#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006582.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_2006582
loop_
_publ_author_name
'Pr\"ohl, H.-H.'
'Blaschette, A.'
'Jones, P. G.'
_publ_section_title
;
 1-Acetamidoadamantane
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1434
_journal_page_last               1436
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C12 H19 N O'
_chemical_formula_weight         193.28
_chemical_name_systematic
;
 1-Acetamidoadamantane
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.06(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.312(5)
_cell_length_b                   9.464(2)
_cell_length_c                   9.454(3)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      10
_cell_volume                     2175.3(9)
_computing_cell_refinement       P3
_computing_data_collection       'P3 (Nicolet XRD Corporation, 1987)'
_computing_data_reduction        'XDISK (Nicolet XRD Corporation, 1987)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  SHELXL93
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      178(2)
_diffrn_measurement_device       'Siemens R3'
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2852
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 147
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.166
_refine_ls_extinction_coef       0.0055(10)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.029
_refine_ls_goodness_of_fit_obs   1.087
_refine_ls_hydrogen_treatment    'H atoms: see text'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_restrained_S_obs      1.087
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_obs          0.0387
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.5656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1151
_refine_ls_wR_factor_obs         0.0986
_reflns_number_observed          1355
_reflns_number_total             1915
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fg1344.cif
_[local]_cod_data_source_block   adamac
_[local]_cod_cif_authors_sg_H-M  C2/c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (10 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2175.5(9)
_cod_database_code               2006582
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_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
N 0.0327(7) 0.0323(7) 0.0187(6) 0.0054(6) -0.0050(5) -0.0004(6)
O 0.0503(7) 0.0421(7) 0.0228(6) 0.0134(5) -0.0037(5) -0.0016(5)
C1 0.0270(7) 0.0275(8) 0.0235(8) 0.0031(6) -0.0058(6) -0.0004(6)
C2 0.0327(8) 0.0306(8) 0.0269(8) 0.0021(7) -0.0024(7) 0.0012(7)
C3 0.0425(9) 0.0311(8) 0.0311(9) 0.0041(7) -0.0043(7) 0.0056(7)
C4 0.0483(10) 0.0306(9) 0.0455(11) 0.0100(8) -0.0073(8) -0.0021(8)
C5 0.0390(9) 0.0391(9) 0.0339(9) 0.0132(7) -0.0008(7) -0.0058(8)
C6 0.0317(9) 0.0505(10) 0.0467(10) 0.0101(8) -0.0024(8) 0.0023(8)
C7 0.0312(8) 0.0409(9) 0.0403(9) 0.0013(7) -0.0127(7) -0.0042(8)
C8 0.0326(8) 0.0302(8) 0.0320(8) -0.0006(7) -0.0061(7) -0.0016(7)
C9 0.0433(9) 0.0446(10) 0.0309(9) 0.0115(8) -0.0134(8) 0.0001(8)
C10 0.0356(9) 0.0362(9) 0.0250(8) 0.0046(7) -0.0024(7) -0.0029(7)
C11 0.0321(8) 0.0302(8) 0.0242(8) 0.0017(6) -0.0021(6) 0.0026(7)
C12 0.0372(9) 0.0403(9) 0.0287(9) 0.0091(7) -0.0023(7) 0.0027(7)
loop_
_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
_atom_site_type_symbol
N 0.31872(5) 0.43832(13) 0.37687(13) 0.0279(3) Uani d . 1 N
H0 0.3130(6) 0.4308(17) 0.2825(18) 0.033 Uiso d . 1 H
O 0.29022(4) 0.55109(12) 0.57614(11) 0.0384(3) Uani d . 1 O
C1 0.36096(6) 0.3472(2) 0.44164(14) 0.0260(4) Uani d . 1 C
C2 0.33481(6) 0.2448(2) 0.5475(2) 0.0301(4) Uani d . 1 C
H2A 0.30655(6) 0.1869(2) 0.4992(2) 0.036 Uiso calc R 1 H
H2B 0.31660(6) 0.2988(2) 0.6240(2) 0.036 Uiso calc R 1 H
C3 0.37909(7) 0.1482(2) 0.6108(2) 0.0349(4) Uani d . 1 C
H3 0.36182(7) 0.0823(2) 0.6806(2) 0.042 Uiso calc R 1 H
C4 0.40615(7) 0.0628(2) 0.4927(2) 0.0415(4) Uani d . 1 C
H4A 0.43464(7) -0.0002(2) 0.5331(2) 0.050 Uiso calc R 1 H
H4B 0.37823(7) 0.0034(2) 0.4449(2) 0.050 Uiso calc R 1 H
C5 0.43235(7) 0.1634(2) 0.3858(2) 0.0373(4) Uani d . 1 C
H5 0.44978(7) 0.1073(2) 0.3082(2) 0.045 Uiso calc R 1 H
C6 0.47634(7) 0.2527(2) 0.4599(2) 0.0430(5) Uani d . 1 C
H6A 0.50519(7) 0.1904(2) 0.4997(2) 0.052 Uiso calc R 1 H
H6B 0.49381(7) 0.3173(2) 0.3909(2) 0.052 Uiso calc R 1 H
C7 0.44950(6) 0.3381(2) 0.5783(2) 0.0374(4) Uani d . 1 C
H7 0.47809(6) 0.3964(2) 0.6270(2) 0.045 Uiso calc R 1 H
C8 0.40546(6) 0.4355(2) 0.5149(2) 0.0316(4) Uani d . 1 C
H8A 0.38866(6) 0.4932(2) 0.5908(2) 0.038 Uiso calc R 1 H
H8B 0.42262(6) 0.5003(2) 0.4456(2) 0.038 Uiso calc R 1 H
C9 0.42263(7) 0.2383(2) 0.6854(2) 0.0396(4) Uani d . 1 C
H9A 0.45094(7) 0.1764(2) 0.7282(2) 0.048 Uiso calc R 1 H
H9B 0.40527(7) 0.2940(2) 0.7620(2) 0.048 Uiso calc R 1 H
C10 0.38812(6) 0.2608(2) 0.3230(2) 0.0323(4) Uani d . 1 C
H10A 0.35993(6) 0.2036(2) 0.2737(2) 0.039 Uiso calc R 1 H
H10B 0.40505(6) 0.3255(2) 0.2532(2) 0.039 Uiso calc R 1 H
C11 0.28647(6) 0.5296(2) 0.4476(2) 0.0288(4) Uani d . 1 C
C12 0.24375(6) 0.6061(2) 0.3621(2) 0.0354(4) Uani d . 1 C
H12A 0.2423(3) 0.5659(7) 0.2667(3) 0.042 Uiso calc R 1 H
H12B 0.2533(2) 0.7065(3) 0.3563(8) 0.042 Uiso calc R 1 H
H12C 0.20777(9) 0.5958(8) 0.4076(6) 0.042 Uiso calc R 1 H
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
_geom_angle_publ_flag
C11 N C1 125.13(12) y
N C1 C2 110.62(11) y
N C1 C8 111.12(12) y
C2 C1 C8 110.07(12) y
N C1 C10 107.91(11) y
C2 C1 C10 108.61(12) y
C8 C1 C10 108.44(12) y
C1 C2 C3 109.91(12) ?
C4 C3 C9 109.48(13) ?
C4 C3 C2 109.42(12) ?
C9 C3 C2 109.40(13) ?
C5 C4 C3 109.51(13) ?
C4 C5 C6 109.42(14) ?
C4 C5 C10 109.74(13) ?
C6 C5 C10 109.48(13) ?
C7 C6 C5 109.18(13) ?
C6 C7 C9 109.95(14) ?
C6 C7 C8 109.27(13) ?
C9 C7 C8 109.32(12) ?
C1 C8 C7 109.95(13) ?
C3 C9 C7 109.53(13) ?
C5 C10 C1 109.78(12) ?
O C11 N 123.53(14) y
O C11 C12 120.02(14) y
N C11 C12 116.44(13) y
C1 N H0 118.0(10) n
C11 N H0 116.9(10) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N C11 1.345(2) y
N C1 1.474(2) y
O C11 1.235(2) y
C1 C2 1.532(2) ?
C1 C8 1.532(2) ?
C1 C10 1.537(2) ?
C2 C3 1.534(2) ?
C3 C4 1.528(2) ?
C3 C9 1.531(2) ?
C4 C5 1.528(2) ?
C5 C6 1.532(2) ?
C5 C10 1.536(2) ?
C6 C7 1.528(2) ?
C7 C9 1.531(2) ?
C7 C8 1.534(2) ?
C11 C12 1.501(2) y
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
N H0 O 6_565 0.91(2) 2.04(2) 2.928(2) 168.0(10) y
C12 H12A O 6_565 0.98 2.42 3.287(2) 148 y
C2 H2B O . 0.99 2.51 3.107(2) 118 y
C8 H8A O . 0.99 2.46 3.064(2) 119 y
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
_geom_torsion_publ_flag
C11 N C1 C2 61.6(2) y
C11 N C1 C8 -60.9(2) y
C11 N C1 C10 -179.69(13) y
N C1 C2 C3 178.46(12) ?
C8 C1 C2 C3 -58.4(2) ?
C10 C1 C2 C3 60.2(2) ?
C1 C2 C3 C4 -60.6(2) ?
C1 C2 C3 C9 59.3(2) ?
C9 C3 C4 C5 -60.1(2) ?
C2 C3 C4 C5 59.7(2) ?
C3 C4 C5 C6 60.6(2) ?
C3 C4 C5 C10 -59.5(2) ?
C4 C5 C6 C7 -60.2(2) ?
C10 C5 C6 C7 60.1(2) ?
C5 C6 C7 C9 59.7(2) ?
C5 C6 C7 C8 -60.3(2) ?
N C1 C8 C7 -178.70(12) ?
C2 C1 C8 C7 58.4(2) ?
C10 C1 C8 C7 -60.3(2) ?
C6 C7 C8 C1 61.0(2) ?
C9 C7 C8 C1 -59.4(2) ?
C4 C3 C9 C7 59.3(2) ?
C2 C3 C9 C7 -60.6(2) ?
C6 C7 C9 C3 -59.4(2) ?
C8 C7 C9 C3 60.5(2) ?
C4 C5 C10 C1 59.8(2) ?
C6 C5 C10 C1 -60.3(2) ?
N C1 C10 C5 -179.68(12) ?
C2 C1 C10 C5 -59.7(2) ?
C8 C1 C10 C5 59.9(2) ?
C1 N C11 O 2.8(2) y
C1 N C11 C12 -176.49(13) y