#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225865.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_2225865
loop_
_publ_author_name
'Razzaq, Syed Naeem'
'Khan, Islam Ullah'
'Şahin, Onur'
'Büyükgüngör, Orhan'
_publ_section_title
;
 [1-(Carboxymethyl)cyclohexyl]methanaminium dihydrogen phosphate
;
_journal_coeditor_code           HB5398
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1074
_journal_paper_doi               10.1107/S1600536810012973
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H18 N O2 + , H2 O4 P -'
_chemical_formula_moiety         'C9 H18 N O2 + , H2 O4 P -'
_chemical_formula_sum            'C9 H20 N O6 P'
_chemical_formula_weight         269.23
_chemical_name_systematic
;
[1-(Carboxymethyl)cyclohexyl]methanaminium dihydrogen phosphate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.473(5)
_cell_length_b                   9.269(3)
_cell_length_c                   26.468(5)
_cell_measurement_reflns_used    1923
_cell_measurement_temperature    296
_cell_measurement_theta_max      21.59
_cell_measurement_theta_min      3.03
_cell_volume                     2569.4(16)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0708
_diffrn_reflns_av_sigmaI/netI    0.0741
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14659
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.452
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3185
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0514
_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)+(0.0712P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1546
_reflns_number_gt                1853
_reflns_number_total             3185
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5398.cif
_cod_data_source_block           I
_cod_database_code               2225865
_cod_database_fobs_code          2225865
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
C C1 0.6575(4) 0.1582(5) 0.67421(15) 0.0667(12) Uani d . 1 . .
H H1A 0.6569 0.2315 0.6481 0.080 Uiso calc R 1 . .
H H1B 0.7457 0.1334 0.6812 0.080 Uiso calc R 1 . .
C C2 0.5874(3) 0.0253(4) 0.65538(12) 0.0413(8) Uani d . 1 . .
H H2A 0.5967 -0.0514 0.6801 0.050 Uiso calc R 1 . .
H H2B 0.6266 -0.0070 0.6242 0.050 Uiso calc R 1 . .
C C3 0.4441(3) 0.0522(3) 0.64599(10) 0.0301(7) Uani d . 1 . .
C C4 0.3859(4) 0.1206(4) 0.69378(12) 0.0477(9) Uani d . 1 . .
H H4A 0.2983 0.1474 0.6866 0.057 Uiso calc R 1 . .
H H4B 0.3842 0.0485 0.7204 0.057 Uiso calc R 1 . .
C C5 0.4563(4) 0.2527(4) 0.71319(15) 0.0667(12) Uani d . 1 . .
H H5A 0.4489 0.3303 0.6888 0.080 Uiso calc R 1 . .
H H5B 0.4178 0.2847 0.7446 0.080 Uiso calc R 1 . .
C C6 0.5961(5) 0.2189(6) 0.72201(16) 0.0874(16) Uani d . 1 . .
H H6A 0.6039 0.1492 0.7492 0.105 Uiso calc R 1 . .
H H6B 0.6406 0.3061 0.7321 0.105 Uiso calc R 1 . .
C C7 0.4205(3) 0.1584(3) 0.60270(11) 0.0329(7) Uani d . 1 . .
H H7A 0.3293 0.1639 0.5966 0.040 Uiso calc R 1 . .
H H7B 0.4487 0.2533 0.6133 0.040 Uiso calc R 1 . .
C C8 0.3736(3) -0.0923(3) 0.63691(13) 0.0445(9) Uani d . 1 . .
H H8A 0.3624 -0.1395 0.6693 0.053 Uiso calc R 1 . .
H H8B 0.2891 -0.0705 0.6239 0.053 Uiso calc R 1 . .
C C9 0.4354(3) -0.1977(3) 0.60166(12) 0.0343(7) Uani d . 1 . .
N N1 0.4845(2) 0.1225(3) 0.55463(9) 0.0296(6) Uani d D 1 . .
H H3 0.5685(19) 0.141(4) 0.5561(14) 0.067(12) Uiso d D 1 . .
H H4 0.473(4) 0.027(2) 0.5469(13) 0.069(13) Uiso d D 1 . .
H H5 0.454(3) 0.173(4) 0.5291(11) 0.066(12) Uiso d D 1 . .
O O5 0.4571(2) -0.1736(2) 0.55742(8) 0.0417(6) Uani d . 1 . .
O O6 0.4610(3) -0.3214(3) 0.62334(10) 0.0537(7) Uani d D 1 . .
H H6 0.500(4) -0.373(4) 0.6027(13) 0.085(15) Uiso d D 1 . .
O O1 0.8667(2) 0.1053(2) 0.47674(8) 0.0366(5) Uani d D 1 . .
H H1 0.929(3) 0.066(4) 0.4646(16) 0.091(16) Uiso d D 1 . .
O O2 0.7236(2) -0.0726(2) 0.51893(10) 0.0413(6) Uani d D 1 . .
H H2 0.739(5) -0.149(3) 0.5316(16) 0.102(18) Uiso d D 1 . .
O O3 0.92807(17) -0.00007(19) 0.56151(7) 0.0279(5) Uani d . 1 . .
O O4 0.74292(18) 0.17523(19) 0.55177(8) 0.0324(5) Uani d . 1 . .
P P1 0.81774(6) 0.05253(7) 0.52950(3) 0.0242(2) Uani 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
C2 C1 C6 . . 111.5(3) ?
C2 C1 H1A . . 109.3 ?
C6 C1 H1A . . 109.3 ?
C2 C1 H1B . . 109.3 ?
C6 C1 H1B . . 109.3 ?
H1A C1 H1B . . 108.0 ?
C1 C2 C3 . . 113.1(3) ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2B . . 109.0 ?
C3 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
C7 C3 C2 . . 112.5(2) ?
C7 C3 C4 . . 106.6(2) ?
C2 C3 C4 . . 108.6(3) ?
C7 C3 C8 . . 111.3(3) ?
C2 C3 C8 . . 110.5(3) ?
C4 C3 C8 . . 107.1(2) ?
C5 C4 C3 . . 114.7(3) ?
C5 C4 H4A . . 108.6 ?
C3 C4 H4A . . 108.6 ?
C5 C4 H4B . . 108.6 ?
C3 C4 H4B . . 108.6 ?
H4A C4 H4B . . 107.6 ?
C6 C5 C4 . . 110.7(3) ?
C6 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
C6 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C5 C6 C1 . . 110.8(3) ?
C5 C6 H6A . . 109.5 ?
C1 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
C1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 108.1 ?
N1 C7 C3 . . 115.2(2) ?
N1 C7 H7A . . 108.5 ?
C3 C7 H7A . . 108.5 ?
N1 C7 H7B . . 108.5 ?
C3 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
C9 C8 C3 . . 117.0(2) ?
C9 C8 H8A . . 108.0 ?
C3 C8 H8A . . 108.0 ?
C9 C8 H8B . . 108.0 ?
C3 C8 H8B . . 108.0 ?
H8A C8 H8B . . 107.3 ?
O5 C9 O6 . . 123.0(3) ?
O5 C9 C8 . . 124.2(3) ?
O6 C9 C8 . . 112.7(3) ?
C7 N1 H3 . . 111(2) ?
C7 N1 H4 . . 111(2) ?
H3 N1 H4 . . 109(3) ?
C7 N1 H5 . . 112(2) ?
H3 N1 H5 . . 107(3) ?
H4 N1 H5 . . 107(3) ?
C9 O6 H6 . . 109(3) ?
P1 O1 H1 . . 118(3) ?
P1 O2 H2 . . 118(3) ?
O4 P1 O3 . . 115.00(12) n
O4 P1 O2 . . 107.84(12) n
O3 P1 O2 . . 110.23(12) n
O4 P1 O1 . . 106.50(11) n
O3 P1 O1 . . 110.49(12) n
O2 P1 O1 . . 106.35(14) n
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
C1 C2 . 1.519(5) ?
C1 C6 . 1.526(6) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C3 . 1.541(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C7 . 1.531(4) ?
C3 C4 . 1.541(4) ?
C3 C8 . 1.549(4) ?
C4 C5 . 1.519(5) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.515(6) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 N1 . 1.476(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.498(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O5 . 1.213(3) n
C9 O6 . 1.310(4) n
N1 H3 . 0.897(18) ?
N1 H4 . 0.912(18) ?
N1 H5 . 0.881(18) ?
O6 H6 . 0.83(4) ?
O1 P1 . 1.566(2) n
O1 H1 . 0.817(19) ?
O2 P1 . 1.548(2) n
O2 H2 . 0.799(19) ?
O3 P1 . 1.513(2) n
O4 P1 . 1.502(2) n
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
O6 H6 O3 7_755 0.83(4) 1.77(2) 2.602(3) 173(4)
O1 H1 O3 5_756 0.817(19) 1.76(2) 2.569(3) 173(5)
N1 H5 O1 3_456 0.881(18) 2.26(3) 2.929(4) 133(3)
N1 H5 O2 5_656 0.881(18) 2.44(3) 2.959(3) 118(3)
N1 H5 O5 5_656 0.881(18) 2.47(3) 3.065(3) 125(3)
N1 H4 O5 . 0.912(18) 1.89(2) 2.760(4) 158(3)
N1 H3 O4 . 0.897(18) 1.858(19) 2.752(3) 174(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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 55.9(4) ?
C1 C2 C3 C7 . . . . 65.8(4) ?
C1 C2 C3 C4 . . . . -51.9(4) ?
C1 C2 C3 C8 . . . . -169.2(3) ?
C7 C3 C4 C5 . . . . -69.4(4) ?
C2 C3 C4 C5 . . . . 52.0(4) ?
C8 C3 C4 C5 . . . . 171.4(3) ?
C3 C4 C5 C6 . . . . -54.9(4) ?
C4 C5 C6 C1 . . . . 55.2(5) ?
C2 C1 C6 C5 . . . . -56.5(5) ?
C2 C3 C7 N1 . . . . 53.0(4) ?
C4 C3 C7 N1 . . . . 172.0(3) ?
C8 C3 C7 N1 . . . . -71.5(3) ?
C7 C3 C8 C9 . . . . 80.2(3) ?
C2 C3 C8 C9 . . . . -45.5(4) ?
C4 C3 C8 C9 . . . . -163.7(3) ?
C3 C8 C9 O5 . . . . -61.3(4) ?
C3 C8 C9 O6 . . . . 120.4(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8324812
2 PubChem 139078792
