#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2223385.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_2223385
loop_
_publ_author_name
'SiMa, Weiwei'
_publ_section_title
;
 <i>N</i>-Butyladamantane-1-carboxamide
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2492
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H25 N O'
_chemical_formula_moiety         'C15 H25 N O'
_chemical_formula_sum            'C15 H25 N O'
_chemical_formula_weight         235.36
_chemical_name_systematic
;
<i>N</i>-Butyladamantane-1-carboxamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 101.69(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.257(7)
_cell_length_b                   9.4353(19)
_cell_length_c                   9.5328(19)
_cell_measurement_reflns_used    4730
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      3.02
_cell_volume                     2841.2(11)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       '\w 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  0.0774
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14458
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.100
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.317
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1773
_refine_ls_R_factor_gt           0.0861
_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/[\s^2^(Fo^2^)+(0.0977P)^2^+2.0300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2007
_refine_ls_wR_factor_ref         0.2456
_reflns_number_gt                1544
_reflns_number_total             3260
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    hb5069.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_original_cell_volume        2841.1(10)
_cod_database_code               2223385
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'
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
C C1 0.30657(10) -0.1173(4) 0.4805(4) 0.0671(10) Uani d . 1
H H1A 0.3025 -0.1014 0.5774 0.080 Uiso calc R 1
H H1B 0.3146 -0.2157 0.4733 0.080 Uiso calc R 1
C C2 0.26562(13) -0.0911(5) 0.3781(5) 0.0935(13) Uani d . 1
H H2A 0.2702 -0.1038 0.2813 0.112 Uiso calc R 1
H H2B 0.2453 -0.1622 0.3941 0.112 Uiso calc R 1
C C3 0.24721(15) 0.0484(6) 0.3883(7) 0.143(2) Uani d . 1
H H3A 0.2643 0.1164 0.3488 0.172 Uiso calc R 1
H H3B 0.2502 0.0705 0.4892 0.172 Uiso calc R 1
C C4 0.20314(15) 0.0729(6) 0.3200(7) 0.152(2) Uani d . 1
H H4A 0.1997 0.0609 0.2183 0.229 Uiso calc R 1
H H4B 0.1952 0.1677 0.3403 0.229 Uiso calc R 1
H H4C 0.1854 0.0065 0.3564 0.229 Uiso calc R 1
C C5 0.36027(8) 0.0693(3) 0.5470(3) 0.0431(7) Uani d . 1
C C6 0.39355(8) 0.1604(3) 0.4964(3) 0.0411(7) Uani d . 1
C C7 0.41628(10) 0.2560(4) 0.6189(3) 0.0615(9) Uani d . 1
H H7A 0.3957 0.3154 0.6524 0.074 Uiso calc R 1
H H7B 0.4303 0.1979 0.6984 0.074 Uiso calc R 1
C C8 0.44885(11) 0.3491(4) 0.5667(4) 0.0715(10) Uani d . 1
H H8 0.4630 0.4095 0.6456 0.086 Uiso calc R 1
C C9 0.48163(10) 0.2564(4) 0.5166(4) 0.0795(11) Uani d . 1
H H9A 0.5025 0.3155 0.4844 0.095 Uiso calc R 1
H H9B 0.4961 0.1981 0.5952 0.095 Uiso calc R 1
C C10 0.45958(10) 0.1630(4) 0.3948(4) 0.0614(9) Uani d . 1
H H10 0.4806 0.1031 0.3624 0.074 Uiso calc R 1
C C11 0.42699(9) 0.0688(3) 0.4458(3) 0.0525(8) Uani d . 1
H H11A 0.4411 0.0091 0.5238 0.063 Uiso calc R 1
H H11B 0.4134 0.0078 0.3680 0.063 Uiso calc R 1
C C12 0.37184(9) 0.2551(3) 0.3720(3) 0.0513(8) Uani d . 1
H H12A 0.3576 0.1965 0.2932 0.062 Uiso calc R 1
H H12B 0.3507 0.3140 0.4030 0.062 Uiso calc R 1
C C13 0.40482(11) 0.3492(3) 0.3218(3) 0.0619(9) Uani d . 1
H H13 0.3907 0.4089 0.2422 0.074 Uiso calc R 1
C C14 0.42639(12) 0.4422(4) 0.4441(4) 0.0773(11) Uani d . 1
H H14A 0.4056 0.5012 0.4765 0.093 Uiso calc R 1
H H14B 0.4467 0.5036 0.4121 0.093 Uiso calc R 1
C C15 0.43746(11) 0.2543(4) 0.2710(3) 0.0674(10) Uani d . 1
H H15A 0.4234 0.1945 0.1929 0.081 Uiso calc R 1
H H15B 0.4581 0.3125 0.2364 0.081 Uiso calc R 1
N N1 0.34081(7) -0.0273(3) 0.4547(2) 0.0582(7) Uani d . 1
H H1C 0.3501 -0.0278 0.3622 0.070 Uiso d R 1
O O1 0.35154(7) 0.0859(2) 0.6660(2) 0.0619(7) Uani d . 1
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
C1 0.062(2) 0.075(2) 0.065(2) -0.0255(18) 0.0153(18) 0.0110(18)
C2 0.074(3) 0.087(3) 0.123(4) -0.018(2) 0.028(3) 0.022(3)
C3 0.086(3) 0.105(4) 0.244(7) 0.001(3) 0.044(4) 0.024(4)
C4 0.085(4) 0.126(5) 0.245(8) 0.003(3) 0.030(4) 0.008(5)
C5 0.0435(16) 0.0514(18) 0.0365(14) 0.0034(13) 0.0128(13) 0.0079(13)
C6 0.0425(15) 0.0466(16) 0.0357(14) -0.0005(12) 0.0111(12) -0.0016(12)
C7 0.069(2) 0.072(2) 0.0451(17) -0.0157(18) 0.0151(15) -0.0170(15)
C8 0.076(2) 0.078(2) 0.061(2) -0.032(2) 0.0136(19) -0.0210(19)
C9 0.055(2) 0.098(3) 0.085(3) -0.029(2) 0.0109(19) -0.003(2)
C10 0.0479(17) 0.071(2) 0.072(2) -0.0038(16) 0.0278(17) -0.0084(18)
C11 0.0473(16) 0.0553(19) 0.0565(18) 0.0001(14) 0.0142(14) 0.0015(14)
C12 0.0528(17) 0.0508(18) 0.0497(17) -0.0002(14) 0.0090(14) 0.0037(14)
C13 0.070(2) 0.056(2) 0.060(2) -0.0064(16) 0.0150(17) 0.0139(16)
C14 0.093(3) 0.050(2) 0.094(3) -0.0227(19) 0.032(2) -0.0086(19)
C15 0.070(2) 0.081(2) 0.059(2) -0.0260(19) 0.0307(17) -0.0057(18)
N1 0.0609(16) 0.0749(18) 0.0441(13) -0.0258(14) 0.0234(12) -0.0055(13)
O1 0.0715(15) 0.0796(16) 0.0407(11) -0.0063(12) 0.0263(11) 0.0002(11)
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
N1 C1 C2 113.2(3)
N1 C1 H1A 108.9
C2 C1 H1A 108.9
N1 C1 H1B 108.9
C2 C1 H1B 108.9
H1A C1 H1B 107.8
C3 C2 C1 115.1(4)
C3 C2 H2A 108.5
C1 C2 H2A 108.5
C3 C2 H2B 108.5
C1 C2 H2B 108.5
H2A C2 H2B 107.5
C2 C3 C4 119.2(5)
C2 C3 H3A 107.5
C4 C3 H3A 107.5
C2 C3 H3B 107.5
C4 C3 H3B 107.5
H3A C3 H3B 107.0
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O1 C5 N1 122.0(2)
O1 C5 C6 121.7(3)
N1 C5 C6 116.3(2)
C5 C6 C11 111.5(2)
C5 C6 C12 109.4(2)
C11 C6 C12 108.9(2)
C5 C6 C7 110.3(2)
C11 C6 C7 108.2(2)
C12 C6 C7 108.5(2)
C8 C7 C6 110.1(2)
C8 C7 H7A 109.6
C6 C7 H7A 109.6
C8 C7 H7B 109.6
C6 C7 H7B 109.6
H7A C7 H7B 108.2
C9 C8 C14 110.1(3)
C9 C8 C7 109.8(3)
C14 C8 C7 109.3(3)
C9 C8 H8 109.2
C14 C8 H8 109.2
C7 C8 H8 109.2
C10 C9 C8 109.1(3)
C10 C9 H9A 109.9
C8 C9 H9A 109.9
C10 C9 H9B 109.9
C8 C9 H9B 109.9
H9A C9 H9B 108.3
C9 C10 C15 109.8(3)
C9 C10 C11 109.9(3)
C15 C10 C11 109.4(3)
C9 C10 H10 109.2
C15 C10 H10 109.2
C11 C10 H10 109.2
C10 C11 C6 110.2(2)
C10 C11 H11A 109.6
C6 C11 H11A 109.6
C10 C11 H11B 109.6
C6 C11 H11B 109.6
H11A C11 H11B 108.1
C13 C12 C6 110.0(2)
C13 C12 H12A 109.7
C6 C12 H12A 109.7
C13 C12 H12B 109.7
C6 C12 H12B 109.7
H12A C12 H12B 108.2
C14 C13 C15 110.1(3)
C14 C13 C12 109.6(3)
C15 C13 C12 108.9(3)
C14 C13 H13 109.4
C15 C13 H13 109.4
C12 C13 H13 109.4
C13 C14 C8 109.3(3)
C13 C14 H14A 109.8
C8 C14 H14A 109.8
C13 C14 H14B 109.8
C8 C14 H14B 109.8
H14A C14 H14B 108.3
C10 C15 C13 109.3(3)
C10 C15 H15A 109.8
C13 C15 H15A 109.8
C10 C15 H15B 109.8
C13 C15 H15B 109.8
H15A C15 H15B 108.3
C5 N1 C1 124.1(2)
C5 N1 H1C 113.9
C1 N1 H1C 121.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.453(4)
C1 C2 1.496(5)
C1 H1A 0.9700
C1 H1B 0.9700
C2 C3 1.456(6)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.457(6)
C3 H3A 0.9700
C3 H3B 0.9700
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 O1 1.232(3)
C5 N1 1.333(3)
C5 C6 1.527(4)
C6 C11 1.535(4)
C6 C12 1.536(4)
C6 C7 1.539(4)
C7 C8 1.528(4)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.522(5)
C8 C14 1.523(5)
C8 H8 0.9800
C9 C10 1.516(5)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C15 1.517(5)
C10 C11 1.529(4)
C10 H10 0.9800
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.535(4)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.512(4)
C13 C15 1.533(5)
C13 H13 0.9800
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9700
C15 H15B 0.9700
N1 H1C 0.9861
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 H1C O1 6 0.99 1.96 2.896(3) 158
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
N1 C1 C2 C3 -65.2(5)
C1 C2 C3 C4 -165.0(5)
O1 C5 C6 C11 126.9(3)
N1 C5 C6 C11 -54.1(3)
O1 C5 C6 C12 -112.6(3)
N1 C5 C6 C12 66.4(3)
O1 C5 C6 C7 6.6(4)
N1 C5 C6 C7 -174.4(2)
C5 C6 C7 C8 -178.8(3)
C11 C6 C7 C8 59.0(3)
C12 C6 C7 C8 -59.0(3)
C6 C7 C8 C9 -60.3(4)
C6 C7 C8 C14 60.5(4)
C14 C8 C9 C10 -60.2(4)
C7 C8 C9 C10 60.1(4)
C8 C9 C10 C15 60.3(3)
C8 C9 C10 C11 -60.1(4)
C9 C10 C11 C6 60.4(3)
C15 C10 C11 C6 -60.2(3)
C5 C6 C11 C10 179.5(2)
C12 C6 C11 C10 58.8(3)
C7 C6 C11 C10 -59.0(3)
C5 C6 C12 C13 179.0(2)
C11 C6 C12 C13 -58.9(3)
C7 C6 C12 C13 58.6(3)
C6 C12 C13 C14 -60.3(3)
C6 C12 C13 C15 60.2(3)
C15 C13 C14 C8 -58.9(4)
C12 C13 C14 C8 61.0(4)
C9 C8 C14 C13 59.6(4)
C7 C8 C14 C13 -61.1(4)
C9 C10 C15 C13 -59.7(3)
C11 C10 C15 C13 61.0(3)
C14 C13 C15 C10 59.2(3)
C12 C13 C15 C10 -61.0(3)
O1 C5 N1 C1 2.9(5)
C6 C5 N1 C1 -176.1(3)
C2 C1 N1 C5 115.9(4)