#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/83/2228308.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_2228308
loop_
_publ_author_name
'Rajeswari, Subadra'
'Venkatesa Prabhu, Ganesan'
'Tamilvendan, Dhanapal'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 Dicyclohexylammonium 3-[(hydroxymethyl)carbamoyl]propanoate
;
_journal_coeditor_code           FJ2363
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3096
_journal_paper_doi               10.1107/S1600536810044958
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H24 N +, C5 H8 N O4 -'
_chemical_formula_moiety         'C12 H24 N +, C5 H8 N O4 -'
_chemical_formula_sum            'C17 H32 N2 O4'
_chemical_formula_weight         328.45
_chemical_name_common
;
Dicyclohexylammonium 4-(hydroxymethylamino)-4-oxobutanoate
;
_chemical_name_systematic
;
Dicyclohexylammonium 3-[(hydroxymethyl)carbamoyl]propanoate
;
_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'
_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                 95.495(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6844(5)
_cell_length_b                   17.7967(12)
_cell_length_c                   18.4264(16)
_cell_measurement_reflns_used    7150
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      1.59
_cell_volume                     1855.5(3)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2009)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS-2'
_diffrn_measurement_method       'φ and ω'
_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  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11855
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         1.59
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULscanABS in PLATON; Spek, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.163
_refine_ls_extinction_coef       0.0046(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.930
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0414
_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)+(0.0463P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                2568
_reflns_number_total             3941
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2363.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2228308
_cod_database_fobs_code          2228308
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
N N1 0.1835(3) 0.16377(7) 0.26459(6) 0.0231(4) Uani . . 1.000
C C1 0.1626(3) 0.15553(8) 0.18284(7) 0.0240(4) Uani . . 1.000
C C2 0.3908(3) 0.17650(9) 0.15118(7) 0.0302(5) Uani . . 1.000
C C3 0.3685(3) 0.16325(9) 0.06882(8) 0.0337(5) Uani . . 1.000
C C4 0.2964(3) 0.08243(9) 0.05011(8) 0.0376(5) Uani . . 1.000
C C5 0.0679(3) 0.06210(9) 0.08250(8) 0.0360(5) Uani . . 1.000
C C6 0.0916(3) 0.07455(8) 0.16494(7) 0.0295(5) Uani . . 1.000
C C7 0.2441(3) 0.24038(8) 0.29523(7) 0.0268(5) Uani . . 1.000
C C8 0.2700(3) 0.23401(9) 0.37808(8) 0.0342(5) Uani . . 1.000
C C9 0.3228(3) 0.31025(10) 0.41315(9) 0.0418(6) Uani . . 1.000
C C10 0.1112(5) 0.37352(10) 0.30517(10) 0.0554(7) Uani . . 1.000
C C11 0.1319(4) 0.36647(10) 0.38784(9) 0.0461(6) Uani . . 1.000
C C12 0.0575(4) 0.29729(9) 0.26847(8) 0.0402(6) Uani . . 1.000
O O1 0.7522(2) 0.63034(6) 0.19198(6) 0.0350(3) Uani . . 1.000
O O2 1.02645(19) 0.55189(6) 0.16058(6) 0.0358(3) Uani . . 1.000
O O3 0.5058(2) 0.35217(7) 0.07565(8) 0.0589(5) Uani . . 1.000
O O4 -0.0493(2) 0.31104(7) 0.07088(6) 0.0382(4) Uani . . 1.000
N N2 0.1841(2) 0.42193(8) 0.08447(7) 0.0317(4) Uani . . 1.000
C C13 0.8158(3) 0.57440(8) 0.15773(7) 0.0256(4) Uani . . 1.000
C C14 0.6297(3) 0.52971(9) 0.11060(8) 0.0292(5) Uani . . 1.000
C C15 0.5506(3) 0.46122(9) 0.15209(8) 0.0334(5) Uani . . 1.000
C C16 0.4109(3) 0.40679(9) 0.10178(8) 0.0324(5) Uani . . 1.000
C C17 0.0415(3) 0.37297(9) 0.03501(8) 0.0341(5) Uani . . 1.000
H H1 0.03410 0.18950 0.16150 0.0290 Uiso calc R 1.000
H H1A 0.290(3) 0.1313(10) 0.2847(8) 0.027(4) Uiso . . 1.000
H H1B 0.038(4) 0.1508(10) 0.2824(10) 0.046(5) Uiso . . 1.000
H H2A 0.52230 0.14590 0.17460 0.0360 Uiso calc R 1.000
H H2B 0.42740 0.23010 0.16150 0.0360 Uiso calc R 1.000
H H3A 0.24910 0.19800 0.04500 0.0400 Uiso calc R 1.000
H H3B 0.52180 0.17420 0.04970 0.0400 Uiso calc R 1.000
H H4A 0.27430 0.07640 -0.00350 0.0450 Uiso calc R 1.000
H H4B 0.42380 0.04790 0.06940 0.0450 Uiso calc R 1.000
H H5A 0.02890 0.00880 0.07180 0.0430 Uiso calc R 1.000
H H5B -0.06280 0.09340 0.05960 0.0430 Uiso calc R 1.000
H H6A -0.06090 0.06330 0.18450 0.0350 Uiso calc R 1.000
H H6B 0.21240 0.04000 0.18840 0.0350 Uiso calc R 1.000
H H7 0.39910 0.25640 0.27880 0.0320 Uiso calc R 1.000
H H8A 0.12210 0.21370 0.39470 0.0410 Uiso calc R 1.000
H H8B 0.39970 0.19870 0.39350 0.0410 Uiso calc R 1.000
H H9A 0.33190 0.30530 0.46690 0.0500 Uiso calc R 1.000
H H9B 0.47760 0.32860 0.40000 0.0500 Uiso calc R 1.000
H H10A 0.26100 0.39360 0.28970 0.0670 Uiso calc R 1.000
H H10B -0.01650 0.40940 0.28940 0.0670 Uiso calc R 1.000
H H11A 0.17100 0.41610 0.41020 0.0550 Uiso calc R 1.000
H H11B -0.02120 0.34990 0.40380 0.0550 Uiso calc R 1.000
H H12A -0.09990 0.27950 0.27980 0.0480 Uiso calc R 1.000
H H12B 0.05430 0.30280 0.21490 0.0480 Uiso calc R 1.000
H H2N 0.124(3) 0.4572(10) 0.1056(9) 0.034(5) Uiso . . 1.000
H H4O -0.195(4) 0.3219(13) 0.0796(11) 0.068(7) Uiso . . 1.000
H H14A 0.69610 0.51300 0.06550 0.0350 Uiso calc R 1.000
H H14B 0.49160 0.56220 0.09640 0.0350 Uiso calc R 1.000
H H15A 0.69130 0.43540 0.17620 0.0400 Uiso calc R 1.000
H H15B 0.45190 0.47800 0.19050 0.0400 Uiso calc R 1.000
H H17A -0.09140 0.40220 0.01050 0.0410 Uiso calc R 1.000
H H17B 0.13900 0.35450 -0.00300 0.0410 Uiso calc R 1.000
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'
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
C17 O4 H4O . . . 107.9(15) no
C1 N1 C7 . . . 117.20(11) no
C7 N1 H1A . . . 108.0(11) no
C1 N1 H1A . . . 109.8(10) no
C1 N1 H1B . . . 109.6(11) no
C7 N1 H1B . . . 105.5(11) no
H1A N1 H1B . . . 106.2(16) no
C16 N2 C17 . . . 120.06(14) no
C16 N2 H2N . . . 118.4(12) no
C17 N2 H2N . . . 121.3(12) no
N1 C1 C2 . . . 111.81(13) no
C2 C1 C6 . . . 111.55(13) no
N1 C1 C6 . . . 107.59(11) no
C1 C2 C3 . . . 110.53(13) no
C2 C3 C4 . . . 111.38(13) no
C3 C4 C5 . . . 110.84(13) no
C4 C5 C6 . . . 110.95(13) no
C1 C6 C5 . . . 110.40(12) no
N1 C7 C8 . . . 107.79(11) no
N1 C7 C12 . . . 110.86(13) no
C8 C7 C12 . . . 111.92(13) no
C7 C8 C9 . . . 110.83(13) no
C8 C9 C11 . . . 110.60(14) no
C11 C10 C12 . . . 111.20(14) no
C9 C11 C10 . . . 110.29(16) no
C7 C12 C10 . . . 110.15(16) no
N1 C1 H1 . . . 109.00 no
C6 C1 H1 . . . 109.00 no
C2 C1 H1 . . . 109.00 no
C3 C2 H2B . . . 110.00 no
C3 C2 H2A . . . 110.00 no
H2A C2 H2B . . . 108.00 no
C1 C2 H2B . . . 110.00 no
C1 C2 H2A . . . 110.00 no
C2 C3 H3B . . . 109.00 no
H3A C3 H3B . . . 108.00 no
C4 C3 H3B . . . 109.00 no
C2 C3 H3A . . . 109.00 no
C4 C3 H3A . . . 109.00 no
C5 C4 H4B . . . 109.00 no
H4A C4 H4B . . . 108.00 no
C5 C4 H4A . . . 109.00 no
C3 C4 H4A . . . 109.00 no
C3 C4 H4B . . . 109.00 no
C4 C5 H5B . . . 109.00 no
H5A C5 H5B . . . 108.00 no
C4 C5 H5A . . . 109.00 no
C6 C5 H5B . . . 109.00 no
C6 C5 H5A . . . 109.00 no
C1 C6 H6B . . . 110.00 no
H6A C6 H6B . . . 108.00 no
C5 C6 H6B . . . 110.00 no
C1 C6 H6A . . . 110.00 no
C5 C6 H6A . . . 110.00 no
N1 C7 H7 . . . 109.00 no
C8 C7 H7 . . . 109.00 no
C12 C7 H7 . . . 109.00 no
C7 C8 H8B . . . 109.00 no
C9 C8 H8A . . . 109.00 no
C7 C8 H8A . . . 109.00 no
C9 C8 H8B . . . 109.00 no
H8A C8 H8B . . . 108.00 no
C11 C9 H9B . . . 109.00 no
H9A C9 H9B . . . 108.00 no
C8 C9 H9A . . . 110.00 no
C8 C9 H9B . . . 110.00 no
C11 C9 H9A . . . 109.00 no
C11 C10 H10B . . . 109.00 no
C12 C10 H10A . . . 109.00 no
C12 C10 H10B . . . 109.00 no
C11 C10 H10A . . . 109.00 no
H10A C10 H10B . . . 108.00 no
C9 C11 H11B . . . 110.00 no
H11A C11 H11B . . . 108.00 no
C10 C11 H11A . . . 110.00 no
C9 C11 H11A . . . 110.00 no
C10 C11 H11B . . . 110.00 no
C10 C12 H12B . . . 110.00 no
H12A C12 H12B . . . 108.00 no
C7 C12 H12B . . . 110.00 no
C10 C12 H12A . . . 110.00 no
C7 C12 H12A . . . 110.00 no
O1 C13 O2 . . . 123.51(14) no
O1 C13 C14 . . . 118.94(15) no
O2 C13 C14 . . . 117.55(13) no
C13 C14 C15 . . . 110.60(12) no
C14 C15 C16 . . . 111.49(12) no
O3 C16 N2 . . . 121.23(15) no
O3 C16 C15 . . . 121.41(15) no
N2 C16 C15 . . . 117.30(14) no
O4 C17 N2 . . . 112.52(12) no
C13 C14 H14A . . . 110.00 no
C13 C14 H14B . . . 110.00 no
C15 C14 H14A . . . 110.00 no
C15 C14 H14B . . . 110.00 no
H14A C14 H14B . . . 108.00 no
C14 C15 H15A . . . 109.00 no
C14 C15 H15B . . . 109.00 no
C16 C15 H15A . . . 109.00 no
C16 C15 H15B . . . 109.00 no
H15A C15 H15B . . . 108.00 no
O4 C17 H17A . . . 109.00 no
O4 C17 H17B . . . 109.00 no
N2 C17 H17A . . . 109.00 no
N2 C17 H17B . . . 109.00 no
H17A C17 H17B . . . 108.00 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
O1 C13 . . 1.2505(18) no
O2 C13 . . 1.259(2) no
O3 C16 . . 1.232(2) no
O4 C17 . . 1.408(2) no
O4 H4O . . 0.88(2) no
N1 C1 . . 1.5068(17) no
N1 C7 . . 1.5030(19) no
N1 H1A . . 0.892(17) no
N1 H1B . . 0.95(2) no
N2 C16 . . 1.326(2) no
N2 C17 . . 1.451(2) no
N2 H2N . . 0.829(17) no
C1 C6 . . 1.524(2) no
C1 C2 . . 1.519(2) no
C2 C3 . . 1.529(2) no
C3 C4 . . 1.526(2) no
C4 C5 . . 1.524(2) no
C5 C6 . . 1.528(2) no
C7 C12 . . 1.515(2) no
C7 C8 . . 1.524(2) no
C8 C9 . . 1.520(2) no
C9 C11 . . 1.516(3) no
C10 C12 . . 1.533(2) no
C10 C11 . . 1.522(2) no
C1 H1 . . 1.0000 no
C2 H2A . . 0.9900 no
C2 H2B . . 0.9900 no
C3 H3B . . 0.9900 no
C3 H3A . . 0.9900 no
C4 H4B . . 0.9900 no
C4 H4A . . 0.9900 no
C5 H5A . . 0.9900 no
C5 H5B . . 0.9900 no
C6 H6B . . 0.9900 no
C6 H6A . . 0.9900 no
C7 H7 . . 1.0000 no
C8 H8B . . 0.9900 no
C8 H8A . . 0.9900 no
C9 H9B . . 0.9900 no
C9 H9A . . 0.9900 no
C10 H10B . . 0.9900 no
C10 H10A . . 0.9900 no
C11 H11B . . 0.9900 no
C11 H11A . . 0.9900 no
C12 H12B . . 0.9900 no
C12 H12A . . 0.9900 no
C13 C14 . . 1.526(2) no
C14 C15 . . 1.529(2) no
C15 C16 . . 1.512(2) no
C14 H14A . . 0.9900 no
C14 H14B . . 0.9900 no
C15 H15A . . 0.9900 no
C15 H15B . . 0.9900 no
C17 H17A . . 0.9900 no
C17 H17B . . 0.9900 no
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 2_645 0.892(17) 2.597(17) 3.285(2) 134.7(14) yes
N1 H1A O2 2_645 0.892(17) 1.975(17) 2.8546(18) 168.7(15) yes
N1 H1B O1 2_545 0.95(2) 1.80(2) 2.740(2) 174.3(17) yes
N2 H2N O2 1_455 0.829(17) 2.069(17) 2.8914(18) 171.1(16) yes
O4 H4O O3 1_455 0.88(2) 1.78(2) 2.6423(16) 166.4(19) yes
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
C7 N1 C1 C2 . . . . 59.28(18) no
C7 N1 C1 C6 . . . . -177.90(14) no
C1 N1 C7 C8 . . . . -176.66(14) no
C1 N1 C7 C12 . . . . 60.53(19) no
C16 N2 C17 O4 . . . . 84.82(17) no
C17 N2 C16 O3 . . . . 1.2(2) no
C17 N2 C16 C15 . . . . 178.48(13) no
N1 C1 C2 C3 . . . . 176.74(12) no
C2 C1 C6 C5 . . . . -56.83(17) no
C6 C1 C2 C3 . . . . 56.21(16) no
N1 C1 C6 C5 . . . . -179.81(14) no
C1 C2 C3 C4 . . . . -55.54(17) no
C2 C3 C4 C5 . . . . 55.81(17) no
C3 C4 C5 C6 . . . . -56.27(17) no
C4 C5 C6 C1 . . . . 56.57(17) no
N1 C7 C8 C9 . . . . -177.94(14) no
C8 C7 C12 C10 . . . . 54.9(2) no
C12 C7 C8 C9 . . . . -55.78(19) no
N1 C7 C12 C10 . . . . 175.30(14) no
C7 C8 C9 C11 . . . . 56.73(18) no
C8 C9 C11 C10 . . . . -57.9(2) no
C12 C10 C11 C9 . . . . 57.7(3) no
C11 C10 C12 C7 . . . . -55.9(2) no
O1 C13 C14 C15 . . . . -96.94(16) no
O2 C13 C14 C15 . . . . 82.16(17) no
C13 C14 C15 C16 . . . . -166.86(13) no
C14 C15 C16 O3 . . . . 95.92(18) no
C14 C15 C16 N2 . . . . -81.33(18) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656347
