#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/21/2102150.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_2102150
loop_
_publ_author_name
'Fábry, Jan'
'Petrícek, Václav'
'Kroupa, Jan'
'Císarová, Ivana'
_publ_section_title
;
 Ferroelastic structures of n-pentyl-, n- hexyl- and
 n-nonylammonium dihydrogenphosphate crystals
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              906
_journal_page_last               914
_journal_paper_doi               10.1107/S0108768100007941
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C6 H16 N +,H2 O4 P -'
_chemical_formula_structural     '(C6 H13 N H3) (H2 P O4)'
_chemical_formula_sum            'C6 H18 N O4 P'
_chemical_formula_weight         199.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.1430(10)
_cell_length_b                   29.637(8)
_cell_length_c                   7.2990(10)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      22.8
_cell_measurement_theta_min      5.6
_cell_volume                     1977.6(6)
_computing_cell_refinement       'HW, Petříček, 1998'
_computing_data_collection       'HW, Petříček, 1998'
_computing_data_reduction        'JANA98, Petříček & Dušek, 1998'
_computing_molecular_graphics    'PICTUR (Dušek, 1993)'
_computing_publication_material  'JANA98, Petříček & Dušek, 1998'
_computing_structure_refinement  'JANA98, Petříček & Dušek, 1998'
_computing_structure_solution    'SHELXS-86, Sheldrick, 1986'
_diffrn_measurement_device       'Hilger & Watts                '
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0601
_diffrn_reflns_av_sigmaI/netI    .0461
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5446
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        6.0
_diffrn_standards_interval_count 30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .259
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          .33
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .10
_refine_diff_density_max         .46
_refine_diff_density_min         -.54
_refine_ls_extinction_coef       .00017(2)
_refine_ls_extinction_method     'Becker & Coppens, 1974, type II'
_refine_ls_goodness_of_fit_all   1.71
_refine_ls_goodness_of_fit_obs   1.99
_refine_ls_goodness_of_fit_ref   1.71
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           fullcycle
_refine_ls_number_constraints    0
_refine_ls_number_parameters     363
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     4
_refine_ls_R_factor_gt           .0499
_refine_ls_shift/su_max          .01
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=(σ²(Fₒ)+0.0001(Fₒ)²)⁻¹
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0556
_reflns_number_gt                2167
_reflns_number_total             3452
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            na0106.cif
_cod_data_source_block           C6ADP
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value
'w=(\s^2^(F~o~)+0.0001(F~o~)^2^)^-1^' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w=(\s^2^(F~o~)+0.0001(F~o~)^2^)^-1^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1977.7(7)
_cod_database_code               2102150
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_type_symbol
P1 .08787(7) .30071(2) .25532(9) .0232(2) Uani 1 P
O11 -.0327(2) .33731(6) .2298(3) .0368(7) Uani 1 O
O21 .1194(2) .29233(6) .4548(2) .0335(6) Uani 1 O
O31 .2159(2) .31489(6) .1415(2) .0324(6) Uani 1 O
O41 .0230(2) .25539(6) .1804(3) .0334(6) Uani 1 O
P2 .58373(7) .29784(2) .26410(9) .0236(2) Uani 1 P
O12 .4712(2) .33714(6) .2666(3) .0371(7) Uani 1 O
O22 .6176(2) .28995(7) .0574(2) .0379(7) Uani 1 O
O32 .7172(2) .31308(7) .3665(2) .0344(6) Uani 1 O
O42 .5179(2) .25485(6) .3389(2) .0302(6) Uani 1 O
N1 .1904(3) .69309(9) .2676(4) .0307(8) Uani 1 N
C11 .1059(3) .65055(9) .2485(4) .0315(9) Uani 1 C
C21 .2023(3) .60953(9) .2565(5) .0350(10) Uani 1 C
C31 .1128(3) .56660(10) .2502(5) .0380(10) Uani 1 C
C41 .2032(4) .52360(10) .2529(5) .0380(10) Uani 1 C
C51 .1132(4) .48070(10) .2502(6) .0480(10) Uani 1 C
C61 .2029(6) .43810(10) .2539(6) .058(2) Uani 1 C
N2 .6999(3) .69255(8) .2263(4) .0306(8) Uani 1 N
C12 .6110(3) .65082(9) .2444(4) .0316(9) Uani 1 C
C22 .7048(3) .60921(9) .2425(4) .0334(9) Uani 1 C
C32 .6133(3) .56635(9) .2489(5) .0390(10) Uani 1 C
C42 .7031(4) .52360(10) .2468(5) .0390(10) Uani 1 C
C52 .6126(4) .48060(10) .2489(6) .0480(10) Uani 1 C
C62 .7008(6) .43800(10) .2467(6) .060(2) Uani 1 C
H1N2 .760(3) .6910(10) .302(4) .036(9) Uiso 1 H
H2N2 .642(3) .7182(9) .241(3) .022(7) Uiso 1 H
H3N2 .741(3) .6918(9) .107(4) .042(9) Uiso 1 H
H1C12 .564(3) .6557(9) .349(4) .034(8) Uiso 1 H
H2C12 .540(3) .6499(8) .143(4) .029(7) Uiso 1 H
H1C22 .777(4) .6080(10) .114(5) .060(10) Uiso 1 H
H2C22 .775(3) .6078(8) .344(4) .033(7) Uiso 1 H
H1C32 .548(4) .5670(10) .365(5) .060(10) Uiso 1 H
H2C32 .553(3) .5672(9) .150(4) .041(9) Uiso 1 H
H1C42 .755(3) .5232(9) .137(5) .040(9) Uiso 1 H
H2C42 .769(4) .5230(10) .350(5) .060(10) Uiso 1 H
H1C52 .540(4) .4820(10) .150(5) .060(10) Uiso 1 H
H2C52 .549(4) .4810(10) .360(6) .080(10) Uiso 1 H
H1C62 .775(5) .4370(10) .342(6) .090(10) Uiso 1 H
H2C62 .639(4) .4130(10) .242(5) .080(10) Uiso 1 H
H3C62 .760(4) .4370(10) .133(6) .080(10) Uiso 1 H
H1N1 .233(3) .6935(9) .383(4) .036(8) Uiso 1 H
H2N1 .128(4) .7160(10) .255(4) .048(9) Uiso 1 H
H3N1 .257(4) .6920(10) .200(4) .040(10) Uiso 1 H
H2C11 .050(4) .6530(10) .137(5) .057(9) Uiso 1 H
H1C11 .031(4) .6510(10) .337(5) .050(10) Uiso 1 H
H1C21 .269(3) .6100(10) .162(4) .047(9) Uiso 1 H
H2C21 .266(4) .6100(10) .379(5) .060(10) Uiso 1 H
H1C31 .052(3) .5656(9) .344(4) .035(9) Uiso 1 H
H2C31 .058(3) .5663(9) .144(4) .035(8) Uiso 1 H
H1C41 .270(4) .5210(10) .157(6) .070(10) Uiso 1 H
H2C41 .270(3) .5229(9) .371(5) .048(9) Uiso 1 H
H1C51 .047(4) .4830(10) .139(5) .070(10) Uiso 1 H
H2C51 .059(3) .4819(9) .359(4) .030(8) Uiso 1 H
H1C61 .262(4) .4340(10) .364(6) .070(10) Uiso 1 H
H2C61 .140(5) .416(2) .246(6) .090(10) Uiso 1 H
H3C61 .259(6) .437(2) .154(7) .11(2) Uiso 1 H
HO11 -.117(2) .3290(10) .257(4) .050(10) Uiso 1 H
HO41 .017(3) .2530(10) .0650(10) .060(10) Uiso 1 H
HO12 .391(2) .3270(10) .224(4) .050(10) Uiso 1 H
HO22 .606(3) .2624(4) .027(4) .041(9) Uiso 1 H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P .090 .095 International_Tables_vol_IV_Table_2.2A_and_2.3.1
O .008 .006 International_Tables_vol_IV_Table_2.2A_and_2.3.1
N .004 .003 International_Tables_vol_IV_Table_2.2A_and_2.3.1
C .002 .002 International_Tables_vol_IV_Table_2.2A_and_2.3.1
H .000 .000 International_Tables_vol_IV_Table_2.2A_and_2.3.1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O11 P1 O21 1_555 1_555 1_555 110.91(11) no
O11 P1 O31 1_555 1_555 1_555 107.13(11) no
O11 P1 O41 1_555 1_555 1_555 107.01(10) no
O21 P1 O31 1_555 1_555 1_555 116.25(10) no
O21 P1 O41 1_555 1_555 1_555 105.27(10) no
O31 P1 O41 1_555 1_555 1_555 109.93(10) no
O12 P2 O22 1_555 1_555 1_555 105.34(11) no
O12 P2 O32 1_555 1_555 1_555 107.69(11) no
O12 P2 O42 1_555 1_555 1_555 111.07(10) no
O22 P2 O32 1_555 1_555 1_555 110.89(11) no
O22 P2 O42 1_555 1_555 1_555 107.93(10) no
O32 P2 O42 1_555 1_555 1_555 113.62(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O11 1_555 1_555 1.556(3) yes
P1 O21 1_555 1_555 1.501(3) yes
P1 O31 1_555 1_555 1.505(3) yes
P1 O41 1_555 1_555 1.563(3) yes
O11 HO11 1_555 1_555 .84(2) yes
O41 HO41 1_555 1_555 .850(10) yes
P2 O12 1_555 1_555 1.554(2) yes
P2 O22 1_555 1_555 1.563(2) yes
P2 O32 1_555 1_555 1.492(2) yes
P2 O42 1_555 1_555 1.515(2) yes
O12 HO12 1_555 1_555 .85(2) no
O22 HO22 1_555 1_555 .850(10) no
N11 C11 1_555 1_555 1.484(4) yes
C11 C21 1_555 1_555 1.501(4) yes
C21 C31 1_555 1_555 1.514(5) yes
C31 C41 1_555 1_555 1.519(5) yes
C41 C51 1_555 1_555 1.515(5) yes
C51 C61 1_555 1_555 1.505(6) yes
N12 C12 1_555 1_555 1.486(4) yes
C12 C22 1_555 1_555 1.501(4) yes
C22 C32 1_555 1_555 1.523(4) yes
C32 C42 1_555 1_555 1.509(5) yes
C42 C52 1_555 1_555 1.521(5) yes
C52 C62 1_555 1_555 1.495(6) yes
O11 O32 1_555 1_455 2.610(3) yes
O21 O22 1_555 4_455 2.550(3) yes
O31 O12 1_555 1_555 2.579(3) yes
O41 O42 1_555 4_454 2.511(3) yes
O21 N2 1_555 2_666 2.870(3) yes
O31 N2 1_555 2_665 2.813(3) yes
O41 N2 1_555 3_545 2.850(3) yes
O22 N1 1_555 2_665 3.014(3) yes
O32 N1 1_555 2_666 2.796(3) yes
O42 N1 1_555 3_545 2.746(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O11 HO11 O32 1_555 1_555 1_455 .84(2) 2.610(3) 167(3) yes
O41 HO41 O42 1_555 1_555 4_454 .850(10) 2.511(3) 174(3) yes
O22 HO22 O21 1_555 1_555 4_554 .850(10) 2.551(3) 168(3) yes
O12 HO12 O31 1_555 1_555 1_555 .85(2) 2.580(3) 172(3) yes
N1 H1N1 O32 1_555 1_555 2_666 .92(3) 2.796(3) 167(3) yes
N1 H2N1 O42 1_555 1_555 3_555 .88(3) 2.746(3) 163(3) yes
N1 H3N1 O22 1_555 1_555 2_665 .79(3) 3.014(3) 155(3) yes
N2 H1N2 O21 1_555 1_555 2_666 .78(3) 2.870(3) 159(3) yes
N2 H2N2 O41 1_555 1_555 3_555 .93(3) 2.850(3) 158(2) yes
N2 H3N2 O31 1_555 1_555 2_665 .95(4) 2.813(3) 168(3) yes
