C1 179.3(2) . . ?
N4 C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C5 H5A 109.5 . . ?
H5B C5 H5A 109.5 . . ?
H5C C5 H5A 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N3 0.94(2) 2.34(2) 3.271(2) 172.2(19) 4_566
N1 H1B O1 0.80(2) 2.10(2) 2.813(2) 148(2) 4_666
N4 H4A N2 0.96(3) 1.96(3) 2.899(2) 165(2) 1_455
N4 H4B O1 0.95(3) 1.84(3) 2.753(2) 161(2) 4_666
N4 H4C N3 0.94(3) 2.17(3) 3.010(2) 148(2) 1_556

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.055

data_3
_database_code_depnum_ccdc_archive 'CCDC 701914'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
dimethylammonium carbamoyldicyanomethanide
;
_chemical_name_common            '[Me2H2N](cdm)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 N3 O, C2 H8 N'
_chemical_formula_sum            'C6 H10 N4 O'
_chemical_formula_weight         154.18

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.1880(18)
_cell_length_b                   8.2151(21)
_cell_length_c                   8.5656(23)
_cell_angle_alpha                71.608(8)
_cell_angle_beta                 65.906(8)
_cell_angle_gamma                75.772(8)
_cell_volume                     434.13(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    1969
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      24.98

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             164
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_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            1969
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         24.98
_reflns_number_total             1340
_reflns_number_gt                1186
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.103(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1340
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1602
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2003(3) 0.0733(2) 0.0500(3) 0.0243(6) Uani 1 1 d . . .
N1 N -0.1367(4) 0.1799(4) 0.1031(4) 0.0289(7) Uani 1 1 d . . .
N2 N -0.2315(4) 0.5518(3) 0.2759(4) 0.0348(8) Uani 1 1 d . . .
N3 N 0.4163(5) 0.3016(4) 0.2006(4) 0.0400(9) Uani 1 1 d . . .
N4 N 0.4174(4) 0.8313(3) 0.2455(3) 0.0251(7) Uani 1 1 d . . .
C1 C 0.0650(5) 0.3079(4) 0.1858(4) 0.0225(8) Uani 1 1 d . . .
C2 C 0.0449(5) 0.1827(4) 0.1099(4) 0.0226(7) Uani 1 1 d . . .
C3 C -0.0964(5) 0.4430(4) 0.2350(4) 0.0248(8) Uani 1 1 d . . .
C4 C 0.2562(6) 0.3071(4) 0.1935(4) 0.0265(8) Uani 1 1 d . . .
C5 C 0.3027(6) 0.6870(4) 0.2841(5) 0.0402(10) Uani 1 1 d . . .
H5A H 0.3543 0.5836 0.3584 0.060 Uiso 1 1 calc R . .
H5B H 0.3221 0.6622 0.1734 0.060 Uiso 1 1 calc R . .
H5C H 0.1560 0.7200 0.3461 0.060 Uiso 1 1 calc R . .
C6 C 0.4085(6) 0.8697(4) 0.4075(4) 0.0352(9) Uani 1 1 d . . .
H6A H 0.2648 0.9009 0.4791 0.053 Uiso 1 1 calc R . .
H6B H 0.4854 0.9663 0.3739 0.053 Uiso 1 1 calc R . .
H6C H 0.4693 0.7672 0.4758 0.053 Uiso 1 1 calc R . .
H1A H -0.147(5) 0.103(5) 0.053(5) 0.033(10) Uiso 1 1 d . . .
H4A H 0.367(6) 0.932(6) 0.169(5) 0.050(11) Uiso 1 1 d . . .
H4B H 0.565(7) 0.811(6) 0.169(6) 0.066(13) Uiso 1 1 d . . .
H1B H -0.247(6) 0.252(5) 0.146(5) 0.044(11) 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
O1 0.0198(12) 0.0212(11) 0.0309(12) -0.0125(9) -0.0086(9) 0.0059(8)
N1 0.0191(17) 0.0308(15) 0.0411(17) -0.0202(13) -0.0119(13) 0.0059(12)
N2 0.0327(17) 0.0290(15) 0.0355(16) -0.0128(13) -0.0083(13) 0.0078(13)
N3 0.0279(19) 0.0321(16) 0.068(2) -0.0303(15) -0.0188(16) 0.0086(13)
N4 0.0212(16) 0.0251(14) 0.0264(14) -0.0092(12) -0.0086(12) 0.0052(11)
C1 0.0181(19) 0.0203(15) 0.0280(16) -0.0100(13) -0.0070(13) 0.0023(12)
C2 0.0184(18) 0.0217(15) 0.0249(16) -0.0064(12) -0.0068(13) 0.0018(12)
C3 0.0233(18) 0.0245(16) 0.0253(16) -0.0070(13) -0.0094(14) 0.0011(13)
C4 0.023(2) 0.0189(15) 0.0369(18) -0.0153(13) -0.0078(15) 0.0036(12)
C5 0.057(3) 0.0263(18) 0.045(2) -0.0080(15) -0.0265(19) -0.0044(17)
C6 0.043(2) 0.0339(18) 0.0328(18) -0.0155(15) -0.0155(16) 0.0015(16)

_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
O1 C2 1.284(4) . ?
N1 C2 1.336(4) . ?
N1 H1A 0.90(4) . ?
N1 H1B 0.89(4) . ?
N2 C3 1.165(4) . ?
N3 C4 1.166(4) . ?
N4 C5 1.485(4) . ?
N4 C6 1.490(4) . ?
N4 H4A 0.97(4) . ?
N4 H4B 1.00(5) . ?
C1 C4 1.401(5) . ?
C1 C3 1.420(4) . ?
C1 C2 1.440(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 119(2) . . ?
C2 N1 H1B 122(2) . . ?
H1A N1 H1B 119(3) . . ?
C5 N4 C6 113.1(3) . . ?
C5 N4 H4A 109(2) . . ?
C6 N4 H4A 112(2) . . ?
C5 N4 H4B 113(3) . . ?
C6 N4 H4B 108(3) . . ?
H4A N4 H4B 101(3) . . ?
C4 C1 C3 119.2(3) . . ?
C4 C1 C2 118.8(3) . . ?
C3 C1 C2 121.7(3) . . ?
O1 C2 N1 120.0(3) . . ?
O1 C2 C1 120.2(3) . . ?
N1 C2 C1 119.7(3) . . ?
N2 C3 C1 178.7(3) . . ?
N3 C4 C1 178.1(3) . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.90(4) 2.09(4) 2.989(3) 175(3) 2
N4 H4A O1 0.97(4) 1.84(4) 2.775(3) 159(3) 1_565
N4 H4B O1 1.00(5) 2.08(5) 2.950(3) 144(4) 2_665
N4 H4B N2 1.00(5) 2.42(5) 3.003(4) 117(3) 1_655
N1 H1B N3 0.89(4) 2.22(4) 2.963(4) 141(3) 1_455

_diffrn_measured_fraction_theta_max 0.877
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.877
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.057

data_4
_database_code_depnum_ccdc_archive 'CCDC 701915'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
trimethylammonium carbamoyldicyanomethanide
;
_chemical_name_common            '[Me3HN](cdm)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 N3 O, (C3 H10 N)'
_chemical_formula_sum            'C7 H12 N4 O'
_chemical_formula_weight         168.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   C2/c

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

_cell_length_a                   19.6961(12)
_cell_length_b                   7.0629(4)
_cell_length_c                   16.3887(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.203(3)
_cell_angle_gamma                90.00
_cell_volume                     1862.90(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    5317
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_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            5317
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2130
_reflns_number_gt                1882
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_number_reflns         2130
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.02971(6) 0.24169(14) 0.06086(7) 0.0195(2) Uani 1 1 d . . .
N1 N 0.04946(9) -0.04455(18) 0.13221(10) 0.0222(3) Uani 1 1 d . . .
N2 N 0.13631(9) 0.05171(18) 0.39250(10) 0.0266(3) Uani 1 1 d . . .
N3 N 0.10872(10) 0.59259(18) 0.24564(10) 0.0326(4) Uani 1 1 d . . .
N4 N 0.14416(8) 0.43580(18) 0.05124(9) 0.0219(3) Uani 1 1 d . . .
C1 C 0.08922(9) 0.23329(19) 0.23284(10) 0.0174(3) Uani 1 1 d . . .
C2 C 0.05441(9) 0.14404(19) 0.13805(10) 0.0164(3) Uani 1 1 d . . .
C3 C 0.11428(9) 0.13294(19) 0.32027(11) 0.0179(3) Uani 1 1 d . . .
C4 C 0.09940(10) 0.4306(2) 0.23951(10) 0.0210(3) Uani 1 1 d . . .
C5 C 0.21202(12) 0.3007(3) 0.11698(15) 0.0415(5) Uani 1 1 d . . .
H5A H 0.2607 0.3309 0.1173 0.062 Uiso 1 1 calc R . .
H5B H 0.1935 0.1715 0.0921 0.062 Uiso 1 1 calc R . .
H5C H 0.2267 0.3104 0.1850 0.062 Uiso 1 1 calc R . .
C6 C 0.11907(11) 0.4200(2) -0.05261(12) 0.0299(4) Uani 1 1 d . . .
H6A H 0.1024 0.2893 -0.0758 0.045 Uiso 1 1 calc R . .
H6B H 0.1659 0.4550 -0.0552 0.045 Uiso 1 1 calc R . .
H6C H 0.0722 0.5052 -0.0956 0.045 Uiso 1 1 calc R . .
C7 C 0.16779(11) 0.6337(2) 0.08726(13) 0.0308(4) Uani 1 1 d . . .
H7A H 0.1215 0.7186 0.0420 0.046 Uiso 1 1 calc R . .
H7B H 0.2167 0.6696 0.0891 0.046 Uiso 1 1 calc R . .
H7C H 0.1807 0.6436 0.1545 0.046 Uiso 1 1 calc R . .
H1N H 0.0661(13) -0.117(3) 0.1849(16) 0.039(5) Uiso 1 1 d . . .
H2N H 0.0274(12) -0.098(3) 0.0759(15) 0.033(5) Uiso 1 1 d . . .
H3N H 0.1010(12) 0.399(2) 0.0544(13) 0.029(5) 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
O1 0.0224(5) 0.0184(5) 0.0164(5) 0.0009(4) 0.0105(5) -0.0023(4)
N1 0.0318(8) 0.0153(6) 0.0185(7) -0.0016(5) 0.0139(6) -0.0009(5)
N2 0.0345(8) 0.0237(7) 0.0241(7) 0.0030(5) 0.0182(6) 0.0016(6)
N3 0.0505(10) 0.0198(7) 0.0208(7) 0.0000(5) 0.0167(7) -0.0027(6)
N4 0.0193(6) 0.0269(7) 0.0214(6) 0.0040(5) 0.0128(6) 0.0014(5)
C1 0.0197(7) 0.0152(7) 0.0180(7) 0.0001(5) 0.0113(6) -0.0014(5)
C2 0.0146(7) 0.0171(7) 0.0197(7) 0.0004(5) 0.0112(6) -0.0005(5)
C3 0.0192(7) 0.0160(7) 0.0208(7) -0.0029(5) 0.0129(6) -0.0015(5)
C4 0.0252(8) 0.0213(8) 0.0136(7) 0.0001(6) 0.0096(6) -0.0010(6)
C5 0.0305(10) 0.0450(11) 0.0476(11) 0.0250(9) 0.0218(9) 0.0131(8)
C6 0.0343(9) 0.0347(9) 0.0241(8) -0.0040(7) 0.0188(8) -0.0028(7)
C7 0.0268(9) 0.0344(9) 0.0306(9) -0.0104(7) 0.0162(8) -0.0043(7)

_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
O1 C2 1.2661(16) . ?
N1 C2 1.3349(18) . ?
N1 H1N 0.89(2) . ?
N1 H2N 0.85(2) . ?
N2 C3 1.1518(19) . ?
N3 C4 1.1540(19) . ?
N4 C6 1.478(2) . ?
N4 C5 1.482(2) . ?
N4 C7 1.484(2) . ?
N4 H3N 0.92(2) . ?
C1 C4 1.4031(19) . ?
C1 C3 1.4083(19) . ?
C1 C2 1.4328(19) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1N 122.3(12) . . ?
C2 N1 H2N 119.3(13) . . ?
H1N N1 H2N 118.3(17) . . ?
C6 N4 C5 110.57(14) . . ?
C6 N4 C7 110.45(12) . . ?
C5 N4 C7 111.87(14) . . ?
C6 N4 H3N 109.7(11) . . ?
C5 N4 H3N 104.5(11) . . ?
C7 N4 H3N 109.5(11) . . ?
C4 C1 C3 118.04(13) . . ?
C4 C1 C2 118.62(13) . . ?
C3 C1 C2 123.34(12) . . ?
O1 C2 N1 120.12(13) . . ?
O1 C2 C1 120.78(12) . . ?
N1 C2 C1 119.10(13) . . ?
N2 C3 C1 178.71(16) . . ?
N3 C4 C1 179.24(17) . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N N3 0.89(2) 2.22(2) 2.9807(19) 143.2(17) 1_545
N1 H2N O1 0.85(2) 2.10(2) 2.9485(17) 176.7(18) 5
N4 H3N O1 0.92(2) 1.84(2) 2.7197(17) 159.5(16) .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.046

data_5
_database_code_depnum_ccdc_archive 'CCDC 701916'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Tetramethylammonium carbamoyldicyanomethanide
;
_chemical_name_common            Me4Ncdm
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 N3 O, C4 H12 N'
_chemical_formula_sum            'C8 H14 N4 O'
_chemical_formula_weight         182.23

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   P21/c

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                   8.9167(3)
_cell_length_b                   8.8432(3)
_cell_length_c                   13.5613(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.897(2)
_cell_angle_gamma                90.00
_cell_volume                     1065.43(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    7650
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_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            7650
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2435
_reflns_number_gt                2073
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_number_reflns         2435
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44190(9) 0.12428(9) 0.10202(5) 0.0222(2) Uani 1 1 d . . .
N1 N 0.34442(13) 0.10812(13) -0.05693(7) 0.0246(2) Uani 1 1 d . . .
N2 N 0.22744(12) 0.37712(13) 0.23075(7) 0.0272(3) Uani 1 1 d . . .
N3 N 0.02299(12) 0.34555(12) -0.07962(7) 0.0275(3) Uani 1 1 d . . .
N4 N 0.74554(11) 0.36199(11) 0.22528(7) 0.0209(2) Uani 1 1 d . . .
C1 C 0.23056(12) 0.27439(12) 0.05448(8) 0.0169(2) Uani 1 1 d . . .
C2 C 0.34489(12) 0.16575(12) 0.03484(8) 0.0174(2) Uani 1 1 d . . .
C3 C 0.22868(12) 0.33238(13) 0.15118(8) 0.0186(2) Uani 1 1 d . . .
C4 C 0.11547(13) 0.31490(12) -0.01788(8) 0.0179(2) Uani 1 1 d . . .
C5 C 0.81276(17) 0.26303(16) 0.15189(11) 0.0377(3) Uani 1 1 d . . .
H5A H 0.8639 0.3257 0.1054 0.057 Uiso 1 1 calc R . .
H5B H 0.7331 0.2041 0.1155 0.057 Uiso 1 1 calc R . .
H5C H 0.8856 0.1942 0.1865 0.057 Uiso 1 1 calc R . .
C6 C 0.86674(14) 0.45307(14) 0.28000(10) 0.0275(3) Uani 1 1 d . . .
H6A H 0.9159 0.5168 0.2332 0.041 Uiso 1 1 calc R . .
H6B H 0.9412 0.3850 0.3138 0.041 Uiso 1 1 calc R . .
H6C H 0.8227 0.5171 0.3289 0.041 Uiso 1 1 calc R . .
C7 C 0.66884(15) 0.26636(16) 0.29661(10) 0.0337(3) Uani 1 1 d . . .
H7A H 0.7423 0.1979 0.3310 0.051 Uiso 1 1 calc R . .
H7B H 0.5891 0.2070 0.2606 0.051 Uiso 1 1 calc R . .
H7C H 0.6248 0.3314 0.3450 0.051 Uiso 1 1 calc R . .
C8 C 0.63269(15) 0.46541(16) 0.17346(10) 0.0325(3) Uani 1 1 d . . .
H8A H 0.5521 0.4056 0.1387 0.049 Uiso 1 1 calc R . .
H8B H 0.6817 0.5273 0.1256 0.049 Uiso 1 1 calc R . .
H8C H 0.5900 0.5313 0.2220 0.049 Uiso 1 1 calc R . .
H1A H 0.4141(17) 0.0414(17) -0.0678(10) 0.028(4) Uiso 1 1 d . . .
H1B H 0.2790(18) 0.1359(17) -0.1043(11) 0.034(4) 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
O1 0.0219(4) 0.0282(5) 0.0156(4) -0.0027(3) -0.0034(3) 0.0070(3)
N1 0.0261(5) 0.0321(6) 0.0148(5) -0.0045(4) -0.0030(4) 0.0131(5)
N2 0.0291(6) 0.0341(6) 0.0180(5) -0.0053(4) -0.0013(4) 0.0075(5)
N3 0.0293(6) 0.0304(6) 0.0216(5) -0.0030(4) -0.0052(4) 0.0081(5)
N4 0.0172(5) 0.0183(5) 0.0273(5) -0.0014(4) 0.0027(4) -0.0002(4)
C1 0.0179(5) 0.0190(5) 0.0134(5) -0.0004(4) -0.0006(4) 0.0017(4)
C2 0.0174(5) 0.0194(6) 0.0153(5) 0.0005(4) 0.0007(4) -0.0014(4)
C3 0.0170(5) 0.0192(6) 0.0193(6) 0.0014(4) -0.0001(4) 0.0028(4)
C4 0.0213(6) 0.0168(5) 0.0157(5) -0.0022(4) 0.0026(4) 0.0016(4)
C5 0.0355(8) 0.0353(8) 0.0435(8) -0.0146(6) 0.0109(6) 0.0027(6)
C6 0.0238(6) 0.0244(6) 0.0334(7) -0.0003(5) -0.0024(5) -0.0044(5)
C7 0.0306(7) 0.0343(7) 0.0367(7) 0.0067(6) 0.0052(6) -0.0097(6)
C8 0.0232(6) 0.0337(7) 0.0399(8) 0.0067(6) -0.0023(5) 0.0050(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
O1 C2 1.2563(13) . ?
N1 C2 1.3445(14) . ?
N1 H1A 0.878(16) . ?
N1 H1B 0.866(16) . ?
N2 C3 1.1503(14) . ?
N3 C4 1.1561(15) . ?
N4 C5 1.4891(15) . ?
N4 C8 1.4906(15) . ?
N4 C6 1.4934(15) . ?
N4 C7 1.4939(15) . ?
C1 C4 1.4044(15) . ?
C1 C3 1.4096(15) . ?
C1 C2 1.4421(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 117.6(9) . . ?
C2 N1 H1B 121.9(10) . . ?
H1A N1 H1B 120.5(13) . . ?
C5 N4 C8 109.85(10) . . ?
C5 N4 C6 109.49(10) . . ?
C8 N4 C6 109.52(10) . . ?
C5 N4 C7 109.44(10) . . ?
C8 N4 C7 108.94(10) . . ?
C6 N4 C7 109.60(10) . . ?
C4 C1 C3 119.42(10) . . ?
C4 C1 C2 121.79(9) . . ?
C3 C1 C2 118.62(9) . . ?
O1 C2 N1 120.54(10) . . ?
O1 C2 C1 120.96(10) . . ?
N1 C2 C1 118.50(10) . . ?
N2 C3 C1 178.77(12) . . ?
N3 C4 C1 177.82(12) . . ?
N4 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.878(16) 2.028(16) 2.9029(13) 174.0(13) 3_655
N1 H1B N2 0.866(16) 2.247(16) 2.9803(14) 142.4(13) 4_565

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039

data_6
_database_code_depnum_ccdc_archive 'CCDC 701917'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Triethylmethylammonium carbamoyldicyanomethanide
;
_chemical_name_common            
'Triethylmethylammonium carbamoyldicyanomethanide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H18 N, C4 H2 N3 O'
_chemical_formula_sum            'C11 H20 N4 O'
_chemical_formula_weight         224.31

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   P21/c

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                   19.1746(18)
_cell_length_b                   9.5707(8)
_cell_length_c                   13.9859(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.109(4)
_cell_angle_gamma                90.00
_cell_volume                     2562.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    7784
_cell_measurement_theta_min      1.06
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_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            7784
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.06
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4020
_reflns_number_gt                3203
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_number_reflns         4020
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.1091
_refine_ls_wR_factor_ref         0.2425
_refine_ls_wR_factor_gt          0.2274
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_restrained_S_all      1.207
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28058(13) 0.5938(3) 0.1566(2) 0.0174(8) Uani 1 1 d . . .
O2 O 0.22384(14) 0.3984(3) 0.3613(2) 0.0201(8) Uani 1 1 d . . .
N1 N 0.3122(2) 0.6286(5) 0.3118(3) 0.0227(10) Uani 1 1 d . . .
N2 N 0.4541(2) 0.8729(5) 0.3155(4) 0.0342(12) Uani 1 1 d . . .
N3 N 0.37530(19) 0.8213(4) 0.0151(4) 0.0250(10) Uani 1 1 d . . .
N4 N 0.1955(2) 0.3548(5) 0.2051(3) 0.0202(10) Uani 1 1 d . . .
N5 N 0.05635(19) 0.1057(4) 0.2019(3) 0.0289(11) Uani 1 1 d . . .
N6 N 0.12018(19) 0.1885(4) 0.5042(3) 0.0244(10) Uani 1 1 d . . .
N7 N 0.11931(17) 0.6876(4) 0.5077(3) 0.0197(9) Uani 1 1 d . . .
N8 N 0.38301(16) 0.1679(4) 0.4783(3) 0.0195(10) Uani 1 1 d . . .
C1 C 0.3694(2) 0.7564(4) 0.1926(4) 0.0144(10) Uani 1 1 d . . .
C2 C 0.31851(19) 0.6547(4) 0.2194(4) 0.0148(10) Uani 1 1 d . . .
C3 C 0.4163(2) 0.8207(4) 0.2596(4) 0.0186(11) Uani 1 1 d . . .
C4 C 0.37320(19) 0.7924(4) 0.0950(4) 0.0181(11) Uani 1 1 d . . .
C5 C 0.1334(2) 0.2396(4) 0.3265(4) 0.0154(10) Uani 1 1 d . . .
C6 C 0.1863(2) 0.3364(4) 0.2990(4) 0.0155(10) Uani 1 1 d . . .
C7 C 0.0906(2) 0.1660(4) 0.2588(4) 0.0155(10) Uani 1 1 d . . .
C8 C 0.1264(2) 0.2116(4) 0.4236(4) 0.0177(11) Uani 1 1 d . . .
C9 C 0.0880(3) 0.5585(5) 0.4594(5) 0.0361(15) Uani 1 1 d . . .
H9A H 0.1177 0.5281 0.4085 0.054 Uiso 1 1 calc R . .
H9B H 0.0412 0.5804 0.4318 0.054 Uiso 1 1 calc R . .
H9C H 0.0848 0.4836 0.5067 0.054 Uiso 1 1 calc R . .
C10 C 0.1936(2) 0.6581(5) 0.5395(5) 0.0326(14) Uani 1 1 d . . .
H10A H 0.2145 0.7448 0.5669 0.039 Uiso 1 1 calc R . .
H10B H 0.2195 0.6333 0.4825 0.039 Uiso 1 1 calc R . .
C11 C 0.2036(2) 0.5426(6) 0.6125(5) 0.0373(15) Uani 1 1 d . . .
H11A H 0.1808 0.5684 0.6710 0.056 Uiso 1 1 calc R . .
H11B H 0.2536 0.5283 0.6273 0.056 Uiso 1 1 calc R . .
H11C H 0.1829 0.4560 0.5865 0.056 Uiso 1 1 calc R . .
C12 C 0.0737(2) 0.7223(5) 0.5896(4) 0.0279(13) Uani 1 1 d . . .
H12A H 0.0253 0.7377 0.5637 0.034 Uiso 1 1 calc R . .
H12B H 0.0732 0.6412 0.6336 0.034 Uiso 1 1 calc R . .
C13 C 0.0974(3) 0.8485(6) 0.6452(5) 0.0429(16) Uani 1 1 d . . .
H13A H 0.1434 0.8305 0.6768 0.064 Uiso 1 1 calc R . .
H13B H 0.0639 0.8697 0.6936 0.064 Uiso 1 1 calc R . .
H13C H 0.1006 0.9282 0.6016 0.064 Uiso 1 1 calc R . .
C14 C 0.1203(3) 0.8044(5) 0.4347(5) 0.0375(15) Uani 1 1 d . . .
H14A H 0.1475 0.8831 0.4636 0.045 Uiso 1 1 calc R . .
H14B H 0.1455 0.7708 0.3792 0.045 Uiso 1 1 calc R . .
C15 C 0.0507(3) 0.8590(6) 0.3986(5) 0.0471(18) Uani 1 1 d . . .
H15A H 0.0212 0.7811 0.3756 0.071 Uiso 1 1 calc R . .
H15B H 0.0570 0.9246 0.3459 0.071 Uiso 1 1 calc R . .
H15C H 0.0283 0.9072 0.4506 0.071 Uiso 1 1 calc R . .
C16 C 0.4062(2) 0.0389(4) 0.5302(4) 0.0209(11) Uani 1 1 d . . .
H16A H 0.3665 -0.0029 0.5609 0.031 Uiso 1 1 calc R . .
H16B H 0.4428 0.0626 0.5792 0.031 Uiso 1 1 calc R . .
H16C H 0.4246 -0.0279 0.4849 0.031 Uiso 1 1 calc R . .
C17 C 0.3398(3) 0.2580(6) 0.5385(4) 0.0342(14) Uani 1 1 d . . .
H17A H 0.2987 0.2038 0.5574 0.041 Uiso 1 1 calc R . .
H17B H 0.3223 0.3385 0.4997 0.041 Uiso 1 1 calc R . .
C18 C 0.3785(3) 0.3123(6) 0.6279(5) 0.0450(16) Uani 1 1 d . . .
H18A H 0.4207 0.3617 0.6103 0.067 Uiso 1 1 calc R . .
H18B H 0.3916 0.2338 0.6701 0.067 Uiso 1 1 calc R . .
H18C H 0.3483 0.3767 0.6612 0.067 Uiso 1 1 calc R . .
C19 C 0.4474(2) 0.2406(5) 0.4471(5) 0.0312(14) Uani 1 1 d . . .
H19A H 0.4719 0.1773 0.4042 0.037 Uiso 1 1 calc R . .
H19B H 0.4789 0.2577 0.5043 0.037 Uiso 1 1 calc R . .
C20 C 0.4341(3) 0.3787(5) 0.3956(5) 0.0423(17) Uani 1 1 d . . .
H20A H 0.4132 0.4451 0.4391 0.063 Uiso 1 1 calc R . .
H20B H 0.4021 0.3637 0.3395 0.063 Uiso 1 1 calc R . .
H20C H 0.4784 0.4164 0.3751 0.063 Uiso 1 1 calc R . .
C21 C 0.3391(3) 0.1275(6) 0.3876(5) 0.0371(15) Uani 1 1 d . . .
H21A H 0.3170 0.2130 0.3600 0.045 Uiso 1 1 calc R . .
H21B H 0.3707 0.0900 0.3401 0.045 Uiso 1 1 calc R . .
C22 C 0.2832(3) 0.0220(6) 0.4025(5) 0.0460(18) Uani 1 1 d . . .
H22A H 0.2534 0.0548 0.4526 0.069 Uiso 1 1 calc R . .
H22B H 0.3047 -0.0672 0.4220 0.069 Uiso 1 1 calc R . .
H22C H 0.2549 0.0092 0.3427 0.069 Uiso 1 1 calc R . .
H1N H 0.284(3) 0.555(6) 0.320(4) 0.030(15) Uiso 1 1 d . . .
H2N H 0.335(3) 0.660(7) 0.353(6) 0.06(2) Uiso 1 1 d . . .
H3N H 0.219(2) 0.422(5) 0.197(4) 0.009(12) Uiso 1 1 d . . .
H4N H 0.169(2) 0.324(5) 0.163(4) 0.015(13) 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
O1 0.0183(14) 0.0263(17) 0.007(2) -0.0010(13) -0.0049(13) -0.0072(13)
O2 0.0208(14) 0.0308(18) 0.008(2) 0.0007(14) -0.0033(13) -0.0065(13)
N1 0.028(2) 0.026(2) 0.013(3) 0.0001(18) -0.0018(18) -0.0097(19)
N2 0.028(2) 0.050(3) 0.024(3) -0.015(2) -0.0002(19) -0.014(2)
N3 0.028(2) 0.032(2) 0.016(3) 0.008(2) 0.0016(17) -0.0088(17)
N4 0.025(2) 0.027(2) 0.009(3) -0.0039(18) 0.0018(18) -0.0117(19)
N5 0.030(2) 0.033(2) 0.024(3) 0.000(2) -0.0004(19) -0.0129(19)
N6 0.035(2) 0.027(2) 0.011(3) 0.0021(18) 0.0021(18) -0.0036(17)
N7 0.0202(17) 0.0189(19) 0.020(3) 0.0000(17) 0.0004(16) -0.0006(15)
N8 0.0143(16) 0.022(2) 0.022(3) 0.0029(17) -0.0027(15) 0.0054(15)
C1 0.0181(19) 0.017(2) 0.008(3) 0.0030(18) -0.0008(17) 0.0003(17)
C2 0.0163(19) 0.020(2) 0.008(3) -0.0003(19) 0.0018(17) 0.0023(17)
C3 0.022(2) 0.019(2) 0.015(3) 0.0012(19) 0.0040(19) -0.0022(18)
C4 0.0105(18) 0.017(2) 0.027(4) -0.001(2) -0.0036(18) -0.0032(16)
C5 0.0176(19) 0.023(2) 0.005(3) 0.0025(19) 0.0019(17) 0.0004(17)
C6 0.0192(19) 0.017(2) 0.010(3) 0.0013(18) 0.0018(18) 0.0042(17)
C7 0.021(2) 0.021(2) 0.006(3) 0.0047(19) 0.0069(18) 0.0023(18)
C8 0.020(2) 0.014(2) 0.018(4) -0.0006(19) -0.0010(19) -0.0057(17)
C9 0.033(3) 0.022(3) 0.053(5) -0.007(3) -0.004(3) -0.001(2)
C10 0.014(2) 0.034(3) 0.050(5) -0.013(3) 0.003(2) -0.004(2)
C11 0.021(2) 0.039(3) 0.050(5) 0.006(3) -0.007(2) 0.005(2)
C12 0.020(2) 0.027(3) 0.037(4) 0.008(2) 0.003(2) 0.000(2)
C13 0.036(3) 0.046(3) 0.047(5) -0.011(3) 0.004(3) 0.008(3)
C14 0.052(3) 0.023(3) 0.038(5) -0.001(2) 0.002(3) -0.010(2)
C15 0.062(4) 0.036(3) 0.041(5) 0.015(3) -0.012(3) -0.006(3)
C16 0.020(2) 0.018(2) 0.024(3) 0.004(2) -0.0046(19) -0.0008(18)
C17 0.034(3) 0.044(3) 0.026(4) 0.006(3) 0.011(2) 0.013(2)
C18 0.060(4) 0.042(3) 0.033(5) -0.002(3) 0.003(3) 0.027(3)
C19 0.030(2) 0.027(3) 0.039(4) 0.004(2) 0.021(2) 0.005(2)
C20 0.053(3) 0.029(3) 0.048(5) 0.013(3) 0.025(3) 0.013(3)
C21 0.038(3) 0.043(3) 0.029(4) 0.001(3) -0.005(2) 0.011(2)
C22 0.031(3) 0.044(3) 0.060(5) -0.013(3) -0.022(3) 0.004(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.254(5) . ?
O2 C6 1.249(5) . ?
N1 C2 1.328(7) . ?
N1 H1N 0.90(6) . ?
N1 H2N 0.76(8) . ?
N2 C3 1.151(6) . ?
N3 C4 1.154(6) . ?
N4 C6 1.346(7) . ?
N4 H3N 0.80(5) . ?
N4 H4N 0.81(5) . ?
N5 C7 1.159(6) . ?
N6 C8 1.162(6) . ?
N7 C10 1.495(5) . ?
N7 C14 1.514(7) . ?
N7 C12 1.515(7) . ?
N7 C9 1.516(6) . ?
N8 C16 1.488(5) . ?
N8 C17 1.489(7) . ?
N8 C19 1.502(6) . ?
N8 C21 1.533(7) . ?
C1 C3 1.405(6) . ?
C1 C4 1.413(7) . ?
C1 C2 1.442(6) . ?
C5 C8 1.397(7) . ?
C5 C7 1.408(6) . ?
C5 C6 1.442(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.510(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.494(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.496(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.511(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.520(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.495(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1N 111(4) . . ?
C2 N1 H2N 126(6) . . ?
H1N N1 H2N 122(7) . . ?
C6 N4 H3N 110(4) . . ?
C6 N4 H4N 124(4) . . ?
H3N N4 H4N 122(5) . . ?
C10 N7 C14 107.0(4) . . ?
C10 N7 C12 113.3(4) . . ?
C14 N7 C12 112.1(4) . . ?
C10 N7 C9 109.1(3) . . ?
C14 N7 C9 108.7(4) . . ?
C12 N7 C9 106.5(4) . . ?
C16 N8 C17 111.4(4) . . ?
C16 N8 C19 107.3(3) . . ?
C17 N8 C19 112.8(4) . . ?
C16 N8 C21 109.3(4) . . ?
C17 N8 C21 108.5(4) . . ?
C19 N8 C21 107.4(4) . . ?
C3 C1 C4 118.2(4) . . ?
C3 C1 C2 122.7(5) . . ?
C4 C1 C2 119.1(4) . . ?
O1 C2 N1 121.0(4) . . ?
O1 C2 C1 120.4(5) . . ?
N1 C2 C1 118.6(4) . . ?
N2 C3 C1 179.0(6) . . ?
N3 C4 C1 179.0(4) . . ?
C8 C5 C7 118.3(4) . . ?
C8 C5 C6 119.3(4) . . ?
C7 C5 C6 122.3(5) . . ?
O2 C6 N4 121.2(4) . . ?
O2 C6 C5 120.4(5) . . ?
N4 C6 C5 118.4(4) . . ?
N5 C7 C5 178.8(5) . . ?
N6 C8 C5 179.7(5) . . ?
N7 C9 H9A 109.5 . . ?
N7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N7 C10 C11 115.1(4) . . ?
N7 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
N7 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N7 113.5(4) . . ?
C13 C12 H12A 108.9 . . ?
N7 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
N7 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N7 116.2(5) . . ?
C15 C14 H14A 108.2 . . ?
N7 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
N7 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N8 C16 H16A 109.5 . . ?
N8 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N8 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N8 C17 C18 113.8(4) . . ?
N8 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
N8 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N8 C19 C20 114.9(4) . . ?
N8 C19 H19A 108.5 . . ?
C20 C19 H19A 108.5 . . ?
N8 C19 H19B 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 N8 114.9(5) . . ?
C22 C21 H21A 108.6 . . ?
N8 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
N8 C21 H21B 108.6 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O2 0.90(6) 2.00(6) 2.886(5) 171(5) .
N4 H3N O1 0.80(5) 2.12(5) 2.912(5) 172(5) .
N4 H4N N6 0.81(5) 2.36(6) 3.115(6) 154(5) 4_565
N1 H2N N3 0.76(8) 2.36(8) 3.067(7) 154(7) 4_576

_diffrn_measured_fraction_theta_max 0.891
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.891
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.069

data_7
_database_code_depnum_ccdc_archive 'CCDC 701918'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Benzyltrimethylammonium Carbamoyldicyanomethanide
;
_chemical_name_common            BzMe3N(cdm)
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 N, C4 H2 N3 O'
_chemical_formula_sum            'C14 H18 N4 O'
_chemical_formula_weight         258.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   P21

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

_cell_length_a                   9.4203(19)
_cell_length_b                   17.1223(36)
_cell_length_c                   9.8809(23)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.939(7)
_cell_angle_gamma                90.00
_cell_volume                     1420.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    6809
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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 X8 Apex II CCD'
_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            6809
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3528
_reflns_number_gt                3155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Compound refined as a racemic twin.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(0)
_refine_ls_number_reflns         3528
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0351(3) 0.23712(14) 0.3229(3) 0.0269(6) Uani 1 1 d . . .
O2 O 0.9360(3) 0.03489(13) 0.2887(3) 0.0255(6) Uani 1 1 d . . .
N1 N 0.1963(5) 0.13878(17) 0.3281(4) 0.0262(7) Uani 1 1 d . . .
N2 N 0.5685(4) 0.22732(18) 0.3981(4) 0.0348(9) Uani 1 1 d . . .
N3 N 0.2347(4) 0.41767(19) 0.3351(4) 0.0343(8) Uani 1 1 d . . .
N4 N 0.8217(5) 0.12915(17) 0.3669(4) 0.0261(7) Uani 1 1 d . . .
N5 N 0.4839(4) 0.03840(17) 0.3813(4) 0.0271(7) Uani 1 1 d . . .
N6 N 0.6652(4) -0.12719(19) 0.1592(5) 0.0406(9) Uani 1 1 d . . .
N7 N 0.2436(4) 0.60423(17) 0.1278(3) 0.0234(7) Uani 1 1 d . . .
N8 N 0.7897(4) 0.41179(17) 0.3603(4) 0.0257(7) Uani 1 1 d . . .
C1 C 0.2915(4) 0.2705(2) 0.3581(4) 0.0228(8) Uani 1 1 d . . .
C2 C 0.1681(5) 0.21519(19) 0.3367(4) 0.0216(8) Uani 1 1 d . . .
C3 C 0.4431(5) 0.24741(19) 0.3795(4) 0.0236(8) Uani 1 1 d . . .
C4 C 0.2579(4) 0.3520(2) 0.3460(5) 0.0255(8) Uani 1 1 d . . .
C5 C 0.6991(4) 0.00313(19) 0.2990(4) 0.0212(7) Uani 1 1 d . . .
C6 C 0.8240(4) 0.05596(19) 0.3167(4) 0.0235(8) Uani 1 1 d . . .
C7 C 0.5812(4) 0.02184(19) 0.3447(4) 0.0229(8) Uani 1 1 d . . .
C8 C 0.6829(5) -0.06915(19) 0.2248(5) 0.0276(8) Uani 1 1 d . . .
C9 C 0.0865(5) 0.5836(2) 0.1212(6) 0.0411(12) Uani 1 1 d . . .
H9A H 0.0103 0.5713 0.0162 0.062 Uiso 1 1 calc R . .
H9B H 0.0469 0.6279 0.1572 0.062 Uiso 1 1 calc R . .
H9C H 0.0992 0.5381 0.1858 0.062 Uiso 1 1 calc R . .
C10 C 0.3007(5) 0.5344(2) 0.0749(4) 0.0318(9) Uani 1 1 d . . .
H10A H 0.3130 0.4900 0.1420 0.048 Uiso 1 1 calc R . .
H10B H 0.4035 0.5464 0.0771 0.048 Uiso 1 1 calc R . .
H10C H 0.2230 0.5212 -0.0290 0.048 Uiso 1 1 calc R . .
C11 C 0.3617(5) 0.6224(2) 0.2881(5) 0.0408(11) Uani 1 1 d . . .
H11A H 0.3227 0.6663 0.3257 0.061 Uiso 1 1 calc R . .
H11B H 0.4641 0.6364 0.2912 0.061 Uiso 1 1 calc R . .
H11C H 0.3757 0.5765 0.3521 0.061 Uiso 1 1 calc R . .
C12 C 0.2257(5) 0.67214(19) 0.0220(4) 0.0260(8) Uani 1 1 d . . .
H12A H 0.3273 0.6790 0.0166 0.031 Uiso 1 1 calc R . .
H12B H 0.1429 0.6587 -0.0811 0.031 Uiso 1 1 calc R . .
C13 C 0.1816(5) 0.7487(2) 0.0689(4) 0.0261(8) Uani 1 1 d . . .
C14 C 0.0237(5) 0.7658(2) 0.0293(4) 0.0293(9) Uani 1 1 d . . .
H14 H -0.0579 0.7294 -0.0272 0.035 Uiso 1 1 calc R . .
C15 C -0.0142(6) 0.8377(2) 0.0737(5) 0.0399(11) Uani 1 1 d . . .
H15 H -0.1221 0.8499 0.0470 0.048 Uiso 1 1 calc R . .
C16 C 0.1042(7) 0.8906(2) 0.1558(5) 0.0447(12) Uani 1 1 d . . .
H16 H 0.0781 0.9389 0.1866 0.054 Uiso 1 1 calc R . .
C17 C 0.2598(7) 0.8734(2) 0.1929(5) 0.0465(12) Uani 1 1 d . . .
H17 H 0.3411 0.9102 0.2482 0.056 Uiso 1 1 calc R . .
C18 C 0.2995(6) 0.8026(2) 0.1502(5) 0.0358(10) Uani 1 1 d . . .
H18 H 0.4076 0.7910 0.1768 0.043 Uiso 1 1 calc R . .
C19 C 0.6885(5) 0.4503(2) 0.4227(5) 0.0319(9) Uani 1 1 d . . .
H19A H 0.6125 0.4857 0.3464 0.048 Uiso 1 1 calc R . .
H19B H 0.7567 0.4800 0.5141 0.048 Uiso 1 1 calc R . .
H19C H 0.6304 0.4103 0.4485 0.048 Uiso 1 1 calc R . .
C20 C 0.6877(6) 0.3666(3) 0.2202(5) 0.0418(11) Uani 1 1 d . . .
H20A H 0.6246 0.3283 0.2434 0.063 Uiso 1 1 calc R . .
H20B H 0.7555 0.3394 0.1839 0.063 Uiso 1 1 calc R . .
H20C H 0.6163 0.4025 0.1415 0.063 Uiso 1 1 calc R . .
C21 C 0.9027(5) 0.3572(2) 0.4792(5) 0.0342(9) Uani 1 1 d . . .
H21A H 0.8421 0.3163 0.4998 0.051 Uiso 1 1 calc R . .
H21B H 0.9663 0.3864 0.5727 0.051 Uiso 1 1 calc R . .
H21C H 0.9735 0.3331 0.4428 0.051 Uiso 1 1 calc R . .
C22 C 0.8894(5) 0.4716(2) 0.3269(5) 0.0278(9) Uani 1 1 d . . .
H22A H 0.9748 0.4903 0.4248 0.033 Uiso 1 1 calc R . .
H22B H 0.9413 0.4450 0.2721 0.033 Uiso 1 1 calc R . .
C23 C 0.8009(4) 0.5416(2) 0.2353(4) 0.0237(8) Uani 1 1 d . . .
C24 C 0.7264(5) 0.5419(2) 0.0768(4) 0.0309(9) Uani 1 1 d . . .
H24 H 0.7212 0.4951 0.0230 0.037 Uiso 1 1 calc R . .
C25 C 0.6601(5) 0.6098(2) -0.0025(5) 0.0345(10) Uani 1 1 d . . .
H25 H 0.6092 0.6092 -0.1103 0.041 Uiso 1 1 calc R . .
C26 C 0.6670(5) 0.6784(2) 0.0731(5) 0.0335(9) Uani 1 1 d . . .
H26 H 0.6224 0.7249 0.0174 0.040 Uiso 1 1 calc R . .
C27 C 0.7389(5) 0.6797(2) 0.2305(5) 0.0338(9) Uani 1 1 d . . .
H27 H 0.7427 0.7266 0.2832 0.041 Uiso 1 1 calc R . .
C28 C 0.8058(5) 0.6110(2) 0.3105(5) 0.0301(9) Uani 1 1 d . . .
H28 H 0.8556 0.6118 0.4184 0.036 Uiso 1 1 calc R . .
H1A H 0.290(5) 0.123(2) 0.350(5) 0.029(12) Uiso 1 1 d . . .
H1B H 0.123(5) 0.111(3) 0.323(5) 0.036(13) Uiso 1 1 d . . .
H4A H 0.738(5) 0.146(2) 0.372(4) 0.020(10) Uiso 1 1 d . . .
H4B H 0.898(5) 0.164(2) 0.369(5) 0.030(11) 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
O1 0.0241(16) 0.0243(12) 0.0368(15) -0.0014(11) 0.0178(12) 0.0002(11)
O2 0.0217(14) 0.0243(12) 0.0352(14) -0.0022(11) 0.0170(12) 0.0015(11)
N1 0.022(2) 0.0197(15) 0.041(2) 0.0046(13) 0.0179(16) 0.0031(15)
N2 0.028(2) 0.0238(16) 0.059(3) 0.0054(15) 0.0248(18) -0.0010(15)
N3 0.029(2) 0.0249(15) 0.052(2) 0.0002(15) 0.0215(17) 0.0002(15)
N4 0.0169(19) 0.0238(15) 0.044(2) -0.0097(13) 0.0196(16) -0.0043(14)
N5 0.0297(19) 0.0226(14) 0.0322(17) -0.0028(13) 0.0168(15) -0.0013(14)
N6 0.045(2) 0.0256(16) 0.067(3) -0.0097(17) 0.040(2) -0.0072(17)
N7 0.0214(18) 0.0257(15) 0.0285(17) 0.0035(13) 0.0159(14) 0.0031(13)
N8 0.0261(18) 0.0244(14) 0.0324(18) -0.0024(13) 0.0183(15) -0.0033(14)
C1 0.018(2) 0.0208(16) 0.031(2) 0.0026(14) 0.0123(16) -0.0009(15)
C2 0.023(2) 0.0212(16) 0.0252(19) 0.0002(14) 0.0145(16) 0.0022(15)
C3 0.023(2) 0.0199(16) 0.032(2) 0.0015(14) 0.0162(17) -0.0029(16)
C4 0.018(2) 0.0226(17) 0.039(2) -0.0013(15) 0.0160(17) -0.0054(16)
C5 0.0154(19) 0.0187(15) 0.033(2) 0.0014(14) 0.0141(15) 0.0009(14)
C6 0.021(2) 0.0241(17) 0.0238(18) 0.0025(14) 0.0087(16) 0.0018(16)
C7 0.025(2) 0.0170(15) 0.0276(19) 0.0032(13) 0.0125(16) -0.0018(15)
C8 0.026(2) 0.0209(17) 0.043(2) -0.0003(15) 0.0227(18) -0.0015(16)
C9 0.034(3) 0.029(2) 0.073(3) 0.018(2) 0.036(2) 0.0071(19)
C10 0.035(2) 0.0268(17) 0.038(2) 0.0002(17) 0.0205(19) 0.0083(18)
C11 0.051(3) 0.039(2) 0.026(2) 0.0026(17) 0.013(2) 0.007(2)
C12 0.029(2) 0.0246(17) 0.0256(19) 0.0022(15) 0.0135(16) 0.0010(17)
C13 0.032(2) 0.0216(16) 0.028(2) 0.0000(14) 0.0169(17) -0.0009(16)
C14 0.035(3) 0.0274(17) 0.029(2) 0.0033(15) 0.0183(18) 0.0037(18)
C15 0.047(3) 0.037(2) 0.041(2) 0.0059(19) 0.025(2) 0.017(2)
C16 0.081(4) 0.0237(19) 0.042(3) -0.0005(17) 0.039(3) 0.006(2)
C17 0.071(4) 0.029(2) 0.046(3) -0.0089(19) 0.033(3) -0.017(2)
C18 0.041(3) 0.0324(19) 0.042(2) -0.0025(18) 0.026(2) -0.011(2)
C19 0.031(2) 0.0322(19) 0.042(2) 0.0047(17) 0.0255(19) 0.0083(18)
C20 0.052(3) 0.040(2) 0.036(2) -0.0109(18) 0.022(2) -0.019(2)
C21 0.037(3) 0.0306(19) 0.041(2) 0.0025(17) 0.023(2) 0.0072(19)
C22 0.023(2) 0.0250(17) 0.040(2) -0.0023(15) 0.0187(18) -0.0033(16)
C23 0.021(2) 0.0273(17) 0.0277(18) -0.0019(15) 0.0151(15) -0.0047(15)
C24 0.033(2) 0.0340(19) 0.034(2) -0.0073(17) 0.0230(18) -0.0126(18)
C25 0.032(2) 0.045(2) 0.028(2) 0.0013(18) 0.0152(18) -0.010(2)
C26 0.030(2) 0.0324(19) 0.039(2) 0.0040(17) 0.0155(19) -0.0059(19)
C27 0.039(3) 0.0243(17) 0.042(2) -0.0046(17) 0.022(2) -0.0022(19)
C28 0.035(3) 0.0312(19) 0.028(2) -0.0028(16) 0.0172(18) -0.0018(18)

_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
O1 C2 1.255(4) . ?
O2 C6 1.259(4) . ?
N1 C2 1.345(4) . ?
N1 H1A 0.85(4) . ?
N1 H1B 0.82(4) . ?
N2 C3 1.162(5) . ?
N3 C4 1.141(5) . ?
N4 C6 1.352(4) . ?
N4 H4A 0.86(4) . ?
N4 H4B 0.93(4) . ?
N5 C7 1.163(4) . ?
N6 C8 1.156(5) . ?
N7 C9 1.494(5) . ?
N7 C11 1.499(5) . ?
N7 C10 1.499(4) . ?
N7 C12 1.521(4) . ?
N8 C20 1.494(5) . ?
N8 C21 1.502(5) . ?
N8 C19 1.502(5) . ?
N8 C22 1.524(4) . ?
C1 C3 1.403(5) . ?
C1 C4 1.424(5) . ?
C1 C2 1.439(5) . ?
C5 C8 1.411(5) . ?
C5 C7 1.412(5) . ?
C5 C6 1.431(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.510(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.385(5) . ?
C13 C14 1.387(5) . ?
C14 C15 1.405(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.506(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.391(5) . ?
C23 C24 1.396(5) . ?
C24 C25 1.384(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.397(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 120(3) . . ?
C2 N1 H1B 113(3) . . ?
H1A N1 H1B 125(4) . . ?
C6 N4 H4A 120(2) . . ?
C6 N4 H4B 117(2) . . ?
H4A N4 H4B 120(3) . . ?
C9 N7 C11 110.0(3) . . ?
C9 N7 C10 107.5(3) . . ?
C11 N7 C10 108.8(3) . . ?
C9 N7 C12 110.6(3) . . ?
C11 N7 C12 111.4(3) . . ?
C10 N7 C12 108.4(3) . . ?
C20 N8 C21 109.4(3) . . ?
C20 N8 C19 110.3(3) . . ?
C21 N8 C19 108.0(3) . . ?
C20 N8 C22 110.4(3) . . ?
C21 N8 C22 107.5(3) . . ?
C19 N8 C22 111.2(3) . . ?
C3 C1 C4 117.5(3) . . ?
C3 C1 C2 122.4(3) . . ?
C4 C1 C2 119.9(3) . . ?
O1 C2 N1 120.0(4) . . ?
O1 C2 C1 121.3(3) . . ?
N1 C2 C1 118.7(3) . . ?
N2 C3 C1 179.1(4) . . ?
N3 C4 C1 177.9(4) . . ?
C8 C5 C7 116.7(3) . . ?
C8 C5 C6 120.5(3) . . ?
C7 C5 C6 122.7(3) . . ?
O2 C6 N4 120.1(3) . . ?
O2 C6 C5 121.1(3) . . ?
N4 C6 C5 118.8(3) . . ?
N5 C7 C5 178.9(4) . . ?
N6 C8 C5 177.5(5) . . ?
N7 C9 H9A 109.5 . . ?
N7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N7 C10 H10A 109.5 . . ?
N7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N7 C11 H11A 109.5 . . ?
N7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N7 114.4(3) . . ?
C13 C12 H12A 108.7 . . ?
N7 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
N7 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C18 C13 C14 119.9(4) . . ?
C18 C13 C12 119.7(4) . . ?
C14 C13 C12 120.4(3) . . ?
C13 C14 C15 119.3(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.5(4) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 120.1(4) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
N8 C19 H19A 109.5 . . ?
N8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C21 H21A 109.5 . . ?
N8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 N8 116.0(3) . . ?
C23 C22 H22A 108.3 . . ?
N8 C22 H22A 108.3 . . ?
C23 C22 H22B 108.3 . . ?
N8 C22 H22B 108.3 . . ?
H22A C22 H22B 107.4 . . ?
C28 C23 C24 118.4(3) . . ?
C28 C23 C22 118.9(3) . . ?
C24 C23 C22 122.5(3) . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.8(4) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.0(4) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 119.2(4) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C23 C28 C27 121.2(4) . . ?
C23 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4B O1 0.93(4) 1.99(4) 2.906(4) 167(4) 1_655
N4 H4A N2 0.86(4) 2.22(4) 3.045(5) 160(3) .
N1 H1B O2 0.82(4) 2.09(5) 2.909(5) 174(4) 1_455
N1 H1A N5 0.85(4) 2.24(4) 3.047(5) 157(4) .

_diffrn_measured_fraction_theta_max 0.870
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.870
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.052


