#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009104.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2009104
loop_
_publ_author_name
'Soumhi, E. H.'
'Saadoune, I.'
'Driss, A.'
'Jouini, T.'
_publ_section_title
;
 Tetrakis(cyclopropylammonium) cyclotetraphosphate tetrahydrate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1932
_journal_page_last               1934
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         '4C3 H8 N1 1+, P4 O12 4-, 4H2 O'
_chemical_formula_sum            'C12 H40 N4 O16 P4'
_chemical_formula_weight         620.36
_chemical_name_systematic
;
 'Tetrakis(Cyclopropylammonium)Cyclotetraphosphate Tetrahydrate'
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.045(2)
_cell_length_b                   18.037(2)
_cell_length_c                   10.0560(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      10.5
_cell_volume                     1440.1(4)
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_collection
'CAD4 EXPRESS (Duisenberg, 1992; Mac\'i\<cek & Yordanov, 1992)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1990)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'CAD4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0084
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3356
_diffrn_reflns_theta_full        26.97
_diffrn_reflns_theta_max         26.97
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        5.2
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type
'empirical correction by \y scans (North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.405
_refine_ls_extinction_coef       0.030(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0446P)^2^+0.7448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         0.0906
_reflns_number_gt                2729
_reflns_number_total             3132
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    cf1294.cif
_[local]_cod_data_source_block   global
_[local]_cod_cif_authors_sg_H-M  'P 21/a'
_cod_database_code               2009104
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
P1 0.03168(5) 0.52363(2) 0.21657(4) 0.0257(2) Uani d 1 P
P2 0.10683(5) 0.59553(2) -0.02947(4) 0.0239(2) Uani d 1 P
O11 -0.1287(2) 0.53115(7) 0.2696(2) 0.0383(3) Uani d 1 O
O21 0.1929(2) 0.52431(7) 0.3114(2) 0.0401(3) Uani d 1 O
O12 0.0872(2) 0.67415(7) -0.0704(2) 0.0353(3) Uani d 1 O
O22 0.2722(2) 0.55800(7) -0.0178(2) 0.0380(3) Uani d 1 O
OL12 0.0315(2) 0.58899(6) 0.1083(2) 0.0319(3) Uani d 1 O
OL21 0.0343(2) 0.45014(6) 0.1281(2) 0.0280(3) Uani d 1 O
OW1 0.2313(2) 0.80435(8) -0.1278(2) 0.0495(4) Uani d 1 O
OW2 0.3958(2) 0.4002(2) 0.3404(3) 0.0787(7) Uani d 1 O
N1 0.2662(2) 0.57090(10) 0.5790(2) 0.0366(3) Uani d 1 N
N2 0.6063(2) 0.59940(10) 0.0669(2) 0.0425(4) Uani d 1 N
C1 0.1874(3) 0.6402(2) 0.6105(2) 0.0478(5) Uani d 1 C
C2 0.1556(5) 0.6979(2) 0.5060(4) 0.0777(9) Uani d 1 C
C3 0.0134(4) 0.6554(2) 0.5465(4) 0.0796(9) Uani d 1 C
C4 0.6191(3) 0.6520(2) 0.1794(2) 0.0496(5) Uani d 1 C
C5 0.4834(4) 0.7061(2) 0.1811(3) 0.0646(7) Uani d 1 C
C6 0.5063(4) 0.6438(2) 0.2784(3) 0.0716(8) Uani d 1 C
H1W1 0.200(3) 0.760(2) -0.111(3) 0.061(8) Uiso d 1 H
H2W1 0.335(5) 0.800(2) -0.116(3) 0.09(2) Uiso d 1 H
H1W2 0.338(6) 0.443(3) 0.310(5) 0.14(2) Uiso d 1 H
H2W2 0.366(4) 0.369(2) 0.279(4) 0.10(2) Uiso d 1 H
H1N1 0.240(3) 0.557(2) 0.492(2) 0.041(6) Uiso d 1 H
H2N1 0.227(3) 0.532(2) 0.628(3) 0.058(7) Uiso d 1 H
H3N1 0.373(4) 0.575(2) 0.603(3) 0.065(8) Uiso d 1 H
H1N2 0.643(3) 0.620(2) -0.004(3) 0.060(8) Uiso d 1 H
H2N2 0.670(3) 0.560(2) 0.092(3) 0.058(7) Uiso d 1 H
H3N2 0.504(4) 0.586(2) 0.040(3) 0.057(7) Uiso d 1 H
HC1 0.225(3) 0.657(2) 0.705(2) 0.053(6) Uiso d 1 H
H1C2 0.198(4) 0.684(2) 0.424(3) 0.068(8) Uiso d 1 H
H2C2 0.172(5) 0.753(3) 0.531(4) 0.14(2) Uiso d 1 H
H1C3 -0.038(4) 0.622(2) 0.482(4) 0.09(2) Uiso d 1 H
H2C3 -0.056(5) 0.676(2) 0.606(4) 0.12(2) Uiso d 1 H
HC4 0.733(4) 0.668(2) 0.213(3) 0.083(9) Uiso d 1 H
H1C5 0.520(4) 0.757(2) 0.213(3) 0.10(2) Uiso d 1 H
H2C5 0.387(4) 0.703(2) 0.104(3) 0.085(9) Uiso d 1 H
H1C6 0.439(4) 0.600(2) 0.267(3) 0.065(8) Uiso d 1 H
H2C6 0.559(4) 0.651(2) 0.365(3) 0.080(9) Uiso d 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
P1 0.0279(2) 0.0249(2) 0.0237(2) -0.0002(2) 0.0029(2) -0.0006(2)
P2 0.0209(2) 0.0216(2) 0.0290(2) -0.0024(2) 0.0038(2) 0.0002(2)
O11 0.0407(7) 0.0374(7) 0.0407(7) 0.0031(5) 0.0182(6) 0.0021(5)
O21 0.0396(7) 0.0428(7) 0.0331(6) -0.0008(6) -0.0081(5) -0.0062(5)
O12 0.0411(7) 0.0227(6) 0.0428(7) -0.0066(5) 0.0091(5) 0.0031(5)
O22 0.0204(6) 0.0416(7) 0.0508(8) 0.0011(5) 0.0024(5) -0.0059(6)
OL12 0.0420(7) 0.0244(6) 0.0309(6) 0.0026(5) 0.0107(5) 0.0008(5)
OL21 0.0229(5) 0.0250(6) 0.0345(6) 0.0003(4) -0.0003(4) -0.0034(5)
OW1 0.0406(8) 0.0336(8) 0.073(2) -0.0085(6) 0.0052(7) 0.0122(7)
OW2 0.0460(10) 0.073(2) 0.106(2) 0.0144(9) -0.0210(10) -0.033(2)
N1 0.0365(9) 0.0441(9) 0.0289(8) -0.0038(7) 0.0043(6) 0.0008(7)
N2 0.0245(8) 0.0380(9) 0.064(2) 0.0013(7) 0.0035(8) 0.0042(8)
C1 0.055(2) 0.049(2) 0.039(2) 0.0010(10) 0.0065(9) -0.0061(9)
C2 0.102(3) 0.053(2) 0.076(2) 0.013(2) 0.008(2) 0.011(2)
C3 0.053(2) 0.081(2) 0.103(2) 0.020(2) 0.007(2) -0.022(2)
C4 0.0350(10) 0.044(2) 0.064(2) -0.0089(9) -0.0068(9) 0.0030(10)
C5 0.059(2) 0.054(2) 0.075(2) 0.006(2) -0.006(2) -0.017(2)
C6 0.075(2) 0.081(2) 0.059(2) -0.024(2) 0.010(2) -0.010(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P 0.1023 0.0942 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 P1 O21 . 119.42(8) y
O11 P1 OL21 . 111.52(7) y
O21 P1 OL21 . 106.07(7) y
O11 P1 OL12 . 105.75(7) y
O21 P1 OL12 . 109.64(8) y
OL21 P1 OL12 . 103.31(6) y
O12 P2 O22 . 121.00(8) y
O12 P2 OL12 . 105.83(7) y
O22 P2 OL12 . 110.97(7) y
O12 P2 OL21 3_565 106.66(7) y
O22 P2 OL21 3_565 110.52(7) y
OL12 P2 OL21 3_565 99.64(7) y
P2 OL12 P1 . 132.93(8) y
P1 OL21 P2 3_565 134.16(7) y
H1W1 OW1 H2W1 . 102(3) ?
H1W2 OW2 H2W2 . 104(4) ?
C1 N1 H1N1 . 114(2) ?
C1 N1 H2N1 . 109(2) ?
H1N1 N1 H2N1 . 105(2) ?
C1 N1 H3N1 . 109(2) ?
H1N1 N1 H3N1 . 111(2) ?
H2N1 N1 H3N1 . 109(2) ?
C4 N2 H1N2 . 111(2) ?
C4 N2 H2N2 . 110(2) ?
H1N2 N2 H2N2 . 108(2) ?
C4 N2 H3N2 . 112(2) ?
H1N2 N2 H3N2 . 107(2) ?
H2N2 N2 H3N2 . 110(2) ?
N1 C1 C3 . 118.8(2) ?
N1 C1 C2 . 118.8(2) ?
C3 C1 C2 . 60.7(2) ?
N1 C1 HC1 . 113(2) ?
C3 C1 HC1 . 119(2) ?
C2 C1 HC1 . 117(2) ?
C1 C2 C3 . 59.6(2) ?
C1 C2 H1C2 . 113(2) ?
C3 C2 H1C2 . 119(2) ?
C1 C2 H2C2 . 121(2) ?
C3 C2 H2C2 . 120(2) ?
H1C2 C2 H2C2 . 114(3) ?
C1 C3 C2 . 59.7(2) ?
C1 C3 H1C3 . 118(2) ?
C2 C3 H1C3 . 115(2) ?
C1 C3 H2C3 . 114(2) ?
C2 C3 H2C3 . 121(2) ?
H1C3 C3 H2C3 . 117(3) ?
C6 C4 C5 . 60.9(2) ?
C6 C4 N2 . 119.1(2) ?
C5 C4 N2 . 118.6(2) ?
C6 C4 HC4 . 117(2) ?
C5 C4 HC4 . 117(2) ?
N2 C4 HC4 . 114(2) ?
C4 C5 C6 . 59.3(2) ?
C4 C5 H1C5 . 116(2) ?
C6 C5 H1C5 . 119(2) ?
C4 C5 H2C5 . 116(2) ?
C6 C5 H2C5 . 118(2) ?
H1C5 C5 H2C5 . 117(3) ?
C4 C6 C5 . 59.8(2) ?
C4 C6 H1C6 . 114(2) ?
C5 C6 H1C6 . 123(2) ?
C4 C6 H2C6 . 113(2) ?
C5 C6 H2C6 . 120(2) ?
H1C6 C6 H2C6 . 114(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O11 . 1.479(2) y
P1 O21 . 1.481(2) y
P1 OL21 . 1.599(2) y
P1 OL12 . 1.604(2) y
P2 O12 . 1.478(2) y
P2 O22 . 1.480(2) y
P2 OL12 . 1.604(2) y
P2 OL21 3_565 1.609(2) y
OL21 P2 3_565 1.6085(11) ?
OW1 H1W1 . 0.86(3) ?
OW1 H2W1 . 0.83(4) ?
OW2 H1W2 . 0.92(5) ?
OW2 H2W2 . 0.85(4) ?
N1 C1 . 1.459(3) ?
N1 H1N1 . 0.90(2) ?
N1 H2N1 . 0.94(3) ?
N1 H3N1 . 0.86(3) ?
N2 C4 . 1.468(3) ?
N2 H1N2 . 0.90(3) ?
N2 H2N2 . 0.89(3) ?
N2 H3N2 . 0.86(3) ?
C1 C3 . 1.469(4) ?
C1 C2 . 1.472(4) ?
C1 HC1 . 0.99(2) ?
C2 C3 . 1.487(5) ?
C2 H1C2 . 0.97(3) ?
C2 H2C2 . 1.03(5) ?
C3 H1C3 . 0.93(4) ?
C3 H2C3 . 0.96(4) ?
C4 C6 . 1.459(4) ?
C4 C5 . 1.466(4) ?
C4 HC4 . 0.97(3) ?
C5 C6 . 1.482(4) ?
C5 H1C5 . 0.99(4) ?
C5 H2C5 . 1.01(3) ?
C6 H1C6 . 0.96(3) ?
C6 H2C6 . 0.91(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
OW1 H1W1 O12 . 0.86(3) 1.88(3) 2.722(2) 168(3)
OW1 H2W1 O12 4_675 0.83(4) 2.06(4) 2.855(2) 160(4)
OW2 H1W2 O21 . 0.92(5) 1.88(5) 2.758(3) 158(5)
OW2 H2W2 OW1 2_545 0.85(4) 1.97(4) 2.811(3) 172(4)
N1 H1N1 O21 . 0.90(2) 1.89(3) 2.790(2) 178(3)
N1 H2N1 O11 3_566 0.94(3) 1.81(3) 2.734(2) 171(3)
N1 H3N1 OW2 3_666 0.86(3) 1.91(3) 2.759(3) 170(3)
N2 H1N2 OW1 4_675 0.90(3) 2.05(3) 2.914(3) 162(3)
N2 H2N2 O11 1_655 0.89(3) 2.27(3) 2.969(2) 135(3)
N2 H2N2 O22 3_665 0.89(3) 2.32(3) 3.069(2) 141(3)
N2 H3N2 O22 . 0.86(3) 1.93(3) 2.787(2) 178(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
O12 P2 OL12 P1 . . -171.35(11)
O22 P2 OL12 P1 . . -38.34(13)
OL21 P2 OL12 P1 3_565 . 78.14(12)
O11 P1 OL12 P2 . . -147.25(11)
O21 P1 OL12 P2 . . 82.76(12)
OL21 P1 OL12 P2 . . -29.97(13)
O11 P1 OL21 P2 . 3_565 33.55(13)
O21 P1 OL21 P2 . 3_565 165.08(11)
OL12 P1 OL21 P2 . 3_565 -79.60(12)
N1 C1 C2 C3 . . 108.8(3)
N1 C1 C3 C2 . . -108.8(3)
N2 C4 C5 C6 . . 109.2(2)
N2 C4 C6 C5 . . -108.5(2)