#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/31/2223165.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_2223165
loop_
_publ_author_name
'Nazari, Mohammad'
'Abbasi, Alireza'
'Nemati Kharat, Ali'
'Hantehzadeh, Mohammad Reza'
_publ_section_title
;
 2-Aminopyridinium diphenylphosphinate monohydrate
;
_journal_coeditor_code           NG2622
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2300
_journal_paper_doi               10.1107/S1600536809033856
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C5 H7 N2 +, C12 H10 O2 P -, H2 O'
_chemical_formula_moiety         'C5 H7 N2 +, C12 H10 O2 P -, H2 O'
_chemical_formula_sum            'C17 H19 N2 O3 P'
_chemical_formula_weight         330.31
_chemical_name_systematic
;
2-Aminopyridinium diphenylphosphinate monohydrate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.073(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2716(19)
_cell_length_b                   9.979(2)
_cell_length_c                   11.7671(15)
_cell_measurement_reflns_used    8165
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.46
_cell_volume                     1746.8(5)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2007)'
_computing_data_collection       'X-RED (Stoe & Cie, 2007)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2001)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'φ oscillation'
_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  0.0970
_diffrn_reflns_av_sigmaI/netI    0.0854
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8165
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.46
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9652
_exptl_absorpt_correction_T_min  0.8134
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(X-SHAPE; Stoe & Cie, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2972
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0544
_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)+(0.05P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                1660
_reflns_number_total             2972
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2622.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Analytical' changed to
'analytical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Analytical' changed to
'analytical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223165
_cod_database_fobs_code          2223165
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_type_symbol
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.23381(6) 0.38907(9) 0.28738(7) 0.0566(3) Uani d . 1 . .
O O1 0.19470(14) 0.3089(2) 0.37261(18) 0.0684(6) Uani d . 1 . .
O O2 0.16905(13) 0.4311(2) 0.17762(16) 0.0679(6) Uani d . 1 . .
C C1 0.2857(2) 0.5359(3) 0.3623(3) 0.0549(8) Uani d . 1 . .
C C2 0.3479(2) 0.5264(4) 0.4676(3) 0.0719(10) Uani d . 1 . .
H H5 0.3656 0.4419 0.4975 0.086 Uiso calc R 1 . .
C C3 0.3843(3) 0.6372(4) 0.5292(3) 0.0856(11) Uani d . 1 . .
H H4 0.4262 0.6279 0.5997 0.103 Uiso calc R 1 . .
C C4 0.3587(3) 0.7608(5) 0.4863(4) 0.0922(12) Uani d . 1 . .
H H3 0.3829 0.8367 0.5275 0.111 Uiso calc R 1 . .
C C5 0.2982(3) 0.7738(4) 0.3836(4) 0.1035(14) Uani d . 1 . .
H H2 0.2805 0.8589 0.3552 0.124 Uiso calc R 1 . .
C C6 0.2622(3) 0.6628(4) 0.3205(3) 0.0831(11) Uani d . 1 . .
H H1 0.2217 0.6736 0.2491 0.100 Uiso calc R 1 . .
C C7 0.3262(2) 0.2968(3) 0.2542(3) 0.0544(8) Uani d . 1 . .
C C8 0.3694(2) 0.3417(3) 0.1706(3) 0.0674(9) Uani d . 1 . .
H H10 0.3487 0.4182 0.1278 0.081 Uiso calc R 1 . .
C C9 0.4430(2) 0.2742(4) 0.1497(3) 0.0769(10) Uani d . 1 . .
H H9 0.4715 0.3062 0.0933 0.092 Uiso calc R 1 . .
C C10 0.4746(2) 0.1605(4) 0.2111(4) 0.0815(11) Uani d . 1 . .
H H8 0.5247 0.1159 0.1974 0.098 Uiso calc R 1 . .
C C11 0.4311(3) 0.1143(4) 0.2928(3) 0.0859(11) Uani d . 1 . .
H H7 0.4514 0.0367 0.3343 0.103 Uiso calc R 1 . .
C C12 0.3575(2) 0.1808(3) 0.3147(3) 0.0728(10) Uani d . 1 . .
H H6 0.3287 0.1477 0.3705 0.087 Uiso calc R 1 . .
N N1 0.02673(18) 0.3481(3) 0.3918(2) 0.0648(7) Uani d . 1 . .
H H1A 0.0801 0.3370 0.3811 0.078 Uiso calc R 1 . .
N N2 -0.00790(19) 0.4687(3) 0.2200(2) 0.0800(9) Uani d . 1 . .
H H13 0.0456 0.4558 0.2105 0.096 Uiso d R 1 . .
H H14 -0.0458 0.5142 0.1695 0.096 Uiso d R 1 . .
C C13 -0.0324(2) 0.4193(3) 0.3131(3) 0.0638(9) Uani d . 1 . .
C C14 -0.1181(2) 0.4384(4) 0.3339(3) 0.0765(10) Uani d . 1 . .
H H18 -0.1605 0.4888 0.2822 0.092 Uiso calc R 1 . .
C C15 -0.1392(3) 0.3836(4) 0.4294(4) 0.0877(12) Uani d . 1 . .
H H17 -0.1963 0.3965 0.4430 0.105 Uiso calc R 1 . .
C C16 -0.0765(3) 0.3082(4) 0.5071(4) 0.0874(12) Uani d . 1 . .
H H16 -0.0914 0.2690 0.5719 0.105 Uiso calc R 1 . .
C C17 0.0058(3) 0.2930(4) 0.4874(3) 0.0789(10) Uani d . 1 . .
H H15 0.0489 0.2442 0.5397 0.095 Uiso calc R 1 . .
O O3 0.16544(17) 0.0543(2) 0.44385(19) 0.0746(7) Uani d D 1 . .
H H3A 0.163(2) 0.059(3) 0.5239(12) 0.090 Uiso d D 1 . .
H H3B 0.181(2) 0.1430(16) 0.426(3) 0.090 Uiso d D 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 P1 O1 . . 116.01(13) ?
O2 P1 C1 . . 109.03(14) ?
O1 P1 C1 . . 107.64(13) ?
O2 P1 C7 . . 110.68(13) ?
O1 P1 C7 . . 108.71(14) ?
C1 P1 C7 . . 104.06(14) ?
C6 C1 C2 . . 117.0(3) ?
C6 C1 P1 . . 121.6(3) ?
C2 C1 P1 . . 121.3(2) ?
C3 C2 C1 . . 122.2(3) ?
C3 C2 H5 . . 118.9 ?
C1 C2 H5 . . 118.9 ?
C4 C3 C2 . . 119.3(4) ?
C4 C3 H4 . . 120.4 ?
C2 C3 H4 . . 120.4 ?
C5 C4 C3 . . 120.1(4) ?
C5 C4 H3 . . 119.9 ?
C3 C4 H3 . . 119.9 ?
C4 C5 C6 . . 120.9(4) ?
C4 C5 H2 . . 119.5 ?
C6 C5 H2 . . 119.5 ?
C1 C6 C5 . . 120.5(4) ?
C1 C6 H1 . . 119.8 ?
C5 C6 H1 . . 119.8 ?
C8 C7 C12 . . 118.3(3) ?
C8 C7 P1 . . 120.9(2) ?
C12 C7 P1 . . 120.8(2) ?
C7 C8 C9 . . 120.6(3) ?
C7 C8 H10 . . 119.7 ?
C9 C8 H10 . . 119.7 ?
C10 C9 C8 . . 120.9(4) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C11 C10 C9 . . 118.7(3) ?
C11 C10 H8 . . 120.7 ?
C9 C10 H8 . . 120.7 ?
C10 C11 C12 . . 121.1(4) ?
C10 C11 H7 . . 119.5 ?
C12 C11 H7 . . 119.5 ?
C11 C12 C7 . . 120.4(3) ?
C11 C12 H6 . . 119.8 ?
C7 C12 H6 . . 119.8 ?
C13 N1 C17 . . 122.7(3) ?
C13 N1 H1A . . 118.7 ?
C17 N1 H1A . . 118.7 ?
C13 N2 H13 . . 120.3 ?
C13 N2 H14 . . 119.7 ?
H13 N2 H14 . . 120.0 ?
N2 C13 N1 . . 119.7(3) ?
N2 C13 C14 . . 122.9(3) ?
N1 C13 C14 . . 117.5(3) ?
C15 C14 C13 . . 120.0(4) ?
C15 C14 H18 . . 120.0 ?
C13 C14 H18 . . 120.0 ?
C14 C15 C16 . . 120.5(4) ?
C14 C15 H17 . . 119.7 ?
C16 C15 H17 . . 119.7 ?
C17 C16 C15 . . 118.9(4) ?
C17 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C16 C17 N1 . . 120.4(4) ?
C16 C17 H15 . . 119.8 ?
N1 C17 H15 . . 119.8 ?
H3A O3 H3B . . 104(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 O2 . 1.498(2) ?
P1 O1 . 1.508(2) ?
P1 C1 . 1.800(3) ?
P1 C7 . 1.801(3) ?
C1 C6 . 1.376(4) ?
C1 C2 . 1.383(4) ?
C2 C3 . 1.370(5) ?
C2 H5 . 0.9300 ?
C3 C4 . 1.356(5) ?
C3 H4 . 0.9300 ?
C4 C5 . 1.351(5) ?
C4 H3 . 0.9300 ?
C5 C6 . 1.376(5) ?
C5 H2 . 0.9300 ?
C6 H1 . 0.9300 ?
C7 C8 . 1.377(4) ?
C7 C12 . 1.386(4) ?
C8 C9 . 1.379(5) ?
C8 H10 . 0.9300 ?
C9 C10 . 1.373(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.367(5) ?
C10 H8 . 0.9300 ?
C11 C12 . 1.379(5) ?
C11 H7 . 0.9300 ?
C12 H6 . 0.9300 ?
N1 C13 . 1.341(4) ?
N1 C17 . 1.355(4) ?
N1 H1A . 0.8600 ?
N2 C13 . 1.329(4) ?
N2 H13 . 0.8601 ?
N2 H14 . 0.8600 ?
C13 C14 . 1.398(4) ?
C14 C15 . 1.353(5) ?
C14 H18 . 0.9300 ?
C15 C16 . 1.387(5) ?
C15 H17 . 0.9300 ?
C16 C17 . 1.337(5) ?
C16 H16 . 0.9300 ?
C17 H15 . 0.9300 ?
O3 H3A . 0.954(10) ?
O3 H3B . 0.953(10) ?
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
_geom_hbond_publ_flag
N1 H1A O1 . 0.86 1.80 2.655(4) 175 yes
O3 H3A O2 4_566 0.95(2) 1.79(2) 2.743(3) 175(3) yes
O3 H3B O1 . 0.95(2) 1.80(2) 2.744(3) 171(3) yes
N2 H13 O2 . 0.86 2.02 2.881(4) 176 yes
N2 H14 O3 2_555 0.86 2.04 2.853(4) 157 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655861
