##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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     SHELXL-97
_journal_date_recd_electronic     2004-03-09
_journal_date_accepted     2004-04-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      5
_journal_page_first     o857
_journal_page_last     o859
_journal_paper_category     EO
_publ_contact_author_name     'Professor Gautam R. Desiraju'
_publ_contact_author_address
; School of Chemistry
University of Hyderabad
Hyderabad 500 046,
India
;
_publ_contact_author_email     desiraju@uohyd.ernet.in
_publ_contact_author_fax     '91 40 3010567'
_publ_contact_author_phone     '91 40 23010500 extn. 4828'
_publ_section_title
;
A 1:1 molecular complex of 4-aminocyclohexanol and
(4-hydroxycyclohexyl)carbamic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Archan Dey'
;
School of Chemistry
University of Hyderabad
Hyderabad 500 046
India
;
    'Gautam R. Desiraju'
;
School of Chemistry
University of Hyderabad
Hyderabad 500 046
India
;
    'Raju Mondal'
;
Department of Chemistry
University of Durham
Durham DH1 3LE
England
;
    'Judith A. K.Howard'
;
Department of Chemistry
University of Durham
Durham DH1 3LE
England
;
data_I
_chemical_name_systematic
;
4-ammoniocyclohexanol--(4-hydroxycyclohexyl)carbamate (1/1)
;
_chemical_name_common
                   '4-Aminoclyhexanol, (4-hydroxyclyhexyl)-carbamic acid (1:1) '
_chemical_formula_moiety     'C7 H12 N O3, C6 H14 N1 O1'
_chemical_formula_sum     'C13 H26 N2 O4'
_chemical_formula_iupac     'C6 H14 N1 O1 1+, C7 H12 N O3 1-'
_chemical_formula_weight     274.36
_chemical_melting_point     377
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     6.3452(2)
_cell_length_b     18.6256(6)
_cell_length_c     12.1664(4)
_cell_angle_alpha     90.00
_cell_angle_beta     92.284(2)
_cell_angle_gamma     90.00
_cell_volume     1436.72(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4934
_cell_measurement_theta_min     2.755
_cell_measurement_theta_max     27.469
_cell_measurement_temperature     120(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.268
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.093
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.927248
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(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     'SMART 6k CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8
_diffrn_reflns_number     19783
_diffrn_reflns_av_R_equivalents     0.0381
_diffrn_reflns_av_sigmaI/netI     0.0265
_diffrn_reflns_theta_min     2.00
_diffrn_reflns_theta_max     27.51
_diffrn_reflns_theta_full     27.51
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -24
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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     3308
_reflns_number_gt     2537
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0544
_refine_ls_R_factor_gt     0.0372
_refine_ls_wR_factor_gt     0.0918
_refine_ls_wR_factor_ref     0.1021
_refine_ls_goodness_of_fit_ref     1.014
_refine_ls_restrained_S_all     1.014
_refine_ls_number_reflns     3308
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0538P)²+0.3252P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.274
_refine_diff_density_min     -0.183
_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'
    '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'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2001)'
_computing_publication_material     'SHELXTL'
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
    O3 -0.46270(13) 0.63687(5) 0.01886(7) 0.0216(2) Uani d . 1 . . O
    O2 -0.15113(14) 0.58448(5) 0.05544(7) 0.0223(2) Uani d . 1 . . O
    O1 0.35337(16) 0.73442(5) 0.48724(8) 0.0300(2) Uani d . 1 . . O
    N1' 0.74068(18) 0.46768(6) 0.91750(8) 0.0182(2) Uani d . 1 . . N
    O1' 0.56745(17) 0.60426(6) 0.50683(8) 0.0303(2) Uani d . 1 . . O
    N1 -0.21577(18) 0.69590(6) 0.12248(9) 0.0227(2) Uani d . 1 . . N
    C7 -0.27812(19) 0.63633(6) 0.06402(9) 0.0172(2) Uani d . 1 . . C
    C1 -0.0410(2) 0.69605(7) 0.20400(10) 0.0197(3) Uani d . 1 . . C
    C1' 0.68231(19) 0.48446(7) 0.79946(10) 0.0182(3) Uani d . 1 . . C
    C4 0.1752(2) 0.74117(7) 0.41197(10) 0.0220(3) Uani d . 1 . . C
    C5 0.2403(2) 0.76883(8) 0.30124(11) 0.0290(3) Uani d . 1 . . C
    C5' 0.4282(2) 0.54960(7) 0.67150(10) 0.0217(3) Uani d . 1 . . C
    C4' 0.6106(2) 0.58854(7) 0.61997(10) 0.0229(3) Uani d . 1 . . C
    C6' 0.4831(2) 0.52980(7) 0.79140(10) 0.0206(3) Uani d . 1 . . C
    C3' 0.8078(2) 0.54205(8) 0.62791(12) 0.0291(3) Uani d . 1 . . C
    C6 0.0536(3) 0.77048(8) 0.21763(12) 0.0298(3) Uani d . 1 . . C
    C2' 0.8658(2) 0.52213(8) 0.74691(12) 0.0266(3) Uani d . 1 . . C
    C3 0.0736(3) 0.66789(8) 0.39996(12) 0.0321(3) Uani d . 1 . . C
    C2 -0.1096(2) 0.66843(9) 0.31494(12) 0.0310(3) Uani d . 1 . . C
    H1A 0.066(2) 0.6656(8) 0.1757(12) 0.020(3) Uiso d . 1 . . H
    H1B 0.658(2) 0.4379(7) 0.7637(11) 0.015(3) Uiso d . 1 . . H
    H2D 0.893(2) 0.5668(9) 0.7913(13) 0.028(4) Uiso d . 1 . . H
    H6D 0.506(2) 0.5722(8) 0.8348(12) 0.021(4) Uiso d . 1 . . H
    H4' 0.636(2) 0.6353(8) 0.6590(12) 0.021(4) Uiso d . 1 . . H
    H5D 0.400(2) 0.5061(8) 0.6273(12) 0.020(4) Uiso d . 1 . . H
    H4 0.073(3) 0.7753(9) 0.4436(13) 0.030(4) Uiso d . 1 . . H
    H3D 0.925(3) 0.5664(9) 0.5937(14) 0.033(4) Uiso d . 1 . . H
    H5C 0.307(3) 0.5814(9) 0.6675(13) 0.030(4) Uiso d . 1 . . H
    H115 -0.315(3) 0.7273(10) 0.1311(14) 0.038(5) Uiso d . 1 . . H
    H114 0.870(3) 0.4447(9) 0.9227(13) 0.031(4) Uiso d . 1 . . H
    H2A -0.221(3) 0.7018(11) 0.3403(15) 0.047(5) Uiso d . 1 . . H
    H112 0.641(3) 0.4352(9) 0.9465(14) 0.038(5) Uiso d . 1 . . H
    H111 0.756(2) 0.5090(9) 0.9608(13) 0.027(4) Uiso d . 1 . . H
    H6C 0.370(2) 0.5034(8) 0.8226(12) 0.021(4) Uiso d . 1 . . H
    H5A 0.352(3) 0.7351(10) 0.2737(15) 0.042(5) Uiso d . 1 . . H
    H1' 0.498(3) 0.6467(10) 0.5041(15) 0.042(5) Uiso d . 1 . . H
    H3C 0.776(3) 0.4966(11) 0.5837(15) 0.045(5) Uiso d . 1 . . H
    H2C 0.988(3) 0.4894(9) 0.7499(13) 0.036(4) Uiso d . 1 . . H
    H3A 0.188(3) 0.6337(10) 0.3776(14) 0.042(5) Uiso d . 1 . . H
    H6B -0.058(3) 0.8024(10) 0.2441(14) 0.035(4) Uiso d . 1 . . H
    H2B -0.171(3) 0.6200(10) 0.3086(14) 0.039(5) Uiso d . 1 . . H
    H6A 0.095(3) 0.7889(10) 0.1460(16) 0.047(5) Uiso d . 1 . . H
    H3B 0.026(3) 0.6536(11) 0.4732(17) 0.053(5) Uiso d . 1 . . H
    H1 0.419(3) 0.7770(11) 0.4939(16) 0.049(5) Uiso d . 1 . . H
    H5B 0.305(3) 0.8174(10) 0.3088(14) 0.042(5) Uiso d . 1 . . H
_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
    O3 C7 . 1.2737(14) ?
    O2 C7 . 1.2647(15) ?
    O1 C4 . 1.4316(15) ?
    O1 H1 . 0.90(2) ?
    N1' C1' . 1.5016(15) ?
    N1' H114 . 0.924(18) ?
    N1' H112 . 0.953(18) ?
    N1' H111 . 0.937(17) ?
    O1' C4' . 1.4231(15) ?
    O1' H1' . 0.905(19) ?
    N1 C7 . 1.3679(15) ?
    N1 C1 . 1.4578(15) ?
    N1 H115 . 0.869(19) ?
    C1 C6 . 1.5170(18) ?
    C1 C2 . 1.5240(19) ?
    C1 H1A . 0.958(15) ?
    C1' C6' . 1.5198(17) ?
    C1' C2' . 1.5216(18) ?
    C1' H1B . 0.979(14) ?
    C4 C3 . 1.5141(18) ?
    C4 C5 . 1.5151(19) ?
    C4 H4 . 0.996(16) ?
    C5 C6 . 1.5310(19) ?
    C5 H5A . 1.016(19) ?
    C5 H5B . 0.996(19) ?
    C5' C4' . 1.5224(19) ?
    C5' C6' . 1.5314(17) ?
    C5' H5D . 0.984(15) ?
    C5' H5C . 0.971(17) ?
    C4' C3' . 1.5215(19) ?
    C4' H4' . 1.002(15) ?
    C6' H6D . 0.959(15) ?
    C6' H6C . 0.961(16) ?
    C3' C2' . 1.5253(19) ?
    C3' H3D . 0.980(18) ?
    C3' H3C . 1.019(19) ?
    C6 H6B . 0.990(18) ?
    C6 H6A . 0.982(19) ?
    C2' H2D . 1.003(16) ?
    C2' H2C . 0.984(18) ?
    C3 C2 . 1.5249(19) ?
    C3 H3A . 1.011(19) ?
    C3 H3B . 0.99(2) ?
    C2 H2A . 1.00(2) ?
    C2 H2B . 0.983(18) ?
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
    C4 O1 H1 . . 109.3(12) ?
    C1' N1' H114 . . 110.2(10) ?
    C1' N1' H112 . . 110.1(10) ?
    H114 N1' H112 . . 106.3(14) ?
    C1' N1' H111 . . 112.6(9) ?
    H114 N1' H111 . . 105.6(14) ?
    H112 N1' H111 . . 111.7(14) ?
    C4' O1' H1' . . 106.9(12) ?
    C7 N1 C1 . . 123.48(11) ?
    C7 N1 H115 . . 114.4(12) ?
    C1 N1 H115 . . 116.9(12) ?
    O2 C7 O3 . . 123.25(11) ?
    O2 C7 N1 . . 119.36(11) ?
    O3 C7 N1 . . 117.38(11) ?
    N1 C1 C6 . . 111.28(10) ?
    N1 C1 C2 . . 111.45(11) ?
    C6 C1 C2 . . 109.71(11) ?
    N1 C1 H1A . . 106.5(8) ?
    C6 C1 H1A . . 107.3(9) ?
    C2 C1 H1A . . 110.5(9) ?
    N1' C1' C6' . . 110.50(10) ?
    N1' C1' C2' . . 109.52(10) ?
    C6' C1' C2' . . 111.39(10) ?
    N1' C1' H1B . . 105.6(8) ?
    C6' C1' H1B . . 110.2(8) ?
    C2' C1' H1B . . 109.4(8) ?
    O1 C4 C3 . . 107.75(10) ?
    O1 C4 C5 . . 111.25(11) ?
    C3 C4 C5 . . 110.54(11) ?
    O1 C4 H4 . . 108.5(9) ?
    C3 C4 H4 . . 109.3(9) ?
    C5 C4 H4 . . 109.4(9) ?
    C4 C5 C6 . . 111.49(12) ?
    C4 C5 H5A . . 107.6(10) ?
    C6 C5 H5A . . 109.1(10) ?
    C4 C5 H5B . . 110.7(10) ?
    C6 C5 H5B . . 110.5(10) ?
    H5A C5 H5B . . 107.4(14) ?
    C4' C5' C6' . . 111.03(10) ?
    C4' C5' H5D . . 107.0(8) ?
    C6' C5' H5D . . 110.6(8) ?
    C4' C5' H5C . . 107.6(9) ?
    C6' C5' H5C . . 110.2(9) ?
    H5D C5' H5C . . 110.4(13) ?
    O1' C4' C3' . . 107.74(11) ?
    O1' C4' C5' . . 112.09(11) ?
    C3' C4' C5' . . 109.85(11) ?
    O1' C4' H4' . . 107.5(8) ?
    C3' C4' H4' . . 110.5(8) ?
    C5' C4' H4' . . 109.1(8) ?
    C1' C6' C5' . . 110.64(10) ?
    C1' C6' H6D . . 108.3(9) ?
    C5' C6' H6D . . 110.5(9) ?
    C1' C6' H6C . . 108.8(9) ?
    C5' C6' H6C . . 110.8(9) ?
    H6D C6' H6C . . 107.7(12) ?
    C4' C3' C2' . . 111.42(12) ?
    C4' C3' H3D . . 110.3(10) ?
    C2' C3' H3D . . 110.9(10) ?
    C4' C3' H3C . . 107.1(11) ?
    C2' C3' H3C . . 109.5(10) ?
    H3D C3' H3C . . 107.4(14) ?
    C1 C6 C5 . . 110.28(11) ?
    C1 C6 H6B . . 107.4(10) ?
    C5 C6 H6B . . 110.0(10) ?
    C1 C6 H6A . . 110.0(11) ?
    C5 C6 H6A . . 111.6(11) ?
    H6B C6 H6A . . 107.4(15) ?
    C1' C2' C3' . . 110.58(11) ?
    C1' C2' H2D . . 106.0(9) ?
    C3' C2' H2D . . 109.9(9) ?
    C1' C2' H2C . . 108.2(10) ?
    C3' C2' H2C . . 110.2(10) ?
    H2D C2' H2C . . 111.9(13) ?
    C4 C3 C2 . . 111.69(12) ?
    C4 C3 H3A . . 106.7(10) ?
    C2 C3 H3A . . 111.0(10) ?
    C4 C3 H3B . . 107.4(12) ?
    C2 C3 H3B . . 111.2(12) ?
    H3A C3 H3B . . 108.7(15) ?
    C1 C2 C3 . . 111.49(12) ?
    C1 C2 H2A . . 107.1(11) ?
    C3 C2 H2A . . 109.0(11) ?
    C1 C2 H2B . . 111.4(10) ?
    C3 C2 H2B . . 109.5(10) ?
    H2A C2 H2B . . 108.2(15) ?
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
    O1' H1' O1 . 0.90(2) 1.88(2) 2.784(2) 176.0(10)
    O1 H1 O3 4_676 0.90(2) 1.79(2) 2.6870(10)
                                            175(2)
    N1' H111 O2 1_656 0.94(2) 1.90(2) 2.8160(10)
                                               167.0(10)
    N1' H112 O3 3_566 0.95(2) 1.82(2) 2.75900(10)
                                                170.0(10)
    N1' H114 O2 3_666 0.92(2) 1.87(2) 2.78700(10)
                                                169.0(10)
    C6' H6D O3 1_656 0.96(2) 2.540(10)
                                     3.4170(10)
                                              152.0(10)
