#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:15:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180419 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/88/7208802.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7208802
loop_
_publ_author_name
'Turner, David R.'
'Edwards, Alison J.'
'Piltz, Ross O.'
_publ_section_title
;
 Nitrile groups as hydrogen-bond acceptors in a donor-rich
 hydrogen-bonding network
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              6447
_journal_paper_doi               10.1039/c2ce26052b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C H6 N3, C4 H2 N3 O'
_chemical_formula_sum            'C5 H8 N6 O'
_chemical_formula_weight         168.16
_chemical_name_common            'Guanidinium Carbamoyldicyanomethanide'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.158(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8489(7)
_cell_length_b                   4.9807(4)
_cell_length_c                   18.7046(16)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    123(2)
_cell_volume                     811.46(11)
_computing_cell_refinement       'not applicable'
_computing_data_collection
;
MAATEL software for control of the instrument KOALA
;
_computing_data_reduction
;
LAUE1234 (Piltz R.O. 2011)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.814
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measurement_device_type  'KOALA Laue '
_diffrn_measurement_method       Laue
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'OPAL nuclear reactor'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.8-1.6
_diffrn_reflns_av_R_equivalents  0.1143
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12844
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         4.63
_exptl_absorpt_coefficient_mu    none
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             261
_exptl_crystal_size_max          1.20
_exptl_crystal_size_mid          1.00
_exptl_crystal_size_min          1.00
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.1958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0579
_reflns_number_gt                1130
_reflns_number_total             1361
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26052b.txt
_cod_data_source_block           guanN
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7208802
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'
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
O1 O 0.06461(18) 0.7413(3) 0.07432(8) 0.0279(3) Uani 1 1 d
N1 N 0.20599(13) 0.44670(18) 0.02226(5) 0.0256(2) Uani 1 1 d
N2 N 0.59109(11) 0.55064(19) 0.09894(5) 0.0300(2) Uani 1 1 d
N3 N 0.31322(13) 1.15171(19) 0.19581(5) 0.0331(2) Uani 1 1 d
N4 N -0.13393(12) 1.14888(19) 0.11551(5) 0.0286(2) Uani 1 1 d
N5 N -0.08766(11) 0.80257(18) 0.19738(5) 0.0252(2) Uani 1 1 d
N6 N -0.28338(11) 1.10115(18) 0.20388(5) 0.0256(2) Uani 1 1 d
C1 C 0.33264(15) 0.7656(2) 0.10786(6) 0.0201(3) Uani 1 1 d
C2 C 0.47568(14) 0.6533(2) 0.10407(6) 0.0219(3) Uani 1 1 d
C3 C 0.32225(16) 0.9783(2) 0.15552(6) 0.0221(3) Uani 1 1 d
C4 C 0.19395(13) 0.6519(2) 0.06758(5) 0.0196(2) Uani 1 1 d
C5 C -0.17033(14) 1.0164(2) 0.17150(6) 0.0189(3) Uani 1 1 d
H1 H 0.1089(3) 0.3696(5) -0.00763(13) 0.0354(6) Uani 1 1 d
H2 H -0.1267(4) 0.6869(6) 0.23421(16) 0.0445(7) Uani 1 1 d
H3 H -0.3460(4) 1.2598(5) 0.18371(16) 0.0423(7) Uani 1 1 d
H4 H -0.0500(4) 1.0737(6) 0.09108(15) 0.0433(6) Uani 1 1 d
H5 H -0.0153(4) 0.7255(5) 0.16655(15) 0.0396(6) Uani 1 1 d
H6 H -0.3131(4) 0.9883(5) 0.24377(15) 0.0422(6) Uani 1 1 d
H7 H -0.1999(4) 1.3024(6) 0.09431(15) 0.0450(7) Uani 1 1 d
H8 H 0.3071(4) 0.3837(6) 0.01315(16) 0.0460(7) Uani 1 1 d
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
H 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 -3.7409
'Neutron Data Booklet 2nd Ed July 2003, ILL Table 1.1'
C 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 6.6484
'Neutron Data Booklet 2nd Ed July 2003, ILL Table 1.1'
N 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 9.3600
'Neutron Data Booklet 2nd Ed July 2003, ILL Table 1.1'
O 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 0.0000 5.8050
'Neutron Data Booklet 2nd Ed July 2003, ILL Table 1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 N1 H1 118.82(18)
C4 N1 H8 121.58(19)
H1 N1 H8 119.2(2)
C5 N4 H4 118.28(18)
C5 N4 H7 119.2(2)
H4 N4 H7 121.9(2)
C5 N5 H2 118.29(19)
C5 N5 H5 117.31(17)
H2 N5 H5 120.2(2)
C5 N6 H3 119.42(19)
C5 N6 H6 118.57(19)
H3 N6 H6 121.4(3)
C2 C1 C3 119.85(11)
C2 C1 C4 120.86(10)
C3 C1 C4 119.10(11)
N2 C2 C1 176.86(12)
N3 C3 C1 178.96(13)
O1 C4 N1 120.54(12)
O1 C4 C1 121.14(11)
N1 C4 C1 118.32(10)
N6 C5 N4 120.71(10)
N6 C5 N5 119.86(10)
N4 C5 N5 119.37(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.2548(19)
N1 C4 1.3441(14)
N1 H1 1.014(3)
N1 H8 0.991(4)
N2 C2 1.1611(15)
N3 C3 1.1583(14)
N4 C5 1.3246(14)
N4 H4 1.010(3)
N4 H7 1.001(3)
N5 C5 1.3338(14)
N5 H2 1.005(3)
N5 H5 1.010(3)
N6 C5 1.3265(15)
N6 H3 1.000(3)
N6 H6 1.006(3)
C1 C2 1.3970(17)
C1 C3 1.3981(16)
C1 C4 1.4380(17)
