#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:54:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180454 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/23/7212328.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_7212328
loop_
_publ_author_name
'Fridrichová, Michaela'
'Němec, Ivan'
'Císařová, Ivana'
'Němec, Petr'
_publ_section_title
;
 Guanylurea(1+) hydrogen phosphite: a novel promising phase-matchable
 material for second harmonic generation
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2054
_journal_paper_doi               10.1039/b924973g
_journal_volume                  12
_journal_year                    2010
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C2 H7 N4 O, H2 O3 P'
_chemical_formula_sum            'C2 H9 N4 O4 P'
_chemical_formula_weight         184.10
_chemical_melting_point          452
_chemical_name_common            'guanylurea hydrogen phosphite'
_chemical_name_systematic
;
?
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2009-10-22 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.514(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6990(3)
_cell_length_b                   6.8420(2)
_cell_length_c                   16.3540(10)
_cell_measurement_reflns_used    879
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     744.74(6)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4256
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         4.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_preparation       'from water'
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.037(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1637
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0276
_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)+(0.0318P)²+0.2284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0679
_reflns_number_gt                1562
_reflns_number_total             1637
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b924973g.txt
_cod_data_source_block           guhp
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7212328
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'
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
P1 P 0.38935(6) 0.30842(6) 0.02427(3) 0.02872(15) Uani 1 1 d
C1 C 0.6435(3) 0.5165(3) 0.29518(12) 0.0283(4) Uani 1 1 d
C2 C 0.9071(3) 0.4481(3) 0.20798(13) 0.0316(4) Uani 1 1 d
N1 N 0.4481(3) 0.5173(3) 0.29902(15) 0.0404(4) Uani 1 1 d
N2 N 0.7688(3) 0.5658(3) 0.35947(12) 0.0375(4) Uani 1 1 d
N3 N 0.7065(2) 0.4613(2) 0.22281(11) 0.0306(3) Uani 1 1 d
N4 N 0.9347(3) 0.3695(3) 0.13587(13) 0.0393(4) Uani 1 1 d
O1 O 1.0441(2) 0.5058(3) 0.25826(12) 0.0461(4) Uani 1 1 d
O2 O 0.3764(2) 0.3773(2) 0.10988(9) 0.0372(3) Uani 1 1 d
O3 O 0.5948(2) 0.2643(2) 0.00032(10) 0.0404(4) Uani 1 1 d
O4 O 0.2873(3) 0.4575(3) -0.04066(11) 0.0534(5) Uani 1 1 d
H1 H 0.269(4) 0.165(3) 0.0125(15) 0.031(6) Uiso 1 1 d
H1A H 0.371(4) 0.490(4) 0.2619(17) 0.033(7) Uiso 1 1 d
H1B H 0.390(5) 0.545(5) 0.352(2) 0.066(10) Uiso 1 1 d
H2A H 0.722(4) 0.616(4) 0.408(2) 0.043(7) Uiso 1 1 d
H2B H 0.881(4) 0.556(3) 0.3525(16) 0.027(6) Uiso 1 1 d
H3 H 0.601(4) 0.424(4) 0.183(2) 0.053(8) Uiso 1 1 d
H4A H 1.063(6) 0.365(5) 0.131(2) 0.069(10) Uiso 1 1 d
H4B H 0.850(5) 0.338(4) 0.103(2) 0.044(7) Uiso 1 1 d
H4 H 0.205(6) 0.547(5) -0.025(2) 0.067(9) 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
P1 0.0279(2) 0.0329(2) 0.0257(2) -0.0015(2) 0.00462(15) 0.00472(19)
C1 0.0260(9) 0.0328(9) 0.0265(10) 0.0042(7) 0.0046(7) 0.0010(7)
C2 0.0259(9) 0.0343(9) 0.0348(11) 0.0012(7) 0.0048(8) 0.0022(7)
N1 0.0243(9) 0.0580(12) 0.0395(11) -0.0010(8) 0.0064(9) -0.0037(7)
N2 0.0285(9) 0.0570(11) 0.0270(9) -0.0050(8) 0.0035(7) -0.0003(8)
N3 0.0230(8) 0.0427(8) 0.0256(9) -0.0027(6) 0.0012(6) -0.0014(6)
N4 0.0324(10) 0.0521(11) 0.0341(11) -0.0071(8) 0.0064(8) 0.0027(8)
O1 0.0240(7) 0.0707(11) 0.0433(10) -0.0129(7) 0.0030(7) -0.0025(7)
O2 0.0335(7) 0.0509(8) 0.0274(7) -0.0071(6) 0.0042(6) 0.0043(6)
O3 0.0351(8) 0.0436(8) 0.0444(9) 0.0042(6) 0.0133(7) 0.0136(6)
O4 0.0688(12) 0.0604(10) 0.0327(9) 0.0062(7) 0.0125(8) 0.0391(9)
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 P1 O3 117.46(9)
O2 P1 O4 111.26(9)
O3 P1 O4 107.17(10)
O2 P1 H1 106.4(11)
O3 P1 H1 113.1(10)
O4 P1 H1 100.2(11)
N2 C1 N1 120.6(2)
N2 C1 N3 122.45(19)
N1 C1 N3 116.92(19)
O1 C2 N4 123.85(19)
O1 C2 N3 121.67(19)
N4 C2 N3 114.48(19)
C1 N1 H1A 122.7(19)
C1 N1 H1B 122(2)
H1A N1 H1B 115(3)
C1 N2 H2A 121.3(18)
C1 N2 H2B 113.7(19)
H2A N2 H2B 125(3)
C1 N3 C2 124.88(17)
C1 N3 H3 113.5(18)
C2 N3 H3 121.5(18)
C2 N4 H4A 109(2)
C2 N4 H4B 125(2)
H4A N4 H4B 126(3)
P1 O4 H4 119(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O2 1.4891(15)
P1 O3 1.5038(14)
P1 O4 1.5716(17)
P1 H1 1.27(2)
C1 N2 1.313(3)
C1 N1 1.317(3)
C1 N3 1.355(3)
C2 O1 1.226(3)
C2 N4 1.328(3)
C2 N3 1.395(2)
N1 H1A 0.77(3)
N1 H1B 1.00(4)
N2 H2A 0.95(3)
N2 H2B 0.78(3)
N3 H3 0.95(3)
N4 H4A 0.87(4)
N4 H4B 0.77(4)
O4 H4 0.88(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
N1 H1A O1 0.77(3) 2.19(3) 2.714(3) 126(2) 1_455
N1 H1A O2 0.77(3) 2.61(3) 3.222(3) 138(2) .
N1 H1B O4 1.00(4) 1.96(4) 2.951(3) 169(3) 2_565
N2 H2A O3 0.95(3) 2.00(3) 2.937(3) 173(3) 2_565
N2 H2B O1 0.78(3) 2.02(3) 2.646(3) 138(3) .
N3 H3 O2 0.95(3) 1.84(3) 2.776(2) 172(3) .
N4 H4A O2 0.87(4) 2.17(4) 3.037(3) 174(4) 1_655
N4 H4B O3 0.77(4) 2.31(4) 3.078(3) 176(3) .
O4 H4 O3 0.88(4) 1.73(4) 2.591(2) 165(3) 3_455
