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###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'SHELXL97'
_journal_date_recd_electronic     2004-07-26
_journal_date_accepted     2004-08-25
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2004
_journal_volume     60
_journal_issue     10
_journal_page_first     o759
_journal_page_last     o761
_journal_paper_category     FO
_publ_contact_author_name     'Dr Asiloé J. Mora'
_publ_contact_author_address
;
     Laboratorio de Cristalografía
     Facultad de Ciencias
     Departamento de Química
     Universidad de Los Andes
     Mérida 5101
     Venezuela
;
_publ_contact_author_email     asiloe@ula.ve
_publ_contact_author_fax     '58 74 401286'
_publ_contact_author_phone     '58 74 401372'
_publ_section_title
;
Hydrogen-bonding patterns in cis-4-ammoniocyclohexanecarboxylate
hemihydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Edward E. Ávila'
;    Laboratorio de Cristalografía
     Facultad de Ciencias
     Departamento de Química
     Universidad de Los Andes
     Mérida 5101
     Venezuela
;
    'Asiloé J. Mora*'
;    Laboratorio de Cristalografía
     Facultad de Ciencias
     Departamento de Química
     Universidad de Los Andes
     Mérida 5101
     Venezuela
;
    'Gerzon E. Delgado'
;    Laboratorio de Cristalografía
     Facultad de Ciencias
     Departamento de Química
     Universidad de Los Andes
     Mérida 5101
     Venezuela
;
    'Belkis M. Ramírez'
;    Laboratorio de Cristalografía
     Facultad de Ciencias
     Departamento de Química
     Universidad de Los Andes
     Mérida 5101
     Venezuela
;
    'Alí Bahsas'
;    Laboratorio de Resonancia Magnética Nuclear
     Facultad de Ciencias
     Departamento de Química
     Universidad de Los Andes
     Mérida 5101
     Venezuela
;
    'Sonia Koteich'
;    Laboratorio de Resonancia Magnética Nuclear
     Facultad de Ciencias
     Departamento de Química
     Universidad de Los Andes
     Mérida 5101
     Venezuela
;
data_I
_chemical_name_systematic
;
cis-4-ammoniocyclohexanecarboxylate hemihydrate
;
_chemical_name_common     'cis-4-aminocyclohexane carboxylic acid hemihydrate'
_chemical_formula_moiety     'C7 H13 N O2, 0.5H2 O'
_chemical_formula_sum     'C7  H14 N  O2.5'
_chemical_formula_iupac     'C7 H13 N O2, 0.5H2 O'
_chemical_formula_weight     152.19
_chemical_melting_point     543.7(2)
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     19.871(4)
_cell_length_b     6.1614(11)
_cell_length_c     13.475(2)
_cell_angle_alpha     90.00
_cell_angle_beta     104.452(3)
_cell_angle_gamma     90.00
_cell_volume     1597.6(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3462
_cell_measurement_theta_min     2.12
_cell_measurement_theta_max     28.29
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.265
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.8900
_exptl_absorpt_correction_T_max     0.9800
_exptl_special_details
;
?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7982
_diffrn_reflns_av_R_equivalents     0.0595
_diffrn_reflns_av_sigmaI/netI     0.0591
_diffrn_reflns_theta_min     2.12
_diffrn_reflns_theta_max     28.29
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.950
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -26
_diffrn_reflns_limit_h_max     26
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1880
_reflns_number_gt     1100
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1028
_refine_ls_R_factor_gt     0.0473
_refine_ls_wR_factor_gt     0.0928
_refine_ls_wR_factor_ref     0.1024
_refine_ls_goodness_of_fit_ref     0.974
_refine_ls_restrained_S_all     0.974
_refine_ls_number_reflns     1880
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                  'calc w=1/[σ²(Fo²)+(0.0496)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.187
_refine_diff_density_min     -0.176
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    '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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'DIAMOND (Branderburg, 1998)'
_computing_publication_material
;
SHELXL97 and PLATON (Spek, 1990)
;
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    O1 0.19125(6) 0.1498(2) 0.82728(9) 0.0444(4) Uani d . 1 . . O
    O2 0.12833(7) 0.4494(2) 0.80900(10) 0.0535(4) Uani d . 1 . . O
    N1 0.18569(8) 0.2275(3) 1.21393(11) 0.0341(4) Uani d . 1 . . N
    H1N 0.1893(9) 0.114(3) 1.2563(14) 0.046(5) Uiso d . 1 . . H
    H2N 0.2277(11) 0.258(3) 1.2017(15) 0.056(6) Uiso d . 1 . . H
    H3N 0.1689(9) 0.346(3) 1.2427(15) 0.057(6) Uiso d . 1 . . H
    C1 0.13990(8) 0.2585(3) 0.83866(12) 0.0318(4) Uani d . 1 . . C
    C2 0.08859(8) 0.1499(3) 0.89015(13) 0.0347(4) Uani d . 1 . . C
    H2 0.0506 0.1009 0.8364 0.042 Uiso calc R 1 . . H
    C3 0.05855(9) 0.3107(3) 0.95420(14) 0.0444(5) Uani d . 1 . . C
    H3A 0.0439 0.4382 0.9150 0.053 Uiso calc R 1 . . H
    H3B 0.0189 0.2480 0.9706 0.053 Uiso calc R 1 . . H
    C4 0.11137(9) 0.3711(3) 1.05225(13) 0.0393(5) Uani d . 1 . . C
    H4A 0.1515 0.4422 1.0357 0.047 Uiso calc R 1 . . H
    H4B 0.0905 0.4737 1.0918 0.047 Uiso calc R 1 . . H
    C5 0.13517(9) 0.1698(3) 1.11559(12) 0.0328(4) Uani d . 1 . . C
    H5 0.0952 0.1033 1.1313 0.039 Uiso calc R 1 . . H
    C6 0.16715(9) 0.0077(3) 1.05560(13) 0.0365(4) Uani d . 1 . . C
    H6A 0.2092 0.0691 1.0426 0.044 Uiso calc R 1 . . H
    H6B 0.1799 -0.1232 1.0961 0.044 Uiso calc R 1 . . H
    C7 0.11691(9) -0.0496(3) 0.95459(13) 0.0400(5) Uani d . 1 . . C
    H7A 0.0784 -0.1307 0.9681 0.048 Uiso calc R 1 . . H
    H7B 0.1403 -0.1423 0.9158 0.048 Uiso calc R 1 . . H
    O1W 0.5000 0.2077(4) 0.7500 0.0651(6) Uani d S 1 . . O
    H1W 0.5343(12) 0.117(4) 0.768(2) 0.090(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
    O1 0.0404(7) 0.0414(7) 0.0590(8) -0.0057(6) 0.0267(6) -0.0124(6)
    O2 0.0597(8) 0.0443(8) 0.0650(9) 0.0026(6) 0.0317(7) 0.0197(7)
    N1 0.0390(9) 0.0319(9) 0.0353(8) 0.0002(7) 0.0167(7) 0.0010(7)
    C1 0.0362(9) 0.0333(9) 0.0275(8) -0.0068(8) 0.0107(7) -0.0045(7)
    C2 0.0304(8) 0.0400(10) 0.0338(9) -0.0089(8) 0.0083(7) 0.0015(8)
    C3 0.0361(9) 0.0586(12) 0.0436(11) 0.0108(9) 0.0195(8) 0.0137(9)
    C4 0.0483(11) 0.0358(10) 0.0395(10) 0.0128(8) 0.0219(9) 0.0031(8)
    C5 0.0334(9) 0.0337(9) 0.0350(9) -0.0017(8) 0.0153(7) 0.0019(7)
    C6 0.0478(10) 0.0252(9) 0.0379(10) 0.0043(7) 0.0130(8) 0.0015(7)
    C7 0.0495(10) 0.0342(10) 0.0402(10) -0.0121(8) 0.0184(9) -0.0012(8)
    O1W 0.0641(14) 0.0496(13) 0.0725(16) 0.000 0.0002(12) 0.000
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 . 1.261(2) yes
    C1 O2 . 1.245(2) yes
    C5 N1 . 1.492(2) yes
    N1 H1N . 0.89(2) ?
    N1 H2N . 0.91(2) ?
    N1 H3N . 0.93(2) ?
    C1 C2 . 1.524(2) yes
    C2 C7 . 1.529(2) yes
    C2 C3 . 1.530(2) yes
    C2 H2 . 0.9559 ?
    C3 C4 . 1.515(3) yes
    C3 H3A . 0.9509 ?
    C3 H3B . 0.9509 ?
    C4 C5 . 1.513(2) yes
    C4 H4A . 0.9833 ?
    C4 H4B . 0.9833 ?
    C5 C6 . 1.520(2) yes
    C5 H5 . 0.9625 ?
    C6 C7 . 1.515(2) yes
    C6 H6A . 0.9712 ?
    C6 H6B . 0.9712 ?
    C7 H7A . 0.9681 ?
    C7 H7B . 0.9681 ?
    O1W H1W . 0.87(2) ?
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
    C5 N1 H1N . . 108.1(11) ?
    C5 N1 H2N . . 109.4(12) ?
    H1N N1 H2N . . 110.3(16) ?
    C5 N1 H3N . . 109.1(11) ?
    H1N N1 H3N . . 109.2(17) ?
    H2N N1 H3N . . 110.8(16) ?
    O2 C1 O1 . . 123.6(2) yes
    O2 C1 C2 . . 118.0(2) yes
    O1 C1 C2 . . 118.4(2) yes
    C1 C2 C7 . . 114.70(10)
                          ?
    C1 C2 C3 . . 111.90(10)
                          ?
    C7 C2 C3 . . 109.90(10)
                          ?
    C1 C2 H2 . . 106.6 ?
    C7 C2 H2 . . 106.6 ?
    C3 C2 H2 . . 106.6 ?
    C4 C3 C2 . . 111.60(10)
                          ?
    C4 C3 H3A . . 109.3 ?
    C2 C3 H3A . . 109.3 ?
    C4 C3 H3B . . 109.3 ?
    C2 C3 H3B . . 109.3 ?
    H3A C3 H3B . . 108.0 ?
    C5 C4 C3 . . 109.98(15) ?
    C5 C4 H4A . . 109.7 ?
    C3 C4 H4A . . 109.7 ?
    C5 C4 H4B . . 109.7 ?
    C3 C4 H4B . . 109.7 ?
    H4A C4 H4B . . 108.2 ?
    N1 C5 C4 . . 110.60(10)
                          yes
    N1 C5 C6 . . 110.50(10)
                          yes
    C4 C5 C6 . . 110.60(10)
                          ?
    N1 C5 H5 . . 108.3 ?
    C4 C5 H5 . . 108.3 ?
    C6 C5 H5 . . 108.3 ?
    C7 C6 C5 . . 111.20(15) ?
    C7 C6 H6A . . 109.4 ?
    C5 C6 H6A . . 109.4 ?
    C7 C6 H6B . . 109.4 ?
    C5 C6 H6B . . 109.4 ?
    H6A C6 H6B . . 108.0 ?
    C6 C7 C2 . . 112.92(14) ?
    C6 C7 H7A . . 109.0 ?
    C2 C7 H7A . . 109.0 ?
    C6 C7 H7B . . 109.0 ?
    C2 C7 H7B . . 109.0 ?
    H7A C7 H7B . . 107.8 ?
    H1W O1W H1W . 2_656 100(2) ?
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
    N1 H2N O1 7_557 0.91(2) 1.84(2) 2.745(2) 174(2)
    O1W H1W O2 3_545 0.87(2) 2.09(2) 2.942(2) 169(2)
    N1 H3N O2 6_566 0.93(2) 1.84(2) 2.763(2) 171(2)
    N1 H1N O1 6_556 0.89(2) 1.88(2) 2.769(2) 171(2)
